Patrick O'Shaughnessy
Appearances
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Say why you like this idea, what a contained business means and what an uncontained business is and why you like to avoid them.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Would like software tooling be a good example?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Give us an example of the process you go through to explore a contained system. You're coming across a new company for the first time. you want to start to learn everything. What is your method for doing that? And I recognize that like to some degree, this is like an obvious answer. You talk to people, you read stuff, you think about it.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
I always love these moments where you get like some new click of understanding and maybe you could tell the story of one of those clicks of understanding or something from the investing history.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
If I was thinking about how you would spend your time, it would seem to be incredibly valuable to collect models like this over time. Do you find your way to most of them through a specific business? Which comes first, the business or the mental model?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
To drive home the point, can you do one more like the Cornell Oligopoly, just to give us a flavored sense of another thing that you've used in the past? Secondary reinforcers.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
And I guess the valuable thing in markets would then be that markets don't properly value that insight. Like if you look at Philip Morris, at one point it was the best performing stock in U.S. history or something like that for like decades and decades. So it would like corroborate this idea that it's probably like a valuable insight.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
But at some point it gets priced like like insights all get priced. And so maybe that's what you were talking about earlier, which is you need a confluence of these things in an area that's been neglected to find an interesting opportunity, something like that. Yeah, you need something that scares people away.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
You know, if you think about the classical ways of finding edge in markets, it would be informational, which seems kind of gone. Analytical, which is a lot of what we're talking about. And then I'll call the last bucket like structural or behavioral or something like that. What do you think about ESG?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
It comes to mind because of the nicotine examples where there's just a class of investor that's not allowed to own it, which creates like a weird impact on markets, especially if those asset owners are very large. What do you think about ESG?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
I think now's a great time to tell, devote a long block of time to your investment in Carvana. I think people that know you and your firm's history will certainly associate you with the position. It's been an enormous position for you over time. You're one of the biggest investors in the business.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
And for me, one of the reasons I've asked you so many times to do this is that let's say dating back five or six years now. I've had the chance to talk to you about this company through its many ups and downs.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
And it's been one of the most interesting educations that I've received from another investor on investing, just talking to you every so often about this company and what you're thinking about it. And so I've been lucky to enjoy that, you know, the audience of one. And I thought it would be an amazing opportunity to hear you tell the story, which is very complicated.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
It's a complicated business story. It's a complicated investment story. Your own story about how you were going through it all is interesting and complicated. There's all sorts of dimensionality to it. You were joking that it's like five rivers coming together. You kind of have to explain each river, but we have the luxury of time here.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
So I don't know how best to start with which river maybe you can pick, but I want to devote like a lot of time and I'll have lots of follow-up questions because I just think like, you can go look at the Carvana price chart. You can listen to my two conversations with Ernie. There's lots of stuff out there about Carvana.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
But the thing that I find interesting is the investor's perspective as the person that probably had the biggest position, held onto it, bought more, has been with it the longest. You sort of had the most holistic perspective on it. And I want everyone to benefit from what it's like to own and live through one of those episodes.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Especially now that we've laid the groundwork for how you sort of apply ways of thinking to understanding a new company. And so maybe even make it specific to you. Like how did you encounter it? What were some of the models that, you know, felt relevant to you as you tried to learn about the business and use that as a way to introduce like how the business works?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
My guest today is Cliff Sosin. Cliff is the founder of CAS Investment Partners, a fund he started with $5 million in 2012 that's now $1.7 billion. This conversation is different from our typical episodes. We start by talking about Cliff's investment philosophy, but the bulk of this long discussion is a case study into his remarkable investment in Carvana.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Mobile.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Cliff is one of the biggest investors in the business, which had a market cap of over $60 billion in 2021, then fell 99%, survived, and now has a market cap approaching $50 billion again. While I hosted Carvana's CEO Ernie Garcia last year to get the inside perspective on managing through such turbulence, today we hear the investor side of this extraordinary story.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
It is a singular episode and a rare opportunity to hear a major investor describe his decision-making process at every stage of a volatile journey. Please enjoy my great conversation with Cliff Sosin. Cliff, I'm so excited to be able to do this with you. I've been asking you to do this for at least three to four years, something like that.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Everything's there.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
So I don't know what made you capitulate, but it's an excuse to talk to you about investing in general and some very interesting specific episodes that you've been involved with specifically. And I think we got to start broad because I want to set the context for everyone that doesn't know who you are or what your setup has been. Maybe just give us like a history of how you started the firm.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Just to pause on the concept of combining skill, scope, trust, traditional economies of scale of different types. Is there another business that comes to mind, maybe it's Amazon, that you think... captures all these same things that has interested you through time, just to draw a comparative point for people.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
I've interviewed Ernie a few times. My bias is that I think very highly of Ernie, and he's a much maligned figure because of everything that's going on with Carvana. And it's so fascinating to me to hear all the different Rashomon-style parts of the story So I'll put out there that I think very highly of Ernie based on what I've known. I haven't studied the business like you at all.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
I don't own Carvana. I don't have a dog in this hunt financially. But I think it's important to say a little bit about management.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
And maybe it's also an excuse, since I haven't asked you yet, to talk about how you think about management as it relates to certain businesses and where you fall on the spectrum of leadership is everything to the Buffett ham sandwich concept of a business that's so good that a ham sandwich could run it because someday someone will or one will.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
So talk about Ernie, the management team behind the team behind Carvana and kind of your philosophy on management and investing.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
What was it, 2012, something like that? Why you started the firm and kind of what it's been since.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Now we get to talk about the tough part of the whole story and experience. What went wrong with the business? Just tell us the whole story. Like what it was like to be one of the larger investors in the business as this was going wrong. What did you do? How did you second guess yourself? What was the psychology like? Like I'm interested in all aspects of it.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
This is where the 99% part comes from.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
It's kind of like when oil goes negative, like this is not supposed to happen.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Can you talk about your investing decisions? Because during that period, like every day is kind of a decision, like not selling is a big decision as the information comes online. What did you do? Like, did you buy more? Were there constraints on how much you could buy? Would you have done anything differently in hindsight?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Like, what were the frictions that obviously you wouldn't have bought more in hindsight. Stupid question.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Very stupid question. I think you know what I mean. Like what were like the real, walk us through like the psychology, the barriers, the like, you know, the real hard stuff.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
So say a little bit about the... the range of psychology and maybe like how close you got to thinking, you know, just really deeply questioning yourself. Like you're one of these investors that typically knows when I've talked to you about companies, you've known more about the company than anyone else I've talked to about that same company. And that's always been the case with Carvana.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
I think that was true prior to the 99 decline. It's probably true today. But even despite that, even though you knew so much, it's sort of like the Navy Federal Credit Union X factor thing. Like, how are you wired? Like, how... distraught did you get?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
It's such an... I'm so glad we did the long version of the story because whether or not people care about this specific stock, I just think as an investing and business story, it is... very singular. I said this on the Ernie episode. We looked, because he gave me that stat about going down 90% is like going down 20% 20 times or something like that. And each one's painful.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
There really is not another example of a company that was that big by market cap or something that went down 99% that survived and wasn't a fraud. That's an N of one. It doesn't exist in the record. And so it's so cool to hear its major investor talk through the entire thing from soup to nuts.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
And I guess in conclusion, I'm curious how you think you will most approach future investment opportunities differently as a result of having had this specific experience personally.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Has it made you think any differently about your appetite for concentration. Just like I think of that old quote, like the only rational deployment of our ignorance is diversification.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
And that like, it's not ignorance so much. It's just like the Navy Federal Credit Union factor. Like that stuff happens in the world and a simple way to protect against that, you know, the idiosyncratic math of like, whatever, at 15 positions, the risks all gone. And like, why not have 15 positions instead of five? Like, has it made you re-question That stuff?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Obviously, your portfolio is the answer to this question. So maybe the answer is no. But curious what you think.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Well, it's an incredible story. I'd love to take our remaining time and talk about the world and the future and investing kind of writ more large. One of the things I think we're allowed to talk about IQ again, which is why I'll frame the question this way. If you think about like the world's stock of processing power in human brains.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
you know, some measure of the number of people with a certain amount of processing power plus like how efficiently they use that or if they use it productively or if they just play video games or something. And then we think about the introduction. There's a question about the introduction of artificial intelligence into the world, which I'm curious for your take on generally.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
But I'm also more specifically curious for your take on the introduction of intelligence and processing power into the job of investing, of like ingesting information, looking for stuff that overlaps, training on past pattern recognition and what's worked in businesses historically. And if we fast forward 10 years or something, what it's going to be like for even a very smart human to
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
So what did you tell your original investors? Because some people gave you money, including some well-known institutions. What did you tell them and why were their decision-making processes different? And how much did you start with?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
to invest in a world that is full of artificial intelligence. And I'm just curious. I haven't talked to you about this before in such specific terms. I'm just curious for your take on the whole thing, how you've processed watching it unfold in the last couple of years and how you think it'll affect this job.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Your portfolio is I don't know if it's entirely, but it's been historically mostly U.S. companies. If I think about the US, you've got all these incredible advantages. We're the home of innovation. We've got this incredible geographic isolation and abundance here domestically. Our currency has been the reserve currency of the world. We sort of control our own destiny in those ways.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Any observations just about the US as what historically has been the most fertile soil for finding great investment opportunities in kind of the modern era and whether or not that is changing one way or the other?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
I think it's so interesting and funny that lots of the big investors out there have gotten to the position they're in owning Microsoft and Amazon and these exciting big, like no one gets faulted for this. And we're talking about used cars and subprime lending and things like this. I used to own multi-level marketers too. All right, of course.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
And it's just so interesting how many different ways there are to do really well in investing. And maybe the last question I'll ask before my traditional closing one is just how you process the really big, like I'm sure you think Microsoft is a great business, like objectively it's just a great business.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
How do you process those ones that are so dominant in the market that are such a huge percent of the market's market cap or whatever? How do you think about for your own money? I know you're a huge investor in your own funds. Your own fund. Do you want exposure to those things? What do you think about market exposure for the average person?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
It seems like a very sensible thing for the average investor. Do you ever feel strange that there are these massive, incredible, what seem like enduring businesses that you have nothing to do with?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Whenever we talk, time flies by. There's 20 things I could ask you about. Maybe I'll convince you to do this another five years. We could talk about those then. But for now, I have to ask my traditional closing question. What's the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
It's great. Beautiful stories. Cliff, thanks for finally doing this with me. Thanks for your time. If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
You can also subscribe to Colossus Review, our quarterly print, digital and private audio publication featuring in-depth profiles of the founders, investors and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
And where does that bring us today? So how many investors do you have? What's kind of the capital base? Like, how do you think about the firm today?
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
What is your view of investing in markets? Like, describe how you think it is supposed to be done in some detail.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
Yeah. So I guess like the obvious and very simple, but very big question is like, what is a good business? Like what is that taxonomy? Maybe this is the time to talk about one of my favorite ideas of yours that you like businesses you described as contained. I've always liked that description when we've talked about companies. Yeah, give us your kind of view on what makes a good business.
Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I'm curious because you've earned the answer to this next question more than most people that I've ever met. In addition to that idea of preparation, what are your other most deeply held beliefs about leadership and what makes for great leadership, both from earned lessons yourself, but also from the leaders that you worked with for around?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Is there an episode of leadership from someone in your orbit during your time overseas that most exemplifies leadership to you that you saw some other leader perform?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I have a question, which is a hard question to ask and maybe an impossible one to answer, but I'm asking it because I want the way I think of you is like you've gone a level up. And the way that you started ID me was to serve this community in a deep and real way. And we'll tell that story in a minute.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
But this is also abstract for us that haven't been in service, certainly not in such incredible harm's way.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I'm just curious to help people understand the people that are doing this for us, the nature of taking life or seeing life taken amongst your friends as the ultimate stakes and try to help people understand those stakes because I'm sure the answer is there's no way of understanding it unless you go through it yourself.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
But this is the ultimate sacrifice that so many people put themselves in this kind of harm's way. Do you have a closing thought on just the nature of that life of living that experience that people can understand why this group is so critical to support?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I'm so grateful for this first 30 minutes and you sharing all this. It's an incredible, incredible story. I and we all listening, I'm sure are so grateful for what you and your team and everyone else like you did and does. I think it's the perfect bridge to. set up why you started the business that you're now leading.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Originally, I want to harken back to that 12 versus 15 months and the sort of the benefits that were supposedly accessible to the people for those extra three months that they deployed, but how hard those are for our veterans to get and that kind of original intention and nature of your idea for this business.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
So maybe you can bridge that story for us and tell us what you did originally when starting ID.me, why you did it and who you originally served.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Can you tell us the story of the earliest days and the very first things that you did and for whom and why you cared about those specific things at the start that's grown into this big thing?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
It's like, what is that? Completely wild start to this whole thing. And so tell us, what was that pitch? What were you pitching them with TroopSwap that became IDMU?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. Invest Like the Best is part of the Colossus family of podcasts, and you can access all our podcasts, including edited transcripts, show notes, and other resources to keep learning at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I have one question going back to something you said earlier around the book that David gave you the four steps to the epiphany of the Steve Blank book. Is there anything from that book that you looking back on that time find to be the most valuable that other people out there should think about?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Yeah, the genetics of the business are bad and therefore screwed. I'm starting to wonder then about if we zoom all the way to today, if you can give us sort of an overview on the topic and the importance of identity. This is something that I met you through Mickey at Ribbit.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
And Mickey and I are having this long, fascinating discussion about the role that identity has played and will play as a sort of like primitive for millions of workflows and products and actions that we take as humans. And it was something I really hadn't thought all that much about.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
You take it for granted that like you prove your you in a variety of different ways and some are janky and terrible and some are whatever. But I never really thought about it too much. Could you give us the sort of overview as you see it on the role and importance of identity as a function in the modern economy?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Oh, God, I don't know. Some crazy number. Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
My guest today is Blake Hall. Blake is the co-founder and CEO of ID.me, a secure digital identity network with over 100 million members. He was an officer in the United States Army and served our country for four years as a rifle platoon leader, battalion reconnaissance platoon leader, and as a battalion logistics officer.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
We explore his formative years in the military and transition into entrepreneurship. Blake shares powerful stories from his time leading scout sniper missions in Iraq, including how his unit achieved a 90% success rate in high-stakes operations through relentless preparation and learning.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Can you describe the building blocks of signing up to begin with to say me as a human being is like some like verification and authentication process? Those are different. How do you do that? What are the ways that I prove that I'm me? And I want to also ask about the non-ID.me versions of this.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I remember you telling me like a branded relationship with the customer like Apple might have or Google might have or Clear might have. So I want to talk about the ecosystem and not just ID.me, but the ecosystem of people that represent a way to prove your identity and get access to something or stop something. So what are the building blocks? How do you literally know a person is a person?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Walk us through that. It seems it's a really important thing for the future.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
He shares the origin and evolution of ID.me, a company dedicated to verifying digital identities to combat fraud and simplify login experiences. We discuss the role of identity in the modern economy, frameworks for building company culture, and evaluating executive talent. I am ridiculously inspired by Blake and I'm so grateful for him and all the Americans who serve this country.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Please enjoy this discussion with the awesome Blake Hall. Blake, I was wondering where to begin our conversation based on prior ones that we've had. And one place that is really interesting for me and I've always been fascinated by is your experience in the military and specifically the experiences you've had that have taught you lessons that you think would be pretty impossible to learn.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
We obviously won't have time to go into all the intricate ways that you've built this network. And I think the shorthand you provided is right. Yeah. For me, instead of going to the VA with my documents to get my extended 15-month deployment benefit, I can just do it digitally and much faster.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I know it's more complicated than that, but at its most simple, that's a convenient way for us listening to think about it.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Obviously, everyone that's interested in investing has done some amount of time studying Visa and MasterCard as these gold standard business models. There really aren't higher quality businesses than these things because the network effect associated with them is just so incredibly powerful and therefore their margins are crazy high.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
had you not had the experiences you had in the armed forces. And so maybe you can tell us a little bit about a sketch of what you did. And then I want to spend some time on some of the formative stories that have shaped your worldview that maybe you wouldn't have been shaped that way had you not had those experiences.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I've heard you describe what you're doing as like Visa and 3D in some dimension. Can you just describe the business lessons that you've learned from Visa and why you think the way that you're building ID.me will be such a good enduring process? business beyond just the service that it renders for its customers?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
There was another source of inspiration, which I found really interesting, which was Disney and how they think about authentication. What did you learn from Disney?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
You mentioned the attacks that you suffered when you came between the international bot armies and their pot of gold. What have been the ways that more legitimate entities have tried to kill you? Who do you threaten that isn't like an illegal attacker, but is like an incumbent US company or something like that? And what's that been like?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Yeah, it's a fascinating experience. I'm sure you told me last time we talked about this, that you're a ranger and you can get ambushed once, but not twice. So what does that make you think about the future about like part of this building an enormous business necessarily bumps into lots of other entities that are self-interested?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
So I'm curious about what you think about credit bureaus, the role that they play. in all of this or other groups of entities like this that you may end up displacing and improving upon for the end customer. How do you think about that as part of your job, that it's not just this idealistic, like we're going to build something really nice and everyone's going to be happy.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Not everything is positive. Some you're taking share from somebody else in some way. How do you think about that as part of your job as a leader?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
What role do Clear, Apple, Google, other huge players like that play in this whole identity story to you?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
And what was the brief timeline of your personal experience in the armed forces? What did you do? Where were you? Paint the picture for us.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
If you think about the, let's say, five year hence future to give it not infinite time, but decent chunk of years, what's your dream for the state of ID.me and what it's doing for people on that time horizon?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I would love to know how you decided what your business model would be and what you've learned about designing a business model alongside a valuable product. Because in your case, when you've got this network that's growing and the surface area of the network is so big, and there's lots of different stakeholders.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
You've told stories already today about how governments are beneficiary, how consumers are beneficiaries, how companies might be beneficiaries, how banks and other intermediaries might benefit from the use of this network. So there's lots of ways that I could imagine you making money by doing your job and having your product be in market. And you've chosen a subset of those or one of those.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
How did you do that? What are your principles that others might borrow for? OK, I've got a good idea that's valuable. It's valuable to lots of people. I'm not really sure who should pay. And how did you get to that answer? And maybe just describe it a little bit for everyone.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
You said something to me about the business, which I found so interesting, which is that you don't want diversity of values at ID.me. I want to ask a couple of questions about just the principles and the culture in that step four of the C-blank book and how you've thought about philosophically deploying those things. Maybe start with that one as an example.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
and then riff on the other principles that you've established, like the one for business model there in building the business and the power of those principles.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
What were the two other things that your grandfather told your dad?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I love it. On the topic of performance, you turned me on to something I hadn't heard of before, which is this stratum concept behind levels of leadership. Can you explain what that is and how you found it useful?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Can you describe maybe anecdote sounds like the wrong word, like a story within the story of that 15 months that pops most immediately to mind to zoom it in on a specific episode, just to understand what you were doing?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I have so enjoyed you teaching me and now us about not only your story, but the system that you yourself are building and working on the potential implications of it. I think your story, my obsession with this notion of life's work, and it's stories like yours that I'm always trying to find more of to be able to show people as examples.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Obviously, no one's going to live your exact story, but the authentic nature of it, the unique nature of it, the way you've embraced challenge and risk and all these things, I just find deeply inspirational. So thank you for doing this with me today. I ask everyone the same traditional closing question. What is the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
Thanks for saying so, Blake. This has been such a total pleasure. Thanks for your time. Thanks, buddy. If you enjoyed this episode, check out joincolossus.com. There you'll find every episode of this podcast complete with transcripts, show notes, and resources to keep learning.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
You can also sign up for our newsletter, Colossus Weekly, where we condense episodes to the big ideas, quotations, and more, as well as share the best content we find on the internet every week.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I want to come back to, you said something there, which reminds me of what you're building now, which is the fact that you got extended from 12 months, I think to 15 months. And I'm putting a pin in that because that's going to become a relevant detail when we talk about the origins of the business in a little bit.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
I'm curious in that stretch of time, what did you learn about yourself that you didn't know prior?
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Blake Hall - Combat, Service, and Innovation - [Invest Like the Best, EP.408]
What did you do to drive from average to 90% as the leader?
Invest Like the Best with Patrick O'Shaughnessy
Graham Weaver - Building Alpine - [Invest Like the Best, EP.425]
That's the platform.
Invest Like the Best with Patrick O'Shaughnessy
Graham Weaver - Building Alpine - [Invest Like the Best, EP.425]
To learn more, visit psum.vc.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
If you think about that outcome and you decompose it into a couple of things, a bet on cybersecurity, a bet on these nine people, a bet on the business models or the way that they approach the market, and then some other catch-all bucket, what do you think were the most important contributing factors to that first fund's success and the success that has continued to happen since?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
The hit rate's crazy. The number of huge outcomes is crazy. Maybe the fourth bucket is luck. How would you break out the reasons for the success? Luck is definitely important.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Pretty good.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Let's step through that process, starting with founder traits. So you're betting on people, many of whom don't have an actual idea yet. And so you're really just incredibly focused on the quality of the person. What have you learned about what matters? What are you looking for?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
How much of your evaluation of these people is effectively just saying, tell me your life story? And if they literally just answered that question in detail, it would be all you need. And if it's not all you need, what else do you need?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
If you think about the next step, you select someone, they've got this personality type that you love. You then go on a hunt for the right problem. And maybe this is just the excuse to talk about the sunrise methodology that you've established. Walk us through that process.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
I want to highlight how strange this is relative to, if you think about the outcome so far, I'm not aware of another early stage investor that's this systematic with this high a hit rate in such a narrow field. And so I think spending extra time on the methodology from here, let's just assume you can find great people, which I know is hard, but you've got a batch of great people.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
What was the origin story behind Sunrise? What is it? How did it come to be?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Can you describe that piece specifically in some detail, the tactical method for who you're talking to, how many people you talk to, how often you do, like the real details here? I think it's such an interesting process.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
If I back up now and think about the process so far, it's the identification of these people that have this super resilience history and gene. It's the application of the Sunrise program to start identifying and then ultimately pick a problem that's super valuable using these unique set of questions. What's the next phase?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Are these things built in a distinctive way relative to the normal startup that you've observed before? Or is it at that point a standard software building exercise?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
One of the things that is incredibly interesting to me is how you must drive low cost of capital for these companies because of your involvement. I would imagine you've got all sorts of other investors with deep pockets that desperately would love to sort of blindly fund companies that are partnered with you at Seed, at the Series A or the Series B or beyond.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
How do you help the companies manage their future financing? And how do you think about how aggressive to be on valuation and how much capital you raise in dilution. This is a really interesting part of what you've built with such a high hit rate. We think at CyberStarts of co-investors as partners.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
How do you think about pricing at seed for yourself? What's the right way to think about this? How much variance is there between the valuation at which you've tended to enter companies? Has that changed a lot since 2018? It almost didn't change in seven years.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
You don't mind paying it because of the extra information you have about the founder on a repeat basis?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
How many other places do you think, in addition to cyber, this method could be applied successfully? Or is there something still in 2025 really distinctive about cyber versus other spaces that make it by far the most fertile ground for applying something like Sunrise?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
How would you rate today's environment for prospective returns? Your returns have been crazy high. Do you think the next five years have the chance for similar returns or have prices made earning those kinds of returns and the market itself much harder?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Speaking of those individuals, we talked a little bit earlier. I'm just so fascinated by the questions that you ask as you're identifying these people. And I'm thinking to your time with Mike and Doug at Sequoia, again, famous for asking people about their early lives and whole life stories.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Are there any other favorite questions that you have to ask people to understand them as deeply as possible that we haven't talked about?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
What if you had to answer that question for yourself?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
What do you think the hidden superpower is? That's your true number one, but you're not as consciously aware of.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Where do you find satisfaction?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
We have the opportunity, given the timing here, to talk about an incredible investment, Wiz, that, of course, is the item of the news of the last, I don't know, year in the venture world, an incredible outcome in the acquisition from Google. We won't talk so much about the outcome as the process and your experience and story of working with the company.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
We've talked a lot in our interview about why you do what you do, the process by which you found founders, what you look for in them, the process to find product market fit, the Sunrise methodology, et cetera. And here we have the ultimate case study in why these ideas are powerful in combination. So I would love to just hear the story from your perspective. You're right.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
My guest today is Gili Renan. Gili is the founder of CyberStarts, a VC firm focused on cybersecurity and the world's first VC that is majorly backed by cyber entrepreneurs. CyberStarts' $50 million first fund exploded to close to $2 billion in just three years. Gili describes cybersecurity today as the perfect storm where global conflicts and AI advancements are creating unprecedented threats.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Wow.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Can you say a little bit about how you won such early involvement with a team that was obviously so strong? The ongoing lesson from the stories that have come out since the acquisition news is some of the very high multiples, nominal revenue multiples that were paid by subsequent round investors who nonetheless earned an incredible return, even though they paid high multiples.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
And I'm curious what you learned from watching that dynamic unfold, having been the earliest investor in the business.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Is there any other novel lesson? I love the three points that drove the success that you outlined. And I love the idea that the high price thing is an old lesson. Are there any other new lessons that Wiz taught you that are unique to your experience with that specific company?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
I'm just testing it.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
He talks about CyberStart's Sunrise methodology, which uniquely identifies customer pain points before building solutions. We discuss a focus on finding resilient talent, overcoming personal adversity, the evolution of the cybersecurity landscape, and Google's recent acquisition of Wiz, where CyberStarts was one of the earliest investors. Please enjoy my conversation with Gili Renan.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Do you think it can be broken in cybersecurity specifically? Yes. Why? Why do you think that's possible? Just because it's changing and so big?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
I think it's very, very feasible. If it happens, I wouldn't be surprised if you're involved from the very earliest stages and if the Sunrise methodology and your approach works again. I appreciate that. If you think about the stories of resilience that you look for in your founders, it's a nice thing to say.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Can you tell me the story of the hardest episode of resilience that you've had to personally go through?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
How is that possible? Everyone listening, myself included, with children knows that's the single worst thing one could imagine. How is it possible to get beyond something like that?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
I love the message of focusing on young people and building things for others. It seems like your orientation and your satisfaction and your strategy and your search and your work is very other oriented.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Anything you would say to other investors out there that hear that part of your story, and that's the piece that appeals to them most, helping other people and what they build and how they do their work.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
If you think about the future of cyber, what challenges, evolutions, things that might happen excites you most or worries you most? I guess both.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Gilly, I've been so excited to do this with you, in part because in the 500 or so episodes of this, I don't think I've ever talked about the thing you invest in, primarily cybersecurity. And because your personal investing story and life story is so damn interesting, we're going to go all over the place. Maybe you can just give us the very high level state of the union in cybersecurity today.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
It's totally remarkable what you built in a short period of time. I'm sure the CyberStart story is in its infancy and that we'll be able to do this in five years and a whole new set of challenges will have arisen, like you said, probably unpredictable. Thank you for doing this with me. When I do these, I always ask the same traditional closing question.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
What is the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Close to 500 times, I've never heard that answer. These answers tend to cluster in a couple of key themes, variants of key themes, three or four. I've never heard that one with a son of my own. It hits you right in the face. All that must have gone into that thing he told you. Really a beautiful, amazing place to close. Gilly, thanks so much for your time. Thank you, Patrick. Really enjoyed it.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts. You can also subscribe to Colossus Review, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
There's lots of risk ahead of us. I'm curious if you could analogize cybersecurity, offense, and defense to simple military concepts or something like this. If I think about the evolution of kinetic warfare from muskets up through nuclear weapons or something, is there some similar escalation of The tools being used by attackers and defenders in cyber, have the targets changed over time?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
The goal of the attackers changed over time? If I were to think about the evolution of the battle, what are the key steps in that evolution?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
I think this is reality today. What does that mean in terms of attack targets? What are the offensive system? Let's say a bad actor. What are they trying to disable? What are they trying to shut down? What is the primary most damaging strategy of the attacker today?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
That's today. What does that mean in literal terms? So when you describe it that way, what comes to mind is an agent that can brute force create ways in and just try them all. One lands and is successful in its attack. Is that the right way to think about it? Or is it, if that's a shotgun approach, is it more of a rifle approach enabled by the agent in a way that wasn't possible five years ago?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
If I think about the average lifespan of a cybersecurity company in this state of the world today, and let's say the next 20 years, there's that famous chart of like the average lifespan of a company in the S&P 500 that's getting shorter and shorter and shorter. Does that line look even crazy or steep for cybersecurity companies?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
If the attack and defense vectors are evolving so quickly, how can a company build enduring value? The answer is fairly straightforward.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
It's a machine that attacks you. Can you tell the story of the first fund, which I think will probably go down as one of the most spectacular early stage investment funds ever? I would love you to share the numbers and the companies and just what happened. It's the sort of thing of legend now. And then I want to build on that for how you built the business afterwards. You started in 2018.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
The first fund was small. Tell the story of that first fund.
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
Can you give those? Touch on like some of the major learnings and mistakes and lessons, like the key ingredients that were in place in 2018 from your experience that went into that first investment fund?
Invest Like the Best with Patrick O'Shaughnessy
Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
How soon do you think it's the case that in-person work meetings have the same expectations as a Zoom meeting? I actually am already there. I am already frustrated that with no nefarious intent, I just wish I had a memory assistant that was with me that I don't have to think about notes. I can just be engaged in a conversation. I wish that was the norm today.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
And maybe there's just like a social thing that happens where you just decide at the beginning of a meeting, is this one recorded or not? And I wish that was easy. Like I would wear the pendant now just because I meet so many interesting people. I can't keep all this stuff straight in my head. I furiously try to take notes afterwards. It doesn't feel that different. When do you think we get there?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
One of the things that I'm so curious about right now in the world of AI application companies is this small team meme, where some of the most incredible tools are built by teams smaller than 25 people. And as they scale their user base or their revenue, the teams are really not getting bigger. They don't need bigger teams.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Can you describe what it's been like in all its aspects, abstracting away a little bit from the product itself, but just building a company in this space relative to prior companies that you built or were a part of in the pre-AI era?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Is that mostly engineering challenges where you would expect that using cognition and cursor and whatever else your team would be able to effectively be like a manager versus an engineer and just tell it what to do and you wouldn't have to actually engineer the endpoints?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Is one of the key lessons there that a lot of what needs to get built both technically and as like an expectation for people is context gathering tools. You're doing one obviously for conversation, and that's one mode of input that's really, really, really important, especially for work. How do you think we'll capture the rest riff on like context gathering as a function?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Bring that to life a little bit more for me, the fluidity aspect. How could you imagine that being like versus the back and forth?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Have you been surprised by any of the ways that users use Granola?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
As an app builder, what is your perspective on the battle between model providers for your attention and business? It's the best thing ever. It's fantastic.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
How is it built? Are you sort of hot swapping the best model in? And that's just something that you could do in the morning every time, you know, Anthropic apparently is coming out with this new model soon. Will it just be a function of like a quick eval and then hot swap that thing in as the primary driver and then switch again in the future if the new one comes out? Is it that simple?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
And how do you think about the competitive dynamics of what you're building versus what might be achievable through using a model directly alone? Everyone always used to ask, won't Amazon just build this or won't Google just build this? Now it's like, won't Anthropic just build this?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
How do you think about building in such a way that's protected from the future in which the model companies come to eat your lunch directly?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Do you have like a crystallized product philosophy that guides your decisions?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
You gave the personal. Is there anything that's different about the granola-specific product philosophy?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Are you at all surprised by who your users are, what types of jobs they do, or do they tend to cluster in a couple sectors? What have you learned just based on the raw data of who they are?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Yeah, it makes sense, right? It's very much in like the Jeffrey Moore, like crossing the chasm, early adopter, natural early adopters.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
That's what I did to you. Like it's the same exact thing. This is such an interesting way to meet people quickly. I'm curious in this whole building process, Is there any plot twist that you look back on that turns out in hindsight to have been a blessing or a gift in your whole product building experience?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Has the process made you change your mind in a major way about anything?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
If you think about the model providers as one vector of competition for the job to be done, how do you think about the other vector, which is other app builders and the ways in which how you architect the product might defend you because it's becoming more and more sticky and valuable to the user or something?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
So that even if another Granola 2.0 comes out that's a little bit better, they're not going to adopt it. Do you think a lot about that sort of thing, even though you're super, super young and I'm sure mostly just focused on building something great for users? Does that line of thinking enter your mind?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Tell me how you do that with your team. So I've heard a few different fascinating methods for engineering product velocity in a company, building an app on top of AI. How do you think about it and do it? What's worked? What experiments have failed? Like how do you engineer product velocity?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
I mean, that's the whole challenge. How do you think about dialing your own degree of ambition? Like if it's one through 10, where do you think it is? And has it moved a couple of points up since you started? What is the process of sussing out and dialing one's own ambition? How have you experienced that?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
If you think about existing companies that do aspects of what Granola does better now or may do in the future, what are the ones that you think about the most of if you were a VP at one of these companies, like you should be worried about major disruption that's coming?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
My guest today is Chris Pedrigal. Chris is the founder and CEO of Granola, an AI-powered notepad that transcribes your meetings and enhances your meeting notes. Chris shares fascinating insights on how humans have historically developed tools to extend our cognitive capabilities from writing and mathematical notation to data visualization, and how AI represents the next frontier in this evolution.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
If I was forcing you to put your like mega dreamer hat on, set aside feasibility as part of your consideration in this, what do you dream most about tools being available five years from now, 10 years from now as tools for thought that we kind of opened our conversation with?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
We explore competitive dynamics between model providers and application builders, and Chris shares his vision for AI tools that make us better rather than replacing humans altogether. Our conversation covers the product philosophy behind Granola, the challenges of building in this fast-moving AI space, and how small teams are creating outsized impact in this new paradigm.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Mickey Malka, the great investor, has an art installation that does what you just described, whereas you talk in the conference room, it visualizes what you're talking about. It is quite distracting, I will say, in a good way. You sort of can't look away from it. It's just so mesmerizing.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
But to extrapolate that, which is, I saw that six months ago or something, these things get better at an alarming pace. One question is always, what are these models bad at? Everyone's very bullish. Everyone's very excited. They're great at a million things. They're going to get better and better. Everyone, I think, is coming around to that.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Is there anything that across the model generations you've been surprised that aren't getting better? Things that they just don't do well and consistently haven't done well that are real limitations?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
What advice would you have for investors? You've raised money from great investors and I'm sure talked to a ton. Most investors in the technology world and in private markets are mostly or entirely focused on investing around this wave of AI technologies.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
And so I think they're all trying to answer the question, what is the best, most productive way to interact with company founders and new applications and all that? I'm curious what advice you would give to those people that are trying to do their best job of allocating capital to the highest and best use. What would you tell them?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
And maybe the way to answer is like, what are the best investors you've encountered done with you? And what are the worst ones done that we could avoid?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Please enjoy my conversation with Chris Pedrigal. Chris, I thought a fun place to begin our conversation today is with some of your ideas around the value of tools for thought that technology has given humans over the centuries. Obviously, you're building one of those tools. Now we'll get into that in great detail.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
If I forced you to build something else in this space, Granola ceases to exist, and you're not allowed to build Granola 2.0, what's your instinct on where you would go get into explore mode?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
What's hard about education? What did you learn building Socratic that you'd caution others building in that space or encourage them?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Can you imagine a successful tool that doesn't have a data advantage, either unique data that it has access to or first party data like you've built, where as a person uses it, they're building a data set basically that's custom to them? Is it possible to imagine like a data-less AI application that is nonetheless still very successful?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
But the first time we chatted, I was so intrigued by the way that you approached this and thought about this unlock of value for people. And I think he used the XY plot as like a good example of one of these tools for thought. Maybe you can just riff for a while on this line of thinking and why you're so interested in it. I love this topic.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Or do you think data is just an absolutely critical component of sustainability and edge?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
It's like... I think about this a little bit like music. I would be surprised if in the future, everyone just has all their own music. I think there's some shared consciousness, shared experience thing that matters for how good something is. In the same way, like there's a social proof thing or something like the wine studies where the label and knowing how much it costs makes it taste better.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Knowing how popular a song is might make you like it more. And maybe something similar applies to software. Of course, I don't know, but it seems hard to imagine that everyone's going to have the will and interest to build their own version of an app versus just being lazy and clicking the app that everyone else uses that's not entirely perfect for them.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
But I don't think everyone's going to be an app builder in the future because not everyone's an entrepreneur now. With Stripe Atlas and cloud providers and like all these things, it's massively easier to be an entrepreneur and not everyone's an entrepreneur. That's what I think. I think the future will often be lots like the past.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
And it's really exciting because I can't wait to build some stuff with it. That's my tendency. And other people have different tendencies. I don't know. We'll see. Thankfully, people like you are building this stuff that's going to make it possible.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Another question it brings to mind is just, we talked about earlier, the small team meme, how many people are going to be required to build very big businesses. Can you imagine a world where Granola has a thousand employees?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Is that still going to be, I mean, it is a thing objectively, like there's plenty of AI companies that have big employee bases, but for you specifically, maybe are we entering a zone where there could be a $10 billion company that has 20 employees or something like that? I think so.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
This has been so much fun. I'm so interested in what you're building, how you're building it. I think it's such a great example of new things that are possible and how those are being built in this new world. Thank you for doing this with me. When I do interviews, I ask everyone the same traditional closing question. What is the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
How do you think you're the most different in terms of like how you think behave than you would be had he not done that?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Maybe it's bullshit I'm telling myself or it's something someone else is saying. It's in there a lot. Maybe in closing, how does all that translate into how you articulate the why behind building Granola?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
A beautiful place to close. Chris, thanks so much for your time. Thank you, Patrick. If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
You can also subscribe to Colossus Review, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Maybe just talk about that transition. Mention what you're building at a high level first, and then we'll go into it much more detail later. But as we transition into understanding what new tools are possible built on top of this new technology, how are you personally approaching that?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
What were the original things that you thought of when you saw some of these LLMs walk us through this phase change?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
How does that manifest? Is it that everything in my life, like everything I've read and conversations that I have, everything is ultimately stored. And then there's some mechanism for me feeding my current context back to some system and it serves up ideas or brainstorm concepts. Make this a little bit more real in terms of your vision.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Maybe talk about how you work differently than others, having been the person most exposed to granola. Like, what are the actual behavior changes so far? And then I want to ask about the 5% to 100%. But starting with just the 5% penetration, how has it most tangibly caused you to behave or work differently?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Maybe now talk a little bit about that 5 to 100 of the vision of what this could become. I know you can only think a couple steps ahead with LLMs, but thinking two, three steps ahead, where do you think this goes next?
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
I'm curious for some of the nitty gritty issues that you've encountered so far. Like one is just the recording aspect. How do you think the world will evolve and how do you handle it today where it seems to be becoming more and more normal that someone will ask to record a meeting and at first really turn me off and now it's just become normal.
Invest Like the Best with Patrick O'Shaughnessy
Chris Pedregal - Building Granola - [Invest Like the Best, EP.412]
Do you think we reach a point where the assumption is just that everything is being recorded? And I know Granola handles this very thoughtfully. Maybe you should explain how you do it, but I also want to know where you think it's going.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
How did you do that? Did you have $20,000 and say, here's $20,000, let me invest in your company? What was the literal conversation and mechanic?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
What starts to congeal to get us into like the more investor brain and investing chapter of your life? Was that a feeling like, wow, this is something I want to do over and over again? What changed in you?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
So going back then, you mentioned two attributes about him, which was that he was both not going to blow up. He was like in control, but like audacious and aggressive. Maybe just say a couple more clicks of detail about, if not those two attributes, try to describe that encounter a little bit more, what you saw and felt.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
I'm assuming you held the investment for a long time. I'm curious if you've continued to hold it. What I want to know about is what it's like to hold something like that. And we can talk about this in the crypto context as well. Lots of mutual friends that were early in Bitcoin. One notable thing I see often is that they were quite wealthy to start. which made it easier to hold.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Whereas those that this was the first time they were having some smash success. At some point, if you're up 100X or something, you just sell. You've made so much money. And then that costs you a huge amount for not having held longer. So have you held it?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
And if so, what did you learn holding something like that where the value is like beyond any reasonable expectation you could have put on it at the start?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
What's the multiple on capital?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Yeah. Is that weird knowing that maybe you've made your best investment ever?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Yeah. I'm curious what they are. If I went one through five of the five most successful investments that you've ever made, how many of them shared in common some felt sense of like the energy signature of the person of the way you described? Go on. And maybe list what they are.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Yeah. Give us a sense. What do you think the four other most important investments you've made? So I don't have a spreadsheet.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Can do it on Vibes.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Okay, so let's go to Pure Investor chapter and Sequoia specifically. So tell me how you got to Sequoia. What is the bridge story? And then I've got lots of questions about the formative experiences there.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Thinking back on that time, how many years were you there? Four and a half. In those four and a half years, what changed? If I talked to you the day one and the last day, what was the treatment effect of Sequoia on you?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Does an anecdote stand out, a personal one, of you feeling that the group or a specific person making you feel like, oh God, I need to do better than I did?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
What do you do differently as an investor when the objective function is the next Apple and not a billion-dollar company that we forget about?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
There's so many incredible investors there when you were there, and obviously a lot of them are still there today. They're very different from each other, which is going to be a big topic of our conversation, like this idea of a collection of mutants or something that I think you've done exceptionally well at Paradigm.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
What do you think are the keys to creating a group of people that are extremely different from each other, very heterogeneous, but making sure that they're working really well together?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
I want to go back to two key parts of the timeline. The first is your original encounter with Bitcoin and crypto. And then the second related is your decision to leave Sequoia and start Paradigm. Maybe start with the first one. Similar question around like the TikTok thing, like how and when did you first encounter it? And what did you see?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
And I want to just introduce the word legibility right now, which is going to be like, I think, a big topic of our discussion in general. Bring us back to that. What was legible? What was illegible about Bitcoin when you first saw it? How did you first see it? Just like tell us about it.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
So what was the moment, assuming it was when you were at Sequoia, that you first thought, I need to make a bigger bet on this ecosystem and ultimately led to you starting Paradigm with Fred?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
One of the often repeated things, if you ask people about you, is they'll say, oh yeah, Matt's the one partner that left Sequoia that they really didn't want to lose. Ground that for me. What was it like to tell them that you're leaving? Did they try to keep you out of the work?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
So finally, we get to talk a lot about Paradigm and crypto and everything that's happening in the world today. Paradigm today is a $10 billion plus asset manager focused on crypto. Maybe talk through what is it? How do you conceptualize what you want it to be and what it is like a high level overview?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Yeah. The original chapter of Paradigm is so interesting because I think you raised hundreds of millions of dollars and effectively just put it all in Bitcoins. You tell that story because it worked out quite well.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
How much did you raise? What was the initial couple months of action?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Yeah. And that was like, to orient people, like $3,000-ish Bitcoin, roughly?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Does that feel like the right size? That's a size I hear a lot, that when you breach that amount, it ceases to be a team and becomes more of like a structure. You mean the 10 or 11? Yeah, the 10 or 11. Can you imagine it being 20?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
My guest today is Matt Huang, co-founder of Paradigm, a leading crypto investment firm with over $12 billion in assets under management. Before launching Paradigm in 2018 with Coinbase co-founder Fred Ursham, Matt was a partner at Sequoia Capital, where he led many of the firm's crypto investments.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
What is happening that's builder and research activity that is very clearly like not investing activity? What would I see if I came in and sat and looked over people's shoulder?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
One emerging story here that I'm realizing is you as a remarkable personality type on top of all both team asset class returns. You're in a unique structure that's kind of like a long term structure. But the daily marks on crypto have been completely insane. Can you talk about that experience? So like you mentioned the numbers earlier, if you just look two points in time, money raised money today.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Wow, amazing. 12x or 13x or something ridiculous. I'm curious what the painful sides of that have been, both on the team and on the performance. So it's a super volatile asset class. You've got like a high variance team. It seems like you were this incredibly sturdy calm on top of both those things.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
It is widely reported that Michael Moritz called Matt the only regrettable loss in Sequoia's history.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
But I'd love to understand like the hard, painful parts of that for you across the history so far, both team and assets.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
In our conversation, Matt shares his framework for navigating the often illegible frontier of crypto, how his early investment in ByteDance, now worth 10,000 times his initial capital, shaped his approach to identifying exceptional founders, and why he believes so deeply in crypto's long-term potential.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
What was the largest peak to trough drawdown that you've experienced? I don't know. Do you know when it was, if not percentages?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Say a bit about it. What was going on? What did you have to do? Did you feel caught off guard? Was this kind of like, ah, you know, another one of these? I've lived through five.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
If I were to somehow isolate the best criticism of Paradigm, what do you think it would be? What critic saying something about Paradigm would you be like, oh, fuck, that would actually land?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
What's gone the most wrong in the history of Paradigm?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
His firm Paradigm not only invests in many of the leading companies in the industry, it also builds open-source tools used by most of the crypto world. Matt has a rare blend of IQ and EQ that allows him to understand technical complexity, bring together unique talents, and ride out crypto's notorious volatility.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Was that the point of peak personal stress for you in Paradigm's history? You seem like kind of unflappable, but.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Maybe we can go into great detail on this concept of legibility and the relationship between legibility and what you mean by it and investment opportunity. I know there's a topic like you felt a lot about. Can you just let us in on your thinking on this? Why is this topic interesting? What do you mean by legibility? How does it relate to investment opportunity?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Whether you're crypto curious or crypto skeptical, I think you'll find his perspective valuable. To learn more about Matt and Paradigm, I highly recommend reading our Colossus Review profile about them. Our managing editor, Dom Cook, spent time in their San Francisco office learning everything he could about them.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
It reminds me of that amazing What's the author's name? James Scott or something that's seeing like a state book. A hundred percent. My memory of that book is the top down desire to make something understandable perverts the thing. So you plant trees perfectly in a line. One generation of trees are great. But like all the complexity that was happening in like an organic forest is lost.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
And like the second generation of tree doesn't grow by oversimplifying something that's not meant to be or even just like the way cities are laid out. Should they grow organically bottom up or should they be designed top down? It's really hard to design a great system top down is like one way to remember that book. Does that book sit in your consciousness on the topic?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
You can find that excellent profile on our website at joincolossus.com and in the show notes of this episode. Now, please enjoy my great conversation with Matt Wong. If you think about chunking your life up into early chapters, let's say up until you're like a professional, what are those chapters? What happened during them? Why would you segment it that way?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Is some of this an appreciation of what I'll call product optionality, where the world tends to interpret what might be possible with a product through the lens of existing markets and not appreciate the ways in which a new product or platform technology just creates things that we can't imagine and that a lot of the return comes from that unimaginable part?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Is that the reason why illegible things might produce better returns?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Let's apply this topic to today. Ground us in your worldview of crypto right now. How would you describe it to someone that doesn't follow it?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Let's just linger for a few more minutes on Bitcoin as money. Why is that important or interesting? What's its market cap today, like north of... Just under $2 trillion. So let's say it's one of the biggest companies in the world in some way, but money separately.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
It feels like if you stacked it up to like Amazon and Google and Microsoft and the other multi-trillion dollar assets, it's like the most maligned... Ever. It doesn't feel like, aside from maybe Satoshi himself or herself or whatever, themselves, it has these sterling champions along the way. There's some shady champions or shady characters along the way.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Why is it valuable or interesting that we have it from your perspective? Basic question, but seems important to get your answer on.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Do you think that it's valuable as money or just as a store of value? Where money implies a means of exchange, a unit of account, and a store of value.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Do you think that the Powell and Fink and their ilk understanding of it as digital gold is like extreme legibility and therefore the available return in Bitcoin itself relative to some other options is quite low? It's sort of one in some sense?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
So let's go to the second basket, the programmable financial system, I think is kind of the term used. So if Bitcoin now is still young, but more mature, like people probably most people have like somewhat legible conception of it as digital gold or whatever. What about stage two of a new financial system? Where are we in that story? What's possible today? What gets you excited?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Just your commentary on that. And then we'll go to the most illegible part of the frontier.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Yeah. Stablecoins are so interesting because it's like a perfect control experiment. It's a dollar. It's not meant to replace or be better than or outperform a dollar. It's just a dollar. So really what it is in some pure sense is like the technology part, the programmability, et cetera. So what are the key core features of the technology?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Now that we've abstracted away like a price consideration, what are they? What's about them is so important. What does the industry structure look like of stablecoins?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
What's a good example of a creative way that you've seen stable coins be used that wouldn't have been possible in traditional finance?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
It like self-settles. Yeah. Based on the outcome. Yeah. If we shift into the third gear, what feels to you like the most fringy part of crypto today? Now, everyone's heard of Bitcoin. Lots of people have heard of, especially listening to this, have heard of stable coins or use them. What do you think most people listening either won't have heard of or won't use, but you are interested in?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
When you see something like what's going on with AI and you've built a firm where the mission is push the crypto frontier forward, how do you weigh the temptation of, wow, here's a new enabling technology, a general purpose technology? Maybe we've had 25 of these in human history. Here's a new one. What if this one's bigger than the one I'm working on?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
And not wanting to go jump feet first into the biggest enabling general purpose technology. Is that like a consideration that you've had?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
In the chapter one, what is the first time that you remember being consciously aware of this family directive?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Can you give us your perspective on comparing crypto to other technology infrastructure build-outs that you've studied historically and the kind of boom-bust nature? I'm thinking here of like Carlotta Perez.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
The fact that there's speculative manias could actually be a great thing because it lays capacity for the next generation of entrepreneurs to build on, whether that's fiber in the 90s or something. And it seems like for a while, crypto had so much influence incoming interest and builders. And a lot of that was driven by the very public pricing of the underlying assets.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
And a critic might say, look, this thing's just a casino. It's unregulated gambling on ideas. If you compare today's pipes and infrastructure in crypto, I'm like a couple of years stale on this, I'm realizing. And I remember being super interested in all this, the detailed technical stuff in the last cycle. And then this cycle, I kind of lost touch of it.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
And I'm curious, has the speculation brought sequentially higher and more valuable infrastructure? Has the boom-boss been a good thing in the traditional sense of boom-boss cycles? Or is it something different in crypto because it's just so speculative at times?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
The answer to this is sometimes easier when you get away from the U.S. and these things have become very useful, whether it's El Salvador putting its treasury in Bitcoin or cross-border payments or store of value in places with hyperinflation. I really want to press you on your view of the mission for Paradigm.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
and its support of the crypto ecosystem and what I'll call like the unfinished business. You personally and probably lots of people on your team are now at the point like you don't need to do this. Sure, maybe you earn great returns. It's pretty clear to me that that's not your motivation. It's a byproduct of the work you're doing.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
And you talked a little bit about the mission of pushing this crypto frontier forward, but I'd love to get more into asking why, why that matters to you, how that answer has evolved over time. what the why is today relative to what it was in 2018. I'm sure lots of things in 2018 you might have said maybe have happened.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
You even said some of the things that have happened you would never have predicted, governments using it in treasury, et cetera. So orienting today, beginning of 2025, why? Why are you doing this? What's the point?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
I like your framing of us looking at China and thinking one thing and not looking at art. Can you detail that a little bit more? Like, in what ways do you observe financial economic freedoms being under attack or duress in the West, most notably?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
I love the answer. Connecting it back to you and the team, what is the story behind why you personally care so much about this? It's a great answer if I read that answer without an attribution, but yeah, it makes sense. I never feel like the people really pushing the frontier as you guys have and are trying to do, it's not enough that there's a good rational answer.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
What is the story behind why you believe everything you just said so deeply?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Where did that come from? What early authority figures gave you that? What experiences of authority do you remember as potentially questionable?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
If I can bring your whole team here, the investment research team here, do you think that any of them would have a drastically different answer on their motivation for why they're devoting their lives to pushing this specific frontier forward?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
What are those most essential, what are the primary colors of those interactions, the way that people coordinate?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Aside from meeting your wife, what was the most memorable day at MIT?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
If you think about your Walmart analogy of all these security technologies that come together to enable Walmart, which is like this amazing thing for the world, what missing pieces, where are we not yet secure that you wish we were that maybe crypto could solve in like the more near term?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
I want to talk about regulation and I guess politics as it relates to regulation. How would you describe the state today of how crypto is regulated? What do you hope changes? What might change? I don't have a good enough sense other than it's drastically different how the public talks about this, how governments talk about it. It's the financial firms, Larry Fink's of the world talk about it.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
We haven't gotten Jamie Dimon yet, but maybe we will. What is the state of regulation, especially here in the US from your perspective and maybe a touch on global as well? And what is its trajectory, do you think?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
If you think about the idea of custody, it's such an interesting issue for me because early in crypto and my exploration of it, there was always that phrase, not your keys, not your coins. Like if you're not self-custodying the Bitcoin, let's say, to keep it simple, it's sort of defeating the purpose of the thing itself.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
So if you're keeping your money at Coinbase or something, you're not really participating in this radical new system. But it just seems like the tendency of humans is towards more centralized custody and the I want to be able to call and yell at JP Morgan when something goes wrong. Like, I don't want to have to be the one that deals with it. And what if I screw up? I want a throat to choke.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Can you talk about custody and like how you think about the spectrum of what's important and what it should be?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
So this has been incredibly fun. Thank you for doing with me. I know this is not a thing you like look forward to doing, but I feel I've always known what's going on with paradigm just from afar. And I feel like I understand it so much more now and you, and it makes me much more excited to like the next five years of things I see you guys do.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
I feel like I'll have like a appreciation for how that might've happened, which is so cool. My thing is just finding people doing their life's work. And I just feel that this is it for you. or at least has a high potential to be. And so thank you for doing it with me. My traditional closing question for everyone is what is the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts. You can also subscribe to Colossus Review, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
I remember reading Paul Graham. There's these moments or these windows that can get open for you to what might be possible. Walk us through what happens next in your mind and literally what you're doing with your time.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
Tell us the story of the failed startup, the rite of passage.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
If I could somehow go back to that time, whatever the last day of that chapter was, and ask you, Matt, what is your worldview? What do you think you would have said at that point?
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Matt Huang - Investing At The Frontier - [Invest Like the Best, EP.420]
I have this visual in my head, like somehow what we were doing here is making a movie about you. The opening scene would be like you landing in China on a plane in this 2012 trip. And that would be like the opening vignette. Can we like do it in audio that way? Can you go like in crazy detail and tell us about literally in as much detail as you can muster this pivotal trip? We'll give it a shot.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Everyone's very focused on LLMs and their derivatives and things built upon them. Are there any other new technologies that you are watching, like you're watching those core models as they roll out that you feel like are enabling of what you do or what you hope to see others do?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
What about like technology advancements and tech trees is the term we were talking about before I hit record. What WebGL represented and why it was such a big deal and the nature of the incrementality of this one?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
What do you think about the role of these fancy reasoning engines being plugged in to make your product better? There's this abstract idea like, okay, now we have a reasoning engine. It can do whatever. We can use it to do some stuff. How do you decide what stuff to try to have it do to make the product better? What's the framework for which you attack that opportunity?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
I think that's probably true elsewhere, exposing the tree as a general idea.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
And also use case. Does it worry you the notion that these things could get so good that you already mentioned the thing about the designer and the product manager. But if I imagine a perfectly designed, funded competitor whose only mission in life was kill Figma, that they would approach this as it's going to be the same thing. But the thing you design in Gigma works.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
It's a fully functional app at the end. All the underlying code is written. It's not just a prototype. It's a live production app. Is that a ridiculous notion? Do you think that will happen? Could Figma just be the one that does that? How do you think about that brain-stretching possibility where everyone's a software developer now?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Are there things that you're counting on happening that you expect to happen that you think to the average person would seem outlandish? Dyson Sphere by 2100.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
What about in the next 10 years? Is there anything that you expect to happen in the next 10 years that you think other people might think is like outlandishly bullish or something?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
If you were giving like a graduate level seminar presentation or something on the future of design, how would you think about structuring your slides? Built in Figma, of course.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
I'll keep trying.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
If I did like an 80-20 analysis of design principles in the 80, what are the most important things to really grok and understand for someone new to the discipline?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Do you find yourself curious about the next layer of non-flat digital screen design interfaces? How do you think about the other potential spaces in which we might interact with systems? And I guess that would be radically different design environments.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
New patterns, like now I'm annoyed if something on my phone doesn't work the way that I'm used to a hundred other things using it or something in a similar design pattern. What do you think about new interfaces? Are there any that are interesting enough to you to spend some real time thinking about? I love new interfaces.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Are there any like dark patterns in all this that have you concerned or parts of this proliferation that you're worried about?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
I've never heard that term before. So maybe I'll be like the late majority on the BCI or something.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
What about in the traditional current AI world? Is there any part of that proliferation that you think is really important for us to watch carefully?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
How we deal with these problems?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Seems like the historical lesson is really bad things will happen and then we'll backfill protective mechanisms. The protective mechanisms will come from a response to bad things happening and public outcry or just some version of that. I don't know. That seems to be the pattern of history. Very rarely do we thoughtfully design it ahead of time.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Do you feel your competitive juices flowing in any different way in the last year plus of these amazing new technologies relative to times prior? Does it kick off anything new in you? Like the role of competition in your motivation and life?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
You mentioned at the beginning that you've been using the O1 Pro a lot more personally. Is there anything that you've used it for that you think is most novel to you or where the output or interaction has most surprised you so far? I'm trying to like collect these things and then share them with people to just get them trying this stuff. Anything in that category come to mind?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
I'm really interested by your point about our standards for these things already being much higher than any reasonable human, except maybe like the number one person in the world in the field that you're querying about or something like that. Does that mean to you that we're already past all these benchmarks of intelligence, general intelligence, maybe even super intelligence?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Do you care about these things at all? Are they just stupid things?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
It seems to me that there's always been an incredibly high return on vision, drive, and motivation for people. Inertia reigns unless those three things come together and someone pushes something new into existence. These things aren't, at least to my understanding, not driven or motivated.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Does that mean that the returns to those things go up in this world and that people should just focus on the areas where they're the most energized, motivated, and driven? How do you think about that part of this equation that progress happens through those things and these machines don't have those things?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
What this far into Figma still is the most motivating to you? I think everyone sets out to like build the default platform and you did that. It's now the thing that people put on their resumes. Hopefully your post resume soon, maybe that's motivating. But what are like the really hot burning core fuel sources for you still, despite having built the platform of record for your world?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Where was that rooted in your life? Were you wired this way? Did it kick into gear when you were young?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. Invest Like the Best is part of the Colossus family of podcasts, and you can access all our podcasts, including edited transcripts, show notes, and other resources to keep learning at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Big moment for you.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
When you think about your role now at the business, you're a CEO, a traditional CEO, like there's lots of stuff you have to worry about. How much do you force yourself to just do this stuff where you have special energy and farm out other things versus it's my responsibility to own like the different stack, different parts of the business because I'm the leader of the business?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
If you think back on the business's history now, it's been around for a decade plus. What has gone the most wrong in the business's history?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
If you think about the next chapter of Figma, however defined, I'm curious what chapter title you would put on it and a little bit of a description of the chapter.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
The thing I'm inspired by or make design bigger than design is, to use a personal example with the AI tools or whatever, I've never made a recipe in my life. I'm not a cook. I suck. But with these tools, I'm able to say, here's kind of stuff that I like. Here's ingredients I like. Here's what I have available. Here's how much time I have. Make me a recipe.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
I can express a lot of intent and context. And then I have a recipe that I make that I really like that no one's ever made before. Like I didn't think of the recipe, the thing did. But it seems like maybe there's an analog in design that in design, I have never designed software applications, but I have lots of intent and context and desire and constraints. Is that the right way to think about it?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
That like maybe Figma might make someone like me expand the market by making me a designer?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Are there any other trends around design that matter directly or indirectly to your business that you're most on top of and curious about in the world right now?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
I'm so curious to think about the whatever, one, three, five, 10 year hence versions of what you might make possible for people. I'm asking like speculate here just for fun. How long do you think it is until someone like me can effectively work with Figma to create the thing in my head with more or less complete fidelity?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Like I don't have to compromise on what I'm imagining to get it prototyped on the screen or something like that. with basically no design training or talent?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
What's it like building with these things, with AI tooling?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
How much of good design do you think comes after the initial draft? All of it? All of it.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Anything that you would leave people with in terms of a challenge to like go try some of this stuff? One of the things that I feel like you're always at the forefront of thinking about trying this stuff, you're like an edge tinkerer and are always aware of new platforms, new tools, new trends, and that so much of the power of these things is just giving them a try.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Is there any favorite way that you've prompted friends or relatives or whatever to just get involved as a tangible way forward?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
I was thinking about our conversation this morning and looking forward to it and how cool it must be for you to think about all the things that have been created with the platform that you created. Like what a cool. It's amazing. And that the era that we're entering maybe or have been in, but this era of new general purpose technologies that enable people to make stuff.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
My guest today is Dylan Field. Dylan is the co-founder and CEO of Figma and last joined me on Invest Like the Best in 2020. A lot has changed since then, and we explore the evolving landscape of design and how Figma has been navigating AI while staying true to its founding vision of eliminating the gap between imagination and reality.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
without having to ask for your permission. That must be a cool feeling for you to have to look back on and to look forward on to Spread Design Beyond Designers. I'm thankful you did it. And it's so fun as always to catch up and hear your view on the world. Thank you for your time. Thank you. If you enjoyed this episode, check out joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
There you'll find every episode of this podcast complete with transcripts, show notes, and resources to keep learning. You can also sign up for our newsletter, Colossus Weekly, where we condense episodes to the big ideas, quotations, and more, as well as share the best content we find on the internet every week.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Despite Figma's incredible success in becoming the default design platform, Dylan remains deeply motivated by helping users achieve their goals. He shares fascinating insights about the underhyped aspects of AI reasoning capabilities, the future of design literacy, and why he believes truly great design will always require human craft and creativity. Please enjoy my discussion with Dylan Field.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Four years since we did this last, which is completely nuts. Terrifies me. I'd love to just get your state of the union on the world of technology today. What are you thinking? Like, what are you paying attention to? What do you think's going on?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
The waters that you swim in include lots of these most ambitious people pushing those frontiers and windows. Can you say like a click more detail about what it feels like to engage with those people relative to like the marginal entrepreneur that was talented that you met in 2019 or something like that? How do they feel different?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Do you feel like that was something that you had really harnessed in the early days? Because I know it was like three or four years that you were building before you launched. Maybe take us back to then. That's a decade ago-ish.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
I'm super curious about the hardest parts of building something in private for so long without tons of open market feedback on the product or pricing feedback or whatever. How you keep a team motivated when you have a strong vision for what something should look like, but you have to build for a long time before anyone can see it. That seems like a lot.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
There's a lot of those projects going on right now.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
One of the things that obviously distinguished Figma early days was this leap in ability to create things, like the gap between one's imagination and a realized output was collapsed by Figma. And the way that even the friction for how they used that tool in the browser was collapsed.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Again, it feels like you're in a very interesting position in that the enabling technologies that are coming out right now in and around AI most specifically are like this on steroids. They are further collapsing the potential gap between one's imagination and a realized output. How do you think about navigating that
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
As one of the people running one of the big companies that does this as a service, both the opportunities and the risks, it must be such an interesting time for you to think about both sides of the equation. And I would love to hear about both of them in whatever order you want.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
Was that literally the founding?
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
I'm curious what you've experienced that makes you feel that way.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
How do you think about the ability to continue to bet on things which won't change in an era of hyper change? What can you hang your hat on that will still be true five or 10 years from now and build around reliably versus worrying that two iterations of the model forward, everything that Figma does becomes like a prompt and I can just like talk to 05.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Dylan Field - Designing The Future - [Invest Like the Best, EP.407]
And there's a little screen and it just gets built, not just the design, but like the whole application. You start thinking about this crazy stuff. How do you navigate that strategically?
Invest Like the Best with Patrick O'Shaughnessy
Gustav Söderström - How Spotify Thinks - [Invest Like the Best, EP.424]
Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
And then you start making progress.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
It's funny to imagine a future where there's an arms race and the counterfeiters are injecting their own
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
God, the mind races with applications.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Crazy. That's wild.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
So if I wanted to go through that process and said, I want to create my own, what are the building blocks of that process? I guess I could start to describe, I like plums, and I like fennel, and I like this. Is it that simple? It can be.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Well, I'll describe what our mission is and maybe it'll come out of that. So our hope would be that by finding frankly people like you, that are in pursuit of what we would call their life's work. For you it might be giving computers a sense of smell and all the applications that are born from that.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
That we, by showing people these great examples of people really doggedly on the hunt to build their thing, they'll wonder what their thing is and start building it. So I would say very focused on business and investing. Those are the forms of art that I like.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
But I would hope that our work encourages more people to chase their thing because we're showing them such great examples of people like you chasing theirs. And really just give them permission to do so. So what do I hope it evokes? Possibility. Like I think of open air. Maybe it would be like a smell that I think about. The Sequoia Parks or the Redwood Parks in San Francisco.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
When you get to the top, there's like a very specific like crisp smell.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
How long do you think it will be until there's literally something sitting here that the feedback loop is more or less instantaneous?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
It seems based on all this that it's not that long from now that you will enable things that traditionally have scents, candles, detergent products, whatever, infusers, because they're all based on the essential oil that you're delivering. That like people will be able to design scents very soon. Absolutely. So that we are rolling that out.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
If this company is going to be the thing that sort of has your name written all over it and that you're the most proud of having created, what are the earliest seeds of that story in your life?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
When you think about building Osmo the business, how do you think about the trade-off between creating a pure play platform defined as you enable, I'll call them developers, to build any sorts of application they want on top of Osmo's root level capabilities, all the things we've talked about.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
And, you know, you charge them a platform fee and, you know, lots of platforms out there that are wonderful businesses versus like, okay, we have the platform, but we're also going to create the generations, the vertical application companies on top of our own raw tech capabilities. What are the trade-offs of one approach versus the other? Are they mutually exclusive?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
I remember the Gramercy Park Hotel so distinctly.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Yeah, familiarity.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Teach us just a little bit about smell itself. What's its history? Why is it so important? Why is it so emotional? Why are scents so memorable?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
So if I think of generation as the creation of and manufacture of any smell that I want, with sort of no limits on the possibilities of how I could use that scent in a product, in a space, in a showroom, in a whatever. What are the other next two, three, four things where there's a big stack of potential utility that would be unlocked because computers can smell?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
I think of like dogs in an airport or something like that.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
My guest today is Alex Wilczko. Alex is the founder and CEO of Osmo, a science and technology company giving computers a sense of smell. He set out on a mission to digitize our sense of smell, and he describes how Osmo is teaching computers to both read and write scent.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Last time you and I spoke, we were looking up together on our computers the market cap of the fragrance houses. They're quite huge companies. Yeah, they're big. Maybe you can describe why they've been such good businesses, the margin profile of these things. What is it that makes fragrance, just in the publicly traded ones that you can go check out, relatively big, good businesses?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Alex was kind enough to walk me through the laboratory, which you could watch in the video version of this interview on YouTube and Spotify, where he demonstrates the method to their madness.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
If you think about the things that could go wrong on this journey of yours.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
I'm sure you do. What do you think gets in the way?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
We discussed their first commercial application, a new brand called Generation, which is revolutionizing the fragrance industry by dramatically accelerating the typically years-long process of custom scent creation. We discuss all the potential business implications this technology unlocks, applications ranging from counterfeit detection to health monitoring.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
One of the things that's so interesting to me about Osmo is It is an AI company in a very strict sense.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
But it's quite distinctive in the sense that most AI companies, especially building, I'll call these applications, are remixes of a lot of the same stuff. There's a lot of traditional code involved. There's software involved. There's... you know, putting things around the incredibly powerful reasoning models that now exist.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
And the whole world is kind of, I saw the other day that ChatGPT now has 400 million monthly active users, like 5% of the world's population is using ChatGPT. So people are now familiar with these language models and these generative models. But this seems like you're using the power much differently.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
And I'd love you to just kind of describe some of the ins and outs of that as we think about other problems where we can apply AI that aren't just text generation, image generation, video generation, that aren't pure generative in that sense. and pure software and get into some other world. So maybe here it's chemistry and AI.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
But maybe describe like how you're using the tools and how you think about the growth of the capability of those tools and how it will impact what you do.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
and creating a cutting-edge proprietary platform in a historically routine industry. Please enjoy my conversation with Alex.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
How much of the tooling do you use? Like, are you tapping models from the major model providers or anyone else? And if so, how?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
What excites you most about the frontier that you're exploring that you have to sort of hold yourself back from spending time on because you're focused on the things you are?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
So they're literally going through
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
One of my favorite concepts behind technology platforms is that it's very hard to predict what people will use them to do. And it seems like every time you digitize anything in technology history, crazy stuff happens that we can't predict. And I'm sure that's going to happen here too.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Osmo's young, not that old. Can you describe the story of what you would define, like the defining moment so far in the company's history? I think on the...
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
I think what you're building is singular, very unique. There's no company that I've really encountered quite like this one. And what I find so cool about it is that it's taking advantage of the technology that everyone is so excited about. So thanks for letting us in today. It's been an incredible experience seeing around.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
I can't wait to see the next iteration of the smells and of the factory and of all the machinery. When I do these, I ask everyone the same traditional closing question. What is the kindest thing that anyone's ever done for you? There were...
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
It's a wonderful way to put it. The little moments where people say yes. Great place to close. Alex, thanks so much for your time.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts. You can also subscribe to Colossus Review, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
The smell is so remarkable and it's like it wafts and changes. It's so cool.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
What is the first set of building blocks for doing that? So you've got like the individual, I don't know, isolated smells or whatever. How do you create the digital footprint for each one of those things?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
system so how much does the individual atomic unit of smell differ from the combinations like if i think about like the color like primary colors or something these are primary smells that's how i'm thinking about it is it pretty reliable like how you can combine those things into some new set of things like yeah what is the periodic table equivalent or system
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
How much will this machine change in the next five years if you're successful? Like, will you be building your own version of this? I see Gentech on there. It's not, you know, an Osmo machine yet.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Do you yourself have an abnormally good sense of smell?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
By turning it into a liquid first or just directly?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
And so I understand like the strategy behind all this. So you've got the ability to read and then you've got the ability to write. And that in so doing, that's just the first step to giving computers a sense of smell. We'll talk more later about all the applications that you could then build on top of that capability. But is that how you thought about it?
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
That to give computers the capability in the first place, it's read and write. And write is especially important because it confirms whether or not it's being read correctly.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Can you talk about the measurement of the fidelity gap between read and write? Like if I give you the plum,
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
and you stick it through your machine and you read it in and then and then you give me the oil essential oil on the other side how how you measure the gap between the smell of one versus the other and how close you are yeah it's like i'm simplifying but i'm gonna hand you the real and recreate it and you're gonna tell me
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
We were just with a very famous Hollywood person who said in the eighties, they tried to do this in theaters where they would have something that like puffed out smells.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
Yeah. And it just didn't work.
Invest Like the Best with Patrick O'Shaughnessy
Alex Wiltschko - Giving Computers A Sense Of Smell - [Invest Like the Best, EP.415]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Okay, thankfully it's not.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Can you riff a little bit on how all of this change and this frame of thinking makes you think about individual employees inside of an organization and what they actually cost? The simple thing would be they cost $150,000 of salary and benefits or something.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
But I think you're thinking about this in some new ways, which is beyond just hard direct costs and is more holistic from the company's perspective related to the customer. Talk about the cost of an employee and how that's changing.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Are there companies that you know well enough that you would say are exemplars of doing a great job of the senior team spending lots of their time on what's good for the customer?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
What do you make of this inversion of that old trope that the race was between startups getting distribution before the incumbents got innovation? When back to the small team meme, like everyone's posting about cursor and companies like it that are growing zero to a hundred million of revenue. with 10 to 30 people in a year.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
And actually, what's interesting is that, I mean, you can debate how much better Cursor is than whatever, a big company's copilot or something, but they're getting distribution way faster than we've ever seen before. What do you make of that? And what does that tell us about how the future might unfold?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
It's becoming popular to say be an AI first or AI native company for startups. It's kind of obvious what that means. What does that mean for a 10,000 person public company that sells software or provides a service or is a white collar-ish company or something like that? What would you recommend those CEOs literally do? Not like a mindset.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
First 100-day presidential plan, we're going to become AI native. What does that mean?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
What would you say to a leader that said, okay, I get it. This is cool. I love using chat GPT on the weekends. I get why this is interesting, but I'm scared that I'm going to like pivot my entire battleship of a company in this new direction. And it's a wild goose chase. It takes longer or things change too much and it doesn't actually work in production use cases. And
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
I'm going to waste my next two years chasing this thing like I'm going to chase the metaverse. There's no there there. And I show up and it's just like it was a waste of my time and I screwed up the company as a result.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
And I'm willing to eat years to wait and see where these things get and where the equilibrium settles out and wherever that Jeffrey Moore third cat, not early adopter, not early majority, like the next one. I'll be the one of those and I'll be fine.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
One of my favorite points that you wrote about and that you and I have talked about is whether or not you're treating these things like you would a genius that just joined your team that has the capabilities. Forget six months from now, like just the capabilities that it has today. If that person showed up at your office and you're paying them, how would you treat them?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Are you treating these models and their capabilities in the same way? I love that thought experiment. Can you flesh that out?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
I love Tyler Cowen's idea that most of his writing now is for AIs, not for humans, that he is generating context that will make them better for him in the future. I hope that there's more and more ways that make it easy to do that.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
I think lots of people that are optimistic about this would very quickly opt into something that generated more context in an easy way, low friction way for these things to work with. And I love that idea. Think about context and how much you have already and how much you're building. as part of preparing to use these things really well.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
I also really like your idea of the difference between a world-class predictor and a world-class reactor. Can you talk about that new dichotomy?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
What do you think you would have done if you zoom back, you pick the moment, to the most intense operational trenches that you were in at Instacart if you had this set of tools back then? What do you think that would have been like? How would you have used them?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
We've talked a lot about the role of status before in all things. Apply your ideas about status and our status seeking nature and behavior to this new world.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
How are you changing your investing as a result of all this? Whether that's the way you look for companies, whether that's the way you underwrite a company, whether that's attributes of a founder that are changing. Some of these things are the small team meme companies. If you look at the price of the equity, the valuations that they've raised at is it's high.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Nominally, they're growing insanely fast. It's hard to know what they should be priced at. Are you changing your valuation expectations? What are all the ways in which you think you're actually approaching things differently than you did two years ago or something?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
My guest today is my good friend, Ravi Gupta. Ravi is a partner at Sequoia Capital and also the host of Glue Guys, a podcast on the Colossus Network that discusses both business and sports. I wanted to have him back on Invest Like the Best to discuss a recent essay of his that he called AI or Die.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
You get to sit literally at ground zero of the community of people that are investing in these companies. Probably could be well argued that any company raising is going to Sequoia first or amongst a handful of firms that they're going to first and would love to take their capital if they could. You get this complete tip of the spear view of into this world.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
If the class of investor in Silicon Valley draw a radius around your office is wise to this, does that mean that maybe the better way to make money as an investor is to be like a private equity investor in New York that just appreciates this more than your peers do who aren't in the center of things? They don't watch cursor happening?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
As someone with incredible operating and investing chops, Ravi believes we're entering an era where the constraints that historically limited small teams are dissolving, creating unprecedented opportunities for those willing to embrace change aggressively.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
What should board members do? This seems actually like potentially a really big problem. If you're a public company, well-paid board member, maybe on some prestigious company, a lot of these roles are not hyperactive in influencing the business and they're sort of governance bodies that sometimes don't do much. What is the risk and opportunity set right now for board members of these companies?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
We discuss why traditional metrics of corporate success like headcount and process adherence may become liabilities, what it means to be a world-class reactor versus a world-class predictor, and how magic per employee and organizational agility will emerge as crucial measures of value creation. Please enjoy my great conversation with Ravi Gupta.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Are there any other conversations as you've processed this change that most stand out as interesting, notable? What other conversations have you had that most impacted you in the last, say, three months?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
So Ravi, a couple of days ago, you sent me a draft of this really interesting essay that you wrote called AI or Die, which is such an interesting framing for something that I know you've been thinking a lot about and have been thinking more and more about in a crescendoing way in the last few weeks and months.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
I love the story Shane Battier told you about his career training when he was young and this idea of the ghost. Can you relay that? Because I do think it's, as an analogy, an interesting way to think about what's happening here.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Right. I think it's helpful to think about what's happening from both directions, from both the lens of opportunity and the lens of risk. And if you think about the title of your post, AI or Die, I think one represents opportunity, the other represents risk. Even the story about Shane, two sides of an interesting coin. Maybe in closing, talk about the optimistic side of this.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
I know that this is your primary takeaway, that this is... a tremendous opportunity for the right kind of people. And then it will lead to lots of fascinating things and products and companies and careers. Maybe just try to put a bow on this for us. You've thought about this a lot now. You're talking to these founders every day. You're working with the investors that get this the most.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Can you just start by describing the process of arriving at this essay and like what precipitated it? And then we'll talk about all of its various implications.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
What's your summary of this entire exploration?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Our mutual friend Sam Teller, one of my favorite people, has this line that always has stuck with me, which is, if you just see excellence in people at the highest level, it's a huge competitive advantage because you just have this bar that you can walk around with and compare things to and make better decisions and work with better people.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
And it's all about having seen the highest level of excellence that you can. I feel like my takeaway from your post is that actually we've democratized this. We've all had a chat GPT aha moment experience or several amid journey experience, whatever. And the imperative that I take from your post is we actually should all not rest until we've created one of those in our business.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
We should have a moment that wows us. in our own product in the same way we've been wowed by some of these incredible original products. And until then, we shouldn't rest. And then we should keep going. And I just think your writing is such a cool call to action for an exciting wave of the market and the market economy and companies. So thank you for writing it.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
And thanks for outlining with us today. Absolutely. Thank you for having me. If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
You can also subscribe to Colossus Review, our quarterly print, digital and private audio publication featuring in-depth profiles of the founders, investors and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
So maybe talk about what you mean by AI or DAI in its most kind of intense form.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
So since you first had these couple aha moments with your friends at those leading edge companies, what have you personally done differently to try to respect this faster than you thought pace of change?
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
I want to dig in a little bit more to that imaginary spreadsheet you envisioned earlier, which you said market cap, number of employees, NPS.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
If your only thought exercise was trying to find a single target for a company to go, like you could have a activist help you and have a hostile takeover of the company or something and install yourself as the CEO with the goal of maximum value creation or something using this new tooling.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
Talk me through how you would process that search, trying to find that single company that could be most positively impacted if they embrace this, back to AI or die, and maybe will die if whoever's running it doesn't embrace this rapid pace of change.
Invest Like the Best with Patrick O'Shaughnessy
Ravi Gupta - AI or Die - [Invest Like the Best, EP.411]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
So if you think about those rounds that you led, I always struggle with you a little bit of trying to understand, and I guess it's just the answer is both. If you're a more founder-centric investor or a more business model-centric investor, but I'm sure at different stages of those eight rounds- you were investing for different reasons.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Is that often the case that at some point you might be backing really just the founder and what they're capable of at other points or really focused on the unit economics? Is every single investment idiosyncratic in that sense?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Because I don't remember a conversation with you about a company that didn't include pretty hardcore quantitative angle, but so much of I think what's made you successful is you've backed some of the best founders. And so help us square light, what matters when?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
So in coupons, just to close out that case study, over how many years, I guess, from the first one through to today, so the whole time, did you invest, but how much did you invest in each round? How much did you end up owning of the business? Bring some meat to it.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
bought more shares, maybe two or three of the years. I want to get into your deep belief in growth, not just from an investment standpoint, but from an almost deeper economic or even philosophical standpoint. Why do you care so much about the concept of growth? It seems like that is the thing underpinning all of your behavior.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
It seems like one of those things like, oh, high is good. When is it not? Just referring to the hidden costs of really high growth.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Do you have a favorite anecdote or story of a company growing really fast from the history of Green Oaks that kind of makes that point?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
I want to come back and really talk in detail about this process. I like the way you framed it, which is this search for the next potential S&P 500 company and that everything else is a footnote. And there's all those famous studies about whatever 4% of the company is delivering 95% of the returns through equity history. Just seems like that's just always been the case and probably always will.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
How does that impact how you run a first meeting with a company? What are the sorts of things going through your head when you're wondering from the start, can this be a company that everyone in the world has heard of and used? Because these things all start small.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
How do you evaluate that question, even at the series B or C or whatever, versus if you were just saying, is this company going to make me a nice return, but maybe it's never going to end up in that list?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Is it true that you are doing pretty much the first meetings almost every time with these founders?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
That is strikingly different than the industrial complex of private growth stage investing that has emerged around you in the time that Green Oaks has been alive as a firm. Maybe highlight all the other ways in which you feel you and your process is the most different from what has emerged as the norm way of investing for your peers, let's say.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
One of the coolest things about GreenOaks, I've seen the reports, I've talked to you about companies, and so I've seen it firsthand and know that it's true, is the sheer amount of information, like you said, that you gather on a company, even before you meet them. How has that process evolved?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Talk us through that machinery, because it's very distinctive relative to other firms that I've encountered. When I call you, you tend to know more about the company than anyone else that I talk to about the company, which sounds very non-scalable in some way.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
If your customer is one of these 10 people each year, it sounds like one of the guns in your grandfather's store, not mass manufactured Smith & Wesson or something. So how do you do both of those things? How can you have so much information? about these companies and still have it feel to them like artisanal or something or high touch, where it's you in the meeting, it's not some junior associate.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Like the two seem a little bit at odds, but I've seen the work, so. I don't think there's any secret to it.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
In this process, are there common negative things that you hear about people that actually excite you? Yeah. Oh, man.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
What have been the hardest moments in building GreenOaks, the firm itself? You said before, none of these companies are up and to the right. There's always these existential moments. Have you had truly existential, scary moments in GreenOaks' history?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
the legendary internet businesses are being built and we're going to back them. Did it feel that simple at the time? I want you to tell the D shot 10 cent story at some point. There's like a key moment of realization, I think, for you and your history.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
But was that the gist of the story that this new enabling layer of technology is getting digested by the global market and that's going to take 20 years and we're going to back that?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
just to set the initial fertile soil or whatever. Tell the story of being with D.E. Shaw and encountering Tencent and what that episode taught you.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Today is a special episode. My guest is Neil Maeda, founder of GreenOaks Capital. In 2012, at age 27, Neil left D.E. Shaw to start GreenOaks with his friend, Benny Peretz. One of their first investments was in Coupang, a South Korean e-commerce company led by founder Bom Kim.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Neil was so convinced of Coupang's potential that he invested 40% of their initial $50 million fund into that one company, a bet that eventually returned about $8 billion. Over its first 13 years, GreenOaks has backed legendary companies like Figma, Wiz, Carvana, Stripe, Discord, Rippling, and Toast, generating over $13 billion in profits with a 33% net IRR to LPs.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
How do you process AI? Do you sit with Benny and team and think through, okay, you talked about yesterday, the genetics of the model companies just weren't good when you first encountered them.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
How do you do that on an updated basis to make sure that whatever opportunities emerge because of this technology, like you're most on top of, do you form some core view on, are you obsessively looking at like the benchmarks when deep seek R1 comes out? Is that the sort of thing that you're doing?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Henry Kravis, one of Neil's early investors, describes him as extremely disciplined with exceptional timing who has gone against the tide many times. GreenOaks operates with remarkable concentration, just 55 core companies across nearly $15 billion in assets, managed by only nine investment professionals.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
I'm curious how you would characterize the changing nature of competition. So you're not the only person looking for these 10 outstanding people every year. There's other really talented players in this game and on this playing field. When they meet one of these 10, I'm sure lots of them move heaven and earth to try to be the partner of choice. Early on, you probably faced less competition.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
They were less industrialized, this industry. How has that changed over time? What have you had to do to have your win rates stayed as high when you want to win? If they have, what have you had to do to keep the win rates as high?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Their approach reflects their singular pursuit, finding companies that will become a meaningful part of the S&P 500. In our wide-ranging conversation, Neil shares this mission along with his framework for identifying exceptional founders, his concept of jaw-dropping customer experiences, and how his grandfather's gun shop in India shaped his appreciation for builders of all kinds.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
I want to get as far into this as you possibly can. Again, I won't name specific firms or names or anything, but really, really, really drill into why it's less competitive today. Because naively, I would say it's different. The supply demand. And if I just think about, okay, there's a unit of transaction here. Some cash is going into a business for equity in that business.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
The supply-demand dynamics of how much supply of cash there is for a limited amount of equity in great businesses has gotten way out of whack relative to when you started. There's way more cash.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
So naively, you might say it's way more competitive. And the expected returns, to your point, used to be $35. It doesn't need to be $35. Now it's $15, and all this cash is driving down that return. Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
So really walk me through in lots of details why the nature of firms, who's leading them, the partner at those firms, all the dynamics that happen to make it possible for your statement to be true, that it's less competitive today for you than it was 10 years ago or so.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Once you've heard directly from Neil, I highly recommend you read our in-depth profile of him. Neil gave our editor-in-chief, Jeremy Stern, unprecedented access to his life, investment philosophy, and the work that has made him one of the most successful and unique figures in modern investing. The outcome is a brilliant profile about a phenomenal investor.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Do you care about the enterprise value of Green Oaks? No, not at all. Zero. Zero.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
If you think about the ways most recently that you've improved your craft, What comes to mind even today versus two years ago? What are you doing better today than you were two years ago in this craft of finding and courting the 10 best each year?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Find the profile on our website, joincolossus.com, and in the show notes of this episode. Now, please enjoy my excellent conversation with Neil Maida. I think I have to ask about your grandfather first. Yeah. Whoever taught you the artisan craftsmanship of gun making.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
The ability to write a $500 million check, maybe we should tell the Carvana story at this point or something. Move really fast in real huge size on something that you're not going to have a full written memo about. You have to act quickly.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
It seems like that's a great answer to your earlier point about it being less competitive because you could probably rattle off the other investors that could do that same thing today without an investment committee meeting or without this, that or the other thing.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
I remember the Robin Hood story that Mickey Malka from Rivet told me, which rings like a similar, you know, it's like a guy making a couple calls to make something happen. Maybe talk a little bit more about that. Carvana could be the example here, but pick a different one if you'd prefer. I'd love an example of weird, high conviction fast that would be impossible in a committee structure.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
I'll give you three. Great. Two more.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
It's like the Bob Kim story a little bit. It rhymes with it.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
As you go back to the early days, you had this first fund that was so successful, huge multiple in money. How did you decide how much money to raise in subsequent funds all the way through to today? This is constantly a question for every investor ever that's been really successful.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
They tend to have the opportunity, you certainly did, to raise probably as much money as you wanted to raise, given your past results. How did you choose the amount through time? How would you teach, if you're Kravis giving money to the next you, what coaching would you give them on how to answer this question?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Have you ever thought about other structures for Green Oaks, like making it some sort of permanent capital base, like Berkshire Style or all this creativity with Apollo and Athene, like having some sort of insurance? It seems like every great investor reaches the point in their career they want an insurance company for a permanent capital base or a balance sheet.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Have you ever thought about that side, the asset side of the business of where the money comes from, how it sits and its structure?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
I'm so freaking glad I asked about that. You're in one of these positions where if you wanted to, you could just do this with your own capital. I think you're the largest LP in the funds. You've had the success that all the investors chase. Why still have outside partners? You've made that choice, obviously. What is it about working with great LPs?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
I know your LP base is super concentrated to very consistent theme in your life that you're really concentrated. But having achieved the level of success, it could just be your balance sheet could be the holding company in the Berkshire and make the marginal investments. How do you think about that trade off that choice?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
If I were to do a great, complete, anonymous, ubiquitous survey about you and Green Oaks, and I were to find the critics to the extent that they exist, what do you think they would say?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
What do you think the greatest of all time is?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
They make fun of his PowerPoint slides.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Well, I'll tell you the answer that most people give, which is Moritz.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Can you tie the feeling of that appreciation for the craftsmanship to what you do now? Is there a direct line? Do you think that had you not seen those guns, was it that impactful, that early appreciation for craftsmanship, or would you have come to it a different way?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Since we're at the end of a long session, I'm curious to hear a little bit about where your instincts for understanding the world have brought you outside of investing. Are there other places that you apply this same instinct where your curiosity pulls you into a world where you're not investing huge sums of money?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Mysterious investor.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
You say you don't like any of the attention. Is there any kind of attention you do like? You've walked the walk here, by the way. I'm so excited to do this with you, but something tells me this is going to be the one you do and then see you again in 10 years or something. You've walked this walk of focusing on the work, which makes me curious.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
I think that's actually a really interesting and compelling place to wind down. I love that, that you don't want to get attached to things that fundamentally what you've done at Green Oaks is always search for the next person, even if that person's bomb over and over and over again, which is so cool to have these special relationships.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
You know, the last question I ask everybody, what is the kindest thing anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Neil, thanks so much for your time. If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts. You can also subscribe to Colossus Review, our quarterly print, digital and private audio publication featuring in-depth profiles of the founders, investors and companies that we admire most.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
Could you describe this acronym JDCE that I know is a key part of the early Green Oaks story and it's something I'm sure you still think about a lot and maybe pick an example and go as far down as you can on what made for a JDCE in a company or product that you were evaluating?
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
When you think about BOM and a person like that, that you met early, I think you led five of the eight rounds in Coupang. Maybe tell the investment side of that story. So that's what BOM is doing for one aspect to create this incredible, loyal customer and fan base. Meanwhile,
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
You're doing something very differently through Green Oaks, which is typically a company like yours would invest, maybe lead the series A and participate in the rest of the rounds on 5% or something at IPO. The way that you've always done it is very different. You're very, very concentrated. Maybe just talk about a step-by-step, the five of the eight that you led.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Neil Mehta - Finding Future S&P 500 Companies - [Invest Like the Best, EP.419]
So how much did you end up owning? Talk us through the numbers and the position. And this is an investment case study. Obviously, it's an important one for Green Oaks, but it's indicative also of the kind of investing that you do and how it's different from other firms of your type.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Sorry. So just so I understand that one, which sounds incredibly exciting, I could get tested blood work or something else or genome or something, some combination of things that's unique to me. And then a vaccine would be created to reduce the odds or eliminate the odds that I would get the cancers I'm most prone to get.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
I see.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
So going back to this, what sounds like a or the key bottleneck, which is that we just don't know how to predict whether or not something will work. Can you break that down further?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Because I'm trying to wonder if there's a version of the future where it does become easier to simulate, model, predict more like an engineering challenge versus a complex biological system challenge that we can't predict. Practically or theoretically, what is in the way of us predicting things better and therefore drastically improving the efficiency of our efforts?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Could you just describe the basic investing process? for you when you're looking at a company and a product? Because I know it's quite distinct from me looking at an AI software application or something. What are the key variables that in most investments that you're analyzing, you're looking at? Is it typically just a team that's going after one specific target or one disease?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
What is the nature of an atomic unit of an investment or an investment diligence process?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
It sure makes me wonder the role of capital, which is not rational, whether that's government or otherwise, that's willing to fund things that sound like that vaccine story that you mentioned, where you're not going to get the appropriate readout until phase three, and it just doesn't make sense to provide them with capital.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Sure makes me wish like someone in the world, whether it's philanthropies or otherwise, it was intentionally funding things that are irrational explorations. That's an interesting takeaway from your summary.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
If you were to think about the changes in general that would most accelerate our ability to identify a target, understand a disease and create a therapeutic. It sounds like it's some mix of if we could somehow test these things, not in humans, but in simulation would be one big one. And that just like the healthcare industry itself would need to change in key ways. Do I have that roughly right?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Like those are the two things that most impede our ability to go faster?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
One of my favorite books that I read last year was For Blood and Money about the development of two cancer therapeutics. And one of the takeaways from reading that was a story in which the primary investors made incredible amounts of money. But the story was quite chaotic. The things that had to go right were many.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
And many of the bounces of the ball seemed just kind of crazy and random and impossible to predict. And sheer persistence and a lot of luck and a lot of factors had to come together for that group of people to make a lot of money. And a couple of people were a few degrees away from making a lot of money and made very little.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
I'm curious, with stories like that seemingly all over the therapeutics world, what the best therapeutics investors do that bad investors in therapeutics don't do? If there's stories like that happening everywhere, it's tempting to think you just have to get really lucky versus be really good. So what is the combined role of skill and luck in making money as a therapeutics investor?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. Invest Like the Best is part of the Colossus family of podcasts, and you can access all our podcasts, including edited transcripts, show notes, and other resources to keep learning at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Obviously, you're part of one of the most central medical episodes, certainly in our lifetimes and also in recorded history in the development of that vaccine and rolling it out. What is your postmortem on that whole process? I think parts of it are exactly what everyone wishes, which is something happens and we're able to with technology.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
and a prepared platform in mind address it incredibly fast. There's all the stories about how quickly the vaccines themselves were developed. And then most of the time delay was just testing them. That seems amazing. Everyone wants more of that. Then there's been maybe a hangover of side effects of the vaccines, which I personally don't understand any great detail. I'm sure you do.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
And we all wanted these rushed because we wanted to get back to our lives and to not have loved ones die. And I would just be curious. This is such an interesting real world experiment of moving very fast. to address a huge problem, what your post-mortem analysis is of the whole thing having been at dead center of it.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
To learn more, visit psum.vc.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
My guest today is Tal Zaks. Tal is a physician-scientist turned biotech executive and investor who served as Moderna's chief medical officer during their COVID-19 vaccine development, giving him an extraordinary perspective on one of modern medicine's pivotal moments.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
His combination of medical expertise, platform innovation experience, and investing acumen allows us to explore the interconnected challenges of turning scientific breakthroughs into viable medicines while generating venture-scale returns.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
We dive deep into the lessons from Moderna's mRNA platform, examine how emerging technologies might reshape drug development, and the fundamental question of what it means to make a healthy person healthier.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
For investors, entrepreneurs, and anyone interested in the future of medicine, this discussion provides a window into both the immense potential and profound challenges of advancing human health. Please enjoy my conversation with Tal Zaks.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
It's an incredible recounting of a crazy episode in our history. I like your balance take a lot. Obviously, it's above my pay grade to have some long, drawn-out conversation on the pros and cons of these things. But I do think it highlights how complicated and nuanced all of these issues are when you really start digging into them.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
And it makes me wonder a little bit about the future of applying these platforms to other things. Maybe we won't have something on the scale of billions again, maybe ever in our lifetimes. Maybe we will.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
But as you think about something like an mRNA platform, and I'm curious what other, I'll call them technologies or platforms like mRNA, you think are the most important to address disease in the future. What do these things now enable for us? You were eight for eight. That's so cool. But eight is small.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
What do you think the future is of, let's start with mRNA specifically, and what it will change about the way that we deal with our health in the future?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
So Tal, maybe to begin, you could give us your one minute summary of your career, just so people have context of where you're coming from in all the incredibly interesting topics that we'll get into today.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
I wonder if you could... This is meant to be a little bit fun, and no one will hold you to these predictions, but if we think 5, 10, and 20 years hence, to pick three time periods... what sorts of things you think may be happening or possible in terms of the way a single person manages their health. And as an example, I've always been interested in this idea of
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
fairly constant ongoing data collection for myself on blood work or scans or genetic information or whatever input data that might help identify things early, suggest ways that I live a healthier, better lifestyle. I think basically everyone wants to live longer and better. And today that's incredibly crude.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Maybe the best in class people get their blood work once a year and pay attention to it and know what it means, but like almost nobody does. How do you think that general state of how people approach this problem will change in that 5, 10, 20 year timeframes?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
My kids are 10 and 8, so they're young and they're going to be the beneficiaries even more than you and I are of so much of this science and discovery and research and product building. Do you think that their adult lives, that they'll look back on this time and think that it was almost barbaric how we... discovered, identified, and dealt with disease.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Is that degree of radical change coming that we might look back on pre-vaccines or something and just think, can you believe that people would die from this stuff? How crazy is that? Infectious disease and otherwise, which no one dies from anymore relative to the past. Is that change coming, do you think? I'm thinking the 20-year, 30-year horizon now.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Well, your intersection there of investing and deep science and personal hands on work and as a physician is exactly the Venn diagram that I've been searching for to have this kind of conversation, which is really about the current state and potential future states of medicine therapeutics.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
It reminds me to ask another investing question, which is what investors of your type most consistently get wrong when underwriting therapeutics investments specifically? What risks do they consistently care too little about, too much about? As we said before, it's a hard area to earn a return. There's huge potential returns available because the market's all of humanity.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
What do you think investors like you get wrong most consistently?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
And the investing returns that might be earned from paying some special attention to those areas, which I think is the key distinction between the therapeutics themselves and the potential for returns. Maybe you could give us the equivalent of a state of the union on that topic of how do you see the world today of medicine versus maybe your career?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Like if you compare today's snapshot to everything you've seen across your working career, I think that would be a great place to start just to give us context of where we are today.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Do you think it's possible for an investor who's incredibly talented in lots of traditional ways, but not formally trained like you are as a physician, as a scientist, as a medical professional to earn great returns investing in this space? Or should it just be the domain of people like you, that have deep domain expertise?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
My penultimate question for you, given that it's the one on everyone's mind, I'll try to think of a unique way of structuring it, is the impact that AI is going to have or might have on this field, just writ large. And maybe the way to think about it would be your bear case, your base case, and your bull case for the ways in which AI models may affect the world of medicine from this point forward.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
What does that mean? What is inroads in a thin vertical? Just bring that to life.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Do you think there's a world in the bull case category where biology becomes engineering, that we're able to run simulations in digital twin humans, not in real life clinical trials, and therefore we're able to iterate at a speed that's impossible in the real world and solve all the problems? This is a utopian take on how AI will affect drug discovery and therapeutics and medicine and health.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Is that possible? It feels like if it's possible, we're going to get it on some time horizon because of how fast technology is evolving. But I'm curious if you even think it's possible.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
Tal, this has been such a total blast to learn from you today. I ask the same traditional closing question of everyone. What's the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
If we could all do that for one other person, it feels like the world would be a lot better place. Tal, great story. Thank you so much for your time. Patrick, it's been a real pleasure. Thank you. If you enjoyed this episode, check out joincolossus.com. There you'll find every episode of this podcast complete with transcripts, show notes, and resources to keep learning.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
You can also sign up for our newsletter, Colossus Weekly, where we condense episodes to the big ideas, quotations, and more, as well as share the best content we find on the internet every week.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
What is your assessment of the potential for the world of therapeutics to explode in a similar way as what we're seeing with artificial intelligence and some other areas of technology? And I'm curious to ask you this because you have exactly the right balanced perspective of an excited investor, I'm sure, but also a practical realist from your time designing and rolling out drugs.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
at Traditional Pharma and at Moderna, which is a very neat platform that we'll talk about. What do you think is that potential? Should we be excited for a thousand flowers to bloom and an explosion of progress in therapeutics? Or do the realities of incompleteness of biology mean that it will be slower than the most excited people think it might be?
Invest Like the Best with Patrick O'Shaughnessy
Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]
To learn more, visit psum.vc.
Invest Like the Best with Patrick O'Shaughnessy
Kelly Granat - Investing At Lone Pine - [Invest Like the Best, EP.414]
To learn more, visit psum.vc.
Invest Like the Best with Patrick O'Shaughnessy
Kelly Granat - Investing At Lone Pine - [Invest Like the Best, EP.414]
Like Apollo or KKR.
Invest Like the Best with Patrick O'Shaughnessy
Kelly Granat - Investing At Lone Pine - [Invest Like the Best, EP.414]
100%.
Invest Like the Best with Patrick O'Shaughnessy
Kelly Granat - Investing At Lone Pine - [Invest Like the Best, EP.414]
We are.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
It seems like such a fascinating and complicated scenario where they've released an open source model where the closed, say, anthropic and open AI type companies in the US, which have been the pioneers in this space, are saying, look, this model wouldn't exist if it wasn't for us. It is being built on top of our work. I'm curious for your reactions to IP and the ability for them to do that.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
And I have both a theoretical or ideological curiosity here and a practical one. I'm curious how you think about it through both of those lenses. Like if you're anthropic, let's say, how are you approaching this if you're running that business? What are your ideas, ideological and practical, about a Chinese company using models that were developed here in the U.S.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
with lots of capital to make the thing that then leads to this abundance for the world? It's such a weird thing to wrap one's mind around. And I just love your reaction to those two lenses.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Do you think that some of the closed source models, OpenAI, Anthropic, and any others that enter the fray end up looking more like Apple to Google's Android or something? It's very hard to know what's going on inside of Apple. It's an incredibly well-protected IP company.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
And better than this question is what you personally are rooting for, the set of outcomes that you think are best for America and for the world vis-a-vis AI.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Is there a limit to wanting max evolution speed and max competition? Perhaps if I said we know that the best things are going to come out of China for sets of reasons because they're willing to do things that we don't let our companies do in the US.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Would there be a version of this where you said like, yes, I want max evolution and competition, but the national interest at some level supersedes the desire for max evolution and speed of development?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
As always the case, these outcomes are so incredibly complicated and unintended consequences happen everywhere. I'm curious for a little extra thought on the software side. Everyone's aware of TikTok and whether or not that's going to persist as an app that our kids can use here in the US.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
But DeepSeek is another great example where it's top of the app store, lots of American people downloading it. I'm curious what you personally, again, are rooting for in terms of our treatment of software provided by China, which tells the CCP or whomever tons of information about American users and their behavior and how you think about that, again, through the practical and ideological lenses.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
How do you think all of this will affect capital allocation? I'm most curious for maybe your firm, how you think it'll affect Andreessen Horowitz five years hence or something like that.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
If I think about investing firms as some bundle of the ability to form and raise capital, the ability to do great analytical work and the ability to like judge people or something, especially in the earlier stages.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
How do you think that function, how capital gets allocated to entrepreneurs that are building the next great companies will change as a result of 07 coming out and having this incredible reasoning ability, incredible analytical ability? What will be the most different about capital allocation and investing because of all of this?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
He wants the ham sandwich companies.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
You're building one of the biggest firms in this part of the capital allocation universe. How, if at all, have you adjusted your plans and strategy for building the business in the face of this technology down to the practical? Now we're doing more of this or less of this. How have you adjusted the direction of the ship based on this new technology?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
It's so interesting to me that your firm, which is obviously a huge footprint now, is similar in some senses to like the KKRs or Blackstones of the world where you and Ben were founders, seasoned founders when you started this firm. And similar with Blackstone, I think Schwarzman had never made really an investment before starting Blackstone and look what it's become.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
And it seems like the founder approach previous founder approach to building asset management investing firms is that they build these real big, ubiquitous platforms. You've got verticals and most of the major exciting technology frontiers. Do you think there's some credence to that, that the very best capital allocation platforms have and will be started by founders more so than by investors?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
My guest today is Mark Andresen. Mark is the co-founder of Andresen Horowitz and one of Silicon Valley's most influential figures. He combines deep technical knowledge from his engineering background with broad historical understanding and strategic thinking about societal patterns. He last joined me on Invest Like the Best in 2021, and the playing field looks a lot different than today.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Are there aspects of the firm that you hope are new and different in 10 years that don't currently exist? And are there any non-compromisables, ways that you hope the firm never evolves to look more like traditional large-scale asset managers?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
I've made sure to try to listen to all of Mark's many recent great podcast appearances to make sure that we covered very different ground than Mark has covered elsewhere. He goes deep on the seismic shifts reshaping technology and geopolitics.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
If you think about the changing nature of power structures in the world, we talked a lot earlier about America, China as like Cold War 2.0. I've always seen you tweeting about tons of books studying this specific topic, transitions in power through world history. Where else do you have your eye today on power centers that are changing, either gaining or losing power that interest you most?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
We discussed DeepSeek's open source AI and what it means for technological rivalry between America and China, his perspective on the evolution of power structures and the transformation of the venture capital industry as a whole. Please enjoy our conversation. And if you haven't yet heard, last week at Colossus, we formally launched a subscription to our new property, Colossus Review.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
It's a quarterly print, digital, and audio publication that profiles the investors, founders, and companies that we respect most in more detail than we've ever gone before. To learn more, go to joincolossus.com slash subscribe or click the link in the show notes. Mark, I think we have to start at the white hot center. Can you just riff on your reaction to DeepSeek's R1?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
What were the original seeds of demise for the previous generation of elites that led to all those 11% approval ratings? What would you attribute most of that to?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Yeah, I'm a case study of it myself. If we take an optimistic lens, your emphasis on early stage venture, you get to meet all these young, brilliant people that are about to go build the future. Let's take the optimistic lens and say AI has the most positive impact that we can imagine in all the places where we can verify the outcomes. Reasoning becomes so powerful.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
What are the other related choke points that get in the way of the sort of explosive technology revolutions that we all want? That could be clinical trials in medicine or something, but just going to go slower than AI is going to go. And AI is not going to be the problem.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
We're going to have bursting at the seams of wanting to make progress, but the world of atoms or the world of regulation or the world of clinical trials or whatever it might be are going to become the rate limiters, not intelligence and knowledge. Which of those choke points have you most personally interested today?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
How did you most feel that? Like, how did you feel the elite wanting to destroy you? How did it manifest most?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
I'm incredibly interested, as so many are, by the nature and state of the global supply chain. And this is indirectly a little bit of another China question.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
But when you dig into the components of pharmaceuticals or really the components of lots of things, you see how incredibly interdependent the world is, especially the US and its reliance on places outside of the US for just supply chain, generally speaking. I'm curious how you think and hope this will evolve in the next decade or so, because obviously there were benefits.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
We went global for a reason, but I think that there are now lots of fragile spaces in supply chain around the world. How do you think about this part of the evolving economy and the economic story for, back to your point, you want the US to win? How do you think the US should and might win in supply chain manufacturing, all these exciting ideas you hear swirling around today?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
There's another lurking area of technology frontiers that I haven't seen you talk about a ton, which is robotics. Everyone's very excited by the potential. It's very easy to imagine a humanoid robot, especially lurking around doing all sorts of stuff that humans don't have to do anymore. There's tons of technological breakthroughs that are required to make that world a reality.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
What do you think is going to happen in the world of robotics? What's being overestimated? What's being underestimated? How do you think about it?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
It's been fascinating to watch the race to build not just the bodies of the robots, but the brains. Companies like Physical Intelligence and others, American-based, trying to build the data sets that we just don't have yet. We had the open web to train AIs on.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Are there areas elsewhere in all the young people you're seeing and all the companies you're seeing that you are incredibly excited about, but you feel like the market has not yet realized what is going on and what is possible?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
They're damned interesting.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Two closing questions. The first is around you and your firm having coined this concept of American dynamism and increasingly defense technology, which used to be a backwater for early stage investors, has now become an incredibly popular category, lots of capital flowing into it.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
And people are thinking about national defense and evolving war zone that has a lot more massing of drones and less soldiers and all these different changes. Is there anything in that world that you're most attuned to personally and learning the most about today?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Wow.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
So as we don't end there, I'll ask a quick final question. I love how you are always reading these incredible books and then taking from them frameworks to apply to your understanding of the world. If you could leave everyone with one book that has an interesting framework beyond the Machiavellians that you mentioned earlier, what would you pick?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Awesome place to close. Mark, thank you so much for your time.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Thanks for having me back. If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts. You can also subscribe to Colossus Review, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Obviously, this is like the least static story of all time. And within two months, this model will be stale. Other models will come out. Lots of innovation happening at every level of the stack.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
But just zooming in on today and this new paradigm that we've entered, if you were writing like a winners and losers column of all the various stakeholders, whether that's new app developers, incumbent software developers, infrastructure providers like NVIDIA, et cetera, closed source versus open source model companies, who do you view as the major winners and losers post R1 today?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Yeah, it's incredible.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
One of the things that's so interesting is immediately like the mind switches. I think you called it the Sputnik moment. One axis of comparison is the Americans versus the Chinese is a new race, not so much like anthropic versus open AI versus Lama or whatever. How do you think about that axis of competition and comparison and what it will result in? What is the Sputnik moment?
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
Maybe explain that idea and riff on that new source of competition a little bit as well.
Invest Like the Best with Patrick O'Shaughnessy
Marc Andreessen - The Battle For Tech Supremacy - [Invest Like the Best, EP.410]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
In the time that you would be in studio with Roy, what was that like? What was his affect? What was his style? What did you learn from him?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
If you think about the ability to build your reference class in art or in founders or in anything, How have you done that most successfully? It intrigued me last time we were together. You said you're going to Brooklyn a lot just to do studio visits here in New York City.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
And that you constantly are making time to meet, I think, mostly young women artists in Brooklyn lately of a specific school or style. Abstraction. Abstraction. And it just strikes me that this is something you've done over and over again that... whoever you're picking, it's not that you just met someone and liked them. They're one of hundreds or thousands of people that you've met.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Talk about like that benchmarking exercise.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
How did you convince those people at the peak of their powers, many of them, I'm sure, to take their time and do this? Like what was the pitch? What was the incentive structure? Like why did all those people agree to do that?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
There's relationships. They did it for you.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
If you think back to your checklist, your pilot's checklist and appropriate follow up to a Gulfstream discussion, what's on that list? Like, especially when you're meeting someone for the first time, especially when there's it's, you know, Alex Karp early on when there's not a lot of information about him. What is that list that you're running through in your head?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
What kinds of questions do you ask him? Like when you're digging into someone's process, how do you, what have you learned is the best way in?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Go figure. If you think now about the post talent spotting, so you meet an Alex Carp and you want to you want to work with him. Talk about what you've learned, helping and watching institutions that end up as big as Palantir has. You've been a part of lots of them in those first couple of critical years. Like what are the common ingredients? that you saw for really fast growth and success?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
I love the answer around the 50 engineers, 10-minute segments. And a common theme you see today, Elon Musk being like the prime exemplar of it, is that any ways that you can increase your clock speed, just save time, basically, get through cycles faster, seems to be defining kind of who wins. Can you just say like a little bit more about time and the respect for time that you have?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
It makes me think the last two answers, combining the ideas of time and just like executive ability of Steve Schwarzman. And I'd love to hear about the early days of Blackstone. He has this very famous mantra, which is like, what's next? He writes about this in his book.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
And he seems to be one of the, like you, sort of always dissatisfied with stasis, like always wanting to know what the next thing that we can do is that we've earned the right to do.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
My guest today is Michael Ovitz. Michael is the legendary talent agent and co-founder of CAA, or Creative Artists Agency, and he is joining me on Invest Like the Best for the second time. Michael started CAA in 1975 and over the next 20 years built it into the world's most formidable talent agency, changing Hollywood forever.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
He shares his insights into how he identifies exceptional people across diverse fields, from Hollywood directors like Steven Spielberg to tech founders like Alex Karp of Palantir and venture capitalists like Marc Andreessen. Michael is a force whose expertise extends beyond just people.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
He's also become a master in creating institutional momentum, which you'll hear in his involvement with MoMA, Gulfstream, and more. We discuss his pilot's checklist for evaluating talent, the importance of time as his most valuable resource, and why he believes maintaining excellence is critical in any field.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
It seems like momentum is such a critical ingredient in all these stories. Again, this is like time cut a different way, I suppose. But the what's next mentality of Schwarzman, the platform building, institution building of Andreessen Horowitz, the way you built CAA, the race to scale. Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
even what you're doing now with Ali at Trayville, it just seems like you have these ways of installing systems which create momentum. Like I think at one point you were running a daily fundraising meeting when you're raising a new fund, like every single day.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Still doing it. So like, what are those things?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
I would love to hear like, Yeah, just some riffs on momentum. It seems like one of the things you're exceptional at is systems for creating it and maintaining it. And I know you believe deeply in it.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
I don't ask about that.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
I'm also excited to watch Ovitz as he helps build the asset management firm Trayville with multiple-time guest Ali Hamed. Please enjoy my great conversation with Michael Ovitz. So, Michael, last time we did this, we covered so many interesting parts of your life and career and story, but we left a lot out even in two hours.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
And I thought that a common theme for today that would make it really fun is this joint notion of you spotting talent extremely early and what the talent that you did select had that the hundreds of others that you met with didn't. And then helping and watching those people build relationships. enduring institutions very quickly.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
it didn't matter what their background was that ben was a brilliant operator and mark invented the browser it didn't make any difference what do they know about investing speaking of one of your not pivots but evolutions how did you teach yourself investment banking like what was the story of getting into it why did you do it and i'm especially interested in like if you compare the first deal or two that you did to the last deal or two of that chapter how you most changed how you did that job the strategic
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
I'm especially interested in the first 10 years of institution building around some of these people that you've been intimately involved with. Maybe start with that talent piece. What is it that all these different people, who are very different from each other, shared in common when you first saw them, especially the ones that were very young when you saw them.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Bigly.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Some of them were in business school, hadn't proven themselves. Certainly the ones from my world, sort of business and investing is one batch. So whether it's Alex and Joe at Palantir, whether it's Steve Schwartzman at Blackstone, Josh at Thrive, Mark and Ben at Andreessen Horowitz. I mean, the list kind of goes on and on.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
There's also people in other fields that aren't that I'm not familiar with that you can tell us about companies that you were involved in. Like just take MoMA as an example. Everyone knows MoMA as this preeminent art institution. It wasn't always. MoMA wasn't always MoMA. There's plenty of museums.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
It's so interesting to think about the evolving business model where the underlying thing is the same, that you just are the nexus point for coordination in this entire world. What was the most fun part of that chapter of doing those very big deals?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Like, I remember the story in your book that I can't remember which deal it was, but when you netted the fee to UNCAA, it was something like 60 or $70 million at the time after you paid everyone else off. And that was just like a massive dollar amount.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
So it's probably 200 million equivalent now or something. What did that teach you? That seems like a really important moment.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
I'm very interested in like the people component of how MoMA became MoMA and what you saw and what you did and who you recruited and how. So these are all examples of kind of the same question over and over again with each of these people. But for context, those are just some of the names.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
What did he teach you? He seems just like such a fascinating, incredible.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
I have more notes from my first meeting with Herb III, maybe on my iPhone, than maybe any other meeting in recent memory.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Wow, that's so cool.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Why did you tell me one time that one of the worst things that happened to you was being the number one on that power list for eight straight years?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
I can't remember which magazine it was.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Are the moments, just to harken back to the name, all fundamentally creative in your experience?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Reminds me of Danny Meyer's Always Be Collecting Dots, ABCD. Kind of a beautiful idea.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Why is excellence so important to you? Or why do you get frustrated by people that don't live up to their potential? Kind of the same question. Because I think it's a waste.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
There's three things that you've said to me that always stand out and they're sort of in concert and I'd love you to reflect on them. One is that you're the world's best friend and the worst enemy. The second is that nothing that you do is by accident.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
And then the third was from your book, which is something to the effect of you grew up being bullied and then spent your career bullying others in support of your clients.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
I love it.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
All true. You can't make this stuff up. So best friend, worst enemy, nothing's by accident. Everything is incredibly deliberate.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
One of the coolest things I've seen of yours was the Picassos with the statues.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
We just finished the NFL season. Tell me about Roger Goodell, someone I know that you think very highly of.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Pretty cool. Yeah. If you think about your arc from agent to banker, to all these other things you did now to investor and working with so many investors, Is there anything between those sort of three categories that is most distinctive, like things in the investing world that just require something different or your approach is very different than it was in the practice?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
What do you think is going to happen in the future of media? It's changing so fast. AI is introducing unlimited content, basically.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Everything's a sequel.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
If you sum all this up, and I think about all the lessons I've learned from you kind of in closing here, I bet a lot of people would want to sign up for the sheer amount of experience that you've had, the ability to enjoy so many people, so many works of art to help create things just like the the prolific nature of how you've worked and lived. What's the North Star behind all that?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Is it happiness? Are you seeking happiness? Do you care about that word? Is it something else? Like for those that say, okay, great, like I'm optimizing for this. I can maybe live something like you have.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
I think that's a beautiful place to close. Michael, thank you for the ideas, for the stories, for everything. Patrick, it's a pleasure. I always love talking to you. If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
You can also subscribe to Colossus Review, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
What a question.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
Crazy.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
If I think about the competitive landscape, so this guy did a fantastic job for 30 plus years, updated, remade the institution, had that founder energy. Surely other amazing museums were competing for some of the same things that MoMA won and MoMA won, whether that's, you know, the works specifically, the brand, the cultural resonance, the building, like all these different things.
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
What were the things that you saw him do or helped the institution do yourself to sort of win over time in a competitive landscape?
Invest Like the Best with Patrick O'Shaughnessy
Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
If you think about the literal process of training, maybe you can explain it to people that are curious about how this actually works. So you have raw video. A lot of it has voice in it. You can start it, obviously, by translating that voice into text. But let's say you're trying to train a model.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
I like how you guys referred to many people like Asura focusing on what we'll call B-roll background video or just like a landscape of video. And your focus has been on A-roll, like a human being on an iPhone looking video talking. How do you train a model where the output is a role like that? Like just imagine a portrait video of someone reading an ad read or something like that.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
That's indistinguishable from an actual live video taken on an iPhone. What is the literal training process? What is the target of the model as it's training? How similar or different is this to just next token prediction? What's the mental model for next X prediction or something in a video? Like how do you think about the literal actual training process of what's happening?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
What does that mean in terms of the SAP on resources that video models will represent relative to text models? Like one of the big... discussions in public markets and private markets is how big do the GPU farms need to get? Are these video models to get to that point of perfection necessarily more consumptive of GPUs than text models would be?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
What's your two cents on this big question of do we need to build nukes next to data centers to train the perfect Lord of the Rings model or something?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Can you talk about the felt experience of having a business? We won't quote how big the business is, but it's very big and it's grown ridiculously fast. One of the things you hear that's a common idea now is that a new technology like this unlocks distribution. Distribution used to be really expensive late in the mature last SaaS cycle or something. People sort of had their tools.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
But when tools are just 10x better or more, 100x better, distribution for a time becomes really easy. I think you've been beneficiaries of that unlocking of distribution. Just talk about what that is like. What is it like to see revenue and users and all this stuff scale at this pace?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Because it seems like the revenue growth rates of some of these AI application companies are faster than anything we've ever seen. And I would just love you to riff on that a little bit and want to describe what it was like, but also just reflect on anything that it teaches us.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Can you level set what the platform can do today? The major use cases, like everyone can imagine feeding it a video, getting a captioned video back. That's very simple. Can you lay out the other ones and give us a sense for their relative popularity? What is the revealed preference of how people want to use a platform like captions?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Just to clarify, like in something like edit, am I prompting it to say, I want it to do this specific thing? And then is it sort of like prompting
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
So what is like the relative breakdown of what tools people use? The free versus the paid and the editor versus creator? Like, how does it shake out?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Does it feel like you're in an arms race right now with other companies?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
What are the trade-offs that you've had to choose one way or another as you build? Video is a big category. That could mean I get to make a Lord of the Rings quality movie, or it could mean something much more provincial than that.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
What are the like surprising hard limitations of what the models can do today or might be able to do in a year? Like I'm imagining we're sitting at this table, there's a bunch of stuff on the table, my specific brand of water bottle or something. I want to tell the thing to be able to like hold it like this certain way.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
And like, I want to be able to sort of direct an object that's not the person, but that interacts with the person. Is something like that relatively straightforward? Yeah, I think that will happen within six months.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
How does that work? Are you creating like a 3D representation of this thing somehow? What are the steps that go into the ability to create something like that?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
How do you think the value of these things will change over time as the cost and frictions to create them falls? Humans are really good at scarcity and assigning value to scarce things. And so a beautiful video that shows a product was valuable because it's costly to create in some sense, probably.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
How does the availability of perfect, high fidelity, unbelievable quality video at a moment's notice, how do you think that that changes the value of the video itself? And I'm just curious of like other knock on effects of what you're doing that you've thought about.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Yeah. Little Michaela was way ahead of his time.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Shout out Trevor McFetters.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
I mean, I think you can go crazy with this stuff. What are the surprising limitations of these things? What would people be surprised that they have an especially hard time doing?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. Invest Like the Best is part of the Colossus family of podcasts, and you can access all our podcasts, including edited transcripts, show notes, and other resources to keep learning at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
What does it feel like in the competitive landscape to have established something so successful and important? I love the idea that companies pass a level of maturity when someone else tries to kill them for the first time. Have you had that experience yet? I'm really curious for the sharper, rougher elbows part of building something so fast. Any experiences like that that are interesting?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
To learn more, visit psum.vc.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
What does that look like, them trying to kill you? Literally just copying the product.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
It seems like early days of all these models getting built that research talent was one of the most important scarce resources in extremely short supply. Can you talk through what you've learned about that, how it's changed? Is it still a handful of people that you really need a couple of them to be able to build the cutting edge thing?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
What is the role of extreme research talent in building the models that fuel all this great product?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
How do you think these products will price over time? This is like always the weird question with software where the marginal delivery of it costs nothing. A lot of people have been talking about, let's look at, let's say, Accenture's market cap or something like that. And it's a $250 billion company basically selling labor, very high expensive labor, important labor.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Do you think that AI applications will take labor budgets and be priced like heavily discounted labor? because that's what they're doing and replacing? Or is it just going to end up pricing like all software does? We've run these playbooks for 20 years and we kind of know how to do it.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
What's your sense of how people should think about pricing AI software applications and what its equilibrium state will be in the future?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
My guests today are Dwight Churchill and Gaurav Misra, co-founders of Captions, which uses AI to generate and edit talking videos and has grown to significant scale at remarkable speed. We explore a key distinction in AI, tackling bounded problems like video generation versus unbounded problems like general intelligence and what this means for building sustainable businesses.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
We also explore their unique data flywheel, why video generation could reach Hollywood quality within 18 months, and why building advanced AI products doesn't require huge teams. Please enjoy this great discussion with Dwight and Gaurav. And a key side note, the first person you'll hear is Gaurav.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
I think the entire world of investors, VCs, growth equity investors, public investors, pretty much every single one of them is trying to figure out how to think about AI and its implications on their companies, prospective companies, equity valuations, all the normal important questions. How would you advise them from the other side of the table?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
You've talked, I'm sure, to a lot of the great investors. You have several of them that have invested in your company. What do you think investors understand about AI? Well, what do they feel like categorically? They're not understanding as much detail as you do from the builder side. Give us your lay of the land of how you think investors are doing.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Give them a grade or something at understanding. Yeah, if I have to grade it.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
So, guys, the topic on everyone's mind, I think, is this shift from AI as this incredible technology that's decided everyone understands how amazing this is to OK, great. What are we going to do with it and how can we build enduring generational businesses with this technology at the core? You were very early in building a business that charged customers very early on using this technology.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
I love this framing of the unbounded problem nature of intelligence versus the bounded problem nature of video or some of these other things. Kind of a fascinating bifurcation.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Just you.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Scott from Cognition was the guest today. So he's building the next layer. Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
I'd love to just extend the analogy one step further to business model. Most of the commentary on AI businesses has been, again, focused on foundation model companies that have, well, have had two problems, huge CapEx outlays to train the models and then huge inference bills. So often early on, really negative gross margins just to service their $20 a month subscription product.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Inference has fallen 100x in cost in the last 18 months or something crazy. These costs are going down. But those were the two criticisms of the business model was, oh, my God, this unbounded race, I got to spend 10x every time to build the next thing. When am I ever going to make some money? It seems like this other category of more bounded problems have pretty normal, great business models.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Is that right? Is your sense that you guys are just going to have really high gross margins like a normal software company? And yeah, you have to spend money training your foundation models, but it's not $10 billion and Walk me through the business model expectation, margins, capex, things like that, what the J curve looks like in these businesses. Educate us a little bit on this second category.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Maybe you can begin by just riffing on the lessons that you've learned so far about building an AI business that are maybe distinctive from a normal software business or something. And also get into some of the open questions that you yourselves have trying to evolve your business model. I just think this is becoming the important question in the marketplace right now.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
And you're one of the earliest adopters. So you're the perfect people to answer.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
If you think about the future now, what is on the other side of the mission accomplished banner of you just did all video and you can create anything you can imagine in CGI with $100 million budget. Now you can do it in captions. Then what? What do you think you would do then?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Any major lessons from your time at Snap, which strikes me as a very unique culture and an extremely product centric, like a good place to train for product maybe. What lessons do you take from your time there and what lessons do you leave behind?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
The closing question I ask everyone in this show, it's fun to get to do this twice today. What is the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Simple and powerful. Guys, thank you so much for your time. Thanks. If you enjoyed this episode, check out joincolossus.com. There you'll find every episode of this podcast complete with transcripts, show notes, and resources to keep learning.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
You can also sign up for our newsletter, Colossus Weekly, where we condense episodes to the big ideas, quotations, and more, as well as share the best content we find on the internet every week.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
What is it like to work with video data where I imagine like just the terabytes or petabytes or however you measure it of data that you have is sort of insane. How do you think about something that might just get as good as it can get. I love the point that if you give a Hollywood studio or WADA or something enough money, they can literally create any visual that you can imagine.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
The friction between imagination and output is already gone. It's just really, really expensive. So really what you're doing is just making something cheaper. When do you think that could be achieved? I think it's pretty soon, honestly.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
Can you describe the stages that you've gone through as a company? Maybe we'll use like the Tesla analogy. One of the beautiful things about their model is the cars, by virtue of being driven, are gathering data all the time. The product itself naturally generates data exhaust. And I think you've had a somewhat similar story on the video side where
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
And so you don't need YouTube or some massive proprietary library of video to do what you're doing. Can you just describe, take us back to the day one of the business, what it was to start, why you started there and then how it's progressed since?
Invest Like the Best with Patrick O'Shaughnessy
Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
The reason I like the Graves one so much is because it's chicken fingers. Like the object of his obsession is like this sort of low status thing. I think so many people would love to build a fancy piece of technology or something very sexy as their lifelong mission or something. But in many of my conversations with you, the object of obsession is something very simple like chicken fingers.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
And I just think chicken fingers is sexy. It's such like a visceral thing. We've all eaten chicken fingers. And a man like Todd has devoted himself to one thing. I think you said on the episode, he won't even make... People wanted a sandwich and he just took his chicken fingers and put buns around it and that's the sandwich. Like he is singularly obsessed with this chicken finger dream.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
And I love the question now, what is your chicken finger dream? And chicken finger is better than something else because of almost how absurd it is. So... Tell us a little bit more about what you've learned from studying him. It was probably my favorite episode of Founders ever.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
And maybe you just hit me at the right time and I needed to hear that message right then and there to work on something for an absurdly long time, not think short term, whatever. Lots of common lessons, but what is it about? Why do you think this one is so, especially this person and this business, which is so simple and so low brow, so resonant with so many people?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
This idea of anything worth doing being worth doing for its own sake. And my favorite maxim that I've stumbled across, I think originally from Kevin Kelly, the old editor of Wired Magazine, was that the reward for great work is more work. And it seems like so much of the fastest to 100 million of ARR type thing is that the target is something that's not the work itself. It's some other thing.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
And that the healthy orientation that you're describing that Todd Graves has and all these other people have is actually just towards the work itself. And you had this really interesting notion of almost anti-business people. Yvon Chouinard is the founder of Patagonia, comes most immediately to mind. I love that book of his, Let My People Go Surfing.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
So talk a little bit more, dig deeper on this idea of anything worth doing for its own sake. The reward for great work is more work. Being anti-business as an entrepreneur, there's some depths to this that I think continue to pull at the same thread.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
What does it feel like when you find it? Because you said earlier you were 32 before you kind of stumbled on it. And then five years after that, was it like actually the full-time thing that you could do to earn a living and much more? What was the change in feeling of, what does it feel like to do the thing that you love to you? Unbelievable relief.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
We've heard that a few times from some exceptional people.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Say one click more about this anti-business, you call it anti-business billionaire so that it would get lots of views on Instagram or whatever.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
What is your own measure of good or great for your own product? That I like it. But why? Like what is it about whatever that episode was or the Todd Graves episode or like if I stack ranked your 50 most recent episodes based on the quality, your own perception of their quality, what's different about number one versus number 40? Like what's more true in number one than number 40?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Like what is the measure of goodness?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
I mean, he wrote a lot in his books about the relationship between simplicity and mastery. And that's, I mean, that's the theme of our conversation. Like it shows up over and over and over and over again. That conference you're referencing with the capital allocators, you know, you said, I don't know why I'm there. Well, I know why you were there.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Like I wanted you to go because I had a theory which was correct, which is that the people there were gonna be more interested in you and your project than, you know, the next guy's like latest great investment. And I think the reason for that is that everyone recognizes a truth in this basic message of the power of finding one's mission and then pursuing it forever.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
And I would just love to hear you riff a little bit on what that has taken for you in the last, I guess we met in 2022, so call it three and a half, four years ago, something like that. In that period of time, which is when this thing has really taken off, What are your drops of, you know, glue or like, what are the things that you've done, had to do to make this thing better?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Because I just want to keep bringing this point to life that like, once you find the thing, what kinds of things does it then take to make the thing great? So what have those things been for the last, you know, four years?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
My guest today is David Senra. David is the host of the Founders Podcast and at Dear Friend. This is our third time doing Invest Like the Best together, and we have conversations like this one all the time. In today's episode, David distills wisdom from more than 400 biographies of entrepreneurs into a single word, focus.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
I'm not going to put out something I wouldn't listen to. One of my favorite things that happens with you is someone will say something that just bothers you and sets you off and gets you going on this stream of lessons that we're talking about today that you've learned, that you've shared with people. What other things that you see people do bother you the most in business?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
If you think about the reasons that people sell a business, typically it's either because they have a chance to make a tremendous amount of money or some amount of money, or it's because they're tired of the thing, of the business, therefore of the product of the whole endeavor. Why do you think that the money thing has become, I would think about it as like a false idol or something.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
He reveals why exceptional builders like Todd Graves and James Dyson create billion-dollar empires through obsessive dedication to simple ideas, whether perfecting chicken fingers or designing vacuum cleaners. all while rejecting conventional growth timelines and investor pressures. David challenges us all to find the one thing we'd pursue even without recognition or reward.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Like it has become the unit of interest, of obsession, of showing off, of status, of all this kind of stuff. What's your theory for why this seems to have inflected like so crazily in the last decade? couple of years.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
We discussed the concept of anti-business, raising capital as a founder, and decades-long commitment. Please enjoy this great discussion with David Senron. If I think about founders and try to simplify what it is, I would say that it's an entrepreneur lives 40 years and built something. A biographer spends four-ish years researching them and writing something. You spend like 40 hours writing.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Why are the people that are doing it that way so much better at marketing than, like—
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
if you read a marketing book and you know tried to go market your product or had some marketing person at your company in charge of how the world hears about you i'm thinking about the red bull founder estee lauder like this seems to steve jobs of course this shows up over and over again that not only is the ability to create an incredible product god i love that line of mediocrity is invisible until passion shows up to exposes to expose it
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Um, such a, I won't forget that one, but the same thing seems to happen. So that's the product side. The same thing seems to happen from all these same people on the marketing side. What is the flame there that's behind that?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Like why, what have you learned about that side of, of business studying all these people where they're not only responsible for the product, but also for how the world engages with it and hears about it?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
reading the book and thinking about it and tying it to all the other lessons. And then you spend 40 minutes. And so we spent 40 minutes listening to your summary of that thing. And if you think about that incredible amount of distillation, like that's a big reason it's so interesting and so valuable. So I guess my first question is to distill it even more.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
What is it about the Red Bull? It's so unique. It's so different. It's one of my favorites that you've ever done. So...
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Like if you think about the entire project, the entire corpus, and we're forced to distill it all, all your work and therefore all the work that came before it down to one thing, what that one thing would be. Yeah, that one word would be focus.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
I asked sort of the marketing version of this question, like the nonfiction marketing, like if you believe so deeply in the thing. It actually becomes easier to sell the $600 vacuum versus the $40 one. What about on the talent side? I know you've learned a lot from Brad Jacobs and other people about the power of hiring the very best people. Everybody says that.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Everybody says it, but they don't do it. But they don't do it. So why don't they do it? What do true founders, in your sense of the word, do differently? And this is the same question I asked about marketing, but for talent.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
I love the answers on product, on marketing, and on talent. Maybe the last one is on capital. Is there anything that you've seen the people that you've studied do different or especially well when it comes to attracting the right sources and partnerships on the capital side specifically? Raising money, doing clever deals, clever financing. Is there any dimension there that's worth exploring?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
This is where I'm starting to get in trouble too.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
We started our conversation talking about focus. To conclude it, can you just define after all this study what the word founder means to you?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
It's a wonderful closing thought. So cool to think about everything you've done the last, I guess, eight years now, nine years now. I love how you close your thing by saying, you know, 400 books down, a thousand to go. There's always a thousand to go. Wonderful closing sentiment. Thanks for doing this with me.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts. You can also subscribe to Colossus Review, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
Like, why is the 50 year version of a business story more interesting than a 10 year version, which I'm picking 10 cause it's like 10 decades, a long time. Yeah.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
was essentially a fraud. If you think about the, that over 70 category of entrepreneur that you've learned so much from, what do they do most differently in contrast to the in a hurry, fastest to a hundred million ARR type entrepreneurs that you've also spent time with?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
So where does the durability come from? Like, like how do they, those long stories, how do they earn the durability?
Invest Like the Best with Patrick O'Shaughnessy
David Senra - The Focused Few - [Invest Like the Best, EP.422]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Anything really surprising from Edge relative to your expectations?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
One other component of this that's fascinating is just the way you deal with the established communities and local stakeholders that are close to where you're building or other towns, other cities, the people in them. I'm sure they have varying opinions about what you're doing and whether or not they want it nearby.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
What's been your approach to increase your odds of success by dealing with people near the project?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
It reminds me a little bit about the story in Wynwood in Miami, where the cops and the graffiti artists, once enemies, became collaborators and friends. And this crazy thing has come into existence out of that respect and reframing of a relationship. It's so cool.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
In your many travels, both in the US and elsewhere, can you tell me everything you've learned about the impact that cars have on towns and communities?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
I'm so interested by how these forces shape the places around us. How do taxes and mortgages and the history of those things in the U.S. shape places?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Go for it.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
It's so interesting to think about those incentives and how used to 30-year mortgages everybody is. Basically, everyone I know has a long-term mortgage on their home. Do you think that to snap that and create innovation in the building of new towns, those towns just need to be built with equity as a result? How are you thinking about types of financing for Esmeralda itself?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Anything worth mentioning about the way that taxes impact everything? I'm so interested by the mortgage answer. Anything on tax that you've learned that might surprise people?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
If I investigate some of your other experience and how it impacts how you're thinking about the world now, if you think back to your time as the editor-in-chief at the Stanford Review, why did you do it? What was the interest that led you to apply to do it or rise to do it? Why bother?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Another thing I've seen you write about is this notion of tools for thought and the ability to be in some sort of tight feedback loop between the tools you're using to build something and the actual creation itself. Why is that such an interesting thing for you?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Really interesting part of what you said to me, just to be really mindful of your frictions and lower friction is not always better because if you create lower frictions through the tools you use or the places you live, you're going to bias your behavior towards low friction stuff. I really thought about it that way.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
It's just like really interesting how you think about the fact that it's very high friction and very long feedback loops to building a town. But ultimately, a town is an environment to think in too, an environment for thought, not just a tool for thought, and maybe to make that connection.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
My guest today is Devin Zugel. Devin is the founder and president of the Esmeralda Institute, and she is creating a new town called Esmeralda in California wine country. Learning of Devin and her plan, I couldn't help but wonder why there are more people building new towns.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
She shares the origin story of her project, a modern reinvention of the Chautauqua community she cherished growing up, and we explore her fascinating work building communities and reimagining how we live together.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
What was it that most stood out about that town that you visited, Las Calinas?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
We discuss how environments fundamentally shape human behavior, how cost of space impacts creativity, the financial challenges of town building despite their potential for strong returns, and the plans in place for Esmeralda. Please enjoy this fascinating conversation with Devin Zugel. Devin, I have to start by asking where your obsession with places came from.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Is there anything else about your study of, I think the term is placemaking, that is strange in its origins? Is there anything else that interests you in that topic area?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
What are the ingredients of this deep interest of yours?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
I was interested to see some of the people that you've interviewed or talked to. What have you learned from Michael Nielsen? Such an interesting person.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
I know one of the things that maybe helped inspire some of what you're doing is an unconference that you helped host that brought together frontiers, people and innovators in a very cool way. What have you learned about people that thrive well at a frontier, whether that's physical, digital, mental, spiritual, whatever?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
You've sought out so many places to be inspired. What kinds of people do you seek out? I think you're very broadly curious and interested in lots of different things, but what's your taste in people that you tend to seek out to learn the marginal thing about this passion area that you've developed?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Give us a sense or a flavor of some of the things in the environment that shape you or the way that you think that might surprise us.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
It makes me wonder if part of the answer to the question of why there's not more towns is that there's not enough money in it. How do you think about the prospective returns to be earned by someone that builds a new town? Maybe there's a version of this where you demonstrate really high risk adjusted returns to the equity that goes into the project or something.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
And that becomes a model that's replicable and attracts more capital because the returns are high. So how do you think about the financial return based part of a project like this and whether or not that might be an impediment to new town creation.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
What have you learned so far about sales and marketing for something like this?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Of all the people you presented this to, I'm sure there's many with amazing perspectives. What question should people ask you more that they don't tend to ask you?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
I'd love you to just dream a little bit and think ahead however long, 10, 15 years, whether it's Esmeralda number one or there's multiple towns that you've built, to imagine the most successful version of this story.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Fantastic. This has been so much fun to explore with you. And it's been so fun to learn about separately through all the stuff that you've created to teach people about it. When I do this, I always ask everyone the same traditional closing question. What's the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
So proximity is one key variable or dimension of your setup in life. What are the other key variables that interest you most?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Can I ask you one more?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
I'm curious why you care so much about this notion of unlocking human potential. It seems like that's really a through line if I think about your thinking in tools for thought, environments for thought, Frontier Camp, all these things that you've built or been a part of seem to be about people that are curious to eek the most out of their own potential. Is that right?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
And if so, why do you care so much about that?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
What's the first time you can remember feeling an expansion of your own capacity?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
How old were you?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Beautiful place to close. Thank you so much for your time.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts. You can also subscribe to Colossus Review, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
What's the origin of your ambition to try to combine all the things you've learned about space to a very ambitious project that you're building in California? Maybe at a high level, describe what you hope to do and then why, what the backstory was.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
On a degree of difficulty scale, how hard is it to build an entirely new town? It seems so much like America is what it is. You don't hear about whole new towns anymore. You hear about very fancy high-end discovery land properties or something like that that are designed from scratch, but usually not just a normal town. Why doesn't that happen very often anymore? Why doesn't it seem to?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
Maybe you could walk us through the most inspirational places that you've been, in addition to Chautauqua, that form some of the ideas for what will be, I think you call it the hardware of Esmeralda, your new town. What are those elements? Where did they come from? I'm so curious how you decided what matters and gets to go into the project.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
If you think about somebody that buys a house there and lives there for a year, what do you hope is the way that that person describes Esmeralda to someone that hasn't been there?
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]
What things will you put there that make it easier or more fun to create and innovate together? How do you actually promote that in a town setting?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Jesse Beiruti from IA Ventures said something to me really interesting. He said, you have to decide probably whether the kind of capital you want to provide is unique, singular or not.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Meaning if you didn't provide this capital to the person, they probably wouldn't be able to get it otherwise versus winning access to the consensus, like best new thing that if your capital didn't go there, surely other capital would. But your advantage is that you're accessing a scarce supply. And I thought about that vis-a-vis you. And it seems like you did both.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
You both were often a day one investor, not a seeder in people like Dan Sondheim that were leaving and just incredible investors. And there's somewhat of a limited supply. And when the eight seed deals that you did, I think basically all of them or most of them worked out really, really well. And by definition, that's more of the former. If they're willing to give up economics, it means something.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I'd love to explore maybe like one example of each. You could pick a seed deal or you could pick an investment you made that wasn't a seed deal on a manager. We could also talk about a direct deal. But back to just understanding what you're doing and what's going on around one of these stories. I'd love to do one of each of your game.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
What about on the traditional side? Is Dan a good example?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Opportunity.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Can you define commercial? It's such an important term in our dialogue over the years. Why is that word so incredibly useful?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Was there any through line to the mistakes that you made at East Rock? Backing deals, managers, seeds?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
When you think about the moment at which you were there and Eastrock, the platform was sort of humming the most. I love that Josh Waitzkin idea that not just career, but life is like this opportunity for self-expression. I'm curious where, if anywhere, it wasn't that. I know Eastrock was a great vehicle for self-expression for you. We could talk about lots of ways that that was true.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
If you think about it and had that blank sheet of paper, Josh always talks about like going into the cave with a blank sheet of paper to come up with a new platform. Is there anything different that you would do to better have a vehicle for self-expression than played out with East Rock? Not really.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Is there a chance you're actually not lazy and you're just like applying that? Like you're lazy about taking action or hitting the hammer or whatever analogy you want to use. But it seems to me like I was thinking about the word prolific. You've written seven very well-read posts ever. Not exactly prolific in your writing output, but like extremely high impact.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
But I always wonder like, for what are you prolific? And it seems like you've read everything. You've met everyone. There is some unit for which you are prolific and maybe it's not output, but it's like your own format of thing. Yeah. So do you think that's right? That you're not lazy. You're maybe lazy from the outside looking in or something, but I don't know.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It just seems like you're always deeply tapped in and that's not...
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It's like we were joking. What was the nickname? It was something like Leverage Lion. And I was talking to Boyd because lions, when you watch them for long periods, they basically do nothing. And then they're just like ferocious around opportunity.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And the intensity level is just, I mean, you can feel in your chest when you're there in Africa and leverage because with you, I always think of that joke of the guy that charges a thousand dollars and $9.99 is for knowing where to hit and a dollar is for hitting it. And then that's sort of it.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
A lot of it can be boiled down to a handful of really great decisions that were carefully considered, obviously. But that to make those good decisions, you do need to be prolific in some sense. Like you need to have seen a thousand things you don't do.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And that's far from lazy.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Yes.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Yeah. Yeah. Say a little bit more about that. What is it about that process that's energizing to you? Is it figuring out the person? Is it something else? Is it excellence?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Yeah. You'll find it. You'll find it.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Maybe it's a great opportunity to talk about the idea of yours that's had the greatest impact on me personally, which is this notion of positive feedback loops, a person's compulsion or bliss or lots of different names for I think probably the same thing. And like the right setup that allows for this unlimited upside. Yeah. And there's lots of dimensions to this.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
There's how to help someone find this thing, what the right setup is, how to partner with someone that's doing one of these things. But each of these aspects to me is like, has been in my life an incredible unlock of like self-awareness around what my compulsion is. And then constantly asking that question, not just once, not just at the setup phase, but constantly.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Is this thing wrapped around my compulsion or is it bled into like normalness? So... You've done this more than anyone I know, thought about it more than anyone I know. How does someone start to track that potential compulsion in themselves? What does it look like from the outside? What kind of questions do you get people to ask of themselves?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
What was your second moment of ignition?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Was he the most prolific, famous cedar at the time? Yeah. And what was your sense of what made him so good at that?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Platonic ideal of this concept.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. Invest Like the Best is part of the Colossus family of podcasts, and you can access all our podcasts, including edited transcripts, show notes, and other resources to keep learning at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Yeah, of course. Is there anything you hear on those calls? I have a lot of those too. I'm fascinated by this category of call. Yeah. I love it. The want to lever. What are some common observations on those calls of like something you would hear where you're like, nope, not ready. Like what are the piles you sort people into on those calls?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I've never heard it put that way. It's so resonant. Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It's so interesting how it's turtles all the way down. Like if you hear founders fund GPs talk about what they do, it's the same. It's like they want the hair. They want any deal heat and they're gone because the price is wrong. And it raises an interesting question about seeding, which is if it has to overcome this adverse selection problem, and it has this juiciness to it.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I feel like every investor ever has had some period where they're like, we should do seeding because you're putting LP dollars in, whatever. The downside is they're a really bad investor. And I get GP economics on the other side. And it just seems like this money machine. But obviously, it hasn't been. You're probably the best seeder ever. There aren't 10 other great seeders.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
The model itself seems so sexy and alluring, but there's this adverse selection problem.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Does that mean you don't think of yourself as a cedar that just happened to be the right expression eight times or whatever, however many it was? Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Yeah. It's so interesting that working with source thing is just true. Like if you go read it and you have a high end of investors or companies or founders or whatever, like you just see it. Are there other aspects of your obsession with that and like how you suss it out that are interesting when you're trying to identify what the source is for any given person?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Today's conversation is going to make you think about your life in a variety of new ways. You should listen to it in its entirety. I first met Graham Duncan in 2017 in the offices of East Rock Capital. We had lunch inside of his beautiful library. The food was insanely good. And I remember thinking this person is extraordinarily special.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Bringing it back to something very tangible, which is this interesting matching exercise between investors that might want to run money for a family or a set of families and someone that's commercial and talented enough that it would make sense to give them some of your money. Why is there not like a YC for... That kind of person, or even a YC for like investors.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Why, if I'm new billionaire X that wants some great setup, is there not a demo day where I can meet highly talented, ambitious, hungry, low ego commercial? Well, one thing is, I think, I wonder...
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
either lend them money or they put half their net worth and you lever it some way to make it feel as though they're doing it so there's no ic because it's like the inverse of companies you want young people with raw potential who are going to go figure out some new thing yeah whereas an investing side you want the grizzled experienced veteran on average not always yeah Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
You don't need a big selection mechanism. You just kind of know who these people might be. Like it's a small pool and they're not applying to it. They're not going to apply.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I'd been a little bit nervous to meet him because his reputation was as the most discerning people picker on Wall Street. In the years since, I've been lucky to grow close to Graham, and there are not many people that have impacted my life and thinking more than he has. He's one of the most generous people I've encountered who has genuinely made me appreciate life in many new ways.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It really is kind of a paradox that you're stuck in. You really have to want back to Stewart's line of make it like a pro manager, like an amateur. Like you really want need to want to manage it like a pro. Yeah. And the BATNA is iconic. Or Jordan Park or something. They're not going to fuck it up. They're going to do a fine job. It's going to be beta. Yeah. And it's going to feel nice. Yeah.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
So be it. You have to deeply want something better than that to find that great CIO.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
There's three criteria that you've written about that like if you were hiring for a CIO for yourself or your family office or something that you've laid out that I'd love to go through each one and kind of what you mean by each. So the first one is there's got to be evidence they have good taste in people. And taste is a fun and funny word to try to define, very hard to define.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
What's your definition of it? Like, what do you mean by that? And why is that one of the three key criteria you think?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It's not an absolute thing.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Practically speaking, if you're the principal... Basically saying, like, tell me who you like. And then meeting all those people. And if you like all those people, like, probably a good sign.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Did that happen at East Rock? Was there this gravity that got created as you partnered with and backed East Rock? Was the marginal one always a little bit easier than the last one because of the gravity and the reputation that you had built?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
His profile on X reads, compulsively seeking new ways of seeing reality, and that is an understatement. Among the dozens of lessons he's taught me, one stands out as having been the most impactful. He phrases it as a question. What are you most compulsive about? Is it possible to put that at the center of your platform's activity?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Can you talk a little bit more about those events, big and small? I've been a part of that. And it has that incredible effect. If you nail it and you're not compromising in any way about who shows up, whether it's a dinner. You used to do this amazing dinner with dads, investors who were dads, to kind of talk about being a dad. But that was the frame.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And they would be very different people, but they would all be so... Great. And then a much bigger event that's 100 people that somehow also like every conversation is like, holy shit, like who are these people? How did you find all these people? And then that creates like a mystique around you. Like, wait a minute, who are you? Like, how are you doing this?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
So say more about the intentionality behind those gatherings. Seems like that is a really important ingredient in the event. Yeah. The recipe of your career.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And then it sticks to you somehow.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Can you tell the story of working with the guys who started Paradigm?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Anyone that knows me knows I'm obsessed with the concept of finding and pursuing one's life's work. It is Graham as much as anyone else to whom I owe the impetus for my own quest to find mine. As you'll hear, because he has studied people more than anyone I know, he's the perfect guide for helping each of us think about ourselves in new and interesting ways.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Graham is also fond of saying that talent is the best asset class. This is my obsession too. I want to spend my time finding the best people in the world and learning their life stories and sharing them with you all. Last year, we decided that it was time to build a new publication at Colossus that allowed us to go even deeper into life stories, which we are calling Colossus Review.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I realized that earlier we talked a lot about identifying the person that is maybe entering into their positive feedback loop, compulsion platform, whatever you want to call it.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
What we didn't talk about, which seems really important for the prospective CIO hire or whatever doing this job in general, is the act of once you've identified them, structuring the relationship with them in such a way that everyone makes money together, to use your language. What was that process consistently like? And sometimes it was seeding. Sometimes it was an LP investment.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Sometimes it was a direct deal. Maybe bring us into the room on what those processes tended to be like and what you learned about doing that second half so well, not just finding, but then ultimately consummating.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
The second thing on this categorical list, which I love so much, is a quiet ego. Why those two words?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It's a quarterly print, digital, and audio publication that profiles the people, investors, and founders that we respect most. We're launching it formally today, and to see more, you can click the link in the show notes or go to joincolossus.com slash subscribe. When we were starting it, there was no doubt who we should put on the first cover.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
The third of those criteria is that they be conservative by nature. That one kind of stood out to me as interesting.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
On the topic of investment platforms, just like hiring a CIO, you've got some of these great questions that you encourage people to ask themselves. And I'd love to go not through all of them, but just through a few of them, the ones that stood out to me.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Because I think people that listen and read what we're going to produce here, some huge portion of them are in that funny category of working at an investment firm, wondering, do I have what it takes to launch my own thing? And the first question you pose or you encourage people to pose is whether or not they can manage the ambiguity of this new thing.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Can you explain what you mean by that ambiguity and where you've seen that sink people or be a hurdle that's harder than people might perceive from the outside looking in?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Yeah, Gell-Mann amnesia, yeah.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Graham himself embodies the work we hope to do, finding and enabling extraordinary people. He's the perfect teacher for those interested in this pursuit. This is a two-hour segment of a four and a half hour interview I did with Graham last year. It stands alone as remarkable, but those that subscribe to Colossus Review will also gain access to the full conversation.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
My favorite ever line on this from someone I know was Henry Shuck from Zoom Info. When he was doing their first, they've been fascinating M&A story to that business and how it got pieced together. And he did it all. Talk about asserting reality.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And on his first big acquisition that was going on, he was flying somewhere and he's like, I remember I'm sitting on this flight and having this thought, like I'm playing pretend business.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I thought that was so funny, but also to the wrong person, terrifying. And it relates to the second question from that list that I love, which is protecting the climate in your skull. So it seems like that is the skill that allows you to do the first one well.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
This will be true for future issues, too. Graham built an incredible investing track record while managing billions for a select group of families. He did it by focusing on and backing people. Our conversation explores a vast range of topics, from what makes a great investment partnership to the power of positive feedback to starting a restaurant.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
How have you seen people do that really well or poorly, protecting the climate in their skull? I love that visual.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
What role does a partner or partners play in this? Like picking a partner?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
We discuss what he's learned about building trust, creating sustainable relationships, and identifying talent. I'm so excited for this new effort from Colossus and so proud of what the team has put together for you all. I'm so thankful to Graham for showing me the way so many times and for being willing to be so incredibly open in this conversation. I hope it impacts you as much as it did me.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It's interesting. It's like a calibration for the would-be partner on whether or not they could be resentful in the case of success. If it works, what are the odds they're going to be like, ah, you know, that was more me than I got credit for or something like that. And your interesting point is if they have tried and failed, they'll better understand how hard it is and price themselves better.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
So it's both. Like you want self-awareness on pricing and fairness on pricing or something like that.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It seems like so much of what you write about is related to periods of transition. You want to start an investment platform. You want to set up a family office. You're trying to hire someone. You seem always to keyed in on like phase changes. What is it about transitions that fascinates you so much?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I was thinking of the Stuart quote of people make money like pros and then manage it like amateurs. How many people like that I know... that want an amazing setup, but somehow don't have it or are in one of these mills that seems nice and probably feels nice, but under the hood is like, there's nothing actually going on. It's like a normal financial advisor with better trappings or something.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I'm curious what those mistakes were that you made entrepreneurially that you kind of referred to earlier that maybe fall in this category of like, if someone else heard this, they might avoid doing it.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I'd love to understand your view on physical spaces. The East Rock office just has this. Someone texted me recently that it was like the best office that he had ever been in in New York. And your attention to physical spaces is very notable. It's like one of the most reliable things about you that like wherever I show up, it's going to have a specific feel to it. What's behind all that?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
What is it about physical spaces that obviously intrigues you?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And why there aren't more setups like what you had with Stuart? Why is it the exception that like proves the rule?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
So welcoming. Yeah. Food is so welcoming. Good food. Yeah. And community table. Yeah. Yeah, exactly. When you're making a major decision, let's say leaving East Rock, what process do you put yourself through as you analyze your own transitions? What do you do? What do you think about, maybe frame differently, like why did you leave East Rock?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
So you're living on the West Coast now. I want to capture a sort of vignette of you with an idea of something you want to create And the process by which you then go about creating this, you do more upfront work than anyone else. And you're willing to just put a tremendous amount that would frankly exhaust and extinguish most other people into getting the original setup right.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And for some reason, the restaurant wanted, it's so simple and tangible. I also love restaurants. Maybe you could just tell that whole story, like from start to finish, what did you identify? What did you want to do? What have you done so far?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It seems to me like this is just something you do all the time. I like the idea of a casting exercise. I don't think I've ever heard you use that specific terminology for it, but you are kind of a casting director in so many ways. That is kind of one angle to understand you, like the world's best casting director or something. Another great example of this is Sohn, where Sohn predated you.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
How many years have you run it now?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Okay. So what was it like to take over something that had its own shtick and gestalt, which is literally just a casting exercise, certainly suits you. And just same questions with the restaurant. Talk me through something that you didn't start in this case, but have sort of made more into your own and what you get out of it and what the process is like behind the scenes.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And I think we'll double down on that next year. It seems like an interesting annual exercise in figuring out like who has it. who is the main characters of the moment, which is a fascinating exercise, like a fascinating check-in. And it makes me wonder about your thoughts on who somehow finds a way to maintain that over a long period of time.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Like Tepper, someone you've written about who is very quiet, you know, doesn't show up in the press very often. But my sense is like, he's been it or has had it for just an insane long period. Yeah. And I don't know how many I could rattle off like that. It's quite rare when there's a handful.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Any observations on that about the people that somehow you could say have it every year, year in, year out over time?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
The category of investor, I won't name them, but everyone can imagine them, who nailed doing one thing really well. They rode one specific wave. They invested in one specific kind of business model or something like that. None of that stuff lasts forever. And so maybe macro is like a unique...
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
ultra flexible and maybe buffets like the ultimate expression of this shed his skin however many times to adapt to a new style but maybe love of the game and a broad purview are like the two ingredients
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I'm curious, as I think about that hierarchy of yours, so I think it's apprentice, expert, professional, master, steward. What is the difference between professional and master? What happens in that gap? How many masters are there?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
How many stewards are there, do you think, at any given time?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I'm curious whether there's more or less capacity for investing masters today than there used to be. And I guess it's kind of a question on like market efficiency and what you think about markets and whether or not it's going to attract great talent in the way it has in the past. As a profession, do you feel like it's as potentially rewarding and exciting for a 22-year-old as it was 30 years ago?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Are there traits in investors that you think matter more in 2024 than they did in 2004?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
In the early days, how would you describe that dynamic between you and Stuart personally? What matched? What fit?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Does AI scare you? Like, what do you think about? It's freaking me out lately, to be honest.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
What would surprise people the most that aren't in the world of what I'll call the very high end of the investment game, where you have very talented, very smart, very aggressive, often investors vying for edge, vying for talent, vying for whatever funds from LPs.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
What would surprise people about the way that world works that you've seen having probably interacted with it as much or more than anyone?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Yeah, yeah, yeah. I know who you're talking about. Yep.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
There's a lesson there to work really hard to start hot.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Can we talk about referencing a little bit? Yeah. I don't think I knew that you were willing to troll LinkedIn as much as you were. You're certainly willing to do more referencing in pursuit of finding the perfect person to lead the thing. What have you learned about this art? And I would call it an art.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It feels like it's a common thing to say now I'd rather reference than interview or it's become a popular idea to do referencing. But 99 times out of 100, when I see people reference, they do three references, three customer calls, three for our bosses or something. And I think that is very different from the way that you've done it. So how have you done it?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I would actually love to hear the story of how you came to this. What was the origin story of you doing referencing? I don't think I've ever asked you that. And why do you find it so valuable?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Just to make sure I understand that point, which I hadn't thought of before, it's not just about making a decision to hire them or whatever. It's actually improving the chances of working well with them after the decision. Yes, exactly. And so the component, I've seen you write about a couple of goals that you have in a reference process.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I think one of them is understanding the elephants in the room. Explain that process and a couple other things I'll ask about too.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
How do you get at the elephant?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
How would you describe your own personal elephant?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It's like you're the ultimate open loop person.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Closed loop being like, what's the thing that he's doing? Get it done as fast as possible versus like delay. Yes. The need to make a decision, like keep options open as long as possible.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
In addition to the elephant concept, you talk about this in this whole category of seeing reality clearly through understanding, through references, trying to understand a person and a situation. You talk about seeing your own reflection in the window. What does that mean?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
The last of these goals, if you will, from this great, amazing piece is seeing the water, which I think is a David Foster Wallace reference, if I'm guessing. Describe that last goal in the process of trying to understand what's going on with the person.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
When we talked when we were sitting by the beach last time I was at Montecito with Boyd and a few others, you were telling us some of these amazing early formative experience stories. We talked about one, which was this moment of ignition, seeing the senior rowers and thinking, oh, if I work hard, I could be that.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I'd love to hear a few more of what you could think of as the formative experiences of your life at any stage. can be investing, can be rowing, can be anything that you feel like were pivotal moments of growth for you or just formative in the way that you think about the world or have experienced the world.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
The rowing one's a great one because I can't remember how many championships you won, like a lot.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Yeah. Yeah. So like an unbelievable amount of success tasted early, which is like an interesting thing. People taste excellence. Yeah. Their own touch. Yeah. At different times.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I would love to hear more about the rowing because obviously it was formative, but also just like such an interesting contrast of, I think, a little bit of identification for you as being somewhat lazy, but so much evidence to the contrary in some of your formative experiences, willingness to work extremely hard. What was it about rowing? The physicality of it? Was it the pain?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I've never rowed in my life. What did you learn there in that space that you worked your way into?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It's like running the mile.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
You're like 32 or something?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Talk about the partnership that budded and what you did with him.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Did it have a similar vibe of touching excellence that the rowing did? Like the intellectual version?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Huh. Makes me think of Teller's thing about the competitive advantage of having seen true excellence. How excellent an example someone has seen is a really important factor about somebody because it's the standard get set. And of course, he saw for Elon that his right hip for six years.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Seek excellence early.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Not just watching, but helping or doing, touching.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
The Reddit guy.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
What happened after Yale?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Describe the company.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
What was graduation like from that business? What happened? What was the transition to the next thing?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It was like a wilderness period.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And he was giving me shit about that. So then bring us home. So from that wilderness period, well, I guess maybe is there any other meta lesson from the wilderness period of just like wandering, trying to find the thing?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Turned on.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
One thing I think a lot about is in that swim, to use your back to your river analogy, after a long enough hard swim, you swim to the order side.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And if I think about my own life, not having come from like crazy amounts of financial success or whatever early on, but I had enough support that I could keep swimming longer, like the sort of nepotism of having worked for my dad and knowing that I probably, he wouldn't fire me. was such an unfair advantage that I could swim longer without swimming to the order bank.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I couldn't have taken as much risk. There's this great quote. I want to find it and read it exactly right. Only those who will risk going too far can possibly find out how far one can go. Yeah. Does that feel like that wilderness thing?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
We've talked a little bit about the origin story of East Rock itself, starting with, I think, $50 million from Stewart and then growing from there. Maybe tell just a quick version of that origin story and what was going on in your head and what your source was, what your vision was, what you wanted to accomplish, how it came together.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Yeah. Straighten your back out.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Can I ask about Josh's, for me, very beautiful visual exercise of going into this cave and bringing with you a stack of blank pieces of paper or something and really trying to separate your attachment to the prior conditioning and experience and on a blank piece of paper, write the perfect setup for yourself and then come out of that cave. I just love that.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I just love that idea, especially around transitions. Yeah. If you were to think about going into a cave and I constrained you on like, I want you to come out and describe the perfect setup. And you're like, when I think of the word setup, I think of you. There's no one better at designing a setup for yet again, managing your own and someone else's money.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Tell me what you see on that piece of paper.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
One last quote. This is you. Whatever a human being desires for themselves will not come about exactly as they first imagined it or first laid it out in their minds. What always happens is the meeting between what you desire from your world and what the world desires of you. It's this frontier where you overhear yourself and you overhear the world.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And that frontier is the only place where things are real, in which you just try to keep an integrity and groundedness while keeping your eyes and voice dedicated toward the horizon that you're going to or the horizon in another person that you're meeting. Can you talk about that intersection? Desire and what the world desires of you.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
The big middle lesson that I would take away from reading everything you've written, spending a lot of time with you, learning from you, is that there probably is a path or a theme for everybody that if they were to get closer to it, on it, in it, That both their lives and the lives around them would materially improve.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
Is this a good example? Do you think of your notion of like the right grip? I know it's an unusual like application of the idea, but like his grip on the overall situation where a lot is handed to you. Maybe explain that cold grip thing. I would love this analogy.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And I entirely credit you with a lot of how I've thought about structuring my life and very specifically to be honest with myself about what I can outwork other people doing. And then to try my best, and I'm still not perfect by any means, to build my professional life and personal life around those things. And I've experienced personally the power of taking that simple idea seriously.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And I am incredibly grateful that you've taken the time both personally and between the two of us, but also at scale to take great care and time. You know, I've seen drafts of your writing and you're painstaking, like you take great care to get it right. And I hope, you know, the impact that it's had.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
I'm sure that if I called around, which I might do for fun and asked a lot of very impressive people, the same question, they would say something similar. So I hope you feel that. Thank you. Yeah. Because it really Munger said, take a simple, great idea, take it seriously. And different people have said it in different ways. But for whatever reason, the way you've said it got to me.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And so I appreciate all the time and just all the amazing lessons and the amazing fun. You know what I'm going to ask at the end? What is the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
feeling and i hope maybe partly what you just said is you feeling me rooting for you always i feel like i felt that and so i know it and then i can pass it along and the gift keeps on moving in that way that's how i would answer that graham was also featured as the cover profile for our newest effort colossus review we're excited to be launching colossus review and its subscription which will be our deepest dives into the world's best investors founders and companies to learn more go to join colossus.com subscribe
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
If you enjoyed this episode, check out joincolossus.com. There you'll find every episode of this podcast complete with transcripts, show notes, and resources to keep learning. You can also sign up for our newsletter, Colossus Weekly, where we condense episodes to the big ideas, quotations, and more, as well as share the best content we find on the internet every week.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
If you think back to like the way that Eastrock as a platform evolved, one of the things if you ask around about Eastrock that you'll hear often is that it feels like such an organic development of a platform that is very unusual in the sense that it can and did lots of different things and lots of different structures with lots of different kinds of managers and was fundamentally unconstrained in what it did.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And I've seen you say before, in simplest terms, the idea is to find the best investors in the world and then make great investments with them. And there's sort of two key parts to that, that obviously we'll spend lots of time digging into both. Is that a fair summation of like the vision of Eastrock was find and partner with the great investors of the world?
Invest Like the Best with Patrick O'Shaughnessy
Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409]
And is the platform really just, we shouldn't study too much the platform itself because that's just a natural outcome of this very simple goal. Like, is that the right way to think about it?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
With the recent acquisition of Tegas, AlphaSense now holds the world's premier library of over 150,000 proprietary expert transcripts from 24,000 public and private companies. Here's the kicker. 75% of all private market expert transcripts are on AlphaSense and 50% of VC firms on the Midas list conduct their expert calls through the platform.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
The form is unusual, but the substance is not at all. I want to come back to like seven things you said, cost plus, process, portfolio, all these things. Probably the question I should have asked even before this last one was, all of this to what end? For the last 80 years when borders haven't changed, very famously, the US has been world police. We've policed shipping lanes.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
We've been the big bat at the table. And I think that the world is obviously changing more multipolar. Maybe describe how you view the end that justifies all of this, everything else that we're going to talk about, the portfolio, the process, the team, the assets, everything else. How would you describe what the U.S.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
's North Star was in defense for the last 80 years, what it is today, and how fast it's changing?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
That's the kind of insight that helps you uncover opportunities, navigate complexity, and make high conviction decisions with speed and confidence. Ready to see what they can do for your investment research? Visit alphasense.com slash invest to get started. Trust me, it's a tool you won't want to work without.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
I want to come back to the Doge thing that's happened before, just less visibly so. But if you think about the US's new set of priorities, or at least its new orientation where it wants to be compensated for its help and its risk, how do you think the portfolio needs to change based on that changing role in the world? That's a really wonderful question.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Ridgeline gets me so excited because every investment professional knows the core challenge that they solve. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Not only are the founders, Kareem and Eric, life's work-level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
If you go back to the old doctrine of two wars at once and maintaining global order, how close do we skirt to that line of being able to fulfill that capability? Like if we had two near-peer battles today? We can't do that anymore because I think... What would break? Well, it's just massing. Describe that. That's a key concept.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
With about $350 billion now committed to the platform and a 60% increase in customers since just October, firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry in AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
If I again zoom to the so what of all of this stuff. Two big ones seem to be be able to defend ourselves. Seems like we can do that. Have deterrence. Seems like we've got that. And then there's the ability to do things in faraway theaters that matter to us. So, of course, Taiwan comes to mind. In that last category, what are the most sensitive so what's in your mind?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit RidgelineApps.com to schedule a demo. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
What's your expectation for how that whole situation evolves?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
What have we learned about the future of warfare from the war in Ukraine?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
When I talk to lots of the leaders of new companies, especially those building lots of drones and software systems to control and coordinate those drones, they imagine a future battlefield where there's not a lot of soldiers because a soldier can't survive. Let's just picture a border to start or something.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
A soldier cannot cross a border where there's just infinity, $150, well-coordinated drones with charges attached to them. And therefore, the future of warfare is drone swarms fighting each other. Where does that future fall down? Where is that not accurate?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Can you describe your view on the dynamic at play today where there's been, in the same way that now we have a lot less people in defense technology, there's a resurgence of interest in that space from an entrepreneurial and investing perspective. There are venture investors and private equity investors wholly dedicated to backing these kinds of companies.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
There are interesting new technologies being developed, subs, drones, everything you can imagine. Andrel is one of the most popular private companies and most valuable. It's a wonderful thing for the country, for the U.S.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
I'm interested in your perspective, I guess, from two sides. The first you sort of already addressed, which is setting aside returns on capital and returns that investors will earn on the deployment of these dollars. It sounds like a huge thing. This is just a net good for the system and it's great. What about on the pure investing side? What are the dynamics that will drive returns?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
What sorts of returns do you expect if you add all this up into some sort of index? I get to just put dollars at work at the market prices in private rounds in defense-only companies. Do you expect good returns?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
My guest today is Darren Farber. Darren is the managing partner of Albion River, a private direct investment firm focused on acquiring companies that produce highly technical defense products and services. He is a former special advisor to the Deputy Undersecretary of Defense, a former member of U.S.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Rickover. Yes.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Department of Defense Task Force for Business and Stability Operation, and the list goes on and on. Darren is a wealth of knowledge in this space and someone I am grateful to have in the US corner. He shares his perspective on the changing role of the US in global defense and how recent conflicts have shaped military technology and strategy.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
What's in the way of having that pervade the entire armed forces, the responsible party for major programs?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
We were talking before hitting record about this funny circumstance where you might have more investing firms than you do assets that will be good to invest in. Maybe say just a little bit more about that. And then I want to ask, where is the money actually to be made in defense investing?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Darren explains his investment approach at Albion, focusing on finding one-of-one suppliers and getting as close to what he calls the fundamental molecules as possible in defense technology.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
And ergo, the investors who themselves have more access to capital, which means they can win the rounds to invest more capital in the companies, also probably have an advantage. This is not a place for the lean mentality.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
What else can we learn from the US defense primes? What can venture-backed younger defense companies learn from the primes? So much of the narrative in support of the new class of companies is how sclerotic and terrible the primes are.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
We discuss insights on evaluating the Taiwan situation, lessons from Ukraine, how the defense budget is allocated, what investors can learn from defense primes, and why technological superiority remains America's greatest advantage. Please enjoy this incredible discussion with Darren Farber.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
I remember when I was focused on public markets and capital allocation as a quantitative study that Northrop Grumman was one of the great stories to study. The acquisitions up through the 90s and then the share buybacks all the way through the present.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
It's really nuts. Cody Kittle told me to ask you in this theme about the lessons of Transdime versus Heiko and what you've learned from those two businesses.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Maybe the fun place to begin is for you to describe with defense investing being so incredibly popular, your state of the union of defense in general. You've been in and around this world for a long time. There's some active wars in the world right now in a way there wasn't many years ago. Just describe how you see the landscape overall, and then we're going to dig into each element of it.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
When you and I first met, the very first conversation that we were in together many years ago was a conversation around the most undervalued assets in the entire world.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
I think yours was firearms and uncut pink diamonds. Yeah. This was at an amazing Graham Duncan East Rock event. And it struck me at the time that the way that you thought about both of those things was that the money to be made was understood through the lens of simple supply and demand. Yes. And that your frame on investing is kind of that.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Can you describe that in some more detail, however you'd like? It just struck me as so elemental to the way you think about things.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Whether it's the Pink Diamond example or something else, is there a second supply-demand story you can tell to really drive home this way that you look at things as you approach them?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Can you explain the concept of net-centric warfare?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Say one more click about in a net-centric world where autonomy and AI specifically play important roles in the future of warfare.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
We should have every kind of capability. If we think about this whole system and how it's all evolved, could you draw or give a narrative of the scenario of your greatest hope and the scenario of your greatest fear? Two separate ones for the future of kinetic warfare.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Is there any part of this world that you're surprised that where you think about it or put a lot more importance on it than the people around you do?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
There's a million things and aspects of this. We could pick any part of our conversation and spend another two hours on each part. We'll keep it here for part one. I think you know my traditional closing question for everybody. What is the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Well, it's worked out pretty well for the people that did believe in you. I love our conversations. I think they're among the most interesting and different of any that I have with investors. I'm so glad we finally got to do this. Thanks for the time. It's a privilege to be here.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts. You can also subscribe to Colossus Review, our quarterly print, digital and private audio publication featuring in-depth profiles of the founders, investors and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Maybe another perspective to offer. You spent a lot of time in the Pentagon. There's the whatever, 870 some odd billion dollar annual defense budget. Talk about the shifting nature of that.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
thing, that dollar amount that gets outlaid, what it's gone to historically that's been most important, how what is most important is shifting, and whether or not the Pentagon is good at keeping up with a shifting landscape in the way it spends its money.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
The Ramp team is relentless, and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
What's like a quintessential example of that playing out, commercial to modified technology?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. As an investor, staying ahead of the game means having the right tools, and I want to share one that's become indispensable in my team's own research, AlphaSense.
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
If I think about our armed forces as a stock of stuff, of assets, of soldiers, of current capability, and as a flow of new dollars being spent on stuff which adds assets to that stock, changes the stock or whatever...
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
Where do you think if you were doing like a 3G zero-based budgeting style approach, I'm sure there's just tremendous amounts of inertia and a lot of the spending that happens this year is just the same as the spending that happens the year before. But if you were starting from scratch, how differently do you think you would spend the $870 billion if you were in charge versus how it's being spent?
Invest Like the Best with Patrick O'Shaughnessy
Darren Farber - The Business of Defense - [Invest Like the Best, EP.417]
It's the market intelligence platform trusted by 75% of the world's top hedge funds and 85% of the S&P 100 to make smarter, faster investment decisions. What sets AlphaSense apart is not just its AI-driven access to over 400 million premium sources like company filings, broker research, news, and trade journals, but also its unmatched private market insights.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. This is a rare opportunity to hear from one of the best investors of the past decade, Josh Kushner. As a side note, Josh is one of the very best people that I've met in this journey over the last 10 years. I hope you enjoy it.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I'd love you to tell the Oscar story specifically, the actual story for how the thing got started. Work our way towards a general set of lessons on how do you identify an interesting problem and how do you help take something from zero to one? With all that in mind, tell us about how Oscar itself got started.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
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Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
In this story, the why now is unbelievably clear, both in terms of your experience, but even bigger picture in terms of the Affordable Care Act. Under what conditions does the why now matter to less or more to you in investing and around incubations? Does there always need to be some galvanizing change like that that enables the new opportunity?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Do the pleasures and the pain of running and helping run a mature platform like Oscar, Are those pleasures and pains very different from the pleasures and pains of the really early stages of businesses?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
One of my favorite snippets from all the interviews I've done was Joey Levine and IAC saying he once walked into Diller's office and had this opportunity. He said, you know, if we really do it right, we'll have 100 million in revenue in this timeline. And if we really do it right, it'll be 100 million in profit. And Diller looks at him and goes, why bother?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Like, why would we work on something so small? I thought that was such a wonderful story around scope of ambition. It brings to mind just all the other things you've done on the incubation side, where the lesson is, if you're going to do it, it's hard no matter what. So go for something that can be really, really big.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
How do you think about identifying good problems through that lens or that frame? You've done it in healthcare several times. You've done it elsewhere. What does a good problem look like? And how do you think about bringing it from zero to one now that you've done this more than 10 times, I think, through Thrive?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
What was the moment that you decided to start Thrive in the first place? Because I think you were 25. You were extremely young. You had basically no work experience at the time. So what were the antecedents to Thrive that matter? What were the ingredients to the early recipe, if you will?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Yeah, no generalists.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
My guest today is Josh Kushner, founder and managing partner of venture firm Thrive Capital. Josh started Thrive in 2010 and launched its first institutional fund in 2011. That first institutional fund was $40 million and in it, Thrive led Warby Parker Series A, invested in Instagram and incubated the business with Josh co-founded called Oscar.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I'd love to talk a little bit about a history lesson using the funds themselves as the timeline mileposts, if you will. Tell us a little bit about the significance to you and to Thrive of funds one, two, three, and four. And then I want to pause on four and talk. I know that was a really important fund for the firm. So I guess start with one, two, and three.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
If you had to sort of top line what was happening, why it was important, and what you learned from the first three funds, could you do that for us?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
How did you know that that was the right move going from funds two and three into four?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Thrive has gone from strength to strength since and now manages $15 billion with a small team of nine investors. Their portfolio is stage agnostic and their track record includes many of the best known businesses from the past decade, including Spotify, Unity, Stripe, and Twitch, among many more.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
You raised this idea of competition, right? The competition wasn't doing X, Y, and Z, and it created an opportunity. And I'd love your perspective on industry-wide competition today and kind of your views on the different models for, I guess, building a venture firm or building a private equity firm just in general. Obviously, you've gone one direction with Thrive.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Maybe the opposite of the spectrum would be something like artisanal small partnership, a couple of partners that share economics. There's lots of examples like this where they do it, two people or three people or something like that. That would be one model I'd be curious for your thoughts on.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
And then the other like monoliths that have now built multistage firms, built firms that can go anywhere, do anything, have teams in different geographies. How do you think about the different models, the pros and cons from your seat and what you've observed?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Here's a puzzle. What do OpenAI, Cursor, Perplexity, Vercel, Plaid, and hundreds of other winning companies all have in common? The answer is that they're powered by today's sponsor, WorkOS. If you're building software for enterprises, you've probably felt the pain of integrating SSO, SCIM, RBAC, audit logs, and other features required by big customers.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Josh rarely speaks in public about the firm and their philosophy, so it was a blast to do this with him. Please enjoy my conversation with Josh Kushner. I have a strange opening question for you, which is about, it's a very meta question about the nature of this interview in the first place.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I want to spend a few minutes on talent and people and recruiting them and seeing potential in even very young people, which you just described a few people seeing in you. I don't know if you know this, but the first time I was in your office, I was with David Fialkow immediately beforehand. And I mentioned I was going and he got this, as Fialkows want to do, this like sparkle in his eye. And
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I'm curious what you think that was. Why, when you were 25, did a few people who we can now safely call investing legends, both on the endowment side and the GP side, what do you think they saw? And another way of introducing the question is what you see in others, because you've done the same thing over and over again in turn, paid it forward, I guess.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
But starting with you, what do you think it was that Andy and David and Joel and all these people saw early on in someone that objectively didn't have an investing track record?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I've talked to you about it a bunch, and I think you literally at one point wrote a note to yourself about why you might do this. And when, and if we publish this, I think it will represent probably 80% of the total minutes of you being recorded in a conversation. And I'm just curious about that.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Where does the immigrant mentality land for you? I know that's a common theme of people that you've worked with and for you and your family too. Say a little bit more about, people have heard that phrase, they understand the general concept, but what is that felt experience?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
How do you think about maintaining the power of that story in your own family and in your business? Obviously, so many of the hard things that people go through shape them in extreme ways, probably in the ways that you're describing. And then hopefully things get better. And you and I talk about our kids a lot.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
How do you think about this story and your kids or this story and the next person, the partner that joins you at Thrive and harnessing this story for good, I guess is the way to ask the question and maintaining the power that it's had for you personally, which sounds pretty significant.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Everything else we'll talk about, I think, is somewhat downstream of some very deliberate choices you've made, your style, your personal style. I've really enjoyed getting to understand. And so I'm just curious, in that note, what were you saying to yourself?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I would like to linger on talent because... I totally agree that the work ethic and wanting it more is the ultimate advantage and persistence trumps maybe everything else. That being said, I'm lucky to know some of your partners' current and past.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
And one of the things that I think if everyone listening met them would stand out is their intellect, whether that's Miles, who's now at Bunchmark, or Chris, who's now at Pace, or Kareem, who's with you now. All these people... have, I think what could be fairly described as a sparkling intellect. Someone said to me about Miles one time, what's the deal? What's his superpower?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
This is a very good investor that said this to me. He's like, he's just smarter than everyone. So amongst a group of really talented, smart people, how do you test for the wants it more gene? If that's the thing that you choose over everything else, and you're lucky to hunt in a really smart, talented pool of people,
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
How do you test for that, especially if the person's very young, which has been the case in a lot of Thrive's partners. They're mid-20s or late-20s. They're young people.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
That is the type of person that we want at the team. When you think back to the earliest days and the first couple of funds, what were the investments that were the things that started to form the kernels of the story? Obviously, there's the Instagram story. We can tell that if it's interesting and people know you for it. So maybe it's worth hearing your version of it.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
But along with that one, what were the other consequential investments that you made early on and what was going on around them? So maybe to take a step back,
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I want to understand how that philosophy developed in the early days. So Thrive could have gone a million directions. You were concentrated. Proof's in the pudding there. Was that how you planned it from the start when you were doing your independent thinking exercise that convinced Andy Golden that you're onto something?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Was that part of it or did that develop as a result of early deal-making, early investments, early observations? How did that crystallize?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I'd love to talk about your great analogy for all the kinds of investing that you do that uses real estate as sort of a proxy. Maybe I'll kick it off with like an idea that someone said to me recently, which is the market may underprice market-leading positions in companies. I guess another way of saying that is may underprice quality at a certain stage of development.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
And I think the analogy you've told me about you explaining this to your mom, like kind of what you did through the lens of real estate, It was really, really interesting and informative. Maybe you could share the whole framework.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
At what stage of a company's life do you think that it can be on Fifth Avenue? Is it a revenue stage on average? Is it like a fundraising stage? At what point does that quality third versus Fifth Avenue thing start to sort itself out, do you think, on average?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Can you give an example, not a specific one, I don't want to name companies, but of the category mistake of thinking Third Avenue is Fifth Avenue? What is it that has snared you in that specific trap, especially at the late stages? The thing that I love about concentration is
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
If you think about the environment that we're facing today and the tension of, I'll call it like a hangover from extreme valuations, especially late in COVID. Apple just announced their new product, which you mentioned you started your career right at the advent of mobile. And we know where that led. This explosion of opportunity in companies and AI has been happening.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
We've talked a lot about it offline over the last, call it, year now. So you've got these two unbelievably exciting companies could be new technology platforms or enabling technologies that are exploding on the scene at the same time as we're dealing with this tremendous hangover and there seems to be the end of a capital cycle. It feels like a weird time.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
How do you incorporate your understanding of the time and the prevailing circumstances like the ones I just described in an investing process. And I'm asking this because you've seen a lot of them now. You started the great financial crisis. You've seen a lot of environments since then as an investor. Do you care? Like, does it matter? Does the macro environment matter much to you?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
What was your reaction when you saw Nat Friedman and Daniel Gross's available computer for, I don't know what else to call it. Do you know what I'm talking about?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
For someone that's so deliberate about people in their lives, why sell a small stake of Thrive, the business itself, to the group of people that you sold it to? Walk me through that episode of why you did it and what you get out of it.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
So we feel very lucky to have this extraordinary group. How do you think about setting and controlling your own ambition? And thinking all the way back to your first conversation with Andy Golden about the polls that happen on asset management firms as they scale and trying to keep some purity. The way you talk about a concentration of people and ideas is that expression of that purity.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Do you have big ambitions? Do you think about, I want Thrive to be X, Y, or Z in 10 years? Is that prudent? How do you think about it?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Tactical question, which is how do you manage the tension between being the CEO of Thrive, the business that you're building in all those ways you just described, and being a pure play investor that is looking at companies and meeting people and thinking about ideas? Those two things both take a lot of time. How do you actually do those things you just described of building the pieces of Thrive?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Is it a trusted lieutenant? Is it I'm just curious in the nuts and bolts of how the thing actually works.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
How do you do that? Is it different learning? Maybe we could take a real example today with AI, just because it's the obvious one that everyone's curious about and talking about. Is it just constant conversations with the smartest people you can find? Is it sitting and thinking? Is it reading? Is it all of the above? Is it talking to your team?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
There's only 10 hours in the day or whatever it is that you can work. How do you think about allocating them?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
So having lived through mobile and cloud and so many of these big things that have driven the world, what do you think of these two latest things and what they might unlock? And I know you've invested in open AI, so obviously you're super familiar with what's going on and how exciting it is and also the limitations and all these sorts of things.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
At this point in time, what is your model for thinking about these things?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
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Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
One of the things that comes up if you ask around about you and Thrive is, if I say like, what questions should I ask Josh? Several people will say, talk about the taste on the consumer side that developed early. Because for the most part, Thrive invested in the consumer space, which on average didn't do that great. But leading companies did very, very well.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I'd love to do the same in just a couple other categories. So just go down to the weeds of what you've learned in a category building and investing in companies. The first of which is crypto. You've really been notable in your absence from that space. We've talked about extensively, like you guys can go anywhere, you can do anything. You could have done a lot of crypto. You didn't. Why not?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
What was less exciting about that? What answer would you have given in early 2021 when... Everyone was investing lots of money in crypto. What was it about that space? What was your model of that space at the time?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I think that's roughly what's happened, yes.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
When and if it solves a tangible problem, you understand, you'd be interested. Yes, of course. Like everything else, always open-minded. What about financial services slash fintech? How do you think of the world of opportunity in and around that space?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
And Thrive was often invested in those things. How do you think about the development of taste?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Are there other areas that you think as distinct areas of opportunity like fintech, healthcare, AI, et cetera?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
What was it like shadowing? I'm thinking of a legendary technologist. And I know early in your career, you shadowed Mark Andreessen for a period of time. I think Michael Ovitz introduced you. What was that? Why did you do that? And what was the experience like?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
You and I have talked before about the power of communication, which is funny since you basically never communicate with the outside world. I think it's great. And I'm appreciative you're doing it here. When you think of great communicators, and I know there's lots that might come to mind, but who comes most immediately to mind for you?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I was amazed to see him pop up as an early investor in Palantir. He gave a talk with Alex Karp at Palantir. It's surprising. It's disorienting to see this macro guy that's mostly talking about interest rates all of a sudden pop up early in all these company deals too. Kind of an unbelievable story. What about Henry Kravis? What has he taught you?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
The only rule is there is no rules. I think it's a good thing to remember. Well, there are rules. Ignore them. There was.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Of course, of course. Last one on this type.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
He's one of the most special people that I've ever met and I owe so much to him. Did he tell you or show you or a combination to not care what other people think? He showed me and he told me.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
My favorite Joseph Campbell quote is the privilege of a lifetime is being who you are, which sounds very simple, but it's actually quite hard to do. Sounds like that's the lesson he's taught you. David's been very generous to me. How has becoming a father changed you?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Do you think you're different at work as a result of being a dad? Absolutely. In what ways?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Are there values in the business that a lot of them just come through in all your answers? But I know every year you write a very simple restatement, I guess I would call it, of firm values that you send to the whole firm. Any of those that you think are really important that we haven't touched on as much?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
You and I, I think, are both in love. You turned me on to it, this chapter in his book called Rules. Can you tell me why you love that chapter so much, what it says and why you love it so much? Highly recommend people go listen to it.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
How do you balance, as the firm has grown, doing an investment like you just did in Stripe, which is an iconic round, maybe $2 billion, into a single company, single round, obviously iconic business, With the next check perhaps being a $2 million seed check into a company, which on a $15 billion asset base, it's just hard. The $2 billion checks move the needle, no matter who you are.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
How do you reconcile those things?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
When we do it, we're there, we're fully in. I asked earlier about how you think about product market fit for an investing firm with a long horizon. And you mentioned also that you think of Thrive's a business, your customer's the founder. How do you think founders, especially these great ones, make decisions on who to partner with?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Everyone's money's green and the industry that you're investing in, even though you were very early to it, is way more institutionalized. So there's just more committed capital flowing around. There's a lot more choices. What in your experience really drives the decision-making process
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
It could just be that that's the answer, right? That founders, like any customer said, talk and reputations are built slowly and by word of mouth. But it's hard for me to understand how incredibly quiet Thrive is. If you're a founder, you can't go watch a bunch of stuff, listen to a bunch of stuff, read a bunch of stuff and know who Thrive is.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
But you go through the list of companies that you've invested in and it's the who's who of this generation's technology businesses. Not everyone, but a lot. And that has to happen somehow. It gets me curious.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
What a fascinating trio. which is so interesting to me because they are so big now. Andreessen's done this so well too. These are huge, enormous firms, and yet still that is the brand and the reputation. It's remarkable. What's the most unusual interest of yours that you feel pulled back into over and over again?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Is there anything unusual that you feel odd in how much you return to it over and over again relative to your peers? Just as a general area of interest.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
You have turned me on with a couple others. Sarah Fetter is the other person that's done this for me to the work of James Turrell and the idea of installation art, more generally speaking. What is interesting to you about that kind of art?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Very Ferris Bueller.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Raises an interesting question, which is artists literally are manifesting the thing in their brain. And Dick Slack, a company you obviously know incredibly well, was itself a pivot. The thing that Stuart was imagining was a game. And then it became something very different.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
How do you think about vision as a key ingredient for founders, given the number of companies that have started as one thing and become something very successfully, but very different? Does vision matter?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
What have you learned about the conversation and negotiation with founders for late stage investments where pencils can be out, math can be done? There's more to tether. I suspect you've gotten very good at having the conversation with a founder so that you end up in a positive someplace where they're happy, you're happy, you're partners.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
And maybe that there's also been things you've learned not to do. I'm just curious about that muscle and that process.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
What do you make of our industry, the investing industry overall right now in 2023? Are there things that surprise you? Are there things that excite you, that turn you off? I'm just really curious as someone that's not been in this a while, what the industry itself feels like to you in this environment?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
It feels like a period of time with so much change, just in the same way that you started in a period for the world was hard. The hangover from the financial crisis was serious. I remember it. I started my career at the same time as you, and it took years to feel our way through that. And what you did at the time was fairly contrarian.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
And it's exciting to think about that looking forward, certainly for me. Are there aspects of Thrive's story that we haven't talked about that you feel are most formative or most important for someone from the outside in be trying to understand the business?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
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Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
So that could be information pushed to you on the investing team that you wouldn't have found for your own devices. It could be reporting or telemetry for a founder on their industry. It doesn't matter. It's custom in each situation, but you need a data store to be able to do any of that stuff.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
If you were giving an interview for a documentary about Kareem and how he's done this multiple times, built businesses that have gone on to be very, very large, how would you describe that? What's he doing? What's going on to make that possible? Not just once, but multiple times with him in particular.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
If you were investing, let's say you got to shut down Thrive and the only thing you're allowed to do is invest in other investment firms. And you listed an amazing list of people that have been a part of the Thrive story in one way or another, whether it's KKR, there's lots of very successful Blackstone, fascinating investment firms. How do you think you would approach that challenge?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
What would you look for? What would you care about?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Say more about distraction. You've so cultivated a lack of distraction that word hasn't come up yet.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
First time we met, you told me this amazing line. I think one of your parents told you about tall buildings. Can you share that line?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
It's the greatest thing we could ever imagine. So simple. The whole world would be better if they had some version of it. Creating simplicity is complex. I think this has been so interesting for me to learn from you how to take a few simple ideas and take them very seriously. as it relates to building an investing franchise.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
And I know that you hate this version where you're the one answering the questions, not asking them. But I really appreciate your willingness to do it because so many people listening are aspirational investors or building an investing franchise or building a business. And I think our conversation's been, for me and hopefully for everyone else, just a really good reminder of
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
that it's simple things that work, but you have to take them very seriously, which you've done with Thrive. And I really appreciate you doing this with me. And I know this will probably be the only one of these that you do for maybe another 10 years. So we'll do another one when we're a little bit older and our kids are grown up or something, but I appreciate your time today.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I think, you know, I have a traditional final question that I ask of everybody. What is the kindest thing that anyone's ever done for you? It's actually a crazy story.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
So it's inner rings and that guy's business card. Yeah. Amazing. To close on a light note, we both love basketball. Yeah. Outside of business investing, something we're both deeply in love with for sure. Why was it good that you could not dunk until after high school?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
As a fellow late bloomer, I love that story. And I think it's the perfect place to close. Josh, thank you so much for doing this. Thank you, Patrick. If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
You can also subscribe to Colossus Review, our quarterly print, digital and private audio publication featuring in-depth profiles of the founders, investors and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
I promise this is my last preliminary philosophy question, but I think you tweet about once a year or so, so consistent with what you've said so far. The most recent precious use of one of your annual slots was to share a story from C.S. Lewis called Inner Ring, which I'm familiar with and love. And I think it's just a fantastic little, I don't know what to call it, essay story or something.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Why share that? What does that mean to you? What's the gist of that and why has impacted the way you think about the world?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
What have you learned about the different sources of drive and motivation, especially in the context of founders? You called them heroes earlier of the stories of their businesses and you wanting to not get in the way of that story and really be supporting quietly, which is a very nice notion.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Motivation seems like a critical thing, like psychology and motivation to understand when partnering with these people, especially if it's a very early generation. young business. And you just talked about inner rings as maybe a pernicious form of motivation of trying to get something, but it being the wrong direction to be pointing.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
New SEC update 31 CFR hits investment firms in under a year, and managers are getting ready for it now. If you think basic OFAC screening is enough, think again. You'll need continuous monitoring of your investors and all their beneficial owners across multiple watch lists, plus a comprehensive anti-money laundering program. Passer has already processed 50,000 LPs and built the complete solution.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
What have you learned about good, bad, healthy, unhealthy motivators and what drive people to do exceptional things?
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Talk about the relationship between starting and investing in companies for Thrive, which, as I understand it, is deep in the DNA. We were talking at lunch about this idea that excellence is the capacity to take pain and that the experience of pain as an entrepreneur is probably a huge competitive advantage as an investor.
Invest Like the Best with Patrick O'Shaughnessy
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
And I think you started Oscar Health the same year as you started Thrive or very close. So you were dual tracking this investor. Obviously, you're an entrepreneur having started Thrive too, but dual tracking the investor entrepreneur styles at the same time and have ever since. What has that interplay meant to you and to the firm?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are end-of-one conversations with end-of-one people. There's nobody I've met quite like Doug Leone. Incredible drive, energy, and aggressiveness. Also, one of the great voices to listen to. A fearsome competitor and builder. I listen to this at least once a year.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Don't risk SEC deficiency letters, fines, or regulatory enforcement. Visit passthrough.com to get compliant now. My guest this week is Doug Leone. Doug led one of the world's most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
You have a unique perspective having been a part of Sequoia across four different decades, more than 30 years. So you've seen an enormous evolution of this industry, which today feels very institutional. It's big. There's lots of norms. It's a career path for lots of people. And I think that's probably different from when you started.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
I'd love you to reflect on what venture looks like to you today relative to the perspective of all the time you've worked in the business.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
We're seeing right now a harder market for sure, but with AI as a subsector of the technology market, one that is very red hot and still seeing prices for deals that seem crazy from the outside without investigating the companies. I'm sure you've seen countless little mini cycles like AI is today. So what is your style of approaching one of these new thermonuclear technology markets as an investor?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Alongside Mike Moritz, the pair managed its expansion from a single $150 million early stage fund to an $85 billion global powerhouse. It was a privilege to sit down with Doug and learn from him. We talk about his tough start at Sequoia, get into the technicalities of great go-to-market motions, and survey his advice for other investors in the industry.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
If you were 28 today and of similar gumption and interest, do you think you'd be going into venture given what you described as the more mature nature of the business?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
A key theme that will stick with me from this conversation is Doug's insistence on keeping things simple and clear. Please enjoy my great conversation with Doug Leone. Doug, I've heard you interviewed elsewhere, and I wanted to start our conversation somewhere a little bit more unique. I'd love you to talk about the heart and mind of Don Valentine.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Speaking of your passion for go-to-market, describe what you've seen the very best at that do consistently. Is it working from the product towards the customer's need? Is it working backwards from the customer? Are there other things that you've seen and recommend over and over again of the very best at this?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
I've learned a lot about him, obviously someone that was influential on you and a key figure in the history of this style of investing, of our style of investing. Maybe start with his heart. What was his heart like?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
What are the components of great positioning for a product?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
If you think about what I'll call mediocre positioning, you'll know if there's amazing positioning because you'll just see the thing flying off the shelves. And you'll know if there's terrible positioning and that the danger is somewhere in the middle, like it's kind of working.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
What have you done historically when you see that and you see founders start to build upstream the demand gen and the sales orgs on top of mediocre positioning? That seems like a very dangerous spot for a company to be in.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
I hope you enjoy it. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Assuming we've got a company that has a fantastic positioning story, the next stop upstream is demand generation, which I assume by which you mean the proliferation or the propagation of that message through a bunch of different channels. Leads, getting leads. Getting leads. What are the great components of demand generation?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
If you think back to your early days, you mentioned earlier, a lot of investing in highly technical companies and founders. And maybe as Sequoia has grown and as the world has grown, more founders who are less technical, but nonetheless can still build huge technology businesses. How does that change over your career manifest in the way that you interact with companies early on?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Is it a different set of people that you're looking for? Is it a different set of attributes or characteristics? Talk about that shift.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Those are the three goals. It sounds like in that description, one of the things that whether this was the goal or not, I guess doesn't really matter. But one thing that's happened is that Sequoia itself has built serious enterprise value.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
It's a private company, but unquestionably, if you were to float it in the public or go to a firm that wanted to buy, Goldman wanted to buy a piece of it, the price would be really high. And that's probably quite distinctive from the older school law firm like Cottage Industry Partnerships.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Do you think that's the right orientation for new entrants into the venture space, that they should be trying to build a firm that has enterprise value? I think that is the kiss of death.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Maybe to sum that up, I would say stewardship over ownership. You got it. You got it. And what I'm sure is this is an incredibly fruitful and colorful partnership with Mike Moritz all these years. When have you and he most disagreed on something?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
You were 10 or 11 when you came to the States. Is that right? I was 11. What was high school like for you?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
If there was a big red button on your desk that if you pressed it, you would have gone to a pristine, super nice school instead of the one you went to, you wouldn't press it.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
How can successful people with means that have kids and love them and want the best for them take heed of that advice and do something with it?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
The corollary is probably that there are many ways to hell too. What are the most common failure modes that you've seen for investors? So investors that either you've employed and worked with at Sequoia or seen and observed that just do a bad job. What are the most common reasons why?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
As you were building Sequoia and as you've watched founders build companies, do you think that competitive advantage can be architected ahead of time? Or is it something that emerges and then gets fostered after the fact? I've seen it both ways.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Has your view on competitive advantage changed or evolved a lot over the years?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Something in the history of Sequoia that sounds incredibly stressful was the early 2000s and the word clawback comes to mind. Can you talk about that story and coming to terms with what that term meant in the fund docs and what you did to work through it?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
If I were to do like a return attribution going from 0.3 to 1.9, it's a big swing. What were the literal components of that that were influenced by what you did? What did you literally do to make that change happen?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus Review along with all of our podcasts at joincolossus.com.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
As you think about your LPs who you've mentioned already are predominantly foundations, charities, endowments, et cetera, even just constraining to that world. What do you learn about picking the right LPs? Even if I was only going to sell to foundations, let's say, what have you learned about the right LP partners and finding them and partnering with them?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
You mentioned his toughness in the earlier years. Maybe draw the spectrum for me in terms of what was the most productive part of his toughness and if there was any unproductive part of his toughness. It feels like this is an era where that word toughness might become important again.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
What stands out as the most interesting question that an LP has ever asked you? Let me give you a little secret.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Yeah, I've heard you say elsewhere that performance, maybe there's a lot of values, but ultimately performance is the cultural thing that matters most, which makes a ton of sense, obviously, given everything we've talked about. How do you make sure that that is on everyone's mind all the time?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
What are the actual behaviors that you've engendered in the firm that make sure that performance is the thing at the top of that list for everyone?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
And we look at them quite often. Speaking of the argument piece, what are the components of a fantastic memo? A fantastic investment memo? I just rule off the same question. I love this answer. Complete clarity.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
I can't imagine the number of people that you've encountered of extreme skill level. If you think about a dinner where you're taking a founder that you've just invested in, who's beginning to see some success, but it's still early. And you could pick any three dinner companions to impress upon that founder some of what they've learned.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
And these people could be living, dead, whatever people you've encountered. Which three people would you bring to that dinner? And what about them?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
What black magic popped out at you most powerfully when you first met a founder? If you think back on just someone where it's just instantaneous recognition of black magic, who pops to mind?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Simplicity is a wonderful core theme of the conversation. Exactly. I've loved our talk. I've learned so much from you and your partners and watching and learning from the firm. I ask everyone that I speak with the same traditional closing question. What's the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Pretty powerful. Doug, thank you so much for your time. My pleasure. If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand edited transcripts.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
You can also subscribe to Colossus Review, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at joincolossus.com slash subscribe.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
I've gotten a bit of feedback on your style now that is sort of the opposite of insufferable and that you weren't fit to listen to founders. I've heard that you're actually a great interviewer. I want to come back to that. And not that you're insufferable, but that you're quite caring. What caused the change?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
And maybe to begin, what did insufferable and not fit to listen to founders mean when you were young?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
I spent a lot of time talking to your partner, Ravi, about demons and the demons that are in certain people for whatever reason, and the ways that those demons can motivate or drive entrepreneurial type people to enormous success. And one of the things that Ravi told me was that you are extremely good at sussing out a person's core motivation and
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
via listening, ironically, given Don's note to you. And I'd love you to talk a bit about that skill and why you think it's so important to understand someone's core motivation.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
New SEC update 31 CFR hits investment firms in under a year and managers are getting ready for it now. If you think basic OFAC screening is enough, think again. You'll need continuous monitoring of your investors and all their beneficial owners across multiple watch lists, plus a comprehensive anti-money laundering program.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
In addition to asking why in lots of different ways, are there other favorite questions or topics that you find yourself returning to over and over again as you're getting to know people?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
How much time do you think it takes on average to really understand somebody?
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Pass-through has already processed 50,000 LPs and built the complete solution. They handle everything from being your AML officer to monitoring suspicious transfers and even handling your annual audit and training requirements. All firms filing SEC Form 80Vs, including those with VC exemptions, need to be 31 CFR compliant beginning January 1st, 2026.
Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
What were the most formative experiences that you had prior to becoming an investor that you think most impacted how you functioned as an investor? I know you were an excellent salesperson at early jobs at HP and Sun and Prime, but what specific experiences stand out in memory as the most impactful on you?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are end of one conversations with end of one people. There are many people like Cyan Bannister. She has defied the odds to become one of the great angel investors of this era, and she will get you thinking about the purpose of your work, whether investing related or not.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Was there a moment when you first remember making that explicit choice?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
You'll need continuous monitoring of your investors and all their beneficial owners across multiple watch lists, plus a comprehensive anti-money laundering program. Passer has already processed 50,000 LPs and built the complete solution. They handle everything from being your AML officer to monitoring suspicious transfers and even handling your annual audit and training requirements.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Sorry, what is it like to look at something like a stroke with wonder and curiosity?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
I'd love to hear a description of that.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Why do you think that probably for those listening like it is for me, it's so hard to imagine, much less pull off the feeling of curiosity and wonder in the face of such adversity? I think everyone listening would probably say, yeah, this is a very rare perspective we're hearing. And I don't think I'd be able to pull that off. So why is it so rare, do you think?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
All firms filing SEC Form 80Vs, including those with VC exemptions, need to be 31 CFR compliant beginning January 1, 2026. Don't risk SEC deficiency letters, fines, or regulatory enforcement. Visit pass-through.com to get compliant now.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
I'm reminded of my favorite Rumi quote, which is take off your mask. Your face is glorious.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Preaching to the choir.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
So if I map some of this back to Peter's amazing one liner to you and dig in on that notion of your skill at feeling when the feeling is a signaling to you by when you meet with a very young company and founder. Maybe describe what that's like. Is it the recognition of someone that's heeded their calling? Is it something about the person?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Walk me through the, I'm sure feeling is hard to describe, but as best you can, how would you describe that skill of feeling that Peter pointed out in you?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
I was going to ask for an example. So perfect.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Please enjoy it. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
I mean, it makes perfect sense to me that you're not going to get unusually good results by doing the same thing other people do. So the toilet paper convention makes lots of sense to me. Do you have a favorite example of some unique input like that leading to an investment that you made?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
My guest today is Cyan Bannister. Cyan's life story is remarkable. She was homeless at a young age, dropped out of high school, and five years ago, she suffered an extremely rare stroke. Yet in spite of all of this, she is one of the most optimistic and curious people you can hope to meet.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Cyan is also one of the great angel investors of this era, having invested very early in SpaceX, Uber, Postmates, DeepMind, just to name a few. She became the first female investing partner at Peter Thiel's Founders Fund and now invests at Long Journey Ventures.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Our conversation is as much about investing as it is about the essence of life and how connecting with that will help us in our professional pursuits. It's also full of awesome stories about people and companies like SpaceX and Bill Murray. Please enjoy this fantastic conversation with Cyan Bannister.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Yeah. Fascinating. So what price did you end up investing in Uber at?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
$8 million?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
So that one worked okay for you. Tell me the second half of the story. What is it like... to be an investor and to hold on to a business that ends up being, I think it just hit an all time high yesterday or something. Tell me about what that part of this is like. So there's the decision. And I remember talking to some of the early Bitcoin people that made the most money in Bitcoin.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
And one of the things that they had in common was that they were often already rich. Because once something 10 or 100Xs, the pressure to sell something can be pretty high. And then the thing ends up 10,000Xing or whatever. So I would love to hear that side of this same story. You've bought it. You're in an unbelievable price in a generational company. Then what?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
What was it like to watch, to hold, to engage with the company once you had invested?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
So, Sian, this is a hard one to know where to begin, but since we were just talking beforehand, you sort of gave me the perfect opening question. Do you think that spirituality is an investable category for venture investors?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
And did you hold it this whole time? Like, were you still holding your original investment when it went public?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
What is beautiful about capitalism too?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
To zoom to the maybe extreme outcome of what a capitalist system allows for, your story would be remarkable if it was only Uber and nothing else. But maybe you can tell the SpaceX story.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
When you think back on these stories, are there lessons that you pull from them or do you just view them as sort of like crazy things that happened? I mean, the fact that you put all your money in SpaceX is crazy. I imagine, I don't know what the entry valuation was there, but I know what the current SpaceX valuation is.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
It's totally fascinating. It's also a good excuse to go back to what we started the conversation with around spirituality. How did you get into this? So now that I understand these sort of like following the white rabbit holes that you go down, what is this rabbit hole? And I don't know if you've made investments in this space or not. If you have, I'd love to hear how and why and what.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
But first tell us the journey that you've been on, the learning journey that you've been on These are the ones that you've been described in this specific field of spirituality, because if I'm not mistaken, a couple of years ago, you were an atheist and maybe that's different now, but I would just love to hear the arc of that story.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Speaking of spiritual beings, what did you learn from Bill Murray?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Invest Like the Best is part of the Colossus family of podcasts, and you can access all our podcasts, including edited transcripts, show notes, and other resources to keep learning at joincolossus.com. Here's a puzzle. What do OpenAI, Cursor, Perplexity, Vercel, Plaid, and hundreds of other winning companies all have in common? The answer is that they're powered by today's sponsor, WorkOS.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
How much of your investing thinking does the word contrarian describe? How do you identify with that word related to your investing strategy?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Can you tell me about the violin kid?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
You strike me as an incredibly evolved human. And I'm curious that given it's been quite a while since you made those Uber and SpaceX investments, obviously unbelievable returns earned from those and many others, how your investing is most different today, if at all, from when you made those kinds of investments.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
And maybe it's an excuse to talk a little bit about long-term ventures and what you're building there and why you're doing it. but I'm just so interested to know how your practice has evolved alongside your own evolution.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Before you joined Founders Fund, what did you see in Peter and in them? And what do you think they saw in you?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Just yesterday, I talked to one of the Founders Fund partners about an investment that we're looking at. And I asked him the question, which was like, what attributes do you think matter in the next investor for this business? Because obviously we all want it to succeed. He laughed. He said, well, the attribute that we want is that they leave them alone.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
You know, we believe that most of these investors are kind of useless and they just waste people's time. with their supposed value add. It's such a funny thing to think about, but it makes me wonder about your lessons or experience with the professional investing world.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
So much of what makes you so interesting to me is just so different than like the institutionalization of an asset class, which you hear a lot about as it relates to venture these days. And there's so much money flowing around. So of course, supply rises to meet demand. But I'm really curious how you would assess this whole world, the good, the bad, the ugly, having now been in it quite some time.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
One of the things that Justin Maris told me to ask you about was integral family systems. I'm fascinated to know what you've learned there.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Do you still feel fundamentally flawed in any way?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
This is kind of a weird one, but if you had in a checking account, $1 trillion, what would you do with it?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Say more. Why? What about it?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
I just had him on. It was a very fun episode.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
How would you sum up what you learned about the difference between that early, early stage and the slightly later stage that you tried to make work? What is the phase change that happens that makes your skill in one not necessarily translate to skill in the other?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
It's meant to expand the mind.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
If I was asked to describe you, one of the things I'd probably say is every time I see a text from you, I know it's going to be something interesting that you've uncovered. It's almost like dispatches from the future or something is how I think about it. And I would love to know just as we wind down, what fun dispatches from the future you're seeing today.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Of course, ladies illustrated primer, right?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Well, I could talk to you all day long. I think you have such a fresh and interesting perspective on the world. Obviously, you've been one of the more successful investors of this era. We've explored a little bit, but we could explore plenty more. But I'm forced to go to my traditional closing question. What is the kindest thing that anyone's ever done for you?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Wonderful closing story. Thank you so much for an awesome conversation and for all your time.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
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Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
So obviously at the time when you joined, you had a ridiculous seed investing track record. We'll talk about some of those companies in a few minutes.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
But if you had to abstract away the track record, like the obvious evidence that you were good at doing this, what do you think Peter would have said before you joined about what made you interesting and special relative to say, you know, other people? I'm sure Peter's reference class is pretty good. So qualitatively, what would he have said? Quantitatively, you were great.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
It's a wonderful way to sum it up. So tell me about how you think differently, what that North Star is, what those principles are. I'd love to explore those in turn. You can take them however you'd like.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
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Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Are there any other principles that you think about often as you're making a decision or as you're searching for things that might interest you?
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
WorkOS allows you to build like the best with delightful APIs, comprehensive docs, and smooth developer experience. Go to WorkOS.com to make your app enterprise ready today. New SEC update 31 CFR hits investment firms in under a year, and managers are getting ready for it now. If you think basic OFAC screening is enough, think again.
Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
How did you emerge from what was a very difficult childhood with hope and optimism as key parts of your philosophy?