
The Twenty Minute VC (20VC) · 2026-08-20 · 1h 13m
Key moments - from our scoring
Substance score
51 / 100
Five dimensions, 20 points each
This episode examines three blockbuster M&A deals reshaping the AI landscape. SpaceX's $60 billion all-stock acquisition of Cursor represents one of the largest tech deals ever, with hosts debating why Elon Musk succeeded where Mark Zuckerberg didn't and analyzing how Cursor pivoted from an email client to the leading AI coding assistant despite gross margin challenges. The acquisition underscores the strategic imperative for companies with massive compute to own distribution - SpaceX's colossus cluster now has a proven revenue vehicle. Separately, Stripe's $7 billion acquisition of OpenRouter demonstrates how fast-moving infrastructure consolidation works in hypergrowth markets. OpenRouter raised at $1.3 billion valuation just four months prior, making this a 5x return. The hosts argue these valuations reflect acquirer currency and the speed of market expansion rather than traditional DCF metrics: when markets move 10x year-over-year, strategic buyers pay premium prices for immediate market share rather than wait to build. The episode frames these deals as emblematic of how pessimists identify real problems (gross margins, competitive fragmentation) while optimists capitalize on explosive market growth to generate generational returns.
SpaceX built a massive compute cluster (colossus) and needed a proven revenue vehicle to monetize it; Cursor was already the leading AI coding assistant with strong product-market fit and could immediately fill that compute capacity with high-margin inference revenue.
Cursor maintained aggressive growth through a hypergrowth market despite selling tokens at below cost because the market opportunity (70-80% of Anthropic's value) and growth rate outweighed margin concerns; an acquirer with massive compute could solve the margin problem.
OpenRouter is an LLM router that lets enterprises use multiple AI models through a single API; Stripe acquired it because it mirrors their existing payments business model (taking a small percentage of money flow to manage complexity), and because AI-forward customers are already driving 10x year-over-year growth through the platform.
Potentially, but Meta lacked the strategic imperative - their core ads business generates over $100 billion and dominates their interests, whereas SpaceX had excess compute specifically needing a revenue vehicle; also, Meta likely faced greater DOJ antitrust scrutiny than SpaceX.
Not typically; instead, losing the first-place acquisition pushes incumbents to buy number two or three as a fallback priority, rather than creating a land-grab panic where everyone races to consolidate immediately.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode delivers a mix of substantive analysis and repetitive commentary. Strong moments include the detailed breakdown of valuation multiples for PE deals (Workday at 5.3x vs. Airtable at 2.7x), the $100k AI spend per engineer framework, and nuanced discussion of Anthropic's path to profitability. However, significant portions devolve into circular commentary ('growth or die,' 'faster and better'), and several segments lack novel insight - e.g., the Clayton Act Section 8 discussion is explained clearly but is ultimately a procedural non-story.
You can't add expenses below the line fast enough to stop yourself making money. The only thing that matters will be the growth rate and the 27 and 28 projected revenue.
I think it'll land at 100 grand per engineer equivalent. I think that's what we'll. I think we'll give each of our best engineers $100,000 of tokens and in return we'll cut the size of our dev teams 30, 40%.
The hosts recycle familiar frameworks: the optimist/pessimist framing ('Pessimists sound smart, optimists die rich'), system-of-record moats, and PLG-to-enterprise playbooks all appear well-trodden. Originality peaks in specific moments - the nuanced argument that OpenRouter's niche product status limits Stripe's upside, and the detailed Clayton Act analysis - but much of the discussion rehashes prior show commentary and standard venture logic.
Pessimists sound smart, optimists die rich.
You know, I'm actually going to, I'm going to cancel my comment and disagree with myself. Actually, I think you'd be great because I'll tell you what you would bring to the table that I think a lot of these P buyers missed. It's this idea of mission clarity around growth.
The episode features two regular hosts (Rory/Lemkin and an unnamed co-host) discussing news without a formal guest. While both are seasoned operators with legitimate operating experience, the format is three knowledgeable insiders discussing deals and trends rather than bringing in new practitioners or founders directly involved in the deals discussed. This limits fresh firsthand perspective, though the hosts themselves are credible.
Speaker A: Your gross margin problem is my revenue opportunity for my colossus cluster.
Speaker B: I would much rather initially work for Elon than for Zuck. I think it'll be like the scale acquisition.
The episode excels with concrete numbers throughout: Cursor's $60B acquisition at ~10x forward revenues, Anthropic's $11.5B Q2 revenue and path to profitability, the $100k per engineer AI spend thesis, Workday's 5.3x revenue multiple in the Silver Lake bid, OpenRouter's ~100x trailing revenue valuation, and Lovable's $13.3B price at $600-700M ARR. However, some claims lack precise backing - e.g., the 'billion knowledge workers in the world' is rejected but not rigorously replaced with hard numbers in all contexts, and the Clayton Act discussion mentions companies but lacks SEC filing citations.
Cursor goes multimodal really early. It changes everything and rockets to a 60 billion outcome.
Someone who was hired with a million dollar package in 23 ended up making 51 million four years later.
The conversation features sharp back-and-forth and productive disagreement (e.g., Lemkin pushing on OpenRouter's niche status, the debate on system-of-record moats vs. growth, multi-threading the Workday deal implications). However, several segments lack follow-up depth - the Clayton Act discussion feels perfunctory despite being interesting, and some tangents (e.g., hypothetical Zuck vs. Elon analysis) drift into speculation without pushback. The hosts occasionally validate each other's points rather than stress-testing claims, and some exchanges feel more like storytelling than investigative interrogation.
In what sense, Jason? Just a genuine curiosity.
You can see intuitively how stripe get there from here, right, Is that, uh, you know, when you look at their existing business...
Computed from the transcript - who did the talking, and the words that came up most.
AGENDA: 04:20 Elon's Deal of the Decade: SpaceX Buys Cursor for $60BN 06:10 Why Cursor Was Surprisingly Cheap at $60BN 07:00 Why Zuckerberg Failed to Buy the AI Prize Elon Secured 12:00 Elon vs Zuck: Who Would You Rather Work For? 14:00 Will Microsoft or Amazon Now Race to Buy Cognition? 17:05 Stripe's $7BN OpenRouter Deal Creates Huge VC Winners 25:00 OpenRouter's Fatal Risk: Enterprises Don't Want 10 Models 28:15 Anthropic Turns Its First Profit on $11.5BN of Quarterly Revenue 32:15 Can Anthropic Really Reach $600BN in Revenue? 37:00 Why Every Elite Engineer Could Soon Get $100K in AI Tokens 39:30 Would Rory Buy Anthropic at a $2.5TN Valuation? 44:50 Silver Lake's $43BN Workday Bet: SaaS Isn't Dead, It's Mature 53:00 How Silver Lake Could Make $30BN From Workday 57:00 Lovable vs Higgsfield: Similar Revenue, Radically Different Valuations 58:00 Is Lovable's $13.3BN Price Actually Cheap? 63:30 Why the DOJ Is Coming After Andreessen Horowitz 69:00 Why A16Z Has "50 Legal Battles" Happening at Once
Transcribed and scored by The B2B Podcast Index.
Speaker A: Your gross margin problem is my revenue opportunity for my colossus cluster. Pessimists sound smart, optimists die rich. Only a fool denies that Elon Musk is wildly effective.
Speaker B: I would much rather initially work for Elon than for Zuck. I think it'll be like the scale acquisition. I don't even think this product will exist in five years.
Speaker A: You can't add expenses below the line fast enough to stop yourself making money. The only thing that matters will be the growth rate and the 27 and 28 projected revenue. Someone who was hired with a million dollar package in 23 ended up making 51 million four years later. A billion knowledge workers in the world. Absolute bollocks.
Speaker B: I think we'll give each of our best engineers a hundred thousand dollars of tokens. I had two board meetings in the last week where they finished the roadmap for the year. They're into 2027. If you're not into your 2027 roadmap, deep into it by August of 2026. In the agentic world, your team is not good enough to survive today.
Speaker C: This is 20 VC with me, Harry Stebbings, and Stay.
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Speaker A: You have now arrived at your destination.
Speaker C: Boys, we are back. We have some mega News. This week SpaceX closes the $60 billion all stock takeover of Cursor minting thousand x returns for the likes of Annie Partovi and Neo OpenAI's startup fund is a mega winner who invested 6 to 8 million dollars very early which Rory, I thought of you when you said before about Elon Musk, Sam. Billions of dollars through gritted teeth and many others thrive in Andreessen, most importantly netting huge returns. What do we have to say on this one? It's the closing of an already announced deal. Thoughts?
Speaker B: I just had three things. One is it's just super. You know, we've been doing this show about 70 something weeks, you know, or so on. So much has changed in the middle of it or maybe a third of the way in. It almost seemed like hersr was dead, you know, no one's portfolio companies were using it. I don't even remember if Claude code existed when we started the show or not. Right? It might not have. Uh, it, it sounds so crazy. I'm not sure it had launched. Right. So Cursor was super easy. Rockets to half a billion in revenue. Claude Code comes out and it seems like everybody's moved, like Cursor's dead. Cursor goes multimodal really early. It changes everything and rockets to a 60 billion outcome. I mean, forget about that. It started as an email client, right? That fun little thing from Hacker News. I can't imagine what a roller coaster it was on behind the scenes. This was not actually 100% linear progress to 60 billion. Pretty, uh, pretty crazy. I think the rate of, the rate of change and the one thing I just kept thinking is, and it's tough, it's how important it is to be beyond agile because I think so many teams would have given up on that journey, right? Oh my God. Fucking Claude code came out. I got to build my old LLM. I got to do the like. And it's just, it's so hard to keep up with the rate of change. And there's probably been three different cursors since we started. Other than the email client. That was my main thought. The second one is how it ended up not even being that expensive by the time the deal closed.
Speaker C: And you say that because it's going to be at 6 billion end of year and then you're paying 10x or you mean it?
Speaker B: Because TEDx forward revenues if you. And it went from something earlier in the show, it looked like it would be gross margin negative right when we started the show. Be like, well, cursor's a joke because they're selling a dollar's worth of tokens for $0.80 or $0.50 to, to the world. Of course it works, right? This was the classic thing that VCs would mock when we started this show and it was true. Right? Turn around. Everything from open weights and everything. It's a pretty darn good business model selling at 10 times forward revenue. I mean that's a. Elon was a shrewd buyer. The shrewd buyer.
Speaker C: I'm intrigued why Zuck didn't buy it. He's building the model capabilities With Alex and co, he's missing the enterprise capabilities. This would have solved that in the similar way that it solved it for Elon.
Speaker A: Yeah, interesting tangent. And yes, if the logic is, hey, you've got a whole bunch of compute, but not an obvious business on top, the two people for whom that's true are, uh, Meta and SpaceX. And you're right, SpaceX did it and Meta did not. Right, so that's. Yeah, at a high level. It's a fair point. But one of the things we pointed out in the agenda is SpaceX could move a little more. They didn't do one of these weird acquihire things. They just bought it like a regular old corporation. They didn't have any antitrust. I mean they actually filed for antitrust. They got quick clearance. They didn't have any compelling issues with that. I don't know if the seller would have had the same confidence that Meta would have gotten through. Right. Just given their doj, they just probably are going to have the DOJ more kind of crawling through what they do. So that would be one argument. It may also be to be very direct. No one else had the stomach for the bed in the way Elon does. And I mean, yes, Meta is relevant here in terms of fitting the characteristics of lots of compute, no compute business on top. But Elon has the biggest advantage, which is his stock is trading high. They're doing what, 20? I mean it's 8 billion last quarter in revenues, call it 30 billion growing round up to 50, what the hell, it's still 40 times revenues. Picking up a big asset as Jason says, At 15 times current revenues, maybe less than 10 times year end revenues. Dirt cheap for him, a net accretive day one. In a way that probably wouldn't be as true for Matt. I haven't thought about it all that much because frankly, until you mentioned it, I hadn't thought of that. But one of the things for me is if you zoom out, I'm just reflecting back on Jason's comment on the gross margin negativity. That's true. That story was true when it happened and it's still true today. There are challenging margin issues. When you reflect on the journey, the negatives that you can cite along the way tend to be true. They're correct, those were real. And when you look at an investment, the positives in terms of market trajectory just outweighed the negatives. It's easy to sound very financially smart and say, oh, in the end everything has to generate free cash flow. This doesn't have gross margins. So in the end it's worthless. But it's wrong because along the way, when you have a market that's exploding, like coding, that's a huge market. Remember, this is the biggest market for AI. 70, 80% of Entropic's trillion dollar market cap is predicated on this. If you have the number two player in that space and you're growing hyper fast, then even though, yeah, you got gross margin challenges, especially in a kind of optimistic forward looking market, the buyer's going to look past that and say there's only one or two ways to play in this space at a meaningful level. And it was just a perfect fit. Frankly, in a very different capital markets, it could have been a very different story. Oh my God. There's no capital. Oh my God, the gross margins. Oh, no. Free cash flow. Maybe you have to slow down and do a very different trajectory as Cursor, but in this market, they were able to go balls out, for lack of a better word, have those tough gross margin stories and then find a buyer who not only was willing to look through it, but actually had every ability to solve it. Because it's like your gross margin problem is my revenue opportunity for my colossus cluster. So it just shows the negative issues didn't go away. They just got swamped by the optimistic take. And that's why it's the old cliche we talk about. Pessimists sound smart, optimists die rich. Jason said it. There was probably some very tough days, but they had the guts to keep moving forward. And because the market's huge and uh, because frankly the environment is risk on, they've had an amazing result. Good luck to them.
Speaker B: And on the Meta thing, it's just a detail, I guess it's a parallel universe question. But I mean Zuck would have had to pay 80 billion. 70 billion in like a week. That have to be very core because don't forget what happened was Cursor was about to close around 2 billion at 50 billion, right. From Andreessen and friends. And Elon did what you have to do in that situation. What does it take? So he bid 10 billion more. Right. You've got a deal at 50. I mean Zuck did Instagram and WhatsApp like in an hour on the back of a napkin and paid high. Right. But I think Elon did even better. What's it going to take? They were already working together with Cursor, right? They're already working together. We're going to do the round of 50. Would it. How about 51? No. How about 50? 60? How about 60? Okay. And? Well, the deal might not happen. Well, what if we pay you 10 billion if it doesn't happen? Well, okay, I've removed all the objections from the deal. And, and I'll let you run the company the way you want. Right. I think it was three points. And they shook hands and did the deal. I mean, Zuck can do the same thing. He's done it at least twice. But you gotta want it bad to do it right at 80 billion. And he would have had to move even faster. I mean, Rory's of course, right? Elon had the ultimate stock and currency to do this deal, right? And the ultimate match. But to do any of these deals, I think you gotta be Elon or Zuck, because you gotta just strike this deal in a week at 60 billion. I mean, it's only a handful of people can do this, right? Only a handful.
Speaker A: Agreed. And I was reading, you know, a Smith, who's kind of a dem, left of center, but moderate centrist blogger who's not an Elon fan, just wrote a great piece about a year ago that says only a fool denies that Elon Musk is wildly effective. You know, regardless of your opinion on the merits of the party, he's one of, possibly the most effective person on the planet at getting shit done when it comes to industrialization. Physical AI and AI. And you know, from a standing start a year ago, he built the cluster and then he bought the product that's still on top of it. And he took SpaceX from literally a year ago being a, uh, really amazing rocket and satellite connectivity story to being, as the S1 says, at least in terms of the quote, future prospects, 89% an AI story. I mean, you saw his tweet, you mentioned it a year ago. You know, I've underestimated AI. Some version of underestimated AI. Time to go. He went from a standing start to owning more compute than pretty much anyone else and owning the most important product to fill that compute in less than a year, just over a year. That's just wildly effective management. It's a world class in getting shit done.
Speaker B: The other small factor, just thinking about it, we can move on. But imagine you are Michael a cursor, right? And things are going pretty well. You've got, you've got a term sheet from your, what, 24. You're a paper deca, uh, billionaire. And Nvidia and Thrive want to put in money at 50, right? You're not that cash motivated. You could take out a billion, right? Or 500 million. Right. Things are going okay. These are very rare deals. But even though working with Elon in a year might turn out to be terrible, I would much rather initially work for Elon than for Zuck. Personally. I would do it like I would be like, Elon is the guy I want. If I had to work for somebody, be Elon, I mean he is better than me. This guy is rockets electric. He does everything. And Zuck's firing everybody and going crazy because, uh, he doesn't have an LLM. Not that he isn't one of the greatest entrepreneurs, but I wouldn't want to work for Zuck, but I would want to work for Elon and that actually matters. It may be a mistake in M and A as a target, as a CEO, because we've all, when we've been founders on the other side, we've made mistakes here, right? I tell founders to ignore it, ignore the brand, ignore what you think the job is today because you have no idea in 24 months what the hell you're going to be doing. But it is incredibly emotionally important to founders to land in something they want to land in. And I would not want to land at Meta today if I was Alex at scale and I got 24 billion and I had a tough business, maybe, but this one man, I'll, I'll take Elon over that one.
Speaker C: Do you think Amazon or Meta go, eh, we'll take cognition instead. Is there a knock on effect for the second player in market which I think arguably now would be cognition.
Speaker A: I think it's interesting you cite those two. There's actually a quality of absolute imperative to do something, you know, who has to. And I think SpaceX had to because they had all this compute and it looked like they had to fill it. Now subsequently they've also been able to rent that compute to Anthropica, uh, and Google. I don't think it's nearly as existential for different reasons to the two you named and I'll name one for whom it is for Amazon. They're in the AWS business. They got lots of contracts with Entropic. They basically have the compute for Claude code. So they're basically getting the inference side revenue for that. They don't own the model but it's important but not imperative. They've never done a $60 billion deal that they're starting now. Meta, uh, that to me is more a, again unlikely. And the reason they didn't do it earlier is their core businesses at ads Business. It's freaking amazing. This is literally. I have a wonderful ads business. It kicks off north of 100 billion. I've chosen to do this new AI thing. We can pretend it's strategic, but it's really, I just frickin really interested in it. I don't know if you have to do another 60 billion deal on top of that one. So not as imperative I think just to put it out there, I'm going to name the one. The company for whom this market matters is Microsoft. Because remember, he's now long since gone and owns a basketball team. But Steve Ballmer would jump around the stage sweating, screaming, it's developers, developers, developers. And the fact that they've lost that connection with developers, that GitHub is now a trailing edge product is to me over the medium term pretty significant loss. I mean operationally the numbers are fine, it's a well run company. But if you wanted to name people who should want to own a leading state of the art coding product in this brave new world, clearly the number one person is Microsoft. Now the antitrust issues would be a longer discussion. But I don't think, in other words, I don't think owning the developer is existential for AWS. I definitely don't think it's existential for Meta. It's 100% existential over the medium term for Microsoft.
Speaker C: Eisner A fantastic tweet that said Satya should buy it and then make Scott Wu CEO of Microsoft. I thought that would be a rather ridiculous thing to replace himself, but I actually thought Scott would be a rather brilliant CEO, uh, of Microsoft.
Speaker B: My experience with big company M and A. Is that the idea that Harry, what did you say? That someone else feels like, you feel like they've got to. That folks have to jump in to respond to cursor, that everyone else. Yeah, my experience is that doesn't happen. It doesn't actually get everyone else to say hey, I've got to go buy cognition. My experience is that usually the other thing happens. I wanted to buy cursor, I lost cursor or I didn't even know I lost cursor because Elon swooped in. Now it pushes it up my existing priority list. That's how number two and number three get bought. Not because there's a panic for land grab, but because I didn't get what I wanted. That's when you got to be really thoughtful as number two because uh, that's when you get bought as number two. Number three. I really, when just number one just gets taken off the table. It's not so much a land rush. A lot of times acquirers are like, I thought I had more time. Maybe Satya is like, I thought I had more time with Cursor. Andreessen was do it at 50, I could do it 100 billion next year. I wanted to wait and see. And they thought I had more time and they didn't. So then they go by number two. The couple of times I've said on the other side, I don't know that it creates such a strategic arm race that everyone just gets picked off instantly. That that might be a VC partial myth.
Speaker C: There's another mega acquisition that happened this week. It's not quite the $10 billion that was reported, but open router, $7 billion acquisition by the Irish Paulson brothers royal brethren. I mean, what an incredible journey. Alex Atala, CEO, uh, who I just had on the show, he founded OpenSea before it's obviously the leading LLM RO raised a Series B. It was at $1.3 billion valuation just four months ago. So it's 5x that or capital G to 12x for Menlo and Andreessen. How do we think about this? It's widely reported now it's confirmed.
Speaker A: You can see intuitively how stripe get there from here, right, Is that, uh, you know, when you look at their existing business, they get paid a small percentage of the money flow to manage complexities, improve, um, collecting cash via cards and also by ach now and here they're going to get a small amount of the money flow to manage the complexities of picking models and running as an enterprise, using a single API to run tens and maybe hundreds of different models. So I can see at the conceptual level it totally makes sense. And a lot of their lift recently has come from even on their payments business has come from just their customer base being so AI forward that every time you spend money with OpenAI or Anthropic on a credit card, they get some of that money. So I can totally see how they get there. And again, it's some version of the same thing as the cursor comment. You can do the old intellectual. Oh, what are the barriers to entry for this business? Oh, over the medium term, there'll be lots of people and there's a ton of weenie router companies out there and everyone's building one. But it turns out in an early land grab when people are moving, remember, the meta market here is growing 10x year on year. If you take Anthropic's growth rate as the big picture comment here, right? If you move early and you build a useful part of the infrastructure, you will probably find an acquisition at a price that doesn't make any sense on a DCFTU basis, but makes huge sense to the acquirer because just like Elon will turn cursor into money cash flow far quicker than cursor could have turned cursor into cash flow. I'm uh, willing to bet Stripe will turn open router into money probably quicker than OpenRouter could do on a standalone basis. This is what happens in a crazy market is that if things slow down a lot of these, uh, the acquirer would run the buy versus this build and say there's no hurry, we've got five years when things are moving as fast as they are now. You're going to see in my view, until such time as you see the correction and the acquirer currency diminishes, you're going to see a whole bunch of people like Entropic say screw it, I want to be in world models. I'm just going to buy the card, I don't have time. Screw it, I want to be in Stripe. Screw it, I'm huge in payments. I want to be in the AI influence flow. Quickest thing I can do is spend $7 billion, some of it stock, get these guys and be rolling in a week. This is what you see. You saw it early Internet stage, you saw it back in times even before that. That would make you cry, Harry, if I even mention it, right? When things are moving really quickly in a build out, you just see these kind of amazing acquisitions where the value to the acquirer dictates a very healthy price. And it's one of the reasons why venture works. You go right out there on the risk continuum. But if you time it right, you can get these kind of returns and you know, well done a 16, well done Menlo. Well, well done Capital G. It's a
Speaker B: reminder you know how weird revenue is in M and A because if you're bought by pe, top and bottom line are incredibly important down to the significant digit down to sell G38 okay, if Workday goes private, exactly what its DCF will look like in 2032 is so important. The weirdest thing about M and A with big companies is revenue. So important to argue over multiples and the price. Like it's so important to price, but it's irrelevant because it's all about what Stripe can make out of open router. It's such a weird thing that your revenue going into Big M and A actually doesn't matter at all, even though it's probably the biggest input to price. But then it's like Stripe. What's open router doing? 70 million, 80 million today. Stripe does not care for that money. And so you often see acquirers will abandon even the existing revenue. Right. To do the revenue. It's just, it's such a weird paradigm. Two things. Rory's right. Uh, Stripe actually appears to be very good at acquisition. It's how it accelerated into crypto and otherwise they're good at it. The flip side, you could say is maybe they should be better at building these themselves. Right? That's the grouchy version. Why didn't you build it? But if you're good at M and A, and this is 5% of your market cap plus cash and you want it tomorrow, it makes sense. If you're good. You have to be good at M and A though, and, and then you do it. The counterpoint is I love open router. I talked about it on the show like six months ago. I'm a customer, I'm a user. Is brilliant. It was one of these pieces of software like 11 Labs, which is just instantly easier to deploy. It's just elegant. It was just a beautiful piece of software. But it's pretty niche.
Speaker A: In what sense, Jason? Just a genuine curiosity.
Speaker B: So Open Router, as I understand it, and I think it's right, is really strong in sort of developer type tools where you want a simple way to pick a model. Okay. Because you can pick any model. You don't need to get on Fireworks, you don't need to set up anything. And it's really, really, really strong with chatbots where like they don't have to be perfect. When you're talking with my Digital Harry or digital Rory, you don't need perfect outputs. Right. You could route between models based on availability and those are their two niches. Now let's talk about workflows with a lot of reasoning for bnb. When it has to be accurate, you're going to down spec to one or two models because you can't have model drift. You can't be routing from Kimmy to Quinn to 46 to Fable, and all of a sudden you're like B2B workflow that has to be perfect drifts from all of them. It drifts. Even just going from like one opus model to another, you see drift. You have to QA it, requalify it, fix it, test it. So for high reasoning models, people do frontier esque outputs, right? People don't rotate through 11 models and I don't think open router is the right product for that. And that's fine, they get that too. But I think Stripe is, hey, listen, any transaction on planet Earth we can take 2 point something percent of right. But it's not going to be true for open router. It's a niche, it's a wonderful niche product. But in the world of routing, which everybody does, databricks does repplit does it lovable does it vercel does it. It's a niche product with two really good niches. But this is the risk to Stripe is that they end up owning a niche, a successful niche product. And that's not their, their DNA is not niche, it's just not their.
Speaker A: First of all, I do think that's fair because you know, we internally agonize about this space and that was exactly what we're angsty about. And your framing is exactly correct. Like the positive. Let's spot the pot. The positive trend is as long as you have the frontier models trying to extract 100 billion in revenue from you this year and you're an enterprise, you're going to want a plan B at least to keep the thing honest. So you are going to want some kind of routing. But it's what you said that resonated with me, Jason, a little bit, which is, remember when cloud was starting, people were like, oh, I want to be multi cloud. It's really hard to be multi cloud here. Maybe I want to be multi model, but maybe I only want two or three models and therefore I don't need this kind of routing, uh, functionality. That is the risk. If your enterprise customer decides I need to flip between three models but not ten, then you write your value here goes down. I would imagine the deposit spin is your value here goes up to the enterprise. If you can build on top of just picking a whole bunch of normalization of all those options and try and commodify the model. So that's the kind of tension point. The more you can do that and the more you can service the people who don't care all that much, the better your business. But you're right. If J.P. morgan says I want more than just antropyc but I'm not going to qualify 10 models. I'm just going to work with poolside as my plan B and then offload the rest to something else, then you're right. Then you have niche, then you don't get that revenue.
Speaker B: Yeah. Like for example, like this week, Rippling posted their view as a B2B player of what models they use. Right. And they had it all. And they said in the world across rippling, we looked at two things that were best for us. Opus 4.8. It's an N minus 1 model but it's well trained with their harness. And then there's like there's price, performance and speed. And then I think they picked whatever GPT 5.5 medium or something and they said the rest isn't worth it for rippling today. Now that could change in 60, 90 days. So they down spec to two at a time and then they have to manage the outputs from these. And you may tune one set of workflows here, right, that are long reason in another. And even if you're rippling scale, managing 12 models is too much. If you're a dev tool and let people pick, so be it. Right? That's great. For open router or if you want to build into your own product, a fallback open router is a 10 out of 10 for this, like let's say something's down, right? Open router automatically falls back. But I think it's a niche product. But it could be a massive niche, you know.
Speaker A: Yeah, I'm m. I'm remembering the conversations now, uh, because you are right. The great thing about the core stripe product is all payments are equal and Visa is the rails for everything that might be the case. I'm going to check out that post because I mean one of the big questions will be how much pricing pressure enterprises can put on the closed foundation model companies and uh, how do they put that pressure on Because I think it impacts a lot, sorry, how we
Speaker C: go on in five years time. Will this be considered a successful acquisition or not? Bets on prediction.
Speaker B: I think it'll be like the scale acquisition. It will be the start of something that gets bigger whether this brand exists or whether even this product exists. Five years. I don't even think this product will exist in five years, but I think there's a high chance, more than 51% chance. It builds into a uh, 20 or 30% revenue stream for Stripe and that's enough. But does open router as part of stripe exist in 5 years? I'll bet you dollars to donuts 5 years is so much time and it's such a niche product. This, this product itself, if it does exist, it'll be deep in a dropdown menu on the top of stripe, like 11 layers down because it'll be subsumed into the whole sort of token Management, uh, platform. Right. They're tmp.
Speaker A: I don't know. I think that's, I think Jason's answer resonates with me is if it works, it'll be a, it'll be seen as a TAM expansion play. What's fun about Stripe right now is they're doing that acquisition which is very much a, hey, we don't play in the this space. Let's put a stake in the new ground. And at the same time they're talking about a PayPal acquisition which is very much, we own this space already. Let's buy these guys, fold them into what we already have and just make a shit ton of money consolidating. I think that's a clever strategy. I think they're actually playing a very clever hand. There's probably a one in three chance that they have a massive AI routing business in five years, but if they do, that's a big second leg. While at the same time if they get the PayPal deal done, that's the kind of deal you have a high, to Jason's point about if you're good at MA and good at consolidation, you probably have a high degree of visibility that you keep those revenues, you remove the entire gna, you get more of a two sided network because you have consumer wallets which Stripe doesn't have. And you've done core consolidation acquisitions. Doing them both together, provided you can pull them off, is super interesting in terms of building enterprise value. And they're doing it all private. Again, back to the comment. Doing what looked like public company size MA m and pulling it off while private. I know they got the um, investors to take Stripe stock in the open router deal. I think some portion of it was stock. And you know, the PayPal deal is more complex and probably requires more thought. But again, being able to do what is, I think a 40, $50 billion deal and uh, a $7 billion deal. Issuing paper while private is pretty impressive. Massive.
Speaker C: Stripe's corp dev team need a bonus at Christmas time. They are busy this year.
Speaker A: They are busy this year, but isn't everybody?
Speaker C: We mentioned margin pressure on foundation models. Anthropic turns its first profit on 11 and a half billion dollars of Q2 revenue. The business is getting better for Dario. This is also in a week where Gavin Baker said about Dario saying he believes that they will be the final private company. Did you see this?
Speaker A: We did. And let's separate the hyperbole in the future from the facts in the present. It's not surprising they're making money if you just go back to last year, they did 4.5 billion last year and I think that gross margins went from negative the year before to like positive 30 or something like that. Right on track. I think end of the year roughly 40. Right. When you have decent operating margins like 40% and you go from 4.5 billion in a year to 10 billion in a quarter, that means you have 4 billion of gross margin, right? And that's literally in two quarters. You can't add expenses below the line fast enough to stop yourself making money. So it's inevitable. I mean yeah, they 12x growth which means they probably 14x gross margin. If it continued to increase even slightly and the trajectory has been increasing, you're not going to 14x headcount are below the line training costs in six months. So yes, I'm totally not surprised. They are operating in composite. We had run numbers at the start of the year and it kind of came to that conclusion. I mean the interesting thing will be as they continue to grow, as they buy that expensive compute from Elon, if you remember that has a big price increase two months in, I doubt they will forecast for their IPO a base case of continuing profitability. I could be wrong, but this profit didn't surprise me. I mean it's amazing performance, it's amazing revenue. I mean revenue with any kind of decent gross margin cures almost all else.
Speaker B: I think the other question is as we gear up for an IPO which could be very imminent, right Is what numbers does anthropic get away with, right? You've got off balance sheet liabilities, right? You've got massive commits, you've got probably stock based compensation like we've never seen in the history of mankind. So if you get asterisks and daggers on your numbers, they will be jaw dropping, right? If they have to, if they have to to fully account for that. And some of that's non gaap. These off balance sheets, if they're going to be hammered like uh, like a poor wicks or someone for SBC or. And everyone's going to write up the horrific downside, right? But I think everyone's going to look through all the nerdy negative things you could see in the numbers, they're just going to ignore it, right? But I do think it's important that it get ignored. I think it's important for anthropic it get ignored.
Speaker A: And I think none of that shit will matter. To use a technical term. The only thing that matters will be the growth rate in the 27 and 28 project projected revenue. Provided the revenue comes, everything else will be fine. If the revenue comes, then you'll need the off balance sheet stuff and you'll have the revenue to buy it. In other words, all these off balance sheet stuff are, uh, basically, I promise to buy a whole load of compute from you in two years time because if my revenue grows 10x for two more years, I'm going to need all that compute. Well, if the revenue grows, you need the compute. You're happy to have it. In fact, you're insisting you get it. If the revenue slows down, then you don't need the compute. It all gets harder. So almost everything is going to boil down to what number do you want to write for the next two or three years? And then as you say, the stock based comp. No one's going to care. Because the reason you worry about stock based comp, it's because in a steady state like workday, we can cover that in a second. If you're giving someone 500 grand every year to show up and be a middle manager, they're probably mentally putting those RSUs into their comp and they think to themselves, I paid 400 in cash and 500 in RSUs and if you start giving them the RS RSUs, they're going to want cash. So it really is a cash number. So in a mature business, it's totally correct to worry about sbc, but the SBC numbers are here are going to be huge because all these people got grants and then it turned out to be worth way more than they ever thought. And yeah, the classic example, someone who was hired with a million dollar package in 23 ended up making 51 million four years later. That doesn't mean you'd have to pay the next guy 51 million if that person had gotten the million they signed up for. That's all the real economic stock based comp would take. The other 50 million is just dumb. L. You got lucky. It's not a run rate. I actually think it is okay in a hyper growth company to look back past a good slug of the SBC and normalize it out. And conversely, it's not okay in a mature company that SBC stock based comp in workday or salesforce, that's real money that people are spending. And it's a little bit unfair because you're kind of giving the hyper growth company a free pass. But they get a free pass, you get a free pass. And it's the same thing we said about cursor. You Get a free pass on margin, you get a free pass on off balance sheet, you get a free pass on SBC provided revenue go up. Once revenue stop go up, all bets off.
Speaker C: Once revenue goes up, all bets are off. What would it take in usage for Anthropic to hit the $200 billion in ARR plan for 2028 and then 600 billion in the next year?
Speaker B: The simple version is how many knowledge workers are in the world? All right, how many folks can take a subscription being generous? Is it a billion human beings? Right? You know, if anthropic has 100% market share at 200 bucks, that's 200 billion. If anthropic has 300% market share, that's 600 billion. I don't know, Rory's thought more. The 600 billion seems complicated, but you know, our demand for AI is only just begun.
Speaker A: You can see 200 billion which is the number, right? Once you start getting the 600 billion number gets really hard because no one ever looks at the big number. And I've just been doing some work on this, right? No one ever steps back and looks at the big numbers. I mean you said a billion knowledge workers in the world, absolute bollocks. Hard nosed comment here. US is typically 50% of the world's software budget because we're 50% of the world's high end knowledge workers. We're 25% of the world's GDP. So at a minimum, if spend tracks GDP, it's only 4x the US but every software company is typically 2x US. Why? Because the rest of the world can't afford the same software we do because they're poorer and they have more people at lower wages and less software. That's why we have crappy Internet when we go to Europe. So the truth is the hard nosed comment is this. You probably take the US knowledge workers spend and double it. There are 83 million knowledge workers in the US and then roughly 86 physical labor workers. So that's what you start with and you start cutting it down. And I literally was doing the math this weekend thinking about it, you start cutting it down real quickly. The truth is knowledge workers includes everyone in healthcare. I don't think we're not going to replace the nurses, it includes the teachers. Right? The sweet spot, the er, sweet spot of the whole damn thing is there are about 1.8 million people doing coding in the US and then including then QA and all the other, there's around 5 million people that do software related shit, systems, admin, Stuff all the rest of that. And they get paid in total grossing up about 600 billion a year. 200 billion means you're replacing a third of them. That's a lot. Remember we said this before, the single most important ratio and I asked you about it. Well, you thought it was. Jake is in a steady state. What's the ratio of salary dollars to AI dollars? Because if it's 50% of salary dollars, you can easily get to $200 billion. $600 billion is hard in coding where you can't get there. If it's 10%, then it's hard to get $200 billion across the whole thing. So it really boils down to in the steady state, how much software? Because if software is the tip of the spear in terms of max adoption, what do you think? For every $100,000 you spend on an engineer or $200,000 you spend on an engineer year, are you going to be spending 100k on AI, 50k on AI or 200k on AI? That's the number.
Speaker B: Yeah, we're testing it. The last 60 days are. Every single scale up is capping their AI budget. For real. It's not just Ubers of the world. Everyone's capping it because it's grown truly exponentially. Right. Everyone's capping it at 6 million a year, 8 million a year. Right. I think it'll land at 100 grand per engineer equivalent. I think that's what we'll. I think we'll give each of our best engineers $100,000 of tokens and in return we'll cut the size of our dev teams 30, 40%. Effectively. It won't exactly work out that way, but close enough is how it's going to work out. So there's 100 grand here for running inference 24, 7 with 10 agents in
Speaker A: parallel, for what it's worth. I actually agree with. That was my mental model too. And that points to a total. And let's assume it's not just dev engine. Let's give the sysadmins the QA guys. This would do the same thing for everybody. Same thing for Everybody. You get 200 grand of wages fully loaded, including all the benefits and 100 grand word of AI. Uh, but we cut 30% of you. That turns out to be terrifyingly about a 200 billion plus or minus market in the US next year.
Speaker C: No.
Speaker A: Ever. Ever?
Speaker B: Well, yeah, I mean, that's anthrax, Sorry, that's Anthropic's estimate for next year.
Speaker A: My point is this if you count all the heads and apply the Jason Matt, you get 200 billion in the U.S. which probably means you still struggle to get 350 billion worldwide. That's the town. And then you've got to go beyond software. And there is obviously revenue beyond software, but it's nowhere near as fertile and the percentage isn't going to be anywhere near as high. Yeah, but it's funny, that's exactly the number I come out with because you see the ramp data that says the top 1% of their sample, which in turn obviously is a biased sample of tech forward. People are spending 7k and then the median is spending like 100. It's amazing. The dispersion. And 7k times 12 is only 84k. So the top 1% of the most curated group you can imagine in terms of tech spend is spending. That's 1% for all employees. So you're right. That's the pointy edge of the most optimistic spend is $0.50 of salary $.
Speaker B: I think we're going to get to 100,000 in the investments I've made that are the best ones, the ones growing faster, especially ones that are pre2022,23. So they have a frame of reference. Reference. They literally are shipping two to three times faster. Only recently. Only recently. That was kind of bullshit last year, right? People would say that, but it was all performative, like token maxing. I had two board meetings in the last week where they finished the roadmap for the year. They're into 2027. These are my fastest growing, two fastest growing but not brand new companies. They finished the roadmap. They're well into the 2027 roadmap. So you're gonna spend 100 grand on your team to do that. But it's adding up to so many millions, it's overwhelming. So I do really think there's some. This 100,000 makes a. You could justify more or less. People will ratchet it, but I think it'll be. It'll be the new normal and you'll cap your team and it'll all be. That's just what the CFOs will do. 100 grand of inference. And you get to hire this many engineers. But the idea that they're pulling their 2027 roadmaps and it's not just performative, it's not just PRs. You want to invest in that up until the maximum where it works. Right. But the absolute numbers are just getting really big.
Speaker A: Yes.
Speaker B: I got to say, man, if you're not that way you're losing today. If, no, if you're not into your 2027 roadmap, deep into it by August of 2026. In the agentic world, your team is not good enough to survive today. This is your last chance to make changes. Listen, if you're, if you're open router, you didn't even have a 27 roadmap. It didn't even mean it because you're just remaking it day by day. But if you're running the classic playbooks of these, I can get this much done each quarter, this much done each month and you're not into 2027, you're going to lose to the competition. You got to be honest. How deep into 27 are you? Not deep enough.
Speaker A: Yeah. Jason always gives me these terrifying sound bites that I go back and think about. Because we did this survey, we tend to be fact based people. We did the survey of all our companies and we saw similar to the ramp dispersion which is some companies all in, some companies adopting but still dramatically less spend per head. I can't remember the average but it was dramatically less. What I didn't do and actually now that I think about it, I should do and I will do is go back and say if you could touch a strong correlation which you believe you should be able to between output and can you justify the spend, then you should be saying to the laggards you're just going to fall behind if it
Speaker C: goes out at uh, two to two and a half trillion. Would you be a buyer?
Speaker A: First of all, I want to be clear. I don't think the software market is definitionally the end of the time. I think the average knowledge worker won't have 50% of salary and things but they'll have a meaningful percentage. So the TAM is significantly bigger than just developers because you have lawyers. But I think lawyers won't look the knee guy who's pulling 2 million a year as a partner isn't going to be doing 200k's worth of tokens. He's definitely not going to be doing a million dollars worth of tokens. A lawyer would die before they give a million dollars of tokens instead of a million dollars of take home pay. So the market is bigger than software, but there's nowhere else that's such a sweet spot as software. So I don't want to be limited to 200 but I think the really challenging thing, I definitely want to be first out rather than second out in terms of going public, especially if you have Some kind of near profitability story or bouncing around profitability. I think it's a far more attractive strategic position to be going out as Entropic in the fall with a we've been profitable, okay, we're unprofitable again, but we're the winner in the enterprise than going out next year where maybe the growth rates have started to slow. But for Entropic in the public markets, and if you OpenAI, uh, trying to access the markets, then I definitely think they're in a strategically more challenging situation.
Speaker B: I think they've just capitulated to it. Of course, you want to be first to your point, right. I think OpenAI has had to get their house together. More executive turmoil, apparently a great last 30 days. Right. But first half of the year slower than its previously junior competitor. Right. And they've had to do so much to say, listen, we're going to go public second. And then we're going to have a comp out there. And the comp is what it is, is. And we may not trade with the hype that SpaceX and Anthropic did. And the world will not end. Like we will trade at a very precise number. We will know what we're going to go out at and the world will not end if we trade at 1.3 trillion. I just think that they've given up on worrying about that because ultimately Rory's right. It's much better to be first, but in the long run it doesn't matter. Right? You're just. If you don't need the capital, it just is what it is what it is.
Speaker A: But Jason, that's the sentence. I'm going to push a little. That is the sentence. There are no two companies on the planet that need more capital than these guys. Guys, in a world where you do need the capital, being second sucks because I agree, in general, you are correct, it doesn't matter. Two companies go public plus or minus a year and a decade later, no one cares. We've definitely seen that over the years. The thing that's challenging in this particular case is both companies still have enormous, many hundred billion dollar capital needs. In that situation, I would much prefer to be. I'm putting an asterisk around fear there.
Speaker B: I think you're right. But the thing is, let's say. And pick your number. Let's say Anthropica is public at 2 trillion. It really doesn't matter, right? OpenAI is going to be able to sell stock at a discount to its implicit valuation before it goes public. There's still enough capital. Let's say, uh, they're both worth 2 trillion, right. Implicitly, OpenAI is going to be able to sell stock next year at 1.8 people will do it. And especially if you have no stock as CEO in your own company, it's okay to sell at a small discount.
Speaker A: Yes, agreed. And look, I'm not catastrophizing here, but I think the interesting thing is if you're the smaller market cap company and you have the bigger cap, which right now OpenAI does because they have a m more ambitious capital need target. Now, would you prefer to be the guy trading at 1.5 trillion who only needs to raise 100 billion or the guy trading at a trillion who needs to raise 300 trillion? At some point these things become troubling and yeah, price clears all markets. This is the best new technology market we've seen ever. Perhaps. And if you are the founder in that market and even now the number two, you're going to be attract capital, but you just don't know the terms under which it happens. And going back to my comment, I think you will regret not being able to access the capital markets this year.
Speaker B: No, no, of course I agree. And I don't want to spend too much. My only point is the media and social media make a big deal out of this. Right? Who goes public first and who does better? I just think Sam and the OpenAI team have said this is, this is our fate. They could go public tomorrow. Right? There is enough people to buy these shares to go public. They've decided that while this isn't perfect, right. This is the best on the board and we're going to live with the doubt like it's not the end of the world. Like you can't solve every problem. Tonight they got to solve bigger problems. Right? The cards are the way they are. Right.
Speaker C: Jason, you said about management team Churn that the churn, for those that don't know, most recently was Denise Dresser, who was the CRO who left and Dali Rajic has replaced her. Uh, for those that don't know Dali, he's one of the most respected CROs. He was a fricking master at whiz and I think the best CRO or sales leader in the business. Who's Chad? Pete's says he's the best of the best. So I'm feeling a little bit more confident for their Codex and enterprise division today.
Speaker B: Yeah, it's just a lot of change. I don't know anything inside. I just think Greg Brockman took Over, right. And brought in the Wiz guy. Just had enough of the Salesforce crap. Right or wrong? Actually, if you look across all of AI, a, uh, ton of Salesforce executives have been recruited, right, to come in and help. And you can make fun of it like I used to make fun of how back in the day Salesforce hired Oracle executives because they took shots at Oracle. But you need folks to know to scale what is Salesforce at? 45 billion run rate, 50 billion run rate. I mean, anthropic's, uh, past that now, right? OpenAI has passed that. So you don't want to hire kids. You want to hire someone that has some idea how to play. So Salesforce is about it, right? But if you step back from it, I'd rather have someone from Wiz that is close to technology, that is in a hyper competitive space rather than asking how many seats of slack you want. It's just a very different go, uh, to market motion. Right? It's very different difference.
Speaker C: Jason, you said if you have not already hit your end of year, um,
Speaker D: goal in terms of product and you're
Speaker C: not well into 2027, you're behind. I'm making assumptions. I don't imagine workdays quite at the cutting edge like two of your companies at 2027 already hitting those goals. And Silver Lake circles a $43 billion take. Private bid for Workday. One of the biggest SaaS buyouts ever. We got two of the best SaaS minds in the business here, guys. What should we take from this?
Speaker B: SaaS isn't dead.
Speaker C: One of the biggest firms, one of the biggest buyouts. The stock popped 18% afterwards. Wow.
Speaker A: I think what you can take from this because the SaaS isn't dead thing is just too simplistic. I think what you can take that is a very financially oriented, wily, savvy buyer is willing to bet money that they can buy this at a constrained price, lever it and generate a return because the revenues are sticky enough to allow them to pay down the debt over five years and with reasonable multiple stability, sell it on and make a 20% IRR plus or minus. I mean, I ran the numbers. That's the bet. So it's not quote, dead. But what it is not is wildly exciting. What it says is this is the mature phase of an industry when it's not about wild growth, it's not even about untempered growth. It's literally about someone saying this thing is growing at 13% year on year. We can buy this thing for was it roughly five times revenues, 16 times trailing EBITDA. We'll probably leverage it two or three times, four or five times in EBITDA, but it's going to be a big equity check. And then you run the LBO model and you say you keep at a 35% operating margins for five years. You use all that cash. It's roughly 10 billion a year in revenue. So it's like 3 billion a year of cash. You pay down the debt and the interest and provided you buy Rice, you can make 20% and almost a 2x over 4 or 5 years. I look at that deal and I go, I'm torn because first of all, I think Silver Lake is wildly smart. It's very interesting when you run the sensitivities. If you pay like 20% too much, it dips down into the mid teens. It's almost the exact opposite of venture in venture deals, if you're in the right thing, it almost doesn't matter what you paid. You see Cursor for details. See OpenRouter for details. Right? This is the exact opposite. And this is fine precise financial engineering. If you're wrong by 20%, 30% on price, you know your IRR dips from 20, which is totally acceptable at scale to low teens, in which case you wish you hadn't done the deal.
Speaker C: Can I ask a question? Precise financial engineering for a 4 to 6 year hold period. 6 years ago ChatGPT didn't exist. Are you able to do fine precise financial engineering in a world where we move so fast?
Speaker B: I don't think system of record is. I think it's a moat, but I don't think it's a ticket to growth. This is, I think super important and it's something that everyone on X gets wrong. It's great to have a system of record which workday has, even with AI and LLMs help, it's very hard to churn or you just don't want to churn. But it sure as hell doesn't mean I want to spend more money with that vendor. That's their challenge. But it sure as hell means the five years are far more predictable than 95% than poor Monday, which we love, or others. We have no idea where Monday or even HubSpot will be in five years. At the S and P level, we know pretty much where workday is going to be 10 years, right? And so I think this growth versus retention is misunderstood. There is a little bit of upside in this deal which I don't know if it's part of Silver Lake's calculation. The CEO came back, one of the co founders came back and Neil came back. He came back, he hired his successor when times were easy. Just before AI he brought in a great knobs and dials co CEO, you know like our friends at Daniel at UiPath and others and realized if I ain't going to work today came back. So I don't think Silver Lake is planning on aneel like radically changing it but I think if he does there's real upside to that. Maybe instead of their 20% IRR could be a game changer. If he creates the agentic version of Workday they at least have the founder back in the saddle doing it. And that would make me feel a lot better if I were Silver Lake that I have upside but it wouldn't
Speaker A: be in the damn base case. Jason, you framed the base case exactly correctly. It's 5.3 times. In other words, what this says is financial minds will pay 5 times revenues for system of record growing at 13%. Anything that's not a system of record, anything that's not going as fast price accordingly because you are. There's no way you'd apply the same kind of leverage to for example a to do or uh, a task management or a project management software or a website building software. What this gives you is a sense of what the baseline is for best in class LBO takeouts. If the airtable bending spoons give you an idea of what it is. If you just. If you don't have that kind of system of record you get 2.7. If you're vaguely profitable and in a space, whereas Jason says you can predict five years you get 2.7. And what Workday says is if you've got 30% operating margins, modest growth, but you have a system of record where you really can believe in the next five years then if you're lucky you get 5.3 times revenues. That's the bid ask spread right? Now contrast that with the game for open router where they're going to get I think the trailing revenue is plus or minus 100. You know they're going to get 70 times trailing revenues. Which game would you prefer to play?
Speaker B: Workday has something that makes it a better deal for P I think than anybody else on the target list which is that it is a somewhat closed system of record. Now Salesforce is out there working their frigging tails off because there are a muchly open platform. You can build your own agents on top of Salesforce tomorrow and a lot of the hot GTM startups are built on top of Salesforce. They're not necessarily only on Salesforce, but it's open. Try building on workday. It ain't so easy.
Speaker C: Right?
Speaker B: It is like LinkedIn. Right. It is intentionally, uh, barely open. So there are negatives to that. Right. But it also means you're gonna capture more budget overall in your ecosystem than you would for others. So I it has more of a buffer against agentic damage to your growth than an open ecosystem has.
Speaker C: Right.
Speaker B: Open has negatives today. And so I would want system of record churn, impossible closed af. I want the most closed system that can't churn because the reason system of records aren't that great is because you need your system record. But if you're remotely open and, and you can produce a better agent yourself or a third party, the value will extract to the agent even if the system of record is retained. But workday's so closed, they've got a leg up, right?
Speaker C: Jason, how open is Salesforce?
Speaker B: They are a toll keeper, like a Shopify, but they're pretty open. Shopify and Salesforce are pretty open. The three of us, we can use OAuth to ship a Salesforce app tomorrow
Speaker A: just to prove that. Harry, really quickly is that, look, there's a bunch of companies even in pre LLM world like Gong, Outreach, Salesloft that are all effectively built on top of the Salesforce platform. You can't name the equivalent with any ease in workday. There's a few but. But it's much harder than some of the planning tools. But pretty much most. And it makes sense. Within the financial accounting system, everything gets sucked into the gravitational pull that is the GL and the accounting system. Right? So I agree. It's a good point, Jason. Whatever dollars are in that ecosystem, if they're careful and shrewd, workday will get most of them. If on the other hand, if they get too greedy and they don't invest enough, then the customers start thinking, oh my God, this is just not advancing, oh, over five years. Maybe I do need more of this agentic workflow on top. Maybe the smaller customers start evaluating Netsuite, start evaluating the next generation. Uh, even at the very small end, you've got the Willets, you've got the campfires, you've got the people like that. You can't be such a greedy bastard in your ecosystem that you incent people to start trying to move out. But Silver Lake are smart and Eel's smart. You could have this be a profitable self contained universe. But Remember, the most exciting version of that is you pay down all the debt in five years and you double your money for $24,000. That's as good as it gets. Now it's on a lot of money. You're probably putting in plus or minus a 20 to 30 billion dollars equity check because you're not going to get infinite debt. Maybe 20 billion. You might get 18, 15 billion of debt, which means you need a 25 to $30 billion equity check. So you're going to turn 30 billion into 60 billion, which on a multiple basis is not amazing, but it means you've generated 30 billion in gains and 20% of that in carry. So someone's m about to make $6 billion if they can pay down this debt and just knuckle down for the next six years. Go team.
Speaker B: Yeah. And Aneel gets to rebuild his company outside of the public company eye, which is slightly overrated because he has to hit the underlying numbers. But it's much better.
Speaker A: Instead of large numbers of stupid comments, he will get one very focused comment from one of the world's smartest investors. It's probably a trade up.
Speaker B: Just one last thing on this versus Salesforce. I just. It's just interesting. So we run Salesforce entirely headless. So we have our own agent, 10K, our own AI VP of Revenue. It runs Salesforce under the hood pro is. It makes Salesforce much more powerful than it ever was. Like I didn't log into Salesforce for seven years now. I log in every day because I have an agent con. It can connect anything. The agent, it literally can connect to any other agent, including competitors, including other data sources, data lakes, data, everything. The agent doesn't care. It's really a weird world. As a system of record or core system, do you want to be extensible and uh, open? Right. Salesforce has said you can be headless. Risks and opportunities because you make it much easier to abstract you away or to compete with you. Even while you may retain a few seats. Right. The logo retention may be high but. But it makes you have to run faster. Workday doesn't have to run that fast. Everyone can't run it headless and integrate any single thing or pull out all your employee data and push it into my own ATS or my own system or own finance. It's a shrewd deal because it's the best. It's the best moat out there with the system of record.
Speaker A: And uh, I go back to my comment. If it is a shrewd deal, it also by definition means it's the high watermark of what deals are going to look like. Plan accordingly, people. You get 2.7 from the Ben spoon and you get 5.7 from the silver Lake guys. And he pays your money. It takes your choice.
Speaker C: Lemkin, you have a buyout firm. Which other asset would you buy next?
Speaker A: I'd want to know who gave Jason money for buyout. Uh, I would give Jason money for Venture, but I don't see him as the spreadsheet guy.
Speaker B: I don't. I. Harry, I just think more and more about the fact that systems of record are going to retain their customers. But I think we, we just underestimate that. That's just not enough to grow. It's grow or die today, right? It's grow or die. This whole show, everything grow or die. Who cares about the stock based comp or anything at Anthropic? My God, it's open router 192x revenue. Just because your customers are prisoners does not mean in today's world they will spend one more dollar with you. In fact, back. The CIOs want to cut what they spend when they're hostage, right? They're like, okay, I want to spend 90, 80 of last year. What can we cut from our bill from the vendors we're stuck with? It's a. I got to think. But yeah, Rory's right. I'm not the best at the spreadsheet.
Speaker A: You know, I'm actually going to, I'm going to cancel my comment and disagree with myself. Actually, I think you'd be great because I'll tell you what you would bring to the table that I think a lot of these P buyers missed. It's this idea of mission clarity around growth. If you don't have growth of some sort, you're in a desperate race against the debt. And the best you can get is a mid teens IRR if you work there and you buy cheap. And remember, that's when you buy at, uh, 5.7 times revenues. Some of these PE deals were done four or five years ago at 10 or 12 times revenues for not as good a quality asset as workday. Today, the PE firm should hire you as their operating partner where for every new deal they do, you explain the facts of life. It's really clear here, people. The only thing that matters, you can't just stick it to your customers. If you don't give them value, you're going to get shafted in the end.
Speaker C: Rory, for me, the death spiral here is the exec high who's got no idea about AI and has a load of logos and has a load of middle management. And I think Jason would be the fricking best.
Speaker A: I agree. I changed my mind because you're done. If you don't, by the way, you
Speaker C: can click the link below to donate to Silver Lake Lampkin Ventures for the buyout firm.
Speaker B: Um, I don't want to spend money. On the positive side, if you look at it like a more S and B version, and I'm not saying how widespread is, but if you look on social media, a lot of folks are like, okay, I'm lifting off Airtable now. And they're like, bending Smooth is going to raise my prices 3x right? Let me start doing it now. And so it's just an extreme version of what you have to be careful with everywhere, right? I mean, bending spoons may lose 20% of Air Table's customers who finally spend a week lifting off of Airtable, but when they triple prices, it's a good deal for Bending spoons, but it's going to happen a lot faster than workday
Speaker C: growth at all costs. On the consumer application side, two big fundraisers from Higsfield who raised at a $5.5 billion price from DST and they hit 700 million in ARR. And then you have Lovable, who raised a new round from Menlo. They're around the 600, 700 million ARR range. 2 raising at a $13.3 billion price. Big price divergence for very similar revenue numbers, which I find interesting. Guys, we've talked about these companies a lot.
Speaker B: What.
Speaker C: How do we think about them?
Speaker B: Well, you know, on the Lovable thing, the thing I was thinking, I mean, it's so much so crazy since when we started the show, right, And Lovable and Replit were both raising like 2 billion. And we're really terrible products when we started the show. Now, they're great products. They're truly generationally great. I do think today engineers and developers will mock me for saying this, but I do think that they deserve us. Arguably a, uh, somewhat similar to be in the cursor conversation in terms of stickiness, strength, capabilities. They were not when we started the show. Did mend though, pay up a little bit as an existing investor, right. Who was already in at 4 maybe. But is that multiple that far off, the cursor multiple that we just saw? It's not radically off, is it?
Speaker A: Yeah, a lot of it. For the end of the year, it's probably a little pricier, but whatever.
Speaker B: But it's not as out of whack as it might have seemed With Cursor as a comp, these platforms are becoming. One thing is they're becoming very rich. They're very good now, right? Cursor's, they're very good. They can do so much more than they could six months ago. There's so much more complexity. I mean Cursor launched Origin, right, which would bought graphite or whatever. It's going to become a GitHub, um, entire workflow replacement in a couple months, right. I'm closer to Lovable but they both just launched automatic deep pen penetration as part of their products, right? So you can go really deep on security. So these aren't just little like little hacks a year ago and it also makes the startups harder to beat them out, right? As these become these Cursor and Lovables and replicas become true platforms. They're great software today. So I, when the Cursor deal was announced, our jaws dropped. Now it's a comp, it's just a comp and I don't think this is such a bad comp for Lovable to Cursor. I mean maybe, maybe that sounds wacky but, but that was the one one I thought, you know, Higsfield's cheap, although when the deal was done it was at 500. So it's funny in today's world by the time the deal announced it's at 700 million. So it's still cheap. But like that's what happens if you don't announce a deal the hour the term sheet is inked, right?
Speaker A: And you guys know what both of them have done really well is parlay. That kind of massive bottom end demand for AI in Lovable's case for website building and coding and Higgs Field's case for video, you know, start with a PLG motion and then M, you know, add mid market and enterprise products on top. It's a well trodden path. It was well trodden in kind of the SaaS days. We did a bunch of that. It all works. You build your top of funnel and then over time you just add the enterprise features. But they've both done it really well. And you're right, Lovable have punched their way into being a big picture coding alternative. There's different ways of going at it. You got the cognition style, you got the Cursor style, you got the Lovable replace style. They're not direct comparables but in the big picture comment of the thing AI does best is write code Lovable is a tool that uses that to write a lot of code. So it's got a lot of lift. And yeah. So I think they both built good enterprise business on top of good consumers. It's not as Higgs field and I know you guys are in them so you know much better than me. I think there is clearly a market for enterprise video. It's a good market. It's not as perhaps deep as the coding market but. But you know, great to see them do it.
Speaker B: The one meta learning for me is I do think took me a little while to see this. I do think these products today, not forever, maybe only for six months. Right. Or who knows. I do think they now are defensible and have moats. I mean for example Higsfield, I was one of the first 10 customers. I think what could you do? Make a four second video using Kimmy or Quinn? Who cares? It was a great way to do it because I didn't even know how to use a Chinese model. Okay. But that wasn't particularly defensible. Now you can make a full length motion picture picture and you can do it another way. It's just so hard. And now that on um. Love Reppable which we. Even though I'm a user for you. You could have made fun of these products when Harry invested when we started the show. Now they really can almost build production grade highly secure apps with everything across. Like it's just so. I know we're building so quickly and you better be into your 28, 29 roadmap or you're failing. But they are starting to get these layers of moats and the folks that work at these companies are so smart. Right. Hicksfield is like the smartest mathematicians in. In Kazakhstan Lovable and Replit have become talent magnets. I mean I know the team at Replit better you walk into. I mean these are the smartest people that Amjad could recruit for years. And so these layers are not impenetrable but they start to get thick and crusty this crust around them. Right.
Speaker A: Staying with that because I think you had that moat coming. I think you're exactly. Because there was a whole bunch. Oh, what's the moat? I think the truth is in any new software market out of the gate moats are. But the companies that execute and get traction you accrete moat over time. I mean just to give two historical examples, the Netscape browser wasn't that early on, it wasn't that hard. But as yet you parlay that into other things that ultimately you Only got acquired for 10 billion which at the time felt like a failure, oddly enough. But the initial thing was relatively simple. It got complex. I mean the Ms. DOS product and the classic example is Magnet. The Ms. DOS product was mind blowing. The same simple but over time you just accrete more and more value. And the same thing's going to happen here.
Speaker C: Yeah.
Speaker A: I mean will there be some guys who stumble along the way? Of course there will. But you're right Jason, if two years ago it is probable that someone could have built a lovable competitor with the features that Ed had relatively quickly as they add more and more features that just gets harder and harder.
Speaker B: Yeah, I don't know that that was obvious six months ago that this would happen. I don't even know it was obvious to these companies we're talking about that it was obvious, right?
Speaker A: Yeah, uh, yeah, I think going back to my. It just shows, just push on forward, add more stuff for your customers, revenues grow, good things happen.
Speaker B: If you're faster than everybody else. Yeah, you just have to be faster and better, that's all. Just faster and better then it will accrete.
Speaker A: Faster and better is a more tangible thing than thinking some kind of. I mean yeah, there are businesses that are much more moat central, right. You know, massively high ip, you know some obviously the model companies to some extent and definitely things like the bioinformatics companies there. But there are also business that will become wonderful businesses where the moat is as you say Jason, faster and better. And you just got to know which game you're playing.
Speaker C: Speaking of high IP businesses literally like three weeks ago etched raised at uh 10 billion. Today they've announced they've raised 700 million at Ah 21 billion from Jane Street, Kleiner Sequoia Andreessen four weeks after double the price.
Speaker B: It was a good month Harry. You only need one great month to raise today. Whether you pre seed or north of 30 were you used to need three to four good months to raise now. Now you just raise on the one. Listen, I don't know the details of the deal. I mean Jane street wants to be a customer too or something, right? It's not that they're suspect, it's just you never quite know how it's all tied together. So that was the only asterisk I had in the deal but I don't, I don't know the details.
Speaker C: Boys story have I missed that we should discuss.
Speaker A: There's one that I don't know if you missed while you were vacating there Harry, but the Department of Justice is picking on poor Al Andreessen because of these overlapping boys boards.
Speaker C: I put it in, it's in my schedule. Thank you for mentioning the vacation.
Speaker B: But, but what's, why is it, what's the story behind the story? There must be.
Speaker A: And I did the story because, yeah, I, I, you know, I often think one of the jobs we try and do here is let everyone in. Our, you know, people who listen know what's interesting this week, right? And I will admit this time yesterday, I knew exactly Jack. I was like, huh, what gives? I looked at this and I'm like, why is. Let me say something cynical and then retract it. Why is. Is the Trump administration picking on Andreessen Horowitz? One would have thought that there is honor among thieves and gratitude. The definition of an honest politician is when he gets bought, he stays bought.
Speaker B: Yeah, Elon got his deal done in weeks. His $60 billion deal done.
Speaker A: So I did the research and it turns out that this initiative, no surprise, was actually kicked off in the prior administration, which frankly was much more willing to get involved in business and kind of trying to them what to do. What's happening here is. Zoom out. There's something called the Clayton act, which I think in the early 1900s, an antitrust act, Section 8, that basically says individuals can't sit on two boards of companies that are competing. And there's all sorts of definition of how you define compete as a de minimis threshold. And that's on the statute books. It turns out under the Biden administration, the doj, I think it's the FTC within the doj, uh, but don't quote me, had actually made some actions on that. There was a couple of general business folks who were in overlapping boards. And interestingly, Thoma Brava, they had a couple of companies where in one case, I think they'd spun off a separate company from an existing company. So they had a lot of overlapping boards. The DOJ kind of got on them and eventually they said, we just take the board members off. This is a thing, this is apparent. And, uh, it's a low consequence thing because what invariably happens is if the department just comes around, you just pick the less interesting board and you come off it. And what sounds like what happened here is even though, as I say, you'd have thought the administration change would have killed this, apparently as part. Remember when fivetran and DBT were merging, the kind of DOJ had to look at that because there was antitrust issues. And that got true and it was Passed. But as part of that, it kind of the light went on in someone in the Department of Justice head that says, hmm, m. Do we have a Section 8 Clayton act violation here? Because Andreessen's on the board of Databricks and they're also on the board of. I think it's five tran. And now they're competitors. So now this has been percolating and now they're investigating. This is one of those things where I know why the law originally exists. It's all back to JP Morgan and overlapping boards and the antitrust and whatever. You look at this and you go, really? Is this the biggest fish you have to fry? But my guess is it peters out into some version of the venture firm. Just saying, we'll take off the board member on 5Trans. What now? It's interesting. There are ways you could contest it if you gave a shit and wanted to litigate. There's all sorts of things. Because it actually said the legislation says individuals can't be on two boards. But it's not as clear on can two separate individuals be on two separate boards. There's a whole bunch of reasons why you could decide, if you had the stomach for it, to litigate and see, would the Department of Justice back off. But the truth is no one's gonna bother. I shouldn't say no one's gonna bother. It feels to me like if this thing rumbles on and the Department of Justice doesn't back off or they don't decide the competition issue is de minimis at some point, if it got really serious, is my point, no one's gonna get into trouble for this. If it gets really serious, they'll go, okay, we'll take a board member off.
Speaker B: Yeah, it's probably a non story in the end. Thinking through more. Right?
Speaker A: Pain in the ass, though.
Speaker B: There is a remedy here. You resign, right? It's not done.
Speaker A: If you're the compliance officer in Andreessen, you're wasting a lot of your time on this. But you might. A non story is a.
Speaker B: The only weird niche thing, but classically you might ask the founders if they're okay with it of each company. Maybe that's not even a, uh, permanent permissible out under the Clayton Act.
Speaker A: It's not, actually. The funny thing is, to your point, you're exactly right. And it's a very interesting example. This is an example of. You and I both know that that's the acid test. Because we would be worried about is founder A pissed about founder B because are we damaging the other company by this information. But the classic antitrust thing is all about consumer damage. And what they're hypothesizing, absurdly, thirdly, is that the databricks guy and the fivetran guy get together and they say, why don't we raise the price of tools, of AI Tools, and we'll stick it to all our consumers like JP Morgan and B of A and whatever. Right? And that's so far from what's happening. And this is the problem. You pass a law for one reason. To prevent U.S. steel from raising prices in 1909. And here we are in 2025, 2026. And do we really think that Databricks and 5 Tran are DBT are colluding about the price of data tools? You're right. Uh, the logical test would be founder A. Uh, are you cool with this for founder B? And if they're cool, we're cool. But it turns out that's not the way we write laws.
Speaker B: Yeah, I mean, if Martin Casado had to step off the board of 5tran after exiting cursor at 60 billion, it's probably okay, given their position in databricks. It's all right. That guy just got us a $60 billion exit. We're sitting on 200 billion a Databrick bricks. Five tran. Good luck. We'll switch to an observer seat.
Speaker A: Yeah, anytime you want.
Speaker B: Not the. I'm gonna move to observer status. Like that doesn't work either. You got it.
Speaker A: Doesn't work either. They actually thought of that. They're literally like, Mr. J.P. morgan can't bring his big banker nose in 1909 into any of the meetings. Yeah, I know. That's what we're trying to solve.
Speaker B: So be it. Just CC me on the updates.
Speaker A: Genuine comment here. It's why, and this is a serious comment, it's why when we talk about all these regulatory regimes for other things, things, you have to remind yourself these regimes go on forever. Right? And if we pass some law about AI regulation now, you've got to be really careful. The unintended consequences, you know, months, years and decades later, these. Once the regulatory law is passed, it doesn't leave.
Speaker B: You know, one last thing in all seriousness, at Andreessen Scale, and everyone has to take the series 62 and your bro. There's probably 40 or 50 legal things going on in the background at any given time. Right? It's probably not even four. It's probably like 40. They don't even talk about this one. Right. It's time it's mentioned. Let me know if I got to do anything. I got to. I got to go to that pasta lunch with Michael for, uh, for the closing lunch.
Speaker A: The $12.
Speaker C: $12.
Speaker B: $12. Yeah. Let me know if there's an issue, because there's like 50 other lawsuits. Everyone's coming after Andreessen, right?
Speaker A: Yeah, it's the old no conflict, no interest comment. Exactly. They have lots of interest, so they have lots of conflicts. It'll be fine, boys.
Speaker D: Thank you so much. That was awesome.
Speaker C: I love that.
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Speaker C: straight to the breakthrough.
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