← The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: Anthropic Raises $30BN at $380BN Valuation | Thrive Raises New $10BN Fund | OpenAI Buys OpenClaw | Stripe Raises at $140BN: Is Adyen Wildly Undervalued? | Monday, Figma, Shopify: Which are Buys vs Sells?
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- [00:00]
Rory O'Driscoll
You've never seen a company grow 10x in GAAP revenue and run rate year on year for three years. So you're leaning into the singularity here. Wall street has decided this is the bet they want to make. Capital has decided this is the bet they want to make. People are going to try and make this bet. Wall street fell in love with AI and to do that, had to fall out of love with SaaS, right? Everybody should get a little bit of a grip and not extrapolate to the end. But whatever, that's the movie right now.
- [00:25]
Jason Lemkin
Who wants to get back to early stage? I want to do the anthropic round. Give me a fucking break. I don't want to have to pick which accounting software in four years might break out for AI. No one wants to do that. Just show me the carry.
- [00:40]
Harry Stebbings
This is 20 VC with me, Harry Stebbings. It is my favorite show of the week. Rory o', Driscoll, Jason Lemkin analyzing the biggest news in tech that has gone down this week. Anthropic raises $30 billion and a $380 billion post. Openclaw creator Peter Steinberger. Jo Thrive closes on a mega $10 billion fund. One for early, nine for growth. We also have Stripe versus Adyen and then finally AppLovin down 70% and Shopify getting no love. What is going on in public markets? But before we dive into the show today, I run the 20 VC fund and I get this question from founders all the time. Oh, Harry, I can't find a good dot com. Do you have a good hookup? Well, let me tell you now, the answer is always going to be no. I don't have a guy or a gal for that. I do have a recommendation though. If you're building a tech startup, get a tech domain. Tech startup, tech domain. It could not be more obvious. As an investor, I appreciate founders who put thought into their branding. When I see tech in your name, it tells me right away that tech
- [01:50]
Rory O'Driscoll
is at the core of your build.
- [01:51]
Harry Stebbings
It'll say that to your customers too. A clean and sharp domain like tech pays off in the long run. You know nothing. Tech1X Tech, Aurora Tech. All of these great tech companies, they all use tech as their domain. These are my two cents. If you're building a tech startup, don't overthink it. Get a tech domain. While tech gives modern companies a home, online checkout helps that home convert by turning traffic into revenue. Digital commerce is exploding, but payments are still where revenue leaks. Checkout.com launched in 2012 to fix that. They don't try and be everything to everyone. No, they just do one thing better than anyone. Digital payments, digital cloud, native sub 500 millisecond latency and 99.999% uptime. Today that bet has paid off with a $12 billion valuation and 65 merchants each processing over a billion dollars annually. 65 doing over a billion annually is insane. Check out Power's $300 billion in e commerce for brands like Uber, Klarna, eBay, Vinted and more. Now they're building for Ajantic Commerce where AI agents buy on behalf of your customers in real time, partnering with Visa, MasterCard, Google, Microsoft and OpenAI. Now, if you want payments built for, what's next? Talk to the team@checkout.com while checkout powers the moment money changes hands, invisible powers the people behind the work. Why don't we hear more real AI success stories from big companies? The models are insanely good, but implementation's the problem. It's really, really hard. There's data all over the place. There's lag legacy tech and manual workarounds. It's a Ferrari engine in a shopping cart. Meet invisible. Invisible trains 80% of the top models and then adapts them to the messy reality of your business. Take the Charlotte Hornets NBA team. Invisible took years of game tape and analog scouting notes to go from uncertainty to a draft pick and summer league championship win in weeks, not seasons. Get the data in order first and suddenly AI can do almost anything for you in the Enterprise. If you AI that hits the P and L, go to InvisibleTech AI20VC.
- [04:10]
Rory O'Driscoll
You have now arrived at your destination.
- [04:13]
Harry Stebbings
Boys, it is so good to be back. Now we might as well rename this show for the first segment at least this week in Anthropic because my God, the news announcements that came out. I want to start with the fundraiser itself. Anthropic raises 30 billion at a $380 billion post money. Now, it was originally 10 billion and it upscaled to a $30 round. How did we think about this?
- [04:38]
Jason Lemkin
I think if you're not that you're not of interest to 98% of venture. I mean, I'm not even in the loop. I don't have an allocation to Anthropic or a pro rata. But people I saw on the periphery of this investment that I didn't even know would be on the periphery investment shocked me. So Rory can talk about. We can talk about whether it's cheap or not on a forward multiple basis. There's probably arguments Each way there's arguments it's cheaper than the last round, right? Just on a forward revenue basis. But not to be an echo or Captain Obvious. This is just, you know, it's the same day thrive or the same Week Thrive races 10 billion. This is what everybody wants to do. This is the only play in venture when you know, the public markets for software stocks are down 20 some odd percent this year. This is the play. There's almost no other play other than showing up to demo day.
- [05:20]
Rory O'Driscoll
I think actually Jason nailed it. The comment that this is the play, look, the last three, four or five rounds have worked. The two rounds in 25 have worked really quickly. You know, the 60 billion round at the start of the year, the 160 billion round at the end of the year. Remember we talked about it, we said oh, that's not actually crazy. And here you are getting a 2x again. You've now clearly reached the point where as Jason says, if you have a multi stage fund, you just got to put some money in and get your 0.01% ownership and add value because otherwise you're not showing up in the only thing that's working. And it really is one of the only thing that's working. I mean if you eyeball down the unicorn list, what's amazing is, and I'm just doing it reflecting on this, even two rounds ago it was the second or third largest unicorn and it's probably outperformed most of the unicorns that are one tenth its size in terms of share price appreciation in the last 12 months. This thing is a juggernaut with momentum in the short term momentum massively outperforms value. So everyone is wisely getting in on the momentum play.
- [06:18]
Harry Stebbings
The thing that I think too is just like the elasticity of capital supply. I'm doing rounds today where even at the early stage, a $30 million Series A round has $1.2 billion of demand. And I've never seen so much money chase seemingly such a small concentrated number of companies.
- [06:36]
Jason Lemkin
But they are hoping there'll be another. I mean here's the thing about anthropic I was thinking about, about this with the SAS crash is just, you know, gravity's almost gone up to Jupiter levels in tech, everything's being pulled down. Six billion is not enough for Atlassian, you've got to be six billion like Databricks growing 60%. Okay. Gravity is just pulling everything down and so you've got to invest in these handful of folks that can achieve escape velocity not just on Earth, but On, I mean, I'm no Elon Musk, but on Jupiter or something. Because the flip side is everything else is getting pulled down by gravity down a gravity well, right? They're unsellable. I mean, you look at app love and 70% growth isn't good enough. Look at Navon for the gravity well coming down to a $2 billion market cap, okay? That is a gravity well sucking everything down when the ship can't leave the planet. And so with anthrop think it's left the planet. I mean, Claude, code from 1 to 2.5 billion at the end of the year to today, that's escape velocity, you know, the early stage ones that, that's why it's a head scratcher for folks that have been around for a while, because the bet is that you'll escape this, this massive gravity well. But if you do, there's. There's 10 billion from Thrive last week and 30 billion from Andreessen. But man, the gravity is, is. It's a. Right.
- [07:46]
Rory O'Driscoll
Now, I, I get the analogy. It's like, I think it's almost like it's a black hole in the sense of these two or three companies are sucking everything else in and spitting them out. Now, over the medium term, is that massive over extrapolation? I think so. I think there's an element of projection going on here and, you know, a fair amount of discarding babies with bathwater. But short term, I mean, short term, we're narrative creatures, right? And you're right, Jason. The narrative right now is AI is going to eat everything within AI. The narrative is arguably less clearly, but nonetheless they have. The models are going to eat everything. And anthropic looks like for enterprise, it's clearly the best model. You take all that together and this is the thing that's going to eat everything. And once you have that, you can justify any price. Conversely, at the same time, you see everything else just trading down to points where you sit there when you go, Some of these SaaS companies are trading at 8 or 9 times cash flow. And are they really going to go away in that period of time when they're growing 10, 15, 20% at the moment? In the end, it will equilibriate because that's how price works. But you find yourself trying to articulate what's the forcing function that will kind of break this overinvestments, break the spell? And that's actually a hard question because we're talking a lot about the value of the company, but really you should also be talking about the performance of the company. And this stuff is working. And that's the aha, the revenue accelerator we've seen. I mean, the sound bite is going to be three years of 10x revenue growth, right? Technically ARR growth, but yeah, revenue growth as well. And that's not only unusual. I went back and plow through the early Microsoft, the early Google, the early Compaq. It's unprecedented. I even started trying to adjust for GDP growth, trying to adjust for inflation. The truth is you've never seen a company grow 10x in GAAP revenue and run rate year on year for three years at this scale. Just hasn't happened. So you're leaning into the singularity here. Now it's worth pointing out Microsoft, many of these other Companies that had 3x4x year on year growth for three or four years were also wildly profitable while they were doing that. Was this company still losing a ton of money? But from a growth rate perspective, this simply has never been seen before. And at the margin, we're all growth chasers.
- [09:52]
Harry Stebbings
What's interesting to me is that it seems like what other $380 billion company is there a CEO where they say but if we misspend on compute for a year, we're bankrupt. There seems to be this absence of fragility, not being priced in. When he openly says it's first of all, you're right.
- [10:08]
Rory O'Driscoll
And this is a reference to Dario's long andwarkesh podcast, where one of the very sensible, and I always find him frankly way more grounded than some of the other leaders in this space, where he basically said this is tricky because if you underinvest and you miss a cycle, the other guys pull ahead and then your growth dies. And we know what that's like. If you over invest because the money is so much. If you over invest and you hit the point where you don't get the returns to scale, then you are really long compute and then one could go bust. But I think part of the message was we are trying to be a little more circumscribed than the other major player OpenAI in terms of our future commitments to make sure that doesn't happen again, it is back to the same thing. These companies aren't like the explosive growth Internet companies or software companies like Microsoft because they are wildly capital intensive. They are much closer to semiconductor companies in terms of structure. Even Dario talked about the amount of capex he's looking at over the next three to four years. It's an astonishing amount of money. It's Tens and hundreds of billions of dollars. These are not software companies with free cash flow. And that's probably one of the big risks. At some point people go, hmm, it's just better to own companies where there's free cash flow than companies where there's not. And intuitively you know that you can get to free cash flow by slowing down. And that's actually true. Getting to free cash flow probably also assumes slowing down growth. And once you slow down growth, you wake up and rely as well. On a GAAP revenue basis, you did 4.5 billion last year, maybe 15 plus or minus this year on GAAP basis. You know, maybe 30, 40 times GAAP revenue is a little pricey, so it's going to be hard to manage that.
- [11:42]
Harry Stebbings
What percent of the 1 to 14 billion in revenue do you think is Customer acquisition from OpenAI? Customers versus net new customer acquisition?
- [11:51]
Rory O'Driscoll
Doubt. It's a huge amount. We're seeing some of the lots of enterprise having relationships with both, which totally makes sense. So maybe at the customer count, at the logo count level, probably not a lot, but at the individual token usage basis, I actually don't have insight to that. Someone like OpenRouter might have that and that's where it would show up. But I mean, to be fair, stepping back a million miles, most of OpenAI's revenues comes from ChatGPT on the consumer side. And Claude, less than 20% of the revenue is consumer. They really are slightly separate companies with an overlapping Venn diagram, same raw technology, one very much gone to enterprise encoding, the other mainly consumer, but with some enterprise encoding. So I don't think the narrative is at a direct level. Anthropic's winning, so OpenAI must be losing. I think the narrative is venture and soon Wall street just loves AI and doesn't love anything else.
- [12:41]
Jason Lemkin
Still, it is crazy. It's too early for Anthropic to be stealing enterprise deals for OpenAI because even those deals are one year and they've just been signed, right? Anthropic said its 100k customers are up 7x in the last year, so there's not enough time to steal deals. Having said that, going from 5% of OpenAI's revenue to 64% in 14 months, that is stealing budget, even though the budget is accelerating in ways we've never seen before. Global Software spend up 14% this year, which is unprecedented. It's still a fixed pie even if it's growing. So I don't think Anyone thought when ChatGPT broke out that Anthropic would have 64% of its revenue at this point. And that's a lot of momentum, right? That is Code Red. We thought Code Red was about Gemini. I guess it was, but maybe it's like Missile Command. They're coming from everywhere.
- [13:29]
Rory O'Driscoll
I think you're right, Jason. That's a great point. I mean, there's a reason when we were talking about CEO of the year, that was clearly dire. Because if you look at where the story was and a year and a half ago versus where it is now, I mean, Anthropic just ran in and scooped the money. Can't be great if you're the other guy.
- [13:47]
Harry Stebbings
Software spend is at 14%. Stairs, you said the highest. Higher than it's ever been. What do you think it is in 2030?
- [13:53]
Rory O'Driscoll
The reason I pause is, look, software has grown pretty steadily 2 to 3% above GDP growth for a couple of decades. And that's kind of the low rent, the kind of the low drama version of the Andreessen software will eat the world. It's kind of growing now, but it's still 3% plus or minus the GDP. So the probable answer is it gets back to the discussion we always have. It probably regresses to something like that, unless you really see that AI unlocks productivity and labor spend, in which case you probably could see 5 or 6%. My guess is the swing on whether it goes back to its GDP plus 200 basis points or stays at GDP in 400 or 500 is all about massive labor and efficiency and productivity. Savings have to come from the AI, and if they don't, growth will decline. You struggle to articulate a lot of bear cases for most of these AI companies, which is why we're all investing in them. Everything's working. Yeah, competition is tough, but the markets are huge. But there has to be some bear case. So probably one embedded one is, are you really getting the ROI from this 10, 20, $30 billion of spend that you're making in enterprises? If you are, then you'll probably do more. It'll go to 60 and it will be fine. The canary in the coal mine would be if a year or two enterprises are saying, that was great, but we're going to slow down on spend for a while because we need to get the roi. We didn't make the labor savings. That's probably the thing to watch. To the downside.
- [15:20]
Jason Lemkin
Here's what I think, though, and this has changed since we did this show. I think it's even changed in 90 days or 60 days, which is that more and more Enterprises are going to will this into existence. What I mean is you can make a decision. Do I want to invest? No matter what anybody says, for a large enterprise, AI does not miraculously replace 10,000 employees in an hour. It doesn't work that way. So you have to make a one, you have to make a bet, just like we've always made at enterprise software. But then you have to decide also, I just don't want a bigger company. I also want to do layoffs. I also want to be smaller, I want to be leaner. I want to do it. And so I'm going to lean into this bet. And not only am I going to do it, but my friend Rory over at Nabisco is going to do it and my friend Harry at Walmart. And I see this, it's not just all the Dario and waving his hands. I mean, he's great. And, and all these podcasters, I think enterprises are going to will us in existence. They want it to be true. And with AI, you can build almost anything you want. Now as we're doing this, you literally can build almost anything you want in software. I generally believe, even if it didn't have to be true, even if this was less, a little bit less revolutionary and people might back off in two or three years, they might be like, you know, I didn't see, this is classic enterprise. I didn't see this. The roi, I thought from that salesforce module or workday financials, I'm going to, I'm going to slow it down for a while. I think you can will these things into existence. I literally think you can make a decision. And I think by the end of this year that that train is going to be so far out of the station that, that these growth numbers will be jaw dropping because the Fortune 500 or Global 2000 will decide we are replacing humans with AI. Even if it's not the right decision, because it's not the wrong decision, it's doable.
- [16:50]
Rory O'Driscoll
I think actually, Jason, you're right. And I think that's the single big picture statement here. Corporate America has decided they're going to make this bet. The Zeitgeist is making this bet. It's unstoppable. Now. I mean, even what you're saying, Wall street has decided this is the bet they want to make. Capital has decided this is the bet they want to make. People are going to try and make this bet, which is very different than saying when they made the bet, they liked the result. But that's two or three years out. My Gut would be people will over bet over invest and you will have a retrenchment period two plus years from now. But I think right now you're just looking at two years where just as the hyperscalers said two years ago, we're going to do this and we're not going to blink. You're right. Corporate America is now going to say we're going to do this and we're not going to blink. Which means you're looking at one to two years of mega AI budget, not regardless of roi, but on the presumption of innocence, which is the presumption of success maybe is your word, Jason. I like that that's what they're going to do. They're just going to say it's going to work. This is the thing you got to do. CEOs generally have only two or three agenda items at any one time. There was a whole period in the 90s, Jason, when it was all about right, sizing and efficiency. Then it became on getting on the Internet, then getting on the cloud. And you're right, the number one thing now is make your big AI play. So everyone's going to make it, Evan's going to spend, there's going to be a couple more years of great spending and then we'll see. That's the movie. Which means that the next two years would be a good time to access the capital markets.
- [18:16]
Jason Lemkin
It's also why I hate to say I'm just not. I want to be really bullish and say that a lot of these public software stocks are oversold. And maybe it's true, but I mean, Harry just had Sebastian from Klarna on, right? And he likes to be a rabble rouser but he's like, I went from 6,000 to 3,000 employees. We know that. But then he said on two years I want to be at 2,000. Now he's trying to be a rabble rouser and he was trying to say, you know, I fired Zendesk two years ago and AI was magically perfect. But I think that's how everybody's thinking that I talk to. And that is great for Anthropic because we're going to replace those humans with anthropic spend and it is terrible for not every software company. Maybe Shopify is oversold, maybe Navon is oversold. But overall, even for my Cannon Brooks, it's not great for Atlassian. If we're all going to shrink our teams from 6,000 to 2,000, it certainly is. And maybe HubSpot and Monday. And no, we're like, why the hell are these horizontal apps oversold? It doesn't seem fair because the numbers are great. But if this is the mode we're in and nobody wants people, it's hard for me to feel there's a bottom and it's not valuations. Right. It's hard for me to feel that there, that enterprises are saying, you know what? I want to buy more seats next year. Guys, I've changed my mind. I'm tripling my seat count at HubSpot next year. I've changed my mind, guys, we're going all in. We're going to hire 20,000 more people next year. Humans who complain and whine and quit every three months and we're going to get them all seats of software. I just, nobody I talk to has that feeling today. Nobody wants to do that.
- [19:44]
Rory O'Driscoll
I broadly agree, but on the kind of sentiment, and I disagree on the statement that there is a bottom, I mean in the end price clears all markets. And what happened on the public SaaS stocks is you've gone from, as I said, the presumption of success, which is what AI now enjoys, to the presumption of failure. But that doesn't mean you fail. It simply means that you just look cold eyed at it and you say, what's the growth rate? What's the free cash flow? How do you value that? There's going to be a price at which these things stop declining and compound at a normal 1512-15% return a year. Markets work. The other side will overshoot. This will be doable, but it's just not a number you like.
- [20:23]
Jason Lemkin
But here's the thing, and of course you're right, if you have stable or growing free cash flow, there's a number, right? But here's what makes me pessimistic. And I don't want to be pessimistic. I want to be the guy saying we're never going to remove our systems of record. I want to be that guy. But as a cohort, public software stocks are approaching have fallen to almost 10% growth annualized. Okay, now if I just reduces that another 30%, we're in essentially the dead zone, right? We're in that area in the deep dark water where nothing grows because even the, the dead bodies don't fall. That you can't like 5%, 4%. It's even worse. It's all just price increases and suing customers. There's nothing. If AI was bringing us from 30% to 20%, you could make a whole Bunch of arguments you could say, listen, we're, we're, we're got a little sas, got a little older, we've slowed down our senior marathon, but things are still good at 20% growth, at 6% growth, I don't see any future other than the next five years of free cash flow. I think it's a valid worry if because things were bad before I like, let's be honest, things had already fallen into the mid to low teens before the IRA. It's not like SaaS was healthy. Public SaaS companies, these were not thriving. Dropbox growing minus 1% a year is not crushing it, is it? That's why I think the market isn't overblown because we were already at risk going into 2026. We were already weak and anemic. The overall blended growth rates and Rory made the point with Mike last week. Part of it is because we haven't put new names in. When we drop data bricks and anthropic and it's all going to. And if we, if we allow them to remain of a pure basket, it's going to look great. But the existing group is not looking healthy.
- [21:59]
Harry Stebbings
If we, if we look at like a duo, a Monday and a van, these businesses that all doing okay to decent actually but the price is through the floor and we keep on saying oh my God, it can't go lower. And it does genuinely what happens, I
- [22:14]
Rory O'Driscoll
think the markets, it's like the old cliche. In the short term it's a voting machine, in the long term it's a weighing machine. We're going to the voting stage now. My big aha is and Jason mentioned earlier I was thinking a lot about the SaaS apocalypse and did AI kill Sass? And I think what really happened is Wall street fell in love with AI and it fell promptly and you know, and to do that had to fall out of love with SaaS. Right. The burden of proof is the other way. Right. But you got to shake up between them. If you take something like Shopify, I'm going to say it. I don't think there is a credible near end story that replaces a website for shopping and a payments mechanism which is 60, 70% of their business with some kind of AI armwave. And in a way that there is for many of the workflow automation software companies. I'm just picking on Shopify, for example, in a positive fashion.
- [23:05]
Jason Lemkin
I'm super positive on Shopify.
- [23:06]
Rory O'Driscoll
Exactly.
- [23:07]
Jason Lemkin
So super positive. Right. But it is in the basket. It is cousins of the rest. Right. It is probably over, we could argue it's oversold. And if we were running ahead a long short hedge fund, Maybe we put 5% of the fund into Shopify. It would make sense. There is, even though here, just to be clear, I do think Shopify is oversold. It's easy for us to say on a podcast, right? I do think though there is a bear case for Shopify. What's the commonality between ServiceNow, Salesforce and Shopify? It seems like nothing, but actually they all could be abstracted away into a database. Even Shopify can. If I am shopping on ChatGPT, I may not go to that merchant store ever. And in the short term it doesn't hurt Shopify because it is the plumbing of the store, right? And it takes a piece of the gmv. But ultimately, if the future of e commerce is conversational commerce and it does not happen on the Shopify platform, that is not a net positive. And Toby says the same thing like that's why he's done more code commits in the last 60 days than the rest of the history is because the Shopify software, even if it's only 25% of the revenue today, that software in two years may be obsolete. If Toby thinks it, and this is the most resilient AI and Toby thinks it, what? What hope is there for mere mortals
- [24:14]
Harry Stebbings
that assumes the UI of the future is conversational commerce.
- [24:18]
Jason Lemkin
It is the UI of today, Harry. If you're deep in e commerce and
- [24:21]
Harry Stebbings
talk to anyone, it's the UI of today today because it's what the most productive people in the world find. The most optimal ui, which is Sam Elon Dario. Actually when you look at consumer most often they actually like browser based UIs. They like discovery, they like an option set.
- [24:36]
Rory O'Driscoll
I agree. I think that again I definitely think chat is wonderful for research which is why despite your opposition in the past, I've loved the JIO marketplace. I think chat is the place you go for considered purchase and look doing research on, you know, whatever you're buying, right? But then you go to the store, you look at the thing. I don't, we're a long way from. I'll just press the magic button on ChatGPT and have it come.
- [25:01]
Jason Lemkin
So I do, but it might not be on Shopify's website, it might be on an agentic flight. It doesn't have to be ChatGPT. It could be Harry and Rory's shopping site. That is better than the built in conversational commerce and Shopify. Everything's at risk. Every platform that is open is at risk that an agent is better than the native platform and every platform that is closed is at risk of being at least slightly bypassed. And that's the risk is that I haven't logged into Salesforce in six months. But we use it every. Every minute. Our agents use it every minute. I think it would be disingenuous to say that couldn't happen to Shopify, that agentic commerce agents forget about part of discovery is going to happen on my sofa. Don't get me wrong. But all the stuff that really matters may bypass the user interface of Shopify. I just think it's a threat. I'm not whether the size of a threat is as large as it is to others, probably not, but it's. It's not to be dismissed. Given the incredible pace of progress we're making. It's like I can't. I'm struggling to keep up.
- [26:02]
Rory O'Driscoll
What I don't like about this discussion and what makes it hard is. And actually one of the most insightful things I saw about in the last couple of weeks about this SAS discussion is it's really hard to disprove a negative. I think your stock might go down. How do I disprove that? I think you might be displaced by AI. My big aha is I'm going to repeat it again. In the short term, we're narrative and momentum creatures and all that's happened now is the narrative and momentum has shifted to AI is going to do everything. So the people who are left trying to prove that that's not the case, you can always articulate a scenario. The question is, on a balance of probability basis, is that going to happen? And the thing is, smart traders don't fight the tape. Basically, in the short term, the momentum is all around. This narrative of AI replaces everything. That's the way the momentum trade is going. At some point, I don't believe it will. I think it'll be amazing. Just like software was amazing. Let me repeat. Software was the best industry of the last 20, 30 years. At the end of 2030 years, it accounts for 4% of the US GDP. We'll still want to eat, we'll still want to drink, we'll still want to drive cars. Everybody should get a little bit of a grip and not extrapolate to the end. But whatever, that's the movie right now. While that is happening, you would be a buffoon to get in the way of a momentum trade. At some time, the momentum trade will dissipate and people will go, ooh, this is really amazing. But it's just not quite the universal everything. And that's the point at which you'll see a correction. But until then, narrative dominates valuation in the short term. And I pity the poor public SaaS CEO who, as I say, trying to, you know, prove a negative.
- [27:34]
Harry Stebbings
I.
- [27:34]
Rory O'Driscoll
Let me prove to you why I'm fine. It's just too hard.
- [27:37]
Jason Lemkin
Just one thing, the tough thing as an investor, and maybe you do also have this lab. It's called your portfolio.
- [27:43]
Rory O'Driscoll
Yes.
- [27:43]
Jason Lemkin
And your portfolio. One thing you can say today is, hey, my early stage companies aren't truly at scale. Scale is north of 500 million or a billion in revenue, so they don't matter. But on the other hand, you may be seeing the future in your portfolio. Public aside, when I look at my last fund, right, you know, and I see what's happening and the fund's in good shape, whatever. 4.5x. But honestly, like, two companies are, like, massively benefiting from the current world and B2B massively benefiting, accelerating. One, I would say is a push, like it's benefiting in nine figures of revenue, but also being hurt. And everything else is struggling because of AI. All the rest of that last fund, and you can, you know, it's not all growing zero. I'm not saying that, but, man, and it was so similar in 2023. So is that the past or the future? I get confused. But. But if you have a portfolio of companies exposed to all these things, they can't hide in high grr. Like ServiceNow, they can't hide in price increases like Salesforce. They're getting whiplash at a pace much faster than the public's. And so when you see this on the 1st of every month, when you get updates, it's hard to be optimistic in 2026 about anything not already getting a boost from AI, because you see the dramatic effects, and it's just hard to keep grinning and smiling and saying, go, guys. When you don't see any AI boost in your February or March investor updates, it's hard to remain optimistic.
- [29:07]
Rory O'Driscoll
I think that, on the other hand, is probably true. One common definition Evans does the SaaS is dead. And it's such a useless word because we have to define our terms just a little bit more carefully. If you think software as a service means selling software on a monthly basis for a fixed or variable price, then the thing is, Claude is SaaS, Harvey is SaaS, and Salesforce is SaaS. So when people say SaaS is dead, are they saying there's kind of two separate threads here within the new world of AI, are we talking about how much the model will get versus the next? I call them new school SaaS like the Harveys of this world, the next generation companies that pejoratively are called wrappers and optimistically are called standalone companies that can leverage on top of ChatGPT. Then separate from that there's old school SaaS. So I think what people are Most of the time people are saying old school SaaS. In other words, stuff that was built pre 2022Pre GPT is what we're really talking about here most of the time. Then sometimes people go all the way to the all software is dead and the model's going to eat everything. First of all, you have to just distinguish between those two scenarios. What you're talking about, Jason and I agree, is, for lack of a better word, old school SaaS built pre2022. What you're saying, which I think is also true, is that if you're public already in one of those companies, Salesforce Service now on, you're now living in a lower growth world where you got to make the model work financially while at the same time investing in the future. Because if you just make the model work financially, as Mike Cannon said last week, the good news is you have five years of 30% free cash flow and the bad news is in year six your revenue goes to zero. So you got to be financially disciplined while adding AI to grow it. That's again kind of going to distinguish public versus private. That's the public SaaS company movie. Then the tough category is the small private pre2022. If you're not getting SaaS lift, you really got to worry about what you're doing, especially if there is a credible SaaS story in your space. I do believe again there's a lot of markets, even pre 22 that are software plus payments software plus that aren't all AI. It's not a baby bathwater thing. But the sweet spot of your argument is horizontal workflow related software built pre2022 that's not public with critical mass. That's probably the hardest place to be.
- [31:27]
Harry Stebbings
I just see a realization in my portfolio now of companies that are in the 8 to 20 million ARR range, not benefiting massively but growing 80 to 100% that are basically like okay, we have raised our last venture dollars and we're going to have a good business, but we are moving off the venture train because we can't align to what is needed today to make that Next round work. And that realization I'm seeing set in.
- [31:50]
Rory O'Driscoll
Yeah, that's very fair.
- [31:51]
Harry Stebbings
Is figma a baby getting thrown out with the bathwater?
- [31:55]
Rory O'Driscoll
No, because. So there's two questions. Is it and should it? Right, the is it question. It's still valued at 12 billion plus or minus. Right. It's still an amazing outcome. It's still I think roughly 10 times plus or minus revenues. And I remember I used to know the growth rate and now I don't. It's 30, 40. I don't swear to this in that kind of. It's not 10xing. It's 30 or 40. It's not down to let's call it miserable single digit SaaS. It's a perfectly great public company. 30, 40% maybe higher growth rate story. So at 10 times revenues plus or minus, it's absolutely not getting thrown out with the bathroom. It's probably just getting valued correctly in the absence of narrative lift. Right. Whereas two years ago it would have been valued at its value plus narrative lift. It's gone from the voting to the weighing part of the capital markets. It's now so from that's from a value perspective and then the other part of it is what's driving that is the where does it go Comet and I'll refer to Jason on that.
- [32:51]
Jason Lemkin
Here's the bull case on Fig. But you can't argue like here's the existential problem with public. You can't argue with the current numbers. Right. You can't argue with the current growth north of a billion. It's great. The other thing you can say is let's go back to your favorite rep on level number one use case for both product teams building prototypes. Okay, this Anton said this last week number one use case at scale not when Harry invests number one use case today for both. Okay. That is all revenue figma should have figma make is a failure. And I don't mean to be dramatic but I think folks at Figma if they're honest would agree like it's. They thought this was revolutionary but that is 500, 400, 300, 400 million of AR. Figma should own. They should own this. That lovable and repl. It should not be owning product prototyping and development for product people. Figma should own this. They don't. They missed a whole generation here and that's the that ties into all of this. Figma can't argue with figma day that checks every single box on on growth market share everything but good God, they missed 403,300 million of growth in their core for AI I'd be pretty critical. Right? It's actually.
- [33:58]
Harry Stebbings
It's actually double that Both rapid and lovable at 350 independent.
- [34:02]
Jason Lemkin
Yeah but not all of it is pro. It's just the number one use case for their enterprise I'm just guessing it's for both. It's their number one use case for their larger customers. That's the majority of the revenue today versus the minority but it's not all of it. Right? So assuming that that morphs to 300 million of bookings but figma should have gotten all of it. If figma make was better why do I want to buy another tool to do this? Especially because these tools weren't even really good until the fall. As you guys remember when we started this these tools weren't that great in the beginning. Ok? Figma should have owned this. This is just the bear case. Right? And my God now we're in 2026. Why is. And the earnings will come out I think before this pod comes out. But why is it make a $300 million, 400, 500 million dollar error business like this is much easier to sell than these damn seat licenses where we have to bang our heads against the wall the desk to get 20 bucks or 50 bucks for figma I can just sell multi million dollar deals of level and replit just because my product guys can now ship functional prototype like they miss this huge change base 44
- [34:59]
Harry Stebbings
have also absolutely crushed within Wix and they have.
- [35:02]
Jason Lemkin
I don't know that they sell the product teams like this for figma though. I here's just my criticism of figma and again it's easy for me to say good God, I didn't build the goodest company as figma. Okay. But the honest criticism behind closed doors is replied and lovable shouldn't have gotten here guys. We own this space. We let it go and we're just seeing and this. This may happen to everybody. Guys, everyone. That's too slow. If Figma was too slow what hope is some of these other public companies?
- [35:26]
Rory O'Driscoll
And I think you're exactly right.
- [35:28]
Jason Lemkin
Well, it's brutal.
- [35:30]
Rory O'Driscoll
First of all I think you are correct. Let's do Figma first and then the other companies. Yeah And I think back to the valuation. I think the valuation is perched between if you'd done this and you had another 3,400 million of revenue growth rate would be north of 120% you would probably be valued at 20 times revenues, 25 times revenues. If you don't get on top of this soon, that 10x revenues is going to go down to 5 and 4 and where the other 7% growth are. So markets are doing their job. There's an embedded probability that they make better product and take more share here and then some probably don't.
- [36:04]
Jason Lemkin
Right.
- [36:04]
Rory O'Driscoll
And it's kind of in the middle. And you're right. Fast forward five years, there's really only one or two stories. They get on top of this, they get a third market share, valuation continues to grow, they're fine. If they don't get on top of it, you trend down to the horrible multiples. The comment I would make though is. And again, this is back to the not everything will roll over in one day. I do believe, ironically, even though Figma I think is one of their most exciting companies of the last five, 10 years, I think that space was very vulnerable to disruption because it turned out to be very AI adjacent. And I do think, and I'm not trying to sound boring, I do think there's a continuum across all these companies of how adjacent you are to what the models could do. And there are companies that are very close to it and are going to get, as you say, sucked into the gravitational field and there are companies that are fairly far away from it. I believe there will be change in accounting. I believe the next generation of accounting software companies, we've looked at them, they're super interesting, they're adding AI, but fundamentally 80% of the value in an accounting software package is independent of AI. It's debits and credits and a good ui.
- [37:07]
Harry Stebbings
How adjacent is canva to AI?
- [37:09]
Rory O'Driscoll
Probably pretty close too. Individual creativity, individual coding and individual creativity strike me as extraordinarily close to AI because it's happening right now. Conversely, I mean, I'll say it, even Salesforce, we talk a lot about Salesforce. And Jason, I hear you on your agents, but the truth is the level of disruption in go to market software hasn't been as acute as it's been in some of these creative areas. Our coding, our customer support. Now, I'm not saying it won't. I love what you're doing with your agents, but just being objective about where is the eating happening fast? Where is it maybe happening slow? Maybe where has it not happened at all?
- [37:45]
Jason Lemkin
Yeah, but, but, and you're, of course you're right. But I just. Listen, I'm an investor in a company called Monaco that, that Harry knows. It's, it's, it's, it's the next AI SDR for us. We Already have four. Okay. And they launched last week. And we, we went live last week at the same time. A couple things that are interesting. First of all, from a technology standpoint, it booked us a six figure deal the first day. None of our other agents could do that. It booked it on its own. A six figure deal. That. That is interesting because that is the pace of progress. Our other products, we had Asian Force, Artisan Qualified and a few others. They're all great. We use them every day. They couldn't book a deal on its own the first day. So the rate of progress is accelerating. Like we couldn't believe it did it on its first day. Okay. And then here's the second point. And then they have every demo booked up through the summer. If they had enough manpower, they could do 2 to 3 million their first month because the demand is so strong. The demand now there's fragility, there's turnover. We could talk about how prompts are portable and the fact that this is so good that we would throw out an agent we bought a couple months ago shows you how fragile everything is. But my point is that the demand is so strong, as soon as the products catch up to the demand, everything, that maybe these sales tools are not safe. Like so much demand in one week. Just. Just a torrent of demand. And I see it in all, all of these products that it is, it is inexorable. And it just gets my. It just got like, this one is better than the one from two months ago, which is better than the other one. It booked a six figure deal on its own the first day. Jesus. Holy. People don't like in the pod when I say jfc, but holy cow, when
- [39:23]
Rory O'Driscoll
you say booked, what do you mean?
- [39:25]
Jason Lemkin
It reached out to a leading hyperscaler. We've talked at this. That that wants to do a six figure sponsorship at Saster on its own. No human required. It decided who the targets were, it loaded them up, it went out to the person and it booked the meeting.
- [39:41]
Rory O'Driscoll
The meeting or the money?
- [39:42]
Jason Lemkin
Well, it didn't close it. That's the end of the year. But. But don't. But don't be. No. None of these agents could do this before February. They couldn't. They could do a lot of it. They could send emails, they could do a Market or HubSpot 2.0. They could customize it, but they couldn't literally go out to a VP at a very busy tech company and get the meeting entirely booked and loaded and ready to go like it is. And that's just progress in 60 days. What will it be like at the end of the year? It could close it on. It could completely close it.
- [40:15]
Rory O'Driscoll
Yes, it sent. It's a well written email and was able to schedule a meeting.
- [40:20]
Jason Lemkin
Yeah, you can, you can crap on it if you want. But my point is the products weren't this good.
- [40:26]
Rory O'Driscoll
I agree.
- [40:27]
Jason Lemkin
60 days ago you can say, oh, I have this company in my portfolio. It could do. It will show me the money like we've sent. We've done all that. We have 20 agents. I'm going to tell you, this wasn't possible on its own. You could get close. You could have folks qualify themselves in and go to Rory's website and say I want him. And the AI would like move it down the funnel. But to do it raw, people talk about it. This is why I really wonder if anything is safe from disruption. And I actually don't think any of the agent vendors are safe from disruption. Everyone's promiscuous with agents. We will switch. This is so much better than what we had two weeks ago. We'll switch to the next one if I.
- [41:03]
Rory O'Driscoll
First of all, they're too good, as is often the case. I hear you on the narrative, just pushing on the conclusions because I totally get the AI SDR use case. We're in, Reggie. We've absolutely seen things get better and better. What's been super interesting is the product a year, year and a half ago had a medium level roi, low level roi. It's taken iteration after iteration and now you're starting to see with the reasoning models, increased performance, as you say, started to be able to convert old leads to active leads. You're starting to be able to predict who you should reach out to. Definitely a lot going on here at the top end of sales deck. But my point is just compare it for example, with, as you say, to take one of your other two examples, coding. There's a two and a half billion dollar market already taking place. Not all the markets are moving at the same speed. If you take again to your example of figma, right? The maker, the next generation product tools like Lovable and replit, they're doing 3,400 million in space. My point is merely the pace of adoption is not consistent across the board. There's a sequencing question here at a
- [42:06]
Jason Lemkin
meta level, in some ways I don't think it matters because there'll be spaces that are destroyed, right? And there'll be spaces that are maimed. And I don't know that it matters on a terminal basis. Like if your Space is going to be killed in eight years versus eight months. If you've gone on to hospice care, does it really matter how long you stay in hospice? I mean to the kid, to the employees, it does to the family. But everybody pretty much knows when that SAS company goes into hospice, it ain't coming out.
- [42:31]
Rory O'Driscoll
You will play the game and find out. I don't know if everything gets rolled over in two years. Give an example.
- [42:38]
Jason Lemkin
Not everything. Not everything. The closer you are to code and support, the faster the disruption's been. No argument. Let me just rest on one thing. Just this is why I feel anxious about everything. But I don't have to run this Figma IPOS in July of 2025, like right when we got this podcast going, right? Friggin rocket ship actually at the margin, seemed to be benefiting from AI. At the margin, right. Just since July. Replit and lovable take 300,400 million of their market since July and maybe even since September or October because the product didn't even really work until September. October, October. Good God. This is the best. I mean we were saying Figma was the best of the best that there had ever been in July and now AI is stolen. And yes, product is one derivation away from coding. Like no argument, but let's not view any islands of stability when in July this was the best thing we'd ever seen.
- [43:30]
Rory O'Driscoll
Yes, it's only February. We went around the room in July when the Stock was at 110 and asked where do you think it'll be in six months? My vote I think was 35, so it's 20 something. But I was pretty right at the point in time, so I get it. But on the other, pushing back the SaaS again, the question is the velocity that happens. I was just thinking about kind of the SaaS change and we both started investing and look at this stuff early 2000s, right? Salesforce went public in 2004 and Service Titan, which is also a SaaS company, went public in 2024. So it took around 20 years for the whole thing to transition. I don't think it'll be that slow here, but I also don't think it'll be two years. And I think that matters a lot in terms of as an investor where you choose to place your bets. What we find ourselves thinking about is which markets are going to adapt quickly and which markets are going to take more time. For example, two of the most interesting apps categories other than coding and customer support we've talked about. But if you look at it two of the most interesting apps categories have been the entire law field and the entire healthcare doctor information field. It's no accident that both of those didn't really have a compelling old school alternative. It was much more greenfield than some of these places where you are competing against existing SaaS companies. Just worth pointing out that the sweet spots of adoption, it's this kind of jagged edge idea. It's not all happening uniformly. Some places it's happening now. And those have been amazing categories for categories that frankly weren't great in SAS land. I mean legal was a miserable category in SAS land. It's been amazing in AI land because LLMs manipulate language and lawyers manipulate language too. And however you want to interpret, manipulate. Right. Whereas some of the other more structured apps, it's been a lot slower. That's my.
- [45:15]
Jason Lemkin
Well, you know what? Maybe it's an interesting investing question, right? Because we started this anthropic. You could have two strategies to investing in AI and software. One is let's invest in massive disruption today. That's anthropic. That's most of capital. Another strategy, and maybe Harry would crap on it is listen, actually I want to invest in AI. I want to invest in the categories that are changing the slowest but with the best founders. But, but with the best founders. That way there's, there's a little bit of extra time. Some folks may be missing it. It's not that it's not coming. It's going to be as disruptive as, as anthropic and the rest. It's just I've got two, three, four years instead of two weeks.
- [45:51]
Harry Stebbings
It doesn't work unless you can do lifecycle funding as well is with the opportunity cost of cash you have the concentration going to a certain direction. If you take the second route of the contrarian approach, you have to lifecycle fund that until it becomes a contrarian.
- [46:04]
Jason Lemkin
Just slower. Yeah. It has to be more efficient for sure. Right. You can't raise four rounds a year in that approach. Right? Not for a while.
- [46:11]
Rory O'Driscoll
Look, which is why I think that the best place to be is neither of those two alternatives. Actually, the best place to be is about a year before the posse in terms of saying what's going to happen next. And that's obvious when you say it. One of my quotes I often give is the Henry Luce quote of Time. I think I've said it before here. He said my job as the publisher of Time magazine is to be six months ahead of the American public. Not two years, not a week. And it's the same thing here. I mean, fair credit to the smart folks who looked at Entropic in May of 23 at Spark Capital and Menlo and said, hey, this is the trend that's going to be and then you get the momentum. You don't want to be looking at something that's not going to happen for five years. Because I'm with Harry, the trick is to have. That's why I'm saying trying to construct some kind of thought process on sequencing which of the markets are most vulnerable, which of them will happen next, which of them will take more time in my view is going to be a key part of the app side of picking where to play.
- [47:06]
Harry Stebbings
I think. Jason, you also said about customers willing into existence. What I see in law, and I don't know if you do, Rory too, but is just big law firms willing AI into existence in a way that they never did in a SaaS era where you're just and cons and your atriums were coming with with products they were not willed in with the same persistence that these customer bases are today.
- [47:26]
Rory O'Driscoll
I agree, you're exactly right. I remember because we, you know, have invested in AI companies for 20 years. I remember for a long time there was deals where you go, you don't emphasize the AI because the customer would get scared, they wouldn't like it. It would slow down the sales cycle. Pre2022 and what's happened, and Jason said it earlier, it's the big aha. Here is post 22, if you don't have an AI strategy as a corporate leader, you're a buffoon. And no one wants to be a buffoon. So whoever's going to have an AI strategy, therefore they're going to spend money. I mean Harry, if you were running an AMLO 500 or whatever it is, right, you're not going to sit there and say I'm not going to make a play because I don't think it's all going to work. You're going to make damn sure that you do something. And therefore 500 companies, all of them went to spend I need to spend a million bucks right now.
- [48:09]
Harry Stebbings
They are competing on price just like us as venture investors. If they are not using AI, they are not able to charge a lower price and win that deal. And it is that existential threat that they will lose consistently if they don't.
- [48:21]
Rory O'Driscoll
I mean it gets back to where we started is there's nothing better than being on board a market where all the participants have decided they want to buy something, right? Now, I mean, that's why Entropic is working. That's why some of these other markets are working. It's picking the markets that just tips and it generally lasts only two or three years. And everyone's made that decision. That's what's happening here right now in some of these markets.
- [48:43]
Harry Stebbings
Rory, you said about 20 minutes ago about a narrative chasm or a narrative shift with regards to one of the companies we were talking about. When I think about narrative chasm and news cycles today, the most striking is stripe being worth $140 billion and Adyen being worth a third of that. Can we just try and understand, is Stripe wildly overvalued? Is Adyen wildly undervalued?
- [49:09]
Rory O'Driscoll
Actually, no. I went into this thinking, oh, I want to find some narrative story. But in fact, there's perfectly rational reasons with one caveat, why they are where they are. I mean, for start zooming out, Stripe just raising privately, I think 130 or something like billion. Adyen's publicly traded. Looked at it this morning, only my brain is gone 50ish. Less than that. Now, a couple of things. One is Stripe's doing five billion plus or minus. Adyen's doing two billion. So it's half the size. So two and a half times the size. So instantly you have to multiply by two and a half. Adyen is very, very profitable. But the growth slowed Stripe. It's not clear it's profitable, not clear as much, and it's not clear where the growth rate is. So they're a lot closer together than one would think would allow for size. Then on top of that, you have the. It's the classic. I mean, it's a little like the whole SaaS AI story. Do you want mid level growth and massive profitability or do you want more growth even at the expense of profitability? And right now people are opting for the latter. I mean, basically, instead of saying the strike price is wrong, the Adyen price is right, or something, just saying is that it's the eternal venture question. How much extra in revenue multiple do you play for how many extra points of growth if Adyen's growing? 20. And I'm sorry, I knew these numbers, but we're starting early in the morning. I looked at them last night and the detail is gone. But I'd gone through the. If adyen's growing at 15, 20% and you pay 10 times how much extra revenue multiple do you pay for something growing at 25%, 30%? Those are the contrasting narratives here. I mean, look Addy is a widely profitable company. It's like almost 50% operating margins, growth slowed, but yeah, this is a company
- [50:48]
Harry Stebbings
also that just wildly miscommunicates or communicates very little about how much cash they have, about how they're going to use it. Alternatively, Stripe communicates in an incredibly strategic way. We're telling a brilliant narrative, Ironically, given the fact that it's private, I do think there is this narrative chasm and I do think you can actually blame the communication of leadership at Adyen directly for a valuation mismatch aligned to that.
- [51:12]
Jason Lemkin
Do they even have a podcast at Adyen Management?
- [51:14]
Harry Stebbings
They should give up then. They should give up the 40, 50 billion. If they don't.
- [51:18]
Jason Lemkin
What do the Dutch drink? Not a cheeky pint. They need something to drink. They're the Dutch. I don't know what it is.
- [51:24]
Harry Stebbings
So Adyen 21% H2. 20, 25. Year on year revenue growth. Would you rather buy stripe at 130 or adyen at 40 or 50?
- [51:33]
Rory O'Driscoll
I would go with Adyen because the likelihood of it being mispriced to the upside is lower. Right. In the sense of old Roy.
- [51:42]
Jason Lemkin
Yeah.
- [51:42]
Rory O'Driscoll
You're trading on value. I mean, look, you have access to the data. You know it's widely profitable, you can value it. And the other case, you don't have access to the data. It's a private market. It's a wonderful company. I admire that company enormously. This is not meant. Again, you have to distinguish disclaimer people
- [51:57]
Harry Stebbings
for the collisons that are listening to this episode. Rory is not in any way being detrimental to Stripe. None of his comments are seen as a criticism and he is intensely sorry for even talking in any negative light about your company. Please continue.
- [52:10]
Jason Lemkin
Thank you, Harry.
- [52:11]
Rory O'Driscoll
You did that so well. But that's the role of price is to equilibriate between the other issues.
- [52:17]
Jason Lemkin
I'll tell you the simple reason I would take Stripe and it kind of echoes in my brain from. From Michael Cannon Brooks last week. Right. Is just the. The flexibility and agility today you have from being private in today's world. It's so stressful being public. There's so much going on. You heard Mike's point. I got to be more profitable and massively invest in AI. I mean, he was great, right? It was such a great one. Right? And he was up for the challenge, like to his kudos, right? He's up for that challenge. But to not have to make that trade off perfectly and be private. Even his sort of cheeky comment of his buddy Cliff didn't have to deal. Maybe he'll wait to IPO like that. I mean, I'd rather be Stripe, so I'm going to bet on Stripe on this one just because I think you have more flexibility today to respond to change.
- [53:00]
Rory O'Driscoll
As yet, my prediction is back. End of this year we'll see the big three guys diving for the public line, Entropic, OpenAI and SpaceX. And I don't think it matters. When you're profit or like Stripe, you really can stay private forever. But companies that need big capex for the foreseeable future are going to go public because they've sucked up all the private capital and now they need to go.
- [53:20]
Harry Stebbings
Isn't it a funny time where the public markets are both at the same time? The most attractive place in the world for a company where it has the ability to be memed or consumer loved like never before, but also at the same time be the single most hellish spot on earth and it's both the same time for two very different sets of companies.
- [53:40]
Rory O'Driscoll
Yes, it sucks. It's problematic for the public markets because yes, you have this thing whereby you can only be in this public market when you're pristine and your narrative value is high. The problem with that's not all the companies all the time, which is why the number of public companies continues to decline. I do think at some point it has to be an easier place to be public while you're dealing and managing transitions. If the idea is every time you have to deal with a problem you have to go private to fix it. That strikes me as a little absurd. And it's a combination of lawsuit avoidance, board exposure, I think indexing and very much shareholder bases that have little patience activists. There's a whole bunch of reasons why it's shitty to be public and the only good reason to be public is when you're hot. Capital is dirt cheap and there's lots of it. That's an okay value proposition for the best companies in terms of going public, but it's not a great value proposition.
- [54:31]
Harry Stebbings
Overall, I'm excited To you mentioned OpenAI there as one of the companies diving the line. Very big news was openclaw creator. I'm going to probably mispronounce it, but Peter Steinberger joining OpenAI, the open source bot becoming a foundation. How do we break this down? Jason, I'm so intrigued to hear your thoughts on this because you spoke about how Malt Book was running different agents and how you were experimenting with it. How did you analyze the news of the acquisition by OpenAI and Peter's joining
- [54:57]
Jason Lemkin
OpenAI on the one hand, when OpenCloud, whatever it was called back then, Claude bot or whatever it was, at first I was like. And I said this to one of the top CTROs I work with, I said, you're going to turn off this. Because I was already there last summer when an agent deleted my entire database. And now, basically what this app does is it's designed to break guardrails. It's designed to allow you to go onto your C drive and onto your desktop and access things that the leaders don't want you to do because they know it's a problem. And it's designed to sort of run pseudo, not really, but pseudo autonomously. 24 7, which anthropic or OpenAI could do, but chose not to do. So I'm like, you're going to churn off. It's a dalliance, right? It's a proof of concept. Probably still true. You're not seeing amazing applications in the last month that have come out of it, but one, it has ignited the developer community like something we have not seen in a long time. So buying into that mojo has some value, right? Buying into one of the fastest growing stars on GitHub, fastest growing deployment, the fact that every cool engineer is playing with it, it may be ephemeral value, but it's real, right? The fact that Zuck lost the deal and cloned it on Manus yesterday pretty much shows you the technology itself is not that differentiated. Right now it's available, mostly hosted as of last night on manuscript. So, you know, is it worth 100 million in to open AI? Maybe, if that's what the price. I don't know what the price is,
- [56:24]
Harry Stebbings
but I think this would be worth a billion plus.
- [56:27]
Jason Lemkin
I don't buy that. It was sold for a billion. I don't buy it. But maybe it's true. You have the numbers, I don't do. You know, I think, I think it's about 100. That would be my, my, my guess based on a number of things, maybe it's more obviously, he probably turned down more from Zuckerberg, right? Which is the great insult. But I think what it opened everyone's eyes to is that, hey, we. And I think this is why Anthropic was so dismissive of it at first, was the safe thing is we don't want semi autonomous agents running. We don't want agents running rogue 247 with no guardrails. Okay? Breaking guardrails, saying crazy like this is today's. AI nightmare. There's future AI nightmares coming.
- [57:08]
Harry Stebbings
But.
- [57:08]
Jason Lemkin
But it's too late. I think it's too late now. Like now every developer wants to develop truly autonomous agents. And whether this platform will decline, right? If he gets bored and goes on to the next thing or not, I don't know. But the horses left the stables for these autonomous agents and the risks associated with them. There's no reason that that open Anthropic couldn't build this last year. They just didn't think it was safe. They just didn't think it was safe. But it's too late now. Just like Elon said. Whatever. Six months ago. I wish we could delay AI three to four years, but since we can, I'm going all in on Xai. I think this is the moment where we shouldn't be doing these semi autonomous agents, but it's too late. We're doing them anyway. So the risk has been elevated, but the developers have just. Everyone's excited. So the amount of innovation that will come, it's hard to predict, right? When all of our apps run 24. Seven, making their own decisions, deciding whether guardrails are appropriate, working around them.
- [58:02]
Harry Stebbings
You know, Jason, what does this do for inference requirements?
- [58:06]
Jason Lemkin
In theory? It's, it's, it's. That's an untenable thing, right? That's why we're not only buying Mac Minis, we're buying Mac Studios that can run a full model on the Mac. The, you know, the 4000 or 6000$. Max. Max Studios. But we'll figure it out, right? I mean, you know, listen, there's a limit of my expertise, but you can run 24. 7, right? And you can run on mini models and you can run on. On. Sorry, I use it. What's the really cheap one from Anthropic? It costs almost nothing. So I think, listen, you can't run Opus 4.6, 24. 7 and not bankrupt yourself, but maybe you run Haiku 4. 5 and you're actually not running it 24 7. You're running it every 20 minutes, right? And so you figure out the cost. Haiku is like a 20th the cost of Opus 4.6. It's manageable, especially for apps where there's budget. I don't know. I think we'll figure it out.
- [58:52]
Rory O'Driscoll
Well, agreed. That was awesome. I think the interesting thing is how does the overlap come between apps for which there's budget and an agent that has that much power on your desktop? Because when I mentioned to my IT guy that I'm planning to download and try it. He pretty much had a connection. So obviously you just have to go and do your own little thing offline. But I agree, it was like, wow, this is the agent on Trammel with no controls over what it can do on your desktop. That's obviously not a sustainable corporate thing. But as you say, Jason, it opened everyone's eyes to what you could do if you had this. So now there's going to be a whole plethora of how do you have it untrammeled, but with some kind of security guard, some kind of controls, and to get the positives of it without kind of literally having it nuke your entire hard drive or delete everything on your hard drive. But it's the way it's going. It was great.
- [59:42]
Jason Lemkin
One of the things people got excited about in Opus 4.6 was that it was easier to spawn a bunch of agents. You could spawn six or eight agents that would go off and do things at the same time. The humans spawn. I'm sure it's true. In level 2, I know on the next release of repl.it not only does it happen because they've built their own set of guardrails, but the agents do it at night. So in the. I know in the next release of Replit, when you log in the next day, it will have built three to four features for you on its own. On its own. That's coming like in the next release in v4 of Replit. So imagine that happens to every app where you go to bed and you wake up in the morning and it's done all your general ledger, it's done all of your what, whatever, And. And you can say maybe it'll be slower to accounting this and that. It will have built all of your assets. It will have rebuilt your entire website. That might be a threat to Canva. Well, when you go to bed and you wake up in the morning, it's built four versions of your website. And I'm not saying others won't do it. I'm saying Vercel and Level. But I know this isn't the next release of repl. That's pretty disruptive. And Open Claw is kind of like the hippie version of that. It's cool. We may not all use this exact product as it is today, but the idea of autonomous agents doing work for us, I mean, it's. It's coming in 2026, and part of it is pretty scary.
- [60:49]
Rory O'Driscoll
In one sense, you are. Anyone could have done it. But maybe in the big labs, they Said you shouldn't. And you think this guy just put it out there. And everyone went, yeah.
- [60:56]
Jason Lemkin
That's why Anthropic threatened to sue them. They're like, this isn't safe. This is the last thing we want to do. Get our name off this horrific thing that's going to go and release. And just, you know, because when both Openclaw and Moat Book immediately published everyone's private keys, private passwords, private. They're like, this is exactly why we have a safety team. Yeah, we're going to sue you if you use our name. This is terrible. But then every single developer thought this was off to, you know, off to the Apple Store or worst case Best Buy. They're buying Mac Minis, Mac Studios. No one was more excited to spend nights and weekends building these things. And that's why folks are like anthropic fumbled this. I mean maybe it's just the world like they thought this was the wrong thing to do. Completely unsafe. And Zuck and, and Sam Altman had another a month and a half to think on it and said this is a movement. Like this is a friggin movement in AI.
- [61:45]
Harry Stebbings
You think Anthropic fumbled the bag by not investing in this? By not trying.
- [61:50]
Jason Lemkin
I just think the world changed. This went from something that is a seemingly goofy guy with the shitting grin out of his face and can bench press £400 and it seemed like a goofball guy almost mocking us with this and, and your legal team and it's unsafe and Daro's about safety. We don't want this on our platform. Platform to like utterly the coolest thing that's been built in six or eight weeks. I just think that everything changed. It's. It's just like investing. I don't think they fumbled. It was hard to tell at the time. Maybe threatening to sue them wasn't cool. Maybe the legal department could chill on the next one and just instead of the cease and desist, maybe maybe just chill for another couple weeks. Maybe that was the error. But I think it was too early to know would be a movement. If you talk to CTOs in your portfolio, it just all. Whatever it was, it was only like two weeks ago, right? Just all of a sudden everyone was using this two weeks ago. Everybody. And I'm like, you're not going to like this, man. It's going to delete your database, it's going to steal your credit cards and
- [62:44]
Rory O'Driscoll
they're like but look what it can do.
- [62:46]
Jason Lemkin
But it's so cool. But okay, what's the great app that you did. Well, I built a TikTok and it sent. It sent an email for me last night. Oh, great.
- [62:54]
Rory O'Driscoll
What it's worth, I think that's a great take, Jason, because you're right. My initial was oh my God, this anthropic funnel. But you're exactly right. You set yourself up as a safety company. You're extremely careful about what you allow to have happen. That has been your brand and a wildly successful brand. You're right. The idea of some cowboy pretty much half taking your name and doing almost. I can see why they reacted as if they've been stuck with a stick.
- [63:17]
Jason Lemkin
The fact that Manus built this in one night said it wasn't about building the technology. You could do it in one day and just. We underestimate how important these guardrails are. They're doing everything from what the agent says to folks that have suicidal thoughts to how they're interacting with your data. You know, the easiest thing in the world is just to take a guardrail off and sell. It's like selling data. Like the. One of the easiest things to do is sell data you're not supposed to sell. Right. Data brokers. Another thing that may be easy to explode is removing a guardrail you're not supposed to remove. You might get a million developers to
- [63:43]
Rory O'Driscoll
use that in two weeks to grab for details. Yeah, yeah.
- [63:47]
Harry Stebbings
Who is the responsible provider of guardrails, do we think? I don't want to get into like two into. But is it, you know, the vendor who's offering the agent? Is it the data holder which holds the data, your salesforce, your servicenows or you name it? Or is it an independent third party that sits as a layer between.
- [64:04]
Jason Lemkin
I think we're learning. Right. I think there's a lot of responsibility. I've talked with a lot of the chief officers and others at some of those public companies and there is a weight of responsibility on their shoulders for what these agents do that the guy from openclaw don't have. Okay. He's. He don't have that weight on his shoulders.
- [64:19]
Rory O'Driscoll
And with a. Jason, were they tech?
- [64:21]
Jason Lemkin
Probably.
- [64:21]
Rory O'Driscoll
Providers are tech users.
- [64:23]
Jason Lemkin
Some of the top shape answers at public B2B companies have a lot of weight on their shoulders about. About responsibility for their own guardrails, which are much more narrower than what OpenAI and Anthropic have. I mean you take the guardrail off, open. I can shoot a gun, you know, hook. Hook a gun up to your LLM change the outcome of the LLM and say someone's threatening my home and it, it takes it the other way and it's shoots. It could shoot a person. Ask your LM if it could do that. It could say it's possible. Right. You got to have the guardrails. Especially if you hook it up to the real world. Take someone that's it's angry in the world and allow an LLM to control that crazy things could happen. So I think the weight of responsibility is huge for guardrails. It is. It's massive. It's massive.
- [65:06]
Rory O'Driscoll
Yeah. Again without. I mean look, leaving gun comments aside because I think it's a little far fresh right now. You are right. If I'm a B2B software company and my agent goes from a very constrained agent that I'm selling to third parties, goes from a very constrained agent to something like the slightly safer equivalent of OpenClaw. You're selling a software product to your customers that can exfiltrate all their data. You could make a 24 hour career ending company ending move here. You're right. So you are actually now that I think about it, those guys are bargain. Because Harry, to your point there's two separate questions. I mean you said who's responsible for this? I actually think it breaks it to who's going to be fired if they get it wrong and then what software will there exist to help. Sure. They don't get it wrong. And those are separate questions. My guess the answer to the former is anyone responsible for initiating these. No one's going to care whose fault it is. If you let it into your company and it goes crazy, you'll be blamed.
- [65:58]
Harry Stebbings
I think there's multi layered to that because lots of different people can bring in software but CISOs chief security officers will be blamed. Also there's multiple.
- [66:07]
Rory O'Driscoll
Absolutely. So my guess is even as we speak there's people building really compelling agent first security products to make darn sure that doesn't happen.
- [66:16]
Harry Stebbings
And we are about to invest in one.
- [66:18]
Rory O'Driscoll
Of course you are.
- [66:19]
Harry Stebbings
Because of course we are. You know what, that's great. But what about me? Can we change the title of the show to that?
- [66:25]
Rory O'Driscoll
I think it's whatever you want.
- [66:27]
Harry Stebbings
I catchy ring to it before.
- [66:29]
Rory O'Driscoll
Before we.
- [66:30]
Harry Stebbings
I do want to discuss actually you can choose which one you think is more interesting. Workday and the CEO transition there and then thrive in the $10 billion now $9 billion for growth actually. I know it seems less than Andreessen's 15 but actually their growth vehicle is bigger than Andreessen's at 6 my question on Thrive is just like how much bigger funds do we get in venture? Is LightSpeed and GC going to come out with 20?
- [66:55]
Rory O'Driscoll
I mean again as we said, thinking of it as early stage venture is just a mistake. It's yeah. How big should a fund be when companies raise $30 billion rounds? Now there's only a few companies who raise those kind of rounds but if there's four or five companies valued at north of $100 billion which is the two model companies, SpaceX, Stripe and Databricks. Again when you deal with $100 billion plus market cap companies potentially wanting them as much as a trillion, a typical 5% ownership position is 5 billion bucks. It's just mad. So as long as these companies are staying private, the growth funds to finance them are going to get bigger. It's as simple as that. We said it in one of the shows earlier on Tribe has done an amazing stock picking job of backing stripe, of backing data breaks, of backing OpenAI and backing them at scale. The companies need the money. The investors who have money want to get in those companies. Tribe is in the middle saying I'll make this happen. I go back to my comment. In a more sensible world all these companies will be public and we wouldn't have to pay all these fees to just someone could buy Fidelity Small Cap Growth and get actually in this case Mid Cap and Large cap growth pay 50bps and buy the same stock. But in a world where these companies stay private, the need for someone like a thrive with $10 billion is acute. And they've stepped up and filled the need and there's probably room for more.
- [68:13]
Jason Lemkin
Plus it makes it simple when you're Thrive and your model is to do every round, not to back off. When the number gets big, your fund becomes fairly simple. You quickly consume whatever the maximum amount your winners can consume. Where you have your super pro rata it's just if you don't, if you don't beg off at the 380 billion or the 760 billion dollar round, it actually makes your fund construction much simpler. Get into the winner and do all of the rounds. Just do all of them the maximum you can as long as the numbers work. It's a very calming model that the partner meeting is very simple. Anthropic also wants to raise it 800 billion. We can do 3 billion in to be fair it's just. It's our model. It's our model we're in next. Harry has, Harry has this AI agent company. I don't know about that one.
- [68:57]
Rory O'Driscoll
I'm going to give them credit though. They actually specifically unlike some of the other funds I've invested in both, they've specifically our fund that said no, we backed Open AI. We're not going to back on Tropics. So they at least I should have
- [69:07]
Jason Lemkin
said OpenAI is raising monogamous here.
- [69:09]
Rory O'Driscoll
You know one thing I do think
- [69:11]
Harry Stebbings
is interesting is actually in the same week we saw Arafian Muhammad, who I'm sure you guys know just through years in the Valley, I've known three years in Valley announcing that he was leaving and starting his own thing. We saw Max Gazelle leave CRV and start his own thing. Striker. The question to me is as we start seeing these Aum gatherers to the extreme, are we just going to see a continuing flow of these great operators within firms? And I really respect Arif. I'm sure you guys do. Leaving in the desire to return to early venture.
- [69:41]
Jason Lemkin
I don't know. It's always about money. I mean peak. Peak 15 almost imploded, right? Because the managing partner wanted to keep all the economics right just the other day. It's. It's not about getting back to who wants to get back to early stage. I want to do the anthropic round. Give me a fucking break.
- [69:56]
Rory O'Driscoll
I don't want, I don't want to
- [69:57]
Jason Lemkin
like have to pick which, which accounting software in four years might break out for AI. No one wants to do that. Just show me the carry.
- [70:05]
Harry Stebbings
I don't think that's true. I do think there are people who've made it. You know, bluntly, I'm sure Arabs made a fuck ton of money. And I think he loves working with founders and I think he's bored of the bureaucracy of a big firm and he's like, I want to go back to picking cool founders and having fun.
- [70:21]
Rory O'Driscoll
Yeah, there's definitely some of that. I mean, Jason, your cynicism is often warranted and there's often overlays. But first of all, there's the human need to want to do your own thing, which you just got to respect. You're very post economic. Do you really want to be sitting there with five other people having an opinion on your deals? At some point you kind of go, maybe I just don't want to do it this way.
- [70:40]
Jason Lemkin
You might if you like them.
- [70:41]
Rory O'Driscoll
You might if you like them. But then if they have too many opinions, you might find you not like them. Look, the two of you guys are solo gp, so I can speak to this. My point is simply It's a little bit reductionist to say it's about the money though that can be a part of it. There's also a sense of autonomy and then there is a sense of if you're running a big firm, especially a multi stage firm, first of all as a senior lead a lot of your time is spent on firm management stuff is my guess. And on top of that you're right. 90% of the decision making is about do you in Lightspeed Kate brilliantly lead the 60 billion pre rounded entropic and it's not about do you put 10 million into this early stage founder. And if that's what you want to do and you've made a gazillion dollars, go do it for sure.
- [71:24]
Jason Lemkin
For sure. There's no question that I mean I certainly if it were me and I was a partner at Lightspeed and I was the same person I'm today, I would retire into my own fund. Right. Just to not deal with the bureaucracy.
- [71:35]
Rory O'Driscoll
Right Jason, They're a well run firm that get you first.
- [71:39]
Harry Stebbings
But the thing is you'd be pushed.
- [71:41]
Jason Lemkin
But the thing is maybe they're kind of but walking away. Very few firms I'm sure scale's different. Very few firms and. And Harry has more data than me are kind with carry vesting when you leave. Very few firms are kind. I mean Chamath all his ex partners have sued him. Mamoon sued him. The grok guys he sued like there's. I'm just saying people aren't as kind to carry when you leave. I'm not saying like now Lightspeed might be the opposite. They might be the kindest and I know some are kinder than I would have expected expected. But my, my meta point is it's not simple to walk away from vesting.
- [72:12]
Rory O'Driscoll
No agree.
- [72:13]
Jason Lemkin
It's not simple. It's not this, these are carries many funds now vest over 10 years. Some even backload carry because they want to penalize the folks that leave. It is not free to walk away in many cases from a successful fund. Right where you literally could just half check out.
- [72:30]
Rory O'Driscoll
There is a significant economic cost at any point. I mean look especially if successful and the more successful the fund and Lightspeed having an amazing run the more more more the cost is. You're right that anyone leaving is going even it. Even if there's nothing kind of crazy, even if there's no loss of carry you're still walking away from unvested embedded value again back to being post economic
- [72:49]
Jason Lemkin
and you got to start from scratch.
- [72:50]
Rory O'Driscoll
Oh yeah, it's a lot.
- [72:51]
Jason Lemkin
As great as it is to work with these early stage founders, I'm walking away from a couple hundred million of carry. I get to start from scratch and maybe in 18 years I get back. As long as you start when you're 18 like Harry did, it's easy because then at 34 you're back to where you were. But RF looks pretty young, but I don't think he's 18. I mean he's pretty fit, he's got the hair. But 18 years could be a while, dude.
- [73:12]
Harry Stebbings
Starting young was such a competitive advice. I was lucky. I didn't realize how starting so young. Guys, we can choose one more topic. Is there one more topic that we have to discuss? Netherlands High sport and work day. Any that jump out.
- [73:28]
Jason Lemkin
I don't want to overdo the workday thing, but man, it is interesting that Aneel had to go back in like eight months to run workday. That's a pretty fast boomerang, you know. And Owen at Intercom makes the point constantly that this is the age for the founder CEO. And I agree with him 7896%. Right. You think Anil wanted to go back as the solo CEO just as much as Daniel wanted to go back to UiPath. I mean these guys were chilling, but he couldn't even make it a year. Right. And so it goes to Rory, Rory's earlier point. I'm not challenging you, but your point that some folks spaces will see the impact more slowly. You would think workday would be one of those spaces that isn't going to be disrupted overnight and Aneel had to come back as CEO.
- [74:10]
Rory O'Driscoll
That's a fair pushback and what it says because what I do agree is it. And you know, again, Carlos Mac, widely talented executive. But what you're seeing here maybe is a combination of what the problem is not is go to market what the core problem is product roadmap. And typically that's where a founder can do really well. I can imagine that that's the narrative here and it probably makes sense because yeah, Jason, you're right, it is interesting. I would have guessed HR software and financials would have had a long lead time to adapt to AI. And it's not obvious that I don't think something AI agentic is going to displace the whole damn thing tomorrow. So it is a canary in the coal mine that they felt the need to make that change. And I probably should go in and think about that a little more. It'll be interesting to see was it, is it product roadmap anxiety, is it identity crisis anxiety or is there something specific it would be interesting to see then what changes in 12 months. And that's probably how you judge this thing.
- [75:05]
Jason Lemkin
I think a lot of these boards don't want this too. They want the founder back right now there's too much disruption and you can't. This was Owen's point too. You talk to folks at Salesforce, this is why you should bet on Salesforce. Of, I mean listen, Most, most public B2B companies are founder led, right? Most of them are. But the amount of stress in that organization is so high at Salesforce. And it's a good thing because Mark is driving mass now we can, we'll see whether it's successful. Right? But he's driving more change the last eight months than the decade before that. And who but a founder could drive that level of stress and anxiety and change across the company? Like everyone, everyone thinks they've got to step it up. Right? And it's just as an outside CEO hanging out at the SKO RKO in Cancun, it's just hard to drive that change.
- [75:50]
Rory O'Driscoll
I think you are and it's funny and I was thinking about this because I normally I try and be contrarian and one of the things I try and say is, is that really true? Can it just be the founder? You know, you love founders, you back founders but you also want to try and not over dramatize or over attribute uniqueness to founders because you know, at scale companies they all have to be run by non founders. But I've decided in this case you're right. Because if you have to do a turnaround with a problem or a business challenge, I can totally see a hired executive saying we got a cost problem, we got a go to market problem, we got a segmentation problem. All those things are classic playbooks and there's lots of folks to get. But if the problem is the core thing you built has to be changed for a new way of building it, then having the memory of how you built it, what were the business choices you made and the kind of customer choices you made 10 or 15 years ago when you were building it the first time, my guess is you're right. That's a problem where uniquely the founder, if they are flexible, can say I know the trade offs I made before someone from the outside would take two years to even figure it out. I just know can we do it this way? In this case, I think you are right. Jason, is that you Just come to the table. Maybe the way to crisply articulate it is what you don't need in this kind of situation is generic business skills. What you need is massively specific knowledge and skills and courage to make the changes that you know you have to make. And that is where a founder's advantage.
- [77:13]
Harry Stebbings
Do you think it will work bringing ANEEL back? The board is clearly trying to increase share price over the long term. Do you think ANEEL will be able to increase the share price significantly in a 12 to 24 month period?
- [77:26]
Rory O'Driscoll
I don't have a developed opinion because I think that again, it's back to the. I don't think there is a magic pixie dust that can make the growth rate of this category change from what it is now to something dramatically different. It's not even like the figma example where you say there was an adjacency and if you pick it up you'll get another 40% lift. I think this is a mature, established category. Yes, you've got to add AI. You got to tell the story. But it's not obvious to me that there's a magic fix. It may well be a combination of a whole bunch of fixes, including on product add up to a better growth rate. I don't have enough opinion to it.
- [78:00]
Jason Lemkin
I think at least he will drive faster change and he'll make quicker bets. Whether he's the Jobs coming back to Apple or Schultz coming back to Starbucks.
- [78:09]
Rory O'Driscoll
We don't, we don't know.
- [78:10]
Jason Lemkin
I think a lot of these bets won't work. But I'd rather have him running Workday or Daniel running UiPath. Because here's the thing, the amount of resistance to change is so high on the employee base. This is the thing. It's not just that the founder can make these just two year decisions in two weeks. To Rory's point, it's not just Michael Cannon Brooks's point that he can make five year decisions and today decisions at the same time, which an outside CEO struggles with. Right? Because if he makes five year decisions, you lose your job if you don't see growth. Right. It's not just that those are hard enough, but no one wants to do the work in the age of AI. You got to go talk to the regular VPs of these tech companies. None of them want to do the work. It is just so hard to drive change when most of your employees do not want to do what it takes to change. And you can say that's not true. But I talk to senior execs at these companies all the time. They, everyone wants to do the same job of 2023. That is human nature. They all want to do it. And, and the smart folks actually are quitting all these companies and they're going to hot air companies that are hiring recycled SaaS executives where it's just easier. That's what you should do. You should immediately quit these public companies and go to the hottest AI companies where the product almost sells itself. Here's the thing. The 2023, 2022 toolkit works perfectly well at the hottest AI companies. It really does. It really does.
- [79:27]
Harry Stebbings
I released a show with the head of sales at 11 lab.
- [79:29]
Jason Lemkin
It was good.
- [79:30]
Harry Stebbings
Insanely popular show. I mean, I can't even tell you how insanely popular it was. The thing that everyone oscillated around was the 20x sales comp. If you want to succeed in 11 labs in the sales team, you have a 20x on your head. If you don't hit it, you're out.
- [79:44]
Jason Lemkin
Yeah, but I was with another one, another, another AI leader where the sales team has 4 million dollar quotas. That's basically 11 labs. Matt, they just rolled out their, their 2026 plan. It's a $4 million quota.
- [79:54]
Rory O'Driscoll
I saw the commentary on that. And it's. Someone said it's not that you're hiring because the typical SaaS quota is around a million bucks. It's not that they're hiring forex better salespeople at 11 labs. It's that when people want to buy your shit, it's easy to sell it. It gets back to the same thing. It's all about momentum in the short term. And the customers have woken up and said these are the two or three things we want to buy in 2025 and 2026. And if you're in those things, you can sell, you can grow like crazy. Your stock price can go up. And if you're not, it's damn hard. It's just the constant reminder of just keep it simple. Invest in companies that are in markets that are exploding right now. End of complex analysis.
- [80:34]
Harry Stebbings
I agree. Final one. And it's a batch.
- [80:37]
Rory O'Driscoll
Okay.
- [80:37]
Harry Stebbings
Oh yeah, don't worry, it's going to be great. Okay. Which public company founder will return to the CEO seat, which they left next?
- [80:47]
Jason Lemkin
I say it ain't going to be Dustin Moskovitz. Man, he just left the keys on the table. Yeah, I quit. This job is stressful. I don't like people. I quit.
- [80:57]
Harry Stebbings
Dude. I'm with an anthropic holding. Like he has I totally don't blame him. Yeah. Halligan. Sorry, Rory, you can recuse yourself from this conversation.
- [81:04]
Rory O'Driscoll
I know nothing. I mean, when we're long since out of that, I think.
- [81:07]
Harry Stebbings
Yeah, yeah. But like, you know, you're looking at 12 and a half billion now. Market cap for them down 45 in the last six months. Halligan sitting there. I love Brian. He's amazing. We all do. Amazing.
- [81:17]
Jason Lemkin
You know, it's not fair because, I mean, maybe I. HubSpot and GitLab are the only candidates I can think of where there's just not enough boomerang. I don't think Brian's going back and. And Sid is. Sid seems off. You know, he had his cancer scare, but he seems off on his own initiatives. But I can't think maybe I'm missing, so I can't. There just aren't enough, like, there's too many Michael Cannon Brooks out there for this. For we. There's not enough candidates.
- [81:41]
Rory O'Driscoll
That's exactly right. And you know, another candidate who obviously won't happen, but it was. Was great guest Jeff Lawson, who was at Twilio, is now like, I'm doing Fusion. You. You people knock yourself out. Which are like telco stuff.
- [81:53]
Jason Lemkin
Yeah. Jeff could have been one if the ball had bounced another way. But he's not likely going back, Right? Yeah.
- [81:57]
Rory O'Driscoll
And given that the activists were mean to him, why would he bother? Again, back to the same thing. Why would I flog my way through that one when I came out?
- [82:04]
Jason Lemkin
Well, I think you'd get over the act. Like, I. I mean, Jeff was very direct. It was a great. It was really a great show. Greater than people realized. Right. My limited experiences when you're treated terribly as a CEO was like, Jeff is if people come back with humble pie and you care, you get over it.
- [82:18]
Rory O'Driscoll
Yeah. You.
- [82:19]
Jason Lemkin
You got to pay the price. Like, they might have to have to have given them a half billion dollar package. But if there's a little humble pie, you get, like, you, you. You know, you get, you. You analyze. You get over it. Right. Especially the activists are gone. You get over it.
- [82:31]
Rory O'Driscoll
But, yeah, not enough sample set, Harry. So we're ruling the question out of order.
- [82:34]
Jason Lemkin
The more interesting one, which I would not touch, is who's going to quit next?
- [82:38]
Harry Stebbings
Oh, good question. Who's gonna quit next, Jason?
- [82:43]
Jason Lemkin
I don't know, man.
- [82:44]
Harry Stebbings
You know, who deserves prizes for persistence and resilience on. And I love Drew from Dropbox and Aaron from Box. Just unwavering, resilient, persistent.
- [82:56]
Rory O'Driscoll
Yeah. As you know, I was on the Aaron's board for many. I. I just admire those guys for going in and out. Because it's so hard. I mean, especially now when, you know, blabber mounts like us on podcasts are saying. Nothing you do matters. You just don't care. Yeah. The ability to keep grinding on is actually very impressive. It really is.
- [83:15]
Jason Lemkin
You know who, you know who just retired? Dave Gerard. Right. He said he was 60. He's retired. Right. So there is a. There's a wall of 60. I barely know him, but he's pretty young, right. Externally. But there is a wall of life where it might happen. And then there's, you know, I don't. For Sal, I was just looking at Yelp this week. I mean, Yelp's down to $1.2 billion valuation. I mean, Jeremy's young, but it's been, what, 20 something years, right? And it's down 47% this year to almost just over a billion. He's great. Right? But ones like that might be vulnerable to personal issues or other. Like, it's just not. At some point, it creeps into the hundreds of millions. It's just like, you know, like, good luck.
- [83:56]
Rory O'Driscoll
But as, as my. As long as the founder wants to keep doing it, go team. You know, it's. I just admire. I just admire the grind.
- [84:03]
Harry Stebbings
Monday at 3.8 billion. Is that a buy or not?
- [84:07]
Rory O'Driscoll
Again, the thing is, how I can make a comment here. Let me tell you why I'm going to answer it very quickly.
- [84:12]
Harry Stebbings
Well, I'm going to give you some detail because I know what you're going
- [84:14]
Rory O'Driscoll
to say before you do. You have to give it. Because the interesting comment is this narrative. Stocks you can get away with on a momentum story. Right? So you're right, is that you could have asked me about Pick an AI store. I'm like, yeah, the market, they're the leader. Buy at any price. You're right. When you're dealing with something like Monday, you got to look at the revenue, the growth rate, the free cash flow, the SBC, the DCF. And it's a grind. And you're still playing for 15% IRR.
- [84:39]
Harry Stebbings
All right, grandpa, we got 1.25 billion in revenue at 27% year on year growth. 2026 guidance expects 1.45 billion. Non GAAP operating income, 175, 14% operating margin. Would you buy or sell?
- [84:57]
Rory O'Driscoll
The free cash flow was. What do you say the free cash flow was?
- [85:00]
Harry Stebbings
Non GAAP operating was 175, 14% operating margin.
- [85:05]
Rory O'Driscoll
I mean, it's about right. It's like 10 times plus or minus, it's 1.7 billion. What's the stock position? And you said the market cap is 3 billion and I bet you they have a billion in cash. Yeah, it's 3.5 billion of market cap. Yeah. I mean, it's the classic. Maybe to make the positive one, there's two questions. If you can manage the sbc, which is a minor but important question, and the major question is 10 times cash flow for something growing sustainably at 20% is wildly cheap. The question is, it goes back to Jason's comment is how durable is that growth rate? And if you have a product roadmap that can survive in the age of AI, that's probably an underpriced stock. If you're destined, as Jason described earlier, to the gradual attenuation of your business, then you have to price this thing as if it can go away entirely and you end up in a different place. So it all boils down to product roadmap, product direction, the age of AI.
- [85:52]
Jason Lemkin
I mean, if you believe it's durable, which we all did in December, then the fact that the stock's down 51.3% of the year makes it the screaming buy of the value stocks of the public cloud companies. If you believe, and we all believed it was durable just in December. Has it really? I mean, I do believe it's changed for this whole conversation, but if you don't believe it's changed that much in 47 days, this is the greatest buy that there is this Monday. You should just load up on Monday especially. And you have great founders. This is still a founder led company. You have two founders at the top, incredibly driven, incredibly ethical, who know their market cold, who are still selling primarily outside of tech. Right. Which has less disruption. How could you, if you believe the revenue is durable, how could you not buy this one? You must be saying, we believe that none of this revenue is durable anymore.
- [86:39]
Rory O'Driscoll
Do you have a durable matrix in your head? Like, I'm just going to do durability of this versus Salesforce. Let's take Salesforce because it is the original stuff. Stuff like let's make benchmark of 1. Do you think this is more durable, less durable than Salesforce?
- [86:52]
Jason Lemkin
I am long on Salesforce as a platform for agentic agents. For real. But the fact that we are at 10% growth with a lot of inorganic acquisition and a lot of price increases doesn't suggest high durability, does it? And I mean, durability means it has to organically grow. Durability doesn't count as dial up at AOL shrinking every year. Okay, that's not durable. That we have a 30 year business. Durable always meant for B2B. We have over 100% net revenue retention for real. Not just based on price increases and threats. And that means no matter what we do next year, we're bigger. The only question is how much bigger. That's durable.
- [87:29]
Rory O'Driscoll
How? He's waving his hand as if to say, go and get.
- [87:32]
Harry Stebbings
Give us an answer, dude, what do I.
- [87:34]
Jason Lemkin
What's that being a Rory.
- [87:35]
Harry Stebbings
What's more durable? Is it Monday or is it Salesforce?
- [87:39]
Jason Lemkin
So the question is Monday or Salesforce?
- [87:41]
Rory O'Driscoll
Yeah, yeah.
- [87:41]
Harry Stebbings
What's more durable?
- [87:43]
Jason Lemkin
I think they're the same. We just, just SMBs happen faster. It may make sense to be more skeptical of Monday and HubSpot only because SMBs buy faster, they churn faster, everything's faster. And ServiceNow will be the slowest. 99% GRR. With five year contracts. I mean, you know, it'll, it'll, it'll be the next generation that'll really see that decline. Right? Five year contracts, 99% grrr. Are the Mondays will turn faster than HubSpot. Right. And HubSpot will turn faster than Salesforce. It's just, it's just delayed churn. Right? That, that's the thing is, you know, ServiceNow takes you 10 years to get off that platform.
- [88:17]
Rory O'Driscoll
So you've got. I mean, but you're oscillating here. Between a minute ago you're saying, hey, we used to believe it was durable in December. Now it's down 50%.
- [88:24]
Jason Lemkin
Look, I gotta tell you, so, So I wanted to do. For the Show, I think two weeks ago I wanted to go and buy 200 grand for fun. Four stocks, okay? Shopify was my top one. Okay? And I want to do four. And I thought it would just be fun because I'm like, look, worst case, it goes down another 20. I lose 40 grand. But I can write off the loss. It's really 20 grand in California because our taxes are 50. I'm like, this will be fun for the show. I could, I did it last year, actually. I don't want to tell you what the companies were because we're already invested in some. But I couldn't do it. I couldn't do it. And I love shop fights because I just, I don't see the floor. This is me at my gut. Like, I just want to do it for fun, for the con, for the content. For the content.
- [89:00]
Harry Stebbings
You don't see the. Dude, I'll I'll match you. You don't see the floor for Shopify?
- [89:04]
Jason Lemkin
I did. I was going to buy it right before earnings, and it crushed earnings, and it didn't help.
- [89:10]
Harry Stebbings
Bummer, isn't it?
- [89:11]
Rory O'Driscoll
Yeah.
- [89:11]
Jason Lemkin
And I'm like, well. And then I said, you know what? I want to do this for the show, for the content, but I'll wait until after earnings. And then it blew out the quarter and it didn't help. And I'm like, I'll still do the bet. But my. My honest point is, I was going to do it for the content, and I didn't actually do it. Like, I'm like, I. I didn't do it.
- [89:28]
Rory O'Driscoll
You couldn't. You just look.
- [89:29]
Jason Lemkin
And the worst exposure was. Was 20,000. I'm not saying it's not nothing, but it's not as dramatic as it sounds. Right? Because you know it's not going to go to zero. I'm like, and why the hell didn't I do it? It's just because I. I couldn't see it. I couldn't see the bottom. But we could do it for next week. We could all. We could do the 200. We got to pick four candidates. We got to pick four candidates.
- [89:49]
Harry Stebbings
What one are you going to buy? Going to buy shop?
- [89:52]
Jason Lemkin
No, we got to buy. You got to put in 200 grand, and we each pick four candidates. 50 grand for each. And we. We watch it for the rest of the year. No, because this isn't a startup. You're not going. You're not going to lose 200,000. Rory's not going to agree. You're not going to lose $200,000 at
- [90:06]
Rory O'Driscoll
10 times cash flow.
- [90:07]
Jason Lemkin
No. Yeah, it's not as big a risk as it sounds. So we got to pick four by next week, and I'm going to put Shopify at the top of my list again, like, just. But I. I'll do it. Let's do this.
- [90:16]
Harry Stebbings
We're going to do this, but we're going to announce which forward choosing next week.
- [90:21]
Rory O'Driscoll
I need two weeks. I'm traveling, guys. Sorry. I need to think.
- [90:25]
Jason Lemkin
Okay, not trying to force you. Harry and I are going to do it. We got to show the receipts. It's 50 grand into. This is not the end of the world. It's 50 grand into. Pick your four publics and we'll. We'll. We'll watch them ride. We'll see what happens.
- [90:37]
Rory O'Driscoll
Okay.
- [90:38]
Harry Stebbings
I need a sales loft. Hell, just throwing around 200ks just for content shares. Okay.
- [90:44]
Jason Lemkin
I think the competition gone up. Everyone's got a podcast.
- [90:48]
Rory O'Driscoll
I think you are right though. It does force that discussion of what do you really believe? Because it is telling that you. You went to write the check and just.
- [90:55]
Jason Lemkin
It really is. I just thought it'd be fun to come on the show this, I guess last week and say it's not that I'm. I'm Mr. AI, but like Shopify can't do any worse, right? And I just didn't do it. Like, I don't know why I just didn't.
- [91:06]
Rory O'Driscoll
It could be fun.
- [91:08]
Jason Lemkin
All right. Two weeks at least. Harry and I got. We got two weeks. Do you pick your four?
- [91:10]
Harry Stebbings
Take your time, guys. This has been so much fun. As always, thank you. You've been awesome.
- [91:15]
Jason Lemkin
Rock and roll.
- [91:18]
Harry Stebbings
But before we leave you today, I run the 20 VC fund and I get this question from founders all the time. Oh, Harry, I can't find a good dot com. Do you have a good hookup? Well, let me tell you now, the answer is always going to be no. I don't have a guy or a gal for that. I do have a recommendation though. If you're building a tech startup, get a tech domain. Tech startup, tech domain. It could not be more obvious. As an investor, I appreciate founders who put thought into their branding. When I see tech in your name, it tells me right away that tech
- [91:51]
Rory O'Driscoll
is at the core of your build.
- [91:52]
Harry Stebbings
It'll say that to your customers too. A clean and sharp domain like tech pays off in the long run. You know nothing. Tech1x Tech, Aurora Tech all of these great tech companies, they all use tech as their domain. These are my two cents. If you're building a tech startup, don't overthink it. Get a tech domain. While tech gives modern companies a home, online checkout helps that home convert by turning traffic into revenue. Digital commerce is exploding, but payments are still where revenue leaks. Checkout.com launched in 2012 to fix that. They don't try and be everything to everyone. No, they just do one thing better than anyone. Digital payments, cloud, native sub 500 millisecond latency and 99.999% uptime. Today that bet has paid off with a $12 billion valuation and 65 plus merchants each processing over a billion dollars annually. 65 doing over a billion annually is insane. Check out Powers. $300 billion in e commerce for brands like Uber, Klarna, ebay, Vinted, and more. Now they're building for Agentic Commerce where AI agents buy on behalf of your customers in real time. Partnering with Visa, MasterCard, Google, Microsoft, and OpenAI now. If you want payments built for what's next? Talk to the team@checkout.com while checkout powers the moment money changes hands, invisible powers the people behind the work. Why don't we hear more real AI success stories from big companies? The models are insanely good, but implementation's the problem. It's really, really hard. There's data all over the place. There's legacy tech and manual workarounds. It's a Ferrari engine in a shopping cart. Meet invisible invisible trains 80% of the top models and then adapts them to the messy reality of your business. Take the Charlotte Hornets NBA team. Invisible took years of game tape and analogue scouting notes to go from uncertainty to a draft pick and summer league championship win in weeks, not seasons. Get the data in order first, and suddenly AI can do almost anything for you in the enterprise. If you want AI that hits the P and L, go to InvisibleTech AI20VC.