
AGENDA: 00:00 Why I am 100% Equities and 0% Cash 04:35 Nvidia's Massive $100BN Investment in OpenAI 08:39 Is Anthropic Negatively Positioned by OpenAI Gaining NVIDIA Investment 27:30 Is Triple, Triple, Double, Double Dead 44:00 Navan Files to Go...
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Jason Lemkin
Well, I'm excited because just like 2008 at the moment I'm zero percent cash founder friendly has become bullshit. Any hot AI deal, there is no diligence provided, nor is any done right. It's just done on Saturday. Why would you do diligence? All you can lose is one extra money. Why would you do diligence?
Rory O'Driscoll
Having an early success is highly correlated with future success. Partly you get the referral effect, but partly I think it's that you just have the stomach to roll the dice and you get braver.
Harry Stebbings
This is 20abc with me, Harry Stebbings, and it's my favorite show of the week. Jason Lemkin, Rory O' Driscoll and items of the week. We have OpenAI getting $100 billion investment from Nvidia is triple, triple, double, double dead. Have growth expectations changed forever? Then we touch on a lot of other topics including notion hitting 500 million in ARR and many, many more. This is a fantastic show. Let me know what you think, Harry, @20vc.com I really want to hear your feedback. So let me know what we can do to make it better. But before we dive into the show today, let's talk about age. Specifically Piper, the AI SDR agent brought to you by Qualified. The agentic marketing era has arrived. And if you're a B2B marketing leader looking to scale a pipeline generation, Piper, the AI SDR agent. Wow, it is here to help. Piper is the number one AI SDR agent on the market according to G2. And hundreds of companies like Box, Asana and Brex have hired Piper to autonomously grow inbound pipeline. Fucking sign me up. Anyway, Qualified customers see massive business impact with Piper. 3x increase in meetings booked and 2x increase in pipeline. Wow, that is some results. Hire Piper, the 1 AI SDR agent and grow your pipeline today. Learn more at qualified.com 20VC that's qualified.com 20VC with the 20VC spelled out in letters, for goodness sake. And while Piper builds your pipeline, Attio gives you the CRM power to close and grow those relationships. Attio is the next generation of CRM built for the AI era. Fast, flexible and powerful. No, it's not a sports car. It's a CRM system, baby. It is Attio and it takes less than a minute. Sync your email, your calendar and you'll instantly get all your relationships enriched in real time with incredible data, no manual input needed. Attio also integrates with your existing tools and syncs with your product data to deliver an AI Native platform that's tailored to how your team actually works. You can model your CRM around your business, automate complex tasks and surface real time insights all in a platform designed to scale with you. With Atio, AI isn't just a feature. No, no. It is the foundation. It's powerful. It's AI automations. It's research agents that transform your go to market motion. It's a data driven engine. From intelligent pipeline tracking to smarter product led growth. Fast growing startups like Flat File, Replicate and Modal are all experiencing what's next. So get ready to build without limits and start now. Attio.com20v and get 15% off your first year. That's attioattio.com20vc. Okay, pipeline sorted. Woohoo. Now what about your own legal team? Enter Logora. Logora is the category defining AI platform that's fundamentally reshaping how legal work gets done about frickin time. Empowering lawyers across tier one law firms and in house teams to achieve more with greater precision and confidence. So Ligura does this by solving really concrete tasks such as document extraction, reviews against a firm playbook and suggesting well crafted markups directly in Microsoft Word based on your preferences. My word, that is a topic list of conversation that will not get a second date. But anyway. The adoption of legal AI is surging across the world and Lagora is at the forefront of this shift as the chosen partner to 250 industry leaders in law across more than 20 markets. The likes of Goodwin, Burden, Bird and Deloitte are making daily use of Ligora platform to review and research with precision, draft Smarter and collaborate seamlessly. They recently also got an $80 million Series B from Iconic. They're backed by General Catalyst, Redpoint, Benchmark and yc. Also they operate out of New York, London, Stockholm. Yes, they're Swedes. Always a wonderful race. With over 100 employees from some of the world's leading global law firms and tech companies, the team is growing super rapidly. They're just freaking awesome. Just go use Legora. Honestly, I love Max, their founder. He's just a great dude. Go find out more. Legora.com youm have now arrived at your destination. Guys, I am so excited for this. We have a lot to get through. I even have graphs this week. I mean this is like. You see this? This is yeah, intense. I don't know what that's how many.
Jason Lemkin
GPUs you're buying from Nvidia. Is that what's your. What's 20 VCs commit it's up and to the right.
Harry Stebbings
That's all I see from this graph. Now what else do we start on? Nvidia invests 100 billion into OpenAI I wanted to start on this. Is this an infinite money printing machine where we have Nvidia invest in OpenAI who commit 300 billion to Oracle who then buy more Nvidia chips. Is this just a way to print money these days?
Rory O'Driscoll
First of all, it's not an infinite money machine because it will end. What it means is that Sam's going to get to make the bet he wants to make, which is apply infinite amount of capital and see how long these scaling laws last. And no one's going to call timeout until you actually hit a wall because what this says is Nvidia is going to get rewarded for, everyone's going to book gains and if it all works, it'll all be good. It's like any aggress financing strategy. If the underlying business works, everyone looks smart, the debt gets paid back, the equity goes up in value and everyone's a hero. And if it doesn't work, it all comes back and bites in the ass. What this means is if it turns out that those set of OpenAI projections of $100 billion plus of revenue or whatever the numbers are, are real, then we're going to get to find out because no one's going to call time out along the way, at least for another year or two based on this because everyone's getting the capital is being made available and everyone involved is getting mentally marked up. That's my takeaway. They're going to get to find out.
Harry Stebbings
Here I have to intersect. You said there Sam gets to see if scaling laws do continue. I thought we all agreed that they didn't continue. And that's why GPT5 was focused on efficiency and that's why we actually didn't see improvements in the way that we thought they would. I thought we were already reaching that.
Jason Lemkin
I think you got to listen. The one thing I've learned over the course of the show is to really listen to what Sam Altman says. Elon Musk will say something and it happens. He's just like a couple of years off, right? But it always happens. The self driving cars and the rockets, right? Sam says something and it happens like kind of soon. And he says it without off the cuff. And he's sitting there with Jensen and Brockman this week saying this is just a start. We need three orders of magnitude more compute than this, not ten times as much Three orders of magnitude more, he says. And then he writes today calmly, just with this first slug, the hundred billion, hopefully we'll cure cancer and educate all students, right? There's a lot going on there. He said Stargate, and we didn't understand it. Now, he didn't just say 100 billion. We could talk about the round trip revenue. Is it really round trip revenue? There's some interesting questions, right? But he and the President said it was. They did three orders of magnitude more than this to achieve what they're predicting today, their goals. This is not Sony baloney. This is what they have on a whiteboard in a spreadsheet.
Rory O'Driscoll
To be clear, I didn't say it was correct, Harry. I just simply said we'll get to find out. I'm not sure I believe that the marginal $300 billion will earn a return on capital at all. But my point is simply, there's some aggressive business projects where you go, I wonder, can we invest that? And you're just not able to make those investments, so you don't get to find out. And then there's deals where the market says, here, you can have the capital, have a go. This is one of those deals. We will find out. I mean, as the cliche goes, that's why they play the game. I'm somewhat more skeptical because I think the level of heroic assumptions you have to start making to make these investments all work is high. But the truth is, we're human beings and we tend to when someone is as astonishingly right as OpenAI has been over the last six years, it's just human nature to say, I'm going to continue backing this bet as long as it works. The consequence of that is it goes on until it stops. In other words, you got someone who's clearly going to keep doubling down. So the doubling down is going to keep taking place until the return on the double down, isn't there? Is that now? Is that already happened? Is that going to happen three years from now? I don't know. I can speculate. Why? I think no. But the market has said, have a go. Here's 100 billion.
Harry Stebbings
If you are Dario today, are you thinking, wow, we are in a significantly disadvantaged position as a result of this. And does this 100 billion move the needle significantly more in favor of OpenAI?
Rory O'Driscoll
The question is, what is it giving you? It's giving you capital and access to chips. So do you feel constrained by those? You probably aren't constrained by a lack of capital. My understanding is they were beating people off with A stick on the recent entropic round. And if they decided they want another 10 billion, it'll be there tomorrow morning. So they're not capital constrained. So maybe you'd say it gives you some preferential access to GPU that OpenAI now has. So I mean, yes, in the oh my God, their capital is bigger than my capital wars, I think you'll feel the need to respond and do something. But it'd be interesting to actually pencil out what exactly other than momentum and bigness, what problem you're trying to solve?
Jason Lemkin
Well, I mean Anthropic's not going to be able to build its own GPU like ChatGPT is. It's not going to be able to lease create hundreds of gigawatts of compute without that capital. It's not going to be able to build its own gpu. I when another thing I thought through all this news which, which didn't really come up in any analysis I saw, I was thinking about this a little bit. I'm thinking another thing that Sam is very clever on is toeing the line on being a monopolist. OpenAI does not want to be a monopolist, nor does Nvidia. They both want to be very careful in how they position themselves. I think Nvidia has an existential risk which is everyone is trying to take their share, right? Google has its own TPUs, Amazon's trying, right? OpenAI is building their own to. To. To take away market share. But they both need to be careful. But OpenAI I don't think they want 99.9% market share. They've already been through enough drama and trauma with Microsoft and throwing Sam Altman out of the company and bringing them back. You need. They need like their, they need their number two, possibly. Or they're at risk, right? Because they might be a monopolist in some ways today at a consumer level, Open AI. Oh, I thought no, I use cloud every day, like but you're weird if you use Claude, right? On the consumer level, they border on Google Chrome levels of market share. And Sam's very careful to not denigrate others, right? Other than a few jabs at Elon because he needs a little bit of this so that he's not ripped apart as a monopolist over time. Like this is an epic monopoly like we've never seen. Think how much ChatGPT already dominates our lives. It's a standard oil of tech.
Rory O'Driscoll
I feel the need to cynically say that the objection to monopoly is the extortionate excess Profits monopoly extorts from the consumer. Never have there in that basis been a less successful monopoly than ChatGPT because they're subsidizing. I saw. We'll talk about it later. An estimate of the consumer surplus delivered by ChatGPT in the tens of billions of dollars to some extent. Jason, that was glib. I hear what you're saying. It's obviously not a cash extraction monopoly at the moment. But you're right, they have commanding market share in the consumer market. Though I think between Gemini and Perplexity, I think they would argue not a monopoly. I think Nvidia frankly is far closer to being a monopoly in terms of market share than ChatGPT, which is why I thought you were going there. I do think it's interesting that there's a whole bunch of people talking about building processors to try and take away that revenue and I'm sure they're hyper aware of that. It would be fun to know what, if any, agreement was made on OpenAI making their own chips as part of this deal. It's hard to imagine giving equity to someone who's literally building when they're one of your six largest customers and they're building a competitive product. So that's a little something it would be interesting to know. But that on the other hand is a detail that probably will not be highlighted just given the dynamics.
Jason Lemkin
Well, Nvidia is weird too because it has elements of a monopoly, but it has elements of a monastopy too. It only has two customers. I mean it has a long tail of customers, but it has to make sure it doesn't only have one customer. It has a risk of only having one customer.
Rory O'Driscoll
I think you are. I think six customers I saw on the last quarterly accounted for something like 83% of the revenue, which again, which is astonishing. First of all, let's step back. That's astonishing. Look at the market cap, their $4 trillion market cap. Look at the two other 4 trillion, three 4 trillion dollar market cap companies, Apple and Microsoft. Apple has 2 billion customers everyone on the planet. Microsoft has probably a couple of 500,000 plus meaningful enterprise customers. These guys have six. When you say it like that, it makes you realize, frankly, and again, I don't want to be the Debbie Downer, how single threaded the market cap of the largest company on the planet is on the spending decisions of six or seven people. Now the good news for Nvidia, and this is why I go back to the consequences here. None of those six or seven people look like they're blinking OpenAI ain't blinking. Google's made it clear multiple times. I saw a good quote visit from Boko Capital that just reminding us. Google have said over and over again, I ain't blinking. Obviously, Facebook meta has indicated an absolute willingness to tear up the book and do anything it takes to win. And Oracle ain't blinking. It's just this really weird dynamic. You've got this company worth 4.5 trillion with only 6 customers. That's bad news. But the good news is all six of them are determined to spend themselves into oblivion to win the prize. It's a fascinating game.
Harry Stebbings
What's interesting for me is the revenue concentration expands just from these providers in this space to the data labelers as well. You know, we just have Macaw on the show to Macaw customers make up 55% of the revenue. I spoke to the other four main providers. It's exactly the same and it's the same two customers across the mall. It's fascinating. They are incredibly promiscuous with their data labeling providers and they just use all of them. And they are the two same for every one of them.
Rory O'Driscoll
Yes, because that's the only people who want to buy their shit at scale. I mean, I always like to distinguish does the AI revolution, but does the AI capex boom? I mean, there is an AI boom at the apps level. In other words, yes, adoption's taking place. The real wow in the last three years has been just the fact that the CapEx boom that the markets and these six deciders have been willing to let the capex get so far ahead of the revenue that they've been willing to say let's spend in aggregate 600 billion of capex per year on a market that today, depending on how you add up, all the revenues is yielding 30 to $40 billion in revenue. It's amazing. Anything co attached to that capex boom has just killed it. And you're right, the data labeling, which I'll be honest, we looked at some of those in 16 and 17 and we're like, is this a really great business in theory? No. If you have a services business and you're only selling to six customers, you can make this intellectual MBA case that oh my God, they'll get ground down on price. That case is totally wrong because those six customers don't have time to optimize. No, one of those six customers is trying to optimize their cost basis. They're just trying to build as fast as they can. And if you're merkur, if you're Serge, if you're anyone in the line of that, you're just picking up your dollars and stuffing them in your bucket as fast as you can.
Harry Stebbings
It feels so nuts to me seeing $100 billion go into an OpenAI. And that is a headline when you compare it to any other time that you've been investing. Does this match any other time in terms of what? Holy cow, Shock.
Jason Lemkin
It's a good question. I think these analogies fall apart because the scale is so many orders of magnitude larger. Right. The only thing that's different, that's similar is the sense that it's unlimited. Right? That it's unbounded. And we actually have more skepticism today than we probably did back then. Rory's skeptical of the limits here.
Rory O'Driscoll
I totally agree. I think I'm not skeptical of the long term trend. Does it feel like 99? Not complete analogy. History doesn't repeat. It rhymes. But it's more like 99 than anything else I've seen in the last 20 years. I remember Nortel and Lucent making big vendor financing commitments to their big bandwidth customers to sell equipment, just as Nvidia is doing today. Though interestingly, Nvidia is doing it as equity, not debt. But fun. I do remember that sense, Jason, you said it. Unlimited possibility, endless belief. And I remember it also collapsing very quickly in 2000.
Jason Lemkin
I mean, I think Harry's got a good point. This limitless potential, this is the first time we've seen it back then, right? It's not like other booms, this limitless potential. It's not the cloud boom when we were all locked up in our homes. This is a feeling that could be limitless. What's so different though in the web 1.0 days is there just wasn't enough money. I mean, Amazon almost ran out of money after its ipo. Now, bless their souls. We've got, we've got all the leaders running around guaranteeing each other self core. We can now not go out of business. Like in, in 2000 core we would have imploded in months because it would have run out of money. Now Nvidia has agreed to buy a 300 years of its capacity. Everyone's guaranteeing everyone. So this unlimited capital yet of course maybe it ends. But that's nothing like the Web 1.0. There was just no money. Listen to this for just a second here, okay? Nvidia Fiscal year 2023, $3.8 billion in free cash flow. Fiscal 2023, pretty good, right? 3.8 billion. Fiscal 2024, 27 billion Fiscal 20, 25, 60 billion, 100 billion or something in the next fiscal year. That's a lot of cash to reinvest from your balance sheet.
Rory O'Driscoll
You funny you should say that. Yeah. Because I actually looked at the same number this morning and yes, the free cash flow is $60 billion. So that's obviously, to state the obvious, a a lot of money. Again, the bear case. That's a lot of money and a lot more than it was two or three years ago. In that context, I was surprised. They have a buyback program they've been buying back. They bought 9 billion of stock back last quarter, which is just interesting at this period in the cycle. And they've authorized a 60 billion buyback program. So in other words, there's a buyback program equal to the free cash flow for the last year, which is just interesting and aggressive. Cash on the balance sheet hadn't looked forever. It's 60 billion, which is a lot, but it's only 1.5%, 2% of the market cap. You kind of go and say here is that if this amazing market doesn't keep going just the way it's going now forever, then you could find yourself going, maybe I shouldn't have bought back $9 billion worth of stock at whatever it is, 180 a share. And I'll look back on that and say that might have been a mistake. And again, I find like I'm the doomer here. I'm not a doomer. I think the trends are great, but it's just a very frothy time.
Jason Lemkin
I wish I'd done the math ahead of time. What I saw when I was at Adobe, which I think Nvidia is doing the same. It's not a brand new company. Nvidia, right. Boom aside, they do try to buy back equal to the option dilution, the RSU dilution. Right. It was almost one to one when I was at Adobe. Right. This is how you maintain your EPS at Adobe, was by buying back everything equal to the dilution you give out in RSUs, which was just frankly a cash equivalent until the market boomed.
Rory O'Driscoll
Right. It's almost a one to one and flagging vigorously. My opinion on that, as I've done when I've been on board, I think the buyback, the same as you're diluted, is as dumb as rocks. You should buy back when your stock is cheap and you should sit on your cash when the stock is dear. I think the idea of linking it to your equity dilution, again, reminding us we said we'd level up remind the listeners, lots of public companies, obviously they issue stock to their employees and there's this ostensible rule that maybe you buy back in the market around the same number of shares as you've issued to stock to keep the share count constant. And you're right, Jason, loads of people do that. I think it's absurd. But what can you do?
Jason Lemkin
It at least keeps your stock based expense honest. Like if, you know, a lot of folks losing money are pretending it's not an expense. If you're profitable and you buy it back, it's like, look, this is the same as cash. It's just a little bit of financial engineering.
Rory O'Driscoll
It doesn't appear in the P L, but for sure, look again, it's back to the. The zoom out comment is the same in a bull market. No one focuses on balance sheets. We only talk income statements. And when things get tough, you're like, oh, wouldn't mind having some extra money around. And stock prices that were high can be low. Typically, corporations historically have a terrible record in terms of they typically buy back stock at peaks and don't buy back when it's cheap. I see no reason why humans will change this time.
Harry Stebbings
Ladies and gentlemen, study Larry Ellison, the master of this.
Rory O'Driscoll
The master who exactly, when it was cheap, bought it all back and then use the capital to totally change the game to the current game of capex and investment and has made it work.
Harry Stebbings
Rory, that's great, but what about me? Your favorite thing about chatting to me? I'm looking at my public book and I've got 28 holdings and 27 are green and I'm in the money. And I'm thinking, I'm humble enough to know I'm not that good. And I'm looking at the S and P going, really? It looks like it's going to hit 7,000. You think it's going to hit 7,000 pretty soon, guys. And would you be selling now? And how do you think about when to catch the fallout knife?
Jason Lemkin
Well, I'm excited because just like 2008, at the moment I'm zero percent cash.
Harry Stebbings
Zero percent cash, nothing.
Jason Lemkin
I have no cash whatsoever. I had some cash just like 2008. I remember feeling it was so great when the market crashed and I literally did not have enough cash to fix the roof on my house. I mean, I ended up stock, right? But nothing was more fun than selling my stock at a 70% loss or 60, whatever. The worst of the crash was to fix that roof. I remember like feeling like such an idiot. And I don't have a cent of cash right now.
Rory O'Driscoll
It's by definition hard to know. That's what the data says. You can throw out two factoids. One, either way, the correlation on valuation and short term return is pretty low. In other words, you can say stocks are expensive and the Correlation on predicting one year returns is pretty crap. The correlation on 10 year returns is pretty good. At this current valuation, your likely 10 year return in the public markets is significantly lower than average because it's more expensive of going in. Now. That's the long term message and that's a pretty grim message. And the short term message is oh my God, the Fed's cutting rates, blah blah blah, things are going up. What I do with that information, since you ask, is I accept that the cost of sleeping at night and having some portion of cash is accepting a level of underperformance. But you make an asset allocation decision based on what you want over the medium term, not what's going to optimize. Just in a bull market.
Jason Lemkin
I'll tell you what the frothiest sign is. Well one we're all invested in Nvidia, right to Harry's point. In the public markets all our 401ks are in Nvidia. We're all on this ride together. But the frothiest sign is now LPs are bragging about their returns on LinkedIn LPs when LPs are start bragging about their returns. To me that's the most 2021 moment I've seen when LPs are LPs who are usually hide behind the wizard of Oz curtain or bragging about their returns.
Harry Stebbings
I have everyone in my Twitter being like Hemont saying triple, triple, double, double is dead is the top. So like there are many signs that people think I disagree with that. I do want to discuss 75% of VC dollars in 2025 went to 19 companies. Is this just an extension of Mag7 and concentration of capital? Is venture itself changing where we're all doing a Kleiner Perkins and moving late stage to get into the surefire winner.
Rory O'Driscoll
First of all, it's obviously a stunning fact. But a better way if I may say of thinking of it is not has venture capital changed? It's that the 25% that's remaining is in fact the same venture that's always existed. It's roughly, I mean I think in our space 1000 something odd series A's. Every year certain percent will go to B's and that business has stayed the same plus or minus 10, 20% for the last 10 or 15 years with fluctuations. What's really happened is on top of that business has emerged this totally separate business called as you say, ultra late stage private public style investing. And I just think of that extra 50 billion a year or whatever it is added on top didn't change my business. It just means there's another business that you can choose to be in or not that exists one layer, one, maybe two orders of magnitude above you in the valuation world. And it's still private, it's still reported as vc. It's just a different business. It makes sense that that's way more concentrated. You have A is more concentrated than seed. B is more concentrated than A, C is more concentrated than B. Because at every step some people fall out of the game. So the longer you hold private, the more concentrated it gets in the limit. Maybe we're just left with two foundation models and databricks and stripe raising a serious N or G X or whatever it is. But it all makes quote unquote sense. It's just, it's a different business than series ABC Venture Capital. It just gets reported in the same bucket.
Harry Stebbings
You guys have taught me so much. But one thing that Jason's always taught me is like try not to predict out several rounds and just predict out the next round and can you see a 3X there? And I really like that framing. We as a team do it. The hardest thing I find is honestly we are getting it wrong. A lot of our businesses now are growing nicely and I cannot predict what the next round once because it seems to be moving so much. And I'm having real problem predicting financing markets. Jason, can you predict which of your companies will be hot?
Jason Lemkin
I think it's always been easy when something is super hot to know it's super hot. Right? When you have top. Now, maybe Heman's right, maybe the top 1% has changed or the top 0.1%. Maybe we could be analytical about that and you can fall out of it, as we all know, right? But when you're in it, you know, like there's, there's no doubt, right? What's weird today is that level just below it where it's unpredictable. Like someone may see this as an outlier and preempt at a very high price and others may see the risk beneath the surface. Be concerned about margins, be concerned about churn, be like, it's very easy to criticize a lot of these companies on churn and margins, right? And so if you're just below that, whatever that that s Tier is that's where I find my ability to predict very, very murky. And then the one I disagree with you on, but I agree with you from, from Twitter is I think the ones one layer above that if they are triple, triple, double, double and you meet with enough people and you're not burning a lot, I do think you get funded, like that's where I quote disagree with you. But it's a lot more friggin work. It's a lot more work to get funded growing 100% at 20 million or 110% of 10 million than it was 24 months ago. It's just a lot more work because you can't get the meeting.
Harry Stebbings
I would just add one nuance. If you are in a slightly weird space that is traditionally unloved, like restaurants or like no one likes selling to restaurants, then where they would have taken a bet on you before with triple, triple, double, double. Now they're not now triple, triple, double doubles growth and you're in a space they won't.
Jason Lemkin
Or maybe I think it's unpredictable. I would say the opposite. Looking at owner, right, which we know, right, which is as they dominated triple, triple, dom, double, double, it's faster. But then what my learning is these models, like if you're growing at outlier rates, you're an outlier. Like I don't really care if it's tagging or at some. I mean we all want it to be AI native, right? But if you are hitting those numbers, people don't even dig beneath the surface, do they? They don't even care if they're. If it's a lot of forward deployed agents or this or that. I, it's. But, but I, but listen, if you're the 11th undifferentiated restaurant SaaS struggling to build a point view of sale at a million in revenue, people don't want to take that meeting, do they? At 50 million, 100 million growing triple digits, they'll take the meeting. There's only so many of those. There's only so many folks growing beyond triple, triple, double, double. At 50 to 100 million they'll take.
Rory O'Driscoll
I agree. I think that whole meme is a little overdone. 3, 3, 2, 2 is not good enough. Of course there are examples of companies doing better than that. A small number, but a meaningful number of companies doing better than that. But that's not the only game in town. And I think that if you really have clarity on that kind of traction, especially at any reasonable scale, I totally think you're getting Funded. I think you raise a separate question. Is what's really going on a story? Belief. People don't believe that the growth will happen in the future. But look, you just had a couple of IPOs where companies are growing 30%. Obviously that's at scale. So as long as you're on that kind of trajectory, I don't believe it's as sharp a line as some of the kind of Twitter thread, the Harry Twitter thread with Hamat makes it. Right. Yes, there's a small number of companies growing significantly better, especially early on in the foundation models. But I don't think it's the only game in town for sure.
Jason Lemkin
Look, it's sensational, right? We could break it down. There's a version of it I saw this week that was less dramatic, which was iconic. Right? And Iconic had $2 billion exits this week. Iconic growth, okay. It had net scope, which no one talked about. Eight and a half billion dollar exit. And they congratulated themselves on dx, which Atlassian bought for a billion, which I don't know how much they put in because they describe themselves as essentially bootstrapped. Right. So I kind of couldn't have owned a third of the company. Right. But are even those rounding narrows compared to anthropic? Right. It's just they equally congratulated, but with the fund sizes and expectations, do those, do those meet the bar? Do DX and Netscope meet the bar in 2025? Is it different version of Harry's question, isn't it?
Rory O'Driscoll
Well, as an absolute number, it's a great return. Let's start with that. I mean, again, if you have a $10 billion fund, you don't care. But most funds, those are excellent exits. I mean, netscope, superlative company, did a great job, built a big business. Superlative. Yeah, they are. Well, they are.
Jason Lemkin
But do they count in 2025?
Rory O'Driscoll
Yes, of course they count because they go in your bank account and that's the mission. If you own 10% of Netscope, you have a $700 million equity position in a freely traded public stock. Maybe you paid 100 million for it. You have a 7X. It's great. It's a great outcome.
Jason Lemkin
I don't think of this every day, but I do think about me and Emergence two back in the day. And Emergence two was an incredible fund. Right. So many winners in cloud. Right. The Vivas and all those. I was an asterisk at the bottom of the outcome, I was an asterisk. The returns were so gigantic. I mean, that was whatever a 10x plus fund. I was just a rounding error in other exits. Right. I just kind of think about who gets to be in the asterisk at the bottom of the DPI table in 2026, because I was in the asterisk back then. And, you know, it's cool, but it didn't feel great to find out I was in the asterisk.
Rory O'Driscoll
Interesting, but I understand what you're saying. But let's talk about multiple and then let's talk about absolute amounts. As the OpenAI cap table, quote unquote crystallizes. I think some of the early investors in 2019, and I'm doing it from memory based on their ownership versus the original capital, and it's around a 7 or 8x. So it's a magnificent company. It's the most important company of the last decade. But the actual multiples earned are really good. So someone who did the series A at Netscope also made a 7 or 8X. Now, maybe the absolute sums might be different. You could put more money to work, but it's just worth pointing out on the basis on which, as an investor, if you made those two bets, one of them being OpenAI from 2019 to today, and one of them being Netscope from 2017 to today, your IRR might be different, but in both cases you made a 7x and all 7xs are exactly the same. Because money is fungible. That's why we invented it. There's very few ways to make a good return on a large amount of money, which is why the bigger the fund size, the more you have to be in only five or seven deals. But there's quite a lot of ways to make meaningful equity returns on good outcomes. $5 billion plus IPO is going to result in a perfectly great 10x and everyone's going to cash the check. So I'm here in defense of none of those are boring. There's more ways.
Harry Stebbings
Scary listening to you, Rory. Sorry. A $5 billion IPO does a 10x.
Rory O'Driscoll
Well, again, by the way, it's not a 10x on the series A. I'm actually just doing it because I calculated I'm not going to name the investor. I calculate one of the investors because a lot of them, very wisely, in my opinion, have piled into the follow on rounds. So you probably your return on your first money is a 25x. Your return on the last round is a 3x. Blend it across everything. You have a 7x, but it's a 7x 100$150. If you want to Talk about the return on the Series A. My guess is it's 25, 30x at least. It's a great return.
Harry Stebbings
But it is also a company where 10% of the world's adult population is a weekly active user.
Rory O'Driscoll
Oh, we're now going back to OpenAI. The other 7X. Yes.
Harry Stebbings
10% of the world's population is a weekly active user.
Rory O'Driscoll
Yes. So we're now switching from I think we're the 7x in the mid mid sized tech centric IPO to the 7x that you get investing in OpenAI. Yes. Your return might be only the same, but obviously it's a company of far more stature and significance.
Harry Stebbings
If you had a Large position in OpenAI in the fund now, would you be selling?
Rory O'Driscoll
I think you'd have to think about it, wouldn't you? I mean if you're not thinking about it at 500 million, you're probably just not thinking.
Harry Stebbings
I completely agree with you.
Jason Lemkin
I don't think anyone's going to sell. I mean Iconic was saying they never got more calls than they got trying to get into the anthropic round this last round. They never got more calls in the history of Iconic than From their own LPs wanting to get in. Right. So I'm not saying you shouldn't sell, I'm just saying, boy, it's hard to be sitting at the fund and sell when you've never felt more strongly there's another card to play. Right? I mean the easiest thing in venture in the world is if OpenAI goes from 500 billion to a trillion and you don't have to take a single meeting, you don't have to show up to anything. All you have to do is open an email and your, your position doubles. I mean, it's so hard to say no. I mean, what, 80% of IPOs trade down, right? So that's a tough bar as it is. Right? But when you've got one like that in a frothy market, how do you sell? On paper you can, but in the like, good God. I mean the three of us are each going to make 50 million now, but if we just wait six months we can make a hundred and I don't and I got to pay taxes. I mean, I'd rather let it ride and defer the taxes on. I mean I can't even again, there's really only so much I can get on the Yellowstone Club for 50 million. I mean, after taxes I'm not, I'm sort of mid hill and I'm probably under the 3,000 square feet. And I don't even know about the radiant heating. So let's play another card.
Harry Stebbings
I think, I think the level of money. No, no, but Jose, I think you're right, Jason. I just think the level of money you have going in dictates your. Your willingness to sell. We're very candid and we're friends now, which is great. I don't have 50 million bucks.
Rory O'Driscoll
Yes.
Harry Stebbings
I would absolutely take it off the table because it's really meaningful when it's your first big hit.
Rory O'Driscoll
Agreed. It absolutely.
Jason Lemkin
There's also weird dynamics too. Rory could. Could educate us the most. This is what I think about is turns to the fund. Right. If you have a smaller have a fund returner. It's a weird dynamic because all the Internet advice says a fund returner is what you want to do. Right. But turning a fund returner into a 2x fund returner is a BFD. It's such a big deal for carry, for performance. Right. That's a nice but stressful position to have. Is a 1x fund returner with liquidity options. What do you do?
Rory O'Driscoll
I like the layout. It's a two step thing, process. First of all, you have to come to some kind of opinion on fair value and upside. And for the stock, I mean, you have to have some level of fund. It can't just be it's going to double because it's always doubled. You have to have some grasp of the fundamentals and say, what do you think this is going to be worth? Half a trillion. Makes it the 15th largest market cap company on the planet. It can go from here, whatever. But then I think the interesting thing you're saying is then you have to overlay on that the institutional or personal imperatives that come on top of just the raw expected return. And plugging a book I recently reread, actually a book called the Missing Billionaires, which was written in part by Victor Haghani, who was the youngest partner at Long Term Capital when they went spectacularly burst in 97. He's gone on to a career in wealth management. Truly excellent book. One of the best books I've read on portfolio management. The comment at the start is Cornelius Vanderbilt died the richest man in the world. And if all his heirs are done is stuck it in the S and P and lived on the dividends, there would be 15, 20 of them each worth a billion today. And there's none because he says people screw up bet sizing, they screw up portfolio management. And it's not about stock selection. As much as it's about the things you just mentioned, the institutional decisions, how much of your wealth should you have in one stock? What should you do with a 1x fund that's liquid, where you might see potential to a 2x? How certain do you have to be that it could double again? Because before you should leave, all your net worth in that stock actually ended up convincing me of. It's what Harry effectively mentioned, the marginal utility analysis. You do have to take into account your risk aversion. And we're not all just trying to maximize expected return. You should have some level of risk aversion. And the question is how much? As Harry said, when your risk aversion relative to the bet size changes with your net worth, if you don't have 5 million and you have a liquid 5 million, you probably should take that 5 million and then how that changes over time. Super well written book, quite quant at times. But you end up the meta conclusion I have is that most of us have a risk aversion of about as you quantifiers about 2. In other words, you're not going to let the bet ride for equal expected return and that's most normal human behavior. And then the second conclusion I have is some people lump Elon in that are just totally maximizing expected return. There's literally zero risk aversion in the system. They just want to make the bet. SBF had the same thing. He would do a 5149 bet. It's like some people just have super high risk tolerance to the point arguably of insanity. And those are the people who make great entrepreneurs. Most money people will take some money off the table.
Harry Stebbings
Do you think investors are like founders then? Whereas we say hey, take secondaries, take all that stress off the table. Do you think richer investors, investors make for more high upside investors because they're like let it ride. Sequoia aren't here to make a half a fund return, whereas an emerging manager oh shit, I need a half a fund return in dpi. I need dpi.
Rory O'Driscoll
I think at the margin it's almost certainly true. I wouldn't want the emerging fund manager to behave irrationally or just over optimize on the thing. But there's no doubt that a significant part of the advantage of a firm like Sequoia has is is just the innate belief that something else will turn up tomorrow. I don't have to fiddle around with this at the margin. And there's a bunch of stories about that I believe and again this is apocryphal I wasn't in the room. I believe the early offers on YouTube were significantly lower and the Sequoia guys were like, no, we're not just taking that. And the offer went up. In retrospect, given they sold for a billion and it's probably now at 100 billion, you wonder. But yes, there's no doubt that success begets success. Not just for all the referral effects that we could talk about. Like you get to see good deals because you've been successful, but there's also this very intangible effort thing, Harry, that you mentioned, which is people who've been successful are more willing to take risk. And the only way you get success is by taking risk. It's hard to correlate venture success with a whole bunch of things, education stage, blah blah, blah. But it turns out having an early success is highly correlated with future success. Partly you get the referral effect, but partly I think it's that you just have the stomach to roll the dice and you get braver. Now you can over extrapolate that and screw up. But there is no doubt that it's a lot harder early on to have the big cojones to roll the dice. And if you're Sequoia, it's probably a lot easier.
Harry Stebbings
We say about risk return analysis, concentration of assets. I hope he doesn't mind me saying this, but Auron Ziv has a lot of concentration across funds in the van and at points that has looked very, very nerve wracking. Point being when it went to zero in Covid, they announced, obviously they're filing their S1. I thought interesting elements. 613 million revenues growing 32% year on year, 10,000 customers, 110% NDR, which is good, not, not best in class, but good. How did you guys think about this S1 announcement?
Rory O'Driscoll
Before we talk about the S1, let's go back to Oren. Zev. Well done Oren, Good guy. Think about it. You made a very non diversified bet. It's terrifying. You then let's all remind ourselves you then had Covid and you're a travel company. Your revenue probably went to zero in March of 2020. And to go from there in a non diversified bet to having an S1 on file for a perfectly doable nice IPO. I can imagine the exhale when this puppy prices so well done him and.
Jason Lemkin
His investors, I mean you guys are better experts than me. Is it really as concentrated as it sounds? I mean if these are SPVs and opportunity funds and other things, is this him really putting 80% of a main fund into Navon or is this stacking a whole bunch of vehicles?
Harry Stebbings
I have no idea. I mean, Bonnie, I just may not.
Jason Lemkin
Be as, like, it may be a lot of his book, but it may not be as concentrated for his early stage fund as it sounds. Right.
Harry Stebbings
20% of a fund, dude, is a lot. And 20% across.
Jason Lemkin
I don't think it's a lot. I think you got to put. If you have a small, like what's. How big was his core fund in that.
Harry Stebbings
Do you have 20% of your fund in any company?
Jason Lemkin
Yeah, I'm a pretty concentrated investor, so I'm going to get to 10% almost in two checks into any deal. Listen, if you have 100 bets, it makes sense if. But if you have a breakout winner, this, you should put 20% into your winner. I think 100 is risky because Rory can help me do the math. Once your Fund is up 4 or 5x, 20% of the initial principal is not that much of your nav.
Rory O'Driscoll
Yeah, once you're up.
Jason Lemkin
I mean, once you're up.
Rory O'Driscoll
I mean, look, again, these are all trade offs. Concentration can result in increased outperformance at significantly more risk. Right. And the question is, again, are you getting paid for that extra risk? You know, look, I don't know if I'd have the stomach to put 20% in one deal. And I want to honor the fact that Jason clearly and Founders Fund, in my view, one of the most successful firms, have the stomach for that. And maybe it's just a risk tolerance perspective. I'd find 20% hard. I do think not all, but most investing vehicles have some element of risk diversification in them. There's not a huge appetite in most markets for undiversified single stock risk, which of course, interestingly enough, there is right now. And as you say, the anthropics and opening eyes of this world.
Harry Stebbings
I always remember Brian Singerman teaching me that capital concentration limits are the enemy of great venture returns. And that's why they have 33% of their fund in Airbnb. I don't have the balls. He does, sadly. Otherwise I'd be much richer, I'm sure. But I always remember that on the van. Point taken, Jason. In terms of level of concentrations.
Rory O'Driscoll
And I'm just going to. Before you go on to the van, I'm just going to make a comment back on that, citing the book again that I read. It was really interesting because it's. It made you run the exercise of what level of confidence would you have to have in the excess return from an individual stock to put all or half or a quarter of your net worth in it versus having it in the S and P as a whole, it quantifies your certainty level. One of the exercises it did was to say how certain would you have to be that Tesla is an outperformer to be 100% Tesla from the 2010 IPO on, any answers, you have to believe in about a 70% outperformer on the S and P, which interestingly is about where it ended up. So you can quantify these things. So instead of just saying, oh, I'm going to take risks, you say, how certain are you that this stock is going to do 20% better than any other stock in my venture portfolio? And if you have a high degree of certainty on that, then, yeah, you skew your concentration. But you have to have some rule of thumb like that, rather than just, I feel brave, let's do this. So now back to Nevada.
Harry Stebbings
It's a meaningful company. It's been a very prominent startup for last years. Anything notable that you thought about the ipo?
Jason Lemkin
Well, can I ask both of you maybe Rory, first a question on it? Maybe this is a little mean, and I'm a big fan of Ariel and everything they've done. Right. But it feels like to me, and sometimes this is a good IPO strategy is they're going first because, look, Brex just announced and Brex had its slowdown, right? But it just announced it's growing 50% at 700 million. Right. Hard to take everything at ramp. It's a little confusing, but let's assume they're growing that fast. Faster, faster at a billion. Okay. They have to be, mathematically. So if you see them as peers, and we could argue they're not, but I think the markets will. It's number three. So there is an argument that number three should go out now before number one and number two are out and the public markets lose interest. I don't know whether it's true today, but when I've been on the other side of IPOs, there's a strong desire to get if number three is good, right. Or number two is good to get it out before number one.
Rory O'Driscoll
Two things. One is, I think they would say, and in my view, correctly, that while they're in adjacent spaces, Navan is very much trip and travel focused with a small amount of software. Brex is very much card with a small amount of software and payments. Same with Ramp and then Bill, which I was on the board a few years is very much accounts payable with card. So they get lumped in the same thing. But they're actually quite different than most. In advance revenue comes from business the other guys aren't in, which is travel booking. As this thing from Travel Pay.
Jason Lemkin
Almost all of it.
Rory O'Driscoll
Right. Travel booking. So in other words, when I book my flight on the Navan system and I book United, that's the van money. Now, if all I do is pay for a flight on United Airlines with my Brex card, that's Brex money. But their adjacent space is not the same. Just to put that out there, but at the same time. Yeah, but I can see you right when you zoom out a million miles. And when you read their S1 1, they're clearly trying to claim more than just travel because they're truly trying to claim payments. They're trying to claim software based on their claims, which are a little in advance of their reality. You're right. They are in the same market as other two. And if they are, it's pretty damn smart to get out early.
Harry Stebbings
I think that expansion across the horizontal product suite I think is actually behind the rebrand from Trip Actions to Navan, going from vertical specific to horizontal. I agree that Travel Perk, I think are obviously a very direct comparable for them and they are bigger than Travel Perk. I think it's perfect. If I was the board, I'm like, perfect timing. Let's go, go, go. Completely agree with you, but this isn't.
Jason Lemkin
The best time for Navon to ipo. They're not profitable. This isn't the best time. I think they're doing it because of. Listen, I could be wrong and I'm a fan, right? But I think they're doing it because of the competition for IPOs. Otherwise, why not wait another few quarters and get profitable? Because it's not the perfect. I don't think it's the perfect time to ipo.
Harry Stebbings
I don't know. They did if we were sitting on the board together. I would argue with you that Ramp and Braxton not going to go out anytime in the next six months.
Jason Lemkin
But my experiences create that gap. Right? I mean, you could argue that at the lay level, Netscope didn't get much attention because Rubrik is the same but better now it's not the same. Okay, but if you're just comparing security IPOs, Rubik is growing faster with better economics than Net Scope. Why wake me up when you have something better than Rubrik? Wake me up.
Rory O'Driscoll
But you're still getting $7 billion of liquidity. First of all, let's consider this on a standalone basis, getting liquidity and then we'll do the game theory of the other guys. Because those are different questions on the standalone basis. Yeah, you're right. Probably. I can see the pro and the con. It'll probably take more than another year to get profitable. Because if you actually look in the P and L at Navan, they really held OPEX flat to in fact slightly, slightly down this year versus the prior year. And you know, you do that as a board when you're like, you want to throttle the damn thing and make it profitable. So you really push. Remember, inflation's 5% or 4%, so if you're running negative OPEX in real terms, you're really reducing. So this is a company that clearly is straining might and main to get profitable. And you're growing 30%. So you could probably work out based on that. Is it one year or two more years to get profitable?
Jason Lemkin
It's just too long then, right? It's just too long.
Rory O'Driscoll
Yeah. And you say to yourself, I could wait, but this is a pretty damn good market. Do I take a little haircut for and not be profitable yet? But am I done now? Am I public? It's off the to do list. You survived the near death experience four years ago and as we've discussed, we think at the margin public security is just an easier place to be in terms of access to capital on an ongoing basis. So I think it's smarter than. And you're right. So you have that in the abstract. Then you have the game theory side of it, which is it's good to be first maybe, but you definitely don't want to be last. Because the other side of the thing is really hard. Where two other companies get out roughly in your space and you're the third. At that point, unless you are demonstrably better than them, it becomes troubling to get out. Because every public investor says, I already have Brexit and Ramp. Now you're Brexit and Ramp, but not quite as good. Why would I buy you? You don't want to be the last player and the last one out when.
Jason Lemkin
People perceive it as a direct comp. Even if it isn't, if Brexit and Ramp are already public and they're better, I'll just go buy those shares today on E Trade or whatever. Why do I need to do your IPO and listen to your roadshow? Unless there's a mat there has to be a massive discount or why do it?
Rory O'Driscoll
Which would argue for exact. Which argue with what you're saying, Jason, is it might be smart to go now. It might be smart to get the novelty value, it might be smart to take the ground. Maybe you can go public. Maybe you can, I don't know, acquire a second string card payment company and add that to that arrow to your quiver. Much easier to do as a public company. So, yeah, I think it's smart.
Harry Stebbings
Rory, I haven't had IPOs like you IPOs, period. So I have to ask, you always get these newspaper articles that are like, oh, index make $5 billion and big numbers thrown out, but you've got a lockup period, and then as a major investor, you can't sell all in one. How does it actually work? Genuinely, when you are a large shareholder, they ipo. What's that timeline to liquidity?
Rory O'Driscoll
Sure. First of all, yes, it's a totally funny thing, because the other thing, just to put it out there, just say this, is that you tend to report as an investor your holdings. You're the named person on the thing. In SEC filings, it looks as if you own not just your shares, but your partner shares and the LP shares. So suddenly, take the index example at Figma, you can probably Google the partner in index, and they'll say Networked and Figma stock 3 billion. It's totally misleading and results in a whole bunch of charities calling you and saying, please give me some of your 3 billion. And you're like, I don't have 3 billion. I got 20% of 3 billion divided five ways. And it's like six months before the lockup. So, yes, you do get that effect at times. Yeah, look, it's just a process of time. I mean, you have a lockup most of the time. One of the attractions of direct listing is you don't. The lockup is typically six months, and it can be waived earlier. Sometimes you see these performance triggers where if the stock trades above a certain amount, you can waive the lockup early, which is nice. So after that happens, the next thing is. The other thing that sometimes happen is in the lockup period, if the stock performs well, and by performing well, it means trading well above the IPO price, which gets back to this whole thing of IPO pricing. If the stock quote unquote, trades well, you can probably get a secondary done, which means that you can sell more, more of your shares in the lockup period via a registered offering. That's attractive because it's liquidity in a structured deal where you just get your capital and it's One of the reasons why. It's one of the reasons why at the margin, a 10 or 15% pop on the stock isn't, quote, the worst thing in the world. Because everybody who buys at the IPO is happy. And then six months from now, if there's going to be a secondary, you can't get a secondary done if the stocks trade down. If you go public at 14 bucks a share and six months later you're trading at 12 or 10 or 9, it's extremely hard to get a secondary done. Whereas if you were public at 14 and the trades up to 18 or 19 and you make your first quarter, then you can easily get an ipo, a secondary done. That's the second way out. So the end of the lockup win. And then other than a structured secondary, your choice is distribute the shares to your limited partners or sell. And the truth is it takes a lot of time, especially if you're on the board. You have reporting obligations, you have quiet periods where you're not able to sell, and it takes a long time to get out of a position, typically 18 months from the IPO, plus or minus, maybe 24.
Harry Stebbings
Is it not just better to sell before in a pre IPO secondary?
Rory O'Driscoll
No, probably not all the time. Again, you have to have. It gets back to the same two criteria. You have to have an informed opinion on the value of the stock. And then, then you have to figure out your risk tolerance and institutional issues on top of that. To the extent that the median stock pops and then trades up, you'd probably be leaving some money on the table. But there's been times when that's been the right call.
Harry Stebbings
I asked hem on the show, do you believe that you are fundamentally a better manager of public stocks than your LPs? And he said no, no. But we do understand that there's some who have this rule that they have to systematically sell the minute that they're distributed to. In that situation, we will deliberately hold on because we're not saying we're arrogantly better, but they have this systematic rule in certain cases, or ineffective in a lot of cases where actually they need to hold on. I thought that was interesting.
Rory O'Driscoll
And he's boldly correct. Some LPs choose to automatically sell. And the logic is, look, they're inheriting a stock they don't know anything about. The person who knows most about it, which is the GP has elected to distribute it. So there's some signal in that, and it's just not the asset they want to hold. So I get the Logic of the distribution. I get the logic of the rule.
Jason Lemkin
Hold is your best time to trade on, to legally trade on inside information. Though if you're on the board or close to it, it's your best time to trade on that illegal information. By not trading.
Rory O'Driscoll
By not trading.
Jason Lemkin
Yeah. You can hold legally with inside information. It's a privileged position. You can sit on that board and know what's coming next quarter and tell no one and hold. Now you gotta be careful if you distribute or sell. You have to be a little thoughtful about your timing. But you have this special thing where you can hold on inside information.
Rory O'Driscoll
Yeah, right. There's no securities law violation on holding. Equally. Just to say it though, the guy is if you have negative information, you absolutely can't sell. So it's not a one way win street. But you're right. One of the interesting examples, I remember one case of that where on a public company there was on six or nine months where we were in active M and A talks and you'd have your LPs ask you why don't you sell this stock? It seems very fully appreciated. You can't say a word. You just have to say we're taking everything under advisement and you're sitting there knowing we're about to get a 30 or 40% premium once this deal closes. It's a great point, Jason, because sometimes LPs ask, in my view, correctly, what's the advantage of being on the board once you're public? There are disadvantages, but it's not a one way street. The disadvantage is limited trading windows. But the advantages are you do have an inside seat on something like driving to an M and A are an upside outcome and you have a better sense of the company's performance. So it's a toughie. I find you err on the side of getting off reasonably quickly because you do want to get on to the next business. But I don't on the other hand believe in just bailing day one. So I've generally found you get off within 12 to 18 months of the IPO most of the time. And at that point you're distributed, you've done your job. That said, it is worth pointing out that the two venture investors in the Nvidia IPO in 1997, Mark Stevens and Tench Cox of Sequoia, I know, have stayed on that public board to this day. And I believe the board package, as you know, the equity you get as a board member has been extraordinarily, extraordinarily worth their time. Let's just go with that.
Harry Stebbings
And there's one I totally can't remember, so I'm not even going to try. But who's never sold a share?
Rory O'Driscoll
Yeah, I think it's Mark Stevens who never sold a share. Yes, that's good. No, you're probably looking at $1 billion plus maybe many billions of dollars. Being early in the largest market cap company on the planet and never selling any shares turns out to be a remarkably good way to make money.
Jason Lemkin
I think it's impressive. Just like the concentration in Navon. It's just a hit less impressive than it sounds. It's very impressive. Right. But when you're up enough personally, it makes sense to hold your all your winners in the public markets for taxes and other. There's just no reason if you're personally up enough to sell any winner. Right. With all reasons, you might as well let it ride. Right. Unless you're. If you know it's going down, sell it. Right. Yeah, but. But you want to hold on to an asset that will continue to appreciate, essentially tax free. There's a lot of advantages to it. Right.
Rory O'Driscoll
Pointing out that portfolio theory would say something different emotionally. I'm with you. I liked holding on to the companies I'm involved with. Portfolio theory would say something different.
Harry Stebbings
I am not breaking the rules here, but it's a very significant part of our ecosystem. I mean it directly applied to tech. I'm not going into politics, but H1B visas was announced in terms of the $100,000 fee or payment that's needed now for new H1B visas to be granted. So I'm not going to trump or politics for. Do you think this will have a material impact on startups, early stage companies and the teams they built?
Rory O'Driscoll
It will have an impact. It will obviously at the margin be negative because at the margin, immigration has obviously been extremely good for the tech ecosystem. So you can make that as a definitive statement. Materials are a harder thing to assess.
Harry Stebbings
Well, there were 440,000 applications in the last year. They generated between 19 and $120 billion.
Rory O'Driscoll
Of GDP for the U.S. yeah, 70,000 accepted. I think there's 70, 75,000 a year, one or the other. I think at the margin, if you would have any rational immigration strategy and you were to rank all of the people you want to let into your country, STEM graduates who found companies that employ thousands of Americans, would be top of that list. You could argue that some program like the exceptional program we have, which is separate, are the H1BS. Kind of makes sense. You could argue that some increased fee might mitigate some of the arguments against the H1B which as some folks would make, which is that you, some of the applicants are at least doing much simpler work that could be done by folks in the country and therefore, hey, maybe it should be charged more than that. I think the way this has been implemented, the absolute sum, all those things aren't great. And I think the real truth is rational immigration policy for something like this gets caught up in, as you say, a whole swirl of other emotions around wider immigration issues and what it means. It seems to effectively preclude any sensible rational policy for this kind of highly skilled immigration when it's pretty obvious that a rational program like this would be extremely good for the US Anyone that.
Jason Lemkin
Has been doing this for a while that isn't just three kids working996 and SF has had H1B folks on their team. I have, yes, I've had great folks on my team. Especially my first startup, which was hard. It had a material science component. It wouldn't have been possible without H1B. At least on its surface. Okay, I had H1B. I ate two folks with H1BS on my. They were transfers, right? I didn't, I didn't sponsor them. I had on my first team of 10, I had two. Wouldn't have had my first exit or my first startup or saved hundreds of more of lives from my first startup. So for sure, right? And what we want at a meta level is everyone great coming to the U.S. that's what I selfishly want. Every single talented person that can help keep our Nvidia shares high flying coming to this country. I want it selfishly, socially and ethically and personally. But at a very tactical level, we find ways. Okay. The O1 like if you look at the companies you've invested in, they're all O1s now. Okay? Everyone finds a way to get a note. At least all the founders get Owens and oh ones have a lot of cons, right? And you've got to keep them going. And it's stressful, but there's ways. And so I do think the impact will be modest and the big tech companies will just pay up. But I think it's terrible. But I think the impact will be modest at the moment if it doesn't expand. But I've. We've all had great H1BS on our team. It sucks.
Rory O'Driscoll
Exactly the pragmatic point. If you see the strong. I appreciate you saying that, Jed. If you see the strong positive that the program Brings in aggregate. You can say there's a little bit of abuse but it's worth the tax. If you're on the outside and you're incensed by immigration in general, then you ignore the great people who've been enabled by H1BS and you focus on the abuse and you say this is awful. Pick a company Microsoft is using using H1BS while laying off Americans. It's easy to give that speech right. There's no accident that the countries that have the most skills based point system are the countries that have least angst about immigration. $100,000 is kind of a rough American proxy for skills based. In a rational world you do. Let's just remind ourselves what Trump at one point said he'd do which is attach it to every stem degree. You're trying to find some proxy for letting the people who are best for America. That seems to be a reasonable rule because let's be frank, everyone wants to get to America. God knows I did. So you have to have some rule that isn't everybody. So a logical rule is what's good for us. And you could imagine a point system stamp, all that kind of stuff. The money thing is just a very. I think it's trying to be a very crude proxy for that and I think with people being more cooperative you could probably come up with a better scheme than pick a dollar sum and make that the deciding factor.
Harry Stebbings
A final one before we do a Kalshi quick fire. It's just notion hitting 500 million of error I thought was really impressive and accelerating.
Rory O'Driscoll
So okay, I'm going to say it then. They're not trouble trouble double doubling. Right. Is it impressive? I mean I think it's impressive but this is almost a counterpoint to the only thing that matters are things going faster than SaaS. This is a mid sized SaaS company. We excel probably, I don't know 30%.
Harry Stebbings
Why did I think it was impressive? I think, I think it's to Jason's point it's hard to get a re acceleration at scale. I think treble trouble double double is absolutely dead early stages.
Rory O'Driscoll
Agreed.
Harry Stebbings
Trouble, trouble double double at hundreds of millions in revenue is phenomenally impressive to me.
Rory O'Driscoll
Agreed.
Harry Stebbings
And at 500 million in revenue you could actually squint and see my $10 billion stock which I have since it acquired some of my companies reasonably being finally up to the watermark of $10 billion. I'm like 20x. It's a bit punchy but it's a bit punchy with that growth rate.
Jason Lemkin
Those pesky 2021 valuations.
Harry Stebbings
Oh, Jason. $10 billion.
Rory O'Driscoll
Yeah, I mean I think you know.
Jason Lemkin
What it's even talk about it anymore.
Rory O'Driscoll
I mean what it points to is, you know, reports of their death have been greatly exaggerated, as Mr. Twain would say. Right. It turns out these mid tier significant scale SaaS companies, they don't have to just become something totally different, but they have to embrace and lean into the AI trends while still being fundamentally the thing. They are not trying to be a totally different company. You can get re acceleration and I agree with you, I was giving you shit. But you're exactly right. 30% acceleration at $10 million isn't what the paper is written on. But if you're at critical scale, within striking distance of an IPO and you can use an AI enabled story to get you back over 30% plus 40% growth, you have an IPO in your.
Harry Stebbings
Future, they IPO today. Where do they price?
Rory O'Driscoll
Crudely estimating, I don't know if the growth rate, but let's assume it's 30, 40%. I doubt it's really doubling. I could be wrong, but just looking at the head count, they have 1,200 odd people which doesn't get you to doubling based on the growth rate. A 30% grower. I mean Netscope and Navan and. Well, Netscope is priced already. It's 7, 8, 9 times NTM. So something like that. 4 or 5 billion, maybe more if the forward growth rate is a little better or if I'm underestimating the revenue. But yeah, a long way from 20 billion. And it'll be interesting to see how they digest their preference issues. But a great outcome. I mean $5 billion, seven, $8 billion is real money.
Harry Stebbings
No, I know I got in at.
Rory O'Driscoll
10, but Harry, I don't know if it works. That's your problem, not theirs.
Harry Stebbings
It's not my fucking problem. They bought my company. I didn't have a choice.
Jason Lemkin
Well, it's a little bit. I mean it does hang over the heads of most founders, the high valuations, they've compartmentalized it. But it's not, it's a little bit their problem.
Rory O'Driscoll
It is their problem. And as I said, the real question then is how does it get playing that out? How does it get unwound? And we talked about this in the context of a couple of the prior IPOs. I don't think you should stay private just to earn your way back into $20 billion. I think you can go public and then I think it will boil down to you might go public and either the stock gets converted or as we've discussed, the preference remains outstanding until it grows into it. But yeah, I don't think you can hold the rest of the company up just because 5% of the company paid 20 billion pre final one and then promise.
Harry Stebbings
Do you think Airtable will make it back? I got a ton of Airtable from them buying a load of my companies. Again, just help me out, just like help me with my planning.
Rory O'Driscoll
All these companies are going to be priced on the fundamentals. This does go back to maybe a more prosaic version of the Hamad comment, which is stories at the forefront can be priced on sizzle. Stories that are 10 years old are going to be priced on fundamentals. If they have 200 million in revenues growing at 20%, they'll be priced at five or six times. If they have three or 400 million growing at 30 or 40%, they'll get a decent seven or eight multiple. It's hard to get to scale in these markets. You have the dynamic of Microsoft at all times. There was a period of time when all those companies felt euphoric. It felt unbounded for notion, it felt unbounded for airtable. And then a little bit the tide went out of the productivity tools market a little bit. Microsoft just started grinding away at everybody as they've done in so many other markets. And then the world's moved on to AI. So now these are perfectly good companies that are just going to have to find fundamental value based on revenue multiples and even, God forbid, free cash flow.
Jason Lemkin
Just like there was a time when you weren't allowed to Talk about Web 1.0 anymore. It just didn't matter. I think we can't talk about 2021 valuations anymore. It's time to, it's time to just flush them down the toilet. I wrote down everything, I guess a year and a half ago, whatever that I wrote every, everything that had a hint of froth. I have one deal I'm still carrying myself right, because it's over 300 million in revenue and growing. I'm holding it as 2020, but I'm marking it down this year and it's time to just forget about those valuations. It's just, just forget, just pretend they, you know, maybe you can't pretend mark them down even if they're personal and just forget about them because it's too far in the past now four years. Like it's time to move on from those decocorns of 2021. I mean, Klarna was what? 40 billion. Time to move on. Time to time to move on.
Rory O'Driscoll
Its peak was 45, which SoftBank did. Sequoia brilliantly did the round at 5 or 6 and obviously 2 or 3x that. And I think overall 7x the overall investment.
Jason Lemkin
I think we're not allowed to talk about these rounds anymore. We're getting it, but we're getting at the end of this year, this is your last. You've got 90 days left to kvetch and complain about your 2021 valuations. And on January 1, 2026, no one is allowed to talk about their 2021 valuations.
Rory O'Driscoll
We're not talking about your 21 valuations, Jason, is that we seem to be determined to make exactly the same mistakes in 2025.
Jason Lemkin
Yeah. We need the Runway to make them again, Rory. We need to find, focus on making the same mistakes again and not be hampered by them in the past.
Harry Stebbings
I'm seeing less diligence now than I did in 21.
Jason Lemkin
On any hot air, there is no diligence provided nor is any done right. It's just done on Saturday. Why would you do diligence? All you can lose is one extra money. Why would you do diligence again?
Rory O'Driscoll
You can say what you. As long as you don't put this quote on the. Out on the My name, Harry, I'm happy again to be the boring guy here. We're finding that what you have to do is you have to do your due diligence prior, but you have to come to the table with what would informed opinion which you can either pull out of your ass or try and do some pre work.
Harry Stebbings
One of my companies had a term sheet pulled. This is a large company doing a lot of revenue from a tier one firm. And what I found more and more is just to kind of get the exclusivity and to lock the deal down. They'll term sheet it and then for deep work they're like, I'll do it after, in the 30 day closing period. And then they put this is a really bad trait of an increasingly competitive.
Jason Lemkin
I'm less critical of it now than I was all the prior years of my career. I'm less critical of it. No, I know, but here's the, here's my view, Harry. If you're only giving me a Saturday afternoon to make a decision, if you're giving me one hour, you won't share any data. A lot of these contracts are paid pilots. You're not disclosing anything and you want me to make a decision in Five minutes either. It better be effing solid. Okay? And if immediately after that term sheet, I see 10 things that aren't true and you want me to not rescind my term sheet, you better let me dig in here. Because the level of trust that you have to have to do a deal on a Saturday is. It's under discussed. It is mocked by many, including leading accelerators, but there is a high degree of trust involved in this. So again, if you want people to make a decision in five minutes, you better be on the up and up. And so I used to be critical of it here. I used to think it was holding my place. And. And it still happens. Like, that's your point. It happens. It's bad practice. But I have a lot more empathy than I've done the last decade. I have a lot more empathy in 2025.
Harry Stebbings
Or just. Or just do what we do, which is say if you want that decision timeline. That's not our type of deal. Sorry, we're not going to engage.
Jason Lemkin
Yeah, but I think many of the best companies don't provide that. That flexibility today. Now, the best founders wind them up, right? Give them breadcrumbs and give them data ahead of time, right? If you want a big check, you got to do that. But when they' it's one day, dude, you can say no, Harry, but you're an aggressive investor. You're going to say yes to a couple. I'll bet you that Saster tattoo you're going to break your rule a couple times. But it's the right. It's the right response, right?
Harry Stebbings
Dude, I'll get a Sassa tattoo if Rory gets one.
Rory O'Driscoll
Well, then you're fine. I plan to die with my body unblemished with tattoos.
Jason Lemkin
It's not just being founder friendly. We all want. Anyone that's been a founder wants to be founder friendly, right? I want it to be an extreme, but not allowing diligence. For all intents and purposes, you're running a risk.
Harry Stebbings
Jason, have you got less founder friendly, less founder friendly?
Jason Lemkin
I am more founder friendly, but it is less appreciated. By far, I am the most founder friendly I've ever been in my career. And I get less. I catch more crap for it. Everyone says great job and everyone's jostling behind the table and everyone's manipulative and I'm the whole only. And yeah, poor Jason. No, you asked. Well, you asked the question. Founder friendly is. Is bullshitty as pulling the term sheets in 2025. It's as bull. It's Both Founder friendly has become bullshit. But it's table stakes. It's table stakes. To get into the deal, you got to be founder friendly, right? Founder friendly is writing the check when no one else does. That's founder friendly. Founder friendly is when no one else is there at the board meeting anymore and you're there and you still have a W on the other side of it. That's founder friendly. Founder friendly is when you actually recruit the executive for the role, not just say, who you looking for? I'll send it to my talent person and do nothing. These are things that are founder friendly, right? Not saying great job no matter how you do.
Rory O'Driscoll
I find myself oddly agreeing with much of that. I mean, what I've internalized is in the game of founder friendly, it's not a winnable game. So what I say I'm trying to be is founder honest. I want to be founder honest, which is I want to tell you exactly what I think, which I think is more useful than great job if it's not doing a great job. And I think you're right, Jason. The only way to judge who really is founder friendly is how they behave. In a tough deal. There's no information on how you're doing a good time. Right. And I've just internalized that. Most people don't check that. And that's just the way it is right now. So it just becomes this meaning you end up with this meaningless trying to prove something in a bull market that you really only will demonstrate in a bear. But that's okay.
Harry Stebbings
I am just going to say this before we do a Kalshi quick follow up, because Jason won't. But I always remember the revenue cap founders telling me about Jason, like wiring the money from his personal account. And it's just like, whoa.
Rory O'Driscoll
I remember that it was the SVB weekend. We were literally on Sunday having a partnership call, doing a whip around to say who could cover which companies when. Yes, when the recap came in and the US government stepped up. But yeah, it was interesting who you only know what people are like in a tough deal. It's also true, by the way, on VCs, you can only decide which VCs you really like when you've been to a tough deal with them. Because then you know we're gonna do.
Harry Stebbings
A Cauchy quick fire. So bet us on when will a final TikTok deal be reached between the US and China. Come on, Rory, you love this round.
Rory O'Driscoll
I hate this round, as you know. But I'm gonna vote for never. Cause it's just so much fun for the big guy to keep dangling it. This is the I mean I'm being slightly glib here, but planning to do the TikTok deal has been the most fun anyone's ever had because you have favorite favors to troll people, et cetera, et cetera. I'm sure it'll get done at some point, but it's not knowable by me.
Jason Lemkin
Jason Look, I I obviously there's a lot of complexity here, right? But, but I'm going to say the next 60 days the the definitely somewhat toxic H1B stuff this is a lot of tariff posturing too to get these deals with China and India just done and I think they're going to get done and so whatever this crazy deal is, it's going to get signed in the next 60 I think these deals are going to get done this calendar year and I think it's going to get signed and I think hopefully this H1B thing kind of diffuses too because now it's not for existing Everyone had to friggin fly back in 24 hours right now you don't have to do that and a lot of these things may kind of evaporate as the tariffs get resolved. So I'm betting 60 days matter smart.
Harry Stebbings
Glasses Another fail for VR or mega success?
Jason Lemkin
0% chance there is success. What's the beta?
Harry Stebbings
Wow.
Jason Lemkin
Why Because I owns like eight pairs of the existing ones because we just don't need to play Tron in our eyes. We just don't need a seventh screen. It's another solution in search of a problem. In my in my opinion we just don't there's just only so many times I need to be on the podcast with Harry looking at my notes in the size of my like 11 inch thick gen 1 new ones. It's not a huge problem. In the real world I'm having fun. I'm watching what Johnny Ives from his new 70 million dollar tip run Peter Terry just bought with his with his shares to add to all of Jackson Square. I'm because I think he's going to come up with something disruptive and I think it's fascinating because it's such a hard problem. We just don't need an only so many of us want to wear two smartwatches like there's just certain it was hard enough to get the smart like changing this paradigm has been tough in tech so and a lot of venture dollars will go into it per Harry in the real world we leave them.
Harry Stebbings
On the shelf Final one Will Atlassian's buying spree payoff? They've got dx, they've got smaller ones cycle born, they just going and going and going on the M and A. Will it pay off and make them an AI leader again or not?
Rory O'Driscoll
It'll help. Look, it's not going to make them quote an AI leader. They don't have to claim AI dominance all they have to do is move their existing customers into a AI engineering management world then the browser based things separately and just try and stay vaguely relevant and defend the market cap and you know grow the business 20% if that's what leading is then maybe if it's. Do I think it's going to make them the AI dominant coding agent? No, but just trying to move the needle on a 4 billion revenue, 40 billion market cap company.
Jason Lemkin
No, it's not enough. You got to put chips into play and I think, I think it's just baby steps. I also thought, you know I look for these signs like what, what Sam Altman saying, right. The other thing on the DX1 I looked at, these are not easy jobs like Michael Cannon Brooks has right? These are not easy jobs and the PR pictures of him on the deal were him just alone. It wasn't even with the DX founders. This is lonely picture of Michael and I just thought man this is a tough job in the. I mean he has one of the great iconic properties of all time right in sort of you know somewhat developer focused B2B software but it ain't it just the lonely mike in these pictures I'm like man this stuff's hard. So if this was going to change Atlassian and they'd be together toasting rather than the wartime mike picture. So I think it's a start and dilution aside or I don't know I should know whether they did it with cash or stock. You know make the bets. I don't think this is going to change the face of the company.
Harry Stebbings
Guys listen, thank you so much for doing this as always as you can tell we have so much fun doing that show but I want to make it the best show for you. So let me know what we can do to make it better for you. Harry0vc com I want to hear your feedback but before we leave you today let's talk about agents. Specifically Piper the AI SDR agent brought to you by qualified. The agentic marketing era has arrived and if you're a B2B marketing leader looking to scale a pipeline generation Piper the AI SDR agent. Wow, it is here to help. Piper is the number one AI SDR agent on the market, according to G2. And hundreds of companies like Box, Asana and Brex have hired Piper to autonomously grow inbound pipeline. Fucking sign me up anyway. Qualified customers see massive business impact with Piper. 3x increase in meetings booked and 2x increase in pipeline. Wow, that is some results. Hire Piper the 1 AI SDR agent and grow your pipeline today. Learn more@qualified.com 20VC that's qualified.com 20VC with the 20VC spelled out in letters for for goodness sake. And while Piper builds your pipeline, Attio gives you the CRM power to close and grow those relationships. Attio is the next generation of CRM built for the AI era. Fast, flexible and powerful. No, it's not a sports car, it's a CRM system, baby. It is Attio and it takes less than a minute. Sync your email, your calendar and you'll instantly get all your relationships enriched in real time with incredible data, no manual input needed. Attio also integrates with your existing tools tools and syncs with your product data to deliver an AI native platform that's tailored to how your team actually works. You can model your CRM around your business, automate complex tasks and surface real time insights all in a platform designed to scale with you. With Attio, AI isn't just a feature. No no, it is the foundation. It's powerful. It's AI automations, it's research agents that transform your go to market motion. It's a data driven engine from intelligent pipeline tracking to smarter product LED growth. Fast growing startups like Flatfile, Replicate and Modle are all experiencing what's next. So get ready to build without limits and start now. Attio.com20VC and get 15% off your first year. That's attioattio.com20VC. Okay, pipeline sorted. Woohoo. Now what about your own legal team? Enter Logora. Lagora is the category defining AI platform that's fundamentally reshaping how legal work gets done about frickin time. Empowering lawyers across tier one law firms and in house teams to achieve more with greater precision and confidence. Ligura does this by solving really concrete tasks such as document extraction, reviews against a firm playbook and suggesting well crafted markups directly in Microsoft Word based on your preferences. My word, that is a topic list of conversation that will not get a second date. But anyway, the adoption of legal AI is surging across the world and Lagora is at the forefront of this shift as the chosen partner to 250 industry leaders in law across more than 20 markets. The likes of Goodwin, Bird and Bird and Deloitte are making daily use of Ligora platform to review and research with Precision, Draft Smarter and collaborate seamlessly. They recently also got an $80 million Series B from Iconic. They're backed by General Catalyst, Redpoint, Benchmark, and YC All. Also, they operate out of New York, London, Stockholm. Yes, they're Swedes. Always a wonderful race. With over 100 employees from some of the world's leading global law firms and tech companies, the team is growing super rapidly. They're just freaking awesome. Just go use Legora. Honestly, I love Max, their founder. He's just a great dude. Go find out more.
Episode Title: 20VC: NVIDIA Invests $100BN Into OpenAI | Is Triple, Triple, Double, Double Dead | Navan Files to go Public & Notion Hits $500M ARR | The Impact of H1B Visas on Startups in the US
Host: Harry Stebbings
Guests: Jason Lemkin, Rory O’Driscoll
Release Date: September 25, 2025
This lively episode tackles seismic shifts in the venture and tech ecosystem: NVIDIA’s $100B investment into OpenAI, mega-capital cycles in Silicon Valley, the supposed death of the “triple, triple, double, double” SaaS growth model, major startup milestones (Notion’s $500M ARR, Navan’s IPO), and the policy impact of new H1B visa rules. With Harry Stebbings at the helm, joined by seasoned investors Jason Lemkin and Rory O’Driscoll, the discussion is fast, candid, and deep. They blend macro-perspectives with on-the-ground anecdotes, offering both statistical perspective and colorful war stories from decades in the business.
Infinite Money Loop?
Capital, Risk, and Scaling Law Bets
Monopoly & Market Dynamics
Dot-com Parallels and Differences
Stock Buybacks and Corporate Behavior
Signs of Froth
Venture Capital is “Splitting”
Is “Triple, Triple, Double, Double” Dead?
What Counts as a “Good” Exit?
When to Sell?
Navan’s IPO & Concentration Risk
Notion Hitting $500M ARR
Diligence is Out the Window
Founder-Friendly: Real or Table Stakes?
TikTok/China Deal:
VR/AR Glasses:
Atlassian’s M&A as AI Play:
On Monopoly Risk
“This is an epic monopoly like we’ve never seen... ChatGPT already dominates our lives. It’s a Standard Oil of tech.”
— Jason Lemkin, (10:50)
On Market Fragility
“The market cap of the largest company on the planet is on the spending decisions of six or seven people... All six are determined to spend themselves into oblivion to win the prize. It’s a fascinating game.”
— Rory O’Driscoll, (12:56)
On Venture Returns
“Turning a fund returner into a 2x fund returner is a BFD. It’s such a big deal for carry, for performance... It’s a nice but stressful position to have.”
— Jason Lemkin, (35:02)
On Risk Aversion
“Most of us have a risk aversion of about 2... Some people... are just totally maximizing expected return. They just want to make the bet. SBF had the same thing. Some people just... have super high risk tolerance.”
— Rory O’Driscoll, (36:31)
On 2021 Valuations
“We can’t talk about 2021 valuations anymore... It’s time to just flush them down the toilet.”
— Jason Lemkin, (65:34)
On Founder-Friendly Myth
“Founder friendly is writing the check when no one else does... These are things that are founder friendly, right? Not saying, ‘great job’ no matter how you do.”
— Jason Lemkin, (69:42)
This episode offers a window into how the world’s leading VCs are thinking about the new AI-capital cycle, shifting investment strategies, and what level of growth and product excellence is required to break through the noise in today’s overheated—or depending on your stage, still selectively rational—tech market.