20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

31 Jul 2025 · 1 h 21 min

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The Twenty Minute VC (20VC) - Episode Summary

Episode Title: 20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Needs a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

Podcast Overview The Twenty Minute VC podcast hosted by Harry Stebbings features discussions with top venture capitalists and founders. In this episode, Stebbings is joined by Jason Lampkin and Rory O'Driscoll. The episode covers a range of topics, including industry trends, venture capital dynamics, tech company performances, and growth forecasts for specific startups.

Key Discussion Points

  1. Benchmark Capital's Partner Departures
  2. Current Status: Benchmark has seen significant partner departures recently, with some questioning the stability of venture capital firms.
  3. Discussion:
  4. The changing landscape of venture capital is leading talented individuals to leave established firms for solo careers.
  5. The perception of a "hot hand" in venture investing encourages early departures for better opportunities.
  1. The Rise of the Solo General Partner (GP)
  2. Trend: Increasing interest in solo GPs as a new model for venture funding.
  3. Key Insight: Solo GPs may have more autonomy and financial potential compared to being tied to a fund.
  1. Elad Gil’s Fundraising Success
  2. Highlight: Elad Gil has successfully raised a $1.5 billion fund as a solo GP.
  3. Implication: This reflects a significant trend in venture capital where solo GPs are gaining traction and legitimacy.
  1. Tech Performance Analysis
  2. Apple’s Management Issues:
  3. Discussion around whether Apple needs a major management overhaul due to its inability to keep pace with AI advancements.
  4. Google vs. Microsoft vs. Amazon in AI Infrastructure:
  5. Google is currently seen as the best performer among the hyperscalers.
  6. Microsoft faces criticism over the management of GitHub Copilot and its AI strategies.
  1. Growth Forecasts
  2. Cursor’s Projections:
  3. Discussion on whether Cursor can hit $4 billion in ARR by the end of 2026.
  4. Concerns about the sustainability of its current growth trajectory.
  5. Lovable’s Projections:
  6. Lovable is forecasted to reach $400 million ARR, seen as more achievable compared to Cursor’s goal.
  1. AI and Developer Spending
  2. Increase in Developer Costs:
  3. The expected increase in spending on AI tools per developer, potentially reaching $10,000 per month.
  4. Implications for the market and overall tech spending.
  1. IPO Market Considerations
  2. Figma’s Upcoming IPO:
  3. Anticipation around Figma's IPO and its valuation.
  4. Comparisons to previous tech IPOs and the impact of AI on traditional software companies.
  1. Conclusion and Predictions
  2. Final Bets:
  3. Predictions made regarding the future performance of Cursor, Lovable, and OpenAI.
  4. The ongoing debates illustrate the intersection of venture capital dynamics, tech innovation, and investment strategies.

Key Takeaways

  • The venture capital landscape is evolving, with solo GPs becoming increasingly popular among top talent.
  • Major tech companies like Apple, Microsoft, and Google are under scrutiny for their AI strategies and management effectiveness.
  • The expected growth in developer spending on AI tools could significantly shape the market dynamics.
  • The IPO landscape remains unpredictable, with companies like Figma facing challenges in maintaining excitement in a shifting tech environment.

Final Thoughts This episode highlights crucial trends in venture capital and technology, providing valuable insights into the future of investment and company performance amidst rapid technological advancements. The discussions reflect a broader narrative of change and adaptation within the industry.

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For more information on The Twenty Minute VC, visit [20vc.com](https://www.20vc.com).

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Transcript

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0:00Ironically, Google, who we all piss on, has executed the best of the four. They have a model that works. Apple doesn't even have a product that works. Microsoft bought someone else's product, but then doesn't quite own it. So it's kind of weird. Facebook is desperately trying to buy product, but it's not like out of success. It's out of terrible psychological need for a product, even though they don't have a business to justify it. I don't think these guys are too powerful. If anything, I think there are a bunch of rich people on the back foot behind the new trend, desperately trying to catch up.

0:28This is 20VC with me Harry Steppings and it is my favorite show the week Jason Lampkin, Rory O 'Driskel and me sitting town to discuss the biggest news in tech. I want to hear your thoughts on this format of show. It has very quickly become the most popular show that we do. Let me know Harry at 20VC .com. This is the best one we've ever done very simply. Incredible debate, small lessons for me than ever before. Let me know what you think of the show and it was just so much fun to do. I'm so grateful to have these guys as my friends. But before we dive into the show today, let's talk about agents.

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1:47That's qualified .com slash 20vc with the 20vc spelled out in letters for goodness sake. And while Piper builds your pipeline, Atio gives you the CRM power to close and grow those relationships. Atio is the net 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 Atio 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. Atio also integrates with your existing tools and sings with your product data to deliver an AI native platform that's tailored to how your team actually works.

2:30You 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 data -driven engine from intelligent pipeline tracking to smarter product like growth. Fast growing startups like FlatFile, Repplicate and Modal are all experiencing what's next. Get ready to build without limits and start now atio .com forward slash 20 VC and get 15 % off your first year that's atioatti .com slash 20 VC.

3:12Okay pipeline sorted. Now what about your own legal team? Enter LaGora. Ligora is the category -defining AI platform that's fundamentally reshaping how legal work gets done about fricking time, empowering lawyers across tier 1 law firms and in -house teams to achieve more with greater precision and confidence. So Ligora 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 conversations that will not get a second date. But anyway, the adoption of legal AI is surging across the world, and LaGoura is at the forefront of this shift, as the chosen partner to 250 industry leaders in law across more than 20 markets.

3:58The likes of Goodwin, Bird and Bird and Deloitte are making daily use of LaGoura platform to review and research with precision, drafts smarter and collaborate seamlessly. They recently also got an $80 million series B. From iconic, they're backed by General and a catalyst, red point benchmark and YC. Also they operate out of New York, London Stockholm, yes their 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 LaGoura, honestly, I love Max their founder, he's just a great dude, go find out more LaGoura .com Team I'm so excited for this, we have a great schedule for today, as you know it's always my favorite conversation in the week.

4:43So I want to dive right in and start in the world adventure. We had Victor leaving benchmark. Now there's only three partners remaining with of C Eric with Chathen and with Peter Fanton. I'd love to understand how you thought about this and how you responded to it. One, listen, if folks are, if the best AI researchers are jumping from meta to anthropic to whatever in six months or getting massive packages, there's no stability and it should be the same adventure. That's thought number one, like this is not, whether it was ever a bucolic, but the idea of benchmarking the eBay days of a bunch of gentlemen investors staying together for 80 years, it's possible that's part of the past.

5:24And then the other tactical thing, I learned this myself, if you are going to leave a fund and you can, you have a hot hand, better to do it early, like staying longer doesn't help. Like it might seem like it helps the fund, it doesn't help you, you're probably not gonna leave with much carry, you're gonna have to start over. So there's definitely reasons to stay at a fund, right? Especially a top fund, but you might as well leave the moment you can. There's not a lot of economic incentive, not, you know, all things being equal to stay, right? Starting over is not bad fun. Very interesting. I mean, I think stepping back, you know, I remember benchmark founding in 95.

5:57I remember them pitching us in 95. So I would have said, what's happened here and benchmark will be fine. So let's start with that. They'll find two other people to fill those slots and they'll be fine because they've been fine for 30 years. I think the interesting thing is, to a rounding error I would have said being a partner at Benchmark is kind of one of the top gigs in Venture. They've been able to hire people from other places, other good firms, get them to join Benchmark, we all know the Stake, Equal Carrey, Focused Fund, no layers of hierarchy, it's a really compelling story and it's been a compelling story for 30 years.

6:28The stunning fact now is someone can be in the best gig in Venture and decide, no, it's not enough. I need something more, and they can actually probably pull that off. I mean, that to me is the big data point. It's less about benchmark. It's like a talented individual with obviously prior entrepreneurial success can be in venture two years and decide to leave benchmark not to go back to me and on kind of a founding startup entrepreneur, but to say I can get money and continue this business on my own on equally or more attractive terms. It just speaks to where the market is, you know, rightly along me.

7:02We can talk about that in a second for that kind of top tier talent. It's very much assigned the times. And you made a comment, most people who are good investors would prefer to just do it themselves. You stick together with your partners for, you know, you hope there's some strength and diversity of, uh, some diversification to use a less loaded term. And because there was a perception for a long time of a bare minimum fun -sized team size to get funded. And clearly all those perceptions are gone for at least a small number of very successful talented people. And that's What you are talking about.

7:35The thing, the nuance I've thought about over the years is if it were me, if I were myself at that time, at a similar spot, I wouldn't leave benchmark. I wouldn't leave benchmark because I think what a lot of these folks going out on their own miss and Harry and I did it, right? And Harry and I had brands behind us. We actually had brands. Quirky brands, Sastron 20VC, but I think especially today we underestimate how powerful it is to meet a founder and say you're from benchmark. It's friggin' powerful. Harry, I want to get your thoughts. I would argue that you and I are at the edge, anything less than a brand that we have, I wouldn't do, I just wouldn't, everyone's different.

8:11But it's not that you don't have the skills of hunting, it's not that you don't have the skills of evaluating a relationship building or schmoozing. You know, there's a lot of the best founders, you know, they just want the same guys that are in Figma. And 20 VCs above the line, but it's not, it doesn't have the storied history of benchmark, what do you think, Harry? That's why I'm not sure I would leave benchmark. I think people greatly over exaggerate the impact that this has on benchmark, Mark and I don't mean that rudely to Victor, but I don't think any firm has played AI in the last 18 months as well as Benchmark have done despite the team churn that they've had.

8:42Let's just go through this. McCaw over 100 million in Aero. Hey Jen, hitting 100 million in Aero. Fireworks 140 million in Aero. Sierra with Brat Taylor over 100 million in Aero. Manus AI, the best Chinese AI team there is. Lagour are the best European AI team there is in many respects. all with double digits ownership in one single fund. How, how could I be an LP in that fund? Yeah, first of all, do you think all those deals would have happened? I'm not a call stop here. Only because you actually didn't answer the question. We agree. Let's stipulate benchmark will be fine because they're awesome investors.

9:18That's just not an interesting discussion. I actually think until you cut them off, Jason was starting down the far more interesting discussion and it's super interesting with this group because I've actually never had this discussion with two people who've done the thing, there's very few people who've done the thing that Victor did, which is Razer Soul of Fund, and the odd thing is, I'm on a podcast with two of the people who've done it. Board of you, as brand names, right? So I actually think talking about his benchmark awesome is fun because they are fucking awesome, but it's just not that interesting.

9:46Would I do it if I was to, yeah, of course I would, I would, because he showed in his investing that he likes to move across scale in a way that I don't think benchmark likes are allows in their discipline manner. In a similar way, almost to Miles Grumshaw, who's another fantastic investor. But I think they are multi -stage investors and just want to intersect with founders, whether it's at the pre -seed, like Victor did with Brex, or whether it's riding a $55 million check into Hagen, which is really outside of what a benchmark deal would normally be, being that size check on entry. And I think I look at it and go, hey, I just want to engage with the best founders.

10:22I don't want the constraints of a partnership. I can get a lot of money privately from great individuals and I'll own 100 % of the carry. A fricking man, thank you very much. I'll do that all day. I hear you. I just have a more nuanced view now that time has gone on, right? I remember when I left, two top brand name funds reached out to me that I did not know well. Just it wouldn't have worked out, right? But I had a pretty hot hand when I did. Harry will remember, right? And I didn't even take the meetings, right, for real. Cause I'm like, it's just not, it doesn't, I can't get the math to work in my head.

10:51The 100 % of the carry, right? I can't get the lack of autonomy to work on my and I'm like I've been a founder with a modest level of success I'm gonna go work for somebody. I didn't take any of these meetings like but time has gone on and I do think that if you're gonna leave Understand the value of the brand you're leaving behind if you have no brand and here's my my own and Harry challenge me I just think in today's world if you have no brand at all. It's tough. I think it's tough 100 % you're so right it's tough, but I do know Victor and he is in the most exclusive inner circle of Silicon Valley that exists.

11:28He's in the Saragro Eliad Gil, PA, Graeves, Orel. Microbrand and the relationships that will make it work for him, right? And I would actually say the thing that's more important and attractive than brand is scale of cash. The only thing that I find attractive about joining another firm which I never would do ever, obviously, but it's the fact that I could deploy a billion dollar check into a great company. And actually, I think scale of cash is almost a more attractive magnet than stellar brand world change, right? We wouldn't even be having this conversation even four years ago. Even four years ago we wouldn't have the conversation, right?

12:03Yeah. What you find attractive about being on your own to your point, how the ability to employ large under China and Senate, the ability of our large amount of cash, what Jason is missing if making the point is so you give up on the brand if the existing brand is strong. So you probably have to come to the table with an equivalent brand and you probably do because if you don't have an equivalent brand you won't be able to get the big cash. So what you're basically saying is and I agree is that if I have let's just say a functionally equivalent brand as an individual to the brand of the firm I'm at in other words high high by so I'm not losing a ton on deal flow from transitioning and I get all the money myself, then I should just go do that because I can do what I want to travel.

12:45What's interesting is the people who need to think about this a lot of the LPs. And I'll tell you why. Because what it says is we will now finance you to do all the things that we spend 20 years telling every other venture from not to do. And I think that's a big insight. Very much an LP focus on discipline, stick to your lane, do the stuff you do well, we value teams, we value cohesion, we value long -term, and what they're now saying and maybe be correctly. This is not a diss. This is a reflection on where the world is and sometimes the value of listening to advice and sometimes the value of not listening to advice.

13:17What they're showing by their actions that we'll talk about allowed in a second is they also like a product that says, thank you for your input on being focused. I'm ignoring it. Thank but your input on being a value ad in terms of taking board seats in the last case, I'm ignoring it. Thank you for your input on small funds as I'm ignoring it. Or by the way, after giving me all this input, I'm ignoring it all and then you're going to give me the money. Note to self, what are you doing here people? It's super interesting. What it says is, as I say, thank you for your advice. Now, thank you for your money.

13:47It's an interesting time. What does that tell you then that Aladdin has such a strong brand that he is able to do that? Say, thank you for your advice. I'm not going to take it over and over again. I don't mean that badly against him. He's incredible. I think what it says is exactly that. I think it's probably says two things and the new ones because they go one way. One thing it says is in the end, idiosyncratic success triumphs bland mediocre standard advice windows when if you see something working you're just gonna lean into it because I think I hope it's correctly or saying I had this pattern matching thing and these are the things that I said we shouldn't do and then I look at this moving on to a lad here because we had a month's talk when this oh my god this guy was a seed investor Airbnb in stride he's riddened the last 15 years he's not put a foot wrong he has access to the best deals, screw my rules, this guy's going to make money.

14:36So on the one hand it says, you know, capitalism works. And so part of what's going on is there's a big signal coming here that says the things that we believe for 20 years might be as true today we should lean into the new. That's the positive side. And I believe that to be clear, I actually look back and I go on and show you last but this one I say in a second so we'll put a pin on this. You look back and you go, hmm, there are things that I thought one had to do that you look back and go maybe you don't. But let's leave that for a second. The other side of the table is this. Sometimes rules of thumb or heuristics are in place because across cycles they've been proven to be correct.

15:13My guess is some part of this trend makes total sense and some part of it you look back after next down and turn and say oh yeah that's why we had that rule. That's why we had the stick to the knitting rule. That's why we had the more than one partner rule. And I think you'll find some parts of this, like totally free and easy, will prove to be challenging as you move across an entire cycle. And zooming out, never forget, there's no data on anything through a cycle yet for anything that started from about 2010. So I think the LPs, they're discarding some of their rules of thumb. And in some cases, they'll be right.

15:49But my guess is there was an embedded piece of wisdom in that that will come back when you've discard it to bite you in the butt as you go to the next downturn. That's a long answer, but it's a super rare. I frankly, I think it's a super interesting subject. I think E -Lad is the best embodiment of the concentration of value. And to your point of picking your space, you said, very wise, he -bery. And I always remember this. Josh Kushner is a master property developer in the way that he picks the block and buys the best house on the block, Stripe in FinTech, Data Bracing Data, Open AI and AI. and I think Elad is very similar in terms of making sure that whatever that category leader is, whether it's Helsing or whether it's a bridge or whether it's Stripe, or whether it's Harvey, he is in that leader and he's in it big.

16:34I think that's really impressive with him and then he's also an amazing picker. I remember he sent me Vanta at pre -seed. The man has access to like no one else. He's able to cover spectrum like I've never seen before. You know what I worry about when I see this news, speed of deployment equals relevance. And I think about this, because we're very disciplined on three -year fun cycles, temporal diversification. I know everything that we've said, maybe Jason doesn't agree with on temporal divers, but just like doing what we said we do on how we invest and how slow we are, I see actually cadence of deployment can lead to relevance in a way that really benefits that manager.

17:11It does. We talked about this before, you internalize that in the short term that's true. The only people who mind money are the people in charge of minding the money. And the people who are in charge of the mining money here are the LPs and they're trying to figure on the one hand they want because people are deploying capital quick to getting capital out by definition getting short term positive feedback. No one applies a billion dollars, values it at 800 and then gets more money. So if you deploy capital quickly you can assume you're getting markup to getting success, you win the hot deals.

17:38And what you know you're left with is the LPs trying to figure out, is this a hot hand that I have to follow? Or is this a flash in the pan signal and it could blow up in my face? It's a tricky thing to figure out, because by following, you made a common inconsistency, by doing what you said you do, by being consistent, you lower the chance of just drifting off and screwing it up, but you probably pass up on the upside of being as aggressive as someone who's not honoring the tempo diversification and who is using that velocity. So all other things been equal, the person who's doing more deals has more relevance.

18:13So therefore the only question, as long as they're deploying it well, it's a double win. You have relevance in the short term and returns the long term. If you deploy it badly, you have relevance in the short term and failure in the long term. I've seen examples of both. I mean, I think a light gild is example of the latter. I think widely successful seems to be doing everything right. I'm willing to stipulate one of the most talented and investment generation and will do it really well. Right, and continue on doing it well. That's one example. I've also seen the examples of people who've been relevant for two years because they're putting the money out and then the money blows up and they're gone.

18:45Tigers, the obvious example. Now they're still around, but a shadow of their former selves. They're caught on court relevance in 2021, meant that they saw every deal that year, but they picked that, so they got sent home. Something with soft back. Any early stage VC worked a damn in Silicon Valley knows who the dumb late stage money is. And you can tell, I remember watch I won't even name names, I was like, oh, that late stage investor is attending that early stage investor meeting, I know why they're there. That's money, that's the money that they need. And those investors obviously blow up. So in the end, relevance is a short term thing.

19:19And in the end, as I can say about this job, the only thing that's true about this job over the medium term is you have to be right. And the hot hand who's right across an extended period of time, and as I say a lot, I think is one of the best of that, you deserve to get the capital. but you deserve to get the runway because you've proven over 10 or 15 years your ability to pick. And as you say stunningly, pickboard early and late. We can come back to what is wrong with the single personal mod, but I'm willing to say the following. If it doesn't work out, it won't be because the personal insurance of it isn't brilliant.

19:49He clearly is. It'll be because, strictly, there are problems with that model on that stage. Well, the interesting thing is when you look at botany, the best performing managers or the breakout managers the last years, I think you put probably thrive, greenotes, founders fund and Eli Gil, definitely up there, and all four of them are one person led. I'm not saying there's not great teams beneath them, but they are one person led very dominantly. That is interesting, and that's a very significant change from the venture partnership of old that was so predicated amongst the industry. It is, and it's easier, I think, perhaps well only to be one person led the later you go.

20:23And the reason I say that is this, let's just play it out. If you want to be an early stage of plaster, right, and you're putting up doing series A's, I'm going to say just doing a message because I recognize that all the names you cited have some amazing early stage investments and I want to come back to that because it's important, right? Because there was an insight in that that the pure late stage guys didn't have. If you want to put most of your money in early stage investments, what it means is every partner can only do so much. And if one partner is called the dominant partner, then all the others are, you know, to some extent not able to speak for the firm.

20:55And you don't want to have a person doing a 10 or 20 % ownership position who can't speak for the firm So I think in early stage if all your dollars are going early stage even as a partner in the firm I want the guy in the next who's running 10 more deals beside me to be roughly a pair of mine Because I don't want some weak person who's not that good who's a frankly bit of a beta who's willing to work for half nothing to be running my money Which is why benchmark as the quintessential early stage firm internalized you need to have of equality so that anyone can be a premier partner. It's totally different late stage.

21:29When you're not trying to be on the board, you're not trying to be involved day to day, your time is not consumed by the deal. You're just making decisions. Making decisions arguably can be best done as a smaller group. So in the limit, you can have one person making the calls on the late stage deals, and it's much more scale. Because remember, if you try to put out $1 billion, and you want to write in $20 million checks, someone has to make 50 decisions. But if we put it out in 100 million dollar checks someone only has to make 10 and it's hard to make 50 decisions So I think what you see about these mainly late stage funds is That someone is capable of making the big to sit they have structure to do other things But then someone is calling the big shots and they begin to write and that's true for green Clearly true for founders and I mean my guess is fast forward three years There'll be three other people in the firm and junior roles but that guy would be calling the shots and he's earned the right turn.

22:22Roy, can I be so blunt? Does it make you question your model? When you see these kind of dictatorial ad firms, not in a hard way, but dictatorial ad firms with mass capital sources, and then you look at yours more disciplined, lead sized and with partnership structure? No, no, because... I think we're all children of the era we grew up in. You know, we've survived two downturns, and typically in the downturn, the high price late stage guys go bust. So, and I'm not saying all these guys will, but it's what happens in every time because remember, you're only taking one risk as a late stage investor, which is valuation risk.

22:56And when it goes wrong, it goes wrong in a hundred percent correlated fashion. Everything blows up in your face. Or my liquidation preference always bails me out, doesn't it, Rory? Yeah, you're being, and by the way, and just for our listeners, you're being sarcastic there. You're exactly right. It doesn't. So, I think to build over an extended period of time, I think you have to build much earlier and that's been our primary focus and I think to do that you have to have much more of a partnership structure. So I think that's the place you end up in. If you wanted to build a late stage firm you can be much more hierarchical by definition almost you should be because there's a whole bunch of economic reasons we can talk about that.

23:30cynical comment, but cynical. Realistic comment, I said this to our place. If I know in 2009 that we were heading into the best equity decade ever with zero recessions coming out of the worst equity decade in a long time with two sessions, I might have played a different hand. If you know that stocks are going to go up pretty on stop, but we're in an all -time high today, they've gone up for 15 years. If you knew that, the correct risk adjusted, work adjusted, money adjusted play was to just do Tiger and not quite shank it in 2021. If you knew then what you knew now, you might make that play and make my money, but you you design to survive the cycles you've seen.

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24:10We can move on, but I actually would go that Tiger will do better than people think. You're given their positions in open AI scale. There's many others that actually are not bad companies. You said that they picked wrongly. Oh, they didn't pick wrongly, they just picked everything. And in that, there's not good and some bad. And it's not, oh my God, look, there's stunningly successful investors. It's just, you know, as an LP, you probably would prefer to have skipped that experience because one of these you have to look at is you'll have this phenomenon of the average IOR is great but if most of the funds went in at the top, you know, the LPC just participated in that and that's so happy.

24:47I agree. It's not that they're not going to make money, I'm sure they have many mentions, but it's not investment excellence as you'd want to live it. But I just got to commit one other point because it was important that I put a pen on it. I think the names you cited, those excellent investors, the green notes that throughout, one thing that's super interesting about those firms versus I'm going to call it the quintessential late stage only firms is, these guys also have done some amazing early stage investments. I mean, by definition, Peter Theal at foundation did the best early stage investment ever, Facebook for 500K.

25:15The interesting insight is it's not that they're caught in other early stage investors. The real brilliance was realizing that being a great early stage investor with an implicit two three hundred million dollar fund size allowed you to have a three billion dollar fund size where the median, you know, the pooled dollar return is on your late stage investments because you're deploying lots of capital at late, but the on -share to that has been your brilliance at early stage investing. And that's why those guys are different, and in my view, better, more likely survivors than the late stage players who dash in from the public, think it's all a financial game, and then get blown up.

25:51The list you named have in my view played it perfectly, and including jumping a lad in that, having really great early stage deal flow on access and then realizing that the best way to monetize that is to follow on your $10 million paycheck with a $200 million series each check and collect the money every way. The brilliance of Josh and Neil from Thrive and Greenhouse, they made half a billion dollars plus from Carvana in the public markets, buying when it was in the dumps and writing that up. That is a fucking good picker when the world tells you otherwise. I mean, such a bad idea. that stock chart to make that bet.

26:29It was a, it was a night, falling knife that one, right? And then Neil also does Windsor for seed. Yes, okay. I give up Neil too good. Anyway, we said about concentration of value and the topic started out raising at a hundred. Got so much demand it went up, it went up. It landed somewhere between 150 and 180. I heard it was closer to the 180, which wouldn't be surprising. I'd love to hear your thoughts on how you guys read this, what you make of it. But look, the interesting thing here is I believe that there was a billion late last year and four billion this year So this is classic the thing of what really counts as the first derivative the growth rate Maybe even the second derivative not just the growth is good But the growth rate appears to have accelerated which is stunning, right in other words because most your expectation is you start off growing at 300 percent Then 200 percent then 100 percent see the absolute numbers are going up But the growth rates down these guys appear to have We accelerated at scale.

27:25So you're doing a billion, you're, I don't know, doubling more than doubling and suddenly you're doing four billion and you're four five X's. So if these numbers are correct, that's amazing. And I think that's what's getting valued. And we can both feel smart last week because you pinged us on open AI versus on traffic, open AI 300 and traffic at 100 feeling pretty good about that 1 .8 X in a week. If only we bought. So yeah, people are looking at the acceleration and it's clearly a two horse race, bootleg and whatever one else, either not shipping or not monetizing and are not relevant in the case of some of the smaller things and you're buying the reaccelerating winner.

28:03I'll tell you for what it's worth what I you know you also asked about capping cloud code right for for for overage. I know there's one part of entropic but my experience in vibe coding, I mean my captain obvious learning is were vastly underestimating the revenue potential per developer, per user of cloud and enthrop. We're vastly underestimating it. We're vastly underestimating it. Why Jason? Just educate. Because what was clear to me, I was on a path to spend $8 ,000 a month vibe coding, okay? And even with that, Harry, what's happening now, now the context windows have gotten longer. So now on Repplet, and I think Lovable just did in the new release, you can have up to a 15 -minute long context window while it's thinking through debugging or complex stuff.

28:45Okay? You know what I would love to do now? Run four of them at the same time, or maybe even 15, okay? So that 8K bill, all things being equal, could easily be 10K. And I remember, I didn't get it, you know, maybe a month or two ago, Farhan, one of the CTOs, I think CTO Shopify, let all their developers use the most AI they wanted, no caps. And the top guys were using 10K a month on credits, because they were running multiple things in parallel, okay? And if we're talking about 15 minute context windows and this you know, whatever open open, I mean Chatchy be five as a you know, whatever a million tokens or billion token windows, right?

29:23Debug my entire code base now do this other thing and now I'm doing 10 things in action I think everyone every developer at top tech company growing is gonna give them $10 ,000 a month of AI credits Everyone's gonna get 10 ,000 not 200, which is what we're thinking We thought that was a lot a couple months ago. They're all gonna get $10 ,000 a month, every leading tech company, it's cheaper than hiring any human, and you can't find human. So if that means a 50X growth per developer spend, it's gonna be a CFO's nightmare, but putting that aside, that's 50X growth from where we are today, for a cloud code and on -thropic.

29:58Or if they use it through cursor, it really doesn't matter where you're buying the tokens, 50X per human. That's a lot of growth, isn't it? I'm convinced it's not even, it's like blinding the obvious to me now, and Shopify already got there. Like 10K is fine, not 210K. You know, and the other thing that the CEO of Repplet said, I think yesterday about this was, you can't cap it because any great developer will consume almost unlimited tokens no matter how cheap they are. So I think we're all gonna land at this 10K, eight to 10K per month. If you're a good developer, you're gonna be on 24 hours a day.

30:26You're gonna be on AI, not a couple minutes here or there. Directly, I totally agree what you're saying, which is zooming on a million miles, I think we're saying is, and bringing it back to one topic. These guys have something, a model that makes developers who are expensive assets, extraordinarily productive. Somehow the market's going to find a way to mastery reward them, I agree. And you made a comment on capping and it's been interesting. Separately, I'm tropic, did some capping for their plans and I think Kursin did some capping and some token limit for their plans. And you'd ask the question, how are you?

30:55Is that good or bad? I think it's amazingly good. What it says is, there's infinite demand for this product. Right now at the price point of 200 bucks and the cost of generating those tokens, the economics doesn't work for the model provider. And you know, you could look at that and go, oh my god, I'm going to worry about the fact that this is the economic model ROM and as a point in time, it probably is. My guess is someone has gross margins of troubling. But when you're selling something with a couple of facts, one is the long term trends are in your threat favor because all these cost just go down over time.

31:26Thank you very much, Mr. Envidia. And you've got almost in for the demand. You just price it to the point where you just get these people hooked and over time your costs are going to go down and their hootness as Jason said is going to go up and maybe today you're selling them 200 bucks what a tokens. You're getting 200 bucks and maybe you are spending 250 bucks in tokens so you cap them now at 170 and you think your margins are crap but next to that 170 will be 120 even if the token count goes up and as Jason says you raise at 200 to 400. What it says is there's a not infinite but an astonishingly strong demand pull for Claude code and related products either directly using a via Claude code or indirectly using the ontropic models without one of the other providers like Amcursor.

32:14That's going to reflect in the ontropic numbers which is reflecting in the valuation and it's going to reflect in a whole bunch of pushing and shoving around gross margins for a year but in the end you'll stabilize out to something that works for everybody. It's astonishingly bullish on market size and growth. We're all gonna be coding 24 -7 with our agents. Everyone's saying that it's so hard to get a job in software today if you look at the Wall Street Journal, if it's not remotely true. If you have the skill set today, if you're a super smart in math or CS or physics, and you're in any school today, my son's a freshman and he's off the charts in math.

32:48He already has offers, okay? If you're top tier developer, you just wanna arm them up with every tool you possibly can because no one wants the folks that went to a devrive programming school, like they wanted in 2021. That market is dead, right? So we're going to arm them up with 10k a month. Let's need to have everything that you say then, Jason. Anthropic is at least a $2 trillion company. Maybe, right? There's just so much investment here, right? Now, are there issues? If obviously OpenAI is coming very hard at them right now, right? I'm not signed up for $2 trillion and I don't have to be to say, yeah, you know, this is going to be an extraordinarily only valuable company.

33:21There are only four or five companies that are worth more than the trillion and it's worth pointing out only one of them is selling just kind of developed and video obviously which is pretty much a monopoly selling you know 100 % market share in the most valuable commodity have. All the others touch every human being on the planet who has IT. Apple, you know Google, Facebook and Microsoft. For an arachn just to say it. I don't think you get to it more than $0 ,000 ,000 if you're just selling stuff to developers and effort, which isn't to say I don't think you do extraordinarily well. If in Throp Against the Year at what, $7 billion in revenue, right?

33:58And let's say the average and Throp Against the Year developer customer is paying $100 a month now, and that goes to $5 ,000, okay? Yeah, if you want to buy $50 ,000, $50 ,000, $50 ,000, $50 ,000, $50 ,000, $50 ,000, $50 ,000, everything's amazing. Yeah, but I'm not being facetious. This is my captain obvious epiphany. This is bigger than the $4 a month we spent on JIRA at Atlassian. All the VCs like to talk about how AI is gonna tap into the human budget. And some of it is just Sony Bologna. I've learned this is completely true for developers. $10 ,000 is nothing to replace a $500 ,000 fully burdened developer that quits in seven months, Rory.

34:35I'm not being facetious when I think it's 50X. I'm not being facetious. It may not add up to $2 trillion, but I think the T -TAM, the TrueTAM, is 50X what it is today without question, because this is the greatest case, not of making developers just more efficient, but of truly tapping into that non -existent human budget that people have, right? There's no one to build this software out there, or there's no one to build it. There's an outside of cursor, no one can hire anybody. And even a cursor, it's hard to hire, isn't it, Harry? Listen, you mentioned lovable, we mentioned Ratplates. We saw Microsoft, we saw Google, roll out lovable slash Ratplates competitors.

35:10is question being that, is it too late? These are actually various established brands in rapid and lovable in this case. Is it too late or is incumbent distribution so overwhelmingly strong that they will be the victors with these? The Microsoft competitor to Lovable and Replet, right, and Bolt. Now this will change its beta, right? It's limited. Everyone shares one database. So you may have seen some issues I had around my database, but at least I had my own one. Everyone shares the same database. So Microsoft has declared warning, Maybe be careful what you put in the database. Maybe you don't want to build what's the app that just had the terrible leaks today that we were just talking about before we started.

35:47Yeah, don't build the T because everyone sharing the same database. What that says to me is, look, listen, Microsoft can catch up. That's not taking this seriously enough. Or it's being so panicked that you have to put something out there, which is probably more of the case. They're so panicked that it is a big deal, the replete -level or 200 million in six months, that will put something out there that No one in their right mind would use. Yeah. One database. They only bought one, they could only afford one instance at Microsoft. They only could afford one database at a time. They could only code one at a time.

36:18But yes, the answer to the direct, is it too late? In other words, are the lovable is already too established for Microsoft to matter? I think Jason's is the right answer. It's more question of, are they going to focus on this thoroughly and comprehensively enough to win? Because if they did, if they put all the eggs and winning this basket, right, they probably could. It seems odd, for example, to angst as Microsoft about, oh my God, I'm losing 100 million dollars where I'm need to loveable. When wake up, I'm losing 900 million dollars to cursor in a product I already have been shipping for five freaking years in GitHub Copa.

36:52It knows if the thing you delivered first can't beat the newcomer, how are you going to beat the even more trivial newcomer where you later than them? It's just a massive fuck up for Microsoft. If you're sitting in that meeting, you're going, oh my god, we had the lot start, we had the runway, and we've let someone come up from behind and seemingly trance us. Is that the mindset you think? I mean, they probably would say, oh, we have 500 million dollars of revenue we're doing. They probably have some corporate story, why they're better. But the truth is, yeah, it's a mistake. If you start with a monopoly, and you fast forward three years and someone exists, by definition, you screwed up.

37:31Your job as a monopoly was don't lose the monopoly, right? They had massive market share with GitHub. They added the coal pilot, you know, when that was CEO, it was an excellent product. And you know, fast forward four or five years, they seem to have slipped up. I mean, you can't not say it's a mistake because you shouldn't let that happen. And that's my point. If you're chasing shiny object symptom on the next thing, which is now I have to do a lovable thing, are you really quitting enough effort into making sure that your cursor competitor is as good as it should be? And I'm not fully formed on this yet, so I'm kind of going out and look for all the Microsoft is amazing in AI story The better than AWS as of the three hyperscalos, but they don't have their own model the relationship with open AI is a bit tortured cursors now 900 million and their developers, which is their core kind of raise on that try in a world where they're at five one with a five -year start I don't think they're playing a perfect game and I don't know if trying to do still more things is the way to win here versus actually doing some things well.

38:31You know, Saddamade, it ever saw funny comment that, you know, he wanted to make Google dance. Well, you know, fast forward a year or two, they appear to be dancing pretty fucking well. Microsoft own Open AI in many respects. Amazon own anthropic in many respects. And then Google own distribution and Gemini in a way that is very, very powerful and important. You have to buy one and you have to short one, which one do you do? By Google short, AWS Amazon. Google has the advantage of on the estimation. It could lose its search business that knows it may you know that it does a lot in this because mev I was just talking about the hyperscalers if you looked at the three hyperscaler execution then it's easy.

39:10Let's just do the hyperscaler first because otherwise we don't have to think about retail and search which are big things I admit on the three hyperscalers five years ago Amazon built the category I was the dominant one Microsoft was number two because they could lever over into the Azure so they were kind of limping on to the field with a bunch of relationships and Google was nowhere to the point where there were credible stories about them getting out of cloud. Fast forward to this quarter, Google's nailed it, great quote in Q2. As of the recording, we don't know where Amazon and Microsoft is, but funnily enough by the time you produce this podcast, people will know because I think they're reporting tomorrow.

39:46But my gut is just looking at the trends that Google is pulling ahead and is the smallest but by far the fastest growing. Microsoft is roughly equal in scale to AWS, admitting that there's all of some weird accounting of Azure, and has a slightly better growth rate. So by definition of the three, AWS is the hyper scale around a performer, and I'm 100 % certain I could make that case. If I had to make the bet today, I would make worries, but I wouldn't, I won't make it for the captain obvious reason that one of the reasons is there's unlimited demand, and it has its own TPU, right? As Amazon licks its wounds and recovers, which is already working code red on, right?

40:25When it gets back in the sweet spot of what its customers need demand will be unlimited agreed I think you're right Jason, which is you look at Oracle Then I mean and I look at this a lot because there's a little part of the contrarian in me that says Could you hit the point where that stops because if it does stop the corrections going to be super interesting? Right, so I look at it and then I have to and I'm kind of trying to be a cynic and I'm trying to find some evidence of overshooting on demand and to your point, Jason, you exactly right, I can find none. You kind of go, I can't remember what the Amazon or Microsoft said.

40:58You have biggest problem and didn't have capacity. I think one of the other hyperscalers said, we could sell more shit if we had more shit to sell. And you write to yourself, that is the best thing in the world is to be selling something that everyone wants to buy and it's just a beautiful place to be in right now. And all those guys are there. Yeah. And the Wall Street Journal had an article yesterday of what the number one KPI for public company CO's is it's reducing headcount and growing revenue. Reducing headcount. That's the number one. From Bank of America on down, it went through all these big, not just the little tech startups.

41:27Everyone wants less headcount. And the answer meta is AI. There's unlimited demand to do that, to drive headcount down and revenue up. So I guess it's going to end, but when we're all just living in the matrix, I don't think it ends that way. I'm just going to go out another level. I don't know if I had two coffees today. I don't it ends when everyone's automated and the demand stops. And I'm keeping an eye on this because there's a trade to be done when it happens. I think what's interesting is the creation of AI kind of is happening at hyperpaste as you know 600 billion dollars of CapEx whatever just a huge amount going on.

42:01Enterprise is a ability to adjust that is still well to be slow even though demand is growing you're still at the super early. And I think one of the weird things would be how long can you continue investing 600 billion a year against a 30 billion dollar growing revenue line. Like for example, even Microsoft was interesting. They did a bunch of layoffs. Satya did this comment on the enigma of growth. I didn't quite get. I think what he's saying is really, yeah, it's pretty cold blooded to fire a bunch of people when you have hypergrotten 40 % operating margins. But what he didn't say is part of the dirty little secret is we're going to have to start appreciating, you know, half our free cash flow and CapEx to the the income statement over the next three years.

42:38So we're going to have to take people out just to be the same level of efficiency. At some point, someone's going to depreciate all these Nvidia chips and someone's gonna have to pay for them. I do think there might be a slowdown at some point in time but right now there's no evidence of it whatsoever. Everund did the, oh my god Nvidia's in trouble at 140 and now it's at 170. The only trend were to dam in the last year has been lean into the hypergrowth. So Anna Sanro, you're saying depreciation is the primary reason why you'd see that damn thing? No I'm saying if you continue to spend and run through your income statement large cap ex without an associated revenue line, eventually the world says, dude, maybe you shouldn't be doing this.

43:18And the truth is, right now, you're getting to depreciation, you're not getting the revenue commensurate with the spend. You're getting revenue growth. Jason is right. There is large corporate demand, but even with the best will in the world, they can only digest so much software in a year, right? It's David John from Secours. I love that piece, because honestly, I thought about mining something like it, And I was like, oh, it's done now. Don't need to say that. But the interesting thing is it's a great quote. You know, the market can stay euphoric longer than you can stay solvent. If you traded that position a year and a half ago, you'd have said, the man's gonna top out, you'd have shorted Nvidia at 100, and you'd be one sad poppy at 170.

44:01And forget even the stock prices, the spend by the hyperscalers have gone up since then. So I think the thesis is actually correct at some point, But that's excuse my language fucking useless if you're a stock trader. Is it correct today? Is the only question worth a damn and I don't know when that happens And I think when you bring that back to Jason's point of the $10 ,000 per developer I just want to buy more and more and more in video today and I go Fully priced for that baby. So I'm not in the same place, but I think Jason is right fundamentally That insatiable demand is there the only question is how quick they can it be met quick enough to cover the nut Can I ask you, and I sound like a communist here, but we have never seen incumbents at this size and scale before, with this dominance, where they can drop $15 billion on a team, and it's 40 days of free cash flow who gives a shit about the money, it's worth the chips on the table.

44:57And when you look at Google's asset base, it's insane. These companies too powerful. No, I'm just going to go straight out to the no, because whenever you've been, whenever have been a quiver calendar. One of my big ahas, whenever we'd been a quiver calendar these kind of questions, you end up with people coming up with dumbass things like the whole AI regulation, like the whole FTC process. So there are some things about these powerful corporations I don't quite like and I wish we could do nuance and like fix some of the problems without going crazy. But if you have to pick one of two worlds either idiot regulation or just let free capitalism one wild, I'm voting for the latter because I think in the end Mr.

45:35Markard will take care of these things. I don't know, Mr. Markard says that Adam's missing visible hand, and you're seeing that now with zuck, hiring with an unlimited budget, making B2B hiring to Jason's point in the biggest problem in startups, that will just get worse. The interesting thing is we have to decide if all of the gopolis are okay. Now monopolies, the case is clear, right? And maybe monopolies are good. Monocepies are even more complicated, but we could argue the monopoly dynamic here, all of these that we're talking about, The reason they're interesting is they're oligopolis. We have three to four players, right?

46:08Oracle's all of a sudden competitive, right? Massively competitive with Google, with Microsoft, with Amazon. We have OpenAI and Thropic, GROC in friends. I think if you want to give up on oligopolis, I quit this venture. I quit this business. Let me return capital. I'm going to do an open view. I'm calling it a day. Here's the rest of the money. I'm going to write out my winners because if oligopolis aren't OK, I quit. Like, if you read a classic textbooks on oligopolies, they compete on features not price. There's a lot of hints of that, right? That these products kind of are the same price, right?

46:40Today. And a lot of folks believe that's good for an economy because oligopolies maximize innovation. They don't maximize discounts, but they pour all the money back into R &D because they're competing on features not price, right? If you believe in technology, you might almost want oligopolies. Three to four players. I totally agree with Jason. I just want to come back to your point on to the perfect because I think there are two actually slightly different comments. All of the incumbent older companies, the trillion dollar companies, are in their own market monopolies. Apple, I would argue near Microsoft, Facebook, Google, in an old market, search, iPhone, social, the resist that definition forever and whatever Microsoft is, corporate.

47:22So in the old businesses, they're in their monopolies. But Jason's exactly right in these new businesses where they're putting their money and where the new startups are coming in What you're seeing is oligopolis, which is what you'd expect now maybe fast forward 10 years and they got grind down to monopolist But right now in the markets that matter for all the power that Apple, Facebook, Microsoft and Google brought to the table It's open AI and unchoppy that are making the one in so I would argue that says there's simply no need for these whining, worrying, F -15 people to sweat it because the truth is none of those companies executed well.

47:59I mean, ironically, Google, who we all piss on, right, and say that it's good, has executed the best of the four. They have a model that works. Apple doesn't even have a product that works. Microsoft bought someone else's product, but then it doesn't quite on it, so it's kind of weird. Facebook is desperately trying to buy product, but it's not like out of success. It's out of terrible psychological need for a product even though they don't have a business to justify it. So I don't think these guys are too powerful. If anything, I think there are a bunch of rich people on the back foot Behind the new trend desperately trying to catch up.

48:30What do you do if you're Apple? You're looking at that assessment, which I completely agree with. I think it's a board You say to yourself do you have a management team that's too old because that's the only button you have and I love to Apple is my largest single position I have agonized about selling it for a decade and a half and I haven't so I love that man Thank you very much my little house much gratitude But you just do wonder is this the team to grab what's going on in AI Which they absolutely should have a product on and at some point do you say you just have a bunch of folks who aren't figuring it out?

49:03And do you make a change that was a comment rather than some kind of Tactical hey you should buy XY or Z look in the mirror and say are you getting this done now? I think it's very hard for a board to do. I think if they hard for a board full of supernolaries to do It's very hard when the numbers are still good, but you know you haven't gone in five years You've done a magnificent financial engineering. Thank you very much again for your dividend But you're not winning and at some point the box starts at the top Do you guys think AI is a legitimate threat on its own to the App Store? No, because if I look at Apple today It's 25 % of the revenue is from the App Store 40 % of its profit, right?

49:40Yes, and 75 % of its revenue is iPhone and App Store So if AI just enables more apps to be purchased and Apple keeps its tax, right? Maybe you should stick to your lane in the short term, right? If you couldn't get Siri to work after 27 years, if App Store is a monopoly to your earlier point and it's not everything's under threat from AI, if it's a beneficiary of AI, right? Then maybe they have the last laugh. Maybe they have this high margin last laugh of all this AI revenue gets more and more of it gets routed through App Store and they take their 26%. That could be worse than taking 26%. I'd, by the way, I agree with that, Jason, because you're right.

50:18When you make the hardware and the logistics of making the hardware, the thing you're amazing at and hoping it designed, your whole business doesn't go away. You can talk about Google, ironically, and say existential threat to the downside of no search. No matter what stuff we're using for AI, I think we'll be using my live phone. So I think that's a very fair pushback. It's not as existential. But the brutal thing about capitalism, it's like, what have you done for me lately? Congratulations on building the best consumer product in the last 50 years. Thank you for the App Store business and the services business, which is fucking awesome.

50:48But did I mention, you know, what's the new new thing, right? Do you want to run the risk of another waving my arms furiously here? Open AI type personal companion that knows everything about you. Do you want to let anything get between this and you as a user for your one billion user base? So I, wait, it's not existential, It's not like but it's a you know, it's a sharp thing if you're not moving forward You're dying and they're not moving forward an AI Google pays them to be the search provider And maybe they just collect their tax that way you're exactly right then that open AI can do the same thing And maybe Apple says we build great hardware a hardware has such a dominant place that people will continue Just to pay us money.

51:29So you know, we got it from Google and we'll find even though the courts are trying to stop that now We're just gonna get it from open AI you right That's the argument that says, stick in your lane, you make the 20 billion from other people giving you money. I don't know if I buy it, but yeah, that's the argument. I don't know how much open AI pays Apple to. Let's assume it's still zero, right? Which it used to be. I'm skeptical. But, you know, if it's, I mean, Jesus Christ, 108 million going through per month, even if there's a sweetheart deal here, if Apple can just keep 25 % of all that, it's a good model.

52:03Yeah, one of the challenges I would push there was only in the hardware is a great bit and it has a long inertia factor. In other words, long after you stop innovating, you can steep monetizing, which is I think the stage where they're now. And the question is, at some point, do you need to do more than that to keep not just surviving but growing? And maybe it is staying your lane and just get paid by everyone else effectively for placement. I love that debate, by the way, that was a fantastic discussion. For me as an observer, it was brilliant. But you said there about management teams, which maybe Zuck hired again with another stellar hire from OpenAI, Chief Scientist or whatever it was.

52:42He is going all out. To what extent are we like 80 % of the way there in his mind do you think in terms of his acquisition on talent spend versus this is 5 % of the way there? Like when does Zuck stop this siege? I don't have a clue. I mean his argument which when you heard that speak is if I'm spending 30 billion dollars On CapEx a year or 40 billion whatever it is now Should I skimp on the five or ten people who can spend that most correctly? It's Jason's point the super S tier engineer is spending so much money that you don't care My assumption is that at some point the margin return on the next side just gets negative So you probably stop spending a hundred million bucks a pop but you know, I get what he's done.

53:24He said, I'm gonna spend $40, $50 billion in CapEx. I better spend a billion, $2 billion, $5 billion to make sure I have the smart people to kind of implement that program. It makes us. You know, it's not even that big of a deal because if he wants, which isn't gonna happen, he can always just stop. It's only in the past. He can stop tomorrow and say, we're just gonna harvest classic Facebook ad revenue. We're gonna become the next Yahoo and we're gonna kind of just be a cash cow. If you're a public company that's massively profitable, Well, the past doesn't matter, does it? You can write off anything, you can fire all the people, and you're still obligated with these massive contracts, but you can also write them off as one time expenses or stick them in another bucket.

54:02They don't matter. If you have massive cash, you can always do a Mulligan at least every eight quarters. Yes, and obviously they did a Mulligan on virtual reality with the whole thing. Yeah, the Mulligan. The argument, again, he gets today, are you buying insurance or is it existential? I mean, implicit in that statement is that if you do nothing, think if you're unsuccessful in AI, your core business just continues to compound. And as long as that's true, you write Jason. It's the core business is kicking off what's the $200 million bill in the year of revenue, you know, 40%. If a core business is kicking off $40 or $50 billion and you make a $40 or $50 billion mistake, you just go on the penalty box for a year when you move on.

54:39You exactly write. But of course part of the reason he says he's doing it is because he says it's existential. So the horrible outcome is you misfire on the new innovation and the new innovation eats your core business. Like I would argue for Google, if they misfired on AI, they wouldn't have search. Whereas I think your point was right more right than me. If Apple misfires on an open AI type AI product, they'll still be making hardware and it won't be existential. And to your point, if Facebook misfires on Meta, they clearly still have Facebook. And if they miss fire again on AI, as long as they still have 40 billion of free cash flow, nobody cares.

55:18So you're right. Intentionally, you know, Zuck is telegraphing to the market, I'm making this bet, like very clearly, right? And so like when I was a VP at Adobe, you're trapped with your 40 % net margins because you can't invest in anything. Because the market is expecting cash to rain to the bottom line. And yes, Shotnew did a good job when they're moving to the cloud of getting some credit once for a massive generational shift. But Zuck can not only spend all this money, but he can say to the market, give me a little bit and Larry's doing the same, right? It's Oracle, give me a little time, right?

55:47We're gonna get back to those classic margins and the market won't punish you because most public companies are trapped in their margins that are profitable. You're stuck, like you can't go back. It is almost impossible for most public companies to actually spend the cash they're generating. So Zuck's got a triple down here because he's getting also a hall pass. The market's saying it's okay to spend everything. Let's remember, it's not only that the market won't punish you, them. Home. Portant point is the market can't punish you because in the case of meta you're voting control. Well, your market, but your stock price can be finished.

56:16But it's worth pointing out. That's why I think you exactly right, Jason. If you're a, quote, normal company, your stock price goes down and the vulture circle, whereas if you're meta, your stock price goes down and you're sad and you say sorry and your employees don't do as well and there's dissatisfaction, but you still have control. Same thing with Oracle. So I think that you're right. Those two players can swing a bat, secure in the knowledge that no one has a voice so to them. And they can actually spend their cash, which is otherwise trapped. It's trapped with these large public companies.

56:44It just builds up in weird areas and it's unspendable. All you can do is repurchase your stock. All you can do is buy something and acquisition and do some accounting shenanigans, right? Or repurchase your stock. Most steady state boring public tech companies are trapped when they're profitable. It's great because you're not losing money, but the lay people like, why don't you invest it? It's not that simple. Your EPS goes down. No one likes that with a normal company. No one wants to see Zoom's revenue, EPS go down, like it's the whole value of the company today, isn't it? And this is why Mr.

57:15Buffett is right. Once the company comes X -Growd, the most important thing to assess about management is their ability to rationally allocate capital, including sending that capital back to the shareholders. And which, as we've said before, Oracle has done in space. Final one, and then we'll do a quick fight. It's just figments of seeing an IPO this week. I do think we have to talk about it. I don't think enough people are excited enough about it. I remember when this would have been the most exciting thing in tech this week and it would have dominated news This is you know, it looks like a little price that you know 18 .8.

57:46I think it prices 5 p .m. Either to sail tomorrow, which is yesterday when this is out. Are we excited enough about this? How do you expect this to pan out is a pot bait in help us understand it as an audience? I think it's unfolding if anyone listened last week and this week by definition though I blotten for punishment But it's unfolding exactly what we said last week, which was the price, the filing range is I think 24 to 28 or something like that. They've drummed up the mat. We felt low. They've drummed up the man just in the last 24 hours. They've refiled to I want to say 32 to 35. So it's worked.

58:20The bikers are doing a great job. They've whipped up enthusiasm. Now that they know they're ultimately over subscribed, they've raised the filing range. I'm sure the rest of the drama is pricing at the high end or maybe above the range. And then a pop. So the whole movie's unfolding, exactly, you know, mission executed. There's been a lot of talk about how they're trying to make people be more specific about their demand, to better allocate their shares and avoid that pop. But I think the structure of these approaches means that that's almost unstoppable. So my gut is, and this is horrible because you're predicting something, you're breaking the first rule of predictions.

58:54You either predict the number or time, but never boat. And I'm predicting something now that by the time this thing comes out, people will know for idiots or not, but my sense is it's hard not to imagine this thing pricing and then popping very well because the structure of how they went at it is such that they will almost certainly be that money left on the table feeling. But I'm widely excited about it, I think it's great. But I think everyone gets excited once a prince. It's all just talked now, but the reality of four VC firms each making a billion dollars, that'll focus the mind. You know, it's 22, Saster annual was in September then.

59:31The doby deal acquisition happened. 10 ,000 people talked about nothing but Figma. Nothing. It was a fascinating deal because the 2021 bubble had imploded, crashed, right? And all of a sudden, Scott Belsky and Timur Heroes, they're going out in 2022 and paying 2021 prices for this scrappy startup Figma. And it was people's jaws dropped, right? It's like this was the deal of the century, right? Fast forward to today. And my ecosystem people aren't talking about it. Listen, four VCs making a billion dollars There's great topic for the pod, right? Don't get me wrong. But it's just boring to people today.

1:00:02And it was 10 ,000 people, executives, that crowd was hushed in 2022, September 2022. No one ever, nothing to talk about. And now, I might burn 6 ,000. I'm my cloud credits this month. This is lovable, did one again. I mean, it's just, hopefully this is a $30 billion market cap company for all of our sakes. But the zeitgeist has been lost here in traditional software, even the best or the best to the best. Figma is S tier. It's the maybe it's the but it's it's not capturing our imagination the way it was and maybe that's okay. B2B software used to be boring. Maybe it's super boring again. First of all, I just want to cue the Scotty Schlafer, you know, the interview, the Feynman interview when he says, you know, you win the Masters and then, you know, five minutes later, it's like, you know, the press is asking me, how are you going to play next week?

1:00:46This feels like that. It's like, you know, venture returns $30 billion and all Jason's got to say is, well, you know, what's going on at level? It's the vibe. We're all fibers now. There's no doubt that once you announce a 20 billion acquisition, everyone's kind of mentally ran the cash register, so you don't get to, you don't get to, it's hard to take the victory lap twice, but I totally think they deserve it. But I think the more salient fact is what you're saying is, there's still going to be a few more pre -AI IPOs at scale, because there's a couple other companies like that like Hanva and stuff.

1:01:15But you write, the hype cycle has moved on to the new story on what's going on in AI, which by the way doesn't mean that massive amount of money can't be made in other areas. And even in, you know, I think if you look back, semiconductors, semiconductors became uninvestable by venture in about 2004. And in the subsequent 20 years in the public markets, people made out like bandits. It was the best performing sector ever, even excluding Nvidia. video. So what's happening is start up activity in the space that Figma plays is not going to be a thing anymore. Imagine you're not going to build a non AI collaborative design tool.

1:01:53You're not going to build a non AI any kind of be to be software. So as you say this on the excitement, the new thing is not that, but that's a function by the way of it taking 12 years to go from the start up to an IPO. By the time you get to an IPO, I think we're to see this across the board. By the time companies that are 10 year old get to an IPO, you probably are half a tech cycle or tech cycle behind. It's terrifying. You hold and what I said is to an LP, our holding period is now longer than the tech cycle. That's a terrifying fact. Figma's holding period is 12 or 13 years and you're now in a world where they talk in the S1 about, you know, we're going to have to adapt to AI.

1:02:33Now, it's going to be an amazing company. It's going to be great. And I think they will adapt to AI. But it's We're talking here about intangible things, not money things, and I usually prefer to talk about money things. But you write, Jason, from a buzz perspective, the cowavans moved on. But on the other hand, it's moved on in the positive 20 to 30 billion dollars. I think everyone involved will get over their sadness very, very quickly when they look at the stock sets. And when Figma nails vibe -coding, man, that's going to be what we all want. I mean, they're going after it with Figma mate.

1:03:02I know, but it's what we really want. we don't really want because if you look at the the replettes and the lovable like today and the world's gonna change And I'm a super fan of both right now sending my bumps But a huge use case today is prototyping if we're being realistic. It's prototyping apps and it's very powerful and it's very fun And the pixel perfect it. Ocity is terrible like the apps look you can smell these apps And they're not what real apps look like so as soon as I go into Figma and do this and it looks like I really want I want it to look like a designer. I'm out. I'm out of anything that's not pixel perfect.

1:03:34I just don't want it. It's just like a square space site. I don't really want something that looks like square space. And I can smell a lovable, a replicate app within six seconds of hitting their website. Figma isn't gonna disrupt programmers, right? Like the way lovable and replete is. But this prototyping, I don't really want to do it in these apps. Listen, you're closer to it Harry, than I am. But I can't imagine this isn't a very interesting war in 2026. The war between vibe coding and... Figma. Right now they're great. You can go into Bolt or Lovable and Repplet in different ways. And in some cases in one click go from Figma back and forth.

1:04:08It's great, but today they're great partners. It doesn't make sense that they will be great partners for prototyping in 12 months. It makes no sense. And Canva saw this early, right? I don't know whether they'll really get there, but they saw it. That's why they went, tried to go really early into this. They got it, right? I think Canva's product will much more compete with Lovable's being the much more consumer friendly, children doing science project, at mothers doing businesses. I think the designer to really average consumer bluntly is a very different product paradigm to design for. And I don't see that competing.

1:04:38It makes sense that Canvas is a bigger competitor at the low end, right? That's why Wixbot Base 44, whatever. But a lot of developers are using these products to prototype. The folks that have helped me as a vibe coder, these are CTOs. I just see Tio reach out to me at 80 million. He's like, I just didn't want to distract my team. I'm building my own app in Repplet. Here are my 10 tips. And so I would rather do that in Figma. That use case. So the competition is at multiple levels, right? I'm tracking that. Yeah, because some part of the Figma user base is, you know, more picture -perfect, full -on built -out apps.

1:05:11But some is rough me out what this thing would look like. And your point is you might want to do that now using a tool that actually builds you a vaguely functioning prototype. Well, even more, like, I listen, mad respect for Figma. But as an end consumer, I hate it when I get a Figma link. because the thing doesn't work. I don't wanna click through from like, this is why working with designers, I wanna blow my brains out. I don't want static stuff. Like when you send me my Figma, okay? Now I'm not expecting that it works in production, right? I want it to work. I don't want design elements. And so as soon as my Figma works out of the box, it's vibe coded.

1:05:45That's all I want. And then the fun thing for those guys, I mean look, the very best companies, one by founders who see this, who've demonstrated, and in my view, these guys clearly have the ability to bounce back from stuff. I'm going to be all over this shit. And you know, 12 months from now, it's going to be, if you know what I'm doing, the bill in dollars that's taken it, it's going to be fun to watch what kind of products these guys roll out to be competitive with parts of either the coding, the cursor, or the prototyping marketplace, and how that design all the way through the code marketplace shapes out.

1:06:15Because there's a big part of money here and everyone's trying to make sure they get that bit. We're going to have some fun here, okay? So we're gonna do a cow -she -quick fire, but I'm just going free -rogu on this one, and I tweeted this last night because I was just super freaking intrigued to see where everyone landed. And so the tweet was, let's play a game. End of next year, over under. Rory, you're gonna love this. I can see it in your face. You look thrilled. There's been a lot of preparation. You haven't shared the information. Okay, go. E -lit like a sad puppy over under end of next year.

1:06:46Number one, cursor hits 4 billion in ARR by the end of next year. Over under. Under, but close. Yeah. Well, you think Harry helped me multitask. We're coming up on a billion today, right? Yeah. And the bed is 4 billion next year, right? What is just my L Thor M model say? Just trailing velocity say that gets me to almost three billion or so. Yes, you get to three billion. Yeah, so. Okay. Now, now use my math of at least spending twice as much per developer bare minimum, right? You get that. You like? I got to go, yes, on this one, the four billion. You're exactly right. I buy that. And that's, by the way, it's also proof.

1:07:23If they're doing four billion, I don't believe the gross margins are as negative people say, but if it goes by, it's a 50%. That's another two billion coming on tropics way. So it's been good for them too. Yeah, I don't think the gross margins are negative at scale, at a truth they're not scale. I can tell you, as someone who keeps paying these replete checks, they ain't negative. I guarantee you, replete's gross margins are pretty good. Okay, I bet they're in the 60s even today. I could be wrong, but they're not losing money. At least at the gross margin level, there's no way they're losing money with what they charge, right?

1:07:51It's a high markup to give you this environment, right? It's a high markup on those tokens. Lovable. It's 400 million ARR by the end of next year. End of next year? I have no doubts. Yeah. That's easier to do the math. 1 to 106 months, I mean that would be a colossal f -up if it doesn't get to 400. It's crazy as it is, right? It's interesting. When I look at those two bets, they're not the similar in the sense of a lover of ring at 400 million versus cursor ring at 4 billion. Right, I'm just trying to assess the wealth of likelihood of the two. I think the cursor bets a little more sure. Look, the trajectory of lovable as you know better than me, 100 % points to that.

1:08:31The only thing that could bite you in the but would be some kind of churn explosion. And you obviously have the data and I obviously don't. So I'm just trying to come up with, hey, if your job is invested to think, what could prevent that from that? Yeah, the bull case is easy to make to pull out of our rear. The bull case is easy. We could do that. The bear case is you were wrong about long term duration of subscription. And you know, you would argue Jason, that's not the case because you're now a guaranteed vibe quarter subscriber. Final one, we've chatted a lot about predictions. The final of mother of predictions, open AI, is it over or under 800 billion valuation for company?

1:09:06When? By the end of next year. Oh. Reportedly raising now between 360 and 380? Under. Why? I'll tell you what I'm doing mentally. It's no larger. I'm just looking at the step -ups and the rounds as you'd expect are getting smaller. You get two or five X and then you have you go from 80 to 150, which is almost a double. Just on the 300 to now 350. I don't know if there is a 300 in this and now it's a 350 going on. I'm just guessing, do you see another doubling round by the end of next year? It's a lot to have happened. It might be worth it, but another price round above 800? Don't know. I'll take the contrarian on you there and say that because of GPT -5 and because of code X being two very significant breakthroughs, they'll have enough plus Johnny I've coming out with something, a first product.

1:09:54The three combined will be enough to get enough excitement over 800. I'll tie it out. Just two quick thoughts on it. One, I think there is so much money and more invested in this company. Sometimes these valuations are just willed. People are too deep. Everyone's too deep into OpenAI. And if OpenAI needs 800 to survive, OpenAI will find 800. It may be through investors that get other things. It may be through existing investors. It may be through weird combinations of offshore money. No one can afford for it to lose anymore. There's so many stakeholders that if that is what needs to be solved 800 it will it will be solved and I actually think the meta issue You know the the the ceiling thropic had this thing this week where he was explained because they're they're supposed to be the good guys Right this we left open AI to build something safer and he's explaining why we have to take money from the Middle East now We have no choice we his point I guess the flip side is he didn't want to that that this was lowering their their their pristine ethical values To take money from the Middle East, but his point is we have no choice right so I think the bigger issue isn't 800 billion because people are invested.

1:10:58The bigger issue is when will all the capital on earth and Mars be exhausted? And that is a finite number, right? It is a finite number. Trump has already lassoed into Stargate with David Sack. I mean, Rory can help me figure this out. There is, at some point, I hope, and I could consume all available capital available to it in the Western world, or in the Eastern world. Talk about it more. No one's worse than that because it's actually interesting question. And I think Polar Kodzowski did a piece, right, which is just looking at the CapEx investment in AI as a percentage of GDP and comparing it to two other booms, the dot -com boom and the railway boom in the 1840s.

1:11:37I love that because again, I was trying to think through one of the compables and those are and the railway track analogy is a good one. So we're running now at about 1 .2 % of GDP, you know, which is basically 1 .2 % of GDP is going into making CapEx data centers, which is a little above the 1 .1 % of GDP that was going into bandwidth at the top of the 99, 2000. So we're already slightly bigger than the bandwidth boom, and we know that ended. But interestingly, I did not know this. It was 6 % of GDP in the railroad era a year. So at peak railroad mania, it went to 6%. Now as they pointed out, in that case, you were building an asset that lasted 150 years, and in fact, just today did a huge acquisition, Whereas in this case you're building an asset that appreciates over three years, so it's not like would like But just to kind of give a sense of the outer bounds to your point Jason of how crazy could this get We're already a bigger boom in terms of CapEx the 99 2000 But we're no one newest biggest boom as the real one boom The pleasing thing about that answers allows bought parties to continue to feel great if you're a nervous guy like I sometimes and we're like, shit, this is crazy and the 99 2000 makes me nervous.

1:12:46The internet was big, don't know. If you're an optimist, you're like, hey, we're only spending one quarter of what we spend to build a railroad and intelligence is better than railroad, surely. So we're fine. So it's a nice piece of analysis that literally doesn't allow you to conclude anything, right? My gut is, I don't think you can get to 6 % of GDP. Apollo is 4 .4%. Apollo, well, I don't have wing -y if, but I'm totally willing to do it. That's 4 .4 % of GDP across eight or nine years, which is an annual spend of about 3 .4%. It's not a single year. There's no way we spend 4 % on Apollo. You know, we're only spending 6 % on defense.

1:13:24So no. If I believe Reddit, which is always correct, but 4 .5 % in 1969, it was just under it in 1968, 4 .4 % of our whole economy. And all seriousness, I think that's why Sam Altman named it Stargate. I think everything he says that seems simplistic and calm and almost cute. When he says Stargate, he's like saying, listen guys, we spent 4 .41 % for several years on Apollo. We should spend more on AI. Took me a little while. I don't think anything he says is flippant. I don't think it's flippant. I don't think it's off, off the cuff. I think he's doing his own nerdy style of clear communication.

1:14:05Stargate is Apollo. We need it all and David Sacks is making it happen. So 6 % on railroads ended in a bust 4 % on I'm gonna give you 4 % for two years and I'm gonna check it ready Well, let's say you're right. It is worth pointing out in 1970 They just stop funding NASA like crazy because if you look at this if you look at this chart on Reddit the crash is bad Man actually peaked in 1965 peaked in 1965 We've got the moon were done. That's kind of recycled dollars here. So 4 % then it crashes So yeah, you can look at 1 .2 % of bandwidth and a crash is so we're clearly above the possible crash limit But below the out of bounds.

1:14:44I don't know what to make of that right? I don't know if you spend as much per year for five or six years on this as you do on ribbons We'll see and this is why going back what I said earlier You can love the long term trends But at the same time you can say to yourself at some point that could be a break in the spend to bring it back to your point And it's also why you have to go to Southern well funds. Because you need, I mean, we're now so irrelevant in the context of financing this that it's almost laughable. I think it's, I'm gonna get in trouble for this laughable that's a moral debate on, oh no, I'm sorry, we have to go to Saudi for money.

1:15:18No shit you do. Because that's where the money is. I also do, it's there to them. And I'm trying to done my, they obviously, from day one on traffic was set up very much to be more angsty than most about trying to do good. And it's interesting if you look at board companies, I mean if you just read OpenA -An and traffic, it's been a long journey from we only want to do good to oh my god we need to raise a lot of money and it's it's almost touching and it's starting off with innocence and then coming to grips with the fact that it turns out it's very hard to raise $200 billion for charity whereas $200 billion to turn into $800 billion you can find pretty much anyone to do it.

1:15:55Basically watching a whole bunch of folks realize that there's a reason why capitalism exists. It's actually very, actually life -affirming. As a capitalist, you can go, hmm, these are people who at Prairie would have been appalled by all this, but when they went out to actually pursue their dreams and they wanted the capital to get those dreams possible, they had to join the system. Yeah, welcome to capitalism. To tie it back and that's why I think open, if the, if, if, if open AI needs to raise it 800, not wants to, if it needs to, it will solve for it. Whether it's solvent wealth money, whatever, marked up stuff, warrants we don't see backdoor promises, promises for access.

1:16:30That's actually an interesting point. It'll solve for it. That last one will be the... I mean, we didn't talk about it. We didn't have time. But you know, I, Jason, part of the asset you have to monetize is your ability to tell large, solvent wealth. You know, you can tell it. I mean, I think open a eyes are where they're telling it. A domestic sovereignty story was give you your model, will give you a thing and people aren't going to put an AOR on multiple and that, they're going to, you know, for the right. Yeah, they don't care. So I think you're right. I'm not sure it'll be worth a hundred, but I've, again, one of the reasons I like doing this is I changed my mind when I hear good arguments.

1:17:01You write JSON if they, if they probably could find a way to back into it, which is different than saying it'll price the day it goes public in a public market, which will be a very different discussion. Team, I've got to be honest, I think the best show we've done. I mean, for me as a spectator, I've enjoyed it the most. The debate has been fantastic. Bravo, both of you. Really amazing fun. Thank you. Thank you for this, guys. Now, I want to make those shows the best shows they can be. So please let me know what we can do to make them better, improve them. If you want us to have a guest on the show, I'd love to hear your thoughts.

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1:21:16As always I so appreciate all your support and stay tuned for an incredible episode of 20 sales tomorrow with data brix's CRO Ron Gabrusco.

From the publisher

Agenda:

00:00 - Why Benchmark Is Bleeding Partners (and Why That’s the New Normal)

04:57 - “I Wouldn’t Leave Benchmark… Unless I Had THIS” — Jason on Brand vs Autonomy

09:01 - The Rise of the Solo GP & The Death of LP Conventional Wisdom

13:50 - The Unstoppable Force of Elad Gil & The Myth of LP Discipline

18:45 - Is Vibe Coding the New SaaS? Jason’s $10K/Month Spend Reveal

26:57 - Cursor’s Growth Is Insane—But Is It Sustainable?

31:44 - Will Microsoft, Google, or Amazon Win the AI Infra War?

37:42 - Is GitHub Copilot the Biggest Miss in Microsoft’s History?

44:15 - Are Big Tech Incumbents Now Too Powerful to Fail?

48:00 - Apple’s AI Problem: Is It Time for a Management Overhaul?

52:30 - Figma’s IPO: $30B Return, Zero Hype. What Happened?

1:06:00 - Final Bets: Cursor to $4B ARR, Lovable to $400M ARR, OpenAI to $800BN?

 

 

 

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