Long Strange Trip: CEO to CEO with Brian Halligan
00:49:44 · Luca Ferrari, Brian Halligan
[00:49:44] S0: Yeah, absolutely. I mean, look, as I said earlier, it's almost like if you're coaching or running a sports team, I think it'd be a fool saying, well, the way to win is this and that and that's the only way to win or the best way to win no matter the people you have on the team, right? So the players. And so yes, I mean, if and when we we change our CEO, I would encourage her or him to see whether any change is warranted. I mean, they don't have to change anything if they like it the way it is, but they equally they should feel free to change things if they thought that would improve things. [00:50:21] S1: Okay, Just from talking to you, you're a very first principles person. It feels like kind of a big skepticism of conventional wisdom. That was sort of the same way back in the day. What is conventional wisdom right about that you do? That maybe you're like, this is wrong, we're going to rethink it, but on our wheels, we should just do what everybody else does.
00:50:21 · Brian Halligan, Luca Ferrari
[00:50:21] S1: Okay, Just from talking to you, you're a very first principles person. It feels like kind of a big skepticism of conventional wisdom. That was sort of the same way back in the day. What is conventional wisdom right about that you do? That maybe you're like, this is wrong, we're going to rethink it, but on our wheels, we should just do what everybody else does. [00:50:43] S0: You know, we've tried to build this company from the ground up. Yeah, questioning everything not because we thought we knew better, but because we believe that. So we had this ambition of building one of the most successful companies of all time knowing full well that we would very likely not succeed. But we thought that if that were if that was the the how high the bar was going to be, the only chance we had to achieve that level of ambition was to do something differently. If you emulate what everybody else is doing, you're guaranteed to be approximately mediocre, I mean, little bit better, a little bit worse. And so we never even bothered understanding what conventional wisdom was, we just tried to for each important problem, we just tried to find the optimal solution given our particular context and vision. So yeah, I know, I'm sure there are plenty of things in conventional conventional wisdom that makes sense. I don't know, like being nice to people, I guess that's, I agree.
00:51:38 · Brian Halligan, Luca Ferrari
[00:51:38] S1: One thing that's kind of interesting that people ask me about all the time is AI native companies seem to be running a little bit different than companies founded before ChatGPT. You're kind of famous for simplifying things. So I want to hear about that. A lot of people are just doing a lot of stuff at once. In year two, they're going international and year three, they're starting, they're acquiring a business. Like Things are just moving so much faster. Stuff that took HubSpot eight years, people are doing in the first couple of years. And then HubSpot, I was a big simplification guy. I even got myself a no hat. [00:52:12] S0: Oh, that's awesome. [00:52:13] S1: I go to a big meeting. Good thing about HubSpot, everyone's got great ideas. We should do this or this. And I would always, we're definitely a company that was much more likely to die of overeating and starvation. And so I bought this for everyone in the no hat. Things seem to be changing. I've noticed these companies, they're wearing yes hats and they're getting a lot done and they're pulling it off. What's your reaction to that?
00:52:38 · Luca Ferrari, Brian Halligan
[00:52:38] S0: It's certainly a winning strategy to be a radical simplifier Because complexity means costs means being slower, being worse, generally speaking, but there's no but the perfect balance depends on, your particular context. Obviously, if you were to build a business, let's say in the 1800s, with no technology, no internet, know, probably a labor market that was way less efficient. Clearly, you you should at the time you should have chosen to do a lot less than you know, would have been reasonable in the 1990s. And so if we took modern technology and AI and what we've learned, I'm not surprised we can do more given the same, let's say, resources than we could in the past. But I think as a general rule, leaning less rather than more is a very, very useful thing, even in this day and age. Particularly because I think the fact that some of these companies are pulling it off, doesn't mean that they've chosen the right path. We don't know how well they would have done had they done three, rather than four things and dropping the smallest, least important one. Maybe biggest, most important one would have been 35, you know, 35% better and, and bigger, and maybe it's a net positive. You know, we're big on we have a value actually, or a quality that we call relentless simplification. We measure ourselves against and we demand [00:54:14] S1: How do you measure yourself? That's fascinating.
00:54:14 · Brian Halligan, Luca Ferrari
[00:54:14] S1: How do you measure yourself? That's fascinating. [00:54:16] S0: Yeah, measure meant like we assess ourselves against it's not, frankly, it's not very, very quantifiable. But we want people to every time so the rule goes like this, every time someone recommends that we should add complexity, whether it's a step in a process, a feature, a team, a head count to a team, you you name it, any element of the system, the burden of proof is on those making that recommendation. Those who believe it's a bad idea don't need to bother bringing any proof, they're fine. And so if we choose to go forward, there needs to be very clear proof that it makes sense, or it has to be revertable, and the people who drive the initiative need to then determine whether it was a clear success and otherwise revert it pretty quickly. And the other part of the rule is that we need to stay alert and question complexity that's been there for a while because we become blind to it as human beings. And anyone who does that should always be applauded, even if it's a nuisance that oh my goodness, again, we're questioning this process or the or this or this policy. But yes, if you have better technology, AI is amazing. And, you know, as someone who failed with AI startup in 2010, I mean, I didn't fail 2010, we started in 2010, failed in 2013. Clearly, I believe in the power of technology. I'm not surprised we can do a lot more today than we could twenty years ago.
00:55:41 · Brian Halligan, Luca Ferrari
[00:55:41] S1: You decided to base a company in Milan. We were based in Boston. I felt like there were some big pluses and big minuses to being in Boston. A lot of people think just you can't create a great company out of Silicon Valley. That's obviously not me. Why didn't you do Milan? What are the pluses and minuses of building outside the Valley? Do you do you predominantly feel like you're like not a cool kid because you're in Milan? [00:56:06] S0: You know, I actually couldn't care less about coolness. Someone who buys a company like AOL cannot possibly care about coolness. If anything, or maybe I do care, but I think that the uncool is cool. You choose, but it's one or the other. I'm not certain. [00:56:26] S1: What are the pluses and what are the minuses? Like my thesis is San Francisco is the best place in the world to start a company, but holy crap is it hard to scale there. It's so expensive that there's not a lot of loyalty. It's just darn hard to scale. What's your thesis on it?