
Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. Rory O’Driscoll is a General Partner @ Scale where he has led investments in...
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Harry Stemmings
The Thrive strategy was brilliant. Buy the best property on every block. It's like Monopoly. Integrate block stripe, tick the OpenAI block, tick the infrastructure block, database tick. Then you just go home when you're done and you wait for the checks to roll in. It's genius.
Jason Lamkin
Why struggle to pretend you can do 8x over 20 years on a seed fund when you can just write one big check into a winner and call it a day and achieve liquidity in a quarter of the time, the multiple will be lower, but the absolute return will be higher. Like, it's so stupid. Like, see this for suckers.
Rory O'Driscoll
This is 20 VC with me, Harry Stemmings. Now, today is a new form of show. We analyze the news from the last week. So we discuss Andreessen's new funds, founders fund's new $4.6 billion fund, rippling versus deal. When will IPOs come back? And joining me, I really wanted two amazingly smart people, but they also had to really not give a shit what other people thought of what they said. And so I chose my dear friend Jason Lamkin, always one of the best to have on the show and who I think is one of the greatest investors who bluntly isn't given enough airtime. Rory O'Driscoll. He's a GP at scale and an early investor in Bill.com, box, DocuSign and WalkMe. This was so much fun to do. I want to hear your thoughts and feedback. Let me know what you think of this show. But before we dive in Today, here are two fun facts about our newest brand sponsor, Kajabi. First, their customers just crossed a collective $8 billion in total revenue.
Unknown
Wow.
Rory O'Driscoll
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Jason Lamkin
How?
Rory O'Driscoll
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Harry Stemmings
You have now arrived at your destination.
Unknown
Jason Rory, I'm so excited to have you here. I was thinking, who are the most insightful venture investors that I can bring together to discuss today's news? Sadly, Bill Gurley turned me down, so thank you so much for joining me today, guys.
Jason Lamkin
What was Chamath doing by the way? Was he turned you down too?
Unknown
He was teaching Larry Summers about economics. So I see it's going to be pictures.
Jason Lamkin
I love It Rory, since we have you. Harry, go on. But I want to know why these billionaires are so bitter on Twitter. I think Rory will have an answer for us. Harry.
Harry Stemmings
Well, first of all, you must be bitter if you bought this product four months ago and said they're really smart and really intelligent and they're going to run the country really well. You must feel like a bit of a buffoon. And when you feel like a buffoon, you've only got two choices. Double down and bluster your way out or fold away quietly. And billionaires tend not to fold away quietly. So they're just going to bluff their way out and say this is all part of the plan. It's a tough look, by the way. It's a tough look, right, but whatever. I think what it shows is just because you really understand one domain, investing or technology, it doesn't automatically make you understand a totally different domain, politics. And I think you're just saying, look, it turns out low IQ is not transferable and you can't walk into a different game where people have been playing for 20, 30 years and think you're good just because, hey, you're smart.
Unknown
It's so interesting you say that because I'm actually just really. I wanted this to be a very free flowing conversation. We just released a show the other day with Victor Lazarte From Benchmark, a GP at Benchmark and he said the generation of SaaS investing before is dead spreadsheet. SaaS investing where you look at NRR, you look at growth rates and you know, you can reasonably predict good quality companies. That's dead. Nabil at Spot said the is the way that we've invested now dead and do we fundamentally have to change all of our rubrics?
Jason Lamkin
Rory, you've been thinking about actually, you know, when you and I first met. Harry, when Rory and I first met, he was the first guy that really opened my eyes to, to this question of SaaS metrics. And I met Rory. I think the first time I met him was at like the first upfront summit in like 2013. Okay. And I think that was the first time I met him. I might be wrong, but I think so I asked him what a good SaaS startup was because I didn't know at the time I'd done pipedrive in Algolia, but I didn't know. I made this up when I worked at this other VC firm. We didn't have a consens what good growth was. And he said 1 to 10 and 5 quarters or less is S tier 1 to 10 and 5 quarters or Less. And I copied that with attribution. I use that as my investing yardstick for years, right? And then he's done the Mendoza line, right? But then I'll, I'll say one thing and then I'll shut up. And then I think in late 2020 and 2021, it seemed like every startup met that. So like literally I had two startups in my portfolio, two of them that a VC all three of us know really about. One of the best cloud VCs he offered them. I remember term sheets at high nine figure valuations without talking to the founders, just, just immediately in late. Because you only needed a spreadsheet in late 2020, early 2021. Did you? If you're growing 20% a month at double 10 million in ARR, you didn't actually need to know what the company did in SaaS for a while. Right? And so I think that is dead.
Harry Stemmings
Sure the answer is, yeah, it's done, but. And the question is why and what's actually done? I mean, I think that spreadsheet investing is one comment and then SaaS is another comment. There were two proper nouns in that sentence. And it's true that first generation SaaS investing is definitely, I don't know if I'd say done, but you've hit a plateau in terms of that. There was a 20 year period where it was pretty obvious what to build and you built it. And because the broad direction was obvious, all that was left to analyze was the math. Right? It was pretty clear the direction of travel was take X, move it to the cloud compound for a long period of time, get a great outcome. Pretty straightforward. So the only thing you had to do, it was actually fairly simplistic. Evaluate the relative growth rates of different things and pick the thing that's grown the most at the most efficient level. And There was a 10 year period where these companies didn't change. I mean, I invested in box in 2010, it didn't change. I didn't think. Jason and I, we competed in the signature market, DocuSign and Echoesign. The thing that we invested in in 2010 was the exact same in 2024. It's stunning. So there was no conceptual thinking about, you know, what should we build next. It was just like build this thing and sell as much of it as you can and that's done. Now two things happened at the same time. The existing market saturated, so all the growth rates flattened out. Anyone who needed a Zoom account or a DocuSign account has a DocuSign account because they all got it in court. Right. We're done. At the same time, these new AI startups took off where Jason and I were just chatting on this. Unlike the SaaS thing where, you know, stuff was the same for 20 years, this shit changes every. I can say shit, right? Yeah, this shit changes every six months. It's like literally I've had companies acquire and lose Product Market Fit two or three times in a two year period. It's terrifying. So it's way harder now. I mean, when it works, it's way better, but. Oh my God.
Jason Lamkin
Yeah, that's the hard part. It used to take you five years to fall out of Product Market Fit. Now it can be five weeks. When all three of us started, I mean, Harry, you were, you were dropping out of school, but literally you could count on if you hit Product Market Fit and you had a decent team, like there are exceptions. You had five years, you had five years to run and you had to reinvent yourself around year four to five. And you can't count on any of that today, can you?
Unknown
What has changed that has made Product Market Fit a very transient and fast moving thing rather than something that you held for reasonably long periods of time.
Harry Stemmings
Probably two things. One is Model Progress. Probably has something to do with a very deep level, is the things what you can do gets better. And then the second thing is we're still at the figuring out stage of what you can do. Even absent Model Progress, there's a lot of, oh, we thought they would do it this way. And you fast forward six months and it turns out, well, they do it this way for a few months, but then they want to do it a slightly different way. And in fact, if you don't add more value, the customers say, no, I can do something better somewhere else. So we're in this exploratory phase, which makes sense that it's changing because we're not yet locked in. I mean, I remember there's a period from about 99 to maybe 2002, 2003, where what a SaaS company was, was changing. I mean, you had Salesforce nailed it. But before that there was this NSP weirdness and it wasn't quite sure what a SaaS company should be. And I think it's the same thing here. It's not clear how. And it's much harder here because instead of just automating some back office shit, you're really trying to automate the head of the worker. Like you're, you got to get in the head of the sales rep or the SDR or whoever you're augmenting and assisting and just figuring that out is really hard. And then it changes as the. As the AI can do more. So, I mean, go, Jason.
Jason Lamkin
Yeah, I also think we were talking before we went on about a hot AI SaaS company where literally the team was all on Adderall. And it was joke, right? It was true, but a joke. But I actually think in SF today, most of the startups we work with aren't Adderall. Not literally necessarily. I mean, I don't know. But all the best startups I've invested in are working 7 days a week, 12 hours a day. In the office. In the office, 7 days a week, 12 hours A day. Now, it is true, as they hit super scale, their. They're being more flexible for folks with families and more heterogeneous, but man, and everyone is working 7:12. And it's a vibe. And you can make fun of vibe coding and vibe moding, but when. When your competition in 2021, I mean, people are working 10 hours a week from home, guys, literally, they were working 10 hours a week. Okay? Now your competition's working 100 hours a week. For real, not for fake. If you haven't evolved, you're gonna die, right? Especially when you can add AI on top of it, you're gonna die.
Unknown
I just want to try and go back to product market fit being so transient. Because if product market fit is transient and revenues are highly unreliable or unsustainable, as we're seeing with your Gen AI companies that scale to 20, 30, 40, 50 million very quickly, but with a lot of potential sugar high. If we've got revenue unpredictability, PMF unpredictability, what are we underwriting?
Jason Lamkin
Yeah, I want to know what Rory says, because I don't know right now.
Harry Stemmings
If you're not understanding that you're underwriting more risk, you're missing the movie. You're taking on more risk. What you're underwriting is the upside. You know less at every stage, on every check you're writing today, you know less than you would have known 10 years ago at a similar stage. SaaS company, a lot less. A lot more. Things can go wrong. But on the other hand, the upside is there, and it's huge. You're just taking on more risk for a dollar of revenue is the upside there?
Unknown
And it's huge because the prices are inflated much higher than they were 10 years ago. It doesn't feel like you're getting Paid for the risks that you're taking.
Harry Stemmings
Well, disaggregating that because again, you inject the price into the equation. At the risk of channeling Monty Python, that was a reference to the Holy Grail, but I meant leaving aside price. In other words, do I think the outcomes of these companies can be huge and arguably even bigger than some of the SaaS companies? Yes. So quote, the upside is there. Now, the worst of all worlds, as you say, is if you've got high product, market fit, variability, high risk, still good ups, big upside, but then you pay up so much that even that upside has been competed away, then it's. Then it's a sucker bet. And yes, that would be bad. It's a very scary time to play the game today. We all do it because we enjoy it, but every time you're writing a check today, you're going, I know, a lot less than I did on some of these other things and paying a bit more. The upside is amazing. Oh, my God, look at that growth. But we've seen companies fall off the growth track in six months, so it's pretty scary. Turns out making a lot of money is hard in venture.
Jason Lamkin
You think we'll have more bimodal results where a lot of funds will just be massive unperformers because it's hard to assess the risk properly.
Harry Stemmings
Yes, for two reasons and we'll talk about one is each individual deal has more risk in it. And then on top of that totally separate thing, the holding periods have elongated. Right. And every year. Holding period. Elon Gates. One of two things happen. You roll the dice and if you win, you go up 30% and if you lose, you go down 50%. If you roll the dice three more times, by definition, one company will go up 2x and the others will go down. So yes, it's going to be. I mean, portfolio construction really matters here because you're in a riskier game for a longer period of time. And yeah, some of you are going to make it, but a lot even are not. Yeah, it's scary.
Unknown
I had Victor from Benchmark on the show and he said that portfolio construction doesn't matter. His first check was 8% of the fund with $55 million into. Hey gen. Which was.
Rory O'Driscoll
I thought a lot.
Unknown
Jason, we've spoken before about percent of cheque as a percent of fund. Two, three standard eight is a lot. And he said that bluntly, they can raise whenever they want to at will. So $500 million fund can be deployed in a year. We saw KP deploy a fund in 12 months. I guess my question to you is, if you're a brand name firm that can raise, does it matter?
Harry Stemmings
It always matters somewhat when people actually lose money as this thing from thinking about losing money, and particularly when they lose money two funds in a row. Even a brand name firm can hit a bump, right? I think someone as amazing as KP and Benchmark, no, I never take it for granted that you can win the net. You can, you can raise money. Because I'm sure Jason's had the same experience too. I raised our first independent, we raised my partner, Kate and I raised our first independent fund in 2009. You know, we were in the Lehman and AIG offices the day went bankrupt and it turns out they didn't need to add to their exposure of private illiquid assets that week. And you know, ended up taking it for granted. It was damn hard. It took a year to raise that money. So probably true for Benchmark and KP, probably not true for the other 898 funds out there.
Unknown
We were talking just about kind of like, hey, we see the growth and the question is, are we getting paid for it? What about the normal SaaS companies? There are thousands and thousands of SaaS companies that will listen to this and be going from 1 to 3 million an hour, maybe 1 to 4. And that was kind of good. In 12 months it was, it was decent 4x year on year in any normal world.
Jason Lamkin
It's a great, it's great, right? It is great. You're still elite.
Unknown
But can they still raise the companies that are doing triple, triple, double, double. It's not lovable, it's not bolt, it's not macaw.
Harry Stemmings
I think they can, but I don't think that's the issue, Harry. I don't think the issue is can the companies doing trouble, trouble double double raise. If you hear the story and you go, yeah, that makes sense. It's a SaaS, hasn't been made illegal. It's a totally good solution. It doesn't have AI magic pixie dust, but it solves the customer's problem. And the proof that it solves the customer problem is it's growing 3x3x2x2x. I would do that deal all day, every day. So let me put that out there. If you've got one of those, call me the real. And I'm mentally thinking of a deal I turned down two, three rounds ago that has done just that. And I'm an idiot. The real problem with SaaS isn't what you Just said the real problem is they're not trouble, trouble, double double. The real problem with SaaS is those tons and tons of SaaS companies that have slowed down from exceptional growth rates and 3x year, one year is exceptional, that are doing 50 million growing at 10% or 20% or 100 million growing at 8 or 9%. There are myriads of those and that's where the real question asks for what those companies end up.
Jason Lamkin
As for me, the triple, triple, double, double. I'm totally into it if the CEO is amazing, right? Because that solves for everything, right? But I will say I remember it was kind of almost a chilling moment to me. Maybe 15 months ago, I got together with another top cloud SaaS VC I've known since inception that all three of us know. And I got together with him and he said big fund. He said I'm only doing AI investing. And then I started asking other folks and here, listen, I don't have a survey. You're better at this than me and everything. I would say 70 to 80% of the folks I grew up with that were SaaS investors. Investors are not won't do those normal triple, triple, double doubles. You would, you are a top tier performer. But they're just, they're momentum investors and they want to put 200 million into the latest AI deal, right? And triple it in eight months. They want to triple it in eight months, 80%. I would say they won't take these meetings.
Harry Stemmings
What about this? I've often found when people have a, when smart people are using a heuristic, there's sometimes logic behind it. Maybe a more refined version of the sentence that they're giving you is I just don't believe I'm going to kiss all those sass frogs and I'm not going to find my prince. So mentally I'm not even going to bother because I'd say for me, most of the stuff I'm looking at is AI a priori and without data, I would assume anything that could have been done 20 years ago in SaaS probably has been done. So I'm not rooting around in SaaS land looking for a good deal. But if one was to crop up troubling year on year, you'd have to look at it, right? As I say, a modified version of that is not don't despair if you're in Sasland and you don't have an AI pixie dust story. But if you don't have the goals as well, then you're right. Then it's compellingly hard, you say?
Unknown
Compellingly hard. We all have LPs. I have a lot of LPs. Call me up and go, harry, what the happens to this company? Where am I getting my liquidity? I've got exposure from Jason, I've got it direct. And when you look at a generation of your data IQs, your calibras, your Algolias, the growth rates aren't quite what they used to be, the profitability isn't quite there. And it's a question of what happens to this generation of companies and where does liquidity come from?
Harry Stemmings
Look, it is the $3 trillion question. The reason it's a $3 trillion question is because that's the rough fair market value of privately held venture assets. And maybe half a trillion to a trillion of that is high growth, new stuff. And the other 2 trillion is mature, slower growth. SaaS and cloud companies that don't have the trajectory anymore for an ipo, but as yet have meaningful value. And I think that's the interesting thing is that if it was like I was around in 99, 2000, all the good deals went public and all the bad deals were so shit that by 2002, we closed them down, we said whoopsie, and we all moved on. You can move on from a $200 million, you can't move on from $2 trillion, right? So there's a huge amount of really grim industrial work that's going to have to be done on Evan's portfolio to manage these companies through to a meaningful exit. Because as I say, you can't walk away from $2 trillion that are not only your LPs, economics, the Euroeconomics, significant big companies, and they're so big that you're not going to walk away, but it's going to be a lot of hard work. One option, you just grind your way to profitability. You look at PEX and you look at consolidations. You know, you're going to see some private to private where you put the two or three companies in the same space together and try and change the economics of the trajectory. Maybe you'll see some smaller IPOs where people go, I know it's not a great market, but God, give me some liquidity. Price does all markets, you know, all of the above. It's going to be real, case specific, long and tiring work. But on the other hand, $2 trillion is real money, even in America.
Jason Lamkin
Rory, I wonder one thing that worries me. I wanted to write this up, but I don't have the data to support it because you have a much broader portfolio. I'm worried that the PE firms aren't trying to buy these companies. That's what I'm worried about. It's not the valuation. At least you have an option. I am worried that. And the private, private I think is a great idea. Right. Take two companies at 200, growing 20, take it public at 20% at 500 million, you've got a game. Everyone should look at that deal. But I'm just stunned. I used to see P hunting everything in the portfolio. I would come to sasrangual and every year I talk to some founder, I'd be like, well, we're here. I'm like, has a P firm talk to you? Yes, 20, right, folks. That in this sort of mediocre growth level, they're getting no tire kicking. Are you seeing lots of tire kicking? That's not happening because I ain't seeing it.
Harry Stemmings
We're not seeing a huge amount. And you're exactly right. And it's quite a shrewd comment, Jason. And I think the reason is this. PE guys ironically love the things that we don't love. And let me tell you what I mean by that. They love a boring ass software company in a teeny tiny vertical with 40% market share where they can screw the customers for the next five years by raising prices because there's nowhere else to go. Venture deals, SaaS deals, love broad horizontal markets where you can compete and maybe get a billion dollar outcome. So those are the companies that our industry's funded. And the problem is when you fail to get the billion dollar outcome, when you discover your market is tinier, or when you discover that an adjacent company is competitive, you're left with this subscale company that doesn't have the same pricing power. You're in a perfectly good big market, but there's a bigger company out there that can grind.
Jason Lamkin
Yeah, there's no pricing power with no pricing power.
Harry Stemmings
And PE guys just hate that because they can look at it and go, I get it, you're doing 100 million now you can grind it, but you can't take 30% of the cost out, raise the prices and get the same thing. So I agree. I think that not every deal at $100 million would be interesting to Pete. If they have an adjacency in the same space, then they might buy it because they can load it on. But when you look at the things they love and you look at the things we make in venture, they're not the same deal. And it's very clear when you list the kind of companies they do, it's like, oh, obscure vertical accounting software for an obscure vertical. Massive market dominance. And no one's ever going to fund a competitor. They just run that math. They fire all the salespeople, double the prices, cut the engineering down, kick off 40% cash flow in some of the broad horizontal stuff. In a CRM company or let's just say a first generation customer support company from 2016, if you cut off the R and D and the sales and marketing, your gross dollar retention will be 80%, you won't be selling any new shit, you'll be declining and your product will become irrelevant in two years. But other than that, have a great day. Those companies you are. And Jason, where do you put those companies? You have to. One of the things you said earlier about you probably have to find a way to fund new growth while at the same time building a new product. It's a much harder play than just sell it. Pe, as I said, it's all the other things we talk about.
Unknown
You said that kind of the difference between what venture likes and what PE likes. And hey, if we do this and this, we can see the billion dollar outcome in venture, kind of relating it to news. But Andreessen announced a $20 billion fund and the plans around it, General Catalyst, have $8 billion. Lightspeed. I don't know how many billion dollars they have. It's so confusing with all their different vehicles, but billions and billions. Billion dollar exit. Thanks for paying for the Christmas party. I'm being serious. If you have 8%, it's 80 million back.
Harry Stemmings
I mean, to state the banal, they're obviously not focused on billion dollar exits. They're focused on a much smaller number of much larger exits. And that's the bet in a nutshell. If you're going to make those kind of numbers work, you either have to do lots of. I mean you have to get like vast numbers of billion to $5 billion exits. Are you in? As I say, you're playing for the 10 billion or the 100 billion exit. The question is how many of those there are. Typically, anyone who raises one of these funds has proven they can already find at least one. Andreessenhoitz. They found databricks and they've done amazingly well. They own a huge slug of that. It's not just a fund returner, it's a multi fund returner. Right. No one gets given 10 billion or $20 billion because they're idiots. They got given $20 billion because they earned it by you know, 10 or 15 years of track record with no bad funds. By the way, that back to that kind of the comment you made on other partner earlier. You demonstrate your. And then typically, most things in finance when things goes wrong is when people lean into a trend just a bit too far. And the judgment here is, is this that point? And that's really what you're asking? And I don't know. I mean, I think the biggest thing they have in their favor is the fact that so many companies are staying private for longer, which by definition means more need for capital, which by definition means if you have that capital, you should be able to make an acceptable return. So the venture market that I knew 20 years ago couldn't digest $20 billion. It wouldn't even be closed. There would be no possibility of return. Because typically IPOs were 1 billion to maybe 5 billion. And there was one bigger than that every year at most. In a world where things are staying private for 15 plus years, where there's massive secondaries to deal with employee issues, it may well be that there's a place to put all that money. The returns mightn't be 3x venture returns, but you know, the competition is the small cap return of 11%. You know, if you're delivering high mid, high teens, it may be that the LPs think that's great and that's the bet they're taking.
Unknown
Jason, how did you analyze it?
Jason Lamkin
There's some LP on Twitter that made this tweet literally this last week that I'm a little slow. Like when Rory made the old one to ten and five quarters less. This one opened my eyes too. Is like the side. These funds seem crazy and they are crazy, but the size of the fund should be tied to the amount of winners you can deploy X amount of capital into. So if you're Andreessen, VD2 and Andreessen at this point, certainly been true of Sequoia since we started, is they see every deal. Andreessen sees every deal. Okay. And so they can put this on a spreadsheet and they're like, you know, Databricks was 27 billion in 2021. What if we'd done the whole round? Forget about that. They were in the A, right? What if they just put in 3 billion in 2021? They would have already 2 1/2 x their money. They put it on a spreadsheet and they add it up and they're like, yeah, we can deploy 20 billion in 24 months. Right? I think that's the way it works. And I think it's that simple. And there's so much capital to Rory's point, especially in these later stage deals and AI deals, they can easily deploy the 20 on that spreadsheet. If you see every deal. I do think there's a sensitivity analysis and the model supports it. It that's what you want to do in venture. And when you raise too much for the fees or whatever, you run out of deals. Most folks run out of great deals to see if you see every S tier deal. Like here would be my Andreessen math if what if we see every S tier deal there is in Venture 100 we see 100% of all the best deals. 100% of the. We've seen them all and we passed on 90%. Then you could go back in time and just do an analysis, right? This is what we should have done when we passed on all the decacorns because you're in every one and it maybe solves to 20 billion. It I think it probably does. That's what they should have done.
Unknown
I would hard push back that they see every deal.
Jason Lamkin
Hard push back. But folks get fired. My limited experience is Evan Driessen, if you're not marker Ben, you get fired. If you didn't bring in every deal, don't you? Rory isn't. I mean, isn't that the way Ventura gets a deal?
Harry Stemmings
If you don't see every deal, you can stipulate they see most.
Jason Lamkin
Right?
Harry Stemmings
I don't think I Harry genuine comment. Of all the things that could go wrong with a $20 billion fund strategy, not seeing every deal. It's not a top three issue. The two issues with deploying $20 billion are first of all, yes, you see every good deal. But remember the next sentence. You see every deal, which means you see every bad deal and there are 99 shit deals for every one good deal. The more deal flow you see, the more important picking is. Now, relative picking is easier than absolute picking. In other words, if we are comparison shoppers at heart, most sometimes in the abstract when I look at the deal, I get kind of cut up and it maybe it's good, maybe it's not. But most of the time, if I see a good deal and five bad deals, my little IQ can go, I think that one's better than the other five. I should do that one. So seeing all the deals is a huge advantage, but you still have to piece through them. So that's kind of issue one. You're going to see every good deal. If you're into at round every good deal, but you're also going to see every bad deal. So picking still matters. I think they can figure that out because they're wildly smart dudes. I think the real question in the end comes is there just room as privates for all that money? And if there is, this will continue. And if there's not, then at some point it won't stop because the venture guys will be mature. It won't stop because the founders will kind of be more careful. It won't even stop because the LPs will stop. It will stop because the LPs bosses, the overall CIOs will stop allocating capital to venture. Until that happens, this game goes on. And by the way, if it happens the day after they close $20 billion, they win the best because they have 20 billion and no one else has any. So this whole little ecosystem adventure is going to keep going as long as there are enough new LPs to fund it and keep it fueled up almost clearly independent of the wider market. It's been stunning that the 2022 crash didn't cause much more than the pause for breath.
Jason Lamkin
It was just a pause for breath. It was just crazy.
Unknown
When you look at OpenAI raising $30 billion and when you look at Anthropic's multibillion dollar fundraiser, I don't think there's any question on whether this ecosystem can actually absorb it. I think the subsequent question is, is it fundamentally a venture game? I know, and we both know many investors in some of the model providers who came in at 4 billion, it's now 60 billion and they're 3 1/2x up because employee stock dilution was so heavy and the funding rounds coming in were so heavy, the multiples are shit, even with great returns.
Harry Stemmings
My observation, my own thinking is I'm sometimes too conservative, so I push against myself. I think one of the big advantages some of these newer entrants have had was that they weren't in the business a long time. Because when you've been in a long time, I remember 99 to 2002, I remember the crash after.com and all the capital getting withdrawn. So it made me naturally cautious. And you're right, the idea of writing a check at 4 billion, I did this instinctive, well, that's not really venture. But the truth is this venture will pay to make money. And some of those rounds have made decent money. Perhaps not as money as they thought because of the dilution. But I mean, if you look at one of of the common Characteristics of the folks who entered this market and have been successful has been newer entrants like Andreessen, like buyers unencumbered by quote, is it venture? And who have just said to themselves, how do I make the most amount of money and hack the system?
Unknown
And they've made Thrive, I think are a great example.
Harry Stemmings
Beth. No proof, by the way. And I'll tell you why Thrive worked. Because a real estate investor knows only one thing. Buy the best damn house on every block. So he bought the best damn house on the fintech block stripe tick. He bought the best damn house on the OpenAI block tick. And then he bought the best damn house on the infrastructure block, databricks tick. Then you just go home when you're done and you wait for the checks to roll in. It's genius. And you're right. Every little fiber of my being would have said, don't do that. That's not Venture. But I'm not living in three houses in Miami. He wins. So I've learned to say to myself, don't just say it's not Venture, just say it's a. Is that the right strategy for this game? And it clearly is the right strategy for this market at this point in time. Will it be the right strategy across the cycle when there's an equity downturn? Maybe not, because the only risk you're taking is price risk, but that's typically a correlated risk. So if it does go wrong, maybe it's only a one in three chance it will go wrong on everything because your equity values will tumble. But absent that, the Thrive strategy was brilliant. Buy the best property on every blog. It's like Monopoly. You got all the little blue ones. People are going to land in it and you're going to make a lot of money. I'm profoundly jealous of that insight. If someone had given me $5 billion, I probably hope I would have been smart enough to do that myself. The criterion is not is it venture or not venture. There's only one criteria. Is it going to make you money? And is it going to make you money across the cycle? And the answer to the first part of that question looks like it's yes. And the answer to the second part of the question across the cycle is call me in a year or 10 years.
Jason Lamkin
Why struggle to pretend you can do 8x over 20 years on a seed fund when you can just write one big check into a winner and call it a day and achieve liquidity? In a quarter of the time, the multiple will be lower, but the absolute return will be higher, the carry will be higher. Why would you do the stupid seed investing and wait 20 years so that everyone on Twitter can say you had an 8x or 10x fund, hooray. Split with four partners on your tiny little fund after 20 years making nothing, just write the big fucking check and call it a day. Like, it's so stupid. Like, when outcomes are a billion, seed is, is, is great. When outcomes are north of 200 billion, it's for cedars, for suckers, Rory. Seed is for suckers. I think.
Harry Stemmings
I love that. I just. That's. That, by the way, is about to be. I'm going to steal that. I'm not even going to give you credit. I love it. All joking aside, you're exactly right, Jason. We're saying the same thing, which is, and this was a compellingly great way to make a lot of money, provided someone was willing to give you that kind of capital for that risk. And what I don't know is there's a part of me sometimes think it's a really good risk, you should make sense to do it. And part of he thinks it's a very risky strategy in terms of correlations and if it goes wrong, it'll be horrible. It's not what we do. So I don't spend a lot of time thinking about it, but right now it looks pretty good.
Unknown
But can I just ask Ru, what could go wrong when you say about that correlated risk? They feel relatively uncorrelated to a certain risk.
Harry Stemmings
They're uncorrelated in terms of individual financial performance. Are picking anything to do with picking? You've picked the best asset in three diverse markets. You're right, they're not correlated that way. What is correlated is fundamentally equity values. We live in a world where high growth tech companies get 30, 35 pes. If hypothetically a president were to destroy the economy, like in the 70s, just saying. And PEs went to 9 or 10 or 11, and even growth stocks went to 12 or 13. Like, look what happened to Nifty50 between 68 and 82. In a world where the growth stock premium goes away, if you start valuing all those assets of six or seven times revenues, which is still pretty healthy, you're just in a very different place. So that's the only risk. You've bought the best assets. The only risk is that the world decides that equity isn't worth as much. And in that case, to be clear, a strategy that would get a 3x will get a 1 1/2x because you haven't taken a ton of valuation risk. If you're doing the kind of things we do, a strategy that's entirely predicated on buying marquee assets at high prices could get a 0.5 or 0.7x.
Unknown
And so what you are there is time sensitive because you don't want to have to liquidate in a time where you have that compressional multiple. Which is why if you have 20 billion, ka ching, I can pay that price, buy the best house on the block, and if I want to sell that house and there's a market crash, kaboom, I can put in even more money at a reduced price and wait for the multiples to expand again.
Harry Stemmings
Again with this one implicit. Broadly, yes. But there's one implicit assumption in that, which is that the company will continue to compound. And the problem here we're dealing with is ex post facto vision. There are five or six technology companies worth a trillion dollars, so it's clearly doable. You can clearly compound from 300 billion, which is where OpenAI is today, to a trillion because five other companies did it. What you forget is most tech companies don't. And every time you hold for longer, think of it as a process of distillation. Your best ones get better and your worst ones go down. So provided you've got the right ones, you can tough it out forever. But be a bit of a bummer to discover you'd invested in BlackBerry and it was still private, and they just launched the iPhone and you decide, screw it, we can take these guys, I'll put in another billion, and then you just march the thing down. The hard truth is, most tech companies in the end get acquired, rolled up, unsuccessful. So the longer you push, the more premium there is on being absolutely right on your stock picking and having the winner. Not a crazy bet. I'm just saying, typically any financial bet has an embedded risk somewhere in it. There's no such thing as free money. And when stuff looks like there's free money, it just typically means that the risk isn't fully recognized. This has been a great business, this ultra late stage. I mean, you send a tweet, Jason, I saw it there about that. It looks like the easiest way to make money imaginable, which makes you go, a, I wish I'd do that, but then B, what's the buried risk?
Jason Lamkin
And here I don't want to discuss the company. Okay, don't push. You can push me on anything except this one thing, but I just have a company that's just become a unicorn. A late Stage Fund just put in almost nine figures. Okay. And they own as much as me. Now, listen, I'm lucky to be a part of the company, but like, Like. Okay, listen, if the company's only sold for the basis, they make nothing, right? But they're underwriting a $10 billion outcome, right? They, for all intents and purposes, will make just as much money as me, right? In fact, they can support the company more. They skipped years of work and stress, and it has to be a big outcome. But if it does, why would you do this seed stuff? Like, it's the same ownership but skip all the years, right? And yeah, if it, you know, and you've got your what if X, worst case, your wonderful one X.
Harry Stemmings
But there is an. I'm going to argue against. I understand it because I go to the same, you know, angst and machinations, right? Good deals in my portfolio where we've made good money and where later stage investors haven't. And that's just the nature and number.
Jason Lamkin
But if it's really good money, you make the same.
Harry Stemmings
Yes, agreed.
Jason Lamkin
If this is an outlier game, right. Who cares about those little $800 million outcomes? Who cares?
Unknown
Rory, can you talk about one way you've made money, others haven't, and just what you learn, you don't have to name it, but just to put it.
Harry Stemmings
The higher the price you pay going in, the higher the price, you have to be on the edge to make money. It's just as simple as that, because we went on both sides of that. We had a sale recently where we got a 1X and the early investors got a 3X, right? And it all comes back to this idea of it can go back to even the access to capital. If you have access to capital that's large and forgiving, which is what these mega funds have, then you should play the big balls game, because you're exactly right. You have to do less work. If it works great, you make out the same as Jason, who did the C for suckers, and Rory, who did the A. And if it doesn't work out, you're gonna get a 1x, but you get forgiven and you start again. If you have access to that kind of money, that's the game you should play. Remind me. The reason you and I don't play a different game is I was wandering around in 2009, and no one offered me a billion dollars and said, hey, have a go, and if it doesn't work, we'll give you another billion in 2030. When you have a smaller Fund, you want to have a higher probability of the upside. And logically, even though you don't want to hear this, the higher your going in price is, just the less likely it is you're in that one deal that can transcend price and be the. Not the billion dollar outcome, but the $10 billion outcome. You're just upping the bar on getting it just right. So that's the argument for it is that 5 billion and I could get 20 billion. I played, but Mark and Jason was still.
Unknown
I get that, Rory, but you have a pretty great track. You've proven yourself to be a phenomenal investor across cycles. With respect, you could probably get a lot more. Now, why do you not?
Harry Stemmings
I think actually we're all products of our experience. I think I'm a very conservative invest, somewhat conservative investor. I think I am branded a little bit by remembering surviving 99 to 2010. I don't want to take a lot of money at the end of my career, manage it badly and then fail. I don't want to make that bet because I've seen what it looks like when it goes wrong. I remember what 99 to 2005 was like and it was miserable. And it's kind of you to say about my track record, I'd say it's solidly good rather than spectacularly amazing. Right. I'm a solid, good investor. And I would say this. I am most proud of the fact that I made small amounts of money from 2000 to 2010 than I am about much larger returns from 2010 on. I've lived through a downturn and survived when 70% of the people I knew in 99, 2000 were out of the business four years later. So probably the way we run our business, the way run our investing strategies, I always wanted to survive that downturn. And that probably constrains your upside a little bit, but it increases the probability of not going horribly. I mean, I remember how horribly wrong things can go. I mean, the big moment. The two biggest momentum players of the last decade, Tiger and SoftBank, already out of the game. Huge credit to someone like Insight who were putting out a lot of money but managed to survive because of savvy. But the bigger the dollars you're playing with, the more risk there is at just getting crunched when the tide goes out.
Unknown
What did Insight do to survive more than Tiger?
Harry Stemmings
I think they had a much broader. They were doing deals at much earlier, lower prices. I named them only because logically, if you just rank the dollars raised, they were third on the list. And you know, South Bend, gone, Tiger effectively gone. I think they were just better investors. I think they had Teddy.
Jason Lamkin
Doing a few whizzes is going to help, isn't it Harry?
Harry Stemmings
Absolutely. That's my point.
Jason Lamkin
David Savage, he didn't even do the last round.
Unknown
I mean, yes and no. Jason, if you actually looked at the returns, I mean, yes, 100% amazing, but it was a $2.6 billion reported return to them in an eight and a half billion dollar fund.
Jason Lamkin
Which is like math still is hard. Yeah. I mean, Teddy did one of the best investments of all time and it returns a third of the funds. A third of the fund. That would drive me nuts. I would probably quit Venture if I did Wiz and it was only a third of the fund. I would probably tell him to go talk to Harry and Rory.
Harry Stemmings
If you are pulling down the fees on an $8 billion fund, I don't think it quit cynical.
Jason Lamkin
I might quit because the game wouldn't be fun enough. The game wouldn't be fun enough. Right.
Harry Stemmings
But I do think the bigger you are, but genuine comment on that, the whole 2.6 billion only returns about the bigger you are, the more you undertaking to be competent and find not just one of those, but multiple those. It's the same point over and over again. You've embarked on a strategy that only works if you have a really strong level of execution and you get in large significant numbers of the very best deals. And you know, all credit to Insight look like they've done that. And without paying over the odds, less credit to Vision Fund than Tiger. They kind of, kind of went over the top of the curve and just kept going a little too long like, you know, Roadblock, your degrees of freedom and you know, Andreessen will wrestle with the same thing. I think they're wildly savvy investors. But when you've got 20 billion, the impetus on being disciplined. Just degrees of freedom you have are.
Jason Lamkin
Tight for the old school. Like Emergence just raised a billion. Okay. They were one of my investors. I didn't ask them, but I think I know. I think there's probably two reasons they raised a billion, right. One is because there's a new generation, right. Who's maybe less risk doesn't have those scars. But I think the second reason is the checks are bigger. Emergence just did like 50 billion or 60 million into like Bolt or something like that right. Back in the day. That'd be a $15 million check. So what about funds like you having to have a fun size to play the game?
Harry Stemmings
Today I agree, because yeah, I know and respect those guys enormously. And you know, we've done roughly the same thing. We put probably over five or six fund. You've gone from 300 to 600 and 900. And then the fund hasn't changed all that much because the average check size has gone up. And let's talk about that for a second. I just checked it. Nominal GDP growth, in other words, the paper value of money, it's 3x from 99. In other words, GDP in 99 was 10 trillion and it's 30 trillion today. So in other words, if your fund size was 100 in 99, you got to be 3, 400 today just to be the same thing. And in particular, in the last four or five years, nominal GDP growth in the COVID period has been huge. If you're not up 50%, you're falling behind. Some element of fund expansion is almost inevitable because the check size has gone up and the check size has gone up appropriately. And then on top of that, there's probably some extra increase in the check size that maybe isn't appropriate, might not be the right word. But it's less driven by pure economic, the economics of just inflation and more driven by people are playing to win. And what you see in that is if you don't grow. We wrestle with this. If you don't grow the fund size. We were finding deals that we would have thought were the scale sweet spot, we just weren't relevant. You'd come into a deal with your little $20 million check and they'd laugh at you and you'd go up to 25 and you'd call an LP and they'd get 5 and then you'd be up to 30 million. And you've got to size the fund for the strategy, because fund size is the strategy. And I think for the kind of a B stage where those guys play, we pay. You probably are writing $20 million initial checks, you're probably writing $30 million total checks, including reserves, without even hogging for those late stage rounds. And you probably want more than 20 deals per fund because as we discussed half an hour ago with product market fit variants to replicate the same overall fund return. And this is where I do disagree. The podcast of a benchcock. I want to make sure I have enough deals in every fund that the fund has a good probability in success. Say you're closer to 25 deals per fund. You're at 7, 800 before you blink.
Unknown
But this is why $50 million seed funds drive me Nuts. Because actually when you take away fees, you got 40 of investable. And when you think about the average seed round today being three to five million dollars, if you want to lead it and take real ownership like they say they do, there's no way that you're getting at least even 20 companies.
Jason Lamkin
You're not. You're taking concentration. That's what I always do. Concentration risk.
Rory O'Driscoll
Yeah, but pre seed or seed, I.
Unknown
Mean, Jason, this is nuts.
Jason Lamkin
Well, if you don't want to, if you want to play that game and you don't want to raise a massive fund, you got to take concentration risk. Right. Or pretend.
Unknown
So. So founders fundraise $4.6 billion $1.6 billion over supply I have so many LPs. Call me asking which funds I like. Which reference. Well, from the show, I've never had such institutional demand for any single fund asset than I have for Founders Fund. Every single LP wanted Founders Fund and wanted Founders Fund gross, which is even more rare. Will we have more and more money go into the asset class? Will we have more and more money concentrate into just the top players and it'll be shit for everyone else. How do we think about that?
Harry Stemmings
I'm trying to relate the facts to the question because it wasn't obvious how you got to the question from the facts, because the correct response to the facts you outlined about Founders is they may be to a rounding era, the best fund. So no surprise they get the most demand. I mean, it was great to see the leak. Now, they're astonishingly good. I mean, I don't like this conclusion, but I've realized that my Bayesian prior on financial matters and ventures should be checking in what Peter Thiel does, because he's been right on a lot of things they've played. I mean, they have a very clever high IQ strategy that they've made work and you can see it in what they've done and how they've done it. We can come back to that in a second. Right. So it's kind of like we're all playing this game and they're just playing it really, really well and cleverly. So they should get the most money. You should. Just because you give the money to the smart guy doesn't mean from an LP perspective that you should do it to 10 other people. You could argue. I mean, that's why I said I couldn't connect the facts to the question. You could argue that this is an idiosyncratically brilliant performed track record because it obviously leaked. And what you saw is exactly what they advertised, which is long holding periods, strong IRRs, though not amazingly stupidly stellar, but holding periods of 10, 15 years. Right? They bought SpaceX, I think in 0708. So they have compounding after and it turns out if you compound a 30, 40% growth not for eight years, but for 15 years because you don't give a damn about giving the LPs money back early, you're just going to compound the thing to make money. Then you end up with an 810X fund. They did exactly what they said they'd do. But two things they did. They held for long periods of time in highly differentiated companies. And then the second thing they did was to an earlier point, they were absolutely willing to take on massive concentration in their winners. Again armed by the one fact that you can't overcome. They didn't have to give a damn about anyone being afraid of the risk because their perspective was if you don't like the risk, take your money and go home. They were able to push. So you take those two facts and add to the fact that they're very good pickers, you have the best the order, right? It's the best. It's a money making machine and devil to the best.
Unknown
Brian Singerman said to me in a show once, the enemy of great venture returns is capital concentration limits. On a per fund basis, we have 30% of a fund in certain assets. We know what great companies look like.
Harry Stemmings
Yes, and it is the end. And he's exactly right. But now again, to take both sides of that, it is the enemy of greatness and it is the protector of massive wipeouts. And it just boils down to the personal choice of where in that dimension you want to be. I think for example, I mean Brian, I've heard him speak once, I thought, very articulate, very clear strategy. They had that big win. They had the stones to put 300 million in a biotech company. I can't remember the name, but I should do stem centrics. Stem centrics, exactly right. Got a 5X, took money off the table. Worth pointing out, three years later, the acquirer canceled the program. Huge amount of risk made it work. But never forget the risk was there. But those guys, they built a product that said we're comfortable with the risk because we like risk and we think we're smart enough to underwrite risk. And they were. It's a very high iq, high conviction strategy. And I think an LP saying I'll do Founders Fund because they got these returns and 10 other funds they'll be just like Founders Fund. That sentence doesn't make sense. They won't be just like Founders Funds because they're not the same people with the same approach.
Unknown
You're right, But I have two LPs a week managing between 350 and 500 who come into our offices in London and say, Harry, you. I've got all the data from the shows. Walk me through how I should do this. I've got 100 million going into Index, Excel, Founders Fund, Sequoia 25 each. And now I've got. Let's take the low end of the budget. 350, 100 going to the best assets like your Founders funds. We said there. Now I've got 250 left. Where do I put that as my annual budget for Venture? Harry, I need to spend that as go to light speed. Let's go to gc. Let's go to red grab point. Let's go to.
Harry Stemmings
It's an interesting point. You have to accept the fact that you probably are going to do deals. It's going to sound really obvious when I say it, but it matters. That won't be as good as the best deal you do, but they still can pass your IRR threshold. At the end of the day, let's assume there's a force ranking and let's agree for arbitrary sex that we put founders and I don't know, I haven't seen the number so I can't comment on Sequoia but based on observed data at scale. In other words not including seed funds but in terms of turning industrial quantity of money into 8 and 9xs, let's put family Fund at the top. You put what you can in there and then you got two choices. You can stop and go home. But the problem is any money not allocated to that has to go in small cap public companies and gets 11%. Or you can decide on what you know. You just have to pick a portfolio folks and go down, you know, and hope that they all perform as well. But you're just looking at. You build a portfolio of companies whose strategy says not that they can replicate the best number but that they can comfortably outperform the public markets with a strategy that's repeatable and differentiable and many of the names that you just saw have that.
Jason Lamkin
Can I ask one question about Founders Fund? Not to interrupt Harry, but before we go on, just because the start of this conversation, what do you think about Rory and Harry? What do you think about the fact that Founders fund doesn't do B2B intentionally, they make exceptions, but they don't believe in B2B. They don't believe the outcomes justify it. It's explicitly they don't do it.
Harry Stemmings
I think I have to make makes the point, which is there's a lot of different ways to make money. It's the intellectual conviction of wanting singularity deals. It's wanting deals that are n of one where there's typically a high technological component to winning. But then once you kind of have that done, you have low competition, you get the prize. It's a totally realistic way of playing the game. The interesting thing is there's not as many of those deals. This actually goes back to the point conversely, B2B, they are right, which is that very few companies in B2 have the same level of untrammeled competitive free space that something like SpaceX does. That's the negative on B2B. But the positive on B2B is there's been two to 300 SaaS winners and there's a lot of different ways to make money in B2B. So it's a different strategy. I mean, I'm sitting here going, would I prefer to have put 20 million bucks in SpaceX gone home and compounded to 360 million? Yeah, of course, that's one way to make money. But I'm pretty damn happy about the way we chose to make money in a whole bunch of B2B software companies, each one of which doesn't have the same investment multiple as you might get on a SpaceX 10 year return, but nonetheless provides a very attractive adjusted risk return profile for the way what I admire them for the way they look at the world. They've basically said we are smart enough to look at a whole series of wholly different markets and have the raw IQ to recognize greatness in biotech, space, et cetera. That's all. And we can do that. We can see those deals and we can pick them. Whereas conversely, you know, by focusing on B2B little or less, we're saying we're just going to focus in this space. We're going to try and see all the deals. The competitive set in each one won't be as compelling in terms of white space as doing rockets. But there's going to be a lot of winners. We can pick by market. We can have a nuanced way of picking the winners and make it work. It's a different gig. Good luck to them. They're amazing.
Unknown
I would also just say two companies that they are most excited by are Ripley. Yes, and Ramp that's true.
Jason Lamkin
Well, I, but I don't think Harry, my limited. Because, because I talked with, you know, Sam Blonde was, was at Founders Fund for a while. Right. A good friend. They told him they don't do B2B investing. Then that viewed Ramp as a fintech. That's how they think. Now listen, you. I, I just thought it was. You can, you can do it. But I'm saying from the inside, this is not a criticism. I found it eye opening and rippling's good, but they did that deal with Sam. It's only so large and it's the same. It's, it's, it's, it's minor. Right. I think, I think even if those, if one's a fintech and one's an exception, it doesn't mean the point isn't true. That they don't generally do B2B. It just doesn't work for their model. Right.
Harry Stemmings
I think kind of the refined verse from that statement is, look, we're not going to industry focus and do 50B 2B software companies like you're doing Rory or you're doing Jason. We don't believe that's the way the greatest. We're going to do everything. And if some percentage of them, 3, 5, 10 turn out to be B2B, that's fine. But we didn't back into it with a thematic market focus. We backed into it saying, I only want to do greatness, amazing greatness. If I run into a B2B guy who has amazing greatness, I'll do it.
Jason Lamkin
If I don't, oh, well. You think the fact it's like a 50% capital commit and run by rich people informs that too?
Harry Stemmings
I certainly hope so because I have.
Jason Lamkin
A pretty large capital equipment myself. But it's like if I had that much, I wouldn't want to be going for triples either. I'd be wanting to hold for 20 years because I'm plenty rich and I'm certainly not in it for the fees. If I have. If my capital commit like exceeds anything in the fund.
Harry Stemmings
No, I mean, it's exactly what they should be doing. I mean, as I said, I think it's an. What I admire most about it is that the practical steps they're taking are in sync with a stated strategy, which is ambitious, hard to do, and nonetheless, they've been able to do it. Go ting.
Unknown
Will we have more or less LP money going into venture in the next three to five years? There's a lot of macro uncertainty. We have endowment funds facing large fines More uncertainty there. We've got the denominator effect impacting their public books. But then venture is powered by AI again, and now's the best time ever. Will there be more money going in or less over the next three to five years?
Harry Stemmings
My gut would say at some point you see less. It boils down to this private for longer class. The thing is, there's an optimum amount of money relative to the opportunity set. The tricky thing is this. There's an optimum amount of money relative to the opportunity set. The opportunity set has massively expanded because of its whole stay private for longer, which consume vast amounts of capital in the labor stage. So it makes sense that the amount of money going in has also expanded. So you look at that and you can really make a modest an optimistic scenario that says the capital has only expanded proportionate to the opportunity. But on the other hand, the cynic in me says in financial markets things tend to overshoot, especially when the indicators of success are lagging and venture is the most lagging market. So what's probably, in my view going to happen is LPs are going to steer on the trailing 10 year returns and overshoot on capital in. And then at some point those returns will go the other way and then it'll take a while for the shoe to drop up and then they'll start withdrawing capital, probably just at the point when they should be investing. So if I was to guess, sometime in the next five years you'll see a significant change in availability of capital. Like I remember in 2010, people saying, literally, well, let's help people with this. It will not be a great time to invest in venture until people spit at you when you mention the word. And in 2009, 10, they were like, lily, get out of my office. None of you have done anything for me for 10 years. The last good fund you have is a 96. Why the hell would I even do venture? And it turns out that was the time you should have done nothing but venture. So if that's true, and it is, the inverse is probably true. When it's obvious to do venture, when everyone wants to do venture, it's probably a tough time to do venture. When does that turn back? Hard to tell. But intuitively, at some point I think it will overshoot and then start to pivot back and it'll be a better time to invest and a tougher time to raise.
Jason Lamkin
Rory, let me ask you this heuristic. If you take a window of time and maybe elongate it to seven years, okay? The amount of exits and IPOs and M& A. Roughly speaking, all the exits should be how much venture comes in. Right. New venture comes in roughly. Right, Roughly. So, I mean, I think LPs are pretty. I mean, they get scared and smart. But if those exits keep going, it should happen, right?
Harry Stemmings
If.
Jason Lamkin
But it's. It's been a while for IPOs. It's been. It's been a hot minute for IPOs.
Harry Stemmings
Right.
Jason Lamkin
Maybe the window's seven years. I don't know how long it is.
Harry Stemmings
Yes. I mean, I think at some point the money has to come back. Because in general, my observation is people don't stop doing stupid shit because they intellectually figure out they stop doing stupid shit. They generally stop doing stupid shit when there's no more money to do stupid shit. And the answer is, if the money doesn't come back, then eventually the money won't be given to us. And that's simplistic. There's a famous Ben Stein quote. If something in economics, if something can't go on forever, it will stop. Stop. Famous quote from then. But I think the corollary is also true. Until idiocy has to stop, it will go on. So the real question is, does a stripe a Databricks, an OpenAI IPO, does the cavalry come back quickly enough to keep the money flowing at roughly the same level, which would be an indicator that probably the amount of money in the system was roughly about right. I mean, individual funds might do better or worse, but the system was about right. If, on the other hand, if those key keep pushing out, then at some point it becomes really hard to have all this money in private, illiquid assets when you have pressures on your endowment and all that. And then at that point you would see the money go down.
Unknown
So on that, you know, we've seen, you know, your Klarna, which was going to go out, push back. You've seen several others push back in the wake of macro uncertainty. StubHub, you've seen, you know, stripe, stripe, don't want to go out for a long time, Rory, you know, if, you know the Collisons, they're like, why would I do that?
Harry Stemmings
I don't need.
Unknown
They said on a show recently, why do I need some analyst at a bank to tell me about my margins?
Harry Stemmings
Agreed. And if you step back from that, first of all, they're correct. And it's a massive public policy failure. Because what's happened here is this. It is more attractive for companies to stay private and access capital from GPs who are paid 2 and 20 plus to make those investments than it is for those same companies to go public and access capital from Fidelity Growth fund where Fidelity only gets paid 70bps to make the same investment. If you think about it, we have defaulted to the higher priced capital alternative, which is absurd. So you have to say to yourself, why has that happened? Because remember one of the rules is the company doesn't care if it's public or private. Stripe is going to be an amazing company. All other things been equal, public or private. So the only thing that's changed is instead of it being public and compounding nicely, and as I say, getting funded by low cost public mutual funds, it's private and getting funded by high cost venture funds, that's a weird outcome. Why is it? And you have to say to yourself, why does it happen?
Unknown
Well, you would also say that it's not high cost venture funds in a lot of the latest rounds. These are very, very large pension funds.
Harry Stemmings
Actually, you agree with me, not disagreeing. I didn't say high cost to the investors investor. It's the other way around. It's not high cost to the company. And you're exactly right. That's one of the key points to the investor. If I was a pension fund In New York 20 years ago, I gave my money to Fidelity Growth and I got stripe at 70bps. Now I have to give my money to thrive and get stripe at 2 and 20. That's why I said it's a public policy failure. The ordinary investors of America are either not getting the good assets or getting the good assets at massively higher fees. And if you believe, as we said a few minutes ago, that the performance of Stripe is not impacted by whether it's public or private, what it means is the return to the investors is instead of say stripe's compounding at 15%, if I owned an infidelity growth as an investor, I got a 50% gross return, 70bps, 14.3 net IOR. If I owned the same asset in privately held VentureCo, 15% gross, 10% net after fees and carry. So my return as an investor, an ordinary saving American who's trying to put money aside for their future, has been reduced massively because all these companies are staying private instead of being public. And that's a monstrously stupid outcome. So why is it happening? That's the question. And I think it's a combination of things. I think the public is a pain in the ass, which is something you need to fix. And I think being private is cheap and easy. Money, which my gut is if something would eventually be fixed, those two things together have to change for it to be rational for late stage big private companies to want to go public.
Unknown
I was with one of the most successful founders of our time the other day and he said literally, there is no really significant reason for any great company to go public today. For the not so great, but still very good. Yes, but if you can raise endless money at great prices with private investors with no scrutiny.
Harry Stemmings
Agree. And that sentence is why it will eventually stop. It only stops. Go back to the thing is that those poor investors, they have two choices. They can. There's public companies where they can get 15% growth, 14.7 net, or there's private companies where they can get 15% gross, 10% net. At some point they will reallocate capital away from those private investors to those public investors. And then what will happen is private companies will not be able to access effectively free capital. It's absurd that the free capital is at a higher cost in terms of total cost to produce the capital. Right? It's absurd that it is cheaper to get money as a private company from a provider who has a 500 basis points cost structure than to get money from a public company, public mutual fund that has a 70bps cost structure. It's like intellectually madness. But it's where we are now and they're correct until that stops. And intuitively when you say it like that, you say to yourself, at some point what logically will happen is the late stage private investments will underperform equivalent public investments by the amount of the fees and then it'll switch.
Jason Lamkin
I guess that's the. That'd be the efficient market thesis, right?
Unknown
Can I throw one out there? We've said about the enormous funding rounds, super intelligence, $32 billion, $2 billion in supposedly no product. What did we think? I have some thoughts. I'm intrigued.
Harry Stemmings
I think, Go team. I think, look, go. I think that the argument in favor. I think there's compelling arguments in favor. OpenAI invented all this. And as an investor you can say to yourself, I either do OpenAI or I can do one of six or seven other foundation model companies. If you fast forward three years, all the foundation model companies that weren't populated by people who were at OpenAI haven't done great. And anthropic that was populated by people that came from OpenAI has done pretty well. So what it says to me is they crack the magic code in OpenAI. They have the secret recipe fund people who have the Secret recipe. And it works fund anyone else and you kind of get a me too outcome. In retrospect, that was the logic for doing anthropic. They have the secret recipe. They snuck away from the Magic Kingdom with the secret recipe back there. Don't back all these other dudes who are trying to figure it out. Using the same logic you got the guy who invented the secret recipe. Why not? At least you know he'll probably crack it. So your risk level not being able to figure it out is pretty low. And remember, the risk level for people who didn't have the secret recipe I'm not figuring out, with the exception of Grok, which is astonishing, is quite high. So it makes sense because you can buy something that can crack the code. Now, what that model is worth once the code's been cracked is a totally separate discussion. I don't have an insight on that, but I totally get why they're making the player.
Unknown
I cannot see why one would not do this deal. I think this is. People looked at this and went what? Nuts? Nuts. With a liqpref, there is zero chance this does not get bought for at least liqpref. It's fucking Ilya. Microsoft will buy him for 10 billion.
Harry Stemmings
Tomorrow, provided the government lets them buy him. But yes, agreed. No, you're exactly. Look, look. More marginal foundation model outcomes have yielded returns beyond a 1x with exactly that mechanism. So yes, that's you odds. You're exactly right, Rory.
Jason Lamkin
Can we really count on the liquidation preference in these types of deals? Can we really count that it's going to be honored or we're going to get our money back? Is that really the real comment?
Harry Stemmings
And you're quite correct. It's always stunning when you get down into the arcania of Delaware low. And what can actually happen the day of a transaction if someone decided to actively not honor the press, there's a bunch of ways you can do it. So yes, I hear you. That's the risk.
Jason Lamkin
Or if you acquihire most of the team for 10 billion and you leave the liquidation preference over into C Corp, doesn't that work?
Harry Stemmings
Yes, that works too.
Jason Lamkin
It's just. Listen, my limited visibility recently in M and A is that every acquirer is looking for ways to get around all the BC preference stacks. It's aggressive. Like it was always true, but now it's like super aggressive. It's like we just don't even give a rat's ass in corp dev how the certificate of incorporation structure what the documents say we'll do side Deals, back deals. We just want nothing going to the VC in bigger in nine figure deals. Right. So why would you honor this liquidation preference when I want that going to the engineers, why would I want it going to the VCs? And why does Ilya even care about them? I think founders care less about their VCs today day than they used to. I think they care less.
Harry Stemmings
I would love to have been in the room on some of these marginal sales where Google did one, Amazon did one, where in fact they did take care of the VCs to some extent and do the founders. Because you're right, Jason, I'm not going to comment on those in smaller deals that we're in both when we're a seller and when we're a buyer. You're exactly right. Anyone buying the company says, especially if it's a business where you want the customers, you pay down the cap table because you want the whole damn thing. If it's an acqui hire, every dollar you give to the venture guys is wasted. So you're exactly right. You do small headline deal and then large earnout contracts and you sit there and I can pretend that I'm appalled by it, but perfectly honestly, when I'm on the other side of the table and my late stage companies are trying to buy early stage companies, I do exactly the same thing. I don't give a shit about Jason and his bloody preference. I want to hire those five great engineers. Let's just give him a contract.
Unknown
The question respectfully, is that not a bit short sighted? Maybe I have a grudge, but if you did that to me, I'd be pretty pissed off and I wouldn't be that willing to give you my next card.
Jason Lamkin
Come on, it happens every day.
Harry Stemmings
I think if I'm a corporate acquirer, let's leave these big deals out. If I'm a corporate acquirer and I come up against Rory and Jason, this time I don't sit there thinking I'm gonna come up against them next time. I push as hard as I can. And if I don't push totally, brutally, it's not because I'm worried about a multi period game. It's just like at some point I'm just not paid enough as the VP Corporate Development to waste enough time and take the litigation risk of fuck over Ori and Jason. It's just easier to give him that 30 million bucks and call it a day. Now, as Jason points out, when it's $2 billion, who knows? But it's so far the observed fact is Even in these transactions, investors have made money in a sideways sale and have been able to rely on their preference. Whether this happens in the future, I can't speak to. I don't know. But that's all you know. And in the meantime, you're getting an at bat with the guy who figured it out and made the magic recipe at OpenAI. So that's what they're doing again. One of the things that every one of these discussions today have in common is in almost every item we're realizing we're all taking a lot more risk than 10 or 15 years ago. We're all playing a high stakes game. I mean it can be the price high stakes game, it can be the pre money 2 billion round high stakes game, it can be the concentrate the fund in smaller number of investments. But the one thing all this stuff has in common is we're way out there on the blue, on the yield curve, on the risk curve, except for.
Unknown
One thing, which is we're seeing this increased trend again of founders taking secondaries more and more early in the journey. I saw a tweet yesterday where it was like, hey, you know, founder secondaries at a again is completely the new norm. Are you finding founder secondaries at a really back and back in Vogue 1 and have we just shifted risk to founders taking money off the table earlier which may or may not be a good thing?
Jason Lamkin
Well, I can tell you what I've seen for what it's worth, but in all my hotter companies, the last whatever months I've seen the later stage investors put everything into the term sheet possible to win. There's no more waiting for rev the maximum, secondary the maximum, refresh the maximum even crammed down the prior investors because they don't care. They just don't care as long as the founders get their post money, their equity and their secondary. So what I'm seeing is straight out of the gate, all the boxes you can check in hot rounds, they're all checked like there's no more games, there's no more is it too much secondary don't care. Is it too much just don't just I just want to win the deal so I'm not gonna and someone else is gonna do it. So I see it all like every box checked in the term sheet today in the hot deals, every box check to the maximum. To the maximum. I haven't seen it in A's, I've only seen so many A's. But after that, everybody, everybody, every win, every deal just I just want to win it don't care. Like, I want you to be capital efficient. I want you to be, be stingy. But here's an extra 100 million and 30 million of secondary and extra stock. But, but I, but I like capital efficient companies. But I got to win the deal, right? All that, you just got to do it to make these big money in growth, you got to win it, right?
Harry Stemmings
Yes, because there's only one thing worse than this. I can go both ways on the secondary. I really don't like the. Here's a secondary for 5% of your position and here is a pre approved increase to your equity ownership for seven.
Jason Lamkin
That's the play in the growth today. Sell five will give you seven. That way it's not even a dividend. You come out ahead. Right, well, dividend might be better because you don't have to sell. Right. The refresher always exceeds the sale.
Harry Stemmings
I'm going to be sympathetic to the investor now. I've lost the deal through not doing that because again, it sticks back to my comment. I tend to be perhaps stuck in the mud on history. I think that's just nauseating because you're effectively replacing the comp committee of the company you're investing in. But you're right, Jason, you see it especially in later stage rounds, not at the A, but at latest. And you're like, if you're going to lose the deal, bad money drives out good and bad. Bad habits drive out good habits. And you know, if you got to win the deal, maybe you do it.
Jason Lamkin
I mean, I've had two deals that were done in one day, like hot deals. And how do you get a deal done in one day? Right. How do you guarantee you win? You check all the boxes. If you check so many boxes, there's even an argument the valuation doesn't even matter. Right. At some level, because you've made, you've checked all the other.
Unknown
This is what worries me so much though, with growth funds today is they assume that the outcomes are equiprobable in size. And what I mean by that is they're going, okay, I know X company is great and only worth 2 billion, but if I pay 3 billion and I put in 200 million, I know it's a 10 billion company, so I'll get a little bit of a compression on my outcome size in terms of multiple, but it's a 10 billion. What they don't understand is that if I stuff Rory with 200 million before Rory's ready for 200 million, that 10 billion outcome size will be a 4 billion brilliant outcome size.
Harry Stemmings
I want to point out that I'm always ready for you to stuff me with $200 million. Dude. There'll be no ambiguity around that store. But. But yes.
Unknown
No, I want to kind of throw out one final one before. Before we wrap. But one that is. Is we said there about like, hey, play the long game, you know, maybe being nice. Something that is just getting kind of more and more Hollywood movie popcorn, salivating his dip deal and rippling Jason me and you were messaging about it last night like, hey, is this just gonna turn into a shit show? What happens from here? Can you be nice and win?
Harry Stemmings
There's a big gap between being nice and committing what is at least some level of civil. Having some civil issues and potentially, I don't know, criminal issues. Right. You know, you can be pretty driven without actually planting spies. And if implanting those spies, you actually steal secrets, I'm winging it without. You know, my wife was a criminal lawyer, so she hit me on the head for practicing law without a license. But there is a point at which this is kind of industrial espionage. And you get caught and you get criminal proceedings. And no CEO and no company can provide that. So I think it is possible to go too far. You can be aggressive, you can be driven. And I'm not talking about the facts of the specific case, A, because I have to use the word allege and I don't know. B, I have a company broadly in the same space, so I'm not unbiased. Papaya. But if what's alleged is true, it's very troubling. And you would be struggling as a board member to figure out what to do. But even more importantly than that, as a customer of this company, if you're relying on them to manage your payroll, to move money on your behalf, you possibly can provide them having some kind of civil liability. But if it trends over into criminal liability, you probably have to find a new payroll provider. So I think that was way beyond the norm. If. As if the allegations are true, which obviously I can't speak to, but widely entertaining complaint.
Jason Lamkin
The growth rounds we discussed are part of it in general because they encourage. There are fewer and fewer boundaries in these massive growth rounds with no diligence and all the tertiary and quaternary and secondary yuan and all the deals at 8 billion and 10 million, 12 billion. There's no boundaries. You don't ever have to go public. Harry and Rory, it's cool. Take our money in whatever terms you want. Just get us our target. And anything goes. And I. Whatever exactly happened here. I mean some of the stuff's hard to argue with. Okay, clearly this guy went into the toilet and flushed his. That was paid that. We can't argue with that. Like, we can't argue. It's like, okay, but I think it's $105,000 a month.
Unknown
You can't. That's because intern for $5,000 a month these days.
Jason Lamkin
I know, but I think you're going to hear 100 just like fraud like every day. Now we pull up the media and there's another founder that stole 30 million from the investors and we shrug it off. Right? There's going to be a hundred of these in this, in this environment, right?
Harry Stemmings
We get revealed when the tide goes out. Galbraid, John Kenneth Galbraith, he wrote the Great Crash. It's just a great small book about financial euphoria and it's worth rereading every couple of years. But one of the things he has is this concept of the bezel, which is at every point in time there is an amount of embezzlement that's taken place. And you know, in a boom time the bezel just increases because nobody knows. And the minute the tide goes out, all this shit comes to the surface. And I think you're exactly right in this kid. Typically in a boom time you see erosion of quote unquote good behavior, erosion of standards, erosion of do a care and due diligence. Then things turned bad and then everyone start focusing real fast. Everyone looks at the numbers real fast. And it's interesting, you had one other thing in your pre show prep. You made a comment on ARR vs GAAP. I mean we've started really focusing on gap revenue now because ARR is a made up number and gap numbers are fact. And when the tide goes out, there'll be a whole bunch of this kind of stuff surfacing and people go, hmm, missed that.
Unknown
Sorry. For anyone that doesn't know why is ARR not so important and GAAP is more important important.
Harry Stemmings
ARR is a really good leading indicator and I used to lean on it because it's better than gap because it's a forward looking metric. But the beauty of gap is there are rules on how it's produced. If you break them, you've lied and you know there's no ambiguity around it. Was ARR, is it experimental? Is it actual? It's just more loosey goosey. It's as I say, you're trading a better forward looking metric with more ARR has More signal about the future, but more variance about the correctness. AR GAAP is a trailing indicator, but it's pretty damn accurate. Usually in today's market where there's a lot of experimental ARR leaning into that ARR, it gets back to where we started this conversation. Leaning into that ARR and thinking that's repeatable, scalable, therefore ever ARR like a SaaS multi year contract from Salesforce. It's just not the same thing.
Jason Lamkin
Yeah, most of the AI, the R, the R aren't real. It's not really annual. It doesn't really recur. What's the third one?
Harry Stemmings
Revenue.
Unknown
Yeah, yeah.
Jason Lamkin
It may or may not be revenue. Definitely doesn't recur. No way it's annual if everyone can get out after a month or two. So it's neither A nor R nor R. Can I share one number just for fun? Before I was just pulling up a Saster survey. Going back to real and dippling. Real and dipping.
Unknown
Yeah.
Jason Lamkin
I asked 2,000 folks in Saster how many folks lie in deals to win deals? 93% said they lied over 2000 to win deals. If 93% of 2000 B2B folks are lying to win deals. Lying about features lined out feature gaps. Okay. And you've just been handed billions, how much would you get? Would you throw someone into your competitor to get?
Harry Stemmings
Yes.
Jason Lamkin
You really think of those 2,000 people if they could get someone working at a competitor feeding. Forget this happened to the seal level. What if just VPs of sales could do it? Right? 93% say they lie in deals. 93%.
Unknown
I think there's a big difference about lying about a product Runway and sorry, a product roadmap. And when a feature is going to come, I'm going to orchestrate a spy in Rory because he wasn't paid 200 million. Sorry, buddy. And I'm going to plant him in. Dude, that's.
Jason Lamkin
Listen, I like to think of myself as fairly ethical. I'm not sure the line is as black and white as you think. I think of 93 folks are living in deal. How many sales reps have gone to a competitor sales pitch, wasted a rep's time for an hour to learn their thing? Does that cross the line? Doesn't line. And how many of them, if they could make. If they could make a million dollars a year as an ae, wouldn't have their buddy sending them information? How many reps have taken the Rolodex with them? How many folks take their Rolodex with them when they leave? Which violates many laws, all of them.
Harry Stemmings
Yeah. I remember in 2003, a company who shall remain nameless did something like this. The only difference is the FBI pulled up at the company, next day they're accused of stealing trade secrets and they just basically empty out at every desk. And the process grinds on. I think a lot of this stuff people will experiment and figure out where the line is and they'll discover by going over it and getting caught.
Unknown
Is it a little bit coincidental that Rippling are going to go out and raise money now at $18 billion, if.
Harry Stemmings
Only for his cunning and acumen, you'd want to give him money that was.
Jason Lamkin
I think it's an anti. Coincidence.
Harry Stemmings
Yeah. Guy. You know, I don't think it's.
Jason Lamkin
I don't think it's intentional.
Harry Stemmings
It was pretty smart. I mean, catcher, that. Not. By the way, timing. I don't think there's anything in the timing. I just want to say that was very clever of the Rippling team to figure out what was going on and trap the person involved. I looked out and I thought, you win, dude. That was good.
Jason Lamkin
It was a good night.
Rory O'Driscoll
And then the way you reported it.
Unknown
Through Parker, like it was these people.
Harry Stemmings
You know, George, John le Carre, you know, a double age. Now we've got a double agent. They probably could have run him as a double agent for a while. Feeding false information. I mean, it's just great.
Jason Lamkin
The story got worse. Like most good stories, act two was worse.
Harry Stemmings
@ first.
Jason Lamkin
It went out when Parker's first tweets went out. Right. I remember someone asking me, it can't be this bad, can it? And I was like, no, no, I guarantee you I don't know him well, but I've known Parker for years. It's gotta be worse. He would not, given fundraising, given other things, he would not do this. There's no way he would waste his time. He has a complicated company. It has to be much worse than the first set, otherwise you can't do it. It's too. Just this is. This stuff is so distracting, isn't it? Or you've seen it on boards. It's so distracting.
Harry Stemmings
Right.
Unknown
Is this a case where it can take down the company, though, or. Actually, news cycles are so fast these days. I honestly believe that Trump does something crazy, Elon does something crazy, we move on, no one cares. The B2B customers really give a shit.
Harry Stemmings
Probably not. Because in the. I mean, in the end you can always make a change. You know, you can do that, whatever. What would every. This. I don't know the dynamics of this company. What would happen in a public company.
Jason Lamkin
Yeah.
Harry Stemmings
The rest of the board will do the unshocked and appalled. The attorneys would come in and explain the Fuji obligations and they would basically say, you sacked this guy right now and you can burn this liability off. You stay in this thing. You would download the ship and you're going to get sued by everyone. They would be drawing up the foreclose termination before the attorney stops speaking. The person in question would be out. They'd hire an interim CEO, a crisis PR manager and they'd say, as I say, shocked and appalled to discover this is going on. New day fresh boom. Pick your cliche. Hire Scadden, you know, some ex SEC lawyer to go on the board and do the whitewash and power right through. You'd lose a year. That's what you do if you're building them. Maybe if these guys have board control, they don't do that. But if I was on the board, that's be where I'd come in from. Companies are bigger than any one person. Sacrifice them and move on.
Jason Lamkin
I don't think many customers are going to leave. Where it might hurt you is at the margin it's going to hurt you. For new customers, it's a weapon for the sales team to use against you. I say 2%. Even just churning, you know how much work it is to change payroll providers. I'm outraged, but not that outrage to.
Harry Stemmings
Do any work when it gets company endangering, you fold. But you're right. I don't think it will be because there's a lot you can do.
Unknown
So we're going to play a game and then we're going to wrap up. Okay. The game is called buy or sell. Sell. I'm going to say an asset. I'm going to say a price and you can say whether you buy it or not, not sell because it's not like a negative. So. But that's a really important. That's a really important addition. It's not a negative. It's just like I wouldn't advance in that price. OpenAI at 300. Buy or not buy.
Harry Stemmings
Not buy.
Jason Lamkin
I recently took a look at my investments. I can't make any decision well north of 100, so I'm out. All my decisions are bad. North of 100 they're just all bad for a variety of reasons.
Unknown
I'm the opposite of you two. I would buy the shit out of this. Escape velocity reached cursor at 10 billion.
Jason Lamkin
The irony is the AR multiples for some of these if their error are pretty low, relatively speaking, if you're really paying 10x forward revenue on some of these deals, we've all done worse.
Unknown
By the time I did Lovable, it was like 10x revenue.
Harry Stemmings
The whole reason this business is awesome is there are singularly amazing companies in every generation and maybe these are they. And when you do those companies, everything works. And you're just so glad you bought it at any price. That's why this game is fun. All the things being equal, you should be doing private equity. The reason it works is because you have those singularities. I just don't know enough on the data to know if this price gets to that point.
Jason Lamkin
You know, the thing is, I know you want a one word answer, but going back to the beginning, if you want to tie a bow on it, right, the problem, if, listen, if it's a SaaS company with highly durable revenue, then Curse or any sphere of 10 billion is a good deal. It's not like a great deal, but it's a good deal. If this is A classic high NRR coming up on a billion 140, it's probably got 140 or 200 NRR on paper, right? So if you treat this as a B2B company with a massive moat that has destroyed its competitors, pretty good deal. Now if you look at everyone I talked to who in a week switch, they're like, oh, Windsurf is cool. You know, my portfolio companies switch back and forth. They're trying, they're switching IDs, which seems crazy to me. My son is switching. It's like then at this durability, this is the question of the ages for us is, is this revenue durable? Because if it's SaaS, then take my money a cursor, right? I just Wish I had 500 million. But if it's not, I, you know, this is the, this is the risk to Rory's point, right? Because as a SaaS company, they don't get any better, right? There's nothing better than those metrics.
Harry Stemmings
And you can Back to the OpenAI comment. You can say it's Google. It takes the entire market cap. That gives you plus or minus a little over a trillion. So 3, 4x from here, if you replace all of Google in three or four years, you know, is that the best 3 or 4x you could do? I don't know.
Unknown
Guys, listen, I've loved doing this. Rory, it has been so fantastic to have you with us. Thank you for joining us. This has been amazing and I really Appreciate it, Harry.
Jason Lamkin
I think you need a $4 billion fund for the next one's my big takeaway from your bet, the way you like to bet. I would go for 4.5 billion. I would start there. I would do a hard cap around 5 or 6 because it's going to be hard to deploy in 24 months. But I do 4.5 for the.
Unknown
Just remember, we like to stay small with small funds.
Jason Lamkin
We're small and focused partners and we all work on all deals together.
Harry Stemmings
So we're cap remembers right at the end that we got to stay on message. That was really touching, Harry.
Jason Lamkin
Right?
Harry Stemmings
And now, of course, you have editorial control so he can just nuke all his crazy shit, leave ours in. And at the end, Harry stubbing says, I really think we need to stay focused and keep our deal size small. No wonder you're a fundraising genius, Howie. I'm wise to you.
Unknown
Oh, wow. You know me so well, Rory.
Harry Stemmings
Good for you.
Rory O'Driscoll
My word, I so enjoyed that show. Now, if you want more shows like this, please let me know. I want your feedback. I think Rory was such a great addition to me and Jason. But let me know what you think of that show and I would love.
Unknown
Your thoughts and feedback.
Rory O'Driscoll
But before we leave you today, here are two fun facts about our newest brand sponsor, Kajabi. First, their customers just crossed a collective $8 billion in total revenue.
Unknown
Wow.
Rory O'Driscoll
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Summary of 20VC Episode: "Why Seed is for Suckers | a16z's $20BN Fund & Founders Fund's $4.6BN: What Makes Them So Good | Why Josh Kushner Is the Master of Venture Capital Strategy | Why Extended Private Markets Screw US Citizens with Jason Lemkin and Rory O'Driscoll"
Release Date: April 17, 2025
In this episode of The Twenty Minute VC (20VC), host Harry Stebbings engages in a profound discussion with venture capital luminaries Jason Lemkin and Rory O'Driscoll. The conversation delves into the evolving landscape of venture capital, contrasting traditional seed investing with the burgeoning trend of mega-funds. The guests explore the strategic imperatives driving funds like Andreessen Horowitz’s (a16z) $20 billion fund and Founders Fund’s $4.6 billion fund, while also addressing the broader implications of extended private markets on U.S. investors.
The episode opens with a blunt critique of seed investing. Jason Lemkin provocatively states,
"[00:15] Jason Lemkin: Why struggle to pretend you can do 8x over 20 years on a seed fund when you can just write one big check into a winner and call it a day and achieve liquidity in a quarter of the time, the multiple will be lower, but the absolute return will be higher. Like, it's so stupid. Like, see this for suckers."
This sets the tone for the discussion, suggesting that traditional seed funding may no longer be the optimal strategy in today’s venture landscape.
Rory O'Driscoll expands on the shift towards larger fund sizes, highlighting how firms like a16z and Founders Fund are adapting their strategies to deploy substantial capital more efficiently. He explains:
"[05:39] Rory O'Driscoll: ...the existing market saturated, so all the growth rates flattened out. ... and these new AI startups took off where unlike the SaaS thing where, you know, stuff was the same for 20 years, this shit changes every six months."
This rapid evolution, especially driven by advancements in AI, necessitates a departure from the slower, more methodical pace of seed investing.
Harry Stebbings and Jason Lemkin discuss the strategic benefits of deploying large sums in promising ventures. Harry remarks:
"[12:09] Jason Lemkin: ...you're paying up so much that even that upside has been competed away, then it's a sucker bet."
They argue that while larger investments carry higher risks, the potential for significant returns justifies the shift away from smaller, seed-stage bets.
The conversation delves into the complexities of managing risk within mega-fund strategies. Rory notes:
"[13:42] Jason Lemkin: You think we'll have more bimodal results where a lot of funds will just be massive unperformers because it's hard to assess the risk properly."
Harry concurs, emphasizing the increased individual deal risk and the extended holding periods required for substantial returns.
The guests examine how the influx of capital into large funds affects LPs and the broader investment ecosystem. Harry articulates a concern:
"[20:55] Harry Stebbings: ...if LPs are going to steer on the trailing 10-year returns and overshoot on capital in, and then at some point those returns will go the other way and then it'll take a while for the shoe to drop and then they'll start withdrawing capital."
This highlights the potential for a capital oversupply, which may not be sustainable in the long term.
A significant portion of the discussion centers on founder secondaries, where founders sell portions of their equity early in their company's lifecycle. Jason Lemkin observes:
"[71:10] Unknown: ...founder secondaries are completely the new norm."
They debate the implications of this trend, suggesting that it may lead to increased risk for both founders and investors, as capital becomes more concentrated and liquidity preferences evolve.
The episode does not shy away from ethical considerations within the venture ecosystem. The guests discuss the prevalence of misleading practices aimed at winning deals. Jason Lemkin shares alarming insights:
"[78:14] Jason Lemkin: ...93% of 2000 B2B folks are lying in deals."
This raises critical questions about transparency and integrity in venture negotiations, potentially undermining trust within the industry.
Harry Stebbings draws a distinction between venture capital and private equity (PE), noting:
"[22:32] Harry Stebbings: PE guys just hate that because they can look at it and go, I get it, you're doing 100 million now you can grind it..."
He underscores that while both models aim for profitability, their strategies and risk appetites differ markedly, influencing deal structures and investment outcomes.
In contemplating the future, the guests ponder whether the current capital influx into venture will continue or retract in response to market dynamics. Harry predicts:
"[56:06] Harry Stebbings: ...at some point you'll see less. It boils down to this private for longer class..."
They suggest that while the opportunity set has expanded, there may be an eventual correction as LPs reassess their allocations based on ocurring returns and market saturation.
As the discussion wraps up, Harry emphasizes the importance of strategic alignment with fund size and investment focus:
"[43:43] Harry Stebbings: ...fund size is the strategy."
Jason Lemkin adds a practical takeaway for fund managers:
"[85:31] Jason Lemkin: I think you need a $4 billion fund... a hard cap around 5 or 6 because it's going to be hard to deploy in 24 months."
The episode concludes with a consensus that while mega-funds present lucrative opportunities, they also demand rigorous execution and disciplined portfolio management to navigate the heightened risks effectively.
Notable Quotes:
"Why struggle to pretend you can do 8x over 20 years on a seed fund... seed is for suckers." – Jason Lemkin [00:15]
"All the best startups I've invested in are working 7 days a week, 12 hours a day." – Jason Lemkin [10:51]
"The upside is there, and it's huge." – Harry Stebbings [12:09]
"The enemy of great venture returns is capital concentration limits." – Brian Singerman [49:01]
"93% of 2000 B2B folks are lying in deals." – Jason Lemkin [78:14]
Key Takeaways:
Shift from Seed to Mega-Funds: Traditional seed investing is being challenged by the rise of mega-funds that deploy larger capital sums into later-stage companies, particularly in high-growth sectors like AI.
Increased Risk and Complexity: Larger funds face heightened individual deal risks and require more sophisticated portfolio management to ensure sustainable returns.
Impact on LPs and Market Dynamics: The influx of capital into large funds may lead to market saturation, potentially pressuring LPs to reassess their investment allocations as returns fluctuate.
Ethical Considerations: The prevalence of misleading practices in deal-making underscores the need for greater transparency and integrity within the venture ecosystem.
Future Outlook: While mega-funds present significant opportunities, the sustainability of current capital trends remains uncertain, with potential corrections on the horizon as market dynamics evolve.
This episode provides a comprehensive exploration of the current venture capital landscape, offering invaluable insights for investors, founders, and industry stakeholders navigating the complexities of modern startup funding.