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Rory O'Driscoll

You've never seen a company grow 10x in GAAP revenue and run rate year-on-year for 3 years.

So, you're leaning into the singularity here.

Rory O'Driscoll

Wall Street has decided this is the bet they want to make. Capital has decided this is the bet they want to make.

Jason Lemkin

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?

1. Anthropic's $30B Raise at $380B

Who wants to get back to early stage? I want to do the Anthropic round. Give me a [expletive] break. I don't want to have to pick which accounting software in 4 years might break out for AI. [laughter] No one wants to do that. Just show me the carry.

Boys, it is so good to be back. 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 fundraise itself. Anthropic raises $30 billion at a $380 billion post-money valuation. It was originally $10 billion, and it scaled up to a $30 billion round. I'm going to hand the mic over to you. How did we think about this?

2. Workday's Founder Returns as CEO: Will it Work?

Jason Lemkin

I think if you're not that, you're not of interest to 98% of venture. Literally, I had people—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, who I didn't even know would be on the periphery of the investment, shocked me.

Rory can talk about whether it's cheap or not on a forward-multiple basis. There's probably an argument each way. There's an argument that 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 week Thrive raises $10 billion. This is what everybody wants to do. This is the only play in venture when the public markets for software stocks are down 20-some-odd percent this year. This is the play. It is that simple, right? There's almost no other play other than showing up to demo day.

Rory O'Driscoll

I think Jason nailed that—the comment that this is the play. Look, the last 3, 4, 5 rounds have worked. The 2 rounds in 2025 have worked really quickly: the $60 billion round at the start of the year and the $160 billion round at the end of the year.

Remember, we talked about it and 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 multistage fund, you just have to put some money in, 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 things that's working. If you eyeball down the unicorn list, what's amazing is—even 2 rounds ago, it was the 2nd- and 3rd-largest unicorn—and it's probably outperformed most of the unicorns that are 1/10 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.

Jason Lemkin

Everyone is wisely getting in on the momentum play. The thing that I think, too, is 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. I've never seen so much money chase seemingly such a small, concentrated number of companies. That's the insight: everyone's hoping there'll be another Anthropic.

Here's the thing about Anthropic. I was thinking about this with the SaaS crash. Gravity has almost gone up to Jupiter levels in tech. Everything's being pulled down, right? $6 billion is not enough for a slow grower. You've got to be $60 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—on Jupiter or something, because the flip side is everything else is getting pulled down by gravity, down a [expletive] gravity well, right? They're unsellable.

I mean, you look at Apple: up at 70% growth isn't good enough. Navan is coming down. Look at Navan for the gravity well, coming down to a $2 billion market cap. That is a gravity well sucking everything down when the ship can't leave the planet. And so, with Anthropic, it's left the planet. I mean, Claude Code went from $1 billion to $2.5 billion at the end of the year to today, right? That's escape velocity.

The early-stage ones—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 massive gravity well. But if you do, there's $10 billion from Thrive last week and $30 billion from Andreessen. But, man, the gravity is a [expletive] right now. It's a [expletive] gravity.

When you say that, let's be precise about what it is, because I get the analogy. It's almost like a black hole, in the sense that these 2 or 3 companies are sucking everything else in and spitting them out. Exactly what you said. So, over the medium term, is that massive over-extrapolation?

Rory O'Driscoll

I think so. I think there's an element of projection going on here and, you know, a fair amount of discarding babies with the bathwater. But in the short term, we are narrative creatures, right?

The narrative right now is AI is going to eat everything. Within AI, the narrative is arguably less clear, but nonetheless, 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. Once you have that, you can justify any price.

3. Why SaaS Stocks Keep Getting Crushed

Conversely, at the same time, you see everything else just trading down to points where you sit there and go, “Some of these SaaS companies are trading at 8 or 9 times cash flow. Are they really going to go away in that period of time when they're growing 10%, 15%, 20% at the moment?”

So, my guess is, look, in the end it will equilibrate, because that's how price works. But you find yourself trying to articulate what's the forcing function that will break this overinvestment, break the spell, right? And that's actually a hard question.

We're talking a lot about the value of the company, but really you should also be talking about the performance of the company. I mean, this stuff is working. That's the aha: the revenue accelerator we've seen. The sound bite is going to be 3 years of 10x revenue growth. Technically ARR growth, but yeah, revenue growth as well.

And that's not only unusual. I went back and plowed through the early Microsoft, the early Google, the early Compaq. It's unprecedented. I even started trying to adjust for GDP growth and inflation. The truth is, you've never seen a company grow 10x in GAAP revenue and run rate year-on-year for 3 years, right? At this scale, it just hasn't happened.

So, you're leaning into the singularity here. Now, it's worth pointing out that Microsoft, Google, and many of these other companies that had 3x or 4x year-on-year growth for 3 or 4 years were also wildly profitable while they were doing that.

Rory O'Driscoll

This company is still losing a ton of money, but from a growth-rate perspective, this simply has never been seen before. At the margin, we're all growth chasers. What other $380 billion company has a CEO saying, “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.

First of all, you're right, and this is a reference to Dario Amodei's long and awkward podcast, where one of the very sensible things—and I always find him, frankly, way more grounded than some of the other leaders in the space—is that 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 overinvest because the money is so much, you hit the point where you don't get the returns to scale, then you are really long compute.”

I think there was obviously the element of, “And then one could go bust,” but 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.”

But, yeah, it is, again, back to the same thing. These companies aren't like the explosion of growth of internet companies or software companies like Microsoft, because they're wildly capital-intensive. They are much closer to semiconductor companies in terms of structure.

You have to just put in—I mean, even Dario talked about the amount of capex he's looking at over the next 3 to 4 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.

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,” right? And intuitively, you know that you can get the free cash flow by slowing down, and getting to free cash flow probably also assumes slowing down growth.

Jason Lemkin

And once you slow down growth, you wake up and realize, “Well, on a GAAP revenue basis, you did $4.5 billion last year, maybe $15 billion, plus or minus, this year. On a GAAP basis, 30 or 40 times GAAP revenue is a little pricey.” So it’s going to be hard to manage that.

What percentage of the $1 billion to $14 billion in revenue do you think is customer acquisition from OpenAI customers versus net-new customer acquisition?

Jason Lemkin

I never thought about it, but I doubt it’s a huge amount. We’re seeing lots of enterprises 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 level, I actually don’t have insight into that. Someone like OpenRouter might have that, and that’s where it would show up.

To be fair, stepping back a million miles, most of OpenAI’s revenue comes from ChatGPT on the consumer side, and less than 20% of Claude’s revenue is consumer. They’re really slightly separate companies with an overlapping Venn diagram: same raw technology, but one has very much gone to enterprise and coding, while the other is mainly consumer, with some enterprise and coding.

So I don’t think the narrative is—I don’t think the narrative is, at a direct level, that Anthropic’s winning, so OpenAI must be losing. I think the narrative is that venture, and soon Wall Street, just loves AI and doesn’t love anything else.

Still, it is crazy. I don’t think it’s too early for Anthropic to be stealing enterprise deals from OpenAI, because even those deals are 1 year and they’ve just been signed, right? Anthropic said its 100,000 customers are up 7X in the last year. So it’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. You can’t argue with it. Even though the budget is accelerating in ways we’ve never seen before—global software spend is up 14% this year, which is unprecedented—you still have a fixed pie, even if it’s growing. I don’t think anyone thought, when ChatGPT broke out, that Anthropic would have 64% of its revenue at that point. That’s a lot of momentum, right? That’s code red. You thought code red was about Gemini?

Jason Lemkin

I guess it was, but maybe it’s like Missile Command: they’re coming from everywhere.

I think you’re right, Jason, and that’s a great point. There’s a reason, when we were talking about CEO of the year, that it was clearly Dario, because if you look at where the story was a year and a half ago versus where it is now, Anthropic just went in and scooped the money. It can’t be great if you’re the other guy.

Software spend is at a 14% rate, as you said—the highest it’s ever been. What do you think it is in 2030?

Jason Lemkin

Look, software has grown pretty steadily 200 or 300 basis points—2% or 3% above GDP growth—for a couple of decades. That’s the low-rent, low-drama version of the endless “software will eat the world”: it’s growing nicely, but it’s still 3%, plus or minus, of GDP, right?

So the probable answer is that it gets back to the discussion we all just had. 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 GDP plus 200 basis points or stays at GDP plus 400 or 500 is all about whether massive labor, efficiency, and productivity savings come from AI. 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. Competition is tough, but the markets are huge.

Jason Lemkin

But there has to be some bear case. Probably one embedded bear case is: are you really getting the ROI from this $10 billion, $20 billion, or $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 that will be fine, right?

The canary in the coal mine would be if, in a year or 2, 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.

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: 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 bet, just like we’ve always made it in 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. 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.

I see this. It’s not just Dario waving his hands. I mean, he’s great, and all these podcasters. I think enterprises are going to will this into 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.

So, generally, even if it didn’t have to be true, even if this was a little bit less revolutionary and people might back off in 2 or 3 years, they might be like, “You know, I didn’t see the ROI I thought from that Salesforce module or Workday Financials. 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. By the end of this year, that train’s going to be so far out of the station that these growth numbers will be jaw-dropping, because we will decide. Enterprises—the Fortune 500 or Global 2000—will decide, “We are replacing humans with AI,” even if it’s not the right decision.

I think, actually, Jason, you’re right. 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 on Wall Street—Wall Street has decided this is the bet it wants to make. Capital has decided this is the bet it wants to make. People are going to try and make this bet, which is very different from saying that, when they made the bet, they liked the result. But that’s 2 or 3 years out, right?

My gut would be people will overbet, overinvest, and you will have a retrenchment period 2-plus years from now. But I think right now you’re just looking at 2 years where, just as the hyperscalers said 2 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 1 to 2 years of mega AI budgets, not regardless of AI ROI, but on the presumption of success—maybe that’s the 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’ve got to do.

CEOs generally have only 2 or 3 agenda items at any one time. There’s a whole period in the ’90s, Jason, you remember, when it was all about rightsizing and efficiency. Then it became about getting on the internet, then getting on the cloud. You’re right: the number one thing now is, “Make your big AI play.” So everyone’s going to make it. Everyone’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.

Jason Lemkin

Which means that the next 2 years would be a good time to access the capital markets. It’s also why, I hate to say, I want to be really bullish and say that a lot of these public software stocks are oversold. Maybe it’s true, but you know what I mean? Harry just had Sebastian from Klarna on, right? He likes to be a rabble-rouser, but he’s like, “I went from 6,000 to 3,000 employees.” We know that. Then he said on 20VC—maybe he said it another way—“And in 2 years I want to be at 2,000.”

Now, he’s trying to be a rabble-rouser, and he was trying to say, “I fired Zendesk 2 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 spending, and it is terrible for almost every software company.

Maybe Shopify is oversold. Maybe New Relic is oversold. But overall, even for Mike Cannon-Brookes, it’s not great for Atlassian. If we’re all going to shrink our teams from 6,000 to 2,000, it certainly isn’t great for them. And maybe HubSpot, Monday, and all these people are thinking, “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 in this. It’s not valuations, right? It’s hard for me to feel 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 3 months—and we're going to get them all seats to software. I just did. Nobody I talked to has that feeling today. Nobody wants to do that.

Rory O'Driscoll

I broadly agree on the sentiment, but I disagree with the statement that there is a bottom. In the end, price clears all markets, right? What happened with these public SaaS stocks is that you've gone from, as I said, the presumption of success, which is what AI now enjoys, to the presumption of failure, right?

That doesn't mean they fail, but it simply means that you look at them cold-eyed and 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 12% to 15% return a year, right?

Yeah, markets work.

Rory O'Driscoll

The other side will overshoot. This will be doable, but it's just not a number you like.

But here's the thing. 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 have fallen to almost 10% annualized growth.

Now, if AI 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 dead bodies don't fall. You can't get to 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've got a little SaaS, got a little older. We've slowed down. We're in the senior marathon, but things are still good at 20% growth.” At 6% growth, I don't see any future other than the next 5 years of free cash flow.

Rory O’Driscoll

I think it's a valid worry, because if things were bad before AI—let's be honest, they had already fallen into the mid-to-low teens before the AI revolution. It's not like SaaS was healthy. Public SaaS companies 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.

4. Wall Street's New Religion: AI Replaces Headcount

The overall blended growth rate is also part of it, because, as we made the point with Mike last week, we haven't put new names in. When we drop Anthropic, Databricks, and OpenAI into the basket, it's all going to look great. If we allow them to remain in a pure basket, it's going to look great, but the existing group is not looking healthy. It's not.

If we look at a G2, a Monday, and Asana, these businesses are all doing okay to decent, actually, but the price is through the floor. We keep on saying, “Oh my God, it can't go lower,” and it does. I genuinely want to know what happens.

Rory O’Driscoll

Well, look, I think the markets—you know, it's just the old cliché: in the short term, it's a voting machine; in the long term, it's a weighing machine. We're going through the voting stage now, right?

My big aha is—and as you mentioned earlier, I was thinking a lot about the SaaS apocalypse—today I kill SaaS. I think what really happened is Wall Street fell in love with AI, and it promptly fell out of love with it, and then it had to fall out of love with SaaS, right? The burden of proof is the other way, right? But you've got a shake-up between them.

If you take something like Shopify, I'm going to say it: I don't think there is a credible new end state that replaces a shopping website for shopping and a payments mechanism, which is 60% to 70% of the business, with some kind of AI hand-wave in the way that there is for many of the workflow automation software companies. I'm just picking on Shopify, for example, in a positive fashion. I'm super positive on Shopify.

5. The Bear Case for Shopify: What Could Go Wrong?

Exactly. Super positive, right? But it is in the basket. It is cousins with the rest, right? It is probably oversold, we could argue. If we are running a long-short hedge fund, maybe we put 5% of the fund into Shopify, right? It would make sense.

Even though, 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, that 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'm shopping on ChatGPT, I may never go to that merchant's store. In the short term, it doesn't hurt Shopify because it is the plumbing of the store, right? 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.

Tobi Lütke says the same thing. That's why he's done more code commits in the last 60 days than in the rest of his history. The Shopify software—even if it's only 25% of the revenue today—in 2 years, that software may be obsolete. If Tobi thinks it, and this is the most resilient AI, and Tobi thinks it, what hope is there for mere mortals?

Rory O’Driscoll

But that assumes the UI of the future is conversational commerce. It is the UI of today, Harry. If you're deep in e-commerce, you can talk to anyone.

Because it's the UI of today because it's what the most productive people in the world find the most optimal UI, which is Sam, Elon, and Dario.

Rory O’Driscoll

Actually, when you look at consumers, most often they like browser-based UIs. They like discovery. They like an option set.

I agree. Again, don't overstate. Look, I definitely think chat is wonderful for research, which is why, despite your opposition in the past, I've loved the G2 marketplace. I think chat is the place you go for a considered purchase and for doing research on whatever you're buying, right? But then you go to the store and look at the thing. I don't think we're a long way from, “I'll just press the magic button on ChatGPT and have it come.”

Rory O’Driscoll

No, but it might not be on Shopify's website. It might be on an AI agentic front end. 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 in Shopify.

Everything's at risk to AI, I believe. Every platform that is open is at risk of an agent being better than the native platform. Every platform that is closed is at risk of being at least slightly bypassed.

That's the risk. I haven't logged into Salesforce in 6 months, but we use it every minute. Our agents use it every minute. I think it would be disingenuous to say that couldn't happen to Shopify. Agentic commerce—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 sure whether the size of the threat is as large as it is to others, probably not, but it's not to be dismissed given the incredible pace of progress we're making. I can't keep up. I'm struggling to keep up.

What I don't like about this discussion, and what makes it hard, is that it's really hard to disprove a negative, right? Actually, one of the most insightful things I saw about this SaaS discussion in the last couple of weeks was that 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—and I'm going to repeat it again—in the short term, we're narrative and momentum creatures, and all that's happened now is that the narrative and momentum have shifted to “AI's going to do everything.” So the people who are left trying to prove that that's not the case are left, as you say, trying to—you can always articulate a scenario, right? The question is, on a balance-of-probability basis, is that going to happen?

Rory O’Driscoll

Well, right now, the thing is, smart traders don't fight the tape, right? Right now, in the short term, the momentum is all around this narrative that AI replaces everything, right? 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 or 30 years. At the end of 20 or 30 years, it accounts for 4% of 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, right? 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 point, the momentum trade will dissipate and people will go, “Ooh, this is really amazing, but it's just not quite the universal everything.” That's the point at which you'll see a correction, but until then, narrative dominates valuation in the short term. Nothing you can do.

That's right. I just had one thought as investors, right? The poor public SaaS CEO who, as I say, is trying to prove a negative: “Let me prove to you why I'm fine.” It's just too hard.

Rory O’Driscoll

Just one thing. The tough thing as an investor is that you do also have this lab. It's called your portfolio.

Yes.

Rory O’Driscoll

One thing you could say today is, “Hey, my early-stage companies aren't truly at scale. Scale is north of $500 million or $1 billion in revenue, so they don't matter.” But on the other hand, you may be seeing the future in your portfolio.

Jason Lemkin

And public SaaS, when I look at my last fund, right? I see what’s happening, and the fund’s in good shape—whatever, 4.5x. But honestly, 2 companies are massively benefiting from the current world in B2B. Massively benefiting and accelerating. One, I would say, is a push: it’s benefiting north of 9 figures of revenue, but also being hurt.

And everything else is struggling because of AI—all the rest of that last fund. It’s not all growing at zero; I’m not saying that. But, man, it was so similar in 2023. So, is that the past or the future? I get confused, 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 companies.

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. I think that’s correct. 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.

I think that, on the other hand, is probably true. And so, I just want one comment on definitions. Everyone says SaaS is dead, and it’s such a useless word because we have to define our terms 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 Claude is SaaS, Harvey is SaaS, and Salesforce is SaaS, right?

So, when people say SaaS is dead, there are kind of 2 separate threads here. Within the new world of AI, are we talking about how much the model will get versus the next kind of—I call them new-school SaaS—like the Harveys of this world, the next-generation companies that are pejoratively called wrappers and optimistically are called standalone companies that can leverage on top of ChatGPT?

Then, separate from that, there’s old-school SaaS. I think what people are—most of the time, people are saying old-school SaaS. In other words, stuff that was built pre-2022, pre-GPT, is what we’re really talking about here, right? Most of the time. Then sometimes people go all the way to, you know, all software’s dead and the model’s going to eat everything. First of all, you have to just distinguish between those 2 scenarios, right? What you’re talking about, Jason, and I agree, is, for lack of a better word, old-school SaaS built pre-2022, right?

And what you’re saying, which I think is also true, is that if you’re public already, you’re now living in a lower-growth world. If you’re one of those companies—Salesforce, ServiceNow—you’ve 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-Brookes said last week, the good news is you have 5 years of 30% free cash flow, and the bad news is, in year 6, your revenue goes to zero, right? So, you’ve got to do the 2: be financially disciplined while adding AI to grow it, right? And I think that’s again kind of what’s going to distinguish public versus private. That’s the public SaaS company movie, right?

Anyway, then the last—the tough category—is the small private pre-2022. If you’re not getting AI lift, you really have to worry about what you’re doing, right? Especially if there was a credible SaaS story in your space. I do believe, again, just to say it, there’s a lot of markets, even pre-2022, that are software plus payments, software plus services, that aren’t all AI. It’s not a baby-bathwater thing. But definitely the sweet spot of your argument is horizontal workflow-related software built pre-2022 that’s not public with critical mass. That’s probably the hardest place to be.

I just see a realization in my portfolio now of companies that are in the $8 million to $20 million ARR range, not benefiting massively but growing 80% to 100%, that are basically like, “Okay, we’ve 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. Yeah, that’s what we said. Is Figma a baby getting thrown out with the bathwater?

6. Replit & Lovable are Proof Figma Missed Out: Figma; Buy or Sell?

Jason Lemkin

Bull case on Figma: you can’t argue—here’s the existential problem with public companies—you can’t argue with the current numbers, right? You can’t argue with the current growth north of $1 billion; it’s great, right? The other thing you can say is, okay, let’s go back to your favorite Lovable-Replit number-one use case for both: product teams building prototypes, okay? Anton said this last week. Number-one use case at scale, not when Harry invests. Number-one use case, I’d say, for both, okay?

That is all the 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: they thought this was revolutionary, but that is $300 million to $400 million of ARR Figma should own. They should own this. Lovable and Replit 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 ties into all of this. Figma can’t argue with Figma today. That checks every single box on growth, market share, everything. But, good God, they missed $300 million to $400 million of growth in their core from AI? I’d be pretty critical, right?

It’s actually double that. Both Lovable and Replit are $350 million independently.

Jason Lemkin

Yeah, but not all of it is product. It’s just the number-one use case for their enterprise. I’m just guessing that, 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, I’m 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, okay? Figma should have owned this. This is just the bear case, right? And my God, now we’re in 2026. The earnings will come out, I think, before this pod comes out, but why isn’t Make a $300 million, $400 million, $500 million ARR business?

This is much easier to sell than these damn seat licenses, where we have to bang our heads against the desk to get $20 or $50 for Figma. I can just sell multimillion-dollar deals of Lovable and Replit just because my product guys can now ship functional prototypes. They missed this huge change. Base44 has also absolutely crushed within Wix, and its growth is very

I think you’re exactly right. It’s brutal. First of all, I think you are correct. So, let’s do Figma first and then the other companies. And I think, back to the valuation, I think the valuation is perched between—if you had another $200 million to $300 million of ARR revenue growth, where it would be north of, you know, 100% to 120%—you would probably be valued at 20 times revenues, 25 times revenues, right?

If you don’t get on top of this soon, that 10x revenues is going to go down to 5 and 4, and you’ll wonder where the other 70% growth is at. So, markets are doing their job. There’s probably an embedded probability that they make a better product and take more share here, and some of them really are not, right? And it’s kind of in the middle.

And you’re right: fast-forward 5 years, there are really only 1 or 2 stories. They get on top of this, they get a third of the market share, valuation continues to grow, and they’re fine. If they don’t get on top of it, you trend down to the horrible multiples, right? But I do believe—and again, this is back to the fact that not everything will roll over in 1 day—that, ironically, even though Figma, I think, is one of the most exciting companies of the last 5–10 years, that space was very vulnerable to this disruption because it turned out to be very AI-adjacent, right?

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. 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, right? For example, I don’t believe—accounting—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 just debits and credits and a good UI. How adjacent is Canva to AI? Probably pretty close, too. Anything that’s creative—individual coding and individual creativity—strikes me as extraordinarily close to AI because it’s happening right now.

Canva—I mean, I’ll say it—even Salesforce. We talk a lot about Salesforce and, Jason, I hear you on your agent, 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, coding, or customer support. Now, that’s not to say it won’t. I love what you’re doing with your agent, but just being objective about where the eating is happening fast, where it may be happening slowly, and maybe where it hasn’t happened at all, right?

Jason Lemkin

Yeah, but of course you’re right. I’m an investor in a company called Monaco that Harry knows. It’s the next AI SDR for us. We already have 4, and they launched last week; we went live last week at the same time.

A couple of things are interesting. First of all, from a technology standpoint, it booked us a 6-figure deal on the first day. None of our other agents could do that. It booked a 6-figure deal on its own.

Now, that is interesting because that is the pace of progress. Our other products—we had Agentforce, Artisan, Qualified, and a few others—they’re all great. We use them every day. They couldn’t book a deal on their own the first day. So, the rate of progress is accelerating like we couldn’t believe. It did it on its first day.

And then here’s the second point: they have every demo booked up through the summer. If they had enough manpower, they could do $2 million to $3 million in their first month because the demand is so strong.

There’s fragility, there’s turnover. We could talk about how prompts are portable, and the fact that this is so good that we’d throw out an agent we bought a couple of 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, these sales tools may not be safe.

There was just a torrent of demand in 1 week, and I see it in all of these products. It is inexorable, and it just gets me: this one is better than the one from 2 months ago, which is better than the other one. We will switch to the next one if—iteration after iteration—and now you’re starting to see, with the reasoning models, increased performance.

As you say, they’re starting 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 the sales stack.

But my point is just compare it, for example, with, as you said, to take one of your other 2 examples, coding. There’s a $2.5 billion market already taking place. There wasn’t a $2.5 billion market. Not all the markets are moving at the same speed.

If you take, again, your Canva example—I'm sorry, my brain—Figma, right? The next-generation product tools like Lovable and Replit are doing $300 million, $400 million in the space. My point is merely that the pace of adoption is not consistent across the board. There’s a sequencing question here.

Jason Lemkin

For sure. We could spend our whole time on this. But at a meta level, in some ways I don’t think it matters because there’ll be spaces that are destroyed, and there’ll be spaces that are maimed. I don’t know that it matters on a terminal basis.

If your space is going to be killed in 8 years versus 8 months, if you’ve gone on to hospice care, does it really matter how long you stay in hospice? To the kid, to their employees, and to the family, it does, but everybody pretty much knows when that SaaS company goes into hospice, it ain’t coming out.

It depends on how long it’s going to be.

Jason Lemkin

Yeah, I mean, there’s a period of time in which you probably haven’t got time to adapt, and then the longer you have—

Yeah, the more chance you have to adapt. Again, as I say, it’s utterly boring trying to predict. You will play the game and find out, right? I don’t know if everything gets rolled over in 2 years. I think—look, give an example.

Jason Lemkin

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.

This is why I feel anxious about everything, but I don’t have to do this. Figma IPO’d in July 2025, right when we got this podcast going, right? Freaking rocket ship. Actually, at the margin, it seems to be benefiting from AI, at the margin, right?

Just since July, Replit and Lovable have taken $300 million, $400 million of their market, and maybe even since September or October, because the product didn’t even really work until September or 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 has stolen it.

Yes, the product is 1 derivation away from coding, so no argument. But let’s not view any islands of stability when, in July, this was the best thing we’d ever seen.

But on the other hand, now that the SaaS—again, the question is the velocity at which it happens. I was just thinking about the SaaS change, and we both started investing in and looking at this stuff in the early 2000s, right?

Salesforce went public in 2004, and ServiceTitan, which is also a SaaS company, went public in 2024. So, it took around 20 years for the whole thing to transition, right? I don’t think it’ll be that slow here, right? But I also don’t think it’ll be 2 years, right?

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 adopt quickly and which markets are going to take more time.

For example, 2 of the most interesting app categories—other than coding and customer support, which we’ve talked about—have been the entire legal 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, right? It was much more greenfield than some of these places where you are competing against existing SaaS companies.

It’s worth pointing out that the sweet spots of adoption have this kind of jagged-edge idea. It’s not all happening uniformly. Some places it’s happening now, and those have been amazing categories.

Jason Lemkin

For categories that, frankly, weren’t great in SaaS land, legal was a miserable category in SaaS land. It’s been amazing in AI land because LLMs manipulate language, and lawyers manipulate language, too. However you want to interpret “manipulate,” right?

Whereas some of the other, more structured apps, it’s been a lot slower. Well, you know what? Maybe, just to wrap up the point here, it is an interesting investing question, right? Because we started this on Anthropic.

You could have 2 strategies to investing in AI and software. One is, let’s invest in massive disruption today. That’s Anthropic. That’s most of the 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.

That way, there’s a little bit of extra time. Some folks may be missing it.

Rory O’Driscoll

It’s not that it’s not coming. It’s going to be as disruptive as Anthropic and the rest. It’s just I’ve got 2, 3, 4 years instead of 2 weeks. Right?

It doesn’t work unless you can do lifecycle funding as well. Because with the opportunity cost of cash, you have the concentration going in a certain direction. If you take the second route, the contrarian approach, you have to lifecycle-fund that until it becomes attractive.

Rory O’Driscoll

Just slower.

Yeah, it has to be more efficient, for sure, right? You can’t raise 4 rounds a year in that approach, right? Not for a while. Which is why I think that the best place to be is neither of those 2 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 about Time. I think I’ve said this before here. He said, “My job, when I’m the publisher of Time magazine, is to be 6 months ahead of the American public. Not 2 years, not a week, right?” And it’s the same thing here.

Rory O’Driscoll

I mean, fair credit to the smart folks who looked at Anthropic in May of ’23 at Spark Capital and Menlo Ventures and said, “Hey, this is the trend that’s going to be.” And then you get the momentum, right? You don’t want to be looking at something that’s not going to happen for 5 years, because I’m with Harry, right?

The trick is to have— That’s why I’m saying, try 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, it’s going to be a key part on the app side of picking where to play.

You also said about customers willing AI into existence. What I see in law—and I don’t know if you do, too, Rory—is just big law firms willing AI into existence in a way that they never did in a SaaS era, where your Justin Kanes and your Atriums were coming with products. They were not willed in with the same persistence that these customer bases are today.

Rory O’Driscoll

I agree. You’re exactly right. I remember, because we have invested in AI companies for 20 years. I remember for a long time there were deals where you’d go, “You don’t want to emphasize the AI, because the customer would get scared. They wouldn’t like it. It would slow down the sales cycle.” Pre-2022.

And what’s happened—and Jason said it earlier—the big aha here is post-2022, 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 everyone’s going to have an AI strategy. Therefore, they’re going to spend money.

I mean, if you were Harry, if you were running an American Am Law 100 or whatever it is, right? You’re not going to sit down and say, “I’m not going to make a play because I don’t think it’s all going to work, right?” You’re going to make damn sure that you do something. And therefore, 500 companies went— All of them went, “I need to spend $1 million right now.”

Dating a lawyer, I see this every day. They are competing on price just like us as venture investors. If they’re not using AI, they’re 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.

Rory O’Driscoll

Yeah. I mean, it gets back to where we started: 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 Anthropic is working. That’s why some of these other markets are working. It’s picking the markets that just tip.

And, yeah, the journey lasts only 2 or 3 years, and they’ve already made that decision, right? And that’s what’s happening here right now in some of these markets.

7. Stripe Raises at $140BN: Is Stripe Wildly Overvalued or Adyen Undervalued?

You said it about 20 minutes ago, about a narrative chasm or a narrative shift with regard to one of the companies we were talking about. When I think about narrative chasms 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?

Rory O’Driscoll

Actually, no. I went into this thinking, “Oh, I want to find some narrative story,” right? But in fact, there were perfectly rational reasons, with one caveat, why they are where they are.

I mean, for starters, zooming out, Stripe is just raising privately, I think, at $130 billion or something like that. Adyen’s publicly traded. Oh my God, I looked at it this morning; my brain is gone.

$50-ish. It’s less than that now, right? It’s half.

Rory O’Driscoll

So, a couple of things. One is Stripe’s doing $5 billion, plus or minus; Adyen’s doing $2 billion, right? So it’s half the size. So, 2.5 times the size. So instantly, you have to multiply by 2.5, right?

Adyen is very, very profitable, right? But the growth slowed, right? Stripe, it’s not clear it’s profitable, it’s not clear by how much, and it’s not clear what the growth rate is. So they’re a lot closer together than one would think when allowed for size.

So then, on top of that, you have the classic—I mean, it’s a little like the whole South Africa 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.

Basically, instead of saying the Stripe price is wrong and the Adyen price is right or something like that, it’s the eternal venture question: how much extra in revenue multiple do you pay for how many extra points of growth? If Adyen’s growing at 15% or 20%, how much extra revenue multiple do you pay for something going at 25% or 30%? I think those are the contrasting narratives here.

Adyen’s a wildly profitable company. It’s almost 50% operating margins. Growth slowed. This is a company that just wildly miscommunicates—

Yes.

Rory O’Driscoll

—or communicates very little about how much cash they have and how they’re going to use it. And I think, alternatively, Stripe communicates in an incredibly strategic way, 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. Do they even have a podcast at Adyen management? They should give up then. They should give up their $40 or $50 billion.

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. Adyen had 21% year-on-year revenue growth in H2 2025. Would you rather buy Stripe at $130 billion or Adyen at $40 billion or $50 billion?

Rory O’Driscoll

I would go with Adyen, because the likelihood of it being mispriced is lower, either to the downside or to the upside. Right?

Bold, Rory. Yeah, you’re trading on value. I mean, look, you have access to the data. You know it’s wildly profitable. You can value it, right? In 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 to— Again, you have to distinguish— Disclaimer, people: for the Collisons who 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—

Jason Lemkin

I’ll tell you the simple reason I would take Stripe.

Well, but that’s the role of prices: to equilibrate between the other issues.

Rory O’Driscoll

I’ll tell you the simple reason I would take Stripe, and it kind of echoes in my brain from Mike Cannon-Brookes last week, right? It’s just the flexibility and the agility you have today from being private.

In today’s world, it’s so stressful being public. You heard Mike’s point: “I’ve got to be more profitable and massively invest in AI.” I mean, he was great, right? It was such a great one, right? But you could hear that, and he was up for the challenge. To his kudos, he was up for that challenge, but not to have to make that trade-off perfectly and be private—even his sort of cheeky comment that his buddy Cliff didn’t have to deal with it. Maybe he’ll wait to IPO.

I mean, I’d rather be Stripe, and so I’m going to bet on Stripe on this one just because I think you have more flexibility today to respond to change. My prediction is, by the back end of this year, we’ll see the big 3 guys diving for the public line: Anthropic, OpenAI, and SpaceX.

And I don’t think it matters when you’re profitable 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.

Isn’t it a funny time where the public markets are, at the same time, the most attractive place in the world for a company that has the ability to be memed or consumer-loved like never before, but also, at the same time, the single most hellish spot on earth? And it’s both at the same time for 2 very different sets of companies.

Rory O’Driscoll

Yes, it sucks. Now, 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. And the problem with that is that not all companies are like that all the time, which is why the number of public companies continues to decline.

Right? I do think at some point it has to be an easier place to be public while you're dealing with and managing transitions. If the idea is that every time you have to deal with a problem, you have to go private to fix it, that strikes me as a little absurd. It's a combination of lawsuit avoidance, board exposure, indexing, shareholder bases that have little patience, and activists. There's a whole bunch of reasons why it's shitty to be public.

8. OpenAI Buys OpenClaw

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 overall. You mentioned OpenAI there as one of the companies diving for the line. Very big news was, obviously, OpenClaw creator Peter Steinberger joining OpenAI, and 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 Moltbook 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 OpenAI?

Jason Lemkin

Well, look, I don't know. On the one hand, when OpenClaw—or whatever it was called back then, Clawdbot or whatever it was—first came out, I was like, and I said this to one of the top CTOs I work with, "You're going to turn this off," because I was already there last summer when an agent deleted my entire database.

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 labs don't want you to do because they know it's a problem, right? 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 turn this off. It's a dalliance, right? It's a proof of concept."

That's probably still true. You're not seeing amazing applications in the last month that have come out of it. But, 1, it has ignited the developer community like something we have not seen in a long time. Buying into that mojo has some value, right? Buying into one of the fastest-growing stars on GitHub, the fastest-growing repository, and the fact that every cool engineer is playing with it—it may be ephemeral value, but it's real.

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 Manus. So is it worth $100 million to OpenAI? Maybe, if that's what the price is. I don't know what the price is, but $100 million—I think it should be worth $1 billion-plus. I don't buy that it was sold for $1 billion. I don't buy it.

But maybe it's true. You have the numbers; I don't. Do you?

I think it's about $100 million. That would be my guess based on a number of things. Maybe it's more.

Jason Lemkin

Obviously, he probably turned down more from Zuck, right? Which would be the great insult. But I think what it opened everyone's eyes to—and I think this is why Anthropic was so dismissive of it at first—is that the safe thing is, "We don't want semi-autonomous agents running. We don't want agents running rogue 24/7 with no guardrails."

Breaking guardrails, saying crazy things—this is today's AI nightmare. This future AI nightmare is coming, but it's too late. I think it's too late now. Every developer wants to develop truly autonomous agents, and whether this platform will decline if he gets bored and goes on to the next thing or not, I don't know. But the horse has left the stable for these autonomous agents and the risks associated with them.

There's no reason that OpenAI and Anthropic couldn't have built this last year. They just didn't think it was safe, but it's too late now. Just like Elon said 6 months ago, "I wish we could delay AI 3 to 4 years," but since we can't, 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.

The risk has been elevated, but everyone's excited, so the amount of innovation that will come is hard to predict, right? When all of our apps run 24/7, making their own decisions, deciding whether guardrails are appropriate, and working around them—

Jason, what does this do for inference requirements?

Jason Lemkin

In theory, it'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 $4,000 or $6,000 Mac Studios. But we'll figure it out, right?

Listen, there's a limit to my expertise, but you can run 24/7, right? And you can run on mini models, and you can run 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. Maybe you run Haiku 4.5, and you're actually not running it 24/7. You're running it every 20 minutes, right? So you figure out the cost.

Haiku is like 1/20th the cost of Opus 4.6, so it's manageable, especially for apps where there's budget. I don't know. I think we'll figure it out.

Well, agreed. I thought 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? When I went to my IT guy and said that I'm planning to download and try it, he pretty much had a conniption. So obviously, you just have to go and do your own little thing offline.

I agree, it was like, "Wow, this is the agent untrammeled, with no controls over what it can do on your desktop." I don't think that's 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, to get the positives of it without 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. 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 6 or 8 agents that would go off and do things at the same time the human spawns them. I'm sure it's true in level 2.

I know in the next release of Replit, not only does it happen because they've built their own set of guardrails, but the agents do it at night. In the next release of Replit, when you log in the next day, it will have built 3 to 4 features for you on its own. That's coming in the next release, in v4 of Replit.

Imagine that happens to every app, where you go to bed and wake up in the morning and it's done all your general ledger. It's done all of your—whatever. Maybe it'll be slower to account for this and that, but it will have built all of your assets. It will have rebuilt your entire website. That might be a threat to Canva.

When you go to bed and wake up in the morning, it's built 4 versions of your website. I mean, I know, and I'm not saying others won't do it. I'm saying Vercel as well, but I know this is in the next release of Replit. That's pretty disruptive.

OpenClaw 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 is coming in 2026, and part of it is pretty scary. In one sense, anyone could have done it, but maybe in the big labs they said you shouldn't, and this guy just put it out there and everyone went—

Jason Lemkin

Yeah, 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." Because when both OpenClaw and Moltbook immediately published everyone's private keys and private passwords, they're like, "This is exactly why we have a safety team. We're going to sue you if you use our name. This is terrible."

But then every single developer thought, "This is it—off to the Apple Store, or worst-case, Best Buy." They're buying Mac minis and Mac Studios because no one was more excited to spend nights and weekends building these things.

That's why folks are like, "Anthropic fumbled this." Maybe it's just that they thought this was the wrong thing to do—completely unsafe. Zuck and Sam Altman had another month and a half to think on it and said, "This is a movement. This is a freaking movement in AI."

Do you think Anthropic fumbled the bag by not investing in this? By not trying to buy it?

Jason Lemkin

I think the world changed. This went from something that was a seemingly goofy guy with a shit-eating grin on his face who could bench-press 400 pounds—it seemed like a goofball guy almost mocking us—with your legal team saying it's unsafe, and Dario saying, "It's about safety. We don't want this on our platform," to being, like, utterly the coolest thing that's been built in 6 or 8 weeks.

I just think that everything changed. It's just like investing. I don't think they fumbled it. 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, instead of the cease-and-desist, just chill for another couple of weeks. Maybe that was the error. But I think it was too early to know it would be a movement.

But if you talk to CTOs in your portfolio, whatever it was, it was only like 2 weeks ago, right? Just all of a sudden, everyone was using this 2 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 they're like, “But look what it can do.”

But it's so cool. But okay, what's the great app that you did?

Jason Lemkin

Well, I built a TikTok, and it sent an email for me last night.

Oh, great. [Laughter]

For what it's worth, I think that's a great take, Jason, because you're right. My initial was, “Oh, my God, Anthropic fumbled.” But you're exactly right. You set yourself up as a safety company. You're extremely careful about what you allow to 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'd been stuck, you know, with a stick, right?

Jason Lemkin

Manus built this in 1 night and said it wasn't about building the technology. You could do it in 1 day, and we just 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. 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 exploit is removing a guardrail you're not supposed to remove. You might get 1 million developers to use that in 2 weeks. See Grok for details.

Yeah. Who is the responsible provider of guardrails, do we think? I don't want to get too deeply into it, but is it the vendor who's offering the agent? Is it the data holder that holds the data—your Salesforce, your ServiceNow, you name it? Or is it an independent third party that sits as a layer between?

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 AI 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 doesn't have. He doesn't have that weight on his shoulders.

And were they, Jason, tech providers or tech users? Were they customers of these agents?

Jason Lemkin

The top chief AI officers at public B2B companies have a lot of weight on their shoulders about responsibility for their own guardrails, which are much narrower than what OpenAI and Anthropic have. I mean, you take the guardrail off OpenAI, and it can shoot a gun. You know, hook a gun up to your LLM, change the outcome of the LLM, and say someone's threatening my home, and it takes it the other way and shoots. It could shoot a person.

Ask your LLM if it could do that. It could say it's possible, right? You have to have the guardrails, especially if you hook it up to the real world. You laugh, but it's not that funny. Take someone that'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 massive.

Leaving gun comments aside, because I think it's a little far-fetched 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 to something like the slightly safer equivalent of OpenClaw, I'm selling a software product to my customers that can exfiltrate all their data. You could make a 24-hour, career-ending, company-ending move here. You're right.

Jason Lemkin

Actually, now that I think about it, those guys are bearing it because, Harry, to your point, there are 2 separate questions. Who's—I mean, you said, who's responsible for this? I actually think it breaks it down: who's going to be fired if they get it wrong, and then what software will there exist to help so they don't get it wrong? Those are separate questions.

My guess is the answer to the former is anyone responsible for initiating these agents. 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.

The interesting question now—I think that's multilayered too, because lots of different people can bring in software, but CISOs, chief security officers, will be blamed also. There's a multipart—

Jason Calacanis

Absolutely. So, my guess is, even as we speak, there are people building really compelling agent-first security products to make darn sure that doesn't happen.

Oh, plenty.

Jason Lemkin

And we are about to invest in one.

Of course you are. Of course you are. That's right. You know what? That's great. But what about me?

Jason Lemkin

Me. Can we change the title of the show to that? I think it's got a nice ring to it.

I like that. It's got a catchy ring to it.

9. Thrive's $10B Growth Fund

Before we do, 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 and the $10 billion, now $9 billion, growth fund. I know it seems less than Andreessen's $15 billion, but actually their growth vehicle is bigger than Andreessen's at $6 billion. My question on Thrive is just: how much bigger do funds get in venture? Are Lightspeed and General Catalyst going to come out with $20 billion?

Rory O'Driscoll

I mean, again, as we've said, thinking of it as early-stage venture is just a mistake. It's this, again: how big should a fund be when companies raise $30 billion rounds?

Now, there are only a few companies that raise those kinds of rounds, but if there are 4 or 5 companies valued at north of $100 billion, a $10 billion fund—which is, you know, the 2 model companies, SpaceX, Stripe, and Databricks. Again, when you're dealing with $100 billion-plus market-cap companies, potentially one of them is as much as $1 trillion, a typical 5% ownership position is $5 billion. It's just math, right? 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.

I mean, I think we said it in one of our shows earlier on, Thrive has done an amazing stock-picking job of backing Stripe, of backing Databricks, of backing OpenAI, and of backing them at scale. The companies need the money. The investors who have money want to get into those companies. Thrive is in the middle saying, “I'll make this happen.” All right?

Yeah. I go back to my comment: in a more sensible world, all these companies would be public, and we wouldn't have to pay all these fees. Someone could buy Fidelity Small Cap Growth and get—actually, in this case, mid-cap and large-cap growth—pay 50 bips, and buy the same stock.

Jason Lemkin

But, in a world where these companies stay private, the need for someone like Thrive with $10 billion is acute, and they've stepped up and filled the need. There's probably room for more.

Plus, it makes it simple when you're Thrive and your model is to do every round, right? 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. If you don't beg off at the $380 billion or the $760 billion round, it actually makes your fund construction much simpler. Get into the winner, and do all of the rounds.

It's a very calming model. The partner meeting's very simple. Anthropic also wants to raise at $800 billion. We can do $3 billion in.

To be fair—

Jason Calacanis

It's just our model. It's our model. We're in. Next, Harry has his AI agent company. I don't know about that one, but—

10. Arif Janmohamed Leaves Lightspeed for New Firm

I'm going to give them credit, though. They actually, specifically—unlike some of the other funds that I've invested in both—they specifically are a fund that said, “No, we backed OpenAI. We're not going to back Anthropic.” So, they at least—I should have said OpenAI is raising the money—they've been monogamous here.

One thing I do think is interesting is that, actually, in the same week, we saw Arif Khan Mohammad, who I'm sure you guys know just through years in the Valley. I've known him 3 years in the Valley. He announced that he was leaving and starting his own thing. We saw Max Gazola of CRV start his own thing, Striker. And I guess 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?

I really respect Arif, and I'm sure you guys do. Leaving in the desire to return to early venture—does that—

Jason Lemkin

I mean, listen, I don't know if it's always about money. Peak XV almost imploded, right? Because the managing partner wanted to keep all the economics, right? Just the other day. It's not about getting back—who wants to get back to early stage? I want to do the Anthropic round.

[Laughter]

Give me a fucking break. I don't want to have to pick which accounting software 4 years from now might break out for AI. No one wants to do that.

Just show me the carry. [laughter] I don't mean that's true, though. I do think there are people who've made a ton of money. I'm sure Arif's made a ton of money. He loves working with founders, and I think he's bored of the bureaucracy of a big firm. He's like, “I want to go back to picking cool founders and having fun.”

Rory O'Driscoll

Yeah. I think there's definitely some of that. I mean, Jason, your cynicism is often warranted and is often over the top. But, yeah, 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, right? Do you really want to be sitting there with 5 other people having an opinion in your deals? At some point, you kind of go, “Maybe I just don't want to do it this way.”

Jason Lemkin

You might if you like them.

Rory O'Driscoll

You might if you like them, but then if you have too many opinions, I find you don't like them. Look, the 2 of you guys are solo GPs, so I can speak to this. But my point is, again, 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 multistage firm, first of all, as a senior lead, a lot of your time is spent on firm-management stuff, that's my guess. And then, on top of that, maybe 90% of the decision-making is about, in Lightspeed's case, do you brilliantly lead the $60 billion pre-round at Anthropic? It's not about, do you put $10 million into this early-stage founder? If that's what you want to do when you've made a gazillion dollars, go do it.

Jason Lemkin

For sure, for sure. There's no question that, if it were me and I was a partner at Lightspeed and I was the same person I am today, I would retire into my own fund, right? Just to not deal with the bureaucracy, right?

There were, Jason. There were well-run firms that get to you first.

Jason Lemkin

Yeah. [laughter]

Jason, I'm not going to say you'd be pushed.

Rory O'Driscoll

But the thing is, maybe they're kind, but walking away—very few firms, I'm sure Scale's different, very few firms in my experience, and Harry has more data than me, are kind with carry vesting when you leave. Very few firms are kind, okay? I mean, Chamath—all his ex-partners have sued him. Mamoon sued him; the Groq CEO sued him. I'm just saying people aren't as kind to carry when you leave.

I'm not saying that Lightspeed might be the opposite. They might be the kindest, and I know some are kinder than I would have expected, but my meta-point is it's not simple to walk away from vested carry. It's not simple. 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 where you literally could just half-check out.

Jason Lemkin

Okay. [snorts] There was a significant economic cost at any point.

Rory O'Driscoll

I mean, look, especially with a successful fund—the more successful the fund, and Lightspeed's having an amazing run, the more the cost is. You're right. Anyone leaving is going to—even if all you're walking away from, even if there's nothing kind of crazy, even if there's no loss of carry, you're still walking away from unvested value, right? That's, again, back to being post-economic. And you've got to start from scratch.

Jason Lemkin

Oh, yeah. It's a lot. 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. Arif 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, starting young was such a competitive advantage. I was lucky. I didn't realize how lucky it is starting so young. Guys, we can choose 1 more topic. Is there 1 more topic that we have to discuss? Netherlands, Highspot, Anduril, Workday. Any that jump out?

You know, I think you've got good stuff. I don't want to overdo the Workday thing, but, man, it is interesting that Aneel had to go back in, like, 8 months, to run Workday. It's a pretty fast boomerang. Why is that the case? Jason makes the point constantly that this is the age for the founder-CEO, and I agree with him 7,896%. You think Aneel wanted to go back as the solo CEO?

Jason Lemkin

Just as much as Daniel wanted to go back to UiPath. I mean, these guys were chilling. [laughter]

But he couldn't even make it a year, right? And so it goes to Rory's earlier point. I'm not challenging you, but your point is that some software 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. He had to come back.

Jason Lemkin

Fair pushback. What it says—because what I do agree is that, again, look, Carl Eschenbach, a well-regarded top executive, but what you're saying here may be a combination of what the problem is not: go-to-market. What the core problem is product roadmap, and typically that's where a founder can do really well. So 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 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 and think about that a little more.

You know what? It'll be interesting to see. Is it product-roadmap anxiety? Is it identity-crisis anxiety, or is it something specific? It would be interesting to see what changes in 12 months, and that's probably how you judge this thing. 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—I mean, listen, 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 Marc is driving massive change. Now, we'll see whether it's successful, right? But he's driving more change in the last 8 months than in the decade before that, and who but a founder could drive that level of stress and anxiety and change across the company? Everyone thinks they've got to step it up, right? And it's just, as an outside CEO hanging out at the SKO in Cancun, it's hard to drive that change.

I think you're right. I mean, it's funny, and I was thinking about this because I normally try and be contrarian. One of the things I try and say is, “Is that really true? Can it just be the founder?” You love founders, you back founders, but you also want to try and not overdramatize or overattribute uniqueness to founders, because at scale companies, they all have to be run by non-founders.

But I've decided in this case you're right, because the thing is, if you have to do a turnaround with a problem or a business challenge, I can totally see a hired executive saying, “We've got a cost problem, we've got a go-to-market problem, we've got a segmentation problem.” All those things are classic playbooks, and someone will—there's lots of work to get done.

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 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 2 years to even figure it out. I just know. Can we do it this way?”

So I'm coming around. In this case, I think you are right, Jason. 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 is.

Do you think it will work bringing Aneel back? The board is clearly trying to increase the share price over the long term. Do you think Aneel will be able to increase the share price significantly in that 12-to-24-month period?

Jason Lemkin

I don't have a developed opinion, because I think that, again, it's back to the—I don't know if there's a magic—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, right? It's not even like the Figma example, where you say there was an adjacency thing 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 have 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 changes, that add up to a better growth rate. I don't know. I don't have enough of an opinion to say.

I think at least he'll drive faster change and he'll make quicker bets. Whether he's the Jobs coming back to Apple or Schultz coming back to Starbucks, we don't know. I think a lot of these bets won't work. But I'd rather have him running Workday or Daniel running UiPath when massive change is needed, because here's the thing: the amount of resistance to change is so high in the employee base.

This is the thing. It’s not just that the founder can make these 2-year decisions in 2 weeks, to Rory’s point. It’s not just Michael Cannon-Brookes’s point that he can make 5-year decisions and today’s decisions at the same time, which an outside CEO struggles with, right? Because if he makes 5-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’ve got to go talk to the regular VPs at these tech companies. None of them want to do the work. The amount of resistance is just so hard to overcome when most of your employees do not want to do what it takes to change.

You can say that’s not true, Rory, but I talk to senior executives at these companies all the time. Everyone wants to do the same job they did in 2023. This is human nature. They all want to do it. The smart folks are actually quitting all these companies and going to hot AI 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 2022/2023 toolkit works perfectly well at the hottest AI companies. It really does. It really does.

We released a show with the head of sales at ElevenLabs.

Rory O’Driscoll

It was good.

It was an insanely popular show. I mean, I can’t even tell you how insanely popular it was. The thing that everyone else related to was the 20x sales compensation. If you want to succeed at ElevenLabs on the sales team, you have a 20x quota on your head. If you don’t hit it, you’re out.

Jason Lemkin

Yeah, but I was with another AI leader where the sales team had $4 million quotas. That’s not that different from ElevenLabs; that’s basically ElevenLabs’ math. They just rolled out their 2026 plan, and it’s a $4 million quota.

I saw the commentary on that, and someone said, “That doesn’t mean you’re hiring 4x-better salespeople at ElevenLabs.” It’s that when people want to buy your shit, it’s easy to sell it, right? It gets back to the same thing: it’s all about momentum in the short term.

Customers have woken up and said, “These are the 2 or 3 things we want to buy in 2025 and 2026.” If you win those things, you can sell, you can grow like crazy, and your stock price can go up. If you’re not, it’s damn hard.

It’s just the constant reminder: keep it simple. Invest in companies that are in markets that are exploding right now. End of complex analysis.

11. Which Founder Returns Next: HubSpot, Twilio, Gitlab?

I agree. Final one, and it’s a bet.

Jason Lemkin

Okay.

Okay. Oh, yeah, don’t worry, Rory, it’s going to be great, okay? Which public-company founder will return to the CEO seat they left next?

Jason Lemkin

I’d say it ain’t going to be Dustin Moskovitz, man. He just left the keys on the table.

“I quit. This job is stressful. I don’t like people. I quit.”

Jason Lemkin

Dude, with an unprofitable holding like he has, I totally don’t blame him. Peace out.

All right, Halligan—sorry, Rory, you can recuse yourself from this conversation.

Rory O’Driscoll

I mean, we’re long since out of that. You’re looking at a $12.5 billion market cap for HubSpot, down 45% in the last 6 months. Halligan is sitting there. I love Brian. He’s amazing. We all do. Amazing.

HubSpot and GitLab are the only candidates I can think of where there just aren’t enough boomerang people. I don’t think Brian’s going back, and Sid Sijbrandij seems to be off on his own initiatives. But I can’t think of anyone else. Maybe I’m missing someone, but there just aren’t enough candidates. There are too many Michael Cannon-Brookeses out there for this; there aren’t enough candidates.

That’s actually exactly right. Another candidate—nothing will happen, but he was a great guest—is Jeff Lawson, who was at Twilio. He’s now like, “I’m doing fusion. You people knock yourselves out with your telecom stuff.”

Rory O’Driscoll

He could have been one if the ball had bounced another way, but he ain’t likely to go back, right?

Jason Lemkin

And given that the activists were mean to him, why would he bother? It’s the same thing: why would I flog my way through that one when I could be—

You’d get over it. I mean, Jeff was very direct. It was a great show, really a great show—greater than people realized, right?

My limited experience is that when you’re treated terribly as a CEO, as Jeff was, if people come back with humble pie and you care, you get over it. You’ve got to pay the price. They might have to have given him a half-billion-dollar package, but if there’s a little humble pie, you get over it, right? Especially if the activists are gone, you get over it.

Rory O’Driscoll

Yeah, not enough sample set, Harry, so we’re ruling the question out of order. The more interesting one, which I would not touch, is: who’s going to quit next?

Ooh. Good question. Who’s going to quit next, Jason?

Jason Lemkin

I don’t know, man. You might surprise us. There are prizes for persistence and resilience. I love Drew from Dropbox and Aaron from Box: just unwavering, resilient, persistent. It’s tough. Credit.

Rory O’Driscoll

No, as you know, I was on Aaron’s board for many years. I just admire those guys for grinding it out because it’s so hard. Especially now, when blabbermouths like us on podcasts are saying, “Nothing you do matters,” you just don’t care. The ability to keep grinding on is actually very impressive. It really is.

We don’t know. You know who just retired? Dave Girouard, right? He said he was 60; he’s retired, right? So there is a wall at 60. I barely know him, but he’s pretty young, right? Externally, there’s a wall of life where it might happen.

For some reason, I was just looking at Yelp this week. Yelp’s down to a $1.2 billion valuation. Jeremy Stoppelman is young, but it’s been 20-something years, right? It’s down 47% this year to just over $1 billion. He’s great, right? But people like that might be vulnerable to personal issues or other things.

At some point, it creeps into the hundreds of millions, and it’s just like, good luck. As long as the founder wants to keep doing it, go team. I just admire the grind.

12. Is Monday.com a Screaming Buy?

Monday at $3.8 billion—is that a buy or not?

Jason Lemkin

Again, the thing is, how can I make a comment here? Let me tell you why I’m going to answer it very quickly.

Well, I’m going to give you some detail because I know what you’re going to say.

Jason Lemkin

No, before you do, you have to give me the interesting comment, which is this: you can’t answer a narrow range of stocks. You can get away with a momentum story, right? You’re right that you could have asked me about picking an AI stock, and I’d say, “Yeah, the market’s big, they’re the leader, buy at any price.” You’re right.

When you’re dealing with something like Monday, you’ve got to look at the revenue, the growth rate, the free cash flow, the SBC, the DCF, and it’s a grind. You’re still playing for a 15% IRR.

All right, we’ve got $1.25 billion in revenue at 27% year-on-year growth. The 2026 guidance expects $1.45 billion. Non-GAAP operating income is $175 million, a 14% operating margin. Would you buy or sell?

Jason Lemkin

What’s the free cash flow?

Non-GAAP operating income was $175 million, with a 14% operating margin.

Jason Lemkin

Yeah, so it’s about right. It’s around 10x, plus or minus. That’s $1.7 billion. What’s the stock position? You said the market cap is $3 billion, and I bet they have $1 billion in cash.

Yeah, it’s $3.5 billion of market cap.

Rory O'Driscoll

This is the classic case. To make the positive argument, if you can manage the SBC—which is a minor but important question—and the major question is whether the growth is durable, 10x cash flow for something growing sustainably at 20% is wildly cheap.

It goes back to Jason’s comment: how durable is that growth rate? 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, for the gradual attenuation of your business, then you have to price the 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, and the age of AI. If you believe it’s durable—which we all did in December—then the fact that the stock’s down 51.3% on the year makes it the greatest buy of the value stocks of the public cloud companies.

If you believe that—and we all believed it was durable just in December.

Jason Lemkin

Has it really? 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 there is. Monday should just load up on Monday.

You have great founders. This is still a founder-led company. You have 2 founders at the top, incredibly driven, incredibly ethical, who know their market cold and who are still selling primarily outside of tech, which has less disruption. How could you not buy this one if you believe the revenue is durable?

You must be saying that none of this revenue is durable anymore. Do you have a durability matrix in your head? I’m just going to do durability of this versus Salesforce. Let’s take Salesforce, because it is the original stuff. Let’s make Salesforce the benchmark of 1. Do you think this is more durable or less durable than Salesforce?

I am long on Salesforce as a platform for agentic agents, for real.

Rory O’Driscoll

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? Durability means it has to organically grow. Durability doesn't count as dial-up at AOL shrinking every year, okay? That's not durable just because we have a 30-year business.

Durable has always meant, for B2B, that 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, right?

I'm going to give us an answer, dude. What's more durable? Is it Monday or Salesforce? Sorry, the question is Monday or Salesforce?

Rory O’Driscoll

I think they're the same. SMBs just 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.

ServiceNow will be the slowest: 99% GRR with 5-year contracts. It'll be the next generation that will really see that decline, right? Five-year contracts, 99% GRR. Monday will churn faster than HubSpot, right? And HubSpot will churn faster than Salesforce. It's just delayed churn. That's the thing: ServiceNow takes you 10 years to get off that platform.

13. Jason and Harry Bet $200,000

So you're oscillating here. A minute ago, you were saying, “Hey, we used to believe it was durable in December; now it's down 50%.”

I wanted to do this for the show. I think 2 weeks ago, I wanted to go and buy $200,000 worth of 4 stocks. Shopify was my top one. I wanted to do 4, and I thought it would just be fun because I'm like, “Look, worst case, it goes down another 20%. I lose $40,000, but I can write off the loss. It's really $20,000 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 Shopify because I just don't see the floor. This is me at my gut. I just want to do it for fun, for the content.

Rory O’Driscoll

Oh, dude, I'll match you. You don't see the floor for Shopify? I did. I was going to buy it right before earnings, and it crushed earnings, and it didn't help. Bummer, isn't it?

Yeah, and I'm like, well. Then I said, “You know what? I want to do this for the show, for the content, but I'll wait until after earnings.” Then it blew out the quarter, and it didn't help. I'm like, “I'll still do the bet,” but I thought it'd be fun.

My honest point is, I was going to do it for the content, and I didn't actually do it. I didn't do it. The worst exposure was $20,000. I'm not saying it's nothing, but it's not as dramatic as it sounds, right? It's not going to go to 0. I'm like, “Why the hell didn't I do it?” It's just because I couldn't see the bottom.

Rory O’Driscoll

But we could do it for next week. We could all do the $200,000. We've got to pick 4 candidates. I'll buy it for next week.

You're going to buy Shopify?

Rory O’Driscoll

No, we've got to buy—you've got to put in $200,000, and we each pick 4 candidates, $50,000 for each, and we watch them for the rest of the year.

No, because this isn't a startup. You're not going to lose $200,000. Rory's going to agree. You're not going to lose $200,000, right?

Rory O’Driscoll

Yeah, it's not as big a risk as it sounds. So we've got to pick 4 by next week. I'm going to put Shopify at the top of my list again. I'll do it. Let's do this. We're going to announce which 4 we're choosing next week.

I need 2 weeks. I'm traveling, guys. Sorry, I need to think.

You don't have to. I'm not trying to force you.

Rory O’Driscoll

Harry and I are going to do it. We've got to show the receipts. It's $50,000 into each—this is not the end of the world. Pick your 4 public companies, and we'll watch them ride. We'll see what happens.

Okay, I need a Salesloft. What the hell? I'm just throwing around $200,000 just for content shares.

I think the competition's gone up. Everyone's got a podcast. What the hell?

Rory O’Driscoll

I think you're right, though. It does force that discussion of what do you really believe? Because it is telling that you went to write the check and just couldn't—

It is. I just thought it'd be fun to come on the show this, I guess, last week and say, you know, I missed it, but Shopify can't do any worse, right? And I just didn't do it. I don't know why. I just didn't do it.

Rory O’Driscoll

It'll be fun. All right, 2 weeks. At least Harry and I got a real 2 weeks. You pick your 4. Take your time.