Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
Fri, 25 Apr 2025
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. There aren't many people like Cyan Banister. Her 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 everything, she is one of the most optimistic and curious people you can hope to meet. Cyan is also one of the great angel investors of this era, having invested early in SpaceX, Uber, Postmates, and Deepmind to name a few winners. She became the first female investing partner at Peter Thiel’s Founders Fund and now invests at Long Journey Ventures. 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 is also full of awesome stories about people and companies like SpaceX and Bill Murray. Please enjoy this great conversation with Cyan Banister. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by WorkOS. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit WorkOS.com to Transform your application into an enterprise-ready solution in minutes, not months. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: [00:00:00] Welcome to Invest Like the Best [00:04:06] Contrarian Thinking in Investing [00:05:30] Joining Founders Fund and Learning from Peter Thiel [00:11:15] Investing in Companies that Change Lives [00:14:00] The Importance of Overcoming Adversity for Founders [00:16:02] Personal Journey and Choosing Hope [00:20:56] Embracing Curiosity and Wonder in the Face of Adversity [00:21:20] Reconnecting with Our Inner Child [00:24:46] The Interruption and Resumption of the Conversation [00:27:20] The Power of Intuition in Business Decisions [00:32:28] The Story Behind the Investment in Uber [00:38:46] Conclusion: Following the White Rabbit of Curiosity [00:39:08] Investing in Uber: The Beginning [00:41:50] The Impact of Success: Personal Wealth and Privacy [00:50:22] The Intersection of Spirituality and Investing [00:59:34] The Bill Murray Experience: A Lesson in Presence [01:09:54] The Violin Kid: A Tale of Curiosity and Generosity [01:12:43] The Evolution of Investing: A Personal Journey [01:16:34] The Philosophy of Giving: The Universe's Return [01:17:36] The Spirit of a Venture Firm: Founders Fund [01:23:09] The Power of Integral Family Systems [01:28:41] The Trillion Dollar Question: Disrupting Hollywood [01:36:05] The Future of Artistry: AI and Creativity [01:41:39] The Power of Kindness
Chapter 1: What makes Cyan Banister's story unique?
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.
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 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.
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Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the
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Chapter 2: How is spirituality seen as an investable category?
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.
So I was talking to Justin and my partner and they said, you really should look into IFS and try it out. So then I tried it out and I went in skeptical and came out realizing, oh my gosh, how amazing is that? For people that don't know what IFS is, you basically view all your parts of your personality as there are no bad parts involved.
Every part is there to serve you, including the ones you might not like. And they come online to serve you because they're trying to defend you and protect you, yourself, that's underneath all of that stuff.
And when you start treating them as separate entities and have curiosity about them and start having conversations with them, you start to realize they're automatic processes that come online that you can then give them other jobs to do. And you can change your personality permanently for the better.
I've gotten rid of some behaviors that I thought were unchangeable through IFS, nervousness, types of nervousness, types of reactions to people talking to me and realizing that these were all just automatic functions of how I show up and react to any kind of perception or stimulus in the world. And it wasn't about the person I was dealing with. It was about me.
In general, it's usually all about how you... handle anything coming at you. A friend of mine said something really powerful to me once, which was, if people are coming with you with anything but love, it's not about you.
Do you still feel fundamentally flawed in any way?
Absolutely. Absolutely. I feel flawed. You're going to hear people talk about when they talk about spirituality, about being asleep and And what being asleep means is going back into your mechanical automatic reflexes of reacting to life and just sort of not being truly present. And if I have a flaw, it's just the flaw of being human and not realizing that I'm not being present in the moment.
And so that's something that I want to grind away at and fix over time. I think that sometimes I can be reactive to things in ways that I wish I wasn't. So I'm working on those things. None of us is perfect. I think the whole experiment of life, if you are an infinite being, let's just pause at this for a moment.
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Chapter 6: How does Cyan approach intuition in investment decisions?
And that becomes very difficult when you're trying to talk to quants or people who think about a world in data rooms and spreadsheets and wanting an answer to how you decided that you want to invest in something because you're trusting your gut or you've thought about the world a certain way, or you've been looking for this answer to appear in front of you may look
To others is if you're impulsive because you want to move quickly and they want to be deliberate and want to get in the data room and want to know more about the company.
And oftentimes at the early stages of a business, you know, very little, you know, that you've got a good founder in front of you, you know, that they have an idea and they have a shot, but all of that data is not going to be there. And so you've got two different types of investor types of minds that And that can be difficult to navigate and frustrating.
It was actually kind of soul crushing for me. I tend to like to be incredibly optimistic. And usually when you get into the quantitative realm of the world, you're dealing with a lot more pessimism. And so for me, I'm an intuitive thinker. And I think that if you're an intuitive thinker and you
have sort of a gut feeling about things and you really deeply think about the world, then early stage is probably the best avenue for you.
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.
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.
Peter gave me one of the best pieces of feedback. One of the things I love about Peter is he's so precise. He can give you like an amazing piece of feedback if you're willing to listen to it and really digest it. And he took me on a car ride one day and he simply said one sentence to me and it changed my life. And it actually led to me quitting the firm.
He said, Cyan, you're really good at feeling, but you're not really good at knowing yet. That was it. And I looked at him and I understood exactly what he was telling me. And I marinated on it and marinated on it. And I said, do I really want to know? Do I really want that skill set? Do I really want to learn these things that are so uncomfortable and unnatural to me?
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