# The AI Boom Will Create Enormous Roadkill: Who Wins & Loses

Why Founders Should Never Take Multi-Stage Money at Seed · Why Triple, Triple, Double, Double is Good Enough

20VC · Aug 8, 2026 · 84 min · 15,731 words
Speakers: David Frankel, Harry Stebbings
Source: https://www.996.fm/episodes/20vc--ep-bcdeff5b/

## Cold open

**David Frankel** [0:00]:

The bubbles get bigger. This is the wave of our lives. Will there be roadkill from this wave? Oh my god. There's gonna be a lot. Well, the problem is the mega platforms are taking call options. Pro rata is almost like the original sin. I have never seen secondary markets as liquid. Are we headed for another .com crash? Definitely. If is not a question. When? Nobody knows.

**Harry Stebbings** [0:24]:

This is 20 VC

## Intro

**Harry Stebbings** [0:25]:

with me, Harry Stebbings. Now I do the show because I wanna learn from the best investors in the world. David Frankel is one of the best from Founder Collective. Why? Well, when everyone else scales funds, gets bigger and bigger, and bluntly loses discipline, lose the core craftsman like attributes of venture investing, David has stuck true to what he does best, early stage boutique investing. But you know what? It takes a great investors to do really well in one cycle. Yep. He's in Coupang. He's in Uber. He's in PillPack and SeatGeek and Olo and many great names. It's incredibly hard to move to a second wave. The wave of AI, the dude is in the seeds for Shield AI, for Suno, which is now worth $5,000,000,000. He has moved so seamlessly from a pre to a post AI world in a way that very few seed investors have been able to. This was an incredible discussion with one of the true craftsman of seed investing today. But before we dive into the show today,

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## Conversation

**Harry Stebbings** [3:28]:

David, last night, you sent me a forwarded email, and it was my first ever email to you. Eleven years. Eleven years. I can't believe that. Do you know what I found so funny is I just had dinner last night with Mamoon, and I look at the people who've been kindest to me, which is you, Mahmoon, Josh Cursor, Neil Mehta, and it's just fascinating that the people who were there when there was nothing are also the greats. And it's like maybe that's what made them great, that they give time to people where they just believe with no reason to. Does that make sense?

**David Frankel** [4:00]:

I'm honored to be included in that list. But maybe some of the thing is they're intoxicated, and you are intoxicating, in my view. Like, there's you you were 19 years old, but you were full on focus, energy. You just brought it, right? And I think maybe part of the job and part of the fun of the job is just recognizing that. It's not all it takes, but you had it. You have it.

**Harry Stebbings** [4:24]:

That is super kind of you to say. In terms of, like, having it, obviously, we both play at the early stages. And I've said before on social media and on x that the hardest part of the market is seed in many ways, and the worst performing funds will be the 50 to $100,000,000 funds. I say this to explain because you're too big to be collaborative to write those 100 to 250 k checks and be a friend, but you're too small to lead a 8 to $10,000,000 seed round. Why am I wrong, and why will this vintage be great for those funds? Okay.

**David Frankel** [5:02]:

There is so much to unpack here. You've got this narrowing out in venture where the bigger you get, almost like it becomes like a pyramid. I think there is the business of venture, which is asset management and this channel, right? So you've got the Cambridge Associates and you've got the fund of funds, and all they're doing is selling access. And they're fine with it. And if the you name it top 10, top five names are not in x, y, z great, great company. And I would say at this point, if you're not in the top five, you miss at a certain level, if you miss the 3,000,000,000,000 companies, you're much harder to sell. So it's not trillion dollar robust, but if you look at the numbers over the last twenty five years of how many companies were created that are over $100,000,000,000 there were less than 100 companies over the last twenty five years, less than 100 that are sustainably over $10,000,000,000 companies. So at that top end, you've got to be in that. The median company, and we've done a lot of work on this very recently, of the top 500 companies created in the last twenty five years, the median is 2,600,000,000. Now, if you own 5% of one of those companies, you return the fund each time. And I would say what's gone on in seed is there are a whole bunch of unreasonable bets being taken with loads of funds and loads of money, and it's quick because you've got to get the check-in because you've got to get to the next fund. So it's incredibly tough at seed. What makes this still a great business is it's a little bit of what I said about you is you can wait and wait and wait and wait if you're patient, and then you just see someone, right? You see a founder or you see a team and you just go, I have to be there. And to me, that's code for this may just be another Uber, another Suno, another Shield AI. And I think a little bit, I'm answering this personally, a little bit of this is a drug. Finding Harry, right? Finding that is a bit of a drug, so I, you know, addicted if that's the case. And I think that that, if you're in early, you still have a chance of returning a fund. I think it's totally different business. Do you have to be the full 8,000,000? Definitely not. We can't be. Can you write a 3,000,000 check? Can you write a $500,000 check? Now, valuations, uncapped notes, that's changing the business. But you don't just have to do that. So if you're on piste, and I would say if you're on piste for the last I've been doing this for eighteen years, nearly, is it was always expensive. It was always tough. But you find some of the best people off

**Harry Stebbings** [7:40]:

pieced. Always. On those rounds, when you look at the eight to 10,000,000 rounds or the the large seeds that we see today, are you able to participate, though, with the two to 3,000,000 when you have your the multistage products provide such an efficient seed product that actually you might get a 100 k, but being a 3,000,000 check is much harder. Are you able to even do that strategy?

**David Frankel** [8:02]:

You know, I hesitate to say this, Harry, but I think we're being seen, and I could be over extrapolating the last 20 deals that we've been involved in, almost as an insurance policy, where we're side by side. We're putting in 500 ks or a million. There's been $89,000,000 going in. And from smart entrepreneurs, there's almost this knowledge of they may abandon me and then having FC in my back pocket could be useful. Sure. And I'll use their brand. I'll use their distribution network to go out and say, They actually don't suck. We're not doing 10,000,000 ARR yet, but they're more patient, and be patient, and we're the testimonial salesperson. So I think there's some recognition of, wow, for $500 or $1,000,000 not bad insurance policy. By the way, we're not doing that many $8,000,000 rounds. We're still finding $3,000,000 $4,000,000 rounds. Are you? Yeah. The valuations there move a lot, right? They change a lot. By the way, the other thing is there's very little evidence yet that these hot, hot AI companies that are raising huge amounts of money are capital efficient. Like, the jury's out on whether that's gonna work still. Totally

**Harry Stebbings** [9:15]:

get you. Just before we move away, you said it's not in the hot, hot, hot. You often don't get paid for being a value investor, and you can sometimes be criticized for being smarter than the market or whatever contrarian you wanna say. My question is, we do think about, is this an asset that will get financed in future funding rounds? And if it's not in AI and it's a traditional enterprise HR company, dude, I can't get that funded for a good A. Does that impede your thinking on whether you'll do the seed? Well,

**David Frankel** [9:43]:

everybody's AI. It's almost like saying that you're not AI today is like I'm not using the Internet. It's like, Why wouldn't you use the most contemporary tools? So everyone's AI. You've just got different approaches where you've got a second time entrepreneur that goes, I know this domain really well. I've been doing SAP consulting for ten years or twenty years, SAP, and I've built a platform, but this part still sucks. And I was playing around with Claude Code. This is a real situation. I was playing around with Claude Code. My CTO is unbelievable. We're now putting four or five together. Would you be involved? And it's a 20,000,000 cap. Sure. Right? We lots of that. So the concept of it's only a 20 something, I'm not saying we don't do that. I mean, you know very well we do that all day long. But we also see other startups in places that feel off piste, and then you look at it and it's worth tens of

**Harry Stebbings** [10:39]:

billions of dollars this time. The statement that is said to me more than ever is price matters less than ever because the only thing that matters is that you're in the true winners of the day. How do you feel when you hear that?

**David Frankel** [10:49]:

I mean, the scale of how much you have to win, right, is different based on your price. It's pure math. So uncapped notes suck at the seed stage. I'm not saying we've never written one. Unfortunately, I've written one. And I think the founders are exceptional. I think they'll do great. Do you regret it? I don't regret it at all because I love the relationship. But financially, will we do as well there? That's gonna be $100 to $300,000,000 price when it happens. Now, you're in a year in advance and you take that price. From a venture perspective, it doesn't make much sense. And access is being sold. The IVs, Stanford's done this forever, but MIT and Harvard doing the same thing. It's like, you just wanna be there, right? Sometimes you really have to think that through, and we've said no plenty there. By way, we'll probably regret the ones that we said no to.

**Harry Stebbings** [11:40]:

We see YC really professionalized startup founding in a way that it turns it into almost a norm for people leaving some colleges in particular and some programs at certain colleges in particular. Do you worry about how almost easy it is to be a startup founder today in terms of that normalization of it, and what that means for what we do? I do.

**David Frankel** [12:02]:

Yeah. I think there are so many founders, right? It's like de jure. I think there are fewer entrepreneurs. And when the tide goes out, everybody goes, I knew, I told you so, and nobody knows when the tide goes out. But what it takes to be an entrepreneur is just very different in terms of fortitude, in terms of the ability to energize, the ability to go up that learning curve. The number of times I've seen the difference in the trajectory between the CEO and the CTO. The CTO, at some point, up to 50 people, you're golden. And then at some point you go, actually we could bring in better, better technical skills. And if you've got a good co founding CTO, that person becomes like a Swiss army knife and is deployed in different ways. The CEO goes on this serious journey where the learning curve is steep and they've got to learn to manage, and they've got to learn to put bums on seats. And I think of people like TJ at PillPack or Jack at SeatGeek, and they've changed individuals. I had coffee a week ago. We had an hour, Mikey Schulman from Suno. And I said, What are you doing? And he said, I'm 40% of my time. I'm just recruiting. I had lunch years ago, decades ago, with Jeff Bezos. I was invited to a lunch, and someone smarter than me said, what do you spend your time doing? And he said, 50% of my time is bums on seats. That's never left me. That's the CEO journey. That's the entrepreneur's journey. And there are many founders that don't cut that.

**Harry Stebbings** [13:34]:

I think one of the biggest mistakes that I see investors make, though, is when they turn down a company because they don't like the other cofounder. And the truth is, the other cofounder's most often not there in three years. You don't like them because you don't think they're good enough and not as good as the CEO. Will you invest if you think the CEO's amazing, but you don't think the CTO's up to scratch? Or the head of sales who's also the cofounder isn't as good. What are your lessons on that? Rarely.

**David Frankel** [14:01]:

We do that less. And I think your logic is correct. But so early on, we're looking for this package. I'm looking for this CEO, CTO kind of magic. And in some ways, I literally use that word, like I'm looking for the CTO to be a bit of a magician and the CEO to be a good salesperson. That's like my favorite combo. And I agree with you. The CEO being a good salesperson and being a real entrepreneur is actually more important because the CTO role can be fungible, depending on how complicated it is. But I have said no more times than yes in those situations. And I regret some of them. But the dynamic between those founders matters. Early on, like to me, I look at the dynamic. And in some ways, I think I want to replicate the partnerships that I've loved and go, I'm looking for some kind of alchemy here. You don't have to be identical. You don't have to finish each other's sentences. In fact, I prefer that you were different. But how aligned are you and how much you trust each other's kind of competence and go. And in a career, I've seen alchemy maybe one hand, like five times, four or five times. But when that alchemy happens, it's because of that interplay between those two people. So I'm watching that pretty carefully.

**Harry Stebbings** [15:20]:

Has the type of founder that you like changed, especially in the last few years? I think our team has definitely oriented much more towards, like, deeply engineering specific people who come out of DeepMind, who come out of Gem and Iowa. Has that changed? Less than you'd think.

**Unknown** [15:35]:

So

**David Frankel** [15:36]:

I would say the youth, the energy, the focus, the smarts, you put that package together, and it's an intoxicating package. Mhmm. I look at experience, and I go, What are we gonna need to package with that experience? There are certain situations, SaaS and enterprise SaaS certainly looked like that, where you'd learned the lessons. You understood the market. You understood who the buyers were, although that's very fluid, too. But did you have the focus and the energy? And I see these 20, by the way, it's a psychographic in a way, so I'm not saying that I don't want to sound ageist. The psychographic of that focus and intensity can last for decades. But there's something about it at that early stage that is just, wow, I want to be part of that. And that still turns me on a lot. Now the theory of, you know, the relationship, etcetera, go one more time is it's great in theory. But, man, you need to go this journey, you need so much energy.

**Harry Stebbings** [16:37]:

When we look at the scaling journey, we said about kind of how founders have changed that in terms of what we look for or not change for you. One thing for me that's changed, and I I get in so much trouble for this, and, like, VC Brags, his Twitter account killed me for it the other day. I very candidly said, I turned down a company the other day that went from one and a half, and they were gonna go to five. And then they were gonna go from five to 15, and it's just not enough anymore. It's it's just not interesting. I'm sorry for venture. We have an opportunity cost of capital where we can deploy, and that's not fast enough. Has triple triple double double gone? Is that still a venture path in today's landscape? 1.5 to 5,000,000,000? 1.5 to 5,000,000 in ARR. And so you're looking at this company going, okay. You're gonna be one and a half to five, five to fifteen, fifteen to 30. David, four, five years down, we might be at 70. Is that still a venture pathway? You know, these

**David Frankel** [17:34]:

ten year funds are taking eighteen years. The one thing you learn is loads of patience. It's such an opportunity when people go, It has to be one and a half to 10 to 15, and then reality sets in. And sometimes it's twice as expensive, and it takes twice as long. Harry, we still own every last share in SeatGeek. That was an investment I made in 2010. It's in the top three ticketing businesses in the world. It just takes a really, really long time. Some of our greatest companies, they were showing tremendous promise. But that 1.5 to 10 to 20, I just think, are they executing? And the other side is, is revenue the only metric? Sometimes there is traction on dimensions that the market is not necessarily recognizing, but you're an insider. So that account, the retention in that account is really good, and that one account is now spending 4x what they spent a year ago. And there are more DAUs. There's got to be traction. And frankly, a lot of what we do to try to tell an entrepreneurial story to get more funding is the different dimensions of traction. But I think this go, go, go overnight or you're bust, I think there's a lot of orphans out there for that. And sometimes, frankly, I look at those funding rounds and they're called seed plus or seed extensions, and I go, that may be the opportune moment. Like when they're being abandoned and they can't get the capital because the bigger funds have moved on, maybe that's the opportunity. It's not what we really do, but I can see it as a capital markets opportunity. Do you remember bullpen? Where it was like their business to do exactly those rounds. Was an interesting business. I don't know how they've done, but they priced those rounds.

**Harry Stebbings** [19:15]:

They they priced them for bigger bigger players. I think the thing is you're so paid for the risk that you're taking there. I mean, they really were aggressive in terms of ownership that you need I think they did Ipsy, which was a big business. Yeah. And so you have one, and it pays for the rest. Can I ask when you look at this, David, you've been doing this for eighteen years, and you hear people like me say, oh, one to five, like triple triple double double is dead? Is it really a home run if it's, you know, we need a billion dollars in revenue, Jason Lemkin says on our show. Billion valuation? Come on. That's not venture anymore. Is this, like, peak bubble when you review the eighteen year journey that you've had?

**David Frankel** [19:51]:

The historical or anachronistic view on this would be the bubbles get bigger. This is the wave of our lives. I feel that way, by the way. If I look at Internet, SaaS, mobile, AI, nothing looks the same. And will there be roadkill from this wave? Oh my god, there's gonna be a lot. You know, again, you look at those stats of 500 companies, less than 100 over 10,000,000,000 in the last twenty five years. How many times, Harry, over the last eleven years have you heard, This is different? This is different. It doesn't mean that there aren't survivors and companies that are gonna change the trajectory of technology forever. And I think in OpenAI and Anthropic and SpaceX, we're seeing that already. Like these are the metas and the googles of our era, highly likely. But wow, like it's Hollywood, man. Like 95% are not gonna be there. And it goes back to why is seed interesting? I don't have to be in the one. If there were five companies that are worth $5,000,000,000,000 with exits so if you look at SpaceX, Tesla, Meta, that's trillions of dollars already. You take then Nvidia. I think Nvidia started pre-twenty five years ago. But even if you look at the last twenty five years ago, you can add Palantir to that, Palo Alto Networks. That's about $5,000,000,000,000 of market cap. And then the other four ninety five at a 2,600,000,000 average. And some of those are, we hope everything looks like Shield AI, Suno. But if you have 5% of a $2,600,000,000 outcome, you've returned your fund. If you have a $500,000,000 outcome, it's incredible still. And that's why I think seed isn't dead. I think seed is crowded, to some degree, very commoditized. I feel commoditized. I've said this many times. I feel like brand and, in some regard, distribution, as in your portfolio and people saying nice things about you, get you to the table.

**Harry Stebbings** [21:46]:

But if it's commoditized, does price not just become the separator? And if price is a separator, the mega platforms win.

**David Frankel** [21:53]:

Well, the problem is the mega platforms are taking call options. Is this good for the mega platforms? Is this good for the LPs? Or is this good for the entrepreneurs? Well, probably for 95% of the entrepreneurs, it's not good.

**Harry Stebbings** [22:03]:

Why? You get more I agree with you, but I'm just playing devil's advocate. You get more money at a higher price with mostly a more junior VC who will let you do your work and not get in the way. Isn't that what all entrepreneurs want? I mean,

**David Frankel** [22:17]:

sounds amazing, Yeah. More junior entrepreneur moves on, right? You're all fund. More junior venture invest, you mean? Yeah. Yeah, sorry. And the more junior, the principal at that big fund moves on. They start their own fund. They move to another fund. Happens all the time. So the person who invested doesn't have mandate. They can't sit around with the partnership and say, Look, let's just put in another five to 10. Let's turn over another card. Because your champion's gone. By the way, I'm being contrarian here. This does not always happen this way. I'm just giving you the other side to this. And then you haven't made the kind of one, five, ten, fifteen ARR, whatever you want to call it. You just haven't made that. So it's like you're overlooked because it's like let's focus on our real winners and that thing's worth 2,000,000,000 or $3,000,000,000 So 95% is mandate for further funding is dead, is gone. Now, this is the beautiful thing about most entrepreneurs is they just don't think about themselves in that category. I'm the 5%. I'm the 2%. And that's why we love entrepreneurs. But the stats are so far against you. It goes back to I hate to think of ourselves as their insurance policy, but I think a few entrepreneurs have thought about that. And I think there's a little bit out in the zeitgeist going, FC is a great insurance policy. You want them in the round. And it costs very little to have Harry or David in, like, for 500

**Harry Stebbings** [23:35]:

k or a million. Are you really not tempted to raise more? Every single constrained fund, including benchmark, historically, central figure and discipline in venture, has raised a billion and 0.5 growth fund. I was with another great growth fund that is very disciplined as well, but we're raising billions too. Everyone who was is like, no. We realize the game on the field is you need money. Are he really not raising more? It

**David Frankel** [23:59]:

would be disingenuous to say to you that we don't have the discussion, that it isn't attention, that we go back to it. It's hard to be contrarian. When there's so much money going around, it's hard to say no. And then here's how we come out, is the GP has been the biggest LP, and we're greedy for returns, not management fees. What percent of the fund are you now? We're certainly, in the last few funds, the largest LP. There's no LP that is bigger than the GP. We're seriously aligned with our LPs, but what are we seeking? And this is the answer to your question. It may be wrong. Literally, if you do the analysis, you may go, That was crazy. You left so much on the table. We've been very disciplined about strategy and very disciplined about DPI.

**Harry Stebbings** [24:46]:

But if I just look at you I'm sorry. I'm playing devil's advocate again. I'm just like, like, you know, you had Coupang. You had Uber. You had Trade Desk. You've got Shield. You've got Suno. Tack on another 3 to $500,000,000 vehicle and keep going. I'm sure you knew Mikey was amazing. I'm sure you knew TJ was great. I'm sure you knew that these were great on. Surely, that is a conversation that has rationality.

**David Frankel** [25:11]:

Because it's

**Harry Stebbings** [25:11]:

a

**David Frankel** [25:11]:

rational conversation, it comes up. And then you come back to saying, Okay, who wants to do this? You're an off-site with a partnership and says, Who wants to do this? And I go, Oh my, I love the early stage. I kind of may do it. And by the way, I am an opportunist as well. I think of myself as some kind of value investor. So the interesting times for that for me have been when nobody's funding. Why? And I think that person's great. Or it's a consumer play. And I know consumer multiples are lower, but this is an Internet acquisition device. And these founders are better at acquisition. So it's not in the hype hype hype go go go. I'm kind of immune to that.

**Harry Stebbings** [25:56]:

I'm in pain. I love you so much because you're so much smarter than me, but I'm just like, the market can stay irrational longer than you can stay solvent. And when I look at, like, a Wix today trading at 2,100,000,000 on 2,100,000,000 of revenue, it's a great example where, like, there's obviously rationality at play, but it doesn't matter. The market's the market. And if consumers, say, is getting the pricing that it's getting, I can't change that no matter how good the acquisition machine is. And so, like, don't fight the tide that's against you is my thesis or ethos. I can swim in the swim lane that's swimming in your favor. Am I wrong and I'm just missing a contrarian beat? No. There are so many ways

**David Frankel** [26:39]:

to do this, and people have done so well. There are big funds that have returned very well. You've got to be in the right vintage. But if you look at Thrive or A16z, they've had some big funds that have returned very, very well. A little less since 2020. If you look at the DPI analysis, the jury's out from 2020 onwards. Now, course, if you're like Josh and you're in SpaceX and OpenAI, that's gonna be the most ridiculous fund. But wow, you are in the most rare air. And then there's just something that's competitive and unique and it is economically irrational potentially. But it is, I was in that company. I was first, I wrote the biggest check. Somehow for me, being competitive with me, that is the biggest thrill. I was with that founder from the beginning and we literally reversed the track and gave them everything they wanted. And by the way, does that mean that we're not writing three dollars four million dollars checks now? We are, right? Because if you want to get a percentage ownership in something that you think is extraordinary, you're writing much bigger checks than we wrote before. So the fund is going faster than it used to.

**Harry Stebbings** [27:53]:

What is your average ownership now? Has it gone down over time? Because I look at ours, and our biggest mistake, and I can look at Deal, Eleven Labs, I can look at Granola, I can and Star Cloud, Fractile, could have done them all, but would have had one to 2%. And all of them we turned down purely for ownership. That is hundreds and hundreds of millions of lost returns for ownership. I've never thought about that.

**David Frankel** [28:19]:

Bugger. I I I mean, all things being equal, I'm a capitalist, right, so all things being equal, I'd love to own more upfront than less. But it wouldn't be the reason you turned it down. I've never. I've never turned it down. Never. And Mikey, I wanted to give him every last cent. He reached a point where he said, Look, that is the dilution I'm willing to take. I'm not willing to take another iota of dilution. We gave him what we gave him, which was literally every single cent in his first round. We showed it to other people, by the way. I showed it to you. Thanks, David. No doubt. We weren't gonna bring it up. And then when Matrix led, which was not it wasn't a popular round. Lots of people said no in that round. We asked every last cent. But would I have said no to Mikey because of percentage ownership? When you meet the right people and you're all in, you get what you get.

**Harry Stebbings** [29:11]:

And so you will do the 1% to 2%, and you'll take it, even though you can't size up in next rounds.

**David Frankel** [29:17]:

Well, you know, again, I think pro rata is almost like the original sin. But if others have it, I don't think that we should be excluded if others have that pro rata. We are seeing rounds now where there isn't pro rata for anyone but the lead, but the most major share. So it's not a pro rata for all major shareholders. It's for the lead shareholder. I'm not sure I agree with that either in this environment. I kind of think that there should be a universal approach to treat your investors equally. But I think pro rata is generally not great for entrepreneurs. It's a call option against you. We feel like we've had to work every time to put in a bit more money. We've never ever led another round. So we have this view of it would be negative correlation bias. It would be unfair to everybody if we didn't be somewhat kind of uniform. Do you think it's harder than

**Harry Stebbings** [30:05]:

ever to accurately concentrate dollars effectively given the rise of such preemptive rounds. We've had them where we haven't even wired the money, and there's a new term sheet. At different valuations? Yeah. And that happens quite often now. Is it harder than ever to concentrate effectively when it's just so fast?

**David Frankel** [30:25]:

Some kind of framework is really, really necessary. And I credit my partners over the years with that of saying, We may be writing bigger checks, but above that post money valuation, it's really not our opportunity anymore. And you can look in the rearview mirror and say, Man, I should have done Uber. I should have done Shield. I should have huge kudos and power to the people who did. But a framework lets you act very quickly. And I would say credit to Eric Paley in this case is he always created some kind of discipline. So the post money went up and up and up as rounds and the momentum and the size of money and the environment changed. But we would never lead another round. We've never done that in our entire history. So we haven't been preemptive, and we haven't been like, we'll lead your Series A, and we like you more than others. But our ability to participate has always been there. Peter

**Harry Stebbings** [31:20]:

Thiel said before, if he'd just done every round that anyone else had done at an up round and it was a good brand, he would have done much better. Have you found that to be true? Given the

**David Frankel** [31:30]:

era, like, this has been the golden golden era, it's probably from a data driven approach, it's probably true. Like, if we'd followed on in Uber, Coupang, Shield, you name it, Suno. If we just followed on, probably the data would show that we've done pretty well. Our view would be we would have had to have followed on in everything, and I think that the absolute return would be better. I don't think that the multiple would necessarily be

**Harry Stebbings** [31:56]:

better on the fund. I'm not being rude. A framework is not the enemy of this venture cycle. Like, I think it's so easy to be rigid in your mentality around, oh, we won't do anything over a billion, but I and you're gonna absolutely wince at me here. So are you ready for a real shot? I think a billion dollar valuation is the new series a. And you're like, woah, Harry. Woah. Woah, kiddo. Calm down. Listen to the facts. We used to do a 50,000,000 post and hope it would become a billion, 20 x without dilution, like blunt. Now you enter at a billion and you hope it becomes 20. You know, we have McCor at 20. We have Cognition at 26. Cursor gets sold for 60. Sold. This is liquid. Well, maybe a billion's the new Series A. No?

**David Frankel** [32:35]:

I think you may be looking at the top two or 300 companies. Is that not our business? I don't think so. I think that that's the momentum business, and I think knowing how and when to get out quickly with some of those really, really matters. And that's not really my business. So my business is value, is getting involved early and trying to find value opportunities. There are times, again, where it's an intoxicating founder and being on that journey together. But I'm not sure that those are your fund returners. The difficulty with some of those momentum assets is it was what we were talking about earlier, is you've got to be able to run for the exits when you can. That's exactly what you were saying is you didn't think that founder was all that great. Or you thought that the valuation was so far ahead of the reality of the business. But you're asking a question. You're asking a momentum question. Yeah. And is it all momentum? I've got to be careful not to be too anachronistic in this because we have invested in momentum. There's just no it would be so disingenuous for me to say that we haven't. When you say that, what do you mean we have invested in momentum? Our knee jerk tends to be when this has gotten across a certain point, like we're out of here. And credit to Eric at a point for going, like, we've captured 80% of the value. We could capture another 20% if we did Uber at Series A or if we did Suno at Series A. And by the it's not just on paper. I think there would be buyers for that position. So in hindsight, I look at that and I go, Were you anachronistic? By way, we didn't even seek to participate in that round. We kind of go, we built our ownership position and we're done. This is not the kind of investors we are. We're looking for the next seed stage round. And I think, Harry, what we've done is we've drunk the Kool Aid to such a large extent now. You and I are so different that you're going, This is hot. Let me go, go, go. I'm going, I've got a smaller fund. Where else can I really x my ownership versus getting a 5x or 10x? But of course, the environment makes you look quite silly in retrospect. The question is, how long does this environment go on for? And it's

**Harry Stebbings** [34:42]:

also about, like, how and this is the you have unbelievable returns, and you've made a phenomenal amount of money for your investors, but the quantum of cash that you move matters. And Josh and Elad and the multistage funds moving hundreds of millions and billions, you make a larger quantum of cash. And so I get you with the in terms of your your multiple goes down when you lead the Series A. Look.

**David Frankel** [35:05]:

There's so many different ways to play this, and I think when you talk about Josh and, you know, a handful, they've killed it. They've absolutely killed it. A lot

**Harry Stebbings** [35:14]:

of LPs, very wrongly, I think, don't like the large platforms and always just come back to this very kind of, I think, basic rudimentary thought that as you scale fund size, returns always get worse. Always. Whenever someone says always be careful. But I think with the outcome expansion that we've seen, Cursor at 60,000,000,000 trillion dollar companies in a matter of years with OpenAI and Anthropic, you will see venture returns with mega platform sizes.

**David Frankel** [35:41]:

Do you agree? Largely, no. So largely, I would say, who are their LPs? Who are they working for? And in some of these cases, not even endowments anymore. It's sovereign wealth funds. And sovereign wealth funds and public investment corporations are looking for IRR. They're not measuring this in how many times do you x the fund. Doesn't mean that A16z and Thrive haven't x ed a few of their funds really, really nicely. Again, subsequent to 2020, the TVPI is there, and in some cases they're on steroids, the DPI is less there, if you look at the actual stats. But they're working for these sovereign wealth funds, they're giving great IRR. And some of the endowments, some of the biggest endowments are like rounding errors now. The question is who you're working for. And I, again, obsess with this alignment with the entrepreneur. We're working for ourselves as well. And we're working for DPI. And the bigger we make the fund, the tougher it is on the DPI. Like what am I doing this for? Fund after fund after fund. If we look back on fund two, it's all about applied AI. I mean that's really what the fund if you look at the winners in fund two, it's Shield AI, which, by the way, in 2016 was called Shield AI. It's Vocada. It's Whoop. Now, all of these things are commoditized. All of the hardware is commoditized. Video cameras are commoditized. Drones, I mean, you can buy a drone for, forget DJI, you can buy a drone for $20 now, right, dollars 50. It's about putting AI around these completely commoditized platforms. It was ten years ago, but it wasn't the theme. So the one thing that you're talking about is momentum around a theme. And I'm going, in ten years' time or in five years' time, there will be a new theme. The job will have been to get into that theme ahead. I don't even know what it is. I hope I've got some on goal. And those weren't the expensive ones. Those were not they never are. So using AI is really important. I guarantee you, all of these things are called applied AI businesses today or physical AI. Physical AI is all. The job is to be in there five years or ten years ahead, and it's not where the momentum is.

**Harry Stebbings** [37:50]:

It never is. When you look at you said that kind of fund too, and you said a couple of names there with Vocados and your Whoops and your Shields. How concentrated are the returns in your funds? I spent time with Honam from Altos, and he's spoken about the return concentration with roadblocks. Mind blowing to me. How concentrated are yours, and what lessons do you have from that? The amazing

**David Frankel** [38:11]:

thing is they've been way less concentrated than you would expect. Look at fund two. Forget fund one now. Fund two, Vocada, Shield, Whoop, PillPack. In and, for the most part, one of or the single largest investor in the first institutional round. It's not concentrated. If you look at fund one, we always talk about the Trade Desk and the Ubers and the Coupangs. Fund one still has Airtable in at the very beginning, challenges in the SaaS environment. But Simply, Simply is the biggest piano teaching and music instrument teaching company in the world, SeatGeek. Haven't sold a single share in SeatGeek. That's still in fund one. Why haven't you sold a share in SeatGeek? I think it's spiritual at this point.

**Harry Stebbings** [38:57]:

It's a religion. Beneath the shirt, you've got Jack's face, right? That would be an epic I did that.

**David Frankel** [39:03]:

I did that at my LP meeting. That would be very funny. Before Jack, Jack and Mikey both presented. And I literally said to them, get me T shirts. And I had ripped open my shirt.

**Harry Stebbings** [39:13]:

But I I'm actually worried about this, which is you know, and I'm not positioning this at Airtable at all. I think Howie's wonderful and brilliant and a brilliant product team. But, like, you're seeing the cannibalization of leaders in a space like Airtable respectfully and like SNEAK, the cybersecurity company, which in a similar vein is going through challenging times too in terms of growth rates and everything involved. Well, there hasn't been a liquidity event, but the cannibalization has already started. It's like the innovation cycle's taken steroids and gone too quickly to allow liquidity events to even happen. Does that worry you too? I mean, by

**David Frankel** [39:48]:

now, Harry, it's it's very hard to play around with Claude or something like it and not have the revelation that we've all had. But then you look at some of these SaaS companies and you look at the SaaSpocalypse. When we were on the Olo board, when it was listed, we'd look at companies like Veeva, which is I think at a $30,000,000,000 market cap now. It's come down at least 50% or more. And we'd go, this is the most perfect like, we want to be this company. It's hard not to look at some of that market cap erosion and go, is the baby being thrown out with the bathwater? And it's about the last 5%, I think. And I would say if your Airtable and Veeva or Olo look very different, the more embedded you are, the more difficult you are to dispense because real time thousands, billions of orders are being run-in your system or like, mission critical biotech research is being run-in your system, the more embedded you are, I think the more overdone that SaaSpocalypse may be. The less embedded, clearly, the easier you are to kind of turf out and play around with Claude, you name it. But I think we're underestimating that last 5%. The contrarian in me, this is not what I do, would say buy a basket of the top SaaS stocks that have all lost huge market cap. You're gonna do okay.

**Harry Stebbings** [41:05]:

You are. And Rory O'Driscoll, who we do the show with every week, has done that, and I put my money into Palantir and said I'm a momentum surfer. I did better. And that's the hard point, is the opportunity cost of cash is so real. Yeah. You can be in one and try and be smart, but you're probably right long term, or you can just be momentum trader, and you'll be right actually in the short term. And if you can time it well, it makes a difference. Yeah. The difference between,

**David Frankel** [41:29]:

in a way, between Al styles is every single company I invest in and it comes back to concentration, every company I invest in, I invest in with the hope that it could be another Suno or Uber. I literally do. I don't invest in companies and go, Oh, I'm investing in you, Harry, because I think you can be a 10x outcome. I don't do that. You don't? No. Wow. Every company we're investing in, we think, wow.

**Harry Stebbings** [41:52]:

This could be ginormous. Jason Lamkin just told me very simple. He said, I'm not smart enough to predict the future. What I look for is can I get a three x on my next funding round? And if I can get a three x on my next funding round and I really believe in a great entrepreneur CEO and a great CTO, I'm in. So we we use

**David Frankel** [42:09]:

the same logic, but it's always been 10 x. I will not invest in this if I don't think if I'm not sure that there's a 10 x. We have at our team meeting, I love it because If you can't complete that sentence, you can't invest. That's how we start the team meeting. That's how we start talking about a portfolio company. What's your greatest ever answer to that? So in more recent times, I've gone, I love it because I'm obsessed with Harry. Every question I ask, I get a better answer than I expected. Every time I press, there's no evasion of the facts. He never says to me, Oh, we're the only one in this business. He always says, It's so much harder than you think it's gonna be. It's so much tougher, and, like, this person's leaving me, and I love it because they're obsessive. They're all over it. They're so deep in this, and I just can't get this out of my I will not say I love it because of valuation. But we've always come to valuation last. We've always gone opportunity, market, founders, founders first and foremost. It's in our name. And we come to valuation last. And I cannot say that every single time we've invested, we've gone, This is a perfect valuation. In fact Rally is. No, it really is. The best deals, both sides feel uncomfortable, I find. Of course. Of course. Exactly right. By the way, you can go I love it because of insight into the vertical. I love it because of an edge that nobody else can match in a commoditized business. I'm writing this piece on Nepo Babies, and I'm going, I love to fund Nepo Babies. What? I'm writing this piece right now.

**Harry Stebbings** [43:41]:

Why do you love to fund Nepo So

**David Frankel** [43:44]:

T. J. Parker, working in his dad's pharmacy when he was 15, 14, 16, he has got more edge in that vertical than he knows. Mikey comes to voice AI, to music, to audio. They've come out of Kensho. That's all they did at Kensho. So you take Mikey and Georg and Martin Camacho. That's all they did. Martin was the CTO of Kensho. Now they're not the Nepo baby, but Evan at rebar. So Evan at Rebar is HVAC preparation and HVAC quoting. There are over 100,000 mechanical engineers in The US that are making 100 ks each at least when they graduate. And all they're doing is sitting with this blueprint process so that they can quote a new commercial. Evan's sitting there, and by the way, he did work for his uncle's company that was rolled up in a PE, 10 of these things, and they said, Go out and find the AI for this. And Evan goes out and goes, There's no AI for this. And he goes, I'm starting rebar. And I go, There are folks who have been in these verticals since they were kids. He watched his uncle in this vertical. It's like there was nothing else he was gonna do. I go, like, they have more edge, and they know what to do with.

**Harry Stebbings** [44:59]:

I get you. Sorry. Just to be clear for you, Netho Baby, where I'm from, is trust fund baby who has billions of dollars. Was like, dude, I do not wanna be funding the kid who's at Scorpios in Mykonos spraying dad's money. We're using

**David Frankel** [45:14]:

Neppo Babies with different definitions. Very different definitions. I'm talking about folks who've and been in the

**Harry Stebbings** [45:22]:

have lots of edge in that vertical. That I totally get. You said you haven't sold a share of SeatGeek. The timing of when you get out matters a lot. Do you have any lessons on when to get out, given I think this generation of seed managers will be defined by their ability to access and navigate secondary markets effectively?

**David Frankel** [45:40]:

So it's interesting. You're asking this at a time where I have never seen secondary markets as liquid. It's probably not that surprising given fewer IPOs, fewer M and A up till the moment here, an IPO market that will probably be open for the remainder of this year. And then these IPO markets always close. So in the top 100 names, wow, the secondary liquidity is incredible. And you can price your position, I would say, reasonably efficiently. You can look it around and go, Okay, the secondary markets offering me a 25% discount is probably worth 7.5, not 10. And then you can look at a number in the top 50 at least where you're being offered at least the price per share of the last round A 100%. Because loads of folks, loads of big folks, Blackstone, didn't get their pro rata, and then they're sucking it up. Most I'm seeing do not have a discount, for sure. Yeah. We've seen a premium where insiders know there's another round. Talking to your point about momentum, right, you were talking about momentum in the early stage, we've seen situations in our multi billion dollar names where the round goes down in December and the board's already talking about the March round. And we kind of see it sometimes when we're not on the board, but we just see it in the momentum in the secondary market. Now, Harry, you're in very rare air there. Let me just say I don't want to in any way make it sound like we're in that with all of our companies. We're in that with, at any one point, a handful of companies. But in those situations, I think the difference in fund management is when you take secondary and the ability to give DPI. Even in your top names, sometimes taking 20% off the table if you can return 25% of the fund, particularly if it's a newish fund. So if it's a twenty twenty four fund and you can give back 25%, why wouldn't you do that? And you're still long. You still own 80% of that company.

**Harry Stebbings** [47:39]:

I just think we don't think about the velocity of cash enough. And what I mean by that is, like, yes, there might be another double. But if I have to wait five years and then the IPO and then an eighteen month lockup, Jesus, give me 50% of that now, and I'll way rather have the certainty and the DPI now than the maybe a double from here with 6.5.

**David Frankel** [47:59]:

This is not a precise science. I have looked back in every direction, and we've gone by the way, the best is you sell 20% and you were wrong. Awesome. Did you do a good job of sell down on Uber? You know, in retrospect, we probably sold a little too early. This was early on. You know, this is a business that's getting close to $10,000,000,000 in valuation, and there's an opportunity to take some off the table, and you're very new.

**Harry Stebbings** [48:24]:

Also, at the time that I'm so sorry. It sounds awful, again, you chastised me. 10,000,000,000 at that time was so much more than it is today. Yeah. Did you sell it all at 10,000,000,000? No. Definitely

**David Frankel** [48:34]:

not.

**Harry Stebbings** [48:35]:

No. No. We were we were net long at the IPO. One thing that's very sad or challenging is when when an exit event happens, and then you look at kind of the number that comes back to you, and you're like, what? Where did it go? And I think you're having this normalization of incredible levels of dilution today more than ever before. Do you see that and worry about that?

**David Frankel** [48:56]:

Yeah. Look, dilution, it's interesting. I look at Whoop versus Suno. We're so proud to be in both. But Suno has been a very quick journey. So if you look at how much lower the dilution is, part of it is just how quick the momentum of that has been versus a Whoop, which is hardware, took a long time. Raised a lot of money along the way. Unbelievably proud of this company. But some of these companies, it's incredible how little dilution there is because the pre just goes through the roof.

**Harry Stebbings** [49:28]:

We're seeing also a lot of very low dilution but large rounds. They're, like, ramp raising you, like, 500,000,000 at a 40,000,000,000 price, and actually, kinda seemingly no kind of 50,000,000 rounds at a billion dollar price. How do you think about and reflect on those? Just a brilliant product for founders that they should absolutely take advantage of, a normalization of continuous funding because they do more more frequently. How do you think about those?

**David Frankel** [49:55]:

And this goes in every single direction. You've gotta be producing and you've gotta get into the rarest of air there. And probably there's a secondary opportunity in that kind of situation for us. So we look at that, and again, we're in so early that at those kind of numbers, that kind of momentum, we're trying to sell a little bit of our position.

**Harry Stebbings** [50:18]:

Do you find LPs have changed? And what I mean by that is like, I speak to a lot of LPs now. And you know what? Honestly, we can say what we want. They've gone back to wanting t TVPI. They've gone back to wanting big numbers. And, they want DPI. Of course, they always want DPI. But they are still very impressed by TVPI, and they're very impressed by, oh, wow. You're in this glossy name, lovable, legorum, mccor. They're still that. Do you find they've changed, are they still the same animal?

**David Frankel** [50:45]:

There's lots of change because of who was doing this fifteen years ago and who's doing it now. You have to have some allocation, and the big funds provide these containers for the large endowments and the large public investment corporations. If I think of the same LPs that have been with us for a long time, a lot of them have minimum size checks now. So we're too small for quite a few of them. It's like, if I can't put $50,000,000 to it. And I think it just reflects the inflation of the entire environment. There are a bunch that really do need the TVPI, particularly the fund of funds, because of who they're selling to. By the way, we've seen fund of funds do secondaries of their entire fund. So we go, Oh my god, you're in fund two or you're in fund four. You should never sell, right? And it's not about you. You're a rounding error in this fund and it's got three or four good names. And I think what they're trying to do is give liquidity to their LPs for the next fund. So we've seen, when I talk to you about secondary, it's in a particular name we've seen an entire fund, billion dollar fund, easily just sell the whole fund or sell a vertical slice of the fund. What's going on here is the finance around VC has become so much more sophisticated. I don't know if this is good for the entrepreneurs. It could be because it just means there's way more liquidity in every direction. And I think there, if you're a winner, it's great because you can manage the secondary to some degree. And if you're not on the winning side, in terms of the entire ecosystem, it can be very tricky. By the Harry, I talked to you about this on this podcast. We spend, other than thinking about some secondary in our very mature portfolio, I spend very little time on this. The beauty of this is I am not a financial animal. Ultimately, I'm much more of an entrepreneurial, curious animal. I'm looking again for these wizards, I don't know, these wayfinders. I'm looking again and this is the problem for me in a way is I'm looking to repeat a success. I'm looking for the next high. I'm looking for a Noah Glass. I'm looking for someone who is that focused on and has a vision and will not take no for an answer. That's how I'm spending 90% of my time. I'm not spending much time even on LP management.

**Harry Stebbings** [53:13]:

Do you think we have less loyalty than ever? You said focus there on the founder side. You see founders have angel investment portfolios that are as big as our fund portfolios. You have them doing side funds. You have them doing two companies at once. You have them leaving very quickly, often, in six, twelve, eighteen months. Is there less focusloyalty than ever?

**David Frankel** [53:35]:

We've definitely seen evidence of that. We've also seen people who stick it out way beyond what is rational just because they're obsessed. So I think on the margin, you see some of these actors. And we've seen founders, so called founders, and they were like kind of the founder, but they got a CEO involved, and then they became exec chairman, and they used their brand power. And I think shame on us, and we did get involved in some of these situations where we were dazzled, and it was like, you know, second time around, is that person gonna stick around? And some of it is just didn't get big enough fast enough. So there's some abandonment. I still see that the vast minority of the time. Like, think it's easy to extrapolate and go, That's a trend. And I could be very Pollyannish about this. But for the most part, I see founders wanting to make it work. Second time founders is a little bit embedded in that question. And the question is, if you've done really well, what does it take to move the needle? And I think overall we've done a little better on second time founders who didn't do that great up front. They did okay, right? It's life changing. Like, the first million dollars is so life changing. But they're really hungry. They've learned some lessons. They've got one or two people that will join them on the next journey. They've learned some lessons, and they are hungry. They're in a hurry as well. We've done better there than generally with folks who had great outcomes and kinda said, let's go again. Because those are the folks who got bored and went like, not big enough, not fast enough.

**Harry Stebbings** [55:13]:

What does no one know you've been very successful. What does no one know about making money that you wish you had been told earlier?

**David Frankel** [55:21]:

You kinda start to go, the stuff that really matters is kindness and how we interact with each other and how I left you, how you made me feel. And all the rest is fluff at some level or another. We're like our phones have become these remote controls for our lives. Actually, the entry price to get what you want when you want, if you want a vehicle there, if you want your food there, if you want to book a flight or a train ride. Earlier last week, the plane is delayed literally on the Amtrak app. Two seconds later, ask the Uber to go to Amtrak, go to Penn Station instead. The degree to which we can get what we want when we want at any level, you don't have to be that wealthy to get it, is insane. So what's happened is our level of expectations have just gone up through the roof. I don't think that's just about you and me. I think that that's the perennial equation of satisfaction equals perception minus expectation. So it's just much easier to not be satisfied anymore because our expectations are so high. Perception, it's one thing when you go into a five star hotel, have this huge expectation. You walk into a three star hotel, you have a much lower expectation. Well, extrapolate that equation for life now. So it's easy to get pissed off. The antidote to that is stopping for a second and saying, How would Harry feel when I left him today? Did he feel like I gave him a real hug and I was kind? And I think that's going on in my 50s now, is how do I leave people? How do I leave the world? How do I leave the entrepreneur? Was it like we squabbled over the last, you know, percentage point, or it's like just this journey's been awesome?

**Harry Stebbings** [57:04]:

I always think there's energy drains and energy gains, and how you leave someone is how you're remembered. Going just going back before we do a quick fry, I do have to ask, how does this landscape change with OpenAI and Anthropic? They are so seismic in terms of just sheer size. Both will be trillion dollar plus, potentially close to 2,000,000,000,000. How does that change the landscape, do you think?

**David Frankel** [57:24]:

For the better. I remember the Microsoft Google case going on forever and Gates going, you know, We are disruptable. At the time, like, Who could disrupt Microsoft? And turns out, you know, was Google. And then you go, Who can possibly disrupt Google? And then you look at OpenAI and Anthropic and you go, Wow. If nothing else, and there's so much else, like if you look at the top of the funnel in terms of where you start your search, when did you last start a search on Google? Right? It's just mind blowing, that displacement. And the good news in this environment and this ecosystem is that they will, too, be displaced. So the platform has changed tremendously. Do you think Google

**Harry Stebbings** [58:04]:

has been displaced in life?

**David Frankel** [58:06]:

No, I don't. I think Google's a net winner. Do think Microsoft has been displaced? I think Microsoft have done a crappy job of AI, generally. Google is actually, if anything, in poll position because they come from that environment, and the ability to search with context, the ability to apply AI with context, is just incredible. But they're having to fight like crazy for it. Microsoft, it's not clear to me that they can get back because their AI feels second rate compared to the top three or four. So there's a platform change. There's always been a platform. You could argue that radio, television, Internet was a platform. Can you do well in that platform? Oh, hell yes.

**Harry Stebbings** [58:47]:

Do you think that will lead to a ton more venture money coming in with a huge amount of money going back to LPs from the returns that are generated? They'll plow those back into venture.

**David Frankel** [58:57]:

So the returns at the top are gonna be incredible. They have to be. And I think that that capital is gonna spill over into venture and all sorts of investing. You alluded to it earlier, Angel. I think luxury, right? Like, think if you own a luxury property, I think San Like Francisco property prices. Oh my god. Like, San Francisco is Rome. I was there like six weeks ago. San Francisco and the Bay Area is like and it's more San Francisco than the Bay Area is back on steroids. It's like going to Rome. When people write off The United States, which is to me still the greatest country in the world for venture capital, I go like, when were you lost in San Francisco or the Bay Area? Because it is insane at the moment. What's going to happen is there's always boom and bust. So a lot's going to come out of the system at some point. Are we headed for another .com crash? Definitely. If is not a question. When? Nobody knows. But is there a lot of capital, a lot of gain coming out of the system and that will be reinvested in venture? And it may not be in classic kind of structural venture. It may just be in angels putting money all over the place, and some of those angels are gonna know people that worked with them or for them, and they're gonna I think you can bypass traditional venture to a great extent, and that's the challenge for us. That's the challenge of how do you stay relevant in this environment when there are so many alternatives.

**Harry Stebbings** [60:18]:

Final one before we do a quick fire. Do you buy the commonly stated concern about smaller teams, job displacement, and a concerning future for human participation in labor forces?

**David Frankel** [60:30]:

The underpins to Endeavor are getting better and better and better. I remember when we went from servers to cloud, and that was like, wow, get all of this for free, right? I don't have to do any of that. Security and servers and I forget that. I just do cloud. If you look at where AI and where this foundational platform layer kicks you off, It is incredible what you can do with very few people. And we are looking at certainly sub 10 people companies achieve a lot. Do I think that we're gonna have mass unemployment because of AI? And you're seeing a lot of leadership now agree with the view is no. I think we're gonna see tremendous productivity gains. I think like every wave there are the haves and the have nots. And if you're not training and playing, it's a little bit why youth has an advantage because out of college, if you're tinkering and playing, you are familiar with the tools. You can use the tools. And it used to be the haves and the have nots were like have data. I talked about this with Noah Glass and Olo all day long going like the value of having data and using that data and by the way, it's yours to lose if you don't enrich that data. Now the value of having these tools, it's becoming more and more binary. But I do believe you'll see swathes of people retrained on this. And I think you're seeing it globally. I think you're seeing it as an opportunity in low cost environments, in places that are not Europe, not The US, not the North, where you can skill people up, and you can provide these skills to the rest of the world at tremendous cost advantage. My worry

**Harry Stebbings** [62:12]:

is it's much easier to train than it is retrain. And actually, the 22 year olds coming out of university who are tinkering in dorm rooms with Claude, and kind of, they're not super AI pill, but they're mentally plastic to it, and they're gonna be pretty good versus Simon or Claire who are 45. They've always done their job in accounting, and they just are not so mentally plastic. The only advantage that

**David Frankel** [62:32]:

Simon and Claire have is they are very vertically knowledgeable and relevant. So sometimes in terms of sales, like if you're selling to yourself, there'll actually be very good salespeople. This is a theme that I'm kind of interested in, services business, where you won't buy that from You want to see your auditor at some point. You're prepared to say, know AI will do an amazing job, but at some point you want me to come see you and just kind of like go, you know, I haven't left this whole thing to AI, right? Like I actually know what I'm doing. So I think there'll be people who are vertically relevant who'll be able to sell. And there are many industries where the relationship still matters. At a certain point, if you've got litigation and $100,000,000 you can get AI to write that little contract for you where it's thousand dollars on the line but you've got $100,000,000 litigation. You want to look at me and say, Dave, your ten years of experience, I need it right now. So I think there are times where knowing a vertical, being relevant in that place, and in the service industries, I think it's good for The UK, by the way, I think there'll be a ton of people who are still needed for the human interface. That's not going away. I think that a lot of the work that was grunt work and human work behind it, going away.

**Harry Stebbings** [63:45]:

On the services side, I think it's just a expansion play, which is like so much of the things that you couldn't afford a lawyer for, you'll use and you'll get great benefits from. That is just a TAM expansion play.

**David Frankel** [63:56]:

I think insurance, lots of admin, like lots of life insurance. Wanna There's been a lot of direct life insurance sales anyway. But I think that in bigger ticket items, having a human who gets it as the interface, there's still place for that.

**Harry Stebbings** [64:11]:

There was something interesting. I had this incredible founder, June, who's the founder of a company called Simuli, which does simulation markets. And he was like, we will have companies spend a 100 to 200,000,000 on one model kind of result because that model result is so important, like the output of one query. And I was like, wow. That's a really interesting world where you will spend a 100,000,000 on Anthropic telling you the answer to one question. What's the size of that organization that will spend that kind of money? Oh, P and G, Coca Cola, NVIDIA, Visa, you name it. Is it worth us sponsoring the World Cup for a ten year exclusivity period visa?

**David Frankel** [64:48]:

Right. I think that governments and defense organizations, some kind of speculation with data of the future, I think that's a very interesting play.

**Harry Stebbings** [65:00]:

Do you worry that Trump's been good for business but bad for everything else? Is that a hard balance to hold in your head? I ask as an outsider, genuinely curious. I think you have to hold

**David Frankel** [65:11]:

many truths at one point in time. The question is, did Trump create this environment, or is he presiding over this environment and getting credit for it? I think with all presidents, they arrive and they get credit for the environment as it is, yet it was created many years ago. And letting AI thrive in The US has generally been a good thing for the tech industry in The US. The level or lack of safeguards on that could well be problematic. But net net, like if it's good for business, it's good for The US. I think Roosevelt said that. That's what these administrations have said. And by the way, I think that a lot of the tech backlash around Biden was for this reason, whether it was true or not. A lot of insiders say to me it was BS, right? That for the most part, Biden was super pro business. And if you look at the subsidies for energy, if you look at Tesla today, this is the thing that kind of I don't really get about Elon is the non dilutive government funding that Musk got for Tesla from the Biden administration was huge. So without being political, net net, government in The US has been pro business for a long time, and I think that the country is really reaping the rewards of that. There are two AI superpowers in the world. By the way, what's so fascinating is in the 1820s, China was the economic superpower of the world. I don't know if you knew that. No, I didn't. Yeah, so Great Britain displaced displaced China. China. A lot of it was Industrial Revolution and then The US displaced Great Britain. In The Economist, there was a chart on this. But in the 1820s, 25% of the world's global economic output was from China. It was the biggest economic machine in the world. And really what you're seeing is two superpowers emerge for sure. And I think a lot of this is gonna be about AI. AI flows into not just industry but in terms of what's going on in defense having been very, very early first check-in Shield AI, and watching how that's played out. The US needs it. Like, our enemies have access to all of that on

**Harry Stebbings** [67:26]:

steroids. I'm terrified about China right now, to be honest. When you look at the power and strength of their open models

**David Frankel** [67:33]:

But that goes back to thinking about Microsoft and Google being disrupted. What could possibly you know that Anthropic and OpenAI are going to be disrupted. It's unequivocal. Our whole careers are about disruption. Those platforms never ever stay forever. Where is it gonna come from? Excellent chance it comes from China.

**Harry Stebbings** [67:53]:

It's coming. 100%, but, God, we haven't had enough time for them to establish their incumbency yet before they're already being taken down by Chinese open source models. It goes to the point on the speed of innovation cycles.

**David Frankel** [68:04]:

By the way, we haven't even touched on underlying computing. So if you look at photonic computing, if you look at what's coming down the line now, so you looked at Intel at a point when that can never be disrupted. And then NVIDIA, it's just mind blowing. What's coming to get NVIDIA? The photonic computing plays right now where it's not electrical anymore. It's photons. So if you look at the data centers where everything that can be optic fiber now is, So every single connectivity piece of hardware is fiber. The only thing that has not been nailed is the chip. You're gonna see optic chips which are very, very energy compliant. So when people talk about the data centers and the energy sucks, that's gonna change. In my view, if you say in ten years' time, and I am not a thematic investor, but I am such a deep believer in the status quo being changed always and nothing stays the same. I think photonic computing's coming down the line, and I think that's gonna be the NVIDIA disruptor, or NVIDIA's gonna buy those companies. Okay, and

**Harry Stebbings** [69:07]:

the capital intensity required to build a photon company, I think, or an energy company as we're in some, it's just dramatically more capital intense than prior technology. Again, going back to my point, you need more money.

**David Frankel** [69:19]:

Well, this is where The US could be deficient. If you look at the amount of money that's being spent in China on energy efficiency and energy research now, I don't think we're spending enough. And by the way, that's a negative of the Trump administration is we need much more money being spent on R and D. And I think there was a view that the universities are squandering it. To a large extent, I agree with that. But I think that we tapped off a lot of DARPA R and D that finds its way into every nook and cranny of the economy, and we need more of that R and D. We see some of it. I live in Cambridge, Massachusetts. We we have some of the best R and D organizations on the planet. If you look at MIT, Harvard, Northeastern, BU, BC, what's going on there, and cutting that spend, which goes back into society, I think is problematic.

**Harry Stebbings** [70:08]:

Totally get that. Another one, though, is more challenging, I think, to change is just policy and regulation. Chinese approach to policy and regulation is almost none. It's none. And it means that you can bluntly build and deploy so much faster. Mean, Europe's the worst. The US is

**David Frankel** [70:23]:

I'm tough not in biotech, but when I talk to friends who are in biotech venture investing, they're all flying to China all the time because they're going, Look, in terms of R and D, in terms of licensing, in terms of anything goes, and in fairness, it's not a totally anything goes environment, but there's so much more grassroots activity, and a lot of it has to do with regulatory environment. What would cause you final one. What would cause you to increase fund size? Oh, I would say, if I am honest about what we did early on, is as an angel I had said the risk premium for the seed stage was way overstated. So the premium for experience, right, like I couldn't get that. A lot of the folks that I got involved with very early were graduating. They were Noah Glass, Jack, you name it, Eric and Micah. There was a dislocation between the perception of value later versus earlier. And that has been largely narrowed and crowded out. So if there was some kind of arbitrage. Harry, we didn't come at this going, I'm obsessed with economic arbitrage. We came at this going, I'm obsessed with great founders and I want to vicariously be on that journey. But if you had to look at this retrospectively and say, What did we do in economic terms? There was an arbitrage. There was a real arbitrage because the risk premium at the seed stage was way overstated. That has changed completely. What would cause me to raise a bigger fund? If I looked at Series A or Series B or Series C and went like, There is such a value opportunity because everybody's abandoning this. I don't think it's true at the moment. I think just capital and money finds its way to everything. But if you went, So many Series A companies are orphaned and there's amazing value. There hasn't been one to 10 to 20 in ARR increase in one year, but wow, they're on track and that looks like it smells like Olo. It looks like SeatGeek. I think that would cause me to say we should be investing $10,000,000 at that stage. So it's not momentum. It's a sense of, wow, like, I can't believe that others and I have been very tempted there. I've been very tempted to say this company is doing incredibly well on the revenue side and it's being undervalued.

**Harry Stebbings** [72:41]:

Final final one on premise for the quick You say that about Olo, and I love I think Noah's one of the great, awesome human dude, it's seventeen year journey to a 1.6, $1,700,000,000. Right? So 2,000,000,000 exit. 2,000,000,000 exit. I love Noah. I love Olo. It's an amazing business. It's an amazing journey. But when you think about, like, utilization of cash most optimally, seventeen or eighteen years, $2,000,000,000 exit, the IRR is not amazing. How do you reflect on that and and just find that versus maybe hotter rounds? Yeah,

**David Frankel** [73:12]:

I mean, the outcome was, it's publicly known, eventually, TOMA Bravo. We took the company private for about a $2,000,000,000 valuation, so not bad for a few years of work. And if you take it on an IRR basis, you're probably right. The journey and the fun of it was just enormous. So being involved with Noah where it was Noah, a few other founders, and me from the beginning, and being on the board until that sale was just the ride of a lifetime.

**Harry Stebbings** [73:39]:

Okay, listen, quick fire round time. What have you changed your mind on in the last twelve months? What's

**David Frankel** [73:46]:

been surprising and what I've changed my mind on a little is where AI should have impacted like crazy, and I've seen lesser impact so far, With all the hype, with all the momentum, like AI changes so much in terms of software and enterprise and SMB other than the models themselves and some good stuff around human interface. So a lot of stuff around the voice has gotten a lot better. I don't know about you, but I would have expected much more around consumer AI. So I've seen Suno. But in terms of changing how I do stuff, I type much less. I speak much more in terms of communication. I would say there are so many kind of consumer areas that I feel are not yet played out at all. When you're doing Suno at $5,000,000,000 what are you underwriting it to? I think that the folks investing at that level are going, This is a Spotify disruptor. That Spotify and Apple Music, it's a big bet that. We gotta

**Harry Stebbings** [74:44]:

go from creation tool to consumption tool.

**David Frankel** [74:46]:

Oh, totally. Totally. That's why Jack from Snap was brought in. Interestingly, I was at a conference with Martin. Martin on a Martin Camacho, who's the CTO of Suno. He was asked a question, If a large language model could do what you do better than you do it, would you slot that in? And you're talking to the CTO, the guy who's built the whole model. The entire Suno model is from the ground up. And without missing a beat, modern goes, Wouldn't think twice about it. It goes to your point of this is a consumer product. The experience, the interface, think Spotify, That's what we offer. How we get there is obfuscated from the user. The user couldn't care less. Like, whatever gets you there. Did you ever

**Harry Stebbings** [75:31]:

predict the speed of that? No. Definitely not. Do you remember the days when Slack, one to 10 in eighteen months, was like the gold standard? I mean, so you know, it's multiple hundreds of millions. Mean, 500,000,000 or whatever it is now. It's nuts. No. Goes back

**David Frankel** [75:46]:

to Uber. You know, when Eric's asked, how did you know? How did you know? And Eric goes, I didn't. He said, the company I saw before, the company I saw afterwards, like, we underwrote those in the exact same way. Anyone in my seat who says, I knew, is just full of shit.

**Harry Stebbings** [76:03]:

I I absolutely love that. What's been the most controversial deal that you've done internally?

**David Frankel** [76:08]:

What can become controversial is the what or the where. So certainly Coupang was like got back I said to Eric Parria, and he said, you know, do you even know if it's north or south? But the magic there is I am based in Harvard Square. So people go, How do you get to Korea? Like, how do you get to all sorts of places? And the answer is Harvard Square. So Bomb drops out of HBS after his first year and comes to see me. And another controversial company was probably Shield in terms of the what it does. So I would say the whole partnership didn't necessarily love defense drones. And early on, it was like, is this only defense? So I love it because it's certainly taken us to some very controversial geos and controversial whats. Our

**Harry Stebbings** [76:54]:

prediction marketplace is just legitimized gambling.

**David Frankel** [76:58]:

It has to be. I mean, if you look at, like, Kelshi and Polymarket, what's the difference there between DraftKings and Betway? Seem very similar to me. But by the way, this will be controversial. TVPI versus DPI. The one looks like a prediction market, right, and the one's real. Like, I could say the same. You know, TVPI looks like a prediction market, right? But,

**Harry Stebbings** [77:18]:

I mean, candidly, when they're doing $2,000,000,000 an ARR, who gives a shit? The one thing that you worry about is a Trump change in administration and what that does to regulation around them.

**Unknown** [77:28]:

Yeah. That's

**Harry Stebbings** [77:29]:

a different game. Yeah. What do you know now that you wish you'd known when you started Founder Collective?

**David Frankel** [77:33]:

So for the most part, frameworks have saved us. It's also the place where, if I look at some of the deals that we didn't do, and we just went we used valuation as shorthand to say no, terrible mistakes. So Clavio loved Andrew, loved Ed, came to me first, came through Hugo von Furan, who also sent us Suno, and didn't do it because of the framework. And the framework allowed me to easily say no. So we'll miss a lot. We'll make plenty of mistakes. I think I've freed myself, like you, a little more in that area and just go, they're extraordinary. But the frameworks have saved us as well. Penultimate one. Biggest advice on a happy marriage and relationship? Kindness and being present. Being present with each other. Like, I think of this at dinner. At dinner time, no phones are allowed anywhere near the dining room table, and I don't take my phone to my bedroom. Like, my phone is never alongside my bed. Here's the rub. I don't need my phone to be distracted. Here distracts me perfectly. How to be present and involved and look you in the eye and kind of make you feel with my body language that I'm hearing you, that I'm invested in you. I think the same thing that we think of in founders, like happy life, your kids, your wife, your siblings, your parents. This is the lifelong goal. Like, I don't I have not got this nailed. But how do you show them you're present, you're there, they matter to you? And that's that's the quest.

**Harry Stebbings** [79:06]:

Final one. What are you most excited for in the next ten years? I I look at it like me. You know, my mother and I walk marathons. She's got MS. I think there'll be amazing discoveries for chronic conditions, which we always just assumed would be forever, and that could change millions of lives. I think that's super exciting. What are you most excited for?

**David Frankel** [79:23]:

I mean, you're leading the witness in a few ways here, But I would say that each wave brings things that we couldn't imagine. And I look back to driverless cars, and there was a promise that that was like five years away. And it turns out, like, twenty years from now, I saw Waymo driving around London. I think it's coming here soon. We're not quite there. And yet we're back in the it's slow, slow, slow, and then it feels like overnight. And of course, if you're involved, and this is, again, the intoxicating part of what we do is you know before the world knows or the world cares, but you know that it took a long time, and yet I think we're on the threshold of a lot of really interesting stuff. Like, I think that you and I could be buying the very lost driven cars. Like, I think that in five to ten years' time, like, our kids will not need to drive. And I think with AI we're on the threshold of a lot of that. And there's a lot of doomsaying. There always is. But in terms of discovery, in terms of what we know about the world, in terms of health, right, in terms of, you you look at chemo and the number of friends of mine who have been treated, who have passed away, and you look at chemo and you go, That is, like, prehistoric. And I think that we are, with AI, with the amount of compute going on in healthcare and other realms, like there are solutions coming through, not fast enough, but I think it's so exciting, what we're involved in.

**Harry Stebbings** [80:49]:

It's very exciting for me too to hear you say that because I don't actually have a driver's license, and so you could

**David Frankel** [80:55]:

assuade me or relieve that necessity. Harry, you live in the most walkable, the in summer, the most walkable, wonderful city. You don't

**Harry Stebbings** [81:03]:

need a driver's Oh my god, dude. I never ever need to drive. Thank you so much for doing this. Thank you so much for eleven years of friendship. Honestly, it means so much to me, and you've always been so kind to me. Harry, you've gone

**David Frankel** [81:14]:

from strength to strength, and that's my wish for you is keep going from strength to strength. You've been a great, great voice in this environment, a great voice in the world. Thank you so much. Thank you.

**Harry Stebbings** [81:26]:

But before we leave you today,

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