20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

25:05And it's just been unwound. And the pop was because, oh my God, you signed all this revenue and everyone gets really excited about the RPO. That was like 40, maybe 50, I don't know, 60, 90, 90 days ago, probably last quarter's announcement. And now everyone's like, oh my God, to meet this revenue obligation, you're going to have to incur a whole lot of expenses. Well, shock horror, you just opted to enter a very capital intensive, physical data center building business to service one or two super large customers, principally open AI. It's a tough business. And now I think people are internalizing that.

25:38The stock is probably is now below where it was. In fact, I know it is. It's I think 15 % below it was just before they announced all the quote unquote good news. To me, it was fun to imagine my real sentiment here was I knew it and I should have done those shorts. I should have bought those puts. In retrospect, 90 days ago, we were right. It's a sugar high, a total sugar high on a huge contract with someone who may or may not be able to afford to pay for it. That's OpenAI. And even if they can afford to pay for it, it's not a great business because it's capital intensive and not nearly as good as your existing free capital positive business.

26:14So you'd say that it's returned to a normal, it's not going to rebound from here? No. That's not what I think. No. Oh, you do. Go for it. I think it sounds odd, but let's bring Oracle and CoreWeave in together. I think they are very interesting. And if you look at the leaders, they're the weak guys, okay? They don't really own anything themselves. They're at high risk of margin compression. so the market's gonna have jitters between now and an even bigger ai future we've talked about it's gonna have ups and downs it's gonna have bumps and it makes sense oracle down 46 since september right core we've down 60 from its high in july it makes sense those should be have the strong they should see the biggest impact from bumps and there's no reason actually listen i'm not saying that that these are even the best companies we've ever had but there's no reason I don't think they will rebound as the overall trends.

27:04I think these are just jitters. The overall trend, I think, is still, we're still anti-gravity here. And that's the key question. First of all, I wouldn't do a nigger shot, I'd do a putt. But yes, which is the coward's way out. But you're right. I mean, you're exactly right. These companies become the high octane bet on AI. If you think it's going to go up, you buy Google, you get 20 % appreciation. But if you buy CoreWeave and you're right, you could get a double. You're right. So they are the highly amplified bet because they are the marginal provider of the commodity. And they have no other businesses to diversify.

27:37They have no IP. Well, Oracle has others, but they have no IP here, right? I agree with your characterization. So I suppose to take your point, Jason, if you think the CapEx cycle has two more years of strong legs, then you can see these guys rebound. And if you think we may have found an equilibrium, but there's not much more increase up from here. notice the marginal investment rate's going to go down from here, then you're right. Then you would be scared of owning them. That's exactly it. It's an easy way to figure out what's going on at the margin in the AI space and at the margins where the money's made.

28:10This was my question. Is this like a micro market hiccup, small undulation that we pass over, or is it a canary in the coal mine that's foreshadowing something much bigger to come next year? It doesn't have to be something bigger to come. I always think the markets, They're old. It's like this person always interrogating you for truth. You know, the markets are always trying to find out what's true, what's true. Should you really be spending this money? Right. You could argue right now the market is the market six months ago was saying everyone should be spending money on AI. And that's great.

28:40Now the market's saying Gemini, Google, you keep going. You got a plan. Microsoft would like to see more of a plan. But yeah, you got this thing. Open AI, we're good for it. We'll give you$40 billion. Facebook, not so in love. And then CoreWeave and Oracle, you guys, it's not clear to me why you're doing it. So it's doing a good job of kind of filtering through from the overall mega trend, which is amazing, to which of the guys have a good plan in this space and which of the guys do not. So there is a world to answer your question, Harry, where what happens next year is Google still continues to invest in more capex than before, which increases overall demand.

29:13But some of these marginal players maybe can't be as aggressive as they've been. Neither the end of the world nor a rebound is a totally plausible scenario. That's why me and Jason have bigger social media brands than you, my friend. Because we're great at binary statements. In the middle. You're so right. The world is full of in the middle and no one wants to hear it. By the way, that might explain a lot of our problems in the wider society with social media. But we'll come back to that another time. Broadcom was another one. Lost$300 billion in market cap in 48 hours. Investors being concerned a$21 billion order from Anthropic will drag down the margins, higher costs in the chips business.

29:55Is this a reasonable concern? An order from Anthropic seems like a fairly securitized asset to back. Is this a reasonable concern? And a$300 billion loss in market cap seems like an exaggeration. I don't think it's unreasonable. in the following sense. Is that one, Broadcom's an amazing story. Just an amazing story. You look at what a guy's achieved over the last 10 years. It's stunning. It's current market cap plus or minus 1.6 trillion. As a reminder, the first trillion dollar market cap company was Apple in 2018. And now Broadcom, a company 90 % of people couldn't even name or tell what it does, has a 1.6 trillion market cap, even after this correction.

30:34And I think it's trading at high teens in terms of sales multiple. So it's not like it's cheap. It totally makes sense that the Entropic order, it's actually, it's similar to the OpenA Oracle discussion. Why is Entropic buying chips from Broadcom? Answer, they don't want to pay 75 % gross margins to NVIDIA. So it totally makes sense. And so they designed this other chip and they say, hey, dude, I'll buy this chip from you, but I'm not going to give you quite as much money as I'm giving NVIDIA. Because if I'm going to pay full retail, I might as well go buy the designer brand. The whole point is this is meant to be Kohl's here, dude.

31:06You're meant to get lower gross margin. So it just makes sense that it's a really good business. They'll make good coin at it. But it's not going to have quite the same margins and defensibility that you'd expect NVIDIA to have where they're imposing their architecture on their customers. Broadcam is being kind of a made-to-order business. They're saying, Mr. Customer, Mr. Entropic, tell me what kind of chip you want and we'll make it, we'll design it, et cetera. But it's not the same as marketing a branded product like the NVIDIA Blackwell or whatever it is. I think, again, it's the same thing.

31:38The markets just got a little bit ahead of themselves. When you type in the revenue number, you get all excited. When you type in the EPS number, you get a little less excited. And it's just this process of discovery. It's just stunning that you can drop$300 billion in a single day and still be worth$1.6 billion. Let me tell you what a real crash is like. When you're still trading at high teens, sales multiple, it's not like everything went cheap, Harry. It's just slightly less expensive. It is interesting you lose so much over guiding 100 basis points lower. What's really interesting, and I'm not smart enough to fully predict this, who gets a pass on gross margins and who doesn't?

32:13If you're a Broadcom or someone, you're not getting any pass, even though you're getting massive AI spend. We're very worried. All we care about is we're worried you're gonna lose insane profitability in the semiconductor industry due to AI. Oracle got this great pass until it didn't. CoreWeb gets apparently an entire pass. OpenAI does, Meta doesn't. I can't keep up with who gets the gross margin pass. All I know is we learned in Palantir, some folks deserve the pass, and then we're going to find out some don't deserve a gross margin pass. I don't know. Rory, you said it's not a crash, and it can get much worse, and it can go much lower.

32:49Markets are at the same peaks as 2000 and 2021. Apollo predicted zero public equity returns in the coming years. How did you read that, Rory? Sure. I think you have to be very precise in what Apollo said. They said the predicted 10-year return is zero. And this is a piece of work that's fairly well understood. And it's actually a very important piece. It's probably one of the things I look at most. Vanguard send it to you. They're really good about that. They basically show a correlation between entry PE and subsequent 10-year return. And they show three graphs. They show your one-year return.

33:23There's little or no correlation. In other words, when you buy at a high price, it can still go higher. The correlation gets stronger for five years. and it's strongest at 10. In other words, if you buy at a high price, I can't tell you how you'll do next year. Maybe the stocks will keep going up and you'll feel smart. But what I can tell you for sure is the probability of making money over 10 years is very correlated to your entry price. And that's the graph that Apollo showed. Because what they're doing, and it's what all the sensible investment houses and asset managers do, they don't make one-year predictions because you can look like an idiot.

33:58And it's hard to know. I mean, it's not just do you look like an idiot. It's actually empirically hard to know. But you can say with a high level of certainty that if you buy at a PE that's 50, 60, 70 % higher than the long-term average, your forecast return will be significantly lower. Going back to 99, 2000, you see the same thing. You could have said things were expensive in 96. And Greenspan said they were expensive. That's when he gave his irrational exuberance. But shit kept going up for three more years. You can't predict the short term. But what was true is by the time you were piling in in 99, it took 10 years for the overall stock market to get back.

34:33So you did go zero for 10 years. And even more impressively, and this is a really amazing fact, Cisco, the darling of 99, just got back this week to its 99 stock price. So in other words, if you buy the hyper expensive company at just the wrong time, it takes 25 years to earn it back. That's a compelling statistic. And I think it speaks to the same thing as the Apollo comment. Now, the interesting thing is, what do you do with that information? I know over the next 10 years, you're screwed, but it might go up next year. Do you stay in? Do you go out and risk having a 96 moment where you leave three more years?

35:08I mean, I think you actually end up just, you look at your overall asset allocation, but I don't think you go binary on it because you do have that thing of it's not predictive in the short term, but it is a warning sign. There's a reason that nice Mr. Buffett has piled up$300 billion in cash because he reads these data too, and he understands them better than most. The meta point to make that kind of goes back to our business, because we're not public market investors, is when you look at all these private valuations that look attractive relative to the public, and they do, you have to say to yourself, they look attractive relative to a public market that it's all time high.

35:39And a more normalized public market might well leave some of these private valuations somewhat high and dry. Now, growth might save you. In a nice story, if the Apollo graph is correct, and you just get zero return for the next 10 years, and that's not traumatic. That's not the way life and markets work. What tends to happen is at one point in the next two or three years, things drop 30 % and then you crawl back slowly over the rest of the decade. If that happens, then some of these private valuations that are comped off that could feel lofty. We mentioned Broadcom's dip on the back of many respects, but one of them being Anthropic.

36:13Anthropic announced they're launching an AI coding tool for designers. Jason, I'm super intrigued to hear your thoughts on this. So it's a UI inside the cursor browser lets you tweet web apps, drag and drop, CSS. It's really the first move kind of up the stack, so to speak, for them. Jason, is this the first credible threat to Figma's position where design decisions start? You mean, well, you mean cursor doing it, right? Not anthropic, right? Sorry, cursor. Well, maybe. I think all of us need to be hyper aware of in 26 and 27 is massive convergence of categories. It's not just the old days of seven years later, Datadog would decide to compete with PagerDuty, which certainly hurt them.

36:54That's how we grew up. Like a couple of years would go by, you know, all of a sudden now, you know, Brex is competing with its partners rather than partnering with that. That's the old school. AI is creating convergence where the same products can do more things. I'll give you an example and then I'll talk about Cursor because you asked. It's already happened in e-commerce, which I can see, which is that marketing, sales and support have already converged. This last week too, Andrew Bilecki, the CEO of Klaviyo brought on the ex-co-CEO of Workday to run most of Klaviyo, right? Which is at 1.3 billion growing 30 % because the entire world of e-commerce software has changed.

37:29So he needs to get back to product full-time because in 2026, 2026, there will be no such thing as marketing software that got Klaviyo public. Marketing sales support have already converged to one agent. So it's already happening there. It's actually surprising it's taking a full 12 months to happen in coding. It's a lot of time because if you've built any apps like I have, the disconnect between design and the output, it's the most jarring thing when you get good at something. When you get a good at Repplet like I am or Cursor or whatever, you can build such cool stuff and you're like, man, the design, it all looks like frigging Claude artifacts.

38:03They all look like Claude. Like I can find a vibe coded site and like 30 % of the last YC class looked vibe coded to me. I could see the Claude artifacts all over their homepage. So it kind of breaks your heart. So the fact it honestly took this long as a surprise. So should Cursor own that or Figma should own that or someone new? They're all going to converge. You shouldn't have different tools for design, prototyping, and production. The agents are just too good. And to put differently, what I've learned is we all want to talk to the same agent, designers, product people, engineers, DevOps. In an ideal world, there's this meta agent where we all can collaborate and work together as one company, not us all being on 11 different AIs.

38:43There's a lot of fracturing in AI. I don't know who will win. And it's probably mean to say Figma feels behind, but it is how it feels as we record. Figma is tiptoeing into VibeCoding, just like Canva and others. And there is some disruption risk that the tiptoe is too slow. I think that's awesome, Jason. That insight on the, I mean, because I want to do the coding Figma thing, but also the bigger commandant wanting the single agent for everything. That's just a huge insight because it's only become obvious to me in the last few months as I've been talking to companies. No matter how hard you try, you try and translate your prior experience into this.

39:16You have a sales SaaS company, so now you have an AI SaaS company, sales company. You have a SaaS marketing company, so now is there an AI marketing company? And I think you're right. On a lot of these processes, the reason you have these separate siloed companies is the humans were siloed. There was a salesperson and a marketing person. But if the AI is doing everything, let's just take the customer journey. You can have a single AI agent within your company dealing with your customers as you're prospecting them, as you're selling them, and as your customer supporting them after they onboard.

39:47And I've seen some companies doing that. And I'm like, wow, that's a powerful idea. Because if you think about it, one of the shittiest things about dealing with any company is you start off with sales and you build this rapport and they seem to know exactly what you want. And then you just get transitioned to a totally different person and you start again. And it's like you as the customer are being put through that. It's not okay in the age of AI. And I got to tell you, really, I'm thinking of a couple of deals I sold within the last week where what you expressed is suddenly going, you're exactly right.

40:14The single view of the customer on the customer side. So I just think that's a really powerful 2026 theme. I don't even know what it means in terms of what kind of apps are built. And I'm thinking of sales and marketing at this point. It will come to Figment Cursor in a second. But I just want to say you nailed it there. Rory, can I ask, how does that shape your thoughts when you look at investing in support tools as you have done in the past? I think all these companies are going to expand their footprint. I think going back to the thing, the good news is there's a huge return on ROI on AI. And I do believe there is.

40:43And the bad news is, I think to grab that return over time, you're going to have to be more expansive and aggressive. And you're going to be going into adjacencies much more so than in the past. It's only obvious to me now that I've started to think about it is that if you were selling software to automate work, then you probably sold to each department that did that work. But if you're selling software, AI software to automate an outcome, just sell to the customer. The person wants the outcome and they'll be like, yeah, I'll take all that. So I think you're right. We have an investment in customers.

41:15We have a number of investments in AI sales stack. I just think over the next one to three years, there's going to be mass convergence. just like to kind of jump back to Jason's example in the same way. If there's one, you know, the old line is in any company that you are to selling stuff or making stuff. Well, we just talked about the selling stuff people, but then Jason was talking about the making stuff people, the making stuff people between design and production. I think what he's saying there too is you could argue that instead of having a separate design function and a coding function, I think what you're saying is, does that all come together over time?

41:48Is that right, Jason? I don't, I think we're going to have designers. I don't think we're going to have multiple platforms. It's better if they're the same. It's so much faster, so much more efficient. I have invested in a small startup called Alloy app that sort of bridges it. It lets you vibe code your existing product and change it. And I mean, it's early. There's already insane demand, but that's just the first step. Everyone loves Figma. Every designer. I mean, I'm sure some are grouchy, but I think it's up there with Klaviyo. Everyone in e-commerce, their favorite app is Klaviyo because it just gets you more customers.

42:18Klaviyo's brought in a co-CEO because their whole business model has changed. It's going to be there in software in a year. It just doesn't make sense to have to wait days for designs to change. And then they only sort of work in my code base. And then I've got to integrate it. All these guys added a design mode with Google 3 Pro or whatever it is. They all added a design mode. It's pretty good, but it's still recycled stuff. But you could see a hint of it where now you can make a somewhat beautiful website while you vibe code. 2026 is going to be at 50x better. Jason, you're so well informed on this.

42:52If we take that view then of the kind of collapsing of it all into one platform and one location, if that is the outcome, if I pressed you on saying who the winner of that will be then, who will that be? Will that be a cursor? Will that be a claw code? Will that be a Figma? Honestly, and I know this sounds, Captain, obvious. I honestly think it's going to be who wants it the most. You almost have to work so hard. You have to 12-12-9. as hard as we're working at cursor and it's been great we might have to work even harder but maybe figma works even harder i know this sounds silly but everyone can copy each other in weeks now not in months or years or quarters it's who really really wills it into existence i don't think we can sit back as vcs and just even with our king great king making checkbooks i don't think we can fully control the outcome i think the ones that work that produce 10 times more output are honestly the ones that are going to win, the leaders.

43:45I don't think we can predict. It's easy to bet in favor of Cursor over Figma because Figma took, what, a decade to get to a billion? And Cursor took, you know, a year. So if we're momentum bettors, we have to bet Cursor, right? Even though there's reasons to bet against it, right? They're not designers. They don't have the base. They don't have the customers. But if I had to pick, I would bet on that rapidity today. Is this the interim step to Cursor moving down further or up, whichever way you want to take it, into consumers and into lovable and replic zone it could be i think the only reason cursor didn't build repler lovable is it wasn't worth their time because they're in an even bigger better market for the moment agreed i honestly think it was just a distraction as big as that market is is exciting that those guys together will go to almost 500 million in a year cursor got there in nine months so you you're taking your eye off the ball to invest in a high churn friction full space when they probably have 160 effective nrr at a revenue level because nobody leaves cursor right why would you invest in a smaller high-churn space when you have insane retention and you're growing even faster.

44:47It's just you'd have to, and you want to have a team of triple-digit number of employees. And just intrinsically, the budget for software teams building professional enterprise-grade software is just logically larger than for demo apps or prosumer apps. So maybe there's more individual users of a lovable, or a rep that's kind of in the middle. But the reality is you're accessing the big dollar spend of every software company and every enterprise company when you're cursor. I don't think that the Figma market and the cursor market fully converge. The equivalent now of a Figma design is, in fact, someone using Replit are lovable to do a direct mock-up, an interactive mock-up versus just a design mock-up.

45:29But there's clearly between them all, there's this kind of smushing together. And that's just really significant because what were separate markets are all, they're all going to be competing with each other because the prize is just so big. And, you know, I thought, Jason, you did a nice blog post. Well, I don't know if you did it or your AI machine did it, but, you know, making the point that citing the Menlo work, which is really nice that, you know, 50, 60 % of all the end user spend on AI right now is coding and coding related. Yep. This is the big kahuna. Everything else, even customer support, all the other stuff is everything else to a rounding error is 45%.

46:03software and coding related stuff is 55 % of all enterprise end user spend. This is the epicenter of the enterprise AI revolution right now. 55 % of AI spend is encoding. What will it be in three years? You hope the other categories are just behind in a sense, right? But maybe it's intrinsic to the extreme value, right? In a very large category of software. Yeah, I don't know. But how about this answer? I can give you, I don't know the answer to that question. I can give you a quick answer to an adjacent question, which is fun, is that the total spend is kind of 15 or 16 billion on apps and another 15 billion on plus or minus on enterprise infrastructure, which I don't fully understand what I can't agree with, but leave that by the by.

46:46So the big aha again is end users in the enterprises are spending about, per the mental data, 15, 16 billion dollars on AI, and the people who make AI are spending 400 billion dollars on quote making AI. If that's $16 billion 3 or 4x last year, it's got a 3 or 4x a bunch more times before it can cover the nut on the CapEx spend. To me, that's the most important. I'm less clear on what the mix will be, but somehow enterprises have to find not$15 billion, but$150 billion of budget. Otherwise, the people investing$150 billion in CapEx are going to have a sad day when their CapEx is greater than the revenue line.

47:26So I think the overall growth is the key question. Could I just go back to one point on Cursor versus Figma? Because I do think it's so important to founders and investors. I think one risk is that Cursor completely displaced Figma. We don't need it. That's unlikely for a lot of reasons. I think the bigger risk for so many vendors is that it maims Figma. What does that mean, Jason? The old customers don't leave, okay? HubSpot and Box and even Anthropic using it. They don't leave. They renew. They don't buy as many seats, right? Because the team is also using Cursor. But of course, they don't churn.

47:57the logo retention remains good, but NRR drifts down and new customers, the next generation, the kids from YC, they defer that purchase because they're doing enough in cursor. And I'm seeing this across my older portfolio that folks are maimed, like the existing retention's good, but the new guys are just taking enough of the new budget that your growth materially decreases. I think this is a risk for almost everyone that's established is you just get maimed. You don't get killed, you get maimed. And Kursler could easily maim this market, it's so big. I think of the Holy Grail movie where it's just a flesh wound.

48:32Sorry. It's a deep one, though. It's the one that never quite heals. And you sit in the board meeting, and you're like, well, we had 15 ,000 customers last quarter, Rory, now we have 15 ,200. Hooray. Kudos. Low growth is miserable. Agreed. But it's this maiming that I think people aren't, a lot of founders aren't being honest about how they're being maimed by AI leaders. They're being maimed. They're not being, the crushed is the narrative we talk about. Jason, who else is being maimed? Well, I mean, Atlassian is slowing down, right? GitLab is arguably being maimed. I mean, many public companies are being maimed.

49:10You've got to be Datadog and have so many leading products in market almost not to be maimed. It looked like Mongo was being maimed until they fought back, right? It really looked like they were being maimed by all the new Postgres and other competitors. They're back, although maybe they're maimed in the sense they should be growing faster, given the growth of AI. Like Mongo should be this great Broadcom-like AI beneficiary, and they are, but they have so many competitors now. There's so many Supabases and others that are taking pockets of market share away from them that you might not even see some of the maiming, right?

49:41Maybe Mongo should be growing 50%. Why shouldn't it be? It was the leading platform, and the explosion of apps that we're building today is unprecedented. Why isn't Mongo growing 50 %? The way you see it is you see those CIO surveys where they rank their priorities. And what happens is, you know, as AI has gone up the zeitgeist, it's gone up the priority list. And just something that was number three goes to number six, and then it doesn't get funded. That's part of the SaaS slowdown that we've seen across the board in the public companies. You're not selling the new, new thing. So I'm kind of with you, Jason.

50:10And even at the infrastructure level of the, you know, the GitHubs and things like that, you have to co-attach to where the budget is. And if you're selling infrastructure, but you're selling it to the people who aren't doing AI, then you're going to be dealing with a slow growth secular story. If you're selling that infrastructure to, you know, Entropic and OpenAI and the JP Morgan AI initiative, you're probably going to, you're not going to be an AI company, but you're going to have some of that growth rate. I mean, maybe the most maimed that I can think of, it may not be fair, is UiPath. Like we can say, hey, until Daniel came back, We missed the AI wave, but it's not that simple.

50:43UI path is not hemorrhaging customers. It's back to 16 % growth. Stock's up 27 % this year. Go Daniel, right? It just got maimed because, you know, RPA in part got replaced with agents and AI. It got maimed. It got maimed. You would just do, I think that's a great example, genuinely, Jason, because I think you are. It's kind of one of those moments where you do it in a different way if you were starting now to automate and you'd start with an agent. You just wouldn't start by doing the thing that they do. What do you do if you're Daniel? Daniel is one of my closest friends. What do you do if you're him?

51:14Well, he has stabilized the ship. Growth has come back a bit. He basically checked out like a lot of folks did when times were easy, when products didn't change. He called it a day. And then how long did that last? Eight months till he had to kick out the CEO he brought in? It didn't even make it to a year. I think what you have to do is say to yourself, there's a way you do automations in 2025. They're agentic. UiPath's automations were very deterministic and brittle. You do exactly these three steps in exactly this order, then it works, and you can automate away humans. Now you can have a 10-step automation where you have some decisions.

51:49The good news is there's a bunch of companies from Y Combinator on that are doing this kind of stuff, and you should buy or build enough to just take the pain and insert yourself into relevance. And I'm sure he's on it. I mean, this is a very smart man who knows what it has to take. But it's just, as we've discussed before, the hard thing isn't intellectually knowing what you have to do. The hard thing is just driving it through an organization who will invariably say, our stuff already does that. I mean, we've looked at a lot of the companies that are the next generation companies. And you do the research and you do the reference calls, and the UiPad team will say they have something like this.

52:24And they do. But in the eyes of the customer, it's not perceived as the new thing. And you've got to change that perception. And it just requires, you know, a supreme act of CEO will. I mean, I hate, I didn't like the founder mode cliche, but I've come to the conclusion it's what you're dealing with here. You just got to say, we are refounding the company in the age of AI. We are not going to lose any of these AI first deals and we're going to make it happen. You know, in a way though, I agree with all that. I think Daniel, as hard a job it is, he has an easier job than some, because let me just step back to the numbers.

52:54Here's what I would do. Come 1.8 billion in ARR, but he's got 98 % GRR and 107 % NRR. Okay. So mathematically one problem is his NRR has fallen from the 140 % peak at the IPO because people aren't buying that much more for UI path, but he's got 98 % GRR, 98 % retention. He has enough time as one of the greatest B2B founders out there to build the agentic products that$2 billion of his customers want to buy and aren't leaving. It's the same opportunity Mark Benioff has. Now, I think I would argue Mark with his megaphone is actually like an Aaron Levy is doing a better job publicly of bridging the gap, but they have the same job.

53:33We have extremely high revenue retention. People aren't leaving. No matter what anybody says, we're in the first inning for AIB2B. I can tell you why. We're in the first inning. It's brutal, but you have time. You've got six, 12, 18, 24 months to roll out high ROI agentic products. And you just got to get enough of your$2 billion base to buy them. And you're back to 30 % growth. He goes from 107 NRR to 100. You know, Databricks has 150 % NRR at 5 billion ARR. I mean, it's easy to say, but that's the job. Make those happy customers buy more of your agentic product. And it doesn't have to be all of them tomorrow.

54:09It has to be more of them each quarter. And you're back in the game. Isn't it as simple as the Alex Rampel quote, which I love, which is, you know, can the incumbent acquire innovation before the startup acquires distribution? Exactly this point. Yes, but you don't have infinite time. But I think everyone has time with 98 % GRR in 2026, 2027. You don't have infinite time. Get rid of the CEO you brought in so you could relax. Like go into Sergey Brin mode. But you do have time. The game is not over. To take that quote, I think it's a good quote. And to some extent it is quote that simple. but actually I'm going to find myself surprisingly agreeing again with Jason on the human factor.

54:47The hard part of doing it is can Big Co acquire innovation faster than New Co can acquire distribution? Let's take that as a construct. That's actually not the issue because they can acquire innovation if they can push it through and if a technical fund. The really hard part is there's going to be about two or three years where you're lifting the growth rate from 9 % to 11 % and the stock doesn't give a shit. And then 11 % to 13 % and the stock gives a shit. And then you're $150 ,000, and then the activist whine. Because the problem is, we talked about this with Salesforce, the physics. If I have a zero revenue company and I can go to$100 million, that looks amazing.

55:21If I have a$2 billion revenue company and I sell them$200 million of the new thing, I'm twice as big as this little sexy startup, but I've only got a 10 % growth, so I'm valued at five times revenue. You've got to push that Sysphere and rock up the hill for four or five years, keep everyone motivated, and just accept that it's a grind, right? And that actually is the hard part. And that's why I admire the CEOs. You know, I admire Benioff for turning up and keep doing it. I admire Dines. I admire Aaron enormously for that. They're just saying, we're not going to roll over and die because we can be relevant.

55:53We're just going to do what it takes. But the point I'm trying to make more than that is there's not a moment of, oh, I've invented the magic thing. We're cool too. No, the market will say, no, you're not cool. You're a$2 billion boring old company. You got to make yourself cool because 30 % growth, that's what's cool. And it's just that journey. 30 % growth, that's what's cool. I love it. Daniel is also one of the biggest warrior CEOs. You know, Ho Nam's cockroach founder, just relentless. I mean, Daniel is just extraordinary. The man survived on a dollar a day in Romania for years. You mean he was on the charts?

56:26A Romanian pre-89 joke. Yeah, a pre-89 joke. Listen, you said about co-attaching to budget and to AI budget. There are two that you could pick on for that from this week. Boom Supersonic, the plane builder that gets an order from Crusoe and is raising 300 million in the back of this to fund it and to open up this new line of business. Or Harness, which raised 240 million at five and a half billion to automate AIs after code gap. Which one do you want to take? Because both of them are. Harry, anyone who chooses between a supersonic plane and a software infrastructure provider and chooses anyone other than option A has no soul.

57:09Of course, you've got to talk about the supersonic plane. For God's sake, man, this is not even a choice. So just for context for everyone, Yahoo is just an awesome company. They are building a supersonic airplane from scratch, and they're designing both the plane and the engines. This is a hard, hard, hard task, even for existing plane manufacturers, typically Boeing builds planes, GE or Rolls-Royce builds engines. So they're taking on the full enchilada. I love it. It's a Y Combinator company. They got a prototype out with less than 100 headcounts. So everything in your heart wants that to work.

57:44A, because it would be great to have supersonic flight other than from Concorde, and B, just because it's just an awesome entrepreneurial story. So when I saw this, I will admit, I was like, huh. But then you do a little research, and I'd forgotten this, but Rolls-Royce, it's not as crazy as it looks, because what Boom said, they're also going to sell their engines to data centers for generation, right? And when you say it like that, it's like, ha, you were making planes, and now you're selling turbines. But in fact, all the airline engine manufacturers, GE in the United States and Rolls-Royce in Derby in the UK, I used to run a manufacturing company near there, they all do the same thing.

58:22because it turns out the bulk of what it takes to build an airplane engine, other than the last bit of propulsion, is very similar to what it takes to build a generator. So it's not crazy at all. My guess is, this is Jason, Captain Obby's, it's a lot easier to take an engine and plop it on the ground and have it generate electricity than it is to put the same damn thing in a plane and have it generate propulsion. So it was actually not crazy at all. I don't know if it's defensive because the plane has a huge regular hurdler, if it's offensive because they can make more money there now, but genuine comment, I wish them literally all the best of luck.

58:58Well, hold on. Boom comes out of YC, cool company, quickly raises at an arguably fake billion dollar round from airlines with no revenue. December 2024, a year ago, crashes down round, maybe$500 million valuation, but it might be worse when you think about the cram down and the effects. That's a tough moment. AI booms and now you're back up to 1.5 billion. 2021, 1 billion, no revenue, crashed to half of that or less at the end of last year, massive cram down round and then back to 1.5 billion. I mean, if I was an investor, I might still have whiplash, but it's great. But who knows how it looks with all that change?

59:35I'm not sure. Crazy story. There's so many of those. We all have them. We all have the ones, a couple ones in our portfolio that actually got a big AI lift this year. Didn't know it would be boom, but it was. But you must admit, it's one thing to get an AI lift because your cool little network monitoring tool is selling to Entropic. It's quite another thing to kind of walk into the factory and say, guys, strip those engines off those planes, slap them on a trailer and make them generate electricity for a data center down in Texas. I just love the hard engineering of it all. I would argue I don't lump boom into the reacceleration.

1:00:09acceleration. I think the interesting distinction is, I think boom in its old and new incandation are ultra high risk, very ambitious companies versus the software centric known business model reacceleration. I wouldn't lump boom in with some SaaS companies reaccelerating to 30%. They're just such dramatic risk profiles. I think the interesting question, and I'm going to tie it into the forthcoming biggest IPO ever. How do you think as a growth investor about ambitious, hard engineering projects like Boom, where, you know, as we've seen, the risk of it going horribly wrong and not building a plane is quite high, and maybe you get saved by building an engine.

1:00:49So you go, oh my God, that is way more risky than anything in even AI LLM land. But on the other hand, we're about to cover the big story of 2026, which is possibly the largest IPO in history is going to be a rocket company. I think the aha is when those hard tech problems work and when you solve the technology problem, and if you pick the right problem, you have a wildly compelling business. But as the boom plane part of the story makes clear, they're damn hard problems. Well, they've sold zero of either. They've sold no planes and no jet turbines for AI power. So it's a big bet. It is a big bet.

1:01:26And three failed launches in in 2007 and 2008. That's probably what SpaceX looked like too. And if it works, you're a genius. Speaking of the trillion dollar outcome and the big IPO for next year, we chatted about it. We chatted about the$800 billion secondary. Following that, pretty quickly, rumors around the$1.5 trillion IPO. It's funny. The exact chronology last week, we recorded on a Tuesday. We talked about$800 billion being a high price for that secondary round. And I was like, ooh, that feels like a high price based on the numbers. And I'd looked at the numbers and the growth rate and some the acceleration going on.

1:02:00And I'm like, ooh, 800 feels high. And then on Wednesday, before we even released a damn podcast, we see the leak that says they plan to go public at 1.5 trillion. So I'm sure everyone piled into the 800 billion round thinking, oh my God, it's cheap. So you can be wrong by 800 billion in a day. So I've obviously been thinking about that a lot. How do you get your head around that? It's a, you know, the company's doing 15, 16 billion this year, 2025. Starlink is the growth driver. Growth rate was down a little this year over last year. Maybe they do early mid-20s next year. So you're talking, you know, 70, eight times 2026 revenues.

1:02:36What's the thought process? I was genuinely thinking, how do you talk constructively about that? And what I realized is you have to factor in what I'm now going to refer to as the EOV, the Elon option value. Because on all his public companies, you just run the math, You value what it's worth as a business with the TAM, taking it all into account. And then you look at the difference between that and what it's trading at. And that's just basically the Elon option value, right? I mean, if you look at Tesla, it's trading north of a trillion. It's roughly 100 and something billion in revenue. Earnings are down.

1:03:05You kind of apply a normal multiple. Maybe you get 300 billion. The rest is the EOV. It will be the same thing on SpaceX. And he's earned that EOV because he pulled the Starlink rabbit out of the hat. It was a rocket company, and then it became a communications company. So it is credible to say in his case, as in almost no one else's case, this is one of the few people on the planet who literally might find you another trillion dollar market that wasn't in the original plan. So roll the dice. If that premium ever evaporates, oh, dear God, if he were ever to die, oh, my God, the stock gap would be something horrific.

1:03:39What I recognize is you can't run the numbers on SpaceX and come up with 1.5 trillion. You just can't. But what you can say is someone who's funded, let's be clear, the most successful car company ever. And let's not forget, also founder of OpenAI, looks like the most successful AI company ever, and the most successful rocket company ever. We said last week, once you're lucky, twice you're good. Three times you're freaking amazing. So I just have let go. I've let go of valuation. I'm like, I can't figure out how it's worth 1.5, but you just apply the ERV on top of the 10X multiple and away you get.

1:04:14It's awesome. You have to manifest it. That's the key you're missing. This is what he's doing. Even Harry's manifested almost a billion dollars under management. Like you can laugh, but if you have enough, enough behind you, if you have enough magic and proof points, totally. You manifest, I think he's manifesting a$1.5 trillion company. And I don't know if all the kids can manifest it, but it's, he's doing it. I can teach him. I've learned a lot. Teach him how to manifest it. I'm manifesting a beach house in Laguna Beach. You're a manifesto. Harry, you are, people don't get it. You are an S tier manifesto.

1:04:48I mean, then Elon would definitely be an S squared, S cubed, S to the power of 10. I mean, it just breaks the, you just have this other thing up. Yeah. It's just not even playing the same game. You look at the numbers and you go, you know, 15 billion plus or minus, you know, two, four or five billion of space revenues, which is wonderful, but capped, you know, you've got these customers, there's a certain amount of volume. They already have 90 % of the volume. Then you start estimating, well, how big can Starlink be? Dear God, let it be on every United flight soon. If anyone from United is listening, I actively avoid your planes because they don't have Starlink enough.

1:05:20So please fix that. So they get all that. They get all the rural broadband. You still struggle to get to anywhere close to 1.5 trillion. And then you just have to go. You're buying a share in probably the only person since the demise of Steve Jobs to literally not do it once, but do it three times. I mean, Jobs did it with Apple, Pixar, and then Apple again, right? Elon's done it with, you know, I mean, you forget the small ones like PayPal. And then on top of that, Tesla, SpaceX as a rocket company, SpaceX as a communications company, then, of course, OpenAI as the leading AI company. He did SolarCity as well, didn't he?

1:05:56He did, but that didn't matter as much. I mean, I was just a simple, humble$2 or$3 billion outcome, you know, nothing among friends. So, yeah, even rounding out the little ones, you just left with it's the most impressive of entrepreneurial record, possibly the last 30, 40 years, as I say, with the acceptancy jobs. You lean in. No, I can't get the math to work either, right? But the one thing is, I do think Elon's all over the place, unlike Sam Altman, where every single thing I think Sam says, as off the cuff as it looks, is very thoughtful. But I think Elon talking about space-based data centers is his next big play, potentially.

1:06:30I think there's a reason he's communicating this well ahead of the IPO. I think this is one of the big plays. I mean, it's an incredible business as it already is. I have three star links. I don't know what I'm paying a lot. Right. And it's great. But if all of that started in the beginning of the conversation of all that Oracle and core weave and Nebius revenue all goes up, up in the sky, deep, far in the sky, that is a lot of money. And he's the only one that can do it. He's the only one that can build data centers in space. And I don't think he's joking. And it's easier than going to Mars, or at least it's easier than getting back from Mars.

1:07:03It is not easier. Going to Mars is not a huge challenge. It's getting back. So we might be underestimating the data centers in space. It's possible. Would it be a successful IPO at 1.5 trillion? That's an interesting question for the buyers or the sellers. It will be the most successful IPO in human history for the sellers. I just think what Founders Fund are going to record on this is going to boggle the imagination. Will it be a good stock to buy at 1.5 trillion? Is that what you're asking, Harry? I'm saying, will there be investor demand at 1.5 trillion, enough to satisfy it, and then a stabilized period where it doesn't tank afterwards?

1:07:40I don't know because you're asking me to assess something that's not within the bounds of logic. I don't understand the Tesla market cap relative to the financials or even the TAM. I don't think people get that one running the numbers. So you're trying to assess the non-quantifiable. So I don't know how you can come to an informed conclusion. I don't understand the mindset of someone who would buy based on the intangible at that kind of price. I think as a rational buyer, you look at the upside downside risk and you get very nervous. But I think the same has been true of Tesla for the last five years.

1:08:12It's been up and down. The financial performance has been fairly mediocre for four years, but the stock has stayed up. So you're asking me to speculate on the propensity of the marginal Elon believer to buy the stock at 1.5 trillion, and I have no way of assessing that. I think it'll be a tricky one to get done. The bankers are pitching this week. I would not envy them their task. He does seem to have an ability that maybe no one other than Bezos in his prime has, which is give me five years. All of Elon's dates are wrong. Everything is full self-driving. Everything's behind from the Model S to the Model 3 to Starlink.

1:08:49And everyone gives them another four to five years. And the day traders are going to enjoy the stock. So it's just hard to predict when everyone gives you another four to five years. They're really not trading on today's revenue or today's anything. It's a gift, but he's very good at that. He's very good at over predicting, but ultimately delivering. You're exactly right, Jason. It is a daunting task. You know, are you going to raise 30 billion, which is only 2 % dilution, which means it's still widely traded? Or are you going to do the typical IPO has 8 % dilution? So that would be, I mean, let's do the math here, about 120 billion, right?

1:09:21Is there$120 billion of raw risk capital that says, what I really need in my portfolio in 2026 is some 70x run rate revenue space investments? Some poor banker is going to have to get on his PowerPoint, get on his private jet, and start flying around the world and saying, how much of this do you want? Now, I think in this market, I don't know how to assess who that investor is. Do the index funds buy it? Do the sovereign wealth buy it? I think there'll be a lot of a consumer and retail appetite. I just don't know how that all comes together. It will be fun to watch because it will probably be the most challenging IPO story if it's anything like that valuation.

1:10:01Now, the other thing you might see is the valuation gets walked back to the merely outrageous. The most impressive thing is the entrepreneurial oomph. I heard Peter Thiel speak about this years ago. When you have a big enough vision, you do get a buy on the little shit. And Elon, by having that big vision, I think, has been able to taper over the cracks that would have killed many a lesser man. Good luck to him. I mean, it's great. In the end, I like my Starling too. I mean, here's one snare for what it's worth. Google anchors them with 10 billion. They're already a 10 % shareholder. In for a penny, in for a pound.

1:10:30They may have, maybe it's a Gemini partnership in space. That's part of it. They get first access to the TPUs in space. It's not, no. So they put in 10 billion. It's good timing with AI. And as soon as that is, we're running out of space in the IPO. And the banks run around. Google's in for 10 billion. Fidelity's in for$2 billion. And all of a sudden, you start to panic that you're not going to get your shares. If you get a call in 10 minutes from Goldman Sachs or Morgan Stanley, you'll be signed up as a banker by Friday. I love it. You're exactly right. Maybe the best company is it's a narrative story.

1:11:00And Jason's just shown how easily a narrative can change. It's not a story like a PE-backed public IPO where it's like at eight times ARR, you can get 6x coverage. And at 10 times ARR, you can only get three. So the deal gets done at eight. This is a totally different thing. And this is in tune with the zeitgeist. It's all narrative all the time. And you're right. That would be a very clever way to do it. Jason, that was fantastic. Yeah, he should be a banker. He's exactly right. Well, Google almost bailed out Tesla at the last hour when it almost went bankrupt. It's already happened. And Sergey's back running Google.

1:11:30It's just 10 billion. I can tell you, we do work closely with a lot of the folks at Google Cloud with Saster. They are feeling strong. We work with a lot of folks in marketing and product. I've never seen a team feel more energized in the entire decade I've worked with them. They are feeling that they are winning. And so why not put it$10 billion to get my TPUs in space? It's a good deal. Fuck, it's nothing. It's a couple of percentage points of market cap. Not crazy. What else are they going to do with the cash? They can't spend it like Meta does. They can't spend it that aggressively. They already have engineers.

1:12:00They don't need to spend it on that. And Jensen's doing buybacks. So maybe he can stick a couple of billion. And there you are. Maybe NVIDIA could put in five. If they do 15 together, Google and NVIDIA and two from Fidelity, there's no room for retail. We're sold out. The round is sold out. And the genuine common and the genuine learning is, as I said, the power of a big story. At one level, there's a little part of me, the boring, curmudgeon, numbers guy, screams, this is all madness. You're all insane. And then there's another little part of you that just gets inspired by that we're sending rockets to Mars, for God's sake.

1:12:31And we're the telecom company that connects the whole world. This has got to matter. Just because you brought it up on Founders Fund, owning 10%, it's just a story people forget. Peter Thiel fired Elon Musk. Yes. He fired him, but he treated him like a human being, fully vested all his stock, took nothing out of his pocket, thanked him for it and told him that was the way it was going to be. He treated him pretty damn well. And so when SpaceX was going to die, he went to Founders Fund and Peter Thiel gave him the money in an hour. It's a reminder in today's age of extreme greed to be kind. He didn't just, wasn't just nice to him.

1:13:04He accelerated all of his stock and made sure that it wasn't about money. He was appreciated. and he walked him out the door. I don't see this happening often enough. I've seen two CEOs at the end of this year just quit their startups that I invested in. Be kinder. Go the extra yard like Peter did with Elon. It just may pay off, like owning 10 % of a$1.5 trillion IPO. Even for a billionaire, it might pay off. Yeah. Reserving the right to say I'm not sure how much it was kindness versus Elon was also a big paid-in stockholder. I think the meta point you're making is right. Two things are wildly impressive.

1:13:39One is the density of talent at PayPal blows the mind. It's like you have Thiel, you have Sachs, et cetera. You've Reid Hoffman. It's just amazing. You have Elon. And then the second thing is you're right. They clearly had their bumps. And the fact that they were able to be rational business people is about to pay off to the tune of$100 billion. It's a great story. It's kind of one of those wow moments and good for them. It's like Harry tweeted today something about people who aren't in the very biggest deals feel totally irrelevant. And you correctly got a whole bunch of pushback on it, Harry, because it was a bit obnoxious.

1:14:11But there's no doubt in a world where one investment might return 50 to 100 billion dollars, everyone else has to feel just a teeny tiny tad irrelevant compared to that return for founders fund. And good on them. It's a 20 year compounder at 50 percent plus or minus. okay we're gonna do a would you rather rory you love this you've got a figma at 17 billion or cursor at 29 jason i'm gonna take figma only because i don't believe cursor's future is a shirt i think a cursor is magical i think it's a gift to humanity for folks that have built software if we keep doing this podcast long enough we're gonna see i'm right about something else which is everything's much less stable than we thought this year.

1:14:59The categories, the Harvey's, the cursors, these are incredible companies. I wish I invested all of them. Don't get me wrong. We're going to look back in 24 months and see there was a lot less stability in these so-called leaders than we thought. It's not that they were going to go to zero, but we are so early in AI that I'm going to take Figma on this one, but it's a tough one. It's a tough one. Rory, you don't? No, I don't feel the need to argue. I mean, I think that that's the beauty of money. You just make your bet and And then, you know, you don't have to justify your position with English.

1:15:29In the end, you're right or wrong on the numbers. Yeah, Jason, you just need to argue. God. I like to argue. Let's shit on Harry's tweet and then just not argue. I was a little argumentative last week. I hope it doesn't happen again. But yeah, keep going. What's the next one? Open AI at 500, Anthropic at 360, or Google at 2 trillion? I have to take Google. The reason is just the level of, I don't mean arrogance, confidence in where they're going that I see across the team we work with. I know it sounds small, but it's not. When I see everything's going right and the team feels it and the team knows it, how often does that happen at this scale?

1:16:05Not that, I don't think everyone at Meta is cheering that they're crushing it, right? Risk adjusted, take Google. Wouldn't have been true a year ago. Gotta take it. Okay, I don't know my answer yet, but actually the point is a year ago, it should have been time to take Google because the stock's up 60%. You may be the wrong side of that trade. You should have taken the quick pop. I'm not a trader. I know. I mean, it makes north of 100 billion a year. So you're buying in at 20 times plus or minus EBITDA. It clocks in north of 100 billion of profit a year. Everything else was a positive when we talked about it nine months ago.

1:16:39And the risk was erosion of search. All the positives have kind of gotten better and the erosion of search haven't happened. So yeah, you do have to give it consideration. This is hard. At 170, I'd have taken the Antropic. Do you think, actually, because yeah, interesting comment here. Antropic is, you're giving me the future round on Antropic. Has it happened at 300? But the future round at OpenAI is, is there another round coming on OpenAI? They're always continuously raising. But if you were to do live pricing on them, Anthropics would be 360, unless you were getting grandfathered into a prior round.

1:17:10The real live price is 360. At 170, Bill, I take Antropic all day, every day, because I think they're being way more sensible than OpenAI. And I think they will get public. And yes, at 170, at 300, you might be fully valued. I think the difference between Entropic and OpenAI is OpenAI has more ambition, perhaps, but it's more likely to just get caught in the middle with commitments it can't meet. Whereas I think Entropic is very sensibly and boringly converging on profitability, will go public, and will be a very nice public company. So of the two, I'd take Entropic. I'm processing on Google, and it just feels lame.

1:17:46I mean, you could argue they're all almost public already. Come on, Rory. Shut your face. I think I'd go on Tropic. I think I'd go one of the pure plays, even though I do agree the Google. I think I'd go one of the pure plays. Kalshi Slowfire. Kalshi Slowfire. You know, I like to think before I comment, so call me strange. Don't worry. We edit anyway. It's all good. Yeah, yeah, yeah. Get rid of that one. Boys, thank you so much. You continuously make me more and more questioning of my own questions. You know, I've done this for 10 to 11 years, Rory. I never questioned my own interviewing ability until I started doing this with you.

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