HubSpot co-founder Brian Halligan on coaching AI-era CEOs, the rise of 'five-tool' founders, and his new Sequoia podcast

Speaker 1: Because me and Jordy, it's every day for us over here. We're in the trenches.

Speaker 7: I'm very checked in.

Speaker 1: Okay.

Speaker 7: I come at it from another angle. Yeah. What I've been doing for the last year is I'm like the run an in house CEO practice at Sequoia.

Speaker 1: Yeah.

Speaker 7: And I do three things. I coach CEOs, most of which are building companies on top of the AI wave, all of which. I create communities of CEOs so they can collaborate together. I have a kids table of CEOs of kinda small company and an adults table of CEOs in large companies. Mhmm. And then I'm creating content. So I've got a podcast. Launch is tomorrow.

Speaker 1: Oh, let's go.

Speaker 7: Yes. About CEOs and how to be a CEO.

Speaker 1: I love it.

Speaker 6: How do you

Speaker 1: go from

Speaker 7: start up to scale up? Tune in tomorrow.

Speaker 2: Fantastic. What what's what's the format? What's the format? Is it is it guest driven? Is it, is it turning kind of the lessons that you talk about at the kids table and at the big kids table?

Speaker 1: It's a six hour daily livestream, actually.

Speaker 7: Exactly what

Speaker 1: it is. It starts it starts at 9AM and and ends at 3PM. Makes The Us look

Speaker 7: basic thesis is, like, the playbook I grew up running HubSpot from 2006 to 2021. Like, a lot of those plays don't seem to work as well.

Speaker 12: Sure.

Speaker 7: And the getting like, the Rubik's we thought, like, for example, I think what's how the way Jensen Huang runs this company is super interesting with 60 direct reports and no one on ones and kinda public criticism. The way Elon runs his company, his empire is really interesting. The way Brian Chesky does it is quite interesting. And I noticed all these CEOs have kinda new place, and they've got a new perspective on things. And so I'm inviting them on kinda one by one to chat about how did you become a CEO, how do you like your job, what are the best practices, what is all wrong about CEOing these days, and I think it's first guest is Parker from Rippling tomorrow.

Speaker 2: Nice.

Speaker 7: And it's a good one because Parker gives all the tea on getting fired by David Sacks from benefits, all the tea on the drama with Deal on Spygate. And then in between all that, he is a very, very thoughtful CEO. He's not a big fan of conventional wisdom as people know, but he he's doing some really cool stuff. So that's kinda episode number one tomorrow.

Speaker 1: Yeah. I like that framing as, like, focusing on the actual job of the CEO because there there's there's there's other shows that could do, like, okay. Let's do the product review. Let's let's do the product announcement. But having one feed where you can go and actually understand the philosophy of a whole host of CEOs. That's fascinating. Jordan? I think

Speaker 7: it's What? I think Sorry. I think it's kind of interesting because I was the CEO for so long. So it's like, I'm really journalist. It's like a conversation about what the hell is really going on here.

Speaker 1: Yeah.

Speaker 2: Yeah. How did your approach evolve over the fifteen or so years that you were CEO of HubSpot?

Speaker 7: I don't think it evolved that much is the interesting part.

Speaker 2: You just one shotted. You just

Speaker 7: I was basically the same guy from 2006 to to 2021. And but and I followed, like, ye old playbook of the way people run companies, like the Bill Campbell style playbook. And that's what I think is interesting. It's kind of changing, and that's what I'm trying to dig into and kinda go deep on. It's like Stanley Tucci. You know, Stanley Tucci show when he goes to Italy and he's trying to find his roots. Yeah. I'm searching. I'm searching.

Speaker 1: Fantastic. What are your thoughts on

Speaker 7: You wanna know some surprises?

Speaker 1: Yeah. Please. Yeah.

Speaker 7: Okay. Couple things. There's a there's a breed of CEO that I see a lot of these days that I call a five tool CEO. I'm a big baseball guy, there's such a thing in baseball as a five tool player. Somebody who can hit, somebody who can hit for power, somebody who can catch, somebody who can throw, and somebody who can run at an elite level. Very, very rare in baseball.

Speaker 2: Who's who's an example of a of a modern five tool player?

Speaker 7: Shohei A six tool player is Shohei Okay. Yeah. He can do he he can actually run. He can hit. He can hit for power. He can throw. He can catch. Yeah. He's a very talented and very unusual cat. Alex Fregman's one of those on the red some red sets guy. But there's a bunch of these folks who kinda remind me of that in in the software industry where they've got vision, they can code, they can design, they can recruit, and they can sell their product. And they're and that's I think what's pretty rare in software, they're all over the place now. And they're getting funded, and I work with a bunch of them. Just a few examples, like Parker's one, for sure. Brett Taylor, for sure, from Sierra's one. Gabe Stengel from Rogo, kind of a new company's ripping is one. Matti from eleven Labs. I have no idea how to say his last name. Karim from Clay. Dara from Delphi, like, on and on and on. I'm super impressed with the new breed that's coming out and how talented they are.

Speaker 1: Who do you think the Barry Bonds of business is or the Mark Maguire of business? Fantastic performance as a CEO, clearly using performance enhancing drugs.

Speaker 7: If someone if someone tapped me on the shoulder and said, you know, I don't know if you heard this, but Elon's actually an alien

Speaker 1: Oh, yeah.

Speaker 7: And be like, man, that that kind of that puts

Speaker 2: That's trash.

Speaker 7: You know, would you guys be surprised if someone said, it turns out he was an alien? Would you guys be like, oh, no. No. No. No. No. That's that's crazy. You'd you'd be like, yeah. Maybe.

Speaker 1: It is it is funny the performance sensing drugs thing because, like, the majority of jokes about how it's not illegal to be on a stimulant. I obviously partake in in caffeine, the legal stimulants, but some folks, go a little bit further. But the reason that it was so controversial and so illegal in baseball is because isn't baseball a sanctioned monopoly by the government? I believe that's I believe that's why. And so that's why during the whole baseball scandal, the steroid scandal, they came in and they had to do, like, a hearing in on Capitol Hill. It was a crazy, crazy moment. I don't know if you tracked that.

Speaker 7: The the I think the real reason is because they've been around for a hundred and fifty years. People who broke records in the nineteen twenties, like Babe Ruth broke important records in the nineteen twenties, that you can have, like, a ranking of who's actually done the most home runs, best batting,

Speaker 1: all these

Speaker 7: different things. You can't do that in basketball because they change the rules so much. You can't do that in football if they change the rules so much. That's why they were so resistant to change the rules in baseball, and that's why they were so up in arms about the steroid thing.

Speaker 1: Yeah.

Speaker 7: Yeah. But I do think founders do the equivalent. Like, when I was growing up, I'm a beer drinker. You know? We went out the team, definitely tied it on. You go to you go to a Sequoia founder dinner?

Speaker 1: Yeah.

Speaker 7: First of all, it's at 05:30.

Speaker 1: Oh.

Speaker 7: Kinda, like, early. And everyone has a salad, and it has water, and then is back in the room coating by 07:30. That's definitely not how I grew up.

Speaker 2: Yeah. Yeah. Yeah. Do you think beer do you think beer gave you an edge back in the day?

Speaker 7: I I I don't think beer gives anybody an edge. I think it helped me connect with some employees along the way for sure, particularly salespeople.

Speaker 1: What do you think about co CEOs? Yay or nay?

Speaker 7: Okay. I I think I Sandhill Road is very negative on this.

Speaker 2: Last Except on stewards. We have co stewardship.

Speaker 7: Yes. We can talk about that too.

Speaker 1: Yeah.

Speaker 7: But I talked about this on one of the pod episodes with Vlad Tenev. He was a co CEO for, like, the first seven or eight years of the company, and I was very surprised to hear that. And he was very positive on it. I think you can do it. I think it's a little dangerous. You better know the person very well and be able to finish your sentence. Like, my cofounder, Darmesh, and I, we weren't co CEOs, but we ran it like a partnership. And we thought of it like a partnership, and the employees thought of it like a partnership. If we called ourselves co CEOs, that would have actually worked quite fine.

Speaker 2: That makes sense.

Speaker 7: Yeah. Want some other things that surprised me?

Speaker 1: Yeah.

Speaker 7: Here's the weird thing. Two of our most successful entrepreneurs of our generation are Jensen Huang Yeah. And Elon Musk. And they've obviously got really unique play playbooks. Like, Jensen's got his 60 direct reports, and the no one owns all this stuff we just talked about. Elon has his has his algorithm, and, like, he credits the algorithm with a lot of his success. I ask all of the CEOs on the pod, like, who's on your Mount Rushmore? Who do you follow?

Speaker 1: Mhmm.

Speaker 7: Like, who's your inspiration? For me, it was Steve Jobs. Like, my generation is Steve Jobs. None of them really say, you know, Jensen. Like, no one's copying their playbook. No one none of these CEOs have 60 direct reports, and not a single person has mentioned the algorithm. I think that's quite odd. Do you?

Speaker 1: Yeah. We actually polled YC founders in the last demo day. We asked probably 20 or so who was their favorite entrepreneur, like, they look up to. And, I was expecting, like, half to say Elon and Yeah. Maybe, you know, a third to say Jensen, something like that. Just like vanilla market cap. It's a question. We didn't prep them. We didn't tell them we were gonna ask them this. This is off the top of their head. And there were maybe, like, two or three Elons, but it was all over the place. Yeah. And it was it was way down the stack. I mean, there were some people who are like, the the founder that I look up to most is is, like, a, like, a founder who started their company five years ago and is a unicorn now, but, like, certainly not, like, one of the greats. Like, obviously, like, doing doing fantastically, but, like, you know, this is like a series b or series c level founder. And they're like, that's who I actually look up to.

Speaker 2: I don't think I don't even think a single person said Jeff Bezos.

Speaker 1: I don't think anyone said Jeff Bezos.

Speaker 2: A guy with a 120,000,000,000 of of $20.24

Speaker 1: Free free cash flow. Even yeah. Yeah. It was crazy. It was it was much less concentrated in the mag seven than I thought it would be. And I don't know if that's a shift in in how younger entrepreneurs or newer entrepreneurs are thinking about what success looks like. Like, the maybe the downstream critique of, like, the the teal monopoly thesis is that, like, it's actually really hard to go start a business that is in the social networking category or in the online commerce category. It's just harder to do that. And so, maybe people some people read zero to one, and they said, hey. I gotta start a company. But then other people read zero to one and says, hey. I I better not I better not set my sights too high because, realistically, how am I going to compete in, you know, some of these monopolistic categories that have been truly dominated by the hyperscalers? It's gonna be hard for me to go zero to one in those categories. And so I need to maybe find a smaller market. I don't know. Maybe it's a trend.

Speaker 7: One of the things that surprised me about them is they don't really have anyone that they're really following or looking up to. They're very much their own people. Mhmm. And they're kinda making it up as they go, and they're and they're writing the rules kinda based on what they think makes sense. They don't have like, when I grew up, I had two people. I have two CEOs. Jobs

Speaker 1: Mhmm.

Speaker 7: Jerry Garcia. Those were my my two heroes that I tried to base my behavior around.

Speaker 1: Yeah.

Speaker 7: And they they, you know, they were my courses. These guys don't have courses. The other thing that's interesting about all of them is, like, be yourself, everyone else is taken. They're all very, very, very different homo sapiens. Like, Vlad Tenev is very, very, very different from Parker at Ripley. Anton from Lovable is very different than Matti from eleven Labs. They are all quite unique, which I I like to see that. And they're and they're they're their own people. They have a lot of agency.

Speaker 1: Are you

Speaker 2: interviewing anybody that runs their company remotely?

Speaker 7: Nobody's doing remote. Everybody is in the office. Remote is dead.

Speaker 1: Remote is dead.

Speaker 7: And everybody talks about 996. I think there's a lot more talk about 996 than walk on 996. I don't think very many people actually doing it. The CEOs are, though. The every CEO I talk to is under a like, I say, what's your stress level? One to 10? Almost all of them say 10.

Speaker 1: Yeah. What do you think about this idea that a lot of companies are nine nine six ing in a hybrid sense that because the tools have gotten so good I mean, a software engineer can fire off a prompt at home on their phone that will go and, you know, start doing work that gets reviewed in the morning. I I'm I'm firing off a deep research prompt for something that we are gonna talk about on the show. Yes. Tomorrow. And so there's this, like, ambient level of remote work that's happening on top of the in person work that's happening. And so I might if I were to push back, it might be that, remote is not dead. We said yes and. We said, let's go back to the workplace. Let's work in the office, and then let's also work remotely at home on Saturdays, on the nights and weekends, because that's what it takes to win. And so the nine nine six thing is happening, but across two two spaces.

Speaker 7: I'm a little I totally buy that so much work is asynchronous now. Yeah. I just think, like, we went remote at HubSpot pre COVID, and, like, the culture's great. It's still great, but you lose something. You lose. You definitely lose something. So I'm very supportive of the announcing. Like, if I were starting a company today, I wouldn't do remote. You know, your headquarters is San Francisco. San Francisco is a bearable place to scale a company. Salespeople are hard to find and really expensive and not loyal. Developers are even harder. And so I do a big hub in San Francisco and then another big hub, let's say, in Toronto where there's a lot of salespeople and a lot of developers Mhmm. And be like, we're in office and or at least four days a week. I think that's a good call. Ironically, the people who I think that CEOs who I think are the hardest core are the two European founders I interviewed, Anton from Lovell and Matti from eleven Labs. Like, they are seven days a week. They expect everybody in the office for seven days a week. Those two are the hardest core, even more so than our American brethren.

Speaker 1: Well, the pressure on them is immense because people have such so low of expectations for Europe. So Yeah. You know, they have to deliver for their country. It's really it's really high speed for them.

Speaker 7: Is kind of patriotic

Speaker 1: Yeah. For sure. Of course.

Speaker 7: Of course. Need to

Speaker 1: lead the thing. Talk about the stewards I wanna call.

Speaker 2: One second. I I was curious. You said, the CEOs you interviewed, all of them or the CEOs you talked to, all of them say their stress level is 10 out of 10. For the most part, they do. Fifteen years running HubSpot. When was your like, what what did does that resonate? Was it kinda steady state 10 out of 10 the whole time, or did you at some point figure out a motion that allowed you to maybe hover at, you know, a seven, which is maybe like a healthy amount of stress?

Speaker 7: It was pretty close to 10 the whole time. Just Most of this

Speaker 2: white knuckling it.

Speaker 7: Just It was pretty stressful. Like, the whole thing was stressful. And and, like, the thing with HubSpot in most companies, like, looks pretty smooth from the outside, but it was, like, two steps forward and, like, one freaking giant step back and two steps forward, giant step back. You're stepping in it. And in HubSpot, like, we were kind of a wartime company. Like, I like Ben Horowitz's book, and he's got a whole chapter on wartime versus peacetime CEOs. All of these CEOs are wartime all of the time. And if they don't have a war going on, they kinda create a war. I thought that was kind of interesting. It's a wartime era. The only CEO I interviewed that is not, like, 10 out of 10 stressed is Nikesh from Palo Alto Networks. He's a cool cucumber.

Speaker 1: Yeah. I wonder why. I mean

Speaker 2: Yeah. He's a

Speaker 1: cool He's, like, so secure.

Speaker 7: He doesn't he doesn't work. A lot of these guys are wrong.

Speaker 1: Mean, really yeah. Like, this has more, like, strength of strength of market position. Right? Like, if if you are running a company where Sam Altman's out there being like, I would love to eat off of your plate. I would love to launch a competitor. And then, like, Sacha Noodella is like, oh, yeah. We're gonna do that too. Like, you better be operating at a 10 out of 10

Speaker 2: stress off.

Speaker 1: Sam Sam you're gonna get cooked.

Speaker 2: Sam competing you know, effectively competing with Microsoft while Microsoft has all his IP, and he has to give him 20% of his revenue, and he's gotta pay him a quarter

Speaker 1: It might be quarter

Speaker 2: of a trillion over the next few years.

Speaker 1: He might he might come for your for your nice little startup. You know?

Speaker 7: Virtually every company I'm just looking down my list of kids stable, adults stable. Virtually all of them are extremely nervous about what I'm gonna ask him to do. Yeah. Of course. It's a a long conversation at every board meeting.

Speaker 1: Of course. Of course. The the Stewart thing. I'm so interested. Like like, why doesn't Sequoia just have one CEO? Why don't they have a, you know, like, a super GP, like a head partner named named partner? You could just rename the fund. Kleiner was doing that for a while with Caulfield Byers. There's so many different ways to approach it. The Blue Owl we were talking about earlier, they have two co CEOs, and I think they have three co presidents. You know, these names kind of mean nothing, but they also have extreme weight. So what is what is a steward in the Sequoia Capital context? Why not CEO? Why not president? Why steward? And then what does it mean to have two now?

Speaker 7: Okay. I like the I actually like the word steward because, you know, Don Valentine started and Michael Moritz and and Jim Getz and Doug Leone. Like, it's been a long line of really strong leaders in Ruloff that they've handed it down to. And the thing that's interesting about Sequoia, so I've been in there for a little over a year, is they are not at all, like, even remotely resting on their laurels. They are paranoid. They are aggressive. Mhmm. They don't wanna blow it. And so steward is actually a decent word. The the in this particular case, I think Ruloff was ready to move on. He wanted to move on on top, and the there were just two really obvious candidates. Alfred Lin's got an incredible track record. He runs the early team. He's a good leader. Pat Grady's got amazing track record, runs growth team. Like, picking one of those would have been tough. They work well together. It's like, let's give it to them both. And I think Sequoia has done that kind of thing in the past, so it's not unprecedented. And I I think it's gonna work well. And they don't call themselves they call themselves stewards, but internally, they're like, just call us partners, and they've made a big deal out of that, which I think

Speaker 1: I imagine that they go around the office saying, you have to call me steward Lynn now. You have to call me steward Grady now, And also don't make eye contact with me.

Speaker 7: Yeah. There it is.

Speaker 1: And I will wear I will wear long flowing robes. No. It yeah. It's just it's just interesting the the actual, the actual aesthetics of it. I mean, we don't need to get into the actual dynamics of the of the changeover from Rohloff to, the the co stewards. It's just I I wonder if if a co CEO dynamic is sustainable or if it is an audition process for the final boss, the final CEO.

Speaker 7: I mean, it hasn't worked a lot. It it I mean, Netflix is doing it. Spotify is doing it, but you can't think of a lot of examples. And it looks like it kinda works with Netflix. Like, that's been going on for a while, and it's doing pretty well.

Speaker 1: Yeah.

Speaker 7: I mean, Spotify is really there's just not a lot of precedent for it. So I don't know. It wouldn't be my first choice to to be a co CEO or to fund a co CEO. Yeah. But in some cases, it can work. I think it's a little unorthodox.

Speaker 1: There is an interesting dynamic where

Speaker 7: They call it a partnership for a reason. Yeah. You know? It's not a corporation. It's a partnership. And so that vibe has stretched over five decades for these folks.

Speaker 1: Yeah. I wonder I wonder the benefits of having two people in the same in in the role, like, it becomes less pressure for one person, but then you also don't have necessarily, like, the buck stops with one person. There's all these, like, odd dynamics. Like, there's benefits and costs to to having, the do the That's right.

Speaker 7: I think they can get a lot done, and they can divide it up and get a lot more done. That was the case with my cofounder and I. Like, we divided a lot of stuff up Yeah. And we got a lot of shit done together in in our respective parts. And I deferred to him a lot. He deferred to me a lot.

Speaker 1: What do they call it? Du duarchy, where there's two kings. Monarchy one key. Duarchy is two kings. Very rare.

Speaker 2: How have you been processing this new wave of AI agent startups that are, in my view, oftentimes competing with traditional SaaS companies that may have only been started a few years ago? How how have you been processing it?

Speaker 7: Well, I'm I'm involved with a lot of them. That's I mean, they have escaped the gravitational pull of the of the Earth's revenue. Like, holy crap, where they're going fast. And HubSpot grew fast in its day, and and it's like, wouldn't even get a second look from a VC now. And it's remarkable what's going on. And I tweeted a a week or two ago that, like, it's a bubble. If you get an offer to sell your company, should do it. You should take money off the table. And on one on one shoulder, I'm like, it's definitely a bubble. The valuation is crazy, 100 x and whatnot. On the other side of my shoulder, like, I just have never seen in the history of mankind growth like this, so maybe it's not. I don't know. Where do you guys come out of that? Are we in the middle of a bubble or is it just match the growth?

Speaker 2: I think we've had a you know, we talk with a lot of investors and sometimes we get a little concerned when people come on and say they don't care at all about margins. We worry a little bit bit about those clips ending up in documentaries about, you know, whatever whatever this moment in time has up there.

Speaker 1: You're either in a bubble or you're in a crash, and we're definitely not in a crash right now.

Speaker 2: Yeah. I get I get I get I would say I get my concern comes from companies that spring up and are raising because they're positioning their product as this, like, AI agent when in reality, it's hard

Speaker 4: to

Speaker 2: tell why it's gonna be a better solution oftentimes than something that looks like a a a normal SaaS product. And so I just get I get concerned because I know that the the SaaS companies in their category are have access to all the same tools and they have distribution and they can potentially use the advantage they have of having this big product surface area and a bunch of core existing product and then just compete on all these new product lines. And and I just wonder if if some of these, like, age AI agent, these more native AI companies will struggle to actually compete with, and and you've seen this. Like, it's not like com companies like Notion, for example, didn't sit around and say, like, no. We're not gonna integrate LLMs into our product. Like, that seems cool, but we're just a we're we're, you know, a notes product and and we're gonna stick to handwritten text. Like, were incredibly quick to integrate all the best models into their product. And so I just don't I don't see, like, the most recent generation of teams, like, asleep at the wheel at all.

Speaker 7: Yeah. And I'm old enough to remember the last platform shift from client server to SaaS. The client server companies were very much in denial of SaaS for a long time. I remember Oracle just being very vocal that SaaS is it's a bunch of BS. And obviously, SaaS did very well. Some of those folks did well, and they and they came across. SAP did pretty well. Oracle did pretty well. Oracle did fantastic, actually. The thing that's different this time around is all the SaaS players, including HubSpot, were very early on it and are investing heavily in it and are building cool stuff. And they have a little bit of advantage, and they have a lot of data and a lot of context, which is really useful if you're building agents. So I wouldn't I don't I I think SaaS is alive and well, and I think a lot of these SaaS companies, HubSpot, ServiceNow, and Ocean, so many of them are building cool stuff. Like, inside of HubSpot, I think of it as like a platform with applications and agents. You can build agents on it. You can use our agents, and then it's got a a Copilot that you can refer to. It's all starting to work. People are using it. The thing that's interesting about some of these Asian companies is they're working in areas where there's there weren't SaaS companies. Harvey is doing incredibly well. It wasn't really a you know, it wasn't an area with a lot of big SaaS companies in there or Rogo selling to investment bankers. Like, a lot of a lot of the early huge wins on the agents are in funny areas. This company called Juicebox, absolutely ripping, is in recruiting areas where they're like a big incumbent. Like, they're filling in the air.

Speaker 1: Yep.

Speaker 7: And some of them are sort of be working alongside of it, and some are autopiloty. And the autopilot ones, I think, will be the ones to really watch.

Speaker 1: Yeah. It feels it feels really hairy for Microsoft to go after legal AI just because that's not really they they sell mostly general purpose tools. And so if you're building an Excel plug in or you're bringing AI to Excel, I'm worried a little bit about where that goes. But if you're building something that, yes, it ostensibly is a Word document, but your entire business is off in this industry that's heavily regulated and Microsoft has only penetrated with the broad tools and has never really built a vertical solution in that category, I I feel much less worried about you being attacked from the labs. But thank you so much for

Speaker 2: taking the time fun.

Speaker 1: To chat with us.

Speaker 2: Excited for your I'm excited for your new show. Excited to check out the first episode.

Speaker 1: And the number of stewards at, at Sequoia is doubling. So, any day now, you might get the tap of the shoulder. Be the third, fourth, fifth steward. They're adding more stewards every day, and we're pulling for you.

Speaker 7: See you, guys.

Speaker 1: See you. Cheers. Google AI Studio. Create an AI powered app faster than ever. Gemini understands the capabilities you need and automatically wires up the right models and APIs for you. Get started at ai.studio/build. Our next guest is doctor Fei Fei Li from World Labs. She is a world renowned computer scientist. Thank you so much

Speaker 2: Welcome to the show.

Speaker 1: For taking the time to talk to us today, and congratulations on the launch.

Speaker 2: Massive.

Speaker 9: Hi, guys. How are you?