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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: Investing Lessons from FC Seeding Uber, Airtable and Coupang | Why Pro Rata is the Original Sin in VC | Why Liquidity Has Died in 2024 | Why LPs are Pissed with VCs | The Hard Truth About Seed Fund Economics with David Frankel @ Founder Collective

Mon, 14 Oct 2024

Description

David Frankel is the Co-Founder and Managing Partner of Founder Collective, one of the best seed firms of the last decade. David has led rounds in companies such as Suno, Coupang, SeatGeek and PillPack (sold to Amazon for ~$1B). Previously, David was Co-Founder and CEO of Internet Solutions (IS), the largest ISP in Africa, ultimately acquired by NTT Japan. David has been named to the Midas List six times. In 2023, he was #11 and in 2024, he appeared at #15 on the Midas List of the world's best venture capital investors and at #2 on the Midas list of seed investors.  10 Questions With One of the World’s Best Seed Investors: 1. Reserves: Why are reserves the hardest part of venture? What have been David’s biggest lessons in how to do them well? 2. Why does David believe that pro-rata is the original sin of VC?  3. Has DPI died in 2024? Is PE the salvation for the VC exit market and liquidity? 4. Why does David believe LPs are so pissed of with VCs right now? What will change that? 5. When will IPO markets open? Are M&A markets shut? What would cause them to open? 6. How does David reflect on price today? When will he pay up and break his rules? 7. Biggest lessons for David on knowing when is the right time to sell? Why does David believe you should never sell your winners? What has David sold that he regrets most? 8. What companies returned the most to Founder Collective Funds? Uber? Coupang? Airtable? The Trade Desk? What did he learn from those mega hits? 9. What have been David’s biggest losses? How did losing the company change his mindset and approach to investing? 10. What does David believe is the future of venture capital? How can seed funds play in a world of mega multi-stage funds? Who wins? Who loses?      

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Transcription

0.109 - 24.324 David Frankel

I would say reserves and how to do the reserve thing is actually one of the most challenging aspects of venture. Still think of like pro-rot as like the original sin against entrepreneurs. You own your own destiny by minding your monthly burn. I think that DPI could be dead. LPs are looking at this asset class right now, I think, and going, where is the DPI? Those guys were just like a casino.

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24.824 - 27.886 David Frankel

One call to John a tiger, like 20 on 80, no problem.

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28.106 - 50.048 Harry Stebbings

This is 20VC with me, Harry Stebbings, and I'm so excited to welcome a dear friend and mentor of mine to the hot seat today. He is one of the great seed investors of our time, David Frankel. David is the founder and managing partner at Founder Collective, the firm with seed checks in Uber, Coupang, Airtable, Whoop, PillPack, and many more billion-dollar incredible companies.

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51.121 - 72.451 Harry Stebbings

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167.159 - 190.907 Harry Stebbings

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218.136 - 228.603 Harry Stebbings

David, I am so excited for this, man. We were literally just saying how much more special it is to do it in person. So thank you so much for joining me in person. Harry, it's so awesome to be here. I love being here with you in person in London.

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228.843 - 245.263 Harry Stebbings

Dude, I want to start on one of my biggest, most pressing concerns actually right now, which is we are seeing these massive seed rounds, like $6 to $10 million. How can traditional seed funds, $50 to $100 million seed funds, play in this new world?

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246.124 - 266.762 David Frankel

I mean, I think you still can. I'm going to appeal to the inner McKinsey consultant in you. I know it exists. But if you think of right-wrong consensus, non-consensus, you don't have to only do kind of right non-consensus, but that's where you do do well. And there's lots of ways of still being non-consensual, I think. So if you think of non-consensus, founders...

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267.202 - 283.79 David Frankel

People who come from less traditional backgrounds, people who come from secondary schools, right? That like mainstream is not going to back. That still very much exists. Frankly, founders who've had, who failed, right? You haven't done well. And like, you know, the mainstream is kind of like, wouldn't touch that. Founders who've been orphaned.

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284.09 - 300.577 David Frankel

So founders who come back and go, you know, I took money from one of those large funds. They went through the distance. They had to feel the pain, right? They said, I took money from one of those large funds. And man, like I got orphaned. They left me, they come back. So non-consensus founders, non-consensus market still.

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300.917 - 324.215 David Frankel

Everyone says you gotta be right in non-consensus, but I often think, well, what do you mean by non-consensus? So you've got, if you were really early in new markets, 2009, the best bet, like everybody was like chasing, I don't know, nanotech. Bitcoin had to have been the greatest investment in 2009. 2015, Ethereum. I know everybody is chasing DTC, right? That's where the whole market's going.

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324.275 - 345.801 David Frankel

You go Ethereum. So new markets, non-consensus, you can still do very well. And then old markets, non-consensus. Harry, do you know one of the best portfolio companies that I'm on the board of right now? Smalls. It's cat food. Dude, it's cat food. Nobody likes cats. Like dogs get all the love. DTC is dead. Nobody will touch DTC. We try to raise money for this business, Smalls, right?

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345.821 - 362.621 David Frankel

Doing 50 million ARR. Try to raise money in December. Nobody would look at us. Nobody would look at us. Because people hate cats, full stop, right? Cats get no love. And everybody then looks at like, this didn't work, farmer's market, whatever, didn't work in dogs. You can be in old markets, right? You can still be non-consensus.

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362.841 - 374.515 Harry Stebbings

Totally agree with you. I look at Bundy Olo. Like, oh, we just did a deal in a company called Aloe. Clearly there's a naming thing with restaurants. But, like, everyone's like, oh, my God, restaurants. Great. Fucking load up on that. I totally agree with you.

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374.655 - 390.63 David Frankel

When the whole swarm, when the whole herd moves in a certain direction, great. Like, seed is not dead. And so then you see the pricing adjust for those deals, correct? You do. I mean, you've still got to, like, market to market. You know, I think if you're going to be like, I want a 4 million pre, you're like totally anachronistic.

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390.811 - 410.507 David Frankel

I think there is a market and there's a market clearing price and you pay that price. But these are not AI prices. This is not AI deal where I go 5 on 20, that guy's unbelievable. Next thing, you know, I'm on a Zoom and he's in San Francisco in a hotel room and I just come off that Zoom and I say to my associate, I say, we're dead. There's going to be 100 million pre. This is real, by the way.

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410.848 - 424.857 David Frankel

What do you do in that scenario? I mean, we have to bow out. In that situation, I broke every rule under the sun and we put in a 100K check, right? I broke my rules, but we don't do that. Why would you do a 100K check then? Because I like the individual so much.

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425.197 - 430.921 Harry Stebbings

I have done that once in a career. Wow. Could I not push? If I was your partner, I would actually say, listen.

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430.961 - 438.566 David Frankel

If you're my partner, I can't tell you what you would throw at me. Because my partners look at that and they go, that was utter insanity and stupidity.

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438.746 - 458.2 Harry Stebbings

No, I would disagree. And I would say actually also there is a huge amount of social validity that comes with being an incredible brand category defining winners. Being the first round investor in Suno is so important for the next generation of Sunos. You should be in that. It's a financially good decision and you will get great brand ramifications. Yeah.

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458.68 - 470.327 David Frankel

there's a time factor here. You know, people say like, what's the percentage ownership you have to have? And I think in terms of time, there are situations where you can write a smaller check. And I think we've got to be fair to founders here as well.

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470.447 - 486.637 David Frankel

You know, if I'm writing a 100K check, I've got to be very open to that founder and saying, look, like this is the other side of the spectrum to me being on your board. But if I'm on your board, I can't write a 100K check. I can't write a 500K check anymore because you need my time and you need my interest. And this goes back to alignment.

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486.957 - 502.076 David Frankel

And so we've got to be we've got to have some kind of economic alignment. We've got to have some kind of outcome where, you know, you sell the business for 100 million, which is moonshot, as you know. And, you know, you make 50 million, but I make, you know, a million even. What does that mean to a, you know, $85 million fund?

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502.096 - 504.74 Harry Stebbings

Do you think founders understand the venture business enough today?

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505.04 - 519.026 David Frankel

I think some founders still see a name in lights and they go, I want that name beyond anything. If it's Sequoia, A16Z, Accel, you name it, I want that name. And I think there will always be a steady supply of founders who think that way.

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519.166 - 540.418 David Frankel

I don't think they understand that you're gonna, the one in 10, if you're lucky, and those stats are probably not even right, one in 10 get funded, otherwise you're orphaned or you're in a world of hurt because someone that the world thought was like, very, very serious and very smart about. You just said no to you. Go try sell against that. I think it's very, very difficult.

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540.718 - 547.944 David Frankel

To our earlier point, those founders come back to us and they say, like, I was orphaned. They don't understand that 90% don't get follow on funding.

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548.305 - 557.553 Harry Stebbings

When have you not broken the rules and you've stayed disciplined and you regret it? We spoke before about one time with me. When have you not and you regret it?

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558.033 - 575.852 David Frankel

You know, there have been times where we didn't break the rules for the best of reasons. The first thing that comes to mind is like Pinterest. The founders came to us and we had a conflict. We had a very strong associate in Zach Klein, who is the chairman of supply. We'd invested in supply. We couldn't make the investment.

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576.292 - 594.147 David Frankel

I look back and then I go like, how, you know, if you look at that outcome, you go like, how could we have, but we didn't break the rules. And I think there's like financial rules. And then I think there are rules of like loyalty and partnership where you go, that's my name on the door. And I cannot break, those are just unbreakable rules.

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594.367 - 600.252 Harry Stebbings

David, conflicts. Today, not many funds observe the rules of not investing in competitive companies.

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600.272 - 602.234 David Frankel

We're very old school, very old school on that.

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602.654 - 613.107 Harry Stebbings

David, how fast do you know when you are in a company that is not good? Wow, that is such a great question. I actually feel like you know very, very quickly. I'm saying first three months.

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613.584 - 635.302 David Frankel

So I'll give you the corollary of that, is there've been companies that I've been very down on. And often it's in enterprise SaaS, where just the sales cycle is so long and you go like, are they ever gonna get there? But I remember saying to my wife on Olo, this is done, we've lost a lot. This was pre-Founder Collective saying, we have lost our money. Like no, it is never gonna get there.

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635.682 - 653.738 David Frankel

Each time this guy gets a little bit of funding, I feel like he's just pulled the rabbit out of the hat. I feel like he's duped the investor. The corollary to that is some of these businesses take a long, long time. And so consumer, I think you get feedback pretty quickly. By the way, Harry, there've been times where I've said, how good is that entrepreneur?

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653.858 - 669.191 David Frankel

And I've started to say, they're not the smartest, they're not the fastest. The velocity of getting stuff done here is very slow. And then something lucky happens. And particularly in a consumer business, you get this fast feedback and then you think they're geniuses. But this is a long, long journey.

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669.591 - 688.02 Harry Stebbings

The one thing I've learned here is patience beyond anything else. Patience and like pain tolerance. Actually, one of my best friends is the founder of Calm, the meditation app. And he says, listen, being an entrepreneur, he told me this when I was fundraising, being an entrepreneur is just the ability to get punched in the face every single day and say, I'll come back tomorrow.

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696.365 - 696.685 David Frankel

Yeah.

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697.445 - 717.978 Harry Stebbings

I haven't heard that. But you're right absolutely in terms of consumer you see a little bit more, enterprise you see less, which is why, David, I do not do reserves. And I don't because I was in Hoppin', I was in Clubhouse, I was in BeReal, and then I've got a load of companies which were much slower in enterprise and are phenomenal investments.

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718.798 - 725.102 Harry Stebbings

But if I had reserves, I would put them all in the three companies with traction. How do you feel about reserves and that approach? Yeah.

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725.422 - 737.633 David Frankel

We did no reserves in fund one, zero. And then what we found was there was this negative correlation bias. There were these companies that just were not getting there fast enough that needed our help. And we had to break the rules.

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738.073 - 760.305 David Frankel

One of the best instances of breaking the rules, Eric, who is the most disciplined investor in our team by far, he's created literally the infrastructure on which we all work. you know, rise. Eric looks at me on Trade Desk and goes, they're out of money if we don't invest here. They're out of money. Eric breaks his own rules so painfully so for him. I'm more opportunistic.

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760.345 - 770.547 David Frankel

I go like, if we've got to do it, we've got to do it. I've got goosebumps imagining this company not existing. No reserves in fund one. And Eric invests in Trade Desk as a follow on because nobody else is going to give them money.

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770.727 - 772.268 Harry Stebbings

How much do you put in that follow on?

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772.748 - 784.398 David Frankel

It was like somewhere between half a million and a million. Whatever we did, it felt like a lot. In fund two, we created a reserve strategy because, and it was that negative correlation bias that made us do it.

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784.538 - 794.026 David Frankel

We went, if we're going to put in like another 50%, we won't lead ever, but if we're going to put in another 50%, like how do we do that only in our companies that like crave and need the money?

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794.446 - 806.511 Harry Stebbings

And why would you do that? I mean, because it's also very easy to set rules based on exceptions like that. But every other reserve that needed the money where that was the case went to zero.

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806.831 - 821.18 David Frankel

Yeah. I'll tell you what happened is we put in a reserve strategy where we said we won't fund if it's more than 20 million post. But then what happened is the market just went away with it. That became anachronistic. So you create these rules and then the market moves.

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821.34 - 838.618 David Frankel

And in a way, like what you have to do is two years later, you have to try and change those rules altogether again based on what the market's doing. So now today, how does your reserves look? We still have this kind of one-to-one reserve policy, but we actually struggle on our reserves because a lot of the time our good companies- I just don't understand.

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838.638 - 854.674 Harry Stebbings

I'm so sorry to ask, but funds are 75 million. So you have a one-to-one. You've got a 35, say, for initial. I mean, there's fees and everything. So it's 35 for initial. God, if you're doing, you've got like 25 million to checks. It's not very many.

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855.28 - 874.878 David Frankel

I'll tell you what happened, Harry. This is how this moves. During COVID, we got very scared. At the beginning of COVID, we went, oh my God, the market's going to close down. We're going to really have to fund our companies. So then we're thinking we've got to, in the first instance, put even fewer funds into our companies. And then what happens is the market just gets awash with capital.

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874.958 - 888.042 David Frankel

Everyone's day trading. And of course, we run Raise Fund 4 prematurely. So I would say reserves and how to do the reserve thing is actually one of the most challenging aspects of venture. How to get it perfectly right? Pretty tough.

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888.502 - 898.264 Harry Stebbings

It's also so tough because you are forward looking in terms of where the portfolio will be. And that is very difficult on net new investments that maybe haven't even been made yet.

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898.664 - 910.469 David Frankel

The minute I feel like we should reserve more, I almost feel like the market will go crazy. The minute I think we need to reserve much less, my sense is, oh my God, like the market is going to like, you're really going to need more money now.

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910.829 - 923.875 Harry Stebbings

The company is going nowhere and you lose faith in the founder and the CEO. Do you tell them or do you do what my friend Jason Lemkin says, which is like, that never works. Just don't bother. Just don't tell them. No one wants the hard feedback.

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924.235 - 941.445 David Frankel

Pretty forthright. I'm the opposite of Jason. And he may be right, but sometimes I think, look, whether I say something or not, you're kind of running out of money in three months time and I better say something. I feel like I'm abrogating my duty if I don't say something. Running Tide, we just closed down the business.

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941.485 - 961.072 David Frankel

This was a carbon sequestration business, literally ag in the ocean, unbelievable business. We've got $10 million and he's burning $3 million a month. I think Marty stopped taking my calls because he knew what I was going to say to him. And I said it to him anyway. I said it to him in an email. The fact is, like, at the end, he wrote it on his window in the condensation.

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961.172 - 961.492 Harry Stebbings

Exactly.

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961.532 - 962.212 David Frankel

Can't burn.

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962.292 - 962.832 Harry Stebbings

Yeah, yeah, yeah.

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962.852 - 981.952 David Frankel

I put it on the boat. I knew I had to take the boat out. And I knew that he was rolling his eyes knowing exactly what I would say. We closed the business like a month ago. Could he have cut the burn to give himself? He absolutely could have. But these founders get onto this treadmill and it's almost impossible to slow this thing down. Why?

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982.432 - 1001.838 David Frankel

I think what they feel like is their loyalty is to the team that they've put in place. Their loyalty is to the last set of capital that still says go for it. And then the same thing that makes these amazing entrepreneurs where they go like, I'll walk through walls. They go, I'm going to be the guy. I'm going to be the person that is going to pull the rabbit out of the hat in the last three months.

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1002.358 - 1010.661 David Frankel

So down to the last draw. And in fairness to them, some of these enterprise clients are still giving them hope. If you do this, this, this, you get $100 million contract.

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1011.781 - 1023.809 Harry Stebbings

In terms of those founders and that psychology, how do you see that differ in terms of, we spoke about it a little bit before, but like first time founders versus second time founders with huge Xs or failures or small Xs?

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1024.538 - 1045.003 David Frankel

I would say generally founders who've had enormous, enormous success and exits come to the next opportunity with some degree of hubris. I speak about this personally. I sold my first business and I thought I could conquer anything. And they look at any vertical and you kind of go, I'm going to disrupt that. I'm going to be the one that's going to show them a lesson.

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1045.523 - 1070.022 David Frankel

And generally speaking, that hasn't worked out well for us. Versus entrepreneurs who tried their asses off, raised money, and for some reason or another, it didn't work out. They come back hungrier. They come back, they want that prize. They want to prove, chip on the shoulder. And if they can bring back the team somehow. So second time entrepreneurs where they failed and they come back for more.

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1070.322 - 1087.032 David Frankel

Tom Lease at Motorway is an unbelievable example. I was on the board with Sonali Durekar of Top 10. They build an unbelievable product in the travel space, but they get crushed in that vertical. Try to outspend Kayak in the other place, spending $100 million a month, Google's single largest advertisers. You can have the best product you want,

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1087.412 - 1098.68 David Frankel

tail between their legs, go off, they lost all of our money. Brings back the team and starts motorway, billion dollar valuation. They're great people to back. The trick is you got to get them to come back and speak to you because sometimes- They didn't.

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1099.901 - 1100.981 Harry Stebbings

What did you learn from that?

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1101.462 - 1122.604 David Frankel

So, you know, that is to say, look, you failed for all the best reasons. You failed. It's not because you didn't try your ass off. It's not because this team isn't thoughtful. And the clock cycle, the frequency at which you got stuff done was enormous. The context was just impossible. Come back to me. My bad on steroids, right? That I didn't say that. And I've learned that the hard way.

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1123.024 - 1139.092 David Frankel

Every time there's a failure and I love the team and generally that's the nature of this business. Like, you know, I put teams before themes all the time. It doesn't work out and I love that team. Like I have to say to them, come back, please. Not because I'm an options junkie, but because I want to be in business with those people.

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1139.432 - 1158.131 Harry Stebbings

I totally agree with you. Worst question LPs ask and I get in trouble for this is, what themes do you like? I'm like, that's the most lazy LP question. Do you know one thing that I think can be quite lazy in our landscape though is pro rata. So many funds that I see and operate today, yeah, we'll just do pro rata. It's like an easy option, an easy get out.

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1158.391 - 1162.996 Harry Stebbings

I think you should be like all in or all out. How do you think about that?

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1163.356 - 1181.292 David Frankel

I still think of like pro-rot as like the original sin against entrepreneurs. You asked me earlier, is there stuff that entrepreneurs don't understand about VCs? If I said to you, Harry, I've got an option to, I don't know, you know, anything, right? Like, why would you give me a free option? Why would you give me a free option?

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1181.332 - 1202.682 David Frankel

If I said to you like, you know, for $10 million, like give me an option to buy 10% of 20 VC and I can decide if I want to do it or not. You wouldn't in a million years, right? But you've had to learn that. The amazing thing about entrepreneurs is they give pro rata. It's like the superpower thing for VCs. And I think it is terrible, terrible for entrepreneurs. You're selling options against you.

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1202.762 - 1218.087 David Frankel

So standard operating procedure is, you know, later stage VCs look at it and they go, go to the market, test the market, see what the market will bear. That's code for like, I don't want to price you, you know, go out. The market's going, I'm a stalking horse. Like, why would I be a stalking horse for X, Y, Z?

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1218.568 - 1238.818 David Frankel

And if you're doing great, if your revenues, if your rule of 20 is like, your rule of 40 is off the charts and you're doing great, amazing. Pro rider doesn't matter. If you're struggling, pro rider is terrible. Why is it terrible if you're struggling? Because you go to the market, you're a stalking horse for XYZ lifetime fund that's on your cap table already.

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1238.918 - 1259.711 David Frankel

Everybody's going, I'll price this thing, they'll come in at that price only. It's just very difficult, I think, to get deals done. By the way, then you find, unless you're killing it, So I remember, I think of Coupang and Coupang went to Sequoia and said, look, it's a 4 billion pre. BlackRock will put in a billion. You don't get your pro rata.

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1260.071 - 1279.104 David Frankel

When you're doing incredibly well and you're hot as anything, you can do it. When you're not, even the later stage investor goes, I want 20% ownership. And your cap table saying, no, no, no, no, we're doing our pro rata. And then you get into that struggle of, well, I've got to dilute more than I thought I would. So in good and bad, I don't think pro rata is great for entrepreneurs.

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1279.344 - 1298.158 Harry Stebbings

You mentioned stalking horse there. And I use that word exactly internally because I oscillate on the power of conviction and being the first to commit, being the first to show an entrepreneur, I believe in you. We often hear that's what founders love. Actually, quite a lot of the time, they use you as a stalking horse. They kind of take you to market.

0
💬 0

1298.658 - 1307.565 Harry Stebbings

And understandably, their job is to get the best round. But you can be used to get a better price, to get a better structure. How do you think about that?

0
💬 0

1307.905 - 1328.157 David Frankel

I think it's a good signal to investors early if that happens. Like, do you want to be in business with that entrepreneur? It happens to everyone. But I'd rather it happens early to me than later on because it was pretty clear that that individual was totally transactional. Josh Kopperman, there was a time where he would say, I'll give you $2 million uncapped note ahead of the next round.

0
💬 0

1328.457 - 1341.367 David Frankel

A lot of this was in his portfolio already where he went like, what's the quadrant that's really killing it? What first round used to do is in the quadrant that they thought was like amazing, they would go to those founders and say, here are literally uncapped checks.

0
💬 0

1341.467 - 1360.183 David Frankel

And what we're doing is your initial founders are showing such enthusiasm for your company that that can only be great as a selling point when you do the next round. So that's a different take on it. But I think you can do that. You can do it in the opposite direction where you just show unbridled enthusiasm. And in a way, that's testimonial marketing for the founder.

0
💬 0

1360.663 - 1375.119 Harry Stebbings

Do you think there's any other terms which you're like, that's BS? We had Nick on the show from Notation who we mentioned before, who was like, you know, we should take common, not prefs. I totally disagree with him on that one. But like you said there, pro-odd is kind of a very strange and wrong thing. Any others where you're like, that's berserk?

0
💬 0

1375.64 - 1395.199 David Frankel

I would disagree with Nick because I would say prefs are fundamental, saying you should give your investor their money back before you kind of distribute the spoils to everybody. I think that's a fair tenet. I think most entrepreneurs would go, yeah, giving them their money back is fair. I remember in Uber, by the way, we had preferred shares.

0
💬 0

1395.319 - 1414.579 David Frankel

Eric was the first investor, was one of the first in the first round on Uber. And I remember one of our LPs saying, you've got Common. And Eric went, no, no, no, they're preferred. And our investor said, no, no, you've got Common. And Eric was like, what are you talking about? Like, they're preferred. He said, well, you're under a stack of so much prefs. You're under like $5 billion of prefs now.

0
💬 0

1414.84 - 1433.251 David Frankel

It's equivalent to Common. And so I think there's another way of looking at that, of going, when companies raise so much money, if you're in the very beginning, right, do you really have prefs? You're under that whole pref stack, unless you got kind of pari passu. And I think that's changing in this environment now. How's that changing? Well, I think the terms are getting tougher.

0
💬 0

1433.532 - 1445.259 David Frankel

You know, there's so much capital out there, but later stage capital can call the shots a lot. And it depends on how well the company's performing. But when tougher performance companies raise money, the terms are getting tougher.

0
💬 0

1445.499 - 1445.619 Harry Stebbings

Yeah.

0
💬 0

1445.859 - 1451.321 David Frankel

as well. And the pref stack, like Perry Pesu feels like something of the past. There's a real pref stack coming.

0
💬 0

1451.441 - 1469.388 Harry Stebbings

I do notice also founders not adjusting. I was in this board meeting the other day and they're like, but we've done this, this and this. And so we should be double our last round price. And I'm like, I understand your rationale, but the market has moved. And it's like they can't get their head around the fact that external to them, totally, the market has changed.

0
💬 0

1469.608 - 1491.983 David Frankel

Well, the listed markets change completely. So if you look at SAS multiples in 21, 20, where that was 20X, and then you look at those SAS multiples as five, six X, that trickles down. So later stage investors that invested in private at a billion and expected that rule of 40 to be at least profits and huge growth all the time, and that hasn't materialized.

0
💬 0

1492.443 - 1514.836 David Frankel

They're looking at those same companies who are going out for top-up rounds and they're going, why would I top out at the last valuation? Or they're saying, again, go to the market, see what the market will bear. We've seen down rounds in companies that got valued enormously, hugely. Goes back to at any point, you own your own destiny by minding your monthly burn.

0
💬 0

1515.497 - 1522.521 Harry Stebbings

I love that. Can venture survive unless we get the reflation of public market multiples? So this is a great question.

0
💬 0

1522.741 - 1545.617 David Frankel

I think that DPI could be dead, right? And let me clarify that. But I think a lot of LPs look at 2018 plus funds and they go, where's the DPI? And I think that what happened there was a perfect storm. Our fund three is a 2018 vintage, no DPI yet. And what happened is if you look at fund one, fund two, five, six years in, we were giving DPI.

0
💬 0

1545.737 - 1569.256 David Frankel

It wasn't even our biggest hitters, but we were giving through companies like Cruise or Desktop Automation that you've never, Desktop Metal in fund two, right? Through companies like Datalot and InfoScout, we were already giving significant DPI. That's way before we got to Uber, Trade Desk, Coupang. And we haven't given DPI, by the way, at all in companies like SeatGeek, Airtable.

0
💬 0

1569.576 - 1595.886 David Frankel

But you look at 2018 plus funds, and the problem is it was this perfect storm. So we were preparing, we were getting involved in companies that had lots of potential. And then 2019, 2020, Zerp comes along, day trading at home over COVID. And 10 on 40, 10 on 40, 20 on 80. Tiger looks at A16Z and goes, you know, they have 10 on 40, we'll do the 20 on 80. SoftBank. And that was the apotheosis.

0
💬 0

1596.046 - 1616.1 David Frankel

But at every stage, the money was just going out like crazy. Did we do founders favors? Like, no, no, no. That's the 2018 plus vintage. So LPs at every stage, I think, are looking at this thought for LPs. And they still want to get into good funds. So they're not being as direct with the managers. But they're looking at this and going like, show me the DPI.

0
💬 0

1616.38 - 1638.253 David Frankel

Harry, we've got no DPI in fund three yet. We've got an LOI in a vertical SaaS business right now. LOI, we haven't got, this is not there yet. The company's done tens of millions. It's got a good valuation. It's PE, it's all PE. There are still PE players who are now looking at a vertical and going, I like that vertical. And they seem to be quite disruptive in that vertical.

0
💬 0

1638.373 - 1657.441 David Frankel

And I can tie them into XYZ company where I'm amalgamating a whole lot of companies and they're the tech play. So we've got PE in this company with us and they're going to ultimately sell to like a bigger PE and they've got a 1X Lickpref and they won't take, they'll literally shunt it into the bigger company because they think their outcome could be better.

0
💬 0

1657.801 - 1661.183 David Frankel

That's how M&A and DPI is going to start to happen now.

0
💬 0

1661.423 - 1676.633 Harry Stebbings

But how do we solve this? When LPs are asking you, David, liquidity, where is liquidity? How do we solve this? Because IPO markets are not opening up until age 225, I think, at the earliest would be wise to say. And then M&A markets are not open, really, I don't know.

0
💬 0

1676.653 - 1695.745 David Frankel

Yeah. You know, there's the saying, like, one swallow doesn't make a summer. And I kind of like think, no, no, no, no, no, no. One swallow can make a summer. So think about this optimistically. One good IPO and everyone will go, IPO markets are open again. I think pre-election in the US, IPOs are pretty much closed for now.

0
💬 0

1695.865 - 1717.475 David Frankel

I think post-election, one or two or three great IPOs, every single, you're going to have like the swarm of JP Morgan and Goldman Sachs bankers coming to tell you like, it is open. It needs to be a magnum. And Instacart won't do it. No. There are tons of four, five, six billion ones. SeatGeek's been IPO ready for two years. But that doesn't do it. No, that doesn't move the needle.

0
💬 0

1717.495 - 1720.076 Harry Stebbings

It needs a Stripe. It needs a Starlink. It needs a SpaceX. Yeah.

0
💬 0

1720.356 - 1722.618 David Frankel

Yeah, the minute that happens, IPO will be open.

0
💬 0

1723.018 - 1728.542 Harry Stebbings

The minute that happens, also LPs are open because there are so many LPs who have positions in those companies.

0
💬 0

1728.662 - 1749.056 David Frankel

LPs are pissed off at the moment. LPs are looking at this asset class right now, I think, and going, where is the DPI? And they did unbelievably well. And some of them are scared to sit it out. And it depends what kind of LP you are. If you're an endowment or you're like a parastatal or something, you've got to be in this asset class. And your allocation can still be tiny.

0
💬 0

1749.356 - 1752.678 David Frankel

But I think LPs are looking at this right now and going, where is the DPI?

0
💬 0

1752.818 - 1764.927 Harry Stebbings

I'm looking at the 19, 20, 21, though. And I'm in a couple of funds. You're in many funds. I don't think that it is a DPI delay in a lot of cases. I think it's a permanent loss of capital that we're actually trying to avoid.

0
💬 0

1765.367 - 1781.988 David Frankel

I think vintage matters so much. I look at our 2020 fund and I go, that's actually gonna be okay. 2018 fund, I go, I'm much more worried about that. We need DPI there. I agree with you. By the way, I think what we've seen is like the more polarization than I've ever seen in my career before.

0
💬 0

1782.148 - 1807.263 David Frankel

We've seen this completely binary outcome thing where companies are losing it and companies are doing very well. And to return these seed funds, you can't just have these huge, it's great for PR, it's great for your story to say like I was in XYZ great company, but actually fund returners, you need four or five good companies. If we sell four companies at $250 million each, we can return a fund.

0
💬 0

1807.563 - 1814.828 David Frankel

If we sell 10 companies at 100 million each, Like nobody cares about that we can return a fund. And if you don't have that, you're in trouble again.

0
💬 0

1815.268 - 1825.556 Harry Stebbings

So everyone always says, eventually you need your fund returners. This is what the business is about. Are you saying that actually that's not true? You can have these demi-fund returners, these ones that return 25, 30, 40%. Yeah.

0
💬 0

1827.077 - 1849.594 David Frankel

Look, Harry, I will be infinitely grateful to have been in Uber. My gratitude to Eric knows no boundaries. Can I ask, how many times did Uber return the fund? I mean, Uber is just in itself. Yeah, it's just it's just that's incredible. Tradesk was a bigger outcome for us. Coupang returned the fund and multiple times.

0
💬 0

1849.814 - 1863.703 David Frankel

If I look at and then we've got in SeatGeek and Airtable potential fund, you know, fund returners again in fund one. But but Harry, here's the thing is PillPack returned fund two. I am so grateful to Elliot and TJ. PillPack returned fund two. Yeah.

0
💬 0

1864.104 - 1864.344 Harry Stebbings

Wow.

0
💬 0

1864.364 - 1867.126 David Frankel

Yeah. I mean, we were in at the beginning of PillPack, right?

0
💬 0

1867.146 - 1888.564 Harry Stebbings

So we were the largest institutional pre-seed and we co-led the seed with Fred. But this is the other thing that people aren't talking about, which is like it did for you because you've got a 75 million fund. Yeah. But I know a lot of people, I love Index, they're great. But Index's seed fund is like 500 million. Yeah. 400 million? That same one returns less than 25%.

0
💬 0

1889.165 - 1901.634 David Frankel

Entrepreneurs need to do the math on that as well. Entrepreneurs need to be doing the math on that. It goes back to our point is, if you take 20 million from a billion-dollar fund, do you move the needle for that? What does it take for you to move the needle there?

0
💬 0

1902.014 - 1921.069 David Frankel

And if entrepreneurs get a $10 million check from XYZ large-scale fund, and a partner doesn't join the board, that is not a good signal. I think if a partner says, I'm putting in $5 million and I'm joining your board, right? Like everybody goes like, you know, multi-stage firms or a seed. I think there are other ways.

0
💬 0

1921.169 - 1932.238 David Frankel

If a partner at a multi-stage firm, billion dollar firm says to Harry, five on 20, and I'm going to join your board, I would say that's a strong signal. That's very tough for me to compete against. They're saying to you, I'm going to spend time here.

0
💬 0

1932.539 - 1940.225 Harry Stebbings

Like admittedly, as long as they're not on 20 boards. But are they? I mean, respectfully, I know many of these mega funds, they never show up to

0
💬 0

1940.265 - 1956.133 David Frankel

But some of them show up. Some of them show up. And I just want to give credit where credit's due. There are people who show up. Then there are people who are very disciplined and say, like, I'm not investing. Again, percentage of the fund and what it takes to return that fund is very indicative of whether you'll get time or not.

0
💬 0

1956.173 - 1964.358 Harry Stebbings

We just won a Series A, and I said, you should take our check because this is 7.5% of our fund. Right. Like, you really matter to me.

0
💬 0

1964.518 - 1971.62 David Frankel

Yeah. I think for entrepreneurs and for LPs, size of fund, check in company versus size of fund tells you everything.

0
💬 0

1972.12 - 1988.765 Harry Stebbings

Everything. What happens then to LPs? Because they continue to invest in the asset class. They're not actually pulling back. Does capital deployment from LPs change as a result of the illiquidity? It depends on who those LPs are. Endowments, pension funds. The endowments are turned off though.

0
💬 0

1989.085 - 2007.238 David Frankel

They are dialed back. They've dialed back a little. But I think they'll always go, look, we have to have 1% or 2% or 3% in VC. Oh, way more. Or more. So I'm going minimum. Absolutely. Totally. If you look at the Swanson model, VCP, it was more like 30%.

0
💬 0

2007.738 - 2025.712 Harry Stebbings

I'm getting on a high horse here. This is a big problem, though, which is they all looked at Swanson and thought, hang on, we can replicate this incredibly heavy 35%, 40% allocation. But that was in a time when liquidity was much better. And actually, your hit rate on selection was much better. Now, your hit rate is way lower and you've got real illiquidity.

0
💬 0

2025.752 - 2052.71 David Frankel

Yeah. Well, so you've seen high net worth family offices pull back even more. I think the vintage just matters a lot. And some of the large LPs will be scared of sitting out vintages. It's kind of like the Excel Fund 7 era. So I sat out and I missed Facebook. So I think sometimes if you think you're as an LP in a great fund, But you got to keep up your track record. You got to be a great fund.

0
💬 0

2052.73 - 2073.667 David Frankel

Do you mind LPs bowing out in those cases? We're so small that in some cases we welcome LPs bowing out. So in our last fund, in fund five, we had one fantastic family office. We love and adore them. Say if it's less than 10 million, we're out. And we went, it's less, your allocation's less than 10 million. They're out. Our fund's small. We don't mind.

0
💬 0

2074.067 - 2093.896 David Frankel

Harry, we spend a very, very small amount of time on fundraising. If you ask me, I spend truly 95% of my time on finding good companies and supporting good companies. I think I spend 3% of my time on fundraising. But it doesn't mean I don't care about our LPs. I'll talk to our LPs any day of the week, and I love spending time with them, but I'm not out there fundraising.

0
💬 0

2093.916 - 2113.315 Harry Stebbings

But the secondary markets then are like more alive than ever, almost to the point where it's the most obvious market to go into. And all LPs are like, we're super interested in secondaries now. How do you think about navigating secondary markets? Is it the duty of us seed funds to be very active in managing positions, portfolio exits?

0
💬 0

2114.055 - 2126.643 David Frankel

I'd say the first thing is secondary is so elusive. Like if I think of the secondary we've had over a career, I can count it maybe on two hands. So secondary tends to be in your, and by the way, do you mean companies or do you mean funds?

0
💬 0

2127.083 - 2128.304 Harry Stebbings

I mean company actually.

0
💬 0

2128.364 - 2151.158 David Frankel

Yeah. So, you know, it's elusive like in your high flyers. So in your really well-known companies, there's a real secondary market. Try to get secondary in your smaller private company. It's almost impossible. So I found secondary to be very, very difficult. Where we've done secondary, they've been pre-IPO, really high flyers, the secondary markets all over them, and then you fall off a cliff.

0
💬 0

2151.399 - 2169.651 Harry Stebbings

You mentioned the companies that raise from your Tigers and your Andreessens and your Softbanks and then have these down rounds. What happens to all of these companies with seven years of runway, which kind of aren't hitting? Are we about to see this decimation of them? Do they just kind of plateau into the unknown? What happens?

0
💬 0

2170.371 - 2190.809 David Frankel

It's funny. You think about product market fit as in the early stage only. But if you don't maintain product market fit and you don't maintain growth, it just becomes... Well, most of them never had it. Yeah. Well, the ones who didn't have product market fit, they're being abandoned. At some point, their boards start to abandon them or they just get incredibly frustrated. Yeah.

0
💬 0

2191.169 - 2210.135 David Frankel

Some of them, frankly, you know, it's at every single stage, late stage. Some of these companies have IPO'd even, right? And then, you know, you really kind of, you really know what that looks like because the market walks away from you. In some respects, being private then is a luxury, particularly if you've got a lot of money. But if you're burning it fast, it's just a matter of time, Ari.

0
💬 0

2210.435 - 2217.317 Harry Stebbings

Do you think we're seeing a generation of VCs quite quit in companies? In these companies, they just go, I'm out.

0
💬 0

2217.817 - 2218.117 David Frankel

I do.

0
💬 0

2218.137 - 2219.598 Harry Stebbings

I do. Is that a problem?

0
💬 0

2220.098 - 2240.296 David Frankel

I think it's for the entrepreneur, there comes a point where it's like you can have, it goes back to your earlier question, you can have words, you can have as many discussions. If the business is just not working out, do you expect your investors to be around? That comes back to relationship, I think. That comes back to some degree of sentimentality.

0
💬 0

2240.356 - 2260.284 David Frankel

And if you're purely commercial about this, the investors are moving on. down the whole ecosystem. Just like the LPs are moving on, they invest in those companies. If I invest in you and we're personally still involved and I'm going like, Harry's going to get this right at some point, maybe it's this abundance of faith. Maybe it's crazy and sentimental.

0
💬 0

2260.844 - 2264.965 David Frankel

If I believe in the call option of Harry may just still get this right, maybe I'll stick around.

0
💬 0

2265.445 - 2289.567 Harry Stebbings

we mentioned coupang we mentioned uber we mentioned the trade desk i love our mutual friend avi for his framework around actually selling and he broke it down on the show in three distinct parts i'm intrigued when you look at the ipos there and the great outcomes they've gone on to be do you sell when they ipo and what's your process for liquidating and how to distribute effectively

0
💬 0

2290.147 - 2310.998 David Frankel

I have to channel one of our LPs, Tim Blyamtas, who is the CIO of WeatherGage. And I remember around Uber, Coupang, some of the situations where we had shares to distribute, speaking to Tim and saying what we should do. And Tim said, whatever you do, you're going to be wrong. And of course, like the answer to that is you sell prematurely and you didn't capture the upside.

0
💬 0

2311.038 - 2330.106 David Frankel

You don't sell and think tanks and you didn't preserve value. And frankly, it gets more complicated than that. Some investors want to give the shares to their foundations and they get pissed off with you for cashing out and giving them cash instead of shares. Some investors say to you, LPs say like, I don't know what to do with that share. Like I've never heard of the trade desk.

0
💬 0

2330.406 - 2351.305 David Frankel

Why didn't you make the decision for me? The answer there typically has been with big distributions where large positions, so fund movers or it's half the fund, we distribute and we say it's up to you. With smaller positions, when it IPOs, so desktop metal, for instance, it got to the point where it was like, I don't know, worth $10 million, we sold and we take the cash and we distribute the cash.

0
💬 0

2351.765 - 2380.116 David Frankel

So I would say quantum or size versus the fund size is pretty much how we decide around that. Now, what our LPs did with their stakes, so TradeS 25X, Uber 150 billion. I don't even remember what the IPO price was. But Harry, that is, if I look back, I go like never sell a single thing. If you could, and people have to live and people have various desires, but if you could, never sell a share.

0
💬 0

2380.456 - 2391.635 David Frankel

And I know we've gone through up and the down cycle, but great companies, companies with real moats, right? Like you want to be in those companies forever. That's when we get into Buffet land, right? And like, we're not good at that.

0
💬 0

2391.655 - 2393.699 Harry Stebbings

Do you agree with Sequoia's evergreen fund structure?

0
💬 0

2394.192 - 2405.302 David Frankel

Well, I think the timing was problematic, right? Clearly. But I think the theory that they had, I'm impressed with them that they thought about that and they executed on it. I think the timing was unfortunate.

0
💬 0

2405.482 - 2409.326 Harry Stebbings

I think only they could execute on it, to be honest. Yeah, yeah.

0
💬 0

2409.606 - 2419.495 David Frankel

And then the companies still have to be extraordinary, right? So the company's in there and you could argue that they had those. So I think the strategy there was actually sound.

0
💬 0

2419.855 - 2428.464 Harry Stebbings

So we were chatting before, and when we spoke, you mentioned LEACH, and I thought it was a great acronym. What is LEACH, David? Let's start there.

0
💬 0

2429.205 - 2451.88 David Frankel

Oh, Harry, this is a subject I can keep you here all day on. But LEACH is Lethargic Economic Extractor Causing Harm. These are these legacy companies. A great example of them is the PBMs, the Pharmacy Benefit Managers. Companies that were very innovative 40 years ago. So a PBM connects the pharmacy to the insurer. You know, 40 years ago or 30 years ago, they were great companies, right?

0
💬 0

2451.92 - 2469.586 David Frankel

And the insurance codes and how much you should pay out for your meds, great. And then you have the whole internet and you've still got hundreds of billions of market cap, hundreds of billions adding no value. And the problem is that these incumbents use every trick in the book. Capitalism's so beautifully set up for them.

0
💬 0

2469.746 - 2491.918 David Frankel

So they use lobbying, they use lawyers, they use PR to say that the challenges are illegal. That's like job number one. I have had this... time and time again. And in one way I go, it's a badge of glory, right? Like to actually like rouse a leech, like unbelievable you're doing, you know, because the incumbent is now pissed off or worried about you. It's a badge of glory.

0
💬 0

2491.958 - 2498.442 David Frankel

But I think going through that, what it takes to take on these leeches is tremendously underestimated.

0
💬 0

2498.843 - 2505.687 Harry Stebbings

I remember actually TJ at Pillpack talking to me about rousing the leeches, that being a very difficult moment. Yeah.

0
💬 0

2506.594 - 2527.002 David Frankel

I'll tell you, SeatGeek, I actually gave testimony to a panel of lawyers for the Department of Justice. Russ D'Souza is the co-founder of SeatGeek. He says to me, come on a sales visit with him. So I go to TD Garden in Boston, which is like Madison Square Garden. We meet with the manager. She's awesome. She says, we turf Ticketmaster in a heartbeat and go with SeatGeek.

0
💬 0

2527.042 - 2546.671 David Frankel

We love your ticketing policy. We love the open thing. We can't give up Ticketmaster. I look at her, I go... But hold on, you're like, there's no other venue like you in Boston. This is this covered arena. It's beautiful. It's where all the basketball and ice hockey takes place. When you two comes to town, where else are they going, right? She goes, no, no, no, no, it's not that.

0
💬 0

2546.751 - 2564.239 David Frankel

She's like, Live Nation straight out said to us, you two will come to Boston. You'll have one night in Boston instead of three nights. I make like a million or $2 million net profit a night. I literally gave testimony to the Department of Justice telling them exactly what I've just told you. And what you've got is you've got, you take vertical after vertical.

0
💬 0

2564.299 - 2581.106 David Frankel

So Live Nation, Ticketmaster, that merger should never have been allowed. But once it's allowed, we will occupy, monopolize that position all day long. Harry, we've got it right now. I had it in my business in terms of taking on the legacy telcos in my startup, like impossible. And we can talk about some of the strategy around that.

0
💬 0

2581.146 - 2599.242 Harry Stebbings

Is that ever a business you want to be involved in though? When you are fighting against these monopolistic players with regulatory power, with lobbying power, with capital moats to the extreme. I mean, I've met so many ticketing companies. I remember Dice most recently. I don't know if you know them in London. I'm just like, hell no. Live Nation, I'm not going against you.

0
💬 0

2599.542 - 2607.889 Harry Stebbings

Ticketmaster, not a chance. You see it in travel the whole time. Am I really going to go against Booking, Expedia, TripAdvisor, Trivago? Fuck no.

0
💬 0

2607.969 - 2628.946 David Frankel

Yeah, yeah. We've seen this again in Suno. So Suno is a fund for company. The recording industry has just gone wild against Suno. And often it's exact same playbook. But I think this is a place where VCs can add a ton of value is it's the same playbook. So they're lobbing their ass. The recording industry like first says, you're illegal. Like what you're doing is illegal.

0
💬 0

2629.446 - 2645.687 David Frankel

And OpenAI and lots of people have that same legal challenge, although it's slightly different. So the OpenAI challenge is on the output, right, the LLM. Suno, the challenge is on the input. And Suno's going back and saying, we're training on the open internet. That's like Harry learning to play the piano and listening to the Rolling Stones. Is that okay?

0
💬 0

2646.328 - 2666.842 David Frankel

But the first thing is legal and you go, what's this actually about? And sometimes the answer is, I don't want you in business. I do not want you in the sector and I'm going to use all my heft. And then sometimes it's about like, I want my pound of flesh. But I do think this is an area where VCs, by any stage VC can add a lot of value. So if you go, look, this is going to happen to you.

0
💬 0

2666.862 - 2686.433 David Frankel

Here are, this is the way the game is played. Here are the lobbyists, here are the lawyers, here are the PR consultants, and here's how you're going to have to use your money. I don't know. It's like war. Air, land, sea. And that's how you win. So you take TJ speaking to Mikey Shulman at Suno going, this is the playbook. This is the only way you resolve this.

0
💬 0

2686.533 - 2701.251 David Frankel

Do these companies inherently need to have more cash then? They do. They do. By the way, you can have all the cash you want, you can have all the strategies you want. The first thing you need is customers that absolutely love and adore you. If you don't have customers that love you, what are you doing this whole thing for?

0
💬 0

2701.271 - 2721.787 David Frankel

So if you don't have actual, and I would say this is SeatGeek, PillPack, Suno, Like every one of those companies had customers, their revenues were increasing because, and that's why they're a pen in the ass to the incumbents is the incumbents go, oh my God, like customers are actually going there. Like what's this thing about? And usually they don't have their shit together, right?

0
💬 0

2721.807 - 2727.15 David Frankel

So the incumbent is like playing for time or just like going like, I want this to happen when I want this to happen.

0
💬 0

2727.17 - 2750.205 Harry Stebbings

I don't want this to happen to me. Do these companies not always lose? And I know PillPack returned the fund and I love TJ and so I hope I don't upset him with this. But I mean- The PBMs are still the PBMs. And yeah, Epic is still Epic. And they're still there. Booking is still booking. Live Nation is still Live Nation. Oh man, Harry, there's no fun in entrepreneurship if you believe that.

0
💬 0

2750.785 - 2755.709 Harry Stebbings

But is it not true? The only one that I can say disproves it is Spotify.

0
💬 0

2756.049 - 2775.322 David Frankel

And actually, you could say, really, what is Spotify? It's just another distribution mechanism. In some ways, that's just another way of distributing music. The recording industry, the publishers, the owners, they didn't love when CDs disrupted LPs or when tapes happened to CDs. And in a way, all Spotify, it's a Herculean outcome.

0
💬 0

2775.762 - 2799.617 David Frankel

But if you look at how much of their revenue the record labels actually take, Suno is something very, very different. This is where AI is fascinating and really interesting. It allows Harry, basically it's the breadth of your creativity. If you're creative, I will give you the most professional tools that the best DJ in the world has. You've got that on your phone now.

0
💬 0

2799.917 - 2819.591 David Frankel

This is really, really problematic. Now, is the recording industry going away? Is Spotify going? None of them are going away. In fact, in some way, the biggest threat is if Spotify does this with their incredible distribution, you've really got an interesting competition on your hand. But the incumbents don't go away, but their share of the market can change dramatically.

0
💬 0

2820.091 - 2837.991 Harry Stebbings

You mentioned sooner that obviously incredible business at the forefront of AI as well. AI is a new capital profile. You're a big ardent believer in capital efficiency and kind of small arounds and being pragmatic around that, as am I. Do you change your stance around that in a world of AI today?

0
💬 0

2838.476 - 2862.077 David Frankel

you know our view is kind of teams versus themes. And even in AI, like the teams have to get some kind of product market fit, some before. I think that can still be done reasonably capital efficiently. I think after that, if you look at the capital required to scale and to distribute, you look at like, Josh Kushner's 1 billion at 100 billion open AI. And I go, would I take that bet or not?

0
💬 0

2862.517 - 2882.002 David Frankel

All things being equal, I probably would take that bet. If you said to me, you have to, are you for or against? I would say, is Josh in the winner there going to make 2x and maybe much more than that, but bet against the 2x? I wouldn't bet against the 2x. I think his LPs will make 2x on that. But at some point to play in that, that's a whole different world.

0
💬 0

2882.102 - 2902.073 David Frankel

If you want to play in the hyperscaler game, wow. you're going to need ridiculous amounts of capital. And by the way, we're seeing like what's a TLM, like tiny language models, which run on the mobile phone, basically make things like scanning or translation very realistic and on your phone, even when you're not connected to the internet.

0
💬 0

2902.433 - 2910.778 David Frankel

You need capital for that as well, because the programming overhead of that, the number of engineers you need to create something tiny is huge.

0
💬 0

2911.398 - 2919.424 Harry Stebbings

With that in mind, How do you think about navigating AI seed rounds today? Because all the AI seed rounds I see today are just crazy competitive and crazy priced.

0
💬 0

2920.205 - 2939.641 David Frankel

We're off-piste. We're non-consensus. We're contrarian. So when I see those rounds, if I see a round at 5 on 20, that's in our hitting range. When I see those rounds at like 25 on 100, pretty much we're out. We're pretty much out. Again, team versus theme. So there are rare instances where we see someone who's just like, you cannot ignore.

0
💬 0

2939.661 - 2951.945 David Frankel

You wake up in the morning, you go, oh my God, like, how can I not be involved? But for the most part, 99% of the time, we're not involved. But you just can't make money in a seed fund, those numbers. I don't see how you can make money.

0
💬 0

2952.461 - 2974.089 Harry Stebbings

It becomes open AI. I'll tell you, I was one of the first investors to meet Mr. Al. Yeah, of course. And the first round was at like 250, I think. And I said, there's no way. Did you write the check? No. And I said, there's no way that I, as a seed manager, can invest in 250. Well, it goes to 5 billion. And with dilution, which there will be a lot, because I'm going to get what?

0
💬 0

2974.389 - 2976.97 Harry Stebbings

But what if it's a 50 billion company?

0
💬 0

2977.355 - 2998.155 David Frankel

Yeah. Overall, I admire your discipline. I think rear view mirror on this, you can't build a fund on this. Rear view mirror, you can think about that one that you missed, and they're one or two in a generation. There are these generational companies, or maybe there is one a year. And if you're in that company, awesome. But can you build a fund strategy? I don't think you can. Not at Seed.

0
💬 0

2998.496 - 2999.697 Harry Stebbings

But you can break the rules.

0
💬 0

3000.171 - 3021.322 David Frankel

Well, if you break the rules and you're right, you've done unbelievably well. By the way, again, if you broke the rules and it was a 10 post and you broke the rules and it was like, you know, 250 million post, like the return to you and your fund is infinitely different. So I think you break the rules and you get right on 250 million post and you get a 10X, That's why I go Josh on a billion.

0
💬 0

3021.962 - 3037.355 David Frankel

If he makes two X there and you go like, that is the company. That is the company. Would you bet against OpenAI right now? No way. So it depends on the customer base for OpenAI. If they distribute well and more and more people say, look, ChatGPT, it's on my phone, download that, start using that.

0
💬 0

3037.395 - 3057.225 David Frankel

Like, you know, when my wife and my kids start to use it and like go, oh my God, like I'm going here before Google. I'm not sure that Microsoft can think of it only as their plaything. If people are leaving OpenAI and OpenAI is not scaling and not creating more and more revenue, you may be right. But if OpenAI continues to grow the way it is, I don't know that Microsoft can ignore them.

0
💬 0

3057.505 - 3076.547 David Frankel

I think in some ways Microsoft are going to have to say, this is terrible because we wish we owned 100% of it, but this is our play. And who knows? The next thing could be a merger between OpenAI and Microsoft. I don't know that they want that. I think there's a lot of regulatory heat around this that you may kind of do well to avoid at the very beginning.

0
💬 0

3076.912 - 3083.015 Harry Stebbings

I've been insanely impressed by perplexity, I have to say. I don't know if you've used perplexity as a product. I haven't. Oh, my God. It's a phenomenal product.

0
💬 0

3083.296 - 3089.739 David Frankel

I start now. So I have a range of tools. But if you say to me, where do you start? I start on ChatGPT. I don't go to browser. That's where I start.

0
💬 0

3090.099 - 3099.985 Harry Stebbings

Do you think AI will create a generation of new unbelievable companies with huge market caps? Or do you think it will consolidate power into existing huge market caps?

0
💬 0

3100.273 - 3113.41 David Frankel

I think there's short term and long term. So I think in short term, we're going to be, you know, underwhelmed right now. I think if you look at like the amount of CapEx that's being spent and you look at the actual earnings that will be generated in the short term, there's just no way it makes sense.

0
💬 0

3113.43 - 3116.995 Harry Stebbings

David Kahn at Sequoia, it's a $600 billion AI question, which is exactly that.

0
💬 0

3117.395 - 3135.886 David Frankel

And I think, by the way, all the way through the ecosystem. So it's not just the hyperscalers, right? It's like downturn. David said it well, like down to the data centers, down to the steel, down to the chips. I think in the short term, it's going to disappoint. I think in the long term, Harry, every one of these waves, by the way, it reminds me of like self-driving cars.

0
💬 0

3135.926 - 3146.532 David Frankel

I remember taking a bet with Eric and he said, self-driving cars in five years. And I said to him, the last 5% is very difficult. And like, we're getting to self-driving cars now. So it takes forever to...

0
💬 0

3146.792 - 3150.315 Harry Stebbings

But it's one of those ones where suddenly, suddenly, and then boom, suddenly Waymo's there.

0
💬 0

3150.335 - 3171.289 David Frankel

And now it's like Waymo, if you get into a Waymo in California, like your mind is blown. So I think to discount AI in the next 10 years, man, you've got to be crazy. Like I think it's going to have profound, profound changes. The difficulty is it's always Hollywood. There'll be one in a thousand. companies that will be off the charts and there'll be like one in a hundred that's amazing.

0
💬 0

3171.589 - 3194.475 David Frankel

And that will launch so much capital. Being involved in that, we're too disciplined to be involved in figuring out which is the one in a hundred. I remember this with Eric, and this is just like the height of humility. An LP at one of our annual dinners leans conspiratorially over the table and says to Eric, how did you know? Talking about Uber, going like, how did you know?

0
💬 0

3194.955 - 3213.765 David Frankel

I literally see this in my mind's eye. And Eric looks at them straight in the eye and goes, I didn't know. The company before, it was so easy in that moment to retrofit how smart I... And he said, I had no clue. He said, the company before was just as interesting and the company after, he said, I had the same high hopes. And I think we're not smart enough to figure out the one.

0
💬 0

3214.126 - 3220.329 David Frankel

You've got to be around and you've got to hoist a flag and say, I'm interested in these great teams. We don't know how to do this.

0
💬 0

3220.529 - 3239.502 Harry Stebbings

What I'm impressed by always with you is your humility. I mean, I don't know. Yeah, dude, but not many have the number of hits that you do. You can say I don't know when it's the one out of 50 that's a hit. But when you have the trade desk, coupang, air table, Uber, I mean, this goes on and on. Huge credit to Eric.

0
💬 0

3239.742 - 3244.885 Harry Stebbings

You could say, well, the data shows that you do have a higher probability of knowing than anyone else.

0
💬 0

3245.526 - 3271.287 David Frankel

You're reminding me again of Eric, right? Where Eric has this lens. It's so simple. We look at a company and go, can we 10x that? Can we 10x? And if we can't 10x... then we shouldn't invest. And I think that is alignment with the entrepreneur. So much flows from that, like the economics, the size of the deal, the size of the valuation. If we can't, with high conviction, 10x, we shouldn't invest.

0
💬 0

3271.607 - 3273.949 David Frankel

That's how we create the alignment. That is Eric's rule entirely.

0
💬 0

3273.969 - 3280.778 Harry Stebbings

A lot of venture investors would say, for a seed investor to think that, that's a low bar. You need to think bigger. How would you respond to them?

0
💬 0

3280.818 - 3285.58 David Frankel

Small fund, you can do that. Small fund, four companies at 10x, we return the fund. Easily.

0
💬 0

3285.601 - 3299.512 Harry Stebbings

Do you know what I would respond as well? Go and read Bessemer's memos because every memo for big companies, whether it's Snap or whether it's Procore or whether it's Shopify, Every great company, you underestimate the size of your winners.

0
💬 0

3299.932 - 3311.268 Harry Stebbings

And so by thinking that, actually, you do not lose the amazing Olo, which will do great returns, the amazing PillPack, because you needed the $20 billion company.

0
💬 0

3311.488 - 3330.621 David Frankel

I just think it's insanity. I think you market those winners. And again, it's great PR fodder. It's great to attract the investors in the next fund. But I think it's insanity to go. It's like that huge... People don't even use the word unicorn anymore. It's that huge company or bust. I think it's insane. By the way, I also think it's boring.

0
💬 0

3330.901 - 3345.449 David Frankel

It doesn't take you in a whole range of fascinating directions where at the beginning you go... Look, these guys are crazy. But could this be a 10x? Yeah, it could be a 10x. I think that just provides this much easier on-ramp into these very interesting situations.

0
💬 0

3345.469 - 3356.134 Harry Stebbings

Do you think about downside protection when you come into companies? Just in terms of, listen, they're really smart operators in payments. Bad day, stripe or buy them. That's the one thing I don't think about much.

0
💬 0

3356.454 - 3376.799 David Frankel

But I think it's the most unfair feature of capitalism, Harry. The most you can lose is all your money. The most you can make is 3,000x, unlimited. If you just look at that, it is such an unfair feature of capitalism. And my LPs maybe go, I don't want to lose money for anyone. But I sometimes think exactly the opposite.

0
💬 0

3377.139 - 3398.87 Harry Stebbings

If we're not losing, are we taking enough risk? Listen, I had Shardul on from Index the other day. And I asked him, what's your biggest loss and what did you learn? He actually went like, I haven't really lost a deal. Now, I pushed back and I said, have you taken enough risk then? I mean, to be fair on him, he's got data dog and whiz. Like, yes, he's got it.

0
💬 0

3398.97 - 3402.292 Harry Stebbings

But my question to you is like, what's your loss ratio?

0
💬 0

3402.492 - 3413.96 David Frankel

I don't even know what it is now. We have definitely lost companies. And we've lost, you know, there's good losses and there's bad losses. The bad losses are where you look back and you go, my judgment wasn't good.

0
💬 0

3414.26 - 3415.461 Harry Stebbings

When it's off, why is it off?

0
💬 0

3416.161 - 3431.666 David Frankel

So if I look back and I go, I love the what, I never really loved the who, I've really learned this the hard way. It's, Koppelman called them, are they like red button or green button entrepreneurs? They call it like 7 p.m. just before you're having dinner with your family, do you take the call?

0
💬 0

3432.046 - 3446.071 David Frankel

Well, if it's you and I go like, I love this guy, I'm taking the call and I'll say like, I'll call you back after dinner. But if it's red button, oh, you made a mistake. I look at that and I go, do I want to have lunch or dinner with that entrepreneur? That's a big mistake for me. When I look at it and I go, I fell in love with the what?

0
💬 0

3446.491 - 3463.818 David Frankel

Like I fell in love with the what, but I really didn't love the entrepreneur at the beginning. And I wasn't, you know, the chemistry wasn't there. That's a mistake. When I look and I go, look, that was just such an extraordinary entrepreneur. That person was so compelling. I was so energized by that person. And, you know, the context was wrong. We were too early.

0
💬 0

3464.199 - 3473.562 David Frankel

Like we gave it our best shot, but the incumbents just killed us. I never look back at that and go, that was wrong. I look back and I go like that comes, you chop a lot of wood, you're going to get splinters.

0
💬 0

3473.802 - 3495.727 Harry Stebbings

I love that. You know, there was one great piece of advice that I was once given by a guest who will remain nameless because he's very, very confidential. I'll tell you afterwards. But he said, Harry, if you're ever willing to take less in a deal, don't do it. So if ever you have 1.25 allocation and you're like, oh, I'm fine to take one, don't do it. Do you agree with that?

0
💬 0

3496.107 - 3516.972 David Frankel

I think it's a great test. I'm very impressed. Sometimes if you love the deal and there's heat for the right reasons, to take a smaller amount is doable. So I think the problem with that comment is it ignores the context and the context matters. So in a vacuum, that's a fine comment and I agree with it.

0
💬 0

3517.412 - 3535.459 David Frankel

But in the context of there are lots of other people interested, including some collaborators, you may go, I actually want them in this deal with me. And by the way, that is under pressure when people have got funds that are too big and the deals and there's less collaboration. But I think there really are people who you want alongside you because they're smarter and more experienced than you.

0
💬 0

3536.02 - 3539.661 David Frankel

If you're having to throttle down a little bit for that, I have no problem with that.

0
💬 0

3539.701 - 3549.488 Harry Stebbings

Do you think he correlates to deal quality? No, not at all. Yeah. This is my, I look back at the fund portfolio in particular, hottest deals, the worst, the five on 25s that were the hottest, the worst.

0
💬 0

3549.668 - 3567.1 David Frankel

In fact, in an ideal situation when there's insane heat and something that we've gotten earlier, like that's a great moment to take secondary if you can. Sometimes you can't. But if I speak to teams about this all day long, so like. You've got a billion dollar valuation and you're doing 50 million or 40 million revenue. Forget like you're losing money.

0
💬 0

3567.52 - 3585.028 David Frankel

This is an awesome time for you to take some money off the table. And in certain situations, we've had the founders say to us, look, there's a little leftover because there's such heat here. There's 20 million to go between, do you want to take some money off? And we have been able to take a third of, but do we get that right all the time?

0
💬 0

3585.068 - 3596.251 David Frankel

Well, the answer was, you only know that in the rear view mirror. I won't mention the name of the company. We did take a third off the table. We were right over there, but we've got it wrong as well. We took secondary in some of our biggest names. We shouldn't have sold a share.

0
💬 0

3596.638 - 3598.379 Harry Stebbings

Which one do you most regret selling a share in?

0
💬 0

3598.499 - 3609.546 David Frankel

Well, Trade Desk, I regret every single share I sold. Uber, I regret every single share I sold. Hindsight is just the most precise science. These are great moat companies. Why would you bet against those?

0
💬 0

3609.666 - 3621.174 Harry Stebbings

You mentioned the secondaries. We've had founders demonized over the last few years for taking secondaries, especially as the tide has turned. How do you advise founders on taking secondaries, right amount to take, when to take them? How to think about that?

0
💬 0

3621.867 - 3637.243 David Frankel

My rule of thumb is there's a hot big deal going down. Again, this feels anachronistic because this was happening on steroids three, four years ago. I'm seeing less of it. But if you take less, 10% or less off the table, nobody's going to really mind too much.

0
💬 0

3637.964 - 3657.53 David Frankel

If things go south later on, then LPs look at it and investors look at it and go like, I wish Harry didn't take $5 or $10 million off the table. But I don't mind if Harry took a million or two million. By the way, I always say the first million dollars, like when the first million dollars makes, it's binary, it makes all the difference. It's partially selfish.

0
💬 0

3658.25 - 3675.397 David Frankel

It sounds like I'm so generous in saying, take as much money as you want, but it's actually very self-serving as well. If that founder's going home and worrying about the mortgage and under pressure from their wife or husband or whatever it is or partner, we alleviate that pressure in giving them secondary and encourage them to take secondary.

0
💬 0

3675.717 - 3686.702 David Frankel

So I'd say it's self-serving for the investors as well. Next thing you've taken some secondary, the mortgage or whatever the issue is. And of course, if you're like in your early 20s and you don't have these problems, the context matters.

0
💬 0

3687.142 - 3704.455 Harry Stebbings

But I am pissed off and I'm pissed off with growth investors who were shoveling cash down founders' throats in the good times and are now going, I can't believe all these founders that took all that money off the table. You fucking shoveled $30 million down their throats. And quite rightly, they said, fine. Yeah.

0
💬 0

3704.795 - 3726.958 David Frankel

Yeah. We had this. The biggest sin of the last era has been the huge amounts of capital. These like boatloads of capital. I'm going to meet later with Sam Franklin from Otter. Great founder. Lovely business. And I remember. The other investors were talking about 10 on 40, right? Like one call to John a tiger, right? 20 on 80, no problem.

0
💬 0

3727.298 - 3740.382 David Frankel

And Sam at the moment thought I was like the superstar investor of all times. He was like a seed investor across the, biggest name investors involved there. And like in a second did that. In retrospect, what a sin, what a sin.

0
💬 0

3740.862 - 3741.842 Harry Stebbings

What for him to do that deal?

0
💬 0

3741.883 - 3747.265 David Frankel

What a sin even for me to like, and I was caught up in the moment, but to... So he called me on that deal.

0
💬 0

3747.305 - 3766.715 Harry Stebbings

Yeah. And I told him, even though I lost the seed in that company to Local Globe. Yeah, we co-led the seed with Local Globe. Fuck it. Saul showed it to me and said, we need someone across the ocean. And it moving swiftly on. But I remember I said, don't do it. Yeah. Fairweather and Busters.

0
💬 0

3766.935 - 3783.864 David Frankel

Yeah. Oh, man. Those guys were just like a casino, right? Like it was insane. John was doing, I kid you not, we did a 20 on 80, two weeks. We did one the one week and we did one another week. And Otto was one of them. But in retrospect, you go... How do those founders know what to do with that money?

0
💬 0

3784.084 - 3800.972 David Frankel

And they have that money and they're going, no one would have like expanded in the US if you didn't have that money. But you go and you open an office in the US and you go, before your model's working beautifully in the UK, you're trying it over there. So the sin, like the last era, like the boatloads of capital, like that's the sin of the era.

0
💬 0

3801.092 - 3804.254 Harry Stebbings

But I don't actually think it's changing that much.

0
💬 0

3804.874 - 3825.191 David Frankel

I think it's the haves and have-nots. So I think if you have AI, right, like it's changing. I think, again, if you're a vertical SaaS company doing $50 million, right, the multiples or the listed multiples are constraining you. You're not getting a 20x multiple, dude, because that listed company that I own shares in is at 6x, 7x. That's the multiple.

0
💬 0

3825.471 - 3831.876 Harry Stebbings

I see this as my opportunity, though, because you're absolutely right. But this means everyone's kind of moving out of vertical SaaS thinking that it's not attractive.

0
💬 0

3832.356 - 3847.961 David Frankel

And the fascinating thing there is like, it's like goes back to the Andreessen, you know, like Andreessen said, software is eating the world. Like I have this, like the haves and the have nots around data. And you look at some of these vertical SaaS companies or horizontal SaaS companies, the truckloads of data they have, it's theirs to lose.

0
💬 0

3847.981 - 3867.032 David Frankel

So Mark Benioff, Salesforce, you write that off at your peril because the amount of data they have, they throw in these AI tools, they're doing their own stuff, right? Their opportunity is enormous. And I've seen this in some of our vertical SaaS plays. If we give the customers enriched data, if we don't enrich the data, we're out of business.

0
💬 0

3867.352 - 3877.32 David Frankel

But we enrich the data we have, and you look back, you're like, whose opportunity actually is this in terms of AI? If you've got data and you drop the ball, only blame yourself.

0
💬 0

3877.7 - 3898.315 Harry Stebbings

Listen, I totally agree with you. I think the subsequent question though for me is, does AI mean you can increase the price you charge per seat or just maintain your position and have denigrated margins? It's a great question. Because I had the CPO of Canva on the show and he said, oh, we're doing all these amazing things with AI. And I'm like, you're fantastic.

0
💬 0

3898.415 - 3911.22 Harry Stebbings

But he mentioned the margin denigration that happens with every query. Yeah. And then they announce a 300% price increase. It's an amazing tool. I'm sure people will pay for it. Great. But will we see prices increase or will we see margins?

0
💬 0

3911.24 - 3931.045 David Frankel

I think short-term defensive. Short-term defensive. If you enrich that and you're the one to do it and you retain your customers and because of the enrichment, you increase your revenues and you increase your customer base. Look at the great companies. Tesla, I don't know. Look at Netscape, right? At some point, freemium. It's like freemium on steroids.

0
💬 0

3931.485 - 3938.03 David Frankel

I think the right play is defensive to start. And then once you retain those customers and you've enriched the data, I think there's a lot you can do.

0
💬 0

3938.05 - 3951.359 Harry Stebbings

So you don't agree with, say, the David Friedbergs or the Deleons who say that AI means that companies will be able to build their own vertical solutions tailored to their specific needs and actually will see the end of vertical SaaS in that way.

0
💬 0

3951.379 - 3962.223 David Frankel

I don't agree with that. I think some of the tools are actually very commoditized. So I think that the vertical SaaS or horizontal SaaS or data owners will be able to access the underlying tools reasonably cheaply at some point.

0
💬 0

3962.523 - 3980.369 David Frankel

And you may disagree with that, but I think if you look at some of the open source software around this, it's going to become more and more commoditized, the underlying tools. So you could go and say, well, why can't every single company do that? I don't think you can, but I think there are going to be software providers that enrich their tool set that are going to do unbelievably well.

0
💬 0

3980.649 - 3992.695 Harry Stebbings

we drastically overestimate the technology sophistication of these companies to be able to build with AI their own vertical solutions. Are you kidding me? They struggle to onboard Slack.

0
💬 0

3992.775 - 4012.366 David Frankel

Yeah. You remind me a little bit of when I started our ISP with my co-founders and we went to like the biggest banks and we offered them internet service and hosting and all sorts of like e-commerce options. And then we went to like the national kind of railway owner and they said, look, I've got a network. I own a network. I've got fiber on every single railway.

0
💬 0

4012.606 - 4027.156 David Frankel

I own a network that like just dwarfs you, right? I can do all of this, like what I need you for. And I remember like, it was like, okay, like walk out, right? Six months later, they'd done nothing. You know, a year later, they're done. Two years later, the answer is there'll be the short-term thing where again, everybody goes like, I don't need you.

0
💬 0

4027.496 - 4033.08 David Frankel

Like, is there a business in terms of smart software solutions? And yeah, that's all over the place still.

0
💬 0

4033.32 - 4045.724 Harry Stebbings

There's one final thing I want to discuss, which is boards. I spoke to so many friends of ours, founders that you work with. You're a phenomenal board member. I've actually sat with you on a board and you're, again, fantastic.

0
💬 0

4046.164 - 4046.584 David Frankel

Too kind.

0
💬 0

4046.804 - 4050.165 Harry Stebbings

What's your biggest advice to me on how to be a great board member?

0
💬 0

4050.575 - 4067.746 David Frankel

Well, I think you have to have that economic alignment to start off with. So I don't think you should ever take a board seat where you own too small a percentage or the size of that potential outcome vis-a-vis your fund is too small. So I really think you have to have that economic alignment because it means every time you sit down, it's like us.

0
💬 0

4067.986 - 4072.209 Harry Stebbings

For a founder to know what is economic alignment, what would that be just broad range?

0
💬 0

4072.998 - 4095.883 David Frankel

Look, if you kick off and you own on a board less than 15% of that company, I think it's problematic. Certainly in terms of our fund structure, the capital and the cash is infinite in a way, or has been in this era. Your time is not infinite. And at some point, you're gonna think very seriously about your time. To be patient, you need that economic alignment with the founder.

0
💬 0

4095.903 - 4119.148 David Frankel

So if the founder owns 95% and you own 5%, problematic. Every time you sit down, you go like, I'm working for this guy. de facto. If there is more alignment in terms of ownership, then I think it works better. Harry, if things are going like ballistically, then it doesn't matter. So that always breaks the rules. I'm talking about 99% of the time. You've got to sit down and go, it's our company.

0
💬 0

4119.468 - 4120.388 David Frankel

We're in this together.

0
💬 0

4120.808 - 4125.429 Harry Stebbings

Biggest lesson on dilution. I think people forget the impacts of dilution today too often.

0
💬 0

4125.811 - 4146.308 David Frankel

We don't think about dilution much. We really don't. Our MO has been we dilute alongside the founder. As a seed stage fund, we get involved at the beginning and it's been a strategy and we don't think about dilution. We think about time and we love the alignment of coming in very early and hopefully being economically aligned with the founder.

0
💬 0

4146.708 - 4164.023 David Frankel

And then it's the exact same strategy, exact same thinking is we'll dilute alongside the founder. By the way, I can't afford in my fund If I've done my job right and you are, you know, raising your next set of capital at 3x or 4x, I just can't afford to actually maintain my percentage ownership.

0
💬 0

4164.363 - 4178.455 Harry Stebbings

And there's also the times when the opportunity cost of capital is so real that to continue to sustain that is just not a worthwhile position. So I completely get you that. Vinod Khosa says very interestingly that 90% of VCs detract value. Do you agree? Yeah.

0
💬 0

4178.843 - 4200.518 David Frankel

In a career, I've been through one bankruptcy, one bankruptcy. So in hundreds of investments, I've had one bankruptcy. And Micah Rosenblum, my partner's father, Lou Rosenblum, was one of the best bank, he's out of Chicago, one of the best bankruptcy lawyers. And I remember thinking, oh my God, I do not know what has hit me here. This is like a freight train.

0
💬 0

4200.558 - 4219.868 David Frankel

There was an enormous fraud in the company. The CFO committed suicide. The CEO is still in jail. I mean, like huge story, right? Like they were literally fraudulently putting KPMG on fraudulent financials. I remember that moment when Micah said to me, Lou's going to take you under his wing. I'd been paid out a couple of million dollars.

0
💬 0

4220.129 - 4236.257 David Frankel

The first thing Lou said to me is, you're going to give back every last cent. You're going to be the first person who gives back all the money and all the other investors are going to hate you for it. But that's the first thing you're going to do. So I had taken secondary. It was four XR investment on the secondary, gave every cent back. But here's the thing.

0
💬 0

4236.618 - 4258.279 David Frankel

The degree to which I felt taken care of by this guy who was an expert, I think sometimes... And I think he felt great that here was this helpless capitalist hit by a freight train in terms of this bankruptcy. If we can do that once in a while, the joy of that, right? Sometimes... This is about financial returns, and it sounds like completely ridiculous to say it's not.

0
💬 0

4258.339 - 4264.864 David Frankel

But sometimes the gift of that, right, and the chemistry that that unlocks, you know, we'll do every company together after that.

0
💬 0

4265.164 - 4273.651 Harry Stebbings

You mentioned the word fraud. I think there are so many more frauds in portfolios that people are not talking about. Do you think there are a lot more frauds that no one is saying?

0
💬 0

4273.691 - 4276.973 David Frankel

I think they could come out. Harry, I think the era gave rise to that, unfortunately.

0
💬 0

4277.213 - 4283.338 Harry Stebbings

There's so many brands that are around this. Is there anything you feel we haven't discussed about the world of venture that we should?

0
💬 0

4284.052 - 4296.92 David Frankel

I was thinking about this. I actually just wrote down matchmaker here. Like the small fund versus the big fund. And the concept of like the big fund, the lifetime investor fund really has no incentive to matchmake for you. They have this incentive.

0
💬 0

4296.94 - 4297.801 Harry Stebbings

What do you mean by this? Sorry.

0
💬 0

4298.101 - 4311.549 David Frankel

Okay. So when you're a small fund and you're not going to invest round after round, right? Like whole MO is make introductions all day long. If you think of like a lot of what I'm doing is making introductions to other funds. I'm like a glorified matchmaker.

0
💬 0

4311.849 - 4332.807 David Frankel

So some of the thought over there was, what's the difference between, and maybe it's stage specific funding, but like what I get from you, what I get from Sequoia. Well, Sequoia will never ever send you, will never matchmake for you. Sequoia will, if you take your check from Andreessen, Sequoia, Axel, you name them. They will never, they have no incentive to matchmake.

0
💬 0

4332.947 - 4351.276 David Frankel

They have no incentive to take you to another fund at some point because at every stage, right, they either want their pro rata and they want their pro rata. This is the difference between kind of totally financial investors. And I'd say a lot of the ecosystem has become that. It's like, I have my pro rata. Let me wait for you and go to the market, whatever.

0
💬 0

4351.696 - 4368.171 David Frankel

And if you're hot, I'll invest at the market clearing price. And if you're not hot, I'll get a deal. And otherwise, I'll just won't invest at all. Or orphan you. Right? So it's basically like call option time all day long. Whereas if you look at us, if you look at seed funds, a whole incentive is to get you funded.

0
💬 0

4368.551 - 4381.724 David Frankel

Harry, I promise you, I imagine a lot of your time is like, oh, think about that fund. Think about that fund. Think about that partner. To the point that over 15 years, we've operationalized this. Like our software, I don't care if you use Monday, Airtable, we use Airtable.

0
💬 0

4381.884 - 4393.891 David Frankel

But our Airtable and the number of people in our organization who are just like full-time dedicated to this, to like finding you not to the right fund, but find you to the right partner, right? All we do, like I'm like a glorified matchmaker on steroids.

0
💬 0

4393.911 - 4407.158 Harry Stebbings

That's all I do. But advice to founders, you need to have a seed partner who knows the specific partner at the firm because it falls through the cracks and you go to die there. You need to know that it's- Alex Tauszig of Lightspeed.

0
💬 0

4407.298 - 4426.382 David Frankel

Totally. So you need the science and you need the art. You need the science of going, I'll take you to the right partner. Because of course, hit rate with the wrong partners and happens all day long is like, Harry's busy, you're on a deal, you're not that particularly interested in that vertical or whatever, done, finished. But there's the art as well, right? And ideally, this is sales, right?

0
💬 0

4426.402 - 4438.529 David Frankel

This is testimonial sales. I'm saying Harry is awesome. Harry is awesome. Like it's not Harry going, oh, I'm awesome, right? It's me saying Harry's awesome. And by the way, I have to believe that for that to be really authentic.

0
💬 0

4438.569 - 4449.458 David Frankel

So that's why like our testimonial sales with our better companies, with our companies that are performing are better than, you know, when we're trying to kind of sell a company that's not performing. So it comes down to performance.

0
💬 0

4450.118 - 4470.952 Harry Stebbings

I do think there's also incentives that founders don't see, which is, especially on structuring rounds, people will bring in people who are maybe not the best fit for the company, but they owe them for a deal that was done before. Or they want to curry favors with people. I see this a lot where I'm like, hey, hey, the head of growth at Revolut is a better angel than this random person.

0
💬 0

4471.432 - 4479.778 Harry Stebbings

But the founder is being pulled along by the VC who owes them a favor for a deal that they sent them last time. And I don't think founders see a lot of that.

0
💬 0

4480.359 - 4499.498 David Frankel

It depends on the context again. It depends on how hot the deal is. I think you're describing a hot deal in a tougher time, like halitosis is better than no breath at all. So, you know, like if you're doing your buddy a favor and that person's putting $5 million into my deal and I have struggled to fundraise, like bring it on.

0
💬 0

4499.918 - 4501.359 Harry Stebbings

I totally agree with you.

0
💬 0

4502.16 - 4520.513 David Frankel

I've never heard that statement before. Do you do market sizing? We do. I've seen a bunch of times where funders will look at TAM and they'll walk away from a deal and they'll say because the TAM wasn't big enough. One of my favorite examples of this is MediaRadar. I was in it with Bain Capital, pre-founder collective.

0
💬 0

4520.833 - 4542.064 David Frankel

It's one of the biggest vertical SaaS plays, if not the biggest in the world in media now. How much is it worth? It's worth billions today. It's another company I wish I'd stayed in. Todd Kreiselman. Unbelievable business. So we showed it to, I don't know, Bain, Flybridge, Bessemer. I remember this like it was yesterday. The Bessemer team did all the market sizing.

0
💬 0

4542.104 - 4561.654 David Frankel

They went newspapers and magazines. That's dying, right? The damn shit. Couldn't really argue with them. Like just kept going. I'd looked at newspapers and magazines as the angel investor and gone, you know, so that's a couple of hundred million dollars, not billions of dollars. Okay, next thing media radar goes into Facebook, Google, everything online needs them.

0
💬 0

4562.014 - 4580.165 David Frankel

Next thing they're going to Netflix, Apple, Amazon, everything that is being screened needs them. And the TAM just was like infinite. So I've seen the mistake made where you really undersize the TAM. It sounds very seductive and logical in the moment. But like, do I think of TAM? TAM matters.

0
💬 0

4580.585 - 4599.778 Harry Stebbings

But when you're starting out- I don't think it does matter, actually. I really don't. I think the difference between a $1 billion founder and a $10 billion founder, or sorry, $1 billion company and $10 billion company is a truly great founder who can do a great second night. I agree. And honestly, if we're coming in at sub 20, and especially when you've got the heuristic of a 10X, who gives a shit?

0
💬 0

4600.118 - 4603.6 Harry Stebbings

And really great founders find markets. I agree with that.

0
💬 0

4603.76 - 4620.45 David Frankel

I think all things being equal in the rear view mirror, you look at like the Tradesk versus Olo and you go, the Tradesk is like, it's this infinite TAM, right? You could literally be Google, Facebook and Tradesk. And then you look at Olo and you go, okay, vertical SaaS restaurants, is that TAM limited? Probably all things being equal, but there you go.

0
💬 0

4620.47 - 4623.192 Harry Stebbings

Totally, but both made you a lot of money.

0
💬 0

4623.372 - 4629.038 David Frankel

Yeah. You know, Noah raised $600 million for 10% dilution when he IPO'd. That's fine.

0
💬 0

4629.398 - 4639.089 Harry Stebbings

He's a really good dude. Listen, I want to do a quick fire with you. So I say a short statement, you give me your immediate thoughts. Does that sound okay? Amazing. What have you changed your mind on most in the last 12 months?

0
💬 0

4639.571 - 4661.666 David Frankel

I used to think that PE firms were like the enemy of the seed stage. And I've changed my mind on that. We've got some PE firms in two vertical SaaS companies that I'm involved in. Their rigor, their financial discipline, and the help they've given to those companies has been great for the entire cap table. So PE can be very, very valuable in portfolio companies.

0
💬 0

4661.826 - 4668.67 Harry Stebbings

Mark Suster said on the show that liquidity will be provided by PE in the next generation as the core. Agree?

0
💬 0

4668.911 - 4669.491 David Frankel

Totally seeing that.

0
💬 0

4669.753 - 4672.291 Harry Stebbings

What investor would you most like to swap portfolios with?

0
💬 0

4673.55 - 4695.565 David Frankel

I find this easier to answer at the company level. So if I think of like applied AI, and I think of some of those companies, Micah Rosenblum on Vokada comes to mind. That is applied AI to camera. Josh Wolfe, who did Anduril out of Lux, that's like applied to drones. Again, if I look at Josh Kushner, billion on a hundred billion, I wouldn't bet against that. So my answer is company-based.

0
💬 0

4695.825 - 4720.002 David Frankel

Best board member you sit on a board with, and why them? Jake Saper from Emergence on Regal. has been just an incredible augmentation, just been a fantastic partner to have on the company. So Jake sourced Zoom for emergence, deserves a lot of that credit, reversed the track on this portfolio company and every bit of hiring, every bit of advice, it's literally like he can't do enough for a company.

0
💬 0

4720.463 - 4728.288 David Frankel

At a later stage, he chooses very carefully, he doesn't do that much. And when he does, like through thick and thin, this guy just gets involved.

0
💬 0

4728.728 - 4736.153 Harry Stebbings

What's the best investment advice you've received? Patience. Just be patient. What do you know now that you wish you'd known when you started Founder Collective?

0
💬 0

4736.574 - 4747.02 David Frankel

It's a long, long journey. And even post IPO, hang on. When you think your company has a real moat and is very difficult to compete with, don't sell too soon.

0
💬 0

4747.321 - 4749.322 Harry Stebbings

What was your biggest loss and what did you learn from it?

0
💬 0

4749.71 - 4775.034 David Frankel

Our biggest loss was probably Pinterest. There'd been so many. So what is my biggest loss? I met Marty Ardlin, who was starting Running Tide. He was a mechanical engineer, first individual in his family who'd gone to college. and just one of the most thoughtful guys in applied ocean that I've ever come across. Third generation lobster fisherman. And I was just very, very seduced by this.

0
💬 0

4775.114 - 4788.185 David Frankel

I reversed the truck for Marty. And what I think I underestimated is translating a product vision into something that was truly commercial didn't happen. We lost all of our money on Running Tide.

0
💬 0

4788.546 - 4789.867 Harry Stebbings

Biggest sin of the Zup era.

0
💬 0

4790.367 - 4796.131 David Frankel

Just too much money. Drove everything. Too much capital. Stuffing capital down entrepreneurs' throats.

0
💬 0

4796.611 - 4807.217 Harry Stebbings

But ultimate one, I had this the other day and I thought it was incredible. The heaviest thing in life is not iron or gold, it's unmade decisions. What unmade decision weighs you most?

0
💬 0

4807.898 - 4811.92 David Frankel

Oh, love that. That's such a good question.

0
💬 0

4811.98 - 4816.163 Harry Stebbings

It is. It's a really unfair one to throw on you, but I really think about that a lot.

0
💬 0

4816.624 - 4821.53 David Frankel

Oh, my God. I'm going to really have to give thought to that. Unmade decision. I literally have got to think about that.

0
💬 0

4821.85 - 4822.771 Harry Stebbings

It's a good question.

0
💬 0

4822.852 - 4823.953 David Frankel

Yeah, it's a great question.

0
💬 0

4823.993 - 4827.277 Harry Stebbings

Honestly, we just want to take away and think about it. I really thought about it.

0
💬 0

4827.297 - 4828.058 David Frankel

It's a great question.

0
💬 0

4828.198 - 4828.378 Harry Stebbings

Yeah.

0
💬 0

4828.699 - 4853.42 David Frankel

The unmade decision. Honestly, I look back and I go, every great decision was never binary. It was always weighing up scales. And I think getting to conviction is confusing for people because they listen to this and they go, oh, you're binary about that. Like you knew unequivocally. And the truth was like the biggest decisions, it was 51%. So leave South Africa and go back to live in Boston.

0
💬 0

4853.74 - 4873.065 David Frankel

take up the offer to start Founder Collective with Eric. Was that binary no-brainer? Well, the seduction of wanting to be in business with Eric definitely was. But everything I was leaving at home, burning bridges and burning the boats, it's insanely difficult. And I think that the older you get, the tougher it is to take binary decisions.

0
💬 0

4873.485 - 4894.606 David Frankel

And I think that the good part of that for a founder is when we give a term sheet, when I say, I want to be on your board, man, it is hard thought through. I do not do that flippantly. And when I do do it, like, do I have every single question answered? No. It's sometimes emotion versus intellect. And at some point you've got to go, I'm going to run with the emotion here.

0
💬 0

4895.428 - 4911.016 David Frankel

And conversely, if you don't have that, like, I think about this as going up the mountain. Instantly, we have this incredible rapport. Like I just leave that meeting feeling like so energized. And then I go home and I sleep the night, I wake up the next morning, I go like, this will kill you, this will kill you, this will kill you. You'll never take them on, right?

0
💬 0

4919.799 - 4920.18 Harry Stebbings

Oh, man.

0
💬 0

4920.44 - 4927.95 David Frankel

But like Harry's amazing, right? Like he's unbelievable. And at some point to ignore the emotional visceral response is also wrong.

0
💬 0

4928.271 - 4934.044 Harry Stebbings

David, listen, I want to finish with what question are you never asked that you should be asked more? What matters most?

0
💬 0

4934.404 - 4938.466 David Frankel

I come back to love and friendship and loyalty matters most.

0
💬 0

4938.887 - 4947.932 Harry Stebbings

You know, I started this show to meet incredible ambassadors. I've got a good book. You've got a good book? I've got a good book for you. Oh, gosh. You've got to talk about that. What's the favorite book?

0
💬 0

4948.012 - 4968.09 David Frankel

I'm reading this at the moment. I mean, like, I'm obsessed. Okay. What's the favorite book? So, Harry, I'm reading The Path Between the Seas by David McCulloch. The book was written in 1974. It won the National Book Prize in the US. And it had been recommended to me so many times. It is about the building of the Panama Canal between 1870 and 1914.

0
💬 0

4968.431 - 4982.466 David Frankel

Just to give you a sense of this, France spent $250 million and effectively went bankrupt. 20,000 people died, mainly from yellow fever and malaria. The Republic of Panama was like America doing the most colonial thing you could ever imagine.

0
💬 0

4982.486 - 5003.567 David Frankel

They basically took it and they paid, they gave the Republic of Panama, which they effectively created $10 million, and they bought the defunct business of the canal from the French for $40 million. That was bigger than the aggregate amount that they paid for Cuba, Louisiana, and Alaska. This was like big, hairy, audacious on steroids.

0
💬 0

5003.748 - 5025.086 David Frankel

And a friend of mine recommended and said, you know, if you want to look at like moonshot stuff again, and everything that was true in capitalism then is still the same. The lobbying, the politicians on the take, the media. The banks, you know, it puts like Elon, like SpaceX and Tesla just puts that in like insane. But this was like the moonshot of moonshots.

0
💬 0

5025.187 - 5028.129 David Frankel

And a lot of the time, like you look at Frederick de Lesseps.

0
💬 0

5028.209 - 5032.992 Harry Stebbings

But your fund size is not sized. But we can get these things started. To fund moonshots.

0
💬 0

5033.192 - 5036.115 David Frankel

But we can start these things. We can get involved at the beginning of these things.

0
💬 0

5036.155 - 5038.396 Harry Stebbings

Can you? They're raising 20 to start. Yeah.

0
💬 0

5038.576 - 5044.321 David Frankel

I mean, I have to like strong arm my partners into like putting $5 million into a company. But yeah, we can. Yeah.

0
💬 0

5046.926 - 5067.049 Harry Stebbings

Get that, Michael and Eric. Listen, David, I've loved this. Thank you so much. This has been so much fun. That was such a special one for me to do. David has been a supporter and friend for many years, and so it meant the world to me that we got to do that in person today. If you'd like to watch the full episode, you can find it on YouTube by searching for 20VC. That's 20VC.

0
💬 0

5067.309 - 5087.577 Harry Stebbings

But before we leave you today, this episode is presented by Brex, the financial stack founders can bank on. Brex knows that nearly 40% of startups fail because they run out of cash, so they built a banking experience that takes every dollar further. It's a stark difference from traditional banking options that leave your cash sitting idle while chipping away at it with fees.

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ensuring it not only reflects your unique style, but also ranks well on search engines. Plus, their flexible payment options cater to every customer's needs, making transactions smooth and hassle-free. And the Squarespace AI? It's a content wizard helping you whip up text that truly resonates with your brand voice. So if you're ready to get started, head to squarespace.com for a free trial.

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5166.634 - 5189.025 Harry Stebbings

And when you're ready to launch, go to squarespace.com slash 20VC to save 10% off your first purchase of a website or domain. And finally, before we dive into the show, I want to recommend a book, The Road to Reinvention, a New York Times bestseller on mastering change. No time to read? Listen to 20VC now, then download the Blinkist app to fit key reads into your schedule.

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5189.225 - 5207.595 Harry Stebbings

With Blinkist, you can grasp the core ideas of over 7,500 nonfiction books and podcasts. in just 15 minutes, covering psychology, marketing, business, and more. It's no surprise eight Blinkist users see themselves as self-optimizers, and 65% say it's essential for business and career growth.

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5207.875 - 5231.732 Harry Stebbings

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5232.092 - 5239.518 Harry Stebbings

As always, I so appreciate your support and stay tuned for an incredible episode coming on Wednesday with Zach Paré, co-founder and CEO at Plaid.

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