20VC：Opendoor CEO 谈科技史上最伟大的翻盘｜OpenAI 与 Oracle：双方怎么负担得起这件事｜Anthropic 如何一夜之间失去50%的收入｜Replit 以30亿美元估值融资｜Figure、Gemini 与 VIA IPO 全拆解

Opendoor is priced in the public market for its potential, and it's an incredibly fair price for that potential. Look, I think the bull case for Opendoor is obscene. Just obscene.

Yeah.

It's hard to exaggerate how big this company can be. I'm no one's idea of a professional manager. We're going to create alpha. I think corporate executives should basically only get paid in options. We're going to launch things that won't work, but we're going to start launching things.

This is 20VC with me, Harry Stebbings. It is my favorite show of the week. Jason Lemkin, Rory O'Driscoll, and we have the hottest CEO in town, Opendoor's new CEO, Cas, who just joined from Shopify. He joins for his first ever interview as CEO of Opendoor. He did this show when he was just 24 hours into the seat. On top of that, we talk about OpenAI's relationship with Microsoft, their new deal with Oracle. We talk about the IPOs that happened last week, the busiest week of IPOs this year, and so much more. But before we dive into the show today, let's talk about agents, specifically Piper, the AI SDR agent brought to you by Qualified. The agentic marketing era has arrived, and if you're a B2B marketing leader looking to scale a pipeline generation, Piper, the AI SDR agent, wow, it is here to help. Piper is the number one AI SDR agent on the market, according to G2, and hundreds of companies like Box, Asana, and Brex have hired Piper to autonomously grow inbound pipeline. Fucking sign me up. Anyway, Qualified customers see massive business impact with Piper. 3X increase in meetings booked and 2X increase in pipeline. Wow, that is some results. Hire Piper, the number one AI SDR agent, and grow your pipeline today. Learn more at qualified.com/20vc. That's qualified.com/20vc, with the 20VC spelt out in letters, for goodness sake. And while Piper builds your pipeline, HubSpot gives your business the AI tools to scale faster. Think about listening to this podcast right now. You're probably multitasking and catching 70, maybe 80% of it. How dare you? This voice is so captivating. Now, flip that and imagine catching only 20%. That'd be pretty crazy, right? Yet most businesses only use 20% of their data. All the important details in call logs, in emails, in chats, they're just left floating in digital space. Well, HubSpot gives you access to those insights to help you grow your business, because when you know more, you grow more. Visit hubspot.com to get the full picture today. HubSpot keeps your CRM humming, and when you layer in AI, Nexus takes it to a whole new level. Who's the biggest AI threat to your business? It might be your own employees. They use unsanctioned AI tools and personal accounts for work tasks and feed company data to places, honestly, it just shouldn't go. Well, this is what we call shadow AI, and it could cost you millions. IBM found that 97% of organizations reported an AI security breach that's in 2025 alone. As a CTO, a CIO, or a head of AI, that's a mistake you just can't afford. Nexus.ai fixes it with an all-in-one secure AI platform. Nexus.ai stops shadow AI in its tracks, so it's a unified platform for secure company-wide AI adoption and productivity. Tech leaders set policies and oversee usage. Business teams get the models they actually need. Try it yourself with a 14-day free trial at nexus.ai/20vc. Guys, I am so excited for this. You all know it's my favorite time of the week. My mother even loves these shows now, which I think is incredibly heartwarming 'cause, um, she listens to every one. But we're gonna start on news item number one. Kaz, from COO of Shopify to now CEO at Opendoor. First, thank you so much for joining for this first little stint.

Thanks for having me. I appreciate it, man.

I wanted to start with the question: You left a great and huge business in Shopify. You must have the ultimate conviction that iBuying is a good business. Can I be so blunt as to ask what led to that conviction when it's been a challenged conviction to have over the last few years?

1. The Opendoor Conviction

I never thought I would leave Shopify. I thought it was going to be my job forever, and I just genuinely loved the company, loved Tobi, loved what it stands for.

When I joined Shopify, everyone was like, “What the hell are you doing? This is a tiny company that's going to go nowhere.” It was among the most shorted stocks in the tech market. It was very much, “This thing will fail.” In fact, Citron wrote a short report the day I joined Shopify about how terrible a business it was and how it wouldn't last 2 years.

But I think Shopify's a wonderful company. The fundamental problem that Opendoor will solve is an incredibly important problem, not just as a business, but for the world. If we can make buying, selling, and owning a home easier, less frictionful, and less terrible, the world will be a better place.

We will figure out how to make money along the way. This will be a great business. We will make money. But the problem space is a valuable one to explore, and I think you need to do it unapologetically. The goal here isn't to minimize risk. We have a mission to go after, and we'll go after it incredibly aggressively.

We're going to make it easier for both people who are buying and selling homes to engage in that transaction because it matters to the future of our society.

Can I be so bold and ask: Does that not feel like a bit of a boom-time mindset? “Oh, it's a valuable problem, and we'll figure out how to make money along the way.”

Fuck no. No, definitely not. Look, this is not—I'm not saying we're going to figure out how to make money along the way. We will make money. That's not what I'm saying.

We will have plans to make money, and we have a couple of good bets already. We'll launch more of them. I'm not saying I have a hope and a dream of profitability. This is a for-profit company. It's very much a for-profit company. We'll figure it out.

But what I'm saying is that businesses should not exist to make money. Businesses should make money to deliver on a mission, and those are important things. We are a mission-driven company, and we'll make a profit such that we can deliver on our mission.

The shareholders will be happy, buyers will be happy, and sellers will be happy, but that's the goal. I'm not saying, “Oh, I don't know how to make money.” I know how to make money here. What I'm saying is the mission is more important than the money.

As a wildly successful software executive, how do you deal with this meme-stock element to the company? I'm not a meme-stock guy. I don't trade.

Yeah.

I'm long in everything. This isn't GameStop, but it's crazy. This meme-stock-ish niche before you is crazy, isn't it?

I'm not a trader. I own literally one ticker. When I was at Shopify, it was Shopify. I expect I will own 2 tickers for the next little while.

Wow.

Shopify and Opendoor. I'm not a diversified trader guy. That's not what I do. That's not my job. My job is to build great products and get people to pay for them.

The second thing is I actually fundamentally reject the premise. Opendoor is priced in the public market for its potential, and it's an incredibly fair price for the potential. I think we will earn the potential. We're going to execute against it.

That's not that different from how startups are valued by VCs. You don't value the current cash flow of a company. You value the potential and say, “What are the odds it will get there? What's the discounted cash flow odds of this thing being big?”

If you do it that way, this is the single largest market in the world. I think Tesla was not above 10% in any market it was selling cars in until last year. It is above 10% in some markets this year. Opendoor was above 10% in many markets it was selling homes in a couple of years ago. We will get back there.

It's a significantly bigger market, a significantly higher attach opportunity, and a significantly longer ability to have a relationship with the buyer and the seller. By the way, I'm a math nerd. I was a mathlete growing up. If you do the math on the potential of the company and just discount it back, I think the stock is reasonably priced.

I would have bought at this price. In fact, I did buy at a higher price than the current price.

The meme-stock thing actually has 2 parts to it. There's the price relative to value, and then there's obviously the combination of meme stock and activism.

I think the interesting thing here is that a set of investors from outside have been able to agitate and drive change, in this case, I think, very interesting and good change. This is what the evil activists would be like if they were VCs, and it was just kind of fun from a distance to watch it, just rattling the cages of the board and saying, “You need to do something different.”

Eventually, the board said, “Hell, you're right. Let's do something different. Let's call Kaz and put these other guys back on the board.”

I think you're absolutely right. Look, I think the bull case for Opendoor is obscene. Just obscene. It's hard to exaggerate how big this company can be.

But companies require good stewardship, operational excellence, and aggressive execution. There are companies that can be run by professional managers. If you're a widget factory, professional managers are great for you. If you're a software factory, professional managers are death. I'm no one's idea of a professional manager.

So, we're going to create alpha.

Are you a software factory, though? You have a lot of real assets on your books. You have a lot of illiquid assets on your books. This is a very real-world financial mechanics business in a lot of ways. It's not a software factory.

Mm-hmm.

2. The Software Leverage Thesis

I fundamentally disagree. Opendoor is a software company that happens to have some assets. I think there's an asset-light model here that could work incredibly well. There's an asset-heavy model that can work incredibly well, and we'll have, literally, all of them. You must judge companies based on where leverage comes from.

You look at a company, and you're like, “Ah, that's where leverage comes from.” The leverage from Opendoor will come from software. We will build excellent software products for buyers and sellers of homes and owners of homes, and we will attach services to those products.

And one level down on that, because there are two things you do. You have to be able to predict the price of an asset. Well, maybe three.

Mm-hmm.

You've got to have a top of funnel to drive in buyers and sellers. You've got to have a really big AI brain to figure out what these assets are worth, and then you've got to have transactional efficiency to make all the shit happen, like the processing, the selling, the repairs, all that. Maybe those three things are the software—what you're calling the software factory. Which do you think is the hardest part? Which do you think is the most important part?

So I think the last part is very software-enabled, and generally, I'm actually 24 hours and 12 minutes into the job. I'm generally impressed by the last part of the business already. It could be significantly more software-enabled, significantly more AI-enabled.

Yeah.

I'm actually generally impressed. But I think the long-term leverage for this company becomes offering a fair price for a home.

Yeah.

Not trying to make all your money on buying homes at a discount.

Yeah.

That's just—no one wants to pay to have that. Selling a home for a fair price and adding value-added services on top of it, adding things that homeowners and home sellers want as a part of that transaction, and you've earned the trust because the price is fair. The house is good. It's valuable. You're not selling lemons.

We will get to a point where you will buy a home from Opendoor. I'm not saying tomorrow, but you will be able to buy a home from Opendoor, and if you don't like it, you'll be able to return it. We'll get to that point.

We'll get to a point where you'll be able to buy a home from Opendoor, and we'll stand behind it for the life of that house. You'll be able to treat it as though it's a guaranteed asset that we will take care of and take care of you as a buyer of that house.

As a seller of that home, we'll be able to get to a point where we will find you a new home. You don't have one? Great, we'll find you a new one. We will find a way to make the liquidity work in the long run, and we'll focus on both buyers and sellers.

For what it's worth, this isn't uncharted territory in the public markets. Carvana has a very good model of this, where they offer a fair price to the buyer, a fair price to the seller, and make margin on added services.

First of all, big-picture comment: I think this is one of the hardest business models out there. I totally see the upside, but clearly, when we look not at Opendoor but at some of the others, this is one of the most challenging problems I can imagine.

You made the Carvana analogy, and it's fair. As people know, Carvana was another high flyer in 2021, selling cars, doing the same thing for cars. It flamed out in 2022. Investors, including Thrive, held and bought some more. The stock's up well north of 10x. Everyone who held and bought looks really smart, and obviously, if I was you, that is the mental model I'd be pushing all day, every day.

One of my many nagging worries about this is that it's easier to price a car than a house, right? The nuance you have to get right—prove me wrong, but you can get within 7, 8, 9 percent pretty accurately on comps. But it's the little shit that, when you walk around the house, “Oh, they have an extension. That garden's nice.”

It seems to me the last 8 percent of the price, which is where you make all your margin, has a lot of variety, and I could be wrong, but that seems to me the hard part of pricing.

Right, I think you are wrong.

Cool.

I think you were right. I think you were right 3 years ago. I think 3 years ago, this was an incredibly difficult problem that required human beings to visit homes and look around and look at the shape of the garden. That's a real thing.

If one side of the street has a slope and the other side doesn't have the slope, those 2 things are priced differently. But there's a reason why God invented AI. This is a solvable problem today. We don't need to limit ourselves to what human beings can see. This is a real thing. Human beings are variance-creating machines. We can build software systems to solve these problems.

You know what the funny thing is? Shopify is a notoriously bad business. It's a high-churn business selling to small businesses at a massive discount. You could buy Shopify for $1. $1. It's a SaaS product you can buy for $1. There are no seats. There's no seat expansion.

Yes.

Shopify is the best deal in SaaS.

Yes.

When you buy software, it's the best deal in SaaS. We make our money when you succeed, i.e., from services at Shopify.

Opendoor will be the best deal in buying and selling homes, and we will make our money by adding value to those homes in ways that other people cannot do because they don't understand a home, they don't understand a buyer, they can't underwrite your risk, and they can't provide additional services.

The problem with having to make all your money in one transaction is that you, by necessity, have to be shady.

Correct.

Right?

No.

This is why people who sell used cars aren't typically awesome people, because they have to make all their money in that one-half hour. Whereas if you make your money in the long run from a long-lasting relationship with the counterparty, you have an incentive to do right by each other, and this is actually a key differentiator of what we will do.

We will create a network for buyers and sellers, homeowners, home buyers, and home sellers, where they will have a long-term relationship with us over a series of products we will launch. Some of them will be free just because they're good. Some of them will not be, and we'll make money on them.

Title, mortgage—there's a whole bunch of things that happen right there that are wildly profitable on top. I mean, title insurance is the world's best business because no one ever pays out a claim. How do you think about the role of the real estate agent in this? Because that role is changing also, and obviously, it's 6 percent—

Yeah.

—in a world where you're making 8 percent. How do you think about how real estate agents fit in?

Look, I think there's a structural issue that we need to think through, which is this: transactions and relationships that have many intermediaries are typically not great ones.

Yeah.

They're just not awesome transactions, usually.

Yeah.

You usually want to look the person you're dealing with in the eye and deal with them. That's what the real thing is. Now, do I think there is a place for experts to help either side? Yes, in some cases, but not in all cases. In some cases, you will. I'm not dogmatic about this.

Okay.

But I do insist on an excellent fucking product—an excellent product that a buyer and seller can use and be proud of. If some set of those buyers and sellers want to have someone else help them, great, but we will provide an excellent service to buyers and sellers, and if, in some cases, we have other people involved, that's fine.

I didn't really fully get the Shopify analogy until just then, but Shopify gets only 25 percent of its revenue from software, and that percentage is going down, right? It's one of the best deals out there. I mean, maybe ChatGPT is a better deal, but they've got to earn the other 75 percent through merchant services and others. You had to earn it.

Yep.

In 3 years' time, will you have more of an asset-light model, or will you be more of an asset-heavy model?

I mean, the company doesn't have an asset-light model right now, so yes, by definition, yes. Yes.

Well, no, but you can choose to stay asset-heavy, or you can choose to transition—

We will not.

—to asset-light.

We will not choose to stay in a solely asset-heavy world. Look, guys, I'm not a publicly traded company, et cetera. I don't have a magic plan that I'm executing against right now. This is 24 hours and 19 minutes now, but we are going—

Yeah.

You have 7 more minutes, Kaz.

Come on.

Well, the last 19 minutes have been wasted, he's mentally saying to himself. But keep going, Kaz.

I think what you need to do is look at the problem space and solve all of it for the user. You need to look at the problem space and solve all of it. It's incredibly hard to build good products; therefore, it is incredibly hard to build good businesses if you're solving the tiniest problem that you happen to think is profitable. By the way, if you do that, you end up with adverse selection.

Yeah.

The market eventually clears properly, and if you think for a very long time you're going to have a 20% margin buying homes cheaper than someone else, you're just straight-up dumb. The market eventually clears appropriately. What you need to do is be incredibly efficient on the first transaction and incredibly valuable on every transaction thereafter, and that's our job here, and we're going to get there.

It's going to take us a second. We're going to screw a bunch of things up. We're not going to be perfect. We're going to launch things that won't work, but we're going to start fucking launching things.

3. Founder Pay And Air Cover

How did the comp discussion go? It's quite notable that you aren't taking a salary, pretty much, or $1 or whatever it is, until you—

I would take less. I'm not allowed to. I'm not allowed to take less than $1. I would gladly take less than $1.

So when you hit $30, you get remunerated.

A lot of money.

You get remunerated.

If I could have structured it the following way, I would have. I think corporate executives should basically only get paid in options. I think it's a very weird world where we create an incentive for corporate executives to be bad at their jobs just to get paid. I think it's just so fucking weird, where the thing you've created is, “Be inoffensive enough not to get fired.” That's very weird.

That's RSU life.

I own no RSUs. Zero. Actually zero. Literally, the entirety of my performance money is based on the stock price going up, and there are different cliffs. Some of it is a phantom option, where if the stock price goes down, it's worth zero. Some of it vests based on price.

This is complicated because of very odd Delaware and SEC rules, but I would have gladly taken just options. In fact, that was my preferred state. But we have tried to construct a thing that looks just like options, with some ups—some vesting over time with stock price.

I don't have Yahoo Finance on my laptop. I will not look at the stock price every day. What I will look at is delivering value for users and shareholders of this company over a long period of time, and that's what we're going to do. I think this company is incredibly valuable. I thought when I joined Shopify that the market misunderstood the opportunity. I think the market massively misunderstands the opportunity for Opendoor, just by an order of magnitude.

Can I ask how important you feel it is that you have Keith and Eric coming back into the fray as well? That's another—

I wouldn't have taken the job without them. Straight up, I wouldn't have done it. In fact, I said I won't do it without them. We're going to do things that look odd, but what they look like isn't important. What they are is important. How things look is less important than what things are, and we need people who will be with us while we take those risks.

I think that's super interesting. The whole private-versus-public thing—there was a great article in The New York Times recently on why being public is a pain in the butt. I think you're exactly right, Kaz. This is a refounding of the company, and if you didn't have that air cover from those guys coming on, it's just really hard for a standard corporate board of a public company to do the kind of painful work you're going to see in the next 12 months to turn this thing around.

Yeah.

I would agree with you. I think that if I was advising someone as a CEO to take this on, your first question should be, “Where is your air cover from entrepreneurial people, not the kind of people you find doing a public board for $200,000, who will allow you to do this?”

If you don't have that, invariably, you're like the poor guy at Intel. You have this big, ambitious plan. You tell everyone on the board you have this big, ambitious plan. They all agree, and then one year in, it's like, “Oh, my God, it's terrifying. We're out of here.”

I think you're exactly right, and it's a rare combination to be able to have fixed the—I wouldn't say fixed—to orient the board around the task at hand.

We have great board members, but I view them as colleagues and coaches. There's a board member who's coming into the office in a couple of hours because we're going to go through literally every house we own, line by line, together with that board member. They're going to sit next to me. We're going to go through everything.

One of the first things I did was get the board member, and I went through literally every invoice the company had paid for the last 12 months. Actually, every single one of them—I reviewed every line item. Our board members are going to join us along this mission, and they're going to work as hard as we do. I'm incredibly excited.

Do you want Chamath to come back into the fray?

Dude, the world can't have enough Canadians, man. It's a real thing.

The man wins. Kaz wins. That was a killer answer.

Final one from me, and then we'll let you go. When you made the decision, you had a huge amount on the table at Shopify—

Mm-hmm.

—and you left that for this.

Yeah.

How big is this, then?

A few hundred million dollars.

A few hundred million dollars, exactly. You believe that you will make more here, and what is that upside here when you made that evaluation?

I don't optimize my life for money. I just don't. When my wife and I got married, we decided to optimize our lives for leaving a dent on the world. We will leave a dent on the world, and that's what we optimize our lives for.

Having said that, I'm incredibly bullish on the bet. I would not have taken it if I didn't think it was going to pay off. I'm very, very bullish on the stock. I'm very bullish on the company. We will build a generational company here, and this is my ask of everyone who has bought the stock and is cheering us on: We must be held to account for doing that.

We must do both things. We must build a company that makes the world a better place, and we must deliver shareholder value, and both of those things are incredibly important. I'm asking people who have bought the stock in the hope that we will do the right thing to hold us to account and call us out when we don't do the right thing.

This man has put his money where his mouth is, and that's pretty damn impressive. You've walked away from an exciting, challenging, extraordinarily well-paid, very manageable, safe gig to double down on—as I say—a truly challenging problem, so it will be fun to watch you figure it out.

I optimize my life. At the end of every week, I write down a note to myself: Was the week hard? Was it valuable? Was it fun? At the end of every week, I judge my week based on hard, valuable, fun.

Yeah.

That's the goal every week: to have all 3. I find that you can't have fun unless you have the first 2. I had my first all-hands yesterday at the company. I told the team that we would value this company's next year over hard, valuable, fun.

I don't know where the offices will be. We're going to figure that out this week. We'll announce them to the company on Monday and to the world on Monday. Opendoor will be the most aggressive in-office public tech company. If you are a builder, if you want to build a future that is better for homeowners, that tilts the world towards owners rather than renters, find us. We're going to build an exceptional team and ship exceptionally fast. Uh, my DMs are open. Send me a DM. I don't know where the offices will be. I will know on Monday, but we'll figure it out.

Kaz, you are a hero, man. Thank you so much for being with us—

Thanks, guys.

—on your second day. You are a hero.

Thanks, guys. Have a great day.

And now keep going. Good job. That was awesome.

Thanks, guys. Have a great day.

And now keep going. Good job. That was awesome.

Thanks a lot. Bye, dudes.

Thanks, guys.

Have fun. It's lovely to see you guys. Uh, that was a great start.

It was great.

Uh, we're gonna get back to normal programming, baby, and I wanna start with Oracle and OpenAI. Oracle touching a trillion dollars. Rory, you're always quite good at setting the scene, and I actually got given some good feedback the other day, which is we need to set the scene for the stories. People love the analysis, but they like to know actually what happened. Can you just help set the scene of Oracle, OpenAI, what happened?

4. The Oracle OpenAI Bet

I want to start with Oracle and OpenAI. Oracle touching $1 trillion. Rory, you're always quite good at setting the scene, and I actually got given some good feedback the other day, which is that we need to set the scene for the stories. People love the analysis, but they like to know what actually happened. Can you help set the scene of Oracle and OpenAI—what happened?

Sure, and I think it is good feedback. We often forget that we dive right in. Let's step back. What happened is Oracle announced, I want to say, their—whatever it was—Q2 results.

They have an off-year, an off-cycle year, so it might have been Q1. For what it's worth, they were actually a little light on the quarter's results, but they announced future RPO, revenue performance obligation, of north of $300 billion. In other words, they said, “We've got orders as of now that we have to deliver in the future for well north of $300 billion.”

They didn't say this, but you figure it out: most of it is a big OpenAI order for around $300 billion of future cloud compute for its AI platform, and the stock exploded. The stock went up 36%, 38%, I think, briefly making Larry Ellison the richest man in the world. Yay, Larry, and Oracle touched $1 trillion. It's unparalleled for a top-10 company to jump by 38% in one quarter, so a huge jump. Since then, there's been some skeptical commentary, but that's what happened.

How did we analyze it subsequently? How did you feel when you read it? As you said, there were skeptics. How did you feel?

I suppose I was a little skeptical, but then—positive spin. If you believe the revenue, $300 billion, let's just say if you think OpenAI has $300 billion to spend, plans to spend it with Oracle, and does in fact spend it over 5 years, that's $60 billion of revenue a year, divide by 5. So even at a 5- or 6-times revenue multiple, that gets you to $300 billion in delta market cap, which is exactly what happened.

If it's 100% money, good, and you can say it's some kind of recurring revenue thereafter, then it roughly corresponds to the increase in value. It's just that then you say to yourself, slowly, the customer promising to give you $300 billion is doing $12 billion in revenue, has raised—I can't remember—$40 billion total to date, is still losing significant money, and therefore is going to have to raise, as Sam Altman has said, a couple hundred billion dollars—he said $115 billion, but who's counting—to be able to pay you that money.

So you look at it and you go, “This is a very levered bet on everything at OpenAI working.” To some extent, it's kind of like a proxy for OpenAI stock. It's like, I can't buy OpenAI in the public markets, so if OpenAI is successful, it will have $300 billion. If it has $300 billion, it will give it to Mr. Ellison. If it gives it to Mr. Ellison, Oracle's stock will go up. It feels plausible, but non-risk-adjusted. You're applying 100% certainty to 2 or 3 things, each of which has a fair amount of uncertainty associated with it. That was my net takeaway.

Have any of us given up caring whether any of this revenue is profitable? I think the bet that OpenAI can come up with the money is a reasonable one. They may not, right? There's some risk there that they don't, but so far Sam has found a way. Jesus Christ, CoreWeave and everybody these days say they have insatiable demand, so that's okay.

But no one cares that this adds nothing to Oracle's bottom line, and may never. No one cares that Oracle is basically a fungible set of server services for folks who don't want to bother bringing it in-house. I mean, this is, for the foreseeable future, a zero-net-margin business for them, isn't it? It's good for VCs; we don't have to look beyond the top line. It makes our lives much easier. We don't have to worry about silly things like inference costs and gross margins because the public markets don't care anymore.

You are right. From the perspective of, say, 5 or 10 years from now, the people selling cloud computing to the people who own the models will probably not make as much money as the people who own the models. That's a pretty obvious statement, right? Even though OpenAI is losing a lot of money now, being a commodity provider of services to them over the medium term means being an even less profitable, more commoditized business.

I prefer to own OpenAI over CoreWeave, and to the extent that this is just CoreWeave 2, you're totally right, Jason. Now, the fun thing is we are dealing with the man who most successfully on the planet extracts operating margin from software companies, which is Larry Ellison. That's why he owns 41% of this damn thing, up from 27% a decade and a half ago, getting that free cash flow and recycling it back.

But you're right. This does feel like getting $300 billion in revenue and, to your point, Jason, in return having to spend a whole buttload upfront on CapEx for a business that, however profitable it will be—and maybe it is profitable—won't be as profitable as the 41% operating margins that they currently get from selling databases. So I agree. Even after the revenue—

But it's nothing today, isn't it? I mean, literally, this business is consuming cash.

I'm sure. Well—

Right?

Yes, and you probably have some kind of positive accounting gross margins, but really it's all about the assumptions you're making on your CapEx depreciation. If you know over how many years you should depreciate the latest NVIDIA chip, then that would be the key question.

This isn't a bunch of memers getting excited about CoreWeave. This is Oracle. This is a company founded in the '70s, where the public markets are like, “We don't care that your new GPU-hosting product has massive top-line growth, right? We don't care at all that it's contributing nothing to the bottom line. We don't care. We don't care even an iota.” That's what the public market said, didn't it?

Agreed. No, you're right. Jason, you're exactly right. I think it's equivalent to, but with more success than, the Facebook-Meta story. You have an existing business. It's freaking awesome. It has nothing to do with AI. It kicks off 41% operating margins for Oracle, and high 30s to 40% for Facebook.

The market is saying to you, “If you've got all that free cash flow, have at it, big guy. Throw it back in and see how it goes.” In the case of Meta, they're not penalizing him, and in the case of Oracle, they're actually rewarding him for doubling down on unprofitable growth. So, entirely rationally, he's doing it.

It's got to feel freaking great when you've been cranking like that guy has for 50-plus years. Whatever it makes of the stock long term, the fact that you sprinted ahead and were, for a brief shining moment, the richest man in the world, probably that alone is worth whatever future damage you've done to your operating margins. It's great.

Is this not an ultimate sign, though, of where public market irrationality and exuberance is? Sam Altman says in this announcement that the margins associated with this order are what they are, and the stock jumps 38% at this scale. Is that not the height of irrationality?

You mean, unlike us sober, careful, and sober-minded private-market VCs? Yeah, I'm shocked to discover gambling going on in the stock market, Howie.

Yeah, it's pretty frothy. Look, there's been froth in the private markets for AI for 2 or 3 years, and probably the public market is saying, “I'd like to get in on the game,” and this is one of the few ways to play it. So I agree, it's frothy. Is it more frothy than any of the things you're seeing or I'm seeing? I don't know. Who am I to judge?

The one thing I do think is important—we mentioned the margin element—is that I have never before seen such a lack of investor diligence on anything except top-line revenue growth. Ever. It's astonishing, where updates can be hundreds of millions of dollars wide without a discussion on margin, number 1.

And then, number 2, it's just like growth is amazing until it doesn't grow anymore. When you look at this, if OpenAI doubles between now and July 2026, and then doubles again between July 2026 and 2027, they'll be at $48 billion and still $12 billion short per year to do this. At some point, growth does taper.

Agree. Do I think they're going to collect $300 billion in orders from OpenAI? Absolutely not. There, I'll say it. I think they've got a business. I think they'll get more revenue from OpenAI. Do I think the full last $300 billion will be wired in 5 or 6 years? No, I very much doubt it.

Is this market not just all about shouting as loudly as possible? Do you remember Stargate? “We're going to have $500 billion.” What happened to that $500 billion? Seems like there's a lot of—

It's a classic, really cynical question. Isn't this one of those where everybody just announces the same thing? So, yeah, it used to be SoftBank, but wasn't Oracle part of that?

But Larry was right. It did happen. This is a big part of it.

You think Stargate.

This is Stargate.

Honestly, to me, it's a reminder—we've talked about this—to really scrutinize Sam to see the future, because he goes to Trump, right? And he's got Masayoshi Son from SoftBank and Larry Ellison in that awkward photo. Elon Musk wasn't there when he was still running things, right? This was a couple of months ago.

Announcing the Stargate thing, I'm looking at it thinking, “What's this uncomfortable Larry Ellison, who doesn't look like he's put on a suit in 3, 7, or 8 years, sitting there squirming in the White House?” We should have bought Oracle stock that day.

Yeah.

Why didn't we put the whole fund into Oracle? Why did Sam make him come? “We've got to do this,” right? That was a telling moment to me, but I didn't get it at the time. This just seemed like the oddest photo op, and it seemed like dissing Elon Musk, but it wasn't that at all, right? This was the future.

I mean, I think one of the things that's obvious from this is that everyone is getting what they want from this press release.

Larry Ellison is becoming the richest man in the world because his stock is going up 37%. Sam Altman is getting, frankly, leverage in his negotiations with Microsoft by making it clear he has another CapEx provider willing to spend vast amounts of money. To some extent, this is happening because everyone involved wants it to.

I'm willing to bet they want it enough that they're not sitting there going, “Are we 100% sure this is going to happen? Or do we just have a credible case that says this might happen and it will be good for us in the short term?” To be fair, especially when you're trying to do something as ambitious as OpenAI, momentum is your friend, and momentum is a necessity. Things like this just keep building on the momentum and keep building on the sense of inevitability.

You're right, Harry: it's the role of investors to be a little more cynical and scrutinize and say, “Do I really believe that that's going to turn into $60 billion a year of revenue? Should I really mark Oracle up by that amount?” Clearly, they forgot to do that this week.

5. Venture Becomes Trading

This may be a broader point, but I just feel like the whole venture landscape has moved from a game of investing to trading, in a way that we're all just hoping someone pays a more irrational price than we paid while we suspend disbelief in the meantime.

We've got a couple—I think we still have a couple of good years until something happens, so we might as well play the game.

Are you going to be the Chuck Prince of our generation? Remember, while the band keeps playing, you gotta keep dancing—the CEO of Citigroup in 2007. Jason, you might regret that quote.

I've kept dancing with Hopin, BeReal, and Clubhouse, and you know what?

You're done.

The party stops. I'd rather stop dancing.

Yeah, but what happens along the way is that there are exits.

So I think the big question for venture—and I think where we're going to make a lot of mistakes in venture—is not taking billion-dollar exits over the next 24 to 36 months. We're going to triple down. There are going to be board members saying, “Rory, we've got a $4 billion offer for our latest AI tagging and categorization software at, what, 3% gross margins. Let's not—I want eight. Or 12 would be better.”

You know what's better than 12? 24.

24.

And we're going to say no to those fund returners, and we're going to wake up, and they're going to be worthless. I think that's what's going to happen. If you're in the game now, you gotta have a couple of big exits and IPOs over the next couple of years or quit the game. You gotta have a couple.

First of all, you are right that that will invariably happen. We're at that stage in the cycle where you've got a large amount of euphoria, fairly untethered, and the positive spin—which I think is true—is you don't make these kinds of technological leaps and technological investments without a fair amount of accompanying euphoria.

This is a means to the end of moving the needle forward on AI. We gotta try a lot of stuff. A small amount of it will work, a large amount of it will fail, and a lot of money will be lost in the end. But the good stuff will ultimately outweigh the bad stuff. This is the way it happens.

But to Jason, your point in particular, I've been around long enough. I remember a bunch of those companies in ’99 and 2000 where you got the offer for $2 billion for some fiber-optics company or for some communications-equipment box, and the board said, “Damn it, we want eight. We're turning it down.” Then you'd meet the team 2 years later, and the company was worth zero, and most of those folks were shell-shocked. It's like winning the lottery and then losing your ticket. It was brutal.

So I think being canny and shrewd about what chips you take off the table in the next couple of years, I think you're exactly right, Jason, will be a key part of the game.

I also think people mistake valuation for liquidity. Just because it goes up doesn't mean you can get out. If you can get out, it's often at a discount to that priced round. And if you can, it's often in a strip where they'll give you 10% or 20%, but you can't get out as much as you could selling it all now. I don't think people think about that enough.

True. And I think one of the things we're going to discover is that when all this action was happening in the public markets, you had this weird, somewhat positive phenomenon, which was that everyone was up, with constant liquidity. You know, you can buy in at $80 a share, it goes down to $70, and you can say, “I was wrong, I'm out.” Someone else thinks, “I think it's going to be okay at $70,” and they go out and they're wrong, and it goes to $60.

You can parse out the pain among various investors who come in and out of the stock. The interesting thing on the private side is you've bought in high, and the whole point of private is there is no meaningful liquidity. If you're wrong, you're going to own it all the way down.

It's going to be a lot more fun on the upside and a lot more pain on the downside when you don't have liquidity to fulfill the role of liquidity, which is to allow you to alleviate risk. That's just the game we're in, and that's just the nature of being private for longer.

Every single founder this year that has had a strong M&A offer—

Yeah.

I've told them to take it 100% of the time. Now, I actually don't necessarily want them to take it. I don't want to be the guy saying, “I want to double down and quadruple down.” I don't want to be the guy who, a couple of years later, finds out it didn't work out.

So I'm telling them to take it, and if they come back and say, “No, I'm confident...” Here's my new heuristic. It's so simple: “No, Rory, I'm confident we'll be worth 10 times as much. No, I'm confident we will IPO. I'm confident...” Kaz just left hundreds of millions of dollars behind at Shopify, okay? Right or wrong, that dude's confident. We just heard it.

Now, it's not all about the money, okay? But he's confident this was the right decision. But I'm telling the opposite. I'm telling every founder, “Take it. Take it. Take any massive offer. Take it.”

I want them to come back and say, “Fuck, no way. This is gonna be bigger.” I don't want to have any of those regrets, and I think it's the right approach. Telling them to do that makes sure that I don't screw it up as a GP. It's just so easy when times are good to say, “Oh, Oracle's gonna get another $500 billion, aren't they?”

I don't love your sentence, but I actually think it's right. Your advice should, to some extent, be tempered by the time. The Bayesian prior at a time like this, when valuations are at an all-time high, should be some version of what Jason said.

Now, it's still possible that you're the one in 10 for whom an all-time high is just a step on the journey and maybe you should play the game out because you're so confident it's going to be amazing. I mean, look, it's very noticeable that 3 or 4 times in the last year you've seen significant M&A driven by founders at the same price that VCs either had just invested or were about to invest.

In other words, that's the founder saying, “The VC investor is investing, thinking, ‘Oh, you're worth $2 billion. I'm gonna give you money at $2 billion. I think you'll be worth $6 billion.’” Then 3 weeks later, the founder is saying, “You mean I can actually get the $2 billion? I'm out of here.” To some extent, that happened at Scale AI. I think there was a pending offer on Windsurf.

And that's founders, Jason, maybe listening to you and being shrewd and saying, “I could be at a local maximum here. This is a good time to take the chips off the table.” There's a little bit of information in that about how much, dare I say it, more shrewd they are about the value of the asset than the investor who is about to write a check at the same price.

I completely agree. I also think it goes back to incentives and how investors, as we said last week with Jeff, have many options, and we wanna ride them as much as possible. Founders have one, and it's their whole net worth in it, and that drives a lot of decision-making, I'm sure, tied to that.

I do wanna be cognizant in terms of—

Sure.

—how we discuss the topics we have on the agenda. We mentioned Oracle and OpenAI. Microsoft's relationship with OpenAI is slightly changing, it would seem.

6. Microsoft Moves Beyond OpenAI

Microsoft and OpenAI's relationship is slightly changing, it would seem. Jason, why don't you give a snippet on what this means in terms of the news between them and how their relationship is changing?

Listen, we have more to learn. It's gonna be interesting. Microsoft, I think, said today that it's moving not just parts of Office to Anthropic, but making Anthropic the default choice for several of its products. Microsoft also said that several months ago, it told its teams to start using Claude Code.

So they've been breaking up at some level for a while, and I guess it's fine. It sounds like OpenAI is going to get some of what it wants. They're going to get this revenue share reduced, and they're going to get their freedom to partner with whoever they want. I'm not quite sure what the price in blood is going to be back the other way.

But already Microsoft's moving on. They're already moving on. They got the IP. They're going to keep the IP, I guess. They're going to keep whatever IP they're allowed to keep before AGI. So they've got all the code if they wanna do anything with it, and they've already moved on to Anthropic, which is good because I think ChatGPT is probably going to end up being almost as good for coding as Anthropic.

The whole thing—the shifting sands of AI—is a lot to process.

Yeah, it is. And it's worth pointing out that it's some kind of interim MOU. It's not a final, done deal. It's both sides saying, “We're making progress here. This is where we're ending up.” This is a moving on. This is consciously uncoupling here.

OpenAI had this weird structure for reasons we all understand. Microsoft ended up with this weird investment that, in my view, gave them a fair amount of blocking rights in a lot of different ways. It gave them access to 49% of all the profits up to a certain amount. It had revenue share. It had a lot of things that effectively made it a bit of a poisoned chalice for OpenAI in terms of making it a real, proper standalone company.

What's clearly happening now is that it was a marriage of convenience for a while, and both parties are moving apart. I'm not sure where it ends up, but the rational end game for Microsoft is, “We got something along the way, but we don't just need a model anymore. Anthropic looks to be more useful for this. We still have access to their model. We like that, but we can buy that on a third-party basis. Just give them money and be a customer of the model. We got some lift from AI in the short term. We have some business with them as a hosting provider for Azure.”

All those are good things, but in the end, my guess is they convert that $13 billion investment from a blocking kind of thing to a 20% to 35% ownership stake in OpenAI. If OpenAI is worth $500 billion, Microsoft will have put in $12 billion and will probably have an ownership stake worth $100 billion to $150 billion. It's a 10x venture return on $12 billion. In one sense, it's a great return, but as you guys know, we've talked about this: it doesn't move the needle when your market cap is $3 trillion.

You don't get paid as a large-market-cap company for making, oddly enough, $100 billion, because when you've got a $3 trillion market cap, it doesn't move the needle. When you zoom out 3 or 4 years, I think the conclusion will be, “Wow, that was an interesting investment. We got a bit of a lift from Microsoft's perspective. We made a lot of money, but it doesn't move the needle. We got some buzz on AI in the short term, but we didn't really get what we wanted, and we don't have what we need in terms of AI. We probably have to keep cranking on that.”

In 3 years' time, how do you think the relationship will look between OpenAI and Microsoft, and then Amazon and Anthropic—the pairings that we've seen so far?

I think it's clear that Microsoft will be a large shareholder. Hopefully, OpenAI will be both a customer and a vendor for them, because they will be selling cloud capacity to OpenAI, but not on an exclusive basis. They will be buying access to the models from OpenAI, but probably not on an exclusive basis, because they'll be moving to Anthropic. In other words, it will be a perfectly normal relationship between the largest software company on the planet and this entity that they helped form, fund, and start, but that has now grown up. It's left the house. They're no longer dependent, and it's just a perfectly fine, arm's-length relationship with massive equity ownership that's probably going to make them $100 billion to $200 billion.

That's a lot for anyone else, but the real value to Microsoft has been the lift in its perceived market cap, and its actual market cap, from the perceived AI buzz over these 2 years where, frankly, they had nothing. To put the heat back on the Microsoft team, the real question would be: when OpenAI finally pulls away and you can't rely on your complex AGI agreement with them to get access to the AI you want, have you built your own AI that matters? Have you done something? If you have, that's great, and if not, then you missed that market. That's where that one will be.

I don't have as good a sense of Anthropic and Amazon. I'm not as informed on it, maybe. I'm not close to either, but my guess is much the same. Often, when big companies partner with a small company, the small company gets smothered. In both these cases, the small company won. They got the money, the critical mass, and the credibility, and now they've pulled away.

Neither Anthropic nor OpenAI needs Microsoft or Amazon at this point. They don't need them for money because the industry will give them infinite money. They don't need them for compute because Larry will give them infinite compute in return for money. They don't even need them for distribution. In fact, both of these companies, ironically, just like Microsoft 30 years ago, used IBM and then left it an empty husk.

I would argue that Anthropic and OpenAI have used their large corporate relationships and gotten the value out of them. It's still a bit sticky because the agreement is weird, but fundamentally, they've made it. They're independent, standalone companies. “Thanks for your help, guys. Here's your equity position. Call me for the IPO.”

And Rory, thanks to your description of an empty husk with Scale AI. I had them in my inbox this week asking to come on the show and tell us why they're not an empty husk, so thank you for that. That'll be coming to 20VC soon, which should be an interesting one.

We all thought that for a long time. It was a weird deal. Microsoft buying 49%, in essence, of OpenAI was the first of those deals—the Scale and Windsurf deals. But it didn't turn out that way. They didn't leave a husk. There were some superficial similarities, but in the end, we all thought that, in fact, if we had done the show the first time, we probably might have still said that Microsoft had basically acquired OpenAI. It was an acquisition in disguise.

As it's turned out, that's not the case—not remotely the case. Kudos to Sam Altman for dancing his way out of one of the greatest bear hugs of all time. He was basically having to sell his company to Microsoft to get it off the ground, and now he's going to get out of it.

Absolutely.

He's going to get out of it. Wow.

No, you're exactly right. The truth is, on the empty-husk comment, when the founder goes with the acquirer, it's a bear hug. It's an empty hug. It's an empty husk. When the founder stays independent, like Sam, it's a stunning win.

I think you're exactly right, Jason. Paul Graham—you have to give him credit—said it: you could put him on an island with a bunch of cannibals, and he'd be king. You put him on a plane to Seattle, and he came back with a bunch of money, and now he's king.

This is what I find funny. We go back to the Oracle and OpenAI skeptics, and I'm like, “Fuck it. I'm not betting against him.”

Yeah, no, he might find some of that money. Do I think that Oracle will book a fair amount of cloud compute from OpenAI? Absolutely. Maybe not $300 billion, but if he's willing to provide it at a lower price than Microsoft, my guess is those fine people at OpenAI will take it.

You know, another thing—when we had Kaz here, with him leaving $200-something million behind—it's difficult to fully predict the outcomes of these things when you have post-economic people. Not only did Sam not leave the husk, but because he had no equity in OpenAI, Microsoft couldn't pay him enough to move over and de-huskify because he had no equity to husk.

I mean, Kaz may make $1 billion. Harry was kind. His job is to make $1 billion from Opendoor, but even risk- and time-adjusted, leaving $200 million behind to Shopify and another $70-something million in grants and what he might still get, you could only do that if you're post-economic, right?

I especially hate it when some guy who was a senior marketer at some company and spun out with a couple million bucks tells everyone he's post-economic. But Sam and Kaz are taking post-economic actions, and it's very interesting in today's world, where a couple billion dollars isn't very much in market cap or valuation—not in personal income.

A couple-billion-dollar seed round is barely going to make Harry's show.

7. The AI Application Explosion

What's next, Harry? We're going to dive into the application layer, and two that Jason is passionate about—and I'm really excited for this, actually. One is Higgsfield, and the other's Replit. Jason, which one do you want to start with there?

Either one, man. There's one thread. There's this Higgsfield-Gamma thread, and I think it's somewhat interesting that both are slightly under the radar. The CEO of Higgsfield was not quite complaining, but sort of shouting this week when he did a round, saying that he's gotten to $50 million in revenue and, certainly in users, gotten there even faster than Lovable and friends.

I'm a small investor. I've been a user since it launched. I love Higgsfield, and Gamma at $60 million—from $0 to $60 million this year—that's pretty good for—

Just—

For Slides.

Just to be clear—

Okay.

Higgsfield is an AI video creation company—

Yep.

—that raised $50 million and also announced $50 million in ARR—

Yeah.

—in a faster timeframe than Lovable and Replit.

Yes, and maybe Gamma's close, too, right? We could talk about Higgsfield being under the radar if you're not a creator using the app.

Gamma, maybe folks on this pod have used it more often. It's still under the radar. I guess we could talk about that. My meta point is, my God, right? If you don't see some of these numbers, it's not just Cursor and friends and Replit, which we could talk about.

Right.

Going back to cars, homes are a big market. Restaurants are a big market. E-commerce, like Shopify, is a big market, but sometimes we don't even realize that short video and slides are massive AI applications. I mean, just massive. Higgsfield can do this in the shadow of Google, even though they're using Google models, and in the shadow of so much competition. It's just—

It's—

This is why it's so hard to do a triple, triple, double, double. It's not just Lovable. There are so many Lovables.

No, and—

There might be 20 or 30 Lovables.

And I think what you're seeing—I mean, stepping back, what you're seeing here is that with AI, there's a series of things that “ordinary people” couldn't do before, be it coding or video creation.

Couldn't do it.

And these tools are making it accessible to everyone. So you have this step function, 10X, maybe 100X increase in accessibility of creativity or coding.

Yeah.

And that's the positive momentum. And then the negative momentum on all these deals—the Replit, the Higgsfield—is, “Oh, my God, you don't control the underlying model. If you don't get enough scale, will you have challenges?” There's a lot of risk in those deals, but sometimes it pays to zoom out to the big picture.

The big picture is that anyone with internet access today can create cute videos, can edit videos, and can be creative in a way that 5 years ago you couldn't do unless you were a trained special-effects editor. And that's huge. And peo—

Maybe 6 or 7 months ago. You're right. But you couldn't do these things—

And now—

And now you can do it for pennies. You can do it for pennies. It's beyond disruptive, right?

Anytime you're dealing with shit that everyone can do, you have the potential for these exploding growth rates. You guys are living it with Replit and Lovable in coding, and I think Higgsfield is an example of that in creativity. I think there are going to be more of them.

Sometimes I would look at some of these things. I'd be like, “Gamma—we use Gamma all the time. I love it. But how the hell could that get to $60 million this year?” It's like, do we really make enough slides?

But to Rory's point, it's a way to create content you could not do before AI, so I get it. So many of these markets are bigger in the age of AI than they were pre-AI. I know it's Captain Obvious, but Higgsfield for short videos and Gamma for slides—even Opus Clip was the first little AI investment I did. I got it, but I didn't think it could add up to so much revenue to make these clips, right? You gotta get the spreadsheets right. You can't use the TAM spreadsheets from 2021.

I find this time a little bit like COVID, though, in terms of market forecasting, which is a real difficulty in understanding what is a sustainable market trend that will be meaningful and enduring versus what is an experimental market that is cool to create, but ultimately whimsical and doesn't last a cycle. I'm finding that uncertainty very challenging as an investor, to be quite honest.

But the thing is, we agree, but that conversation we've been having since the beginning of AI, and a lot of thin-wrapper apps died for that reason, right? What we are seeing—it's a valid concern for venture, but what we are seeing at least is that nominal NRR is pretty high in these apps.

So it may still crash and burn, don't get me wrong, but if you're using Higgsfield and Gamma, and Lovable and Replit, and you're seeing triple-digit NRR, even if it's not the NRR we used to talk about for B2B, it's hard to say no as a VC, isn't it? It's hard to say no when you see 140% or 180% NRR. You can say no and just sit at home and knit.

I don't know, dude. When the margins are where the margins are, you have to project out and go, “Fuck.”

But Higgsfield is profitable. It's cash-flow positive. It varies based on the application.

It varies based on the app.

They're not all Replit and Lovable with negative margins. They're not. I guess my learning is it's non-obvious: the margins are all over the place, right? They're all over the place.

Agreed.

Right.

And you're right. I mean, Harry, again, yeah, it's hard. You've got to figure out which exploding-growth company is going to be sustainable and which exploding-growth company is not. But at least you're dealing with the problem of exploding-growth companies.

Yeah, yeah, yeah, yes, but I'm an investor in a business, Airwallex, a very similar business to Stripe. This is an unwaveringly enduring, growing, strong market. Fantastic. Comparatively, these others are incredibly experimental, potentially groundbreaking, and potentially whimsical. Very different.

Totally. Agreed.

Well, you gotta be able to tolerate a loss ratio, if nothing else. You gotta be able to tolerate a 30% to 40% chance of losing your money on it.

They are very different. I'm not naturally good at these creative deals. I get all your points. It's my bias, and I tend to be the steady compounders.

But I think different deals have different attributes, and you've got to look at these and go, some of these will be flashes in the pan. So the question is, what's the distinguishing characteristic of the companies that explode and then sustain? My guess—I'm kind of riffing here, and we can talk about it—is probably 2 things.

It's probably having expansive white space that you can grow into with your customers. There are more things you can do versus getting cut off shortly. And then, secondly, having a founder who's maniacally focused on doubling down and adding all the rest of the stuff.

Something you guys said about Lovable and Replit a while back stuck with me, which is you can envisage a whole bunch of ancillary products around that. As people build their websites, all the other things it takes to make that website work, and you can envisage building an economic model around the combined thing.

So I think it's a combination of the opportunity and the founder. I think some of these things will be flashes in the pan. Not trying to be mean, but to use the Hopin analogy—like Hopin in COVID, right?

Right.

It will be a temporary phenomenon that goes away. But finding the ones where you have that explosive growth and then can parlay it into something enduring is gonna be pretty damn interesting.

We've never seen competition like today. Never. You used to have 6 months, maybe 12 months. You'd launch something, your competitor would look at it, decide if it was worth their time to build it, commit to trying it, then 6 months later get it. But you had a full year. Now you have 2 weeks.

Everyone complains about competition, and everyone's prepared to do anything to solve the problem except the one thing that will solve the problem, which is to step away from the table yourself, Harry.

So we've got too much competition, but you're not quitting, I'm not quitting. I mean, tough luck. It turns out, yeah, it's a very competitive time up and down the stack. It would be a lot easier if there were half the number of people, but the opportunities are compelling and people are gonna show up and try and play.

I could imagine—I don't think this is gonna happen, but it's not impossible—Anthropic could lose half their revenue in the next 12 months because GTP-5 Codex might be just as good. They could lose half of it.

Literally, all you do is turn it on in Cursor or Lovable or Replit or a million other apps. Whoever it is—Higgsfield or Gamma—moves over to GTP-5 Codex instead. And if GTP-5 Codex is as good as Claude Code, which it just launched, I could imagine it is 95% as good.

You could imagine, in today's crazy world, Anthropic could lose 30% or 40% of its Claude Code revenue in 1 year. It's very imaginable. I'm not saying it's gonna happen, but the switch—it could happen. Even that may not be stable.

Going to Harry's point, forget about whether Lovable and Replit and Base44 are stable. I'm not even sure Claude Code's stable.

To state the obvious, that would be a very different level of stability than we saw in the SaaS era, where these things lasted forever and they churned 5%. If you are right, Jason, if it's even 30% to 40% probable that something like that could happen—and I don't have a developed opinion yet on it—that's obviously a very different world you live in in terms of risk.

Yeah, it could be high risk.

The only interesting takeaway I'll take is that I interview, honestly, 3 to 4 decacorn CEOs every week, and on this topic, there are 2 interesting elements.

First, they're completely price-insensitive as to how much they spend on Anthropic and Claude Code in particular. They're like, “I would spend 10X. Don't even look at the line item.” Number 1.

Second, there's a duality of super-low switching costs and a complete awareness that they would very happily move tomorrow to someone else if it were a comparable service.

Yeah.

Which goes to explain the urgency around CapEx for these companies, because their belief—and so far it's been correct—is that if you're competing with Claude Code, all you know is the only way to outperform is more reinforcement learning, more pre-training, more whatever, which means more CapEx.

Hence the urge—the quote, “insatiable demand around CapEx”—because it’s the only way to win. All the players are being rational in the game, but you can see it adding up to something pretty scary.

8. Incumbents Fight Back

Kind of bringing this all together, the Higgsfields, the Lovables, the Replits—the thing that could also kill them is actually the fact that Wix has Base44, which is doing incredibly well. The fact that Adobe or Canva could do what Higgs Field does with the existing distribution they have to it. Going to the distribution and going to the incumbent versus startup, how are we thinking about incumbent versus startup and the core crux there?

The market would say that the Wix acquisition has worked very well. It’s probably going to be $50 million in ARR by the end of the year, so that’s a win. The market would also say, based on the fact that Adobe and, let’s be honest, Salesforce, have tried to announce AI products and gotten some traction but aren’t able to access that explosive growth, that the market reaction—the Adobe stock price—kind of reinforces that.

So it’s not a simple binary answer. Some folks have pulled it off, and it’s easier for $100 million to make a difference at Wix than it is to make a difference at Adobe or Salesforce—$23 billion in the case of Adobe and $40-something billion in the case of Salesforce—where it’s hard for those incumbents to move the needle significantly. That’s why the stock prices have been down, because you’re not getting the AI explosion.

For sure. But to me, the Base44-Wix thing is interesting because we’ve been asking for a while, “Can the incumbents benefit from AI the same way the startups have?” We’re looking at ServiceNow faking it, and we’re looking at—we had Mark Benioff, who we all love, but we’ve not seen it in the numbers yet. And we see Palantir, but Palantir is a completely different company—

Totally.

—that is AI-first. So we’re not seeing it. We’re seeing it in our own portfolios. We’re seeing a lot of our 2021 high flyers not exactly crushing it in the age of AI. There’s Dialpad and Talkdesk, but a lot haven’t.

But what’s interesting is, then you see Wix come in and buy a little Lovable-Replit clone that is just a cheap clone by one guy. I mean, kudos to him, right? Solo founder, right? Bought for $80 million, using the same underlying technology, Claude Code, right? But they bolt on what Wix is good at, which is safety and identity, okay? And then they bolt on the frigging funnel.

Totally.

They push it out to their base. And if that’s gone from nothing to $50 million in a single-digit number of months, imagine it’s $200 million or $250 million. More importantly, for the numbers, to Rory’s point, if it’s 10% market share, that’s a lot for a big-company distribution to get in a couple of months—10% market share.

So if Adobe could do that, if Figma could do it, if Figma can do it with its thing, could it be the revenge of the incumbent? I don’t see much evidence, but I like Base44 as one example of the revenge of the incumbent. I don’t want all of our friends to go down into irrelevance. I want to see Zoom back. I want to see everybody come back and be roaring in the AI age, not just the new guys.

I mean, speaking of incumbent and innovating as an incumbent, while we’ve been on this—

Yeah.

—I’ve been sent by a lot of people Workday acquiring Sauna Labs—

Yes.

—for $1.1 billion.

Oh, my God. Yes.

Wow. They were at, like, $50 million in ARR. That’s a pretty great outcome for everyone involved: $1.1 billion to Workday. I think Sana’s great, Joel’s great, but this was a second to Glean, very much so. Wow.

But you know, in these times, being number two can be a great place for M&A.

Yeah. Absolutely.

When number one is unacquirable, you get so many offers. I wish I’d realized it as a founder, right? I mean, knowing Rory, if I—even if EchoSign had just done okay and we’d gotten up to $100 million, the folks that DocuSign turned down would’ve come and bought us for a billion bucks. I wouldn’t have had to do anything, just be number two. I would’ve just had to open the email and sold for a billion at a moment in time.

Today, it wouldn’t have worked. In the age of AI, you can’t buy. Glean’s unsellable, unacquirable. Lovable’s unacquirable. Replit’s unacquirable. So being number two is great for venture. And the other thing in frothy times is they’ll pay up, too. They’ll pay 2 or 3 times what they would’ve paid otherwise.

So number two’s great when number one’s not available. Just don’t raise too much if you’re number two. Don’t make yourself unacquirable.

Can I push your thinking?

Yeah.

Is number one really unacquirable when Scale gets bought for $14.9 billion? Are we not seeing the limits pushed for what is acquirable and what is not?

Yeah, but it’s got to be a hyperscaler or someone to—

Agreed.

—but Workday can only pay so much, Harry. Workday cannot pay—

Right.

—$26 million to buy Glean.

No.

What’s Workday’s market cap today? It just doesn’t have the capital to make all the VCs what they want.

Agreed.

For sure, the hyperscalers can pay up, but also a lot of folks won’t sell at any price. And so being number two, just as founders, it’s a cheat code. Just don’t raise too much, be acquirable if you’re number two, be kind, and you’ll be shocked in frothy times by the offers you’ll get. You’ll be shocked by the offers you get being number two.

Have you ever regretted selling, both of you?

Yeah, a lot. You often do.

A friend of mine said to me this week, “Harry, I’ve never regretted selling and making millions of dollars.”

As a founder or VC, though? That’s a different question: as a founder versus a VC.

Yeah. He’s a VC.

As a founder, I would say more than 51% of founders regret it. I regret it. But as a VC, here’s the hubris in this: you’re going to tell a founder she or he can’t sell and expect them to work twice as hard after you tell them to F off? At the end of the day, unless you’re a total douche, if the founder wants to sell, you sell. It’s not your decision. That’s the height of hubris, in my experience.

Agreed, and I don’t think you even do tell them. I mean, you asked me if I regret it. There have been times when I look back and go, “Ooh, I think if we’d held, we would’ve compounded and been bigger.” And you have objective facts that make you believe that, which still isn’t the same as saying you regret selling.

In fact, in that particular case—and I’m choosing my words because it’s relevant to a dear friend of mine—I talked to the CEO 3 or 4 years later and said, “Oh, look, our competitor is now worth 4 times what we’re worth. Do you regret it?” And he wisely said, “No. I took money off the table. I bought a house. I got married. I’ve got kids. I’m wildly happy. I’m doing another deal. Here, you want to invest? Here are the terms. My life is great.”

As an objective matter of fact, you go, “Compounding would’ve been good in that case,” but it wasn’t to be, and I don’t regret it vehemently. I’m just like, “Yeah, but…” There are only a few where you look back and go, “There was a lot more compounding in it.” A lot of the time, you go, “Yep, that was a good call.”

And again, I think the more salient fact is this, Jason, right? It’s the founder’s call. So my MO is actually very different. My perspective is not to have an agenda one way or the other. The first thing I always say to founders is, “If the liquidity window opens as a private company, you should pause and take it seriously, because most of the time it’s not open.”

So the mere fact that it’s open means you have to pause and think. You have to change your game from being 90% heads-down, working hard, and now someone’s made an offer. It’s now time to get real and figure out—

Or do you not have to apply that same mindset as an investor?

You do, but I’m saying for the founder it’s more significant because it’s all or nothing. You can get it all off the table. And then you have the real conversation: How do you feel about things? As I always say to them, “Now would be a good time to voice any of those concerns that you’ve been suppressing deep in your sternum here, guys.”

Are you having active partnership discussions about much more liquid secondary markets and a trader mindset of maybe selling in a way that you wouldn’t have done years before because secondaries are available?

They are, but the truth is, I think they’re available for a small number of companies where they’re easily available at a discount. There’s a much larger number of companies where you have your winners and you look at it and go, “I don’t know if the market fully appreciates what this is worth yet. I think I’m probably a holder here.”

I have no reluctance to sell. It’s a little like the founder window opening. Everyone likes to talk about this, and LPs like to ask about this. But the truth is, the number of times that, as an individual investor, you’re in a company that’s so fricking amazing that there’s a free, liquid secondary market, where you’re in early enough to have a big enough hit to make a difference, is low.

If you have 1 of those per fund, you’re doing great. You probably have 3 or 4 winners per fund, and only 1 of those is kind of that super-marquee, amazing one. The people who bought in at $50 billion at Stripe aren’t looking to sell at $90 billion just because it’s liquid. Conversely, the people who bought in under $1 billion probably are and should.

So my point is this: yes, you have these conversations. It’s not like you spend most of the day out there trying to keep your $10 million ARR company going, help it get funded, and hope it doubles.

And that’s a new world. Getting those funded is harder than ever when they’re going from $10 million to $20 million.

Yeah.

But that’s an entirely new discussion.

Yeah.

9. The IPO Window Reopens

Speaking of moments of liquidity, IPOs: we had a $3.5 billion IPO for Via. We had Gemini go out at $4.4 billion and a 32% bump on the first day. And then we had Figure Technology raising close to $800 million in its IPO. Gosh, how exciting and nice to have IPOs again. Which do you think is most interesting to discuss out of those?

Well, can I add 1 thing, and Rory will know? The busiest IPO week since 2021 isn’t to be ignored or taken lightly.

Okay.

Now, it isn’t the busiest year yet. It could end up being the busiest year yet—I mean, it’s already September. Next year might be as big as 2021.

But if you’ve ever been a founder or worked at a company that’s decelerated, getting back to where you were is a big moment in time. You should celebrate when you get back. So last week, we were back to 2021 for a week. Maybe we’ll get there for a month, right? And then you get there for a year. It’s a big micro-milestone to have 1 week of 2021.

They’re all interesting for different reasons. I think Figure is the most interesting, just to start with that. Looking at those 3 IPOs, 2 of them are vaguely crypto-related: Figure and Gemini. 1 of them is a different SaaS company, primarily a SaaS company selling to governments around transport. It has a lot of complexity, and it’s not just SaaS. That understates the complexity of the Via business.

Of the 2 crypto companies, Gemini is the Winklevoss twins, of social-network repute, and Figure is Mike Cagney, who was the founder of SoFi. The first thing you note here is that these 3 IPOs—2 of them are kind of second-time founders, depending on how you adjudicate the Winklevoss case. The F. Scott Fitzgerald line that there are no second acts in American lives is wrong. These are 2 out of 3 second acts.

Cagney’s interesting because SoFi was an interesting company, very differentiated, and has gone on to be Chamath’s only successful SPAC and a perfectly great, successful public company. What Figure is doing is using the blockchain as a settlement mechanism for home equity loans and other kinds of nonconforming loans.

At heart, it’s a financial services company. It’s a fintech play. It’s lending money, which is 1 of the core things fintechs have done for 2,000 years. But its interesting twist is that it’s using the blockchain to process the back office more efficiently.

In the end, it’ll rise and fall based on credit. If you make bad loans, you lose money in the lending business. But there is an interesting twist around using the blockchain to instantly settle these loans and to be able to securitize them. There are some securities-law issues, but it’s an interesting company—a clever, good twist on blockchain.

First of all, yay, everyone: finally, a use for the freaking blockchain that’s standalone and independent of its being a trading asset. That’s what Mike Cagney’s done here. And all credit to him. It’s a good company. The stock popped nicely. Everything about that one, to me, is the most interesting.

Gemini popped high and then dropped down fast. It was fun. All 3 stocks behaved very differently. So even at the trivial level of the trading, Figure performed perfectly. Gemini popped way up and then intraday came way back down. Revenue’s declining on that one. It’s another crypto exchange. I never can tell them apart. It’s just not Coinbase and not, you know, whatever Binance is. So I don’t know why it matters.

Revenue’s declining, but God bless those guys. They’ve hung in a long time. And then, interestingly, from a stock-price-performance perspective, Via actually opened below its offer price and then bounced up during the course of the day, proving that it’s not always free money to buy at the IPO stock price.

But, yeah, fun week for stocks. Definitely, to me, Figure is the most like, “Ooh, that’s interesting. I’d like to learn more.”

The interesting question in the age of AI with Via Transportation, right, is that it was founded in 2012, so that’s 13 years.

Yeah.

Classic B2B plus. It’s not just SaaS, but B2B plus. $493 million invested, $4.2 billion valuation—

Yeah.

It will fluctuate. So, over 12 years, the investors in the aggregate 10Xed the total capital invested. That was an A+ but not S-tier investment until 18 months ago. Is it good enough today? Thirteen years, $500 million in, $4-point-something billion out. That was great until recently.

I would take it in a heartbeat.

Harry’s not sure. He’s not sure if he likes the fact that it has a defensible platform and big enterprise customers, or whether he wants to put more into Lovable. He’s just not sure which one he wants to do. They both have pros and cons. He’s doing both, actually.

I think at the end of the day, I’m thrilled to see IPO markets open. I’m thrilled to see exuberance. I’m aware that it will take 12 months for people to truly get cash back, but I’m an incredibly selfish, self-centered individual who wants LPs to have more money to put back into venture, and that will align perfectly with my fundraising cycles.

And so, inshallah, bring home some IPOs, previous generation, and fill up the LPs’ funding.

Good to know. And, yeah, it was a good week.

10. Bending Spoons Buys Vimeo

I was very excited for 1, though, which was Bending Spoons buying Vimeo. Bending—I mean, sorry, you Americans, you love to always claim dominance over European technology.

Yeah.

The European—the Italian—buying the public—

Cutting edge.

—American company for $1.38 billion.

First of all, stepping back, Bending Spoons is a quirky name, but a wildly successful buyout shop that specializes in these old assets that have some kind of brand recognition but no obvious model. The most obvious 1 is Evernote, which they bought and have streamlined, raised prices on, and, I believe, gotten to a more profitable business model.

So, yeah, I mean, it appears to be a probably successful formula.

The interesting thing for me is that they tend to buy assets very cheap, centralize, and just eke out the profits. Vimeo, I don’t know how cheap it is at $1.4 billion. StreamYard, they bought pretty cheap. Evernote, they bought pretty cheap. Eking out the profits was much easier.

At a $1.4 billion entry, you’re moving to a different scale of entry price. That’s a different game of roll-up.

I just have an emotional attachment to the brand. As a creator, I’ve been using Vimeo since the beginning, right? Since back when it competed with YouTube. So that’s a small portion of the business.

But it’s a $420 million business that’s basically flat. It’s an annuity. And they’re buying it for—then what?

Yes.

Three times revenue?

Yeah.

Less—2.5 times revenue. So either they have to make it more profitable, or they have to apply some folks who care more about software to inject a modest amount of growth at a time when Higgsfield and Gamma will do a third of their revenue in 12 months.

Inject a little of that Higgsfield and Gamma love, although I don’t know that they’ve made people use Evernote more—the Bending Spoons brothers.

11. Quick Fire Market Bets

Right, team, are we ready for a quick-fire?

Fire away.

This will be great. Rory, you’re going to love this, okay? We had the main man, Kaz, on the show. Opendoor today is sitting at about—I’m just going to check for accuracy—$9.30 a share today. Where is it going to be at the end of the year, December 31? It’s $9.30 today. Where’s it going to be?

Good God.

I’m pausing because Kaz seemed like a very nice man.

Oh, good God.

You got 24?

I got 24.

You got 24?

That’s my bet. My bet’s 24.

He just asked AI, Rory. Do you not know this?

No, no, no. I just did it the way I do venture investments. I just draw a line.

All right.

This is the beauty of being a late-seed investor. Early seed, you have to squint. Late seed, since the first investment, I just draw a line. It’s pretty much accurate.

Kaz is pretty damn good. The memers like him, as near as I can tell from Twitter. I’m going 24. I don’t know what the bet is exactly, but I got 24.

Rory?

I mean, somewhere between 9 and 24—in other words, I think it keeps going up. I think it’s an extraordinarily hard—

And I think this guy is so smart and keeps talent. They’ll make noise, move momentum, and I think in the near term the stock will appreciate because you can make the story feel big. I’m just going to say it: I think it’s a brutally hard business.

Over the next 3 to 5 years, you want to believe in that vision of being able to help people with the most important financial decision of their lives. I just think it’s an extraordinarily hard business because there’s a huge amount of arcane detail on every house, and everything’s a special snowflake.

So I hope I'm wrong because he seems like a great guy. I just think it's a hard thing to build massive enterprise value in.

Adobe is getting crushed by the markets, but the revenue is strong and continuing to increase. Will the share price be lower or higher in 12 months for Adobe?

Adobe's been growing—it's gone at 10%, 12%. The multiple went way up a year, a year and a half ago. I think they convinced themselves that having AI would be good for them or whatever, some amazing post-COVID story. They were obviously really high in '21. I want to say—I should know—40 or 5-ish PE, a high price-to-sales multiple. It dipped post-COVID in '22, and then it came back strong.

All that's happened now is it's reverted back to what it should be: 5 or 6 times revenue. It's wildly profitable and slow growth. They've done some things in AI, enough to not feel stupid, but not enough to actually move the needle significantly. So it's kind of valued just right. It hasn't crashed, it hasn't fallen. It's just that the euphoria has faded away, and now it's, I want to say, a 5- or 6-times-sales, 15-times-forward-P/E company. I think it's still vulnerable to medium-term disruption from AI, but I don't have an “Oh my God, it's crashing from here” view. It's just reverted to what it's probably worth.

Rory, higher or lower?

Logically, my answer to the question has to be no more than 10% higher, because if it grows 10% in sales, it should be 10% higher if it's fairly valued today. But I feel it's a low-confidence comment. The salient point is your narrative, and I've seen the narrative on Twitter: “Oh my God, Adobe's crashing.” The real narrative is Adobe's returned to Earth. Jason hates that, I think.

I don't think you believe that the stock price doesn't assume a certain amount of forward growth in its current stock price. I don't believe you believe that.

Yeah. I think it's been growing—

You don't like the calc sheet. Fair enough. You don't like it. I'm betting short- to mid-term down at least 10%. Two reasons. One, Scott Belsky leaving is a bad sign for AI at Adobe.

The guy is not 70, okay? He's still got the fire. He goes off to be more creative. Give him a couple hundred million like Kaz. Getting Scott to leave was a big blow. Listen, maybe behind the scenes, I'm exaggerating his influence, but I've worked with a lot of the folks that are still executives today. It's a big loss for Adobe, losing him in AI, and maybe he came up short of what he wanted to accomplish, right? It's a big company, a lot of ships to move.

Yeah.

But you're just at a loss without him.

Yeah.

Two, this is my biggest tell of being worried about public companies today, okay? This is my least favorite metric, even worse than Google's margin—I mean, Oracle's margins on its cloud services. AI-influenced ARR. Adobe announces 5 billion—

Oh.

—of AI-influenced ARR.

Oh, God.

You don't have to say this if you have AI ARR. “AI-influenced ARR.” To me, any public company quoting billions of AI-influenced ARR does not believe they will have billions of real ARR. I just think both are a bad sign at the margin, but this is a business that can't be killed, right? It is an enduring business.

Listening to you, Jason, you could be right. There could be a little more deflation in it. It's not going away, but it's 10% growth. It's slowing down. In retrospect, the real question is, how the hell did people think less than 2 years ago that it was worth 18 times revenues when it's worth 6 times today, right? I mean, what were people smoking?

Yeah. A lot of Adobe's history is financial engineering and the move to the cloud, and they got a lot of run out of that, right?

Yes, they did.

In the end, Scott wanted to buy Figma. It didn't happen, and he left.

They did at least try. They weren't left.

They tried. They tried.

But yes, just think: if they'd bought it, you'd be getting those little pop-ups from Figma too, telling you, “You've used up your license for Figma Adobe Cloud. Please pay $79.99 for the next 12 months.” I find the Adobe product to be the most annoying and least understandable set of licensed products out there, right? They harass me.

It's because Jason's not there, Rory.

It's because Jason's not there.

Well, it is because what happens is, you sit in a conference room with spreadsheets—

Yeah.

—right?

Yeah.

At 11% growth, Salesforce is probably getting the majority of its growth from price increases today.

Yes. Agreed.

It's hard to parse the numbers, but my rough view of Salesforce, with 6% to 7% annual price increases on average and growing 9%, is that you can't trace it perfectly. Maybe Rory can, but I'm assuming the majority of Salesforce's growth is from price increases.

And you're sitting at Adobe at 11%, and you can figure out how to get people to accidentally prepay for 3 years or confuse monthly for annual.

Oh, I agree.

That could give you hundreds of millions of dollars of revenue, right? And they don't care about the cash. They care about the GAAP-recognized revenue. So they want to lock you in for life at the highest price, and those meetings do happen, and they last days. They last days on those things. It is not just one product manager going amok.

I actually think this is an interesting discussion for the last minute here, because you're right, Jason. It's $23 billion in revenue. That's roughly right. And if you compare the Wix thing, if you don't think AI fundamentally threatens your business here, you're delusional. It's what we discussed earlier: you're going from a small number of professional creators to an infinitely large number of amateur creators. You've already allowed Canva and Figma to get under your skin, and now you have a whole next generation coming up.

What do you do that's aggressive enough to move the needle here? Because for Wix, I don't know, doing $1 billion or $2 billion in revenue, a $100 million revenue acquisition is somewhat meaningful. What do you do if you're Adobe, and what do you buy in AI now that you can't buy Figma pre-AI? And how do you think about the threat here? I mean, they've announced some products, but it just doesn't appear to have landed.

One of the areas we've been looking at a lot is that area of next-generation creative tools. And you know what? For a while there, I was like, maybe Adobe will land some punches and be relevant. They were talking the right game, but they don't appear to have done so.

Yeah, but Jeff Lawson made the great point, which is obvious, but I think Adobe's in this trap: you can't cannibalize your seats.

Yes.

Adobe wants to add Firefly and AI to your expensive suite, and Microsoft is half giving up on getting people to buy AI Copilot for Office. But what we really want is not even to buy those seats. I don't have to buy a seat with Higgs Field or with Reeve or with Gamma. I don't have to buy a seat at all, right? Or it's just 1 seat, right?

To Kaz's point with Shopify, I only need 1 seat to run my whole freaking store, right? And so we love the seat, man, but it's tough in the age of AI because you don't want to cannibalize your seat. Jeff's right. It's a tough one for Adobe, right?

Guys, this has been fantastic. The joy for me is like you can see the progression of every show, actually, I think. This has been amazing. Thank you so much as always.

Rock and roll.

Now, I want those shows to be the best shows that you listen to every week. So I want your feedback. Let me know what we can do to make them better. Any guests that you'd really like us to have on, I want to hear your thoughts. Harry@20vc.com. But before we leave you today, let's talk about agents, specifically Piper, the AI SDR agent brought to you by Qualified. The agentic marketing era has arrived. And if you're a B2B marketing leader looking to scale a pipeline generation Piper, the AI SDR agent, wow, it is here to help. Piper is the number one AI SDR agent on the market according to G2. And hundreds of companies like Box, Asana, and Brex have hired Piper to autonomously grow inbound pipeline. Fucking sign me up. Anyway, Qualified customers see massive business impact with Piper. Three X increase in meetings booked and two X increase in pipeline. Wow, that is some results. Hire Piper, the number one AI SDR agent, and grow your pipeline today. Learn more at qualified.com/20vc. That's qualified.com/20vc with the 20 VC spelt out in letters for goodness sake. And while Piper builds your pipeline, HubSpot gives your business the AI tools to scale faster. Think about listening to this podcast right now. You're probably multitasking and catching 70, maybe 80% of it. How dare you? This voice is so captivating. Now flip that and imagine catching only 20%. That'd be pretty crazy, right? Yet most businesses only use 20% of their data. All the important details in cool logs and emails, in chats, they're just left floating in digital space. Well, HubSpot gives you access to those insights to help you grow your business because when you know more, you grow more. Visit hubspot.com to get the full picture today. HubSpot keeps your CRM humming, and when you layer in AI, Nexos takes it to a whole new level. Who's the biggest AI threat to your business? It might be your own employees. They use unsanctioned AI tools and personal accounts for work tasks and feed company data to places honestly it just shouldn't go. Well, this is what we call shadow AI, and it could cost you millions. IBM found that 97% of organizations reported an AI security breach that's in 2025 alone. As a CTO, a CIO, or a head of AI, that's a mistake you just can't afford. Nexos.ai fixes it with an all-in-one secure AI platform. Nexos.ai stops shadow AI in its tracks, so it's a unified platform for secure company-wide AI adoption and productivity. Tech leaders set policies and oversee usage. Business teams get the models they actually need. Try it yourself with a 14-day free trial at nexos.ai/20vc. As always, I so appreciate all your support, and stay tuned for an incredible episode with Jesse at Decagon tomorrow

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