All right, everybody. Welcome back to This Week in Startups, This Week in Venture Capital. We have three shows, a little bit of both. We posted a This Week in Startups feed. That's been around the longest, but we do three distinct shows every week: This Week in AI, This Week in VC, and This Week in Startups, and they each have a corresponding newsletter that we're working on. We're hiring, looking for two or three great writers. So, we have a big docket today and an incredible list of guests. Lon, we obviously are going to get deep into Anthropic's S-1, which dropped recently. Let's, from a venture capital perspective, of course. Let's intro our amazing guests.
Sure. First up, we've got DA Wallach. He's the co-founder and general partner of Time Bio Ventures. They're a life sciences and healthcare venture capital firm. We've also got our good friend Dave McClure, managing partner over at Practical Venture Capital. He's the managing partner over there. It's a firm focused on the venture secondary market. Finally, we've got Ben Black, the co-founder and managing director of Aadian Ventures. They're a firm that invests in venture secondaries and they run SPVs. Jason,
Got it. All right, let's get started with our first story.
We're going to talk about Anthropic, of course. They filed their public S-1 on Monday for a NASDAQ listing as ENTANT with the price range and share count left blank for now. Revenue for the first half of the year came in at 16.3 billion. That's up 14x from around 1.2 billion in the first half of 2025. Q2 this year saw an operating profit of 974 million. Net loss was 80.7 billion, but 72.4 billion of that was driven by a non-cash accounting charge on convertible notes, derivative liabilities, and SAFEs, which were marked up as the company's valuation rises. The Wall Street Journal reports that Anthropic aims to go public the week of November 16th, raising a hundred billion or more at a valuation of around 1.5 to two trillion. So DA, we've got five or six subsections here. Many different ways to go. What stands out to you about the Anthropic S-1 and this story?
Well, I mean, I think like with everything that's happening in AI, the hard part is figuring out what's sales pitch and what's reality. And obviously this was timed and positioned in such a way as to sort of comfort the market as to the company's, you know, profitability or potential profitability. So there's of course been this raging debate over, you know, whether inference is profitable, how much money they're losing, and I think the clear intention of the timing and the way this was all framed was to sort of put everyone at ease, say, look, we're sitting on a ton of cash and we're not spending as much as you think we might be, and it's all going to be okay.
Did they accomplish that task? Is everybody... I don't know what the hell's going on. You know, it's like you're seeing these little fragmentary views of the elephant every week and every Gavin Baker interview and every All-In podcast and whatever, but you still never get to see the whole elephant. So, of course, that's what investing is. You got to make sense out of fragmented information and try to paint a picture of what's happening. But I still have no idea what's happening,
which is very similar, by the way, to poker. You are trying to make really good decisions with partial information, right? Like I know my hole cards, but I don't know yours or the other seven people at the table. Maybe I know three cards on the flop, but I still don't know the turn and the river to come. So, I think that's actually a great way of framing it. Dave, when you saw the numbers drop and you start unpacking the hand, do you feel more bullish on the AI trade? Do you feel like this is making people more confident in what's being built out here and the sustainability of it? Or do you feel like you have more questions rather than answers?
I feel like they did themselves a favor. You know, I think there's been a lot of concerns in the last quarter that revenue might have been plateauing. I think we still have those concerns. You know, questions about whether OpenAI is taking share, whether open-weight models are taking share. The company looks like they are profitable, looks like they've been, you know, on an operating basis profitable for the last two quarters. It looks like capex spend is crazy. That's, you know, over 500 billion dollars of capex. I don't know over what period of time, but, you know, hundred billion dollar plus commitments to both Google and Amazon which are locked in.
Well, maybe unpack that for a minute then, Dave. Like, if that's the first thing that came to your mind is crazy, how does one go from crazy to sustainable and connect the gap between capex spend and revenue and profitability? Take a moment there.
If they had gone public last quarter, I think everybody would have been happy with putting a two to three trillion dollar valuation on the company. But if you look at, I don't know if we can share the graph of ticker trends. This is Anthropic revenue. This is OpenAI revenue.
Okay. So when we're looking at the Anthropic revenue,
this is company-wide annualized revenue run rate. We just did a story about this in our newsletter. Actually, this is R as in a pirate, ARR, when you see that, which is not to be confused with ARR with three Rs. Annualized run rate is typically done by taking the last month or the last quarter and annualizing it either by that period of time, 12 or four.
And here what we're seeing is it's flat at 76.8 billion in ARR. And you see here, even on this website, they put ARR, which would lead you to believe it's annualized recurring revenue. Annualized recurring revenue is for subscription products like Netflix or your Verizon account. It's distinctly different than this. So, what's your takeaway here? Obviously, we see flat, but what is that based on? Where did they get that number?
You looked at the growth from January to July, you'd be like, 'Holy, that is crazy growth.' Like that's almost hyperbolic. But then it tailed off a little bit and people were wondering, like, why did that tail off? Was that because of OpenAI releasing models that were more competitive and taking share? Replit recently announced they've been switching their default to OpenAI instead of Anthropic. Is it because open-weight models are taking share? I would still say that Anthropic is...
Or maybe there's a data problem here.
This website doesn't have, like, who knows where they're getting their data from here.
Yeah, I think, you know, my partner just did a teardown of, you know, the Anthropic S-1 and it still looks like they are growing. I think they added, you know, at least five billion of new revenue in the quarter. So I'm not concerned that Anthropic is not growing, but they're not growing as fast. And I think you'd kind of want to look at that and compare that to the capex spend and can they just, you know, keep up with the spend that they're doing and is that revenue going to continue? They had previously been talking about 200 to 300 billion kind of run rates by the end of next year. I'm not sure. I'm still a believer that they're going to hit 300. I might guess it's going to be between 150 to 200 next year. We'll see.
But they did kind of answer a lot of questions about profitability that seemed like they had profitability under control. I think I'm still a believer in Anthropic probably at one and a half trillion, not at two or two and a half trillion. That's just my, you know, hot take.
All right, Ben. Your takeaway when you saw the S-1 and the ensuing discussions.
When I saw the S-1, I really was so impressed with how much analysis could be done in such a short period of time with AI. There were so many analyses I could barely keep up with them all. It was like in-the-mouth analysis, but really, you know, when I read the S-1, I said, you know, we need new measures, that, you know, this is really the first time we've had financials from a company that does what Anthropic does that are getting now to be torn down by public market analysis. And how the public market analysts, I say with private companies, this is the moment where the rubber hits the road. And right now we're just seeing literally like the first inkling of the way that we're going to analyze these companies. We're still just like what you did. We're trying to take SaaS analytical tools like ARR and slap them on a completely new type of business model. It's going to take a while before I think that the world of business analysts catch up with Anthropic and OpenAI, where essentially you're selling compute at some sort of margin and you're selling it across multiple models that have different values and different costs, all of which are falling. And I frankly am not sure I understand this business yet. And I think that's the biggest takeaway I have is that, you know, we have to have a whole new set of measures for these businesses that really help us understand what's going on, because I think the S-1 can be characterized in one way by one group of people, another way by another group of people, and who wins the framing in the next two weeks is going to determine whether or not 1.5 trillion is a good number or not.
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Yeah. Well, the framing is pretty obviously here. The revenue is surging.
That's something we know. And they're profitable and they've got a mountain of cash. So if I look at those just three factors,
Well, revenue is surging, but not as fast as it was earlier this year. Right.
As the number gets bigger, it slows down a bit. So you can't expect to 10x on, you know, 16 billion. It's not possible. It has never happened in the history of it. So it's going to slow down. The revenue is extraordinary. It's the fastest growing company in the history of business. The cash position is extraordinary. They've barely touched their cash. And so I look at this and say, we've got the greatest business in the history of capitalism ever built.
Wait a second, Jason. The greatest business? I thought you were saying last month with SpaceX. Isn't that still the greatest business?
I don't know if I said that. I think it's the greatest entrepreneur across a series of different businesses. This is one business selling tokens, and one business selling tokens to be profitable in. But this company was formed, I believe, in 2021. Revenue turned on in 2023. So to go from zero, you know, to whatever the annualized run rate will be after Q3 data comes out, 80, 100, etc., and to have a ton of cash and to be profitable at this point is just extraordinary. I thought they would have been losing a ton of money. So I think this is the greatest business created by humans on planet Earth ever.
I wonder if we're underestimating some stuff here, though. I had dinner with my friend Aaron Battalion. He was formerly the CTO at LivingSocial, and he was saying we're not even measuring the right stuff. He's saying with all the potential for, like, you know, breakthroughs in mathematics, in medicine, in a whole bunch of areas, there's potentially new lines of revenue that we're not even measuring. Like, what if, you know, either Anthropic or OpenAI solves cancer, resists aging, figures out new breakthroughs in other areas? I think DA was actually suggesting there's some stuff coming that people are showing off their lack of concern.
We can talk about the Anthropic AI releases later maybe or now, but I was saying to Dave before this, the craziest thing that's happening, you guys may have heard about, is the AI engineers are now taking up smoking, and this has become a way of... this is a very positive... if they're hitting darts, that's a very positive sign. Right.
So they're smoking cigarettes and they are doing so as a way of signaling how confident they are that AI is going to cure cancer.
So I would view this as a very toppy signal, you know, when people are willing to literally commit suicide because they believe so much in their religion.
It's interesting. I'm not sure we've ever seen that. Like, no, I think this is the buy sign. It's the ultimate buy sign. They're literally willing...
Yeah, to ski without a helmet. They're like, 'It's fine. It's all on the line.' Now, Jason, and it didn't occur to me until you said, 'This is the greatest business in the history of capitalism.' The actual greatest business in the history of the stock market over the past hundred years, as you guys may know, was Altria, Philip Morris.
And you go, well, why was that such a great business? Well, enormous gross margins and an incredibly addictive product with virtually unlimited demand. So, no churn.
At least 10 years ago, the number I heard was still today, a billion cigarette sticks sold every day around the world. One billion. So, I think the fundamental question for Anthropic and all the players in this market is basically, is intelligence the new cigarettes? Right? So far, a little free sample. The drug dealer's given a free sample to every company in the world and everyone's trying it and they're trying to figure out, is this something I'm going to be using for the rest of my life and how many packs a day, right? And I thought the most interesting number in the S-1 was this 0.1% figure. You know, they basically said, I don't know if it was their top customers or all of corporate America, but they said basically the users of our intelligence are spending, you know, roughly a tenth of a percent of their total operating expenditures on AI today. So, you can think of that, I think, in two different ways. View number one, which is the one they were trying to present, was you've barely scratched the surface. Think about how much headroom there is on that number. I mean, if you just double it or triple it, you can easily start to see how we get to a couple trillion dollars a year of spend. On the other hand, it does to me complicate this sort of Jevons paradox framing of this whole thing because I would ask, well, why aren't they already today spending 1% or a half a percent? And, you know, is what's keeping them from spending at that level that the cost is too high or is it still a utility question? And I guess my hypothesis would be it's mainly a utility question. And I'm going to say the thing that everyone has to say before they ever defame AI, which is, 'Oh, but I use it all day and I love it and it's so changed my life and my business.' You have to say that so you don't sound like a luddite. But why aren't they spending two-tenths of a percent today? Because it seems pretty obvious that this is something you have to be experimenting with extensively no matter what your business.
So wait, why aren't they spending 2% on...
On cloud, on intelligence broadly. You know, I mean, if they're spending a tenth of a percent on cloud, you need the right people to implement, right? And then you need the right projects.
So, and 2% of a company making, I don't know, sorry, sorry, right now they're saying one-tenth of a percent of total budget going to AI.
At which companies? Fortune 500?
For, you know, whatever, corporate America.
So I think it's because there's a... I think the number is 2% AI spend at the top companies. So I think if we chop off the laggards and we say one or two percent's the right amount of spend for today, I just think it's probably the Fortune 100s, Fortune 500s are actually spending tens of millions, I would say hundreds of millions in tokens a year. That's like what we saw Uber was spending.
It's still a small number. I mean, I think there are a couple questions. One, is the addressable market what they're spending on SaaS, right? Is this just going to eat their SaaS budget?
It's got to be double SaaS. So is it going to start by eating their SaaS budget and then eat more, or is it going to be incremental?
I mean, I think like, you know, you have this other major uncertainty here, which is that everyone involved here is doing the rational thing. So Anthropic is doing the rational thing to pre-order all that compute, even though it might put them in a tough place. Every corporate CEO is doing the rational thing to do a bunch of pilots and spend a bunch on tokens and figure out what this can do. The question is going to be, are these rational actors who are both ramping up their AI activities going to be doing so at rates that lead them to meet at the same level, right? I mean, ultimately what matters here...
Supply and demand. I got it. Yeah.
And right now everyone in AI says, 'Oh, we can't meet the demand. The demand's too high.' But then I go again, well, they're only spending 0.1%. The presumption in that comment is typically if the price were lower, they'd be spending more. In other words, when you say this is supply constrained, what it's suggesting is that the supply constraint is leading to...
I think it's meatsack constrained, DA. The people, the meatsacks at organizations are not able to deploy it. It's too heavy for the average employee. The meatsacks are blocking this. And then if you look at a company like, say, Uber, which adopts the technology pretty fast, they burned all their tokens in the first quarter famously and then were like, 'Oh, what do we do now?' They just put all of their employees, I think it was 30,000, on OpenAI at once. So I think that this is the key issue. When are the meatsacks able... which organizations will put 100% of meatsacks on this? And will they be able to not just be the meat bridge, the compiler between the output and the input of the AI, and actually orchestrate it? When could they be sophisticated enough to orchestrate this towards a business result? And I think Microsoft and their 60,000-person buyout, one in four employees that are being offered a buyout, is a roadmap. I think another organization like them, they see it. The writing's on the wall. Dave, you've been wanting... Oh, go ahead, Lon, and then Dave.
Oh, I was just going to say, on This Week in AI this week, Andy Burman of Run Layer addressed this exactly. That's what he was saying, is that it's just the companies have yet to attach the AI to the data and the systems that would actually cause it to become more valuable. And so we're just waiting for them to sort of make that switch.
And why are they not doing that? Exactly the reason that you said, that it's just like people being hesitant or not understanding or security concerns or the meat process...
So I think it's both the meatsack doesn't know what to do,
They're like, 'What do I do? I already summarized this article. How many more... I don't have any more articles to summarize.' Like, but that's not what this tech is for. That was like the demo four years ago.
And cyber has made everybody in these big corporations play on their heels. Go ahead, Dave.
I think we're going to get there. I mean, this is early innings. I liken this to, like, you know, teenagers in high school talking about sex. They want to talk about it like everybody's doing it, but not everybody's doing it. And eventually they do get there. So, like, as we kind of move up the stack, I think you're going to see AI productivity gains hit not just tech companies, but normal companies. We're still in the early stages, and, you know, a lot of people talk about AI, but most people are not really using, you know, the full potential of AI. Most people are still using it like, you know, Google prompts. A few people are starting to use it, you know, for agents, but we're pretty early on.
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All right, just to put this in context, Ben, if we round up to a hundred billion in yearly revenue, this puts Anthropic at a quarter of Alphabet's revenue, a third of Microsoft's annual revenue, and a quarter of Apple's annual revenue, in but three or four years of charging for their product. That's why I'm sort of saying, like, are we fully appreciating this number? Have we really taken a hundred billion dollars in revenue...
...and put it next to, you know, Alphabet's 400 or Microsoft's 350 or, you know, Apple's 400 and change? Like, this is truly, truly nuts.
And it's based upon one business model.
...token. So maybe arguably two different billing plans, consumption and subscription, but it's one thing. It's just like one little thing here: just buy this intelligence. What if they have other products? What if they started...
This is the point. The one number that I just couldn't get over was the 900% net revenue retention.
Well, unpack that and explain it, Ben, for somebody listening. What does it mean to have 900% retention?
Basically, they took the same customer cohort from a three-month period a year ago and looked at how much they were spending, that was their spending, and then looked at and basically said that same three months this year, same customers, three months, 900... nine times more.
Nine times. I went and I thought, tried to look through history, and, you know, I can't imagine another product, including smoking, because it kills you, you know, where you use nine times as much of the product. And that goes to say that this is the most useful product I think that's ever been created. Now, what this says about the long-term ability to extract profits when you compare it to Microsoft, right, and you're on desktops all over the world, you know, you have a pretty good clear sense of product that they're going to be still charging for that 30 years later. Now, I think that what's really hard to understand here is how sustainable this incredible growth is and their ability to extract profits because we know the prices keep falling the minute that, you know, the models get slightly out of date. Anthropic has got this really interesting problem of being like, how long are people willing to pay for the frontier as enterprises get better and better at consuming this product and the meatsacks get in control of OpenRouter and start sending them to lower-cost open-source models.
Yeah. Okay. Here's what we're going to do. We're going to look at the top subscription products of all time, or currently and all time. And then we're going to put OpenAI and we're going to put Anthropic into that table. And then we're going to see if you guys can guess who has more subscribers, who has less. Don't cheat on this simple test. Before we do that, Lon,
I just forgot. Gosh, we're starting this incredible discussion and I lost it. But...
Now I'm putting on my Plaud pin. Here we go.
Pause for the cause here. I got my Plaud pin on. I just very gently press the button. You can barely see it there on my lapel. And I'm off to the races. Now I'm recording everything. I'm taking notes. And I can say this would make a great blog post for my newsletter, jcal on startups, to talk about subscriptions and how to grow subscriptions, and maybe we should do a tactical, practical one. And I could just mute myself on the podcast, say that, put it in there and say, 'Hey, make sure this gets on my to-do list.' Boom. Plaud's going to make sure... and I see you have your Plaud as well. Is that for your ever-increasing list of to-do items that you haven't gotten back to me on yet, Lon?
That's exactly that. There would be no way for me to keep track of everything going on at the podcast and newsletter studio that we're running without the Plaud pin. I keep it on me all day. I'm always hitting it just for little reminders, little notes, whatever I'm going to need. And then I could check in at the end of the day and the beginning of the next day and get to all those checklist items that we did not get to the previous day. So, if you want to check out a Plaud pin for yourself, go to plaud.ai/twist and use the code twist and they're going to give you 10% off. plaud.ai/twist.
All right, now we're back. I'm going to play everybody's famous game, who has more subscribers. DA, the name of the game is who has more subscribers. More subscribers. Do you understand the name of the game?
Which game show host was that?
Wink, wink, wink. Calacanis, Dale, something like that.
Okay. In all seriousness, I don't know if everybody understands exactly how many subscribers these products have. Anthropic is undisclosed right now, unfortunately. So the game kind of doesn't work. Consumers, according to OpenAI and some reports, OpenAI has 50 million subscribers, 50 million subscribers in their consumer base out of their 900 million weekly users, about 6%. So the game is off. I was kind of goofing on it when I teased it. But let's talk about that as a concept because in all seriousness, the one I always go to is... and I'll just ask you to give me your best guess. Your best, best guess, DA Wallach, how many subscribers does Microsoft 365 have? Microsoft Office. This is obviously the most successful business subscription service. I'll give you a little clue there. Most subs. That's the most successful one of all time.
I'm going to guess 200 million.
Very close. 110 million subscribers. It's extraordinary. When you think about that, it has over 10 billion in estimated annual revenue for consumers, but paid subscribers, 110 million is the best I can estimate here. And if these things are at 50 and these are consumers, prosumers, this is an enormous subscription business. Do you think consumers will ultimately pay 20 bucks a month for this like they do for their Netflix? You know, I think...
And agents. I think both Apple and Google haven't reached their steady-state offering yet, clearly. And, you know, insofar as the mobile phone remains the preeminent computing platform, it's theirs to lose. So my assumption is that at some point in the future, Apple Intelligence is going to be at par with these things. I mean, it'd be a real screw-up for... I mean, it's already, they've already screwed up by not being there today, okay? But they're the biggest, you know, one of the biggest companies in the world. They're not hemorrhaging cash the way that all their competitors are right now on AI infrastructure. So they've got a big budget that they should be dedicating to ensuring that everyone who uses an iPhone is not paying a $20-a-month cloud subscription or OpenAI subscription.
Do you think that's a f-up or do you think that's a good bet? Because I think they intentionally decided to wait it out.
I think they're patient. I think they have the distribution. So they're in the pole position here, and, you know, I would be doing the same thing they're doing. I mean, I would assume that they're trying a lot of stuff inside the company, and once they get to a product that they feel is good enough, safe enough, user-friendly enough, that's just going to be what's preloaded, right? And...
If they f-up, then they buy Instacart.
I mean, I think they can wait. They've got the distribution, and, you know, we'll see if Sam Altman's mobile device, whatever that ends up being, is going to actually be the next platform. I don't think the Meta glasses are likely to displace cell phones. So as of yet, we have not found the successor to the iPhone, and the same can be said of Google. And, you know, obviously they're further ahead on AI than Apple is. So it's also theirs to lose when it comes to the people who are using Android phones.
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Here's your chart before you go, Dave. Apple services obviously really huge. Anthropic 65 billion run rate, I guess, if they're all subscription. We don't know if tokens is broken out there. OpenAI 50 billion. Netflix 49 billion, Salesforce 40 billion, Adobe 27 billion. People have talked a lot about that one being at risk, and obviously Spotify's done pretty well.
Can I just say one last thing, Dave, before I hand it over?
I have not given access to my email to anything yet.
That's my red line.
What's going on in your email? What's going on? Well, a lot of...
This is your stuff from like 20 years at your corporate.
I'm not saying what platform I'm using, but I have not given the keys...
...to any of these guys. And to me, that's the test. That's the test. Can you get, you know, can you get 100 million iPhone users to hand over all their data...
...to one of these new companies? Absolutely. And...
Apple is much more likely. Well, oh, there's something going on.
I think maybe...
I have an idea for you, DA. All you got to do is make a shadow email, make a new one, da new at, and then all your emails that come in from this point forward get sent there. And then your old account is human only, and the new account is...
It's a little complicated. It is complicated. It is.
We should shout out harmonic.ai. Thanks. We got another pause for the cause...
...for that note. For that amazing chart that you showed comparing all the subscription services. Pulled that directly from our friends at Harmonic AI. Thanks to them.
Okay. And everybody go get Harmonic AI, especially if you're in the VC business. Basically, imagine you had a database of every possible deal and a custom-made LLM put together with it. Incredible. For research,
If I'm handing the keys over, I would much rather that AI be predominantly local.
Yes, me too. So, you know, this edge stuff, I mean, again, for the top enterprises doing really complicated workflows and multi-agents, all that's probably all going to be cloud. I get that. But like, I still find the argument persuasive that for the average consumer, 99% of what they're going to want to use AI to do will be doable on the edge, on their iPhone, you know, within a few years. So why wouldn't that be where we ultimately go?
I think you were bringing up an interesting point about the consumer subscription. And I think you were looking at customers, not necessarily users. I was, you know, doing a little research in the background here. Sorry, I didn't follow your rules. So top three consumer AI platforms. Who do you think's one, two, three?
It's got to be OpenAI and Google are pretty similar. I'm going to say Google on top, OpenAI, and then ChatGPT.
Close. OpenAI is number one. Google Gemini is number two. Guess who's number three? You were not correct. CL...
Wait, hold on. It's not... it's Microsoft.
So is it... yes. Is it Google...
