Speaker 0
The people who said, “Oh, the $3 billion on the table,” the $98 price only happened because the IPO happened at $38. It’s exactly what you said, Harry. The discussion they were having on the day was, let’s call it the Halligan discussion: do I go $2 more and exclude Fidelity, or $2 less and take Fidelity? Had someone walked in and said, “I know this IPO is gonna price at $100 a share to open tomorrow morning. Let’s raise it to $80,” they wouldn’t have had a book because no one had bid at that price. So that money wasn’t accessible.
Speaker 1
Run, Forrest, run. The market’s wide open. The valuations are good. There’s a lot of demand. It’s very seasonal. If I were Canva—it’s an amazing company—I would be lining everything up to go public.
Speaker 0
The people who said, “Oh, the $3 billion on the table,” the $98 price only happened because the IPO happened at $38. It’s exactly what you said, Harry. The discussion they were having on the day was, let’s call it the Halligan discussion of do I go $2 more and exclude Fidelity, or $2 less and take Fidelity? Had someone walked in and said, “I know this IPO is gonna price at $100 a share to open tomorrow morning. Let’s raise it $80,” they wouldn’t have had a book because no one has bid at that thing. So that money wasn’t accessible.
Speaker 1
Run Forest, run. The market’s wide open. The valuations are good. There’s a lot of demand. It’s very seasonal. If I were Canva, it’s an amazing company, I would be lining everything up to go public.
Speaker 2
This is 20VC with me, Harry Stebbings, and it’s my favorite show of the week. Jason Lemkin, Rory O’Driscoll, and we have our first VIP guest. We have Brian Halligan, founder of HubSpot, joining us. Honestly, today we shoot the shit breaking down Figma. What happened? Was it the greatest mispricing in history? We then discuss Meta and Microsoft’s blowout quarters, what it means for them moving forward. This was so much fun to do. 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. You want to grow your company, right? But instead of having the time to get to the next level, you’re stuck maintaining the status quo. It’s freaking maddening. Well, HubSpot’s customer platform, it actually solves this. Breeze. No, it is not a fabric refreshener. This is the next generation. Their built-in AI takes over all the busy work. It writes emails. It qualifies leads. It answers common customer questions and even help create content. Also, your marketing, your sales, your service teams can focus on what matters most. And the impact is undeniable. Teams are saving 750 hours a week. One even increased leads by 251%. And these results show up in days, not months. Over 238,000 businesses already use HubSpot, so join them. Visit hubspot.com/ai.
Speaker 0
You have now arrived at your destination.
Speaker 2
Guys, I am so excited for this. You know it’s always the highlight of my week, and we have a special guest this week in Brian. I mean, it’s gonna be better than ever. We’re just gonna start and dive in with the Figma IPO. We saw the most unbelievable mispricing. It went out at $33. It went up to around $145. I would like to throw this out there to some of the greatest minds in this business: how did we analyze this unbelievable pop?
Speaker 1
What was—I should know—what was it at HubSpot, Brian? There must have been a pop, right? We had a pop. HubSpot was—
Speaker 0
You priced at $25, and you opened around $30.
Speaker 1
Yeah.
Speaker 2
We priced at $25. I think we opened at $33.
Speaker 0
Yeah.
Speaker 1
It might be worth just talking about what happens behind the scenes on this shit.
Speaker 2
Yeah, everyone’s talking out of their asses on X, aren’t they?
Speaker 1
Yeah.
Speaker 2
Like they know everything.
Speaker 1
Yes. I don’t know everything, but I can share what actually happens and how you make that decision, and what the pressures are.
1. How IPO Pricing Works
First of all, you’re making the decision on the price and who the investors are going to be the night before the IPO. At this stage, you have never been as tired in your entire life as you are when you’re making this decision. You’ve been on the road for the last 2 weeks. You’ve hit 12 countries. You’ve had 6 pitches a day. Your battery is in the red. You’re tired.
Then the investment bankers sit you down and say, “You’ve got 2 big decisions to make. One is, who are the investors going to be? Who are we picking?” Because we were 27× oversubscribed. You know, Figma was 40× oversubscribed. Who are they gonna be? And then, what’s the price?
For the whole process, the founders are very well aligned. We had Morgan Stanley, as well as the investors, all perfectly well aligned until this 1-hour meeting the night before pricing. Then, all of a sudden, you’re across the table from them. The first thing you’re across the table from is the book of all the people who want to buy your stock. Again, there’s 27 times more demand than you have supply.
In their version of the book, they have a lot of their hedge fund buddies in there with pretty good allocations. And we also have some of the, quote-unquote, “long-only” funds—we can talk about that, too—including Fidelity, Wellington, and Capital Euro. What HubSpot wants is just the long-onlys. You want to keep the hedge funds out. Morgan Stanley wants that, too. They want to keep them happy, but they also want their hedge fund buddies in there because they make a lot of money there. So that’s a negotiation, trying to get all that, squish the hedge funds down, and get the long-onlys up.
Then it’s the price. In HubSpot’s case, it was a very interesting dynamic. We had raised the range throughout the roadshow over the previous 2 weeks. We wanted to go out at $25. Morgan Stanley said we should go out at $24, and the reason we should go out at $24 is that Fidelity had told us they were in at $24 and out at $25. You really want Fidelity because Fidelity has trillions of dollars, and they could own a massive anchor position.
So then you have a debate in your head: how badly do you want Fidelity? How much do you wanna sell for? We were oversubscribed, and we thought, “I think Fidelity’s gonna come in anyway. It’s a really good thing. I think they’ll come in. We’re gonna stick with $25.” So we pushed back, said no, and priced it at $25.
I don’t think there was collusion going on, but definitely Morgan Stanley and Fidelity were on the same side of the table, trying to get us to sell at a lower price. That’s kinda how it happened behind the scenes. And then I can talk about the next day and how it all develops.
Speaker 3
So there are these micro-conflicts, but they rear their heads at the last minute in particular, right? At the last minute, they rear their heads.
Speaker 1
Yeah.
Speaker 3
At the last minute, they rear their heads.
Speaker 1
It’s really just at the very last minute. It’s fine. And by the way, there’s a lot of talk around the pricing and it pops so much. Whose fault is it? Morgan Stanley’s fault? The founders make the decision on what the price is, so Dylan decided at the end of the day.
2. Why Figma Popped So Much
And by the way, if you’re Dylan and you’re Figma, you had a very limited amount of shares that were selling. They were mostly secondary, so there were very few shares to sell and a lot of demand for them. And if you’re Dylan, that’s gonna drive the price up.
The second thing is, here’s who you really want: you want Fidelity, you want T. Rowe Price, you want Wellington, you want Capital Group. There are about 6 big long-only funds you want in there, and they’re pissed because they’re not getting a big allocation. So that created the demand environment that was a little tricky for them because they wanted to buy more shares, and that’s what pushes the price way up.
The supply is low, and the demand is very high. But it’s an interesting little game of chicken. You play chicken with your investment bankers and some of the long-onlys. It’s like 7:00 the night before the IPO.
Speaker 3
But there’s no one dumb at Figma. This is the other thing about social media. You think Dylan and his whole finance team and CFO have never heard of these issues before? Everyone’s trying to weigh everything and come out with the optimal outcome, right? No one massively mistakenly underpriced this deal, did they? We’re not talking about rookies here, are we?
Speaker 1
I don’t think so. I think there were a lot of smart people around the table giving them advice, and they wanted to make their investors happy.
Part of it also is that you want a pop. You want Fidelity, T. Rowe, and these long-only folks to come in and, right out of the gate, feel good about their investment. You want them to hold for decades and decades and decades, so there’s a little bit of that. It probably just popped more than he thought.
Speaker 0
And that’s the exact sentence, right? Until that, Brian, everything Brian said is correct. And the stunning thing is, they clearly give the same speech every time because I’ve been in the room, I think, 5 or 6 times, and they give the same speech. It’s always Fidelity or one of the other two. It’s like, “You want Fidelity. It’s only another dollar.”
That whole speech is exactly right, and you want a little pop. The interesting thing that Brian said at the end was that, instead of getting, let’s call it, the designed 15–20% pop that makes everyone feel good, you ended up with this absurd 250% pop, which is clearly off the charts. I mean, I think it’s the largest pop since 1999.
So what you’re really saying is, you’re trying to engineer this small explosion, and then every once in a while, inadvertently, you create a big explosion and you look like an idiot.
Harry Stebbings
So the question is, are we arguing about whether we need small explosions, which happen all the time? In other words, the classic HubSpot 20% pop. Is that a problem or not? And that's all about a $1 discussion with Fidelity. Then there's the separate problem of when you get it massively wrong: what causes that? I think you should talk about them separately, because they're almost 2 separate issues. Does that make sense?
Speaker 3
There's one small thing I heard nobody talk about on X on this. At my first startup job, they gave me the job, and this is the only IPO I'll ever go through as an employee. They gave me the job of handling the direct shares program. It was my job to hand them to only the employees, not the external ones.
I went around, and there was a lot of drama because people had to come up with $50,000, $60,000, $70,000 to buy their stock. This was not a lot for folks who had no secondaries. There was no secondary. Everyone in the company basically made $100,000 that day, and it was a magical thing. Now, was it underpriced? But we forget about the employees. Employees don't care about dilution; they don't even know what dilution is. All they care about is what happens with their stock. It was a magical moment for the employees. Whether it was mispriced is a different issue, but no one's talked about that transfer. It may be a small issue, but employees may not care.
Speaker 0
Yeah.
Harry Stebbings
I guess a cool question for me is, do we think it was fundamentally mispriced excessively, or is this actually just IPO exuberance on an asset that is good with a great-quality founder? Is it not dramatically overpriced at the $137 that it hit?
Speaker 0
Agreed, and that's actually the next shoe to drop. You're exactly right. The whole 20% pop discussion is an interesting one, and maybe Fidelity, to Brian's example, would've bought at $24 or $25, and they probably bought more at $30. That's kind of in the bounded range.
I can tell you right now, the people who said, “Oh, $3 billion on the table because they could have gotten $95 a share,” are talking out of their ass. I can guarantee you the order book. What did it price at? $35, $38, whatever it was. There was some at $38, some at $39, and some at $40. No one was putting in an order at $98.
So what happened—and this is a bit existential, metaphysical maybe, so go with it—is that the $98 price only happened because the IPO happened at $38. It's exactly what you said, Harry. The discussion they were having on the day was, let's call it the Halligan discussion: do I go $2 more and exclude Fidelity, or $2 less and take Fidelity? It's a good, useful discussion.
Had someone walked in and said, “I know this IPO is going to price at $100 a share to open tomorrow morning. Let's raise it to $80,” they wouldn't have had a book, because no one had bid at that price. So that money wasn't accessible. All that happened here was, as you say, I think a little bit of it was that maybe they could have gotten a couple of extra bucks, and maybe that might have slightly dampened demand.
But really, what you're saying, Harry, is what? Correct. There was some pent-up euphoria on the retail side, and they all rushed in. I can tell you why it's not successful, going back to Brian's example. This is a really sad comment, but it's true: if you have a 20% pop and you get in Fidelity at $25, they'll buy more at $32.
Let me give you a really sad fact, and I didn't realize this at first. All those big buyers who came into Figma at $38 have an internal process with a price target to exit before they buy. None of those price targets are going to be more than $110 a share. Unfortunately, because you underpriced it—I won't say underpriced it, because it's now trading at a price that's probably above the long-term price target of the long-term investors you want—most of them are selling those shares right now.
I used to think, “Oh my God, they'll hold because they know it long term.” But if you're running money as one of these institutions and you bought at $35 and built a business case that said, “We think this will be worth $50 a share in 2 years,” and suddenly it's worth $100 a share in 2 days, at least half of those mutual funds have to say, “Should we lose our position?” My guess is they will.
Speaker 1
People say long-only. They're not long-only. They do sell. They come in and out of HubSpot. I see them coming in and out. I think they're trying to build a position. They only floated a tiny amount here, so I think they're like, “Okay, we're in there. We got a toehold. We're going to hold for the long haul. We think this is substantial.” I doubt they sold. I think it's Harry Stebbings who sold. I think it's hedge funds that sold.
Speaker 0
I think you're definitely right on the hedges. No one on the hedge side is out or is in.
Speaker 1
I doubt the big long-onlys, quote-unquote long-onlys, sold. Can I tell you guys another story about this whole thing? First of all, before HubSpot went public, we did something called a non-deal roadshow with Morgan Stanley. We met all the big investors. All of the big investors we met came in big on our IPO. The ones we missed, we couldn't convince to come in on the IPO.
For us, we missed T. Rowe Price. It's down in Baltimore. We didn't want to go down to Baltimore. We missed Capital Group in Southern California. It just didn't quite hit. It was a long trip. We missed both of those in the IPO, and it took a good 3 or 4 years before we got T. Rowe Price and Capital Group in and could convince them this was a good company that was going to be able to go the long haul. You want those guys in there, and you want to make it a strong incentive to get them in right out of the bat, or you might not get them for a while.
Speaker 3
And meet them in person, it sounds like. It's costly.
Speaker 1
So the non-deal roadshow is key.
Speaker 0
It's also proof of the old rule: you always remember the people you didn't get, no matter how long. All of us have been fundraising. You can vividly remember every no. You can vividly remember every, “I didn't go and see him when I should have.”
Harry Stebbings
Do you think we overestimate the importance of having Fidelity in?
Speaker 1
I think it's important.
Speaker 3
Yeah.
Speaker 1
And Fidelity—
Speaker 3
No.
Speaker 1
Fidelity and T. Rowe Price own a huge chunk of HubSpot now. Wellington Capital owns very large chunks of HubSpot, and they're pretty stable. They come in, trim on the edges, and come in and out.
Most people think consumers own a lot of the stock, that retail investors own a lot of stock. Very little of HubSpot is owned by mom and pop—by Harry Stebbings buying it or Harry Stebbings' mom. It's like 90% of it is owned by these big institutional investors.
Harry Stebbings
Brian, you never gave me access to the pop. I would've been there, dude.
Speaker 0
For the record, Harry, I think you were 12 at the time, and I'm not even sure you could legally own stock, big guy.
Harry Stebbings
Dude, I was totally underage. The one thing that I do think is that if we're Dylan now at Figma, are we thinking, “You know what? I wish I'd done a direct listing”? Does this make direct listings much more attractive, and would this have solved the problems that we've seen?
3. Would Direct Listing Solve It
Speaker 0
Again, I'm going to push. When you send out the questions, I did more reading on this than I have in a while, and one thing I didn't realize is that the SEC has amended the rules, so you can now raise capital on a direct listing. It is possible. I think Amplitude did it.
But—and this is the big but, and this is why I said it gets kind of weird—if you did a direct listing, I don't think you would've direct-listed at $100 a share. It might've been $39 or $40. The weird thing is—and how to put this?—I'll say that it may well be that these random, weird pops every once in a while are just a natural phenomenon, like earthquakes. They just randomly happen.
Because it's not as if, if you did a direct listing, people would've said, “Yeah, I think I should pay 80 times one-year revenues for this puppy.” It would've been the same analysis at 15 times or 20 times one-year revenues: $35, maybe $38. You might've captured the $2 or $3 extra dollars that you left on the table in return for getting Fidelity in, and then you would have the Brian CEO comment of, “Is Fidelity worth $3 extra bucks?”
But what you would not have done is place the stock at the lofty level it is now. It may well be that mega-pops are a natural, intermittent consequence of the IPO process, and that a direct listing doesn't solve that part of the problem. Was that as clear? Because it's kind of weird. What you're basically saying is it's almost like a psychological phenomenon. I'll give you an example in venture of the same thing. We're seeing it now.
Harry Stebbings
I get you, but it's not, though, because you've got Circle, you've got CoreWeave, and you've now actually had 3 in the space of 2 to 3 months.
Speaker 0
I think it's timing in the market, and you had a similar thing in '99. I think it's a once-in-a-while phenomenon, when conditions are adjusting from one more pessimistic stage, which we were in during April. Remember how up our ass we were in April? It's only July or August.
When people are adjusting, maybe we just don't adjust quickly enough, and the euphoria comes after the stock gets priced and starts trading. There's a small number of highly speculative assets, and there's a lot of appetite for those assets, and they all just rush in.
Harry Stebbings
It’s like the venture equivalent we’re seeing now. We’re seeing it now when someone with a really big brand name does a round. Six weeks later, many of these companies are doing a follow-on round. Nothing’s changed. Everyone bid 120, the brand name won, and six weeks later, there’s a bunch of people doing it at 350. Why? Well, the brand name is in. This is kind of the public-market equivalent of FOMO. That’s how FOMO manifests.
Speaker 1
I think the direct listing is like you’re a little bit scared you’re not gonna get those long-onlys. You’re not gonna properly market it to them. And it’s 7% to the bankers. In the grand scheme of things, it’s not that much. I think it’s risky unless you’re Google or Facebook. And just to pile on what Rory said, timing really matters. HubSpot went out. Three months before HubSpot went out, a kind of sister company of ours, Zendesk at the time, went out.
Speaker 3
Yeah.
Speaker 1
It was timing, and it was just a shaky week that they went out, and they just didn’t get the big long-onlys. They had a good story, and they didn’t get them.
Speaker 3
Yep.
Speaker 1
And they never really got them. They always had a lot of hedge funds in there, and they always had a lot of individuals in there.
Speaker 3
Individuals.
Speaker 1
Our timing was pretty good. Not great, but pretty good, and Figma’s timing was obviously really good.
Speaker 3
Harry, I think that’s super interesting because Zendesk is kind of a tough tale, right? I don’t think Nickel wanted to sell. He turned it down at whatever, $20 billion, and had to sell at $10 billion. I mean, $10 billion—these are still good numbers. But it was a reluctant seller, right? And maybe—and, to Brian, I hadn’t realized this—maybe part of it was never getting that buffer in, right? Assuming they held, right?
Speaker 0
He had a weird cap table.
Speaker 3
Never getting that buffer in at the IPO, right? And then you’re just—it’s horrible to deal with these activist investors, right?
Speaker 0
It is.
Speaker 3
It is. It’s a terrible experience as a founder.
Speaker 0
I’m going to come in here only because it won’t be obvious to everyone listening what happened there, because I’d never heard that point before, Brian, and I remember both IPOs as well. What you’re basically saying is you guys and Zendesk, I want to say, priced in 2013, 2014-ish—I can’t remember. And then what you’re saying is, because of the way your deal came together, you got the long-onlys day 1. Zendesk didn’t. They priced, I remember, three months earlier, and the VCs had to put money in the round; it was so tough.
Speaker 1
Yeah.
Harry Stebbings
What you’re saying is, 5 or 6 years later, they still didn’t have quite a strong investor base, and when they hit an issue and had activist pressure, it’s probably not the only thing that caused them to have to sell.
Speaker 1
Yeah.
Speaker 0
But at the margin, you had a stronger investor base the whole way through, and that’s your argument for giving up a buck and getting Fidelity.
Speaker 1
Most of that stronger cap table was more luck than skill. The Mikkel story, my story—the end of the story really rhymed.
Speaker 0
Yeah. I remember—
Speaker 1
Our timing was better. We had a better cap table. Having a good cap table is underrated.
Speaker 3
That’s why you should take money from me, Jason, and Rory.
Speaker 1
No way.
Speaker 3
That’s what we tell founders.
Speaker 1
By the way, while we’re talking about this, just the inside baseball of the whole thing: That night, you’re exhausted. You’ve never been tireder, and my co-founder is really introverted. He was negative energy because you spend so much time with humans. And then that night, you have a big fucking party with all your execs. You’re so tired, the last thing you want to do is go to—
Speaker 0
No.
Speaker 1
By the way, inevitably, somebody gets wasted at the party. It’s not the founders—
Speaker 0
No.
Speaker 1
Somebody gets wasted at the party, so it’s like a big thing. And then the next morning, the inside baseball is we did New York. And the next morning, you have a big dinner, and then you’re up on that platform.
Harry Stebbings
I know.
Speaker 1
And there’s this huge discussion about who’s on the platform, who made the platform and who didn’t make the platform, and who’s deciding who’s on the platform, which is another thing Dylan was dealing with, which is super irritating. He probably dealt with it a couple weeks before. Do the VCs make it onto the platform, for example? So that’s going on.
Speaker 3
Very, very important to the VCs to be up there, right?
Speaker 1
Yeah. Very.
Speaker 3
You don’t want to take your picture staring at the big drape of Figma outside Wall Street. That’s pretty embarrassing, that one on X.
Speaker 1
Okay. Just a pro tip for the listeners who are eventually going to go public: We’re on the platform, it opens, and everyone on the floor is up there looking at you on the platform. Most companies just kind of sit there like… And then everyone down below is like, “Oh, they’re so boring.” So you have to have a plan to do something interesting when you’re up there—
Harry Stebbings
Yes.
Speaker 1
—to get the floor excited, to get the press excited. That’s one thing. So then the market opens, and in my head I thought, “Well, we’re trading. That’s it.” But what happens in Figma, what happens in HubSpot, all these—
Harry Stebbings
2 hours later.
Speaker 1
It takes about 2 hours for the first price to settle in. And so you and your executive team, and maybe your VCs, are all sitting there extremely awkwardly on the floor of the New York Stock Exchange, looking at a million monitors, and you’re not trading yet. It takes a couple hours for the darn price to settle in. It took HubSpot 6 hours, and it finally settles in, and so it’s like, “Okay. Okay. It’s $33. Great.”
I remember that moment because my co-founder, Dharmesh Shah, who’s a prince, had the stock app and showed it to me. He’s like, “Brian, look, we’re worth $1 billion.” And I remember I said, “Take a screenshot. We’ll never see that again.” We were so excited. That’s the behind-the-scenes on the floor.
By the way, the other pro tip is you can do Nasdaq or the New York Stock Exchange. They’re virtually exactly the same, except at the New York Stock Exchange, you get to ring the bell. That’s why we picked the New York Stock Exchange.
Harry Stebbings
We did one in COVID where you get to ring it, but in an empty TV room. It was kind of very soulless. You’re pretending to be excited.
And the whole point of the dinner, remember, the dinner comes right after the pricing committee. So my mental model on the dinner is the bankers have just screwed you over for a buck a share, and in return, they buy you a very expensive dinner and liquor you up so you forget.
It’s totally discordant because you’ve literally come, as Brian said, from a very angry meeting where these people who’ve been your friends for 2 weeks on the road, carried your bags, done everything for you, suddenly start picking your pocket and telling you that they’ve got to give money to their friends. It’s controversial, and you argue. And then at the end, you walk away and go back, and then you all get plied with liquor by them, right?
And remember, this is the information asymmetry. 1 day later, you drive out of town, and they bring in the next group of their best friends, and the next lamb is led into the slaughter, baby. And that’s the deal. But it works. I mean, where else in the world are you gonna get a couple of billion dollars for 2 weeks’ work?
Speaker 1
In Silicon Valley, you get it every day. That’s happening now.
Harry Stebbings
Well, this is true. This is true.
Speaker 3
Brian, can I ask you one meta question on this? I think I know the answer, but when you look at the Bill Gurley criticism of all of this, one is all the money left on the table, right? That’s the math. But I think underlying that also is dilution. Most early-stage investors—as investors, not as founders, because I’ll ask my question—dilution does creep up on you, right?
As a founder who’s gone through this journey, did you ever sweat any of this dilution—the IPO dilution, the post-IPO dilution?
Harry Stebbings
Look at that face.
Speaker 3
Did it even come into your calculation, or did you just not care?
Speaker 1
My net worth went from X to 100X. I would just not care.
Harry Stebbings
And that sentence is why this process is so hard to change. The profound truth, as Brian said, is you’re doing this once and it’s the most important thing in your life, and these guys are doing it every day and they know so much more than you. It’s a really hard process to reform. It’s one of those ahas.
4. CEO Compensation Is Broken
Speaker 2
I do want to stick on that. You said your net worth went from X to 100X. I think an element that we chatted about, texted about before, Brian, that not enough people are talking about is actually the package that’s in place also for Dylan, which is obviously this $2 billion moonshot-like grant, Elon Musk-style.
Brian, we were saying that we don’t talk enough about CEO comp. Why don’t we start with you, Brian, on this, given you’re the best person here to speak about it? How do you think about this, and how do you analyze that?
Speaker 1
Yeah, I think CEO comp is pretty broken at the moment, and there are 2 things that I think are pretty broken about it. The first is just everyone really relies heavily on RSUs.
When I grew up in the industry—I hate to say, “Back in the old days”—it was mostly ISOs. It was options. Until 2006, some regulations changed and the expensing of that changed, so the world kind of moved to RSUs.
It just creates a risk-averse behavior in the CEO. It’s basically cash compensation: it goes up and down a little bit, let’s say. But with ISOs, you’re swinging for the fences. You’ve got a strong incentive to swing, and so it’s really had a dampening effect on the risk-seeking behavior of a CEO that I think more companies should want. It’s pervasive across the industry, so I don’t like this RSU comp thing. That’s the first problem I see with all this stuff.
The other problem with comp is that almost every company looks to CEO comp, and the way it works behind the scenes is, HubSpot’s got a compensation committee, everyone’s got a compensation committee, and HubSpot wants to pay the CEO, let’s say, at the 75th percentile of what her peers make. So we look at 20 different peers of similar-size companies—Atlassian, blah, blah, blah, blah—and peg her at the 75th percentile. In her case, it’s $20 million, a lot of money.
Now, if you did that for Dylan, which would be in our comp group, similar market cap to HubSpot, he’d make $20 million a year. But if you think about it, that’s 0.3% of Dylan’s market cap, of his own personal net worth. It doesn’t move the needle an iota. It doesn’t matter at all to him.
And so you have to get creative. I actually like what they did with his comp. They used PSUs very heavily, not RSUs, and I like the idea of not pegging your comp to your peers, but you kind of have to peg the comp to the net worth. Same thing with Elon Musk. If you paid Elon Musk like Mary Barra—Mary Barra makes $29 million a year—do you think Elon cares about $29 million a year? So you have to kind of comp it to the CEO’s net worth as opposed to just the peers. That’s what I like about this.
Speaker 0
Harry, you were going to come in, and I’ll just save you the trouble. An RSU is like an option but with a 0 strike price, so it’s guaranteed money, and Brian’s right on all the negatives there. PSUs, or performance stock units, have evolved to effectively make the RSU more like an option because what you say is, “It’s guaranteed money, but only if something happens.”
The typical thing that people are pegging it to in the public markets, even though I don’t agree—and I’ll come back to it—is stock price. In other words, instead of saying, “Here’s 10,000 shares no matter what,” it’s, “Here’s 10,000 shares, but you only get them if the stock price is $40.” So what you’ve bizarrely done is recreate options because they got regulated out of existence in 2006. Now you’ve effectively recreated them. So the PSU is making an RSU more like a stock option.
Speaker 1
I like that.
Speaker 0
I know. And in general, I do too, but watch this. The problem with the Dylan comp package—I’m going to say it didn’t work—is that if you look at it, the problem with stock-price triggers for compensation is that it sounds rational, but they put this in place before the IPO, and if you read the triggers, they’ve already achieved them. I’ll tell you why they do that in a second, but the weird thing about all these triggers is that effectively it said you’ve got a whole bunch of price tags up to $118 a share, I think.
Probably when they were making those triggers, literally 2 months ago, they were like, “Yeah, this is going to be great for the next 3 years.” But totally out of Dylan’s control, just because of the way things have priced, he’s made all the triggers already. So, in retrospect—
Speaker 3
Well, he did build the company.
Speaker 0
He still has to vest over 7 years, so it’s not like he takes all the money and runs. But the performance element vanished very quickly because of the pop.
The aha for me is that I prefer performance-based to not performance-based. I would have preferred, even for a public company, to do them on tangible goals—revenue and op income and all that—over multiple years. I see Brian shaking his head. The problem, and the reason you don’t end up doing that, is because, A, you have to disclose them, and B, things change.
When you change comp on a public company, the ISS and all the whiny babies give you a whole lot of shit. What happens—and I’ve been in the room—is that you say yourself, “I would love to pay Brian Halligan for 35% revenue growth and 35% EPS growth for the next 7 years, and we’d pay him $1 billion.” But if we put that on the table and circumstances change, we have to disclose it. So then all the analysts will start saying, “Oh my God, they think they can make 35%.” If they only do 30% growth, Brian missed.
So it just becomes problematic. What they do in the end is say, “Screw it, we’ll just do stock-price targets.” They’re better than nothing, as Brian says, because it’s more swing-for-the-fences, but sometimes you have this weird situation. If you look at all these packages that were put in place, the ones that were put in place in 2018 worked and gave the CEO what they wanted because the stock price went up, and all the ones that were put in place in 2021 are stranded because all those price targets, like the Airbnb price targets, ain’t ever going to happen now. So it’s an imperfect mechanism, as comp often is, but directionally the right approach.
Speaker 1
I am not in violent disagreement with what you’re saying.
Speaker 0
Yeah.
Speaker 1
PSUs—the way HubSpot does it—is on net new ARR and a floor earnings number. By the way, none of this is like, “What’s the least bad you can do?” And I like the way we ended up on it.
Speaker 0
That is really nice. Do you guys do—I’m curious, and you have to disclose that—do you get angsty about disclosing that because you’re hinting at what you think you can do?
Speaker 1
Yes, but people can figure out net new ARR, and they can figure out what your bottom line is.
Speaker 0
True.
Speaker 1
What we used to do was net promoter score and stuff like that, and that gets really tricky having to disclose that.
Speaker 0
I really like it. Very few comp committees do what Brian does because I think that’s so much better than just stock price.
Speaker 3
Every growth round that I’ve seen in my little portfolio has had moonshot packages. So they’re going in earlier, and they’re becoming a standard part of how many growth funds win deals. They go in and say, “Yeah, I’ll do the deal at $1 billion, but I’m going to give Harry another 7% of the company,” and they’re always at least 10X. There’s a quid pro quo. It’s not 10X; it’s 10X from what I’m paying as a growth investor.
“Fine, I’ll do Clay at $3 billion, but if you hit $30 billion, you guys both share another 10% of the company.” And so I think this is getting institutionalized earlier and earlier as valuations go up.
Speaker 0
Agreed.
Speaker 3
So it may not matter what any of us think because the growth guys are adding this to the standard term sheet.
Speaker 0
The slimiest version is where you literally say to the CEO, “I’ll effectively give you options back for the dilution you’re taking on the round.” This is a little more high-class than that because it’s saying at least you have to achieve first.
Speaker 3
Well, usually you get more. What I’m seeing is—
Speaker 0
Yeah, agreed. No, it’s—
Speaker 3
Instead of a growth fund saying, “I’ll give you another 2% back”—forget that, I’ll give you 7% or 8%. I’ll give you a massive package, but I’ve got to make my 10X. It’s their version of the Elon package.
Speaker 0
And I think what happens there—and my prediction is, again, I’m often disagreed with on this on comp committees because I’ve done some of these where I’ve tried to make them on tangible targets—is that when you do the stock-price ones, if the company’s doing really well but the stock price isn’t achieved, the CEO will be sitting down 2 years from now and asking to waive some of the criteria. I can just see the movie now.
Speaker 3
I’ll bet you nickels to dollars that doesn’t happen because I don’t know about Brian—you see it at Sequoia—but founders are signing up for crazy stuff these days. They’re signing up for massive packages, and I don’t think a lot of grouchy VCs are going to waive it. I just don’t think it’s going to happen. I hear your point, Rory. I just don’t think it’s 2024 anymore.
Harry Stebbings
Brian, you are an amazing coach to founders. I speak to Pat and Jared a lot, and they say that founders love your coaching, mentorship, and advice. When they have big growth rounds like these, with performance-based incentives like we’re talking about, how do you advise them? Is it what you thought you’d see now on the other side?
Speaker 1
I like all this stuff for the founders. The other thing I like is founders taking a little bit of money off the table on the way. For us, when we did our round, it was Sequoia. Sequoia came to us and said, “We’d like to buy some of your shares.”
In retrospect, a horrible financial decision for me, but it was good at the time. I sold, I forget, a couple million dollars’ worth of HubSpot shares, and my co-founder and a few other people did too. What I liked about that was, you know, Salesforce came knocking and wanted to acquire HubSpot. It stiffens my backbone a little bit. So it’s good for the founder, it’s good for the VC.
I think it gets a little wobbly when it’s a $50 million secondary in the Series B, but in general, I like what’s going on in venture. I think the valuation is very high right now across venture, so we’ll see how this thing plays out. I think it’s a little bubbly right now. But I generally like the trend that’s going on in terms of the secondaries happening for founders, and I like these PSU-type rounds.
Speaker 3
There's a founder I'm working with right now who's a terrific founder, who just took a while—4 years—to get it going, and now is ripping. He's been massively diluted, so I'm like, “Well, let's figure out a way to give you a nice big grant.”
Speaker 0
I agree with all that, and I do think, though, that valuation is the imperfect metric. And Jason, I think you're wrong. I think investors, grouchy VCs, will recut, because CEOs are smarter than us in comp.
What I've learned is this: I have a board, but they're running their company, and they obsess about it day and night. Let me tell you, if you've got a CEO who doubles revenue for the next 2 years, and the only reason he's not making his extra 3% is because we overpaid 2 years ago and now revenue multiples are normalized, and therefore I'm not getting my 5X, he's going to come into the comp committee and say, “I have nailed running this company. We have 3X'd revenue. We're operating-income positive. Give me my damn shares.”
And I'll sit there going, “I knew we should have done a revenue and operating-income target like Brian has at HubSpot from day 1.” Because what we're doing right now is we're taking what Brian correctly calls high-end valuations, and then we're 10X'ing them, and we're basing comp on that. We're basing comp on a chimera. It's never going to happen.
Look at all those 2021 moonshot publicly disclosed ones. Most of them are like, “Ooh, what were we thinking? We thought we'd go from $200 billion to $2 trillion. Hmm, maybe not.”
5. Canva Should Go Public
Harry Stebbings
If we think about going from $200 billion to $2 trillion, there's going to be a boardroom that's thinking, “Huh, should we take some action now?” If you are Canva, are you looking at this going, “Forrest Gump, run. Let's head to Nasdaq”? How do you think about the impact of this on Canva and subsequent companies' willingness to go out?
Speaker 1
Yeah. Run, Forrest, run. The market's wide open. The valuations are good. There's a lot of demand. It's very seasonal and oddly seasonal, and timing really matters. If I were Canva, it's an amazing company, I would be lining everything up to go public.
Speaker 3
But the founders have already pledged to give away the majority of their stock. It's not about money for them.
Speaker 1
They're giving it away to good causes, and they want those causes to get as much of it as possible.
Speaker 3
Yes. I'm not saying I know the answer. I just think it's more complicated than someone who needs the money. All the early-stage investors have had a chance to trade at tens of billions, right? There's just a lot of liquidity already there. The company's massively profitable. I just can't—I’m not smart enough to predict how those factors stand together, right?
This clearly isn't a Musk empire that's being built at Canva, right? It's very different.
Speaker 0
I mean, I've been thinking about that. You have all the idiosyncratic personal things. You have people who say, “I don't want to go public for a long time,” and you have people who need to go public early, right? All those are idiosyncratic.
But if you zoom out 1 level, because I actually had this conversation with an LP, they were asking, “When does it open?” In the end, price clears all markets. For the last 3 years, money in private rounds was cheaper and less hassle than in the public markets, so no surprise we did more private.
Let me see: 5 times revenue with a bunch of people in New York busting my balls versus 10 times revenue, and I never get to talk to these growth-stage guys except once a year. I'm doing Option B.
Now you have a situation where maybe at the IPO price for Figma—18 times revenue—you go, “I can get that privately.” You can't get 80 times revenue privately. So if you're now looking at where things are trading today, I think, at the margin, those prices are higher than the private things.
Stepping back from the idiosyncratic stuff, at the highest level, the cheap money is now in the public markets, and Brian's right: you'd be an idiot not to go for it. If you need to raise money in the next 2 years, now would be a really good freaking time.
Speaker 1
In Silicon Valley, Stripe is really beating the drum on this: “Why the heck would we ever go public?” There's that sentiment out there—
Speaker 0
Yeah.
Speaker 1
—because there's so much private capital, and you can do secondaries. But I think people are just nervous about what's on the other side.
My take on it was: we're a private company. We had a bunch of quirky, slightly misaligned venture capital investors who were definitely in our shorts. And then we flipped to public, and then we got rid of those VCs. Now we had a bunch of quirky, slightly misaligned public investors who were less in our shorts. It's actually better in a lot of ways than being private.
And public investors—there's so much written about what happened with Zendesk or Autodesk, or these really bad things that happen. It's pretty rare. I have found the public investors to be pretty rational if you paint them a picture of what will happen over a long period of time, if you're pretty conservative with your numbers. They're rational, and they'll stick with you.
I think they're underrated, and I think people think it's—
Speaker 0
Yep.
Speaker 1
—something scary over there. It's not as scary as people think.
Harry Stebbings
I have a lot of founders who say, “I'm terrified of the activist investors. I'm terrified about what happened to Jeff at Twilio. This is my company. This is my life. I don't want to have that happen to me.” What would you say to that founder?
Speaker 1
It's pretty rare, what happened to Jeff. Everyone talks about Jeff, everyone talks about Autodesk, everyone talks about Zendesk, but it's pretty rare. And that company was having some issues.
Speaker 0
I agree, Brian, and I am a “people should go public” person. I think it's a little overbought. I do think the activist VC—because we were one of them—
Speaker 1
I think VCs are a much bigger pain in the ass than public investors.
Speaker 0
We are much—agreed.
Speaker 3
Let's add that to the B-roll.
Speaker 0
Yes. I think VCs are a much bigger pain in the ass than the typical public investor, and slightly less of a pain in the ass than the public activist investor. I'm pretty sure on that one. I'm going to defend us—
Speaker 1
Yeah.
Speaker 0
—there, Brian. Most times, the public guys are benign. Though I will say, in the last 5 years on the venture side, definitely the benign contingent has ramped up.
So it just comes down to this: even 10 years ago, I think the marketing in the last 10 years on the venture-growth side has very much been, “We are more benign than the public.” I think that might be misleading. That might not be true.
So I think you're right that it's a healthy trend to realize that you can go public. You get this liquid stock. It's not as terrifying as you think, and you have liquidity every day, not just once a year by appointment only. I'm a big “IPO should happen” person.
Speaker 1
Here's what's underrated about the IPO. It's very stressful. You're exhausted. But the day you go public is going to be one of the top 2 or 3 days. It is an amazing day.
You'll go back to your company, and 2 days later, you'll have a party with your company. You will cry. You will laugh. You will hug. You worked so hard. There's something about that that's really, really special when people do it.
Speaker 0
Got it.
Speaker 1
Agreed.
Speaker 3
Having said all that, I've only lived through it on the employee side, when it was great, right? The day after that was weird, going back to your desk because the world's changed. The next day is really weird.
But if I could IPO at $30 billion or sell my company for $30 billion in cash, I'd much rather run the company—don't get me wrong—rather than sell, right? But if it were just a financial decision, I'd rather have the $30 billion on 1 day than wait a decade for it to drip and dribble out, right?
So there is a conflict there as a founder. Selling is tough for 98% of founders. I'm sure at Sequoia, if you ask, only 2% of founders say, “That was the greatest experience of my life selling my company.”
But getting it all at once, if it's the same, even with the net present value, it's just a weird trade-off between the two—the journey and the economics. It's complicated.
Harry Stebbings
I just want to butt in there, Jason, because you said there about getting it all at once versus drips and drabs.
Speaker 3
Yeah.
Harry Stebbings
I'm super naive here, Brian. You said about it going from, like, X to 100X. When you do go public, is it drips and drabs over years?
Speaker 1
It's a drip and a drab. You can look at the way I do it: I sell the exact same number of shares every month since we went public. The reason I do that is I don't want to signal something. If I make a big buy or a big sell, it's going to signal something. It's funny—people will look at it. The investors look at it.
So I sell the exact same number of shares every month. It's on autopilot, and it's drips and drabs. You're definitely right.
Harry Stebbings
Do you know how much you have left?
Speaker 1
Yeah. I've got plenty left because I got more shares. Here's the thing that I didn't understand as a founder: you get more shares as time goes on. I actually didn't know that when I started HubSpot. I was like, “The pie would get smaller.”
Actually, the pie got much smaller, and then the shares started growing a little bit.
Speaker 0
One of the things we didn't warn you about joining the podcast, Brian, is that every once in a while, Harry basically asks you to disclose your net worth or that sort of thing.
And you have to remember, in the prison cell, you don't have to answer. You can plead the Fifth on anything, right? No, Harry, I will not disclose my last raise on term sheets, nor my net worth. Just refuse point-blank.
Speaker 2
Rory, what was your multiple on HubSpot?
Speaker 0
I'm not going to disclose that. Extraordinarily good, and I'm extraordinarily grateful to Brian for allowing us to do the Series C, especially when I had whiffed the B, and my colleague Rob, and then Stacy, took over and did the C and corrected my dumb decision-making. We were extraordinarily lucky to invest in them at something like a $70 million pre-money valuation on a company doing $10 million. Thank you, God, from the bottom of my heart every time I go to my little house. Thank you, thank you, Brian.
Speaker 1
Speaker 0
No.
Speaker 1
The Series C was bad timing. Timing matters more than I ever would have thought or studied in school.
Speaker 2
Bad timing because Rory hadn't had lunch and he was grumpy? What do you mean, bad timing?
Speaker 1
No. It was in the throes of the recession back in 2009.
Speaker 2
Got you. Yep.
Speaker 1
Dharmesh and I got off the plane from Boston and landed on Sand Hill Road. We were like, “We got this. We're going to go up and down.” It was about 20 meetings. We went to all 20 meetings and got back on the plane. We were like, “We got no's.” We went up and down Sand Hill Road.
Every big-name firm—
Speaker 0
Yep.
Speaker 1
Everyone, every household name, said no. We went back and forth. We had nothing. So we were about to do an inside round at a slight uptick to our B. At the very last minute, Rory and Rob Fias had us in. We pitched them, and they gave us a term sheet at a $66 million pre-money valuation. So, actually, the thanks goes from me to you, Rory, because you marked up our deal. I appreciate you.
Speaker 0
Yes, I remember. That was in 2009. We did HubSpot, Box, DocuSign, and I think RingCentral. The time to buy is when everyone else is not buying, especially when, let's put it out there, you're just little old Scale and you're not Sequoia, who came in after.
Bring on those days again. I mean, the world may have to end, and that's obviously a little tough for everyone, but it will be really great when companies like HubSpot are grateful to get my term sheet at a $66 million pre-money valuation, just to remind everyone that they were doing somewhere between $7 million and $10 million, doubling year on year. But other than that, it was a tough decision. So grateful, Brian. Thank you very much.
My multiple was excellent, Harry, so pound sand. It would have been even better if we had had the mechanism then to hold for long after the IPO. I profoundly wish we'd had that as well, but—
Speaker 3
You couldn't hold, Rory? You weren't allowed to under your LPAs?
Speaker 0
It's a long story. We had a single LP. We had to distribute. It's a long story. Move on.
Speaker 1
Yeah, the smarter money in HubSpot was in the public markets, since we went from—
Speaker 0
Absolutely.
Speaker 1
—from $1 billion to $10 billion to $25 billion—
Speaker 0
To $25 billion.
Speaker 1
—in a relatively short period of time.
Speaker 0
Yes.
Speaker 1
And I think Sequoia's really smart. I suspect HubSpot was one of the reasons they said, “Let's hold these companies after they go public.”
Speaker 0
Yes.
Speaker 1
It backfired in some cases, but I think it's going to work over the long haul.
Speaker 0
Yes.
Speaker 2
I asked Rory for the multiple. He's like, “No, no, no. Moving on, moving on.” And then Brian's like, “Let me tell you how he missed it.”
Speaker 0
…in the B. And you're like, “Oh, I prefer the multiple question. Let's go back.”
Speaker 1
Speaker 3
Give Rory credit. As great a company as HubSpot was, it clearly wasn't a consensus bet at the time. Objectively—
Speaker 1
Marketo was the consensus bet. Marketo was raising at bigger valuations. They were always raising 3 rounds—
Speaker 3
Well, they were more enterprise, Brian. That's the play. You've got to go more enterprise.
Speaker 1
Right, Rory?
Speaker 3
Yeah.
Speaker 1
Yeah.
6. The SMB Growth Bet
Speaker 0
It is actually worth riffing on that because we have the king of SMB on this call with Brian. The interesting thing about HubSpot was the way they built a $30 billion market-cap business in SMB, starting with sub-50-person companies. And you're right, Jason, it was very counter-consensus wisdom at the time. Did you ever want to go upmarket?
Speaker 1
I never did. The reason we bet on SMB was that I had spent my entire life doing the soul-crushing exercises of selling to CIOs, and it's just—
Speaker 0
Nice.
Speaker 1
The internet disproportionately benefited small relative to large, at least back when we started. Your success was much more about the width of your brain than the width of your wallet, and so we had a play on that.
We also just looked at the consumer business. The P&L is a shitty way to look at these businesses. Let's look at CAC and LTV—
Speaker 0
Yeah, yeah.
Speaker 1
—and convinced ourselves that worked. One interesting thing about HubSpot's SMB business—the other SMB company that's done amazingly, even better than HubSpot—is Shopify.
Speaker 3
Yep.
Speaker 1
They're both outside of consensus land in Silicon Valley. There's a big echo chamber in Silicon Valley and a big negative bias toward SMB. But you can make it work in SMB. HubSpot and Shopify have shown it. Block has shown it.
Speaker 0
Monday.com as well.
Speaker 3
Yeah.
Speaker 0
Massively anti-consensus.
Speaker 1
Yes, they are, in a way that you guys hadn't.
7. The SMB AI Challenge
Speaker 3
But would you have made the choice today, Brian, in AI? The reason I ask is that, to make a lot of great AI products work, you need training. You need upfront—you need forward-deployed engineers. You need daily training. Even if it's SMB, every day someone's got to be your AI orchestrator.
If you were doing all that today, would you go a little bit more mid-market? Because these SMBs don't have time to train their AIs.
Speaker 1
Here's one of the interesting things about my life: all these founders come to me and say, “How did it happen with HubSpot? How did you do marketing?” We talk about our website creator, content marketing, and inbound marketing. “How'd you take on Salesforce?” We kind of came in under them with freemium.
We learned a lot, we innovated a bit, and a lot of what we learned just wouldn't work today. You've got to keep innovating, you've got to—
Speaker 3
Totally.
Speaker 1
Keep turning that lever. I'm careful giving people advice about our culture. People need to find new things. I'm nervous when I give people advice and tell them what we did at HubSpot, because it worked at the time and it was really innovative at the time, but a lot of what we did on go-to-market—the freemium stuff, the PLG stuff, the interesting culture stuff, our SMB play—you know…
Speaker 3
Some of it works and some of it doesn't, I think.
Speaker 1
Some of it works and some of it doesn't, yeah.
Speaker 0
Jason, I'm literally exploring this without knowing the answer. Is there a great SMB AI product out there today? Well, Lovable. Stupid question, Rory. You seem to imply that it's harder to do enterprise- or SMB-level apps in AI because of the need for training data, and then I'm trying to think: what are the mass-adopted enterprise apps? Obviously, you're the Lovable and Replit guys, so there are some.
Speaker 3
Speaker 1
I learned a lot of AI from Brian's AI. I copied it and made it better. When Brian built his clone, he and I were talking at the very beginning. He's like, “Well—” I'm like, “Brian, it's pretty good.” I had some fun, cathartic conversations with Brian's AI.
I'm like, “It's pretty good. Mine's better, only because it's trained on more data.” But I didn't get it. I asked Brian, “Why is yours so good?” He's like, “I spent a lot of time training it.” This was 6 months ago. This is a lot of time, and I didn't get it.
But now, when I look at every true AI company, it's hard to train it, right? And so—
Speaker 0
Right.
Speaker 3
This is a quandary for SMB investments. What I'm looking for in SMB companies in AI is: how do you self-train? How do you solve the unsolvable issue? How do you solve the fact that it can take 6 months to roll out a Palantir-grade deployment? How do you do that in 60 seconds?
Any founders that crack that code, I want to invest this hour, this second. I'm pushing every startup I work with that's SMB to be more AI, and sometimes they push back on this, right? But you've got to do it. How do you train?
Speaker 1
The stuff I see, Jason, is that there's a ton of prosumer stuff that's working. Lovable's working, Replit's working, Gamma's working. So many prosumer things seem to be working, and then enterprise is working. I haven't seen much in between so far.
Speaker 3
But there's no training in the game. I mean, we use Gamma too. We love Gamma. But you don't train Gamma. I mean, you do train Gamma a little bit, don't get me wrong. You sort of accidentally train Gamma by uploading your templates and your things, right? Replit and Lovable—I mean, I'm a vibe coder, right?
Speaker 0
Speaker 3
The training is weird, though. It's AI under the hood. So I just think this AI B2B SMB is something that hasn't been cracked, to Rory's point, and I think we should all just rush all our capital into that. Listen, if you can train an AI, it's easy. HubSpot just put out this report on AI with SMBs, right? It said 80% of folks have an AI team to do this.
Speaker 4
Even with what they call the SMB and VC, 80% have a team. SMBs don't have a team. One restaurant that Brian and I invested in—they don't have an AI team. All right? At Brian and Jason's Sandwich Shop, there's no AI team.
Speaker 0
As I say, I opened the door to an unprepared topic, so I'm winging it. But my sense is—2 comments. One is, it may well be that it takes 1 or 2 years longer, because if you think about even the HubSpot journey, what tends to happen is the big companies with loads of money fart around mentally defining these apps and figuring out what it should be, because they can afford to, right? And then when the features lock in, the SMB guys go, “Ooh, we'd like that,” and then you don't have to do so much, in the case of that last generation, trying to figure out what it is.
In the case of this generation, you probably come with a very much pre-trained app where, if it's call answering or something like that, most of it's already done and you just have to configure it at the SMB level. And it may be over the next 1 or 2 years, because I do believe—and this is, I think, one of the reasons we love HubSpot—anything the big companies have, the small and midsize companies want, too. They're not different. They just need it packaged tightly and priced tightly so that they consume it in bite-sized chunks.
So over the next couple of years, it may well be, as I say, for things like phone answering and simple order dispatch, that there'll be a whole bunch of precanned, prebaked solutions: “This is how it works, Mr. SMB. Just turn it on and you, too, can sound like a big co.” I'm optimistic. It won't be trained on a company-by-company level, but I think it will deliver big-ass value.
8. The AI Spending Bubble
Harry Stebbings
You said there about big companies with lots of cash. I do want to progress this because there is something I'm fascinated to hear you guys' thoughts on. And what a fricking ripping quarter: a 38% year-over-year increase in adjusted EPS, 22% revenue growth, but a 22% drop in free cash flow. How did you guys read it? How long does this go on for? Is this the start? Is this near the end? How much patience do people have?
Speaker 0
It's funny you led with, “How long does it go on for?” because 2 weeks ago, when I said, “How long does it go on for?” you looked at me like I had 2 heads.
Speaker 4
You see the shit I put up with, Brian?
Speaker 0
Yeah.
Speaker 4
I just take it.
Speaker 2
I take it because I'm polite. I don't give it back; I just take it.
Speaker 0
And I will say, on all these things, the takeaway—and I like the way you framed it here, not the way you framed it in the note you sent me prior—is this: this isn't AI-enabled success. This is: I have an awesome existing business, and it kicks off so much money that I'm allowed to spend that money on building this great AI vision, and I can probably do that for as long as my existing business kicks off cash.
So my big aha from this week's earnings—and I would say I got broadly AWS right and I broadly got Microsoft wrong—is that not all the AI stuff is working for the hyperscalers. My big takeaway is that all their existing businesses are working so well and kicking off so much cash that they can keep doing this for the next year, and they said they're going to keep doing this for the next year because they want to play in the new game. That's the takeaway. Real men with $70 billion of free cash flow get to spend $40 billion of that on servers. It's a great country.
Speaker 4
Is there any nervousness at Sequoia, Brian, at all that the good times might end soon? Is there any draft—
Speaker 0
Yeah.
Speaker 4
Ready? A Sequoia memo, version—
Speaker 0
Ready.
Speaker 4
—3 waiting to go out? Just search and replace and Gamma? Just have, “Gamma, please dust off the RIP Good Times and update it for AI.” Any discussions at the partner meetings you've been in about that?
Harry Stebbings
I mean, David Cohen wrote the piece about the chasm between CapEx spend and revenue.
Speaker 4
And one of the questions is, are we in a bubble or not? The argument against the bubble is sort of just look at Anthropic and ChatGPT, and their growth rates are—
Speaker 0
Astronomical.
Speaker 4
—ridiculous. Or you look at even Harvey or so many of these companies that are app-level. What I like as an investor looking at this stuff, I get nervous about tech companies selling to tech companies.
Speaker 0
Yep.
Speaker 4
Yeah, and Silicon Valley companies buying from Silicon Valley. There's a lot of trading going on, and there's a lot of growth in there. I like what ChatGPT is because mere mortals are using that thing. I love what Harvey's doing. They're selling to lawyers. I like what Rogo's doing, selling to investment bankers, stuff like that.
I get nervous because I think 2001—and definitely in 1999 and 2000—it was just Silicon Valley companies buying and selling from each other.
Speaker 0
Well, 2020 and 2021, too. A lot of it, right?
Speaker 4
For sure. Yeah, for sure. So I like these ones selling to mere mortals. But it has to be a bubble at some level. The CapEx bubble—it can't last forever. Look, AI is bigger than the internet, most likely, right? Bigger. The investment makes sense, but when you see Meta's cash flow decreasing, there's some kind of bubble here. Hopefully we all get out, but it's some kind of bubble.
Speaker 0
I think “bubble” is just a loaded word. It's the usual 2 things. There's an enormously enabling technology. It's getting massive traction at the app level, as Brian mentioned, but you still add up all the apps' revenue and it probably comes to $25 billion, $30 billion maximum, and the CapEx to build that is running between $400 billion and $600 billion.
So you're investing $400 billion to $600 billion a year to enable a $25 billion ecosystem to go and keep doubling, and maybe next year it's $50 billion. My takeaway is the long-term trend is almost certainly real, and if you fast-forward 10 years, that $25 billion to $30 billion of apps revenue could easily be $300 billion to $400 billion. So that's why, in the long term, it's not a bubble.
There's probably going to be a period where things get ahead of themselves. The marginal player will get caught, just like the marginal player got caught in 2001. The overlevered player who's taken on too much debt financing will get caught and get burned, and the big guys will retrench for a year or 2 and then just grow into it.
That's the most likely version of the movie, which is some pain at some point in time. And it's boring because it's neither one: it's not amazing AI maximalism, and it's not bubble doomism. It's just that we're doing what we always do with a new technology. We're spending like crazy because it's the only way to discover the frontier, and until you discover the frontier, you're not investing enough.
So we're doing—as an organization, as an organism almost—capitalism is working. We're spending money trying shit that works. Some of it won't work, but unless you try, you just end up like Europe. Sorry, Harry.
Harry Stebbings
You always shit on me. You're so Irish.
Speaker 0
Harry, we've had 800 years—
Speaker 3
He talks more European than you do, Harry.
Speaker 0
Harry, we've had 800 years of you guys shitting on us. Every chance I get to shit on your back, I'm going to take it, so just get used to it, man.
Speaker 1
Aside from the navel-gazing on this, because I don't know what the answer is, I would just say I'm incredibly impressed by how fast Microsoft is growing at massive scale, and how fast Meta is growing.
Speaker 0
Totally.
Speaker 1
Companies people aren't talking about are the very old-school Microsoft, SAP, and how about Oracle?
Speaker 3
How about Oracle?
Speaker 1
So my date is August 26, 2022. That's when everything kind of hit the bottom in share price. If you go from that date and you look at Oracle and you look at SAP, they're both growing 230%.
Speaker 3
Stock.
Speaker 1
The only SaaS company since August 2022 that's growing faster is Shopify. They're growing 300%. So they're outpacing HubSpot, Salesforce, Adobe, Box, Atlassian, everybody.
Speaker 0
Are you talking stock price or revenue growth rate?
Speaker 1
Stock price.
Speaker 0
You're becoming a stock-price baby. I mean, look, I think part of that is a function of the fact they started at a much lower base. I think you are right, though. The stunning thing in Oracle's particular case is how they've, rightly or wrongly, I'll say, taken that free cash flow and invested it in GPUs and have now made themselves relevant in cloud.
Speaker 1
Yeah.
Speaker 0
Provided that market keeps growing, that's clearly worked for them so far.
Harry Stebbings
Rory, I know you love unfair questions. I'm going to give you the chance to grant a CEO of the Year award, and you can grant it to Satya or Zuck. Which one do you give CEO of the Year to?
Speaker 0
You know, I'm deciding I'm now going to be the new humble me. It's inappropriate for me, a mere VC, a little grasshopper, to comment on which of those 2 amazing CEOs is the best. They're GOATs.
Speaker 1
I think the CEO of the Year is Jensen.
Speaker 0
I'll go with that.
Speaker 1
But the other thing I like about Jensen is he's rethinking the role of the CEO.
He's rethinking the CEO playbook. I think he's a pretty good inspiration for CEOs out there today.
Speaker 0
The reason the two people you've cited, it's very much existing business carrying and doing something in the new world, whereas I think someone like Jensen or OpenAI—you see Dario—we've created the new world. The two categories in the stack that didn't meaningfully exist at scale in SaaS and cloud land that exist now are the GPUs, which is all Jensen, and the models. Neither of those categories even existed, and obviously, not only do they exist, but they appear to be dominant relative to the other parts of the category, other apps in AI land.
I think Brian's right. Those are the contenders for CEO. The other guys are contenders for managing the cash machine brilliantly at scale and keeping it up and to the right, which turns out to be a pretty lucrative way to spend your adult life.
Speaker 3
I'll tell you why you absolutely have to go for Satya over Zuck by far. It's more a structural reason, and this is certainly what I learned in my tenure as a VP at Adobe. As a founder, this stuff's easy. You just call the troops together. Zuck can do what he wants. Satya, I just watched Adobe trying to go to the cloud. It took 3 years of convincing everybody.
Speaker 0
Yep.
Speaker 3
So what Satya's done—inviting Sam Altman back in, doing the deal, managing the deal, doing this kooky deal to buy 49% of OpenAI, investing all in on Azure for AI—he doesn't have the power to do this on his own. Brian and Dharmesh can get together, and honestly, you guys can just decide what you want to do. I know I'm being simplistic, but I would bet you'd agree, right? For Satya, this is the amount of meetings and orchestrations and stuff you have to do as a non-founder. I give him credit, because it's much harder.
Speaker 1
He's like a re-founder. He basically acts like a founder. He gets stuff done like a founder. He's just super impressive.
Speaker 0
If you accept the constraint that you can't build the core technology internally, which is what Microsoft had to accept, and he accepted, execution since then has been perfect. You found the only other people that had the technology. You gave them a convoluted deal. You suck a lot of value out of them. You have the ability to resell it. All those things are awesome.
At some level, you must kind of wish, as the CEO of Microsoft, that there must be a little part of you that says, “If my guys were only smart enough to build the shit that OpenAI was building, I wouldn't have to do all this crazy stuff.” But maybe that's the nature of being smart enough to accept that this large bureaucratic company can't get it done. Maybe that's the answer why it's awesome.
He's lived with the reality of, “I wish my people could do this, but they can't, and I'm not going to keep banging my head against the wall. I'm going to do this very hard thing for a non-founder to do. I'm just going to cut this weird deal with these other dudes, give them $10 billion, own 49%, insert myself into the AI business without actually having the core model that you should have had to be able to do it.”
He must feel—maybe the real soundbite in his head is, “Thanks a fucking lot to the rest of you guys. I had to figure this out with 1 business development guy while all you guys were sitting on your ass not shipping AI.” Maybe that's what he deserves the medal for. Not easy.
Speaker 3
Not easy. And he has to take 49% of the losses, massive losses flowing through their financial statements. You could argue asterisks and daggers, but it's not cost-free, right? There is a cost.
Speaker 0
3% of the OAI, they'll be fine. I mean—
Speaker 3
Yeah.
Speaker 0
30% of the OAI in return for, you know, probably $1 billion a month.
Speaker 3
But you get criticized for this as a non-founder CEO. You get criticized—
Speaker 0
Yes, you know—
Speaker 3
—for every line versus Zuck. They're like, “What are we going to do?”
Speaker 0
Yeah, just being ballsy enough, you know, I—
Speaker 3
What are we going to do with Zuck?
Speaker 0
That's actually—
Speaker 3
What are we going to do?
Speaker 0
Just being ballsy enough to write a $10 billion check for something weird is, in and of itself, heroic.
9. Cognition AI Valuation
Harry Stebbings
Guys, I do just want to go to a couple of private rounds, just because they've really stood out to me. We said something about companies that we've talked about before. Cognition is now rumored to have done a round at $15 billion, the new combination being, obviously, Cognition and Windsurf. Both had $85 million in revenue, so combined, you're at $170 million, being priced at the new $15 billion. How did we think about this?
Speaker 0
What you're saying is the rumor was it was being done at $10 billion, and now the rumor is it's been done at $15 billion. It's pretty much the same as the Anthropic rumor. It's done at $100 billion, and now it's been done at $170 billion. I think what it says is demand is high for premium assets.
So it's a little like it's the private IPO. You float a price of $100 billion, and you end up at $150 billion. You float us a price of $10 billion, and you end up at $15 billion. I think there's just a lot of demand for perceived premium AI assets, and price is how scarce assets get allocated.
Speaker 3
I just thought this layoff buyout thing was crazy.
Speaker 0
Separate question, but yes.
Speaker 2
Unpack that, Speaker 3.
Speaker 3
I guess today, Cognition laid off 30% of the folks they bought, and they offered to buy out all the other 200 employees. They gave them a 9-month package. They told them they either had to work 80 hours a week, 6 days a week in the office, or they should take a 9-month package.
And listen, no criticism—great people here, right? Some of my best portfolio companies use Devin, which is pretty interesting, when I talk to them. But doing this hero acquisition, then laying off 30%, and then telling everybody to either work 80 hours a week in the office or take a 9-month package, and then finding out that the founders and the investors put in the $100 million—Google didn't—the story's much more complicated than it looked at first.
There aren't quite as many white hats, and everyone's a gray hat, it turns out.
Speaker 0
Agreed.
Speaker 2
Okay, but let's just unpack that. Why make the acquisition, then, if they're going to get rid of 30% and then say, “Hey, all of these terms are posted,” if you're buying the team?
Speaker 3
I don't think they were buying the team. I think it's clear they weren't buying the team. I think it's clear that Devin is an AI engineer, okay? And I talk to all the folks in my portfolio. The 2 actually toughest-problem CEOs are using it, okay? Stuff where they're reluctant to use AI. They like Devin, but it only does a little bit. They pay for it, it's fine, but they're not deploying it across their whole team like Claude Code or something.
So they have a niche product that's done well, and they want access to a top platform to get into everybody, a broader platform. And so they bought a brand. They bought $80 million of revenue to maintain, right? And they saved themselves 3 to 9 months, and basically did a deal that looks non-dilutive at the end of the day at this $15 billion. Maybe there's just a lot of spin on a deal that was just for brand and accelerated market entry.
The fact that they're offering to let every single employee go certainly means they don't see a lot of value—
Speaker 0
Oh—
Speaker 3
—in the folks that are left.
Speaker 0
Or there's an implicit cultural statement. And again, they're doing the, “You were all working 9 to 9, 6 days a week, and you guys aren't. If you want to sign up for this, do. If not, leave.” You're right, there's an element of clarity to it.
Speaker 3
They've got until August 10th, all employees—
Speaker 0
Yeah. Yeah.
Speaker 3
—to decide whether they're staying or going. It's a lot of change from the last pod.
Speaker 0
But all predictable. I mean—
Speaker 3
Bye, guys. I'm not laughing, because the human implications here are so stunning, right? I mean, Google's such a jerk. We don't want anybody—we want the company to die. Then the investors and the founders having to take the $100 million out of their own pocket and leave it in Windsurf. Google didn't do it. They had to do it after the deal was handshaked, apparently.
Then it all happens. Then they get bought at the 11th and a half hour, and now everyone gets a buyout package? It's just, even in a 9-6-6 world, it's too much.
Speaker 0
Yeah. Because they all made the comment prior to that that they got their equity cashed out. What you don't know is how that compares to taking that $100 million, closing the company down, and splitting the money. I genuinely don't know how they ended up.
Speaker 3
Crazy.
Speaker 0
But what it says—I mean, look, what it says is this: the minute you move away from the cap table to making it up as you go along, if you're not one of the key players, you're very vulnerable to—you're basically depending on the kindness of strangers, as Blanche DuBois would say, which is always a mistake, right?
You're depending on people arbitrarily deciding, quote-unquote, “what fair is,” and people's decisions on what fair is change over time. Versus in a normal M&A, where you know where you stand. It's a Delaware corporation or a Nevada corporation, and you get what you get.
I think the lesson here—
Speaker 3
Yeah.
Speaker 0
—is once you get away from that, everyone's just winging it, and it's hard to know from the outside.
Speaker 2
Did you quote A Streetcar Named Desire?
Speaker 0
Yes, I did.
Speaker 2
In a VC pod. My respect and love for you has gone through the roof, Speaker 0.
Speaker 0
There you go. There you go.
Harry Stebbings
Wow.
Speaker 0
The—
Harry Stebbings
That is fantastic. There are 2 more things that I wanted to discuss. Ramp raised a $500 million Series E at a $22 billion price. Iconic led it. This is the fifth or sixth round they've raised in an 18-month period. Is this aligned with company progression, or is this late-stage capital trying to find a home?
Speaker 0
Just a little bit—
Harry Stebbings
You know what?
Speaker 0
…of the humanities. Yeah. Well, now that computer science is out, I'm gonna go back to doing my English lit exam. Yeah.
10. Ramp Needs Capital
It's probably a bit of both, because remember, Ramp, unlike most software companies, part of what they do is lend money. They basically give people corporate credit cards on which they earn the interchange, and the way you earn the interchange as the issuer is that someone has to fund them for the 30-day float period. Now, I don't know in their case: are they funding it themselves, or do they have some kind of flow-through? But in any event, issuing a corporate credit card, by definition, is way more capital-intensive than simply building a software company.
And so they're doing both. So it probably consumes more capital than the typical software company. The faster you grow, the more capital you consume, so at some level, there's gonna be a capital need for that. Then, on top of that, you obviously have the phenomenon of it being a wildly hot, successful company, perceived as dominant in its category, and by virtue of that, it's just gonna attract a lot of venture capital interest.
If people keep offering you money at increasingly higher prices, you're probably gonna take some. So, probably a bit of both.
Speaker 3
The other thing is, when I look at Ramp, $22.5 billion, right, very quickly.
Speaker 0
Yeah.
Speaker 3
But $500 million, it's only 2%. Clay just did a round at $3 billion, which is stunning growth, too, right? But they sold $100 million, right?
Speaker 0
Yeah. Why not?
Speaker 3
So these little tiny rounds, the absolute dollars may sound large, but they're not even rounds, right? When we're talking about 1% dilution, 2% dilution, and the VCs get a markup out of it, do they really count, right?
I remember back in the day, I had a markup at a $3 billion investment, right? And I asked my anchor, but it was a very small number. My anchor said, “Don't recognize it. It's not big enough. It doesn't count.”
Speaker 0
Whoa.
Speaker 3
I'm not saying that's the same here, but if I'm Ramp and I could sell 1% in a series of rounds, there's no cost. Is there?
Harry Stebbings
Do you think these are good rounds for companies? I've heard them called suicide rounds, where a $100 million round at a $3.1 billion valuation just sets a very, very high price to grow into, with not actually that much capital added.
Speaker 3
Well, that's the downside, right? Maybe it is a suicide round.
Speaker 0
I think if you need the money, you have to get the money, and if you need the money at a high price, a high price is better than a low price. Raising money at too high a price is only, quote, “suicide” if you have to raise again.
If you don't have to raise again and all you do is have some investors who've overpaid and then take 4 or 5 years to grow into that valuation, well, that's tough shit for the investors. But from the company's perspective, it's fine, and you're glad you got the money.
What you don't wanna do is raise $1.03 billion when you needed $400 million, and then go back out 6 months later. You haven't had the growth, and in theory, you're only worth $1.5 billion, but then people get the cognitive dissonance of it being a down round, and then you're screwed.
Speaker 3
That's a suicide round.
Speaker 0
That's a suicide round. But if you raise $500 million at $2 billion, and 3 or 4 years later you go public at $1.5 billion, well, tough shit on the guys who paid $2 billion, but life goes on.
Speaker 3
I mean, Ramp's raised $1.9 billion, so it's just gonna keep consuming this capital for one reason or another, right?
Speaker 0
Mm.
As I say, you can actually work it out if someone had the time. I used to have the number in my head. I've heard they're doing roughly $700 million to $800 million. Interchange is a good slug of that. You get 2% to 2.5% on interchange, so you can work out their total transaction volume, and you have an average, probably, of a 15-day revolving balance.
So you probably have 4 to 5 times revenue in terms of floating cash amount. In other words, to do $700 million in revenue, you might have a $3 billion to $4 billion capital requirement because you're floating all these—I mean, you're replacing Amex, so you're floating all these guys on their credit cards. So you do need the money.
Speaker 3
I get 20 emails a week from Brex telling me to deposit more in my account. Maybe it's not a coincidence. I'm constantly—
Speaker 0
Yes.
Speaker 3
Constantly, “Jason, your balance may go below $2 million. We need money instantly today.” I'm like—
Speaker 0
Yeah, totally.
Speaker 3
“Leave me alone, guys.”
Speaker 0
Yeah, because it's—
Speaker 3
Just let me be. I'm fine.
Speaker 0
That's exactly right. No, I mean, in the end, fintech companies are finance companies. One of the non-negotiables is to have low-cost capital, and at the moment, bizarrely enough, venture equity is lower-cost capital than pretty much anything out there, as Jason said. Two percent dilution or get a banking license? Hmm, I'll do the 2% dilution. You know?
11. Why CRV Chose Focus
Harry Stebbings
Now, the final one that we have to discuss—I thought this was really interesting, just going back to venture land. CRV raised $750 million, shrank its team, and is not raising a late-stage select fund. Is this a sign of a more rational venture landscape? Is this a sign that LP appetite is less willing to back opportunity funds? How did you guys think through this one?
Speaker 0
I think they do early-stage well, and they probably decided the best way to make money is to do the thing you do well, do it well, and keep the message clear. I actually thought it was very smart of them. There are some firms that are pulling off these multi-platform strategies, but it's just a step-function increase in complexity.
If you can do it—and obviously we all know the names who have—great. You have a multi-product firm. But if you're gonna be marginal at it, the non-negotiable thing is to at least do one thing well. CRV clearly decided that rather than muddying the waters trying to do this multi-strategy thing, they should just execute really well on great early-stage investing.
It was probably smart in a world where you just wanna have a clean message. To your comment on whether it's a sign of wider LP appetite: no. I think what you're seeing is that LP appetite is varied. You can say, “Hey, I'm really glad, CRV, that you focused your message down,” and the next day you can say to Founders Fund, “You've got the most amazing growth-stage fund on the planet. Let me give you another billion.”
The day after that, you can say to Elad Gil, “You're just amazing. Let me give you $1.5 billion on your own.” Maybe the takeaway is the whole industry has changed so much that there are a lot of different ways to play the game, and more than anything, what they wanna see is that people know what game they're playing and play it well.
By CRV saying, “Hey, this is what we do, and we're doing it well,” you can say, “Okay, I know what I'm getting from that.”
Speaker 3
Look, the other thing is we're in an age of everyone raising as much capital as they can and deploying infinite capital as startups stay private forever.
Speaker 0
Yeah.
Speaker 3
But deep down, if you're in it for carry over fees, you wanna get into carry mode faster. I'd rather have 2 $750 million funds split in half, like Founders Fund did, than 1 $1.5 billion fund. It's better for GPs, isn't it?
Speaker 0
Yes.
Speaker 3
I'd rather get into carry mode faster.
Speaker 0
Totally.
Speaker 3
I don't know CRV's results, but they've had some good investments. If they're looking at their results, especially some partners who maybe generated more carry than others, they're like, “I'm not in it for a million bucks a year, $2 million a year in salary. I'm in it for big carry checks, and I wanna get this thing deployed in 24 months, 30 months,” right?
I know that we've lost this in the last 18 to 24 months, but if we look back on all of Harry's guests, in normal times, you wanna optimize your fund size to achieve the maximum carry you can in a given time, right? And then just go raise another, right?
Speaker 0
Agreed.
Speaker 3
In an ideal world, you might even raise a fund a year so you can get into carry mode as quickly as possible. You lose a lot of things. You lose time and other things, but you wanna get to carry mode fast. You don't wanna leave it all to your grandkids, do you?
Harry Stebbings
Jason, do you regret doing an opportunity fund?
Speaker 3
I don't regret it because I'll make money. So listen, it wasn't worth it for me to do the opportunity funds. It's not enough.
I'll make 15% more money. It's not enough money. If I had a $500 million opportunity fund and could deploy it, that'd be different. So maybe CRV looked at it, and maybe they did some of their deals that didn't make a lot of money. It was a lot of hassle, and they're like, “Hey, I only made 10%, 15% more carry. My LPs don't love it because I burned a lot of capital from them. Let me concentrate where I make a lot of carry.” That's my guess.
And for me, Harry, it's the same thing. Ninety percent of my carry will come from the main fund, so I'm like, “I don't want the drama in my life.”
Speaker 0
Agreed.
Speaker 3
So, I'll still make maybe 3X, but that's it.
Speaker 0
Interestingly enough, I think a lot of the math runs out there because you look at it and you go, “How many deals do you have in your main fund? How many of them are amazing?” Maybe only 20% of them are amazing. How many of them can you deploy late-stage dollars in? Maybe only half of that, because late-stage rounds get pricey very quickly.
It turns out that unless you end up with one of the very few companies that are not just amazing but super amazing, where they can be a $20 billion outcome, your ability to deploy lots of capital relative to your early-stage fund is actually much smaller than you think. So, the size of the opportunity fund that you can deploy just within your entities is smaller than you think. And you're right, Speaker 3, then you end up saying, “Is it worth it?”
Now, you can decide, as some people have, “No, I'll build a whole late-stage growth strategy and then knock yourself out.” You can do anything and you can put billions to work, but then, at that point, you're becoming a different thing.
Speaker 3
Plus, maybe less discussed—maybe CRV's too big for this—but almost every seed manager that we know that's been successful can spin up an annex fund. It's not so simple. If all of a sudden you got into Anthropic early and it's turning out pretty good, you could raise a couple hundred million dollars in an annex fund or an additional fund. It's okay. It's not a permanent decision not to raise another vehicle.
Harry Stebbings
Do you not think, though, Benchmark's capping or discipline on fund size is one of the core reasons why it's been a challenging year or so, in terms of their competitors scaling, gaining relevance, and Benchmark being a little bit left behind?
Speaker 0
I don't know if I agree with the characterization. I think they've had—actually, either you or Jason did the list last time.
Speaker 3
Harry did it.
Speaker 0
Harry did it. They've done amazing deals. If being left behind is that set of deals that they've done, I don't think that's challenging.
Speaker 3
But you're both right.
Speaker 0
Yeah, I know.
Speaker 3
But you're both right, right? The numbers—they've picked extremely well, incredible investments. At the same time, if you look on social media, Benchmark isn't listed the way Andreessen and Sequoia were a generation ago. It's just not. Does it matter? Harry's built a big brand. He's concerned it matters. You could argue both sides.
But when the industry was smaller and Brian Halligan had to drive up and down Sand Hill to get a deal done and it took months, brands were just different. It's still an S-tier brand, but it's not in every conversation on X, right?
Harry Stebbings
Yeah.
Speaker 3
It's YC, Sequoia, Andreessen. That's it, really.
Speaker 0
Totally.
Harry Stebbings
And if you were scaling fund size and scaling strategy, would you be able to keep the likes of Miles and Victor, who are obviously great investing talents?
Speaker 0
I think it's presumptuous. I'm not going to tell Benchmark how to run their business. I remember them starting in '95 and talking to them then. They've done a pretty damn good job of running that business. They don't need my help.
Stepping back from the individuals, the meta question you're asking is: Is the very best specialist fund able to compete in this market with the very big, full-stack firms? That's really the meta question. I'm willing to stipulate, and there's a lot of data that says it, that Benchmark have been among, if not the best specialist fund.
So, I think this takes it away from individual commentary on people, which gets personal very quickly, and moves instead to the meta question you're asking: Is the right strategy a specialist fund, or do you need to be a full-stack player to matter?
Speaker 3
Yeah.
Speaker 0
And there's no doubt that if you're full-stack, you have more coverage, you have more news, you have more news flow. I cited the data from the Rotman guy at DST a while back. Your picking goes down a little, but your volume goes up. I don't know. Each side has a risk.
The risk you face as a specialist is you get crowded out by the noise and people don't know you're amazing enough, and therefore you lose some of the at-bats to the people who have more brand. The risk you face as a brand is, in your wild urge to put all the money out, you end up overextending yourself and you get subpar returns.
You fast-forward 5 years and you look back and you go, “Oh, we had lots of noise, lots of good individual deals,” but as Jason said, it didn't add up to compelling returns because we had so many other deals. I think the truth is both strategies will work if executed well, and both strategies have their risks.
I know that's kind of a stupid answer. It is, but I think there's lots of ways to make money. The one thing you don't want to do is be inconsistent. You have to have a strategy that plays to your strengths and that can work for you, and you have to understand the risks that your strategy entails, including the risk of a specialist strategy. We see it every day.
Look, when you're competing against the guys who have infinite deals, infinite deal flow, and infinite money, it's hard, and sometimes you lose. Equally, for those guys, sometimes you put $100 million in something and it just doesn't work. Unless you have an outlier to cover all those mistakes, that's going to be their problem.
Harry Stebbings
Guys, I want to wrap up with one final question, and it's this: We had Halligan today. He was fantastic. Who would you most like to have next time?
Speaker 3
I think it would be great to have Marc Benioff. I think he would do it. He'll be different than Brian, right?
Speaker 0
Ooh.
Speaker 3
But my idea that I didn't have until today was—Jeff Lawson would be great.
Harry Stebbings
I thought the same. I thought Jeff would be fantastic.
Speaker 3
Didn't occur to me until today.
Harry Stebbings
Yeah.
Speaker 3
I would love to hear all of his reflections, all of his thinking. I mean, he's a founder's founder. It hadn't occurred to me. It's a great idea, right?
Harry Stebbings
Totally.
Speaker 0
And how would we, in fairness to him, not make it just be everything you learn from getting fucked up? You want the activist story, but you don't want it to be a celebration—
Speaker 3
But he's rebuilt. He's got a whole AI incubator and Dogpatch. He's got a lot of stuff going on. He's rethinking everything from his stack in the age of AI, right?
Speaker 0
Perfect.
Harry Stebbings
Yeah.
Speaker 0
Okay, good.
Harry Stebbings
I love it. Let's go for it.
Speaker 3
He's great.
Harry Stebbings
I'm going to do Jeff and Benioff, and we'll get them on in the next few weeks.
Speaker 0
Oh, I'd be scared of Benioff. He'd scare me.
Harry Stebbings
Oh, no.
Speaker 0
He'd scare me.
Harry Stebbings
It'll be fine. Benioff's great. He'll just talk about Agentforce. I mean, what can I say? We deliver fast. In the last 24 hours, we have confirmed Benioff and we have confirmed Jeff Lawson to do the show next with us. It will be a fantastic set of guests. I so enjoyed that, as always. If you wanna see more, you can find it on YouTube by searching for 20VC. That’s 2-0 VC on YouTube. 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. 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. You wanna grow your company, right? But instead of having the time to get to the next level, you’re stuck maintaining the status quo. It’s freaking maddening. Well, HubSpot’s customer platform, it actually solves this. Breeze. No, it is not a fabric refreshener. This is the next generation. Their built-in AI takes over all the busywork. It writes emails, it qualifies leads, it answers common customer questions, and even help create content. Also, your marketing, your sales, your service teams can focus on what matters most, and the impact is undeniable. Teams are saving 750 hours a week. One even increased leads by 251%. And these results show up in days, not months. Over 238,000 businesses already use HubSpot, so join them. Visit hubspot.com/ai. As always, I so appreciate all your support, and stay tuned for an incredible episode coming tomorrow with the one and only founder of David’s Protein Bars.