Long Strange Trip: CEO to CEO with Brian Halligan
00:33:10 · Chase Lochmiller
[00:33:10] S0: I had a coach, and I I still... We're we're still we're still quite close. We're not working as closely together as we once did. But Shane Metcalf, he he was a phenomenal, phenomenal coach for me. I learned so much from him. I... Public speaking was never something that came naturally to me. It was something I had to work really, really hard at, because I I just wasn't doing it. Like, I'd given lectures and things, like, at, you know, universities. And, but it it wasn't a... It wasn't something that I was routinely doing, especially... Like, the quant space is a very... You know, it's a very technical industry, so you're working with very smart people, but you're you're doing it in a very secretive way. Right? It's like you you're very open with your teammates, and then you don't tell anything to anybody in the world about what you're doing for fear that you might leak some of your alpha. So I was never out in the world presenting stuff. And so it was something that I had to work very, very hard at to just be prepared for what I was going to say, how I was going to say it. And I think if you do it enough, you just get practice. And at some point, you just, like, stop having to prepare as much for things. And then most things at this point, I kind of just, like, wing them. Because, you know, the... Like, there... There's certainly things that, like, just require a tremendous amount of preparation. But, you know, I think I'm often better off the cuff because I... You know, it's just, like, how how I think through things. And I... I'm I'm... I've developed a a good skill set of being able to explain what's in my mind, you know, fairly clearly to to to whoever to I'm talking to.
00:34:47 · Brian Halligan, Chase Lochmiller
[00:34:47] S1: What else did you learn from... First of all, should all the CEOs I work with hire a coach? Yes. In like... Yes. Okay. Interesting. What did you learn... Like, what did Shane teach you, or what did he push you on? [00:34:58] S0: You know, one of our investors, Felicis, they had this really cool thing they do for for companies, and I haven't seen anybody else do this. But they have a budget for, like, personal investment, essentially. It's it's like, you know, it's it's not... It's it's, like, meant for, like, self improvement. It's meant for things like executive coaching and off sites and just ways of up leveling yourself as a leader Because they're like, Look, we're making this big investment in, like, the founder or the CEO, and, you know, we're betting on you being able to get better. That you're a static version of yourself, that you're actually gonna be a, you know, a better version of yourself over the course of time, you know, as the business grows. And, you know, I think... I I just thought that was, like, such a thoughtful approach to the investment, especially, like, in venture where, like, the investments are so much about the people and the ability of the founder to scale. You know, I... Shane... Like, early days, it just felt like Shane was a guy that, like, always had the answer to the problem that I was, like, racking my brain on. And, you know, he was as much of a coach as like almost like a therapist for me. [00:36:13] S1: That's how I feel with my CEO, as much as coach as a therapist.
00:36:16 · Chase Lochmiller
[00:36:16] S0: It was... So, you know, we really did have a very, you know, still do a very, very special relationship that's very trusted. And I I I just felt like, you know, it's something you have to work at, and you build this trust with a person. And even if it doesn't feel like you're making progress on any given session, you're laying the groundwork and you're laying this foundation for when that really big thing does pop up. This person knows you so deeply, and they know where your blind spots are, and they know how you might be responding in a certain situation, and they know how to, like, guide you to course correct, to be able to, you know, rise to whatever occasion it is. And, you know, I think... I don't know. I mean, people say this, and it's... You know, I may sound like I'm repeating the common folklore, but so many of the problems with building companies are people problems, right? Being able to effectively navigate the people side of this is like it's... That's like most of the challenges. Like, you know, you get these smart, ambitious, opinionated people getting everybody to work and row in the same direction and agree on things, or if they don't agree, to commit to whatever pathway you're taking. I mean, that is always the hardest thing. And as a CEO, I think sometimes the biggest challenges are, when do I keep believing in someone and when do I decide, hey, we need to move on and we need a different person in this role? Or how do we get two brilliant people to work together on something that are fundamentally disagreeing? I don't know. I've just found the people to be the hardest thing and also the greatest superpower if you can get it right.
00:38:02 · Brian Halligan, Chase Lochmiller
[00:38:02] S1: People always said to me, you should hire slow and fire fast. I did the opposite, particularly on the fireside. It sounds like you moved some people out. Did you do it too slowly? Did you ever regret it? What were the signals that kind of push you over the edge? [00:38:21] S0: I think almost always there's a bias towards... You just end up firing people too slowly. It's it's just like there's an inherent bias. So even if you're very responsive, like, you know, I I I do think that for most CEOs, you know, when you fire someone, you've clearly been thinking about it for a long time. And it's almost like when you started thinking about it, that was sort of the right time to fire them. But, like, you know, it's hard to... [00:38:49] S1: What signal do you... Are you looking at? Is it other people on the team saying this person's subpar? Is it... What is it?
00:38:56 · Chase Lochmiller
[00:38:56] S0: It's it's not that. It's it's you know, that is definitely like a data point. It's it's like a I think our job as a CEO is, you know, you are reading this mosaic of information, right? You have all these little tidbits, and they're often in from, like, very different parts of the organization and different... You know, coming from someone super technical, coming from someone that's, like, more of a people person, coming... You know, like, all these, like, different things, and and you're sort of amassing all these different pieces of information. And, you know, it's up to you to, like, make a judgment call around, like, what the best decision is for the company. I do think that... I forget who published it. Think it was First Round Capital has this really great blog called The Startup Laws of Physics. And the crux of it is something along the lines of you know, people scale linearly, companies scale exponentially. So you sort of have this great companies scale exponentially. So you sort of have this dynamic where even if you challenge your people to continue to grow and continue to invest in themselves, if the company really grows in the way that you're sort of setting out as an as an ambitious leader, oftentimes, like, the person who was the right person for that role at one point in time may not be able to grow and scale to be the person in that role two years later when the company is 10 times bigger. And that... That's that's a hard reality to face as a leader because you end up in the trenches with these people. You end up, like, working late nights, early mornings. You know, you know, you see these people really giving everything they have, you know, to the mission. And, when you when you have those moments where the the company outgrows the person, it's really just hard, right? Because you care a lot about these people on a personal basis, even if you know the best thing for the company is to find someone new for a specific role. Anyway, coming back to why I've fired people in the past, it's almost like every case is a snowflake. Every single one is different. And, you know, it's it's it's ultimately up to you to make the the the judgment call of what's what's the right thing for the business.
00:41:09 · Brian Halligan, Chase Lochmiller
[00:41:09] S1: Okay. I... Two of my recent interviews, I interviewed Ali Ghodsi from Databricks. Love him. [00:41:17] S0: Great guy. [00:41:18] S1: And he he... He's basically had the same management team for ten years with the... He turned over one person. And then David to carry a friend of mine and coming on the pod. On average, he turned over two per year on the exec team for lots of reasons. I find that odd. They're in kind of similar businesses, and it's just so and they're both really good, and they're so different. [00:41:45] S0: Totally. Actually, my current COO and CFO worked alongside Dave at MongoDB for for about a decade. So he wasn't one of the people that was, you know, churned. [00:41:58] S1: By churn, I mean, some of them leave. They No. [00:42:01] S0: I I totally understand. And, but, look, I don't think there's any right answer. And, you know, I I've seen different things work. I think what I've found most effective for me is that, if you have someone that's really struggling, the team recognizes it. And we view it as the team is ultimately there to win. And I mean, I saw this... I grew up playing competitive sports. And if you were on a team, you always loved your teammates. You had a strong and special bond that came from the locker room down the field. And if you had a teammate that was just struggling or a weak link and led to the team's downfall, it was like you knew that the right thing to do was to replace that person with someone [00:42:48] S1: It sounds like you're in the middle of those two. [00:42:51] S0: I'm in the middle of the two, for sure.