Long Strange Trip: CEO to CEO with Brian Halligan
00:05:30 · Brian Halligan, Anton Osika, Mati Staniszewski
[00:05:30] S2: Yes. [00:05:30] S0: And I was like, wait, they're all working on these impossible problems without any elasticity. So I'm not going to be here. I'm going to go out applying great innovation to the real world. And then I was kind of inspired to start a company when I was in university, which I'm very happy about. But I ended up doing some finance actually, unfortunately. [00:05:56] S1: Okay, it's simple. [00:05:57] S0: Which was a bit too boring for me. Okay. But fortunately I started this community Stockholm AI, and this was around when deep learning was like taking off in twenty fifteen, sixteen. And I did the foundation models of training recurrent new, like large, small language models before it was cool and met great people there. And one was the founder at Sana, so Joel, who recently sold Sana to Workday for a billion dollars. [00:06:24] S2: Yes, congratulations. [00:06:25] S0: Yes, great job by the team there. My contribution was bringing in some of those smart people that went on to grow it to what it became. And I was there for three years and it was like, oh, AI, like let's build it. We were, you all were super young, but learned super fast and it became successful. Then I joined as a co founder at a company that just got into YC, and that was in recommendation systems, specifically for e commerce. That could have been absolutely wildly successful, the company. It had a lot of things going for it. But after [00:07:01] S2: a
00:07:01 · Brian Halligan, Anton Osika
[00:07:01] S2: a [00:07:01] S0: bit of momentum loss and my co founder and me being... I wanted the PO to do something more successful than I can say than e commerce. But I decided to do the most possible, ambitious thing. And all my life I've been approached by people who wanted to find a great engineer to help them realize their dreams or their ideas. That the world is full of them, like 0.5% of the world can even code, and much fewer can build a great product, like Mati and his co founder, right? So I decided, let's build something for the 99%, and not this productivity boost for developers. And that's going to be a completely new type of interface where you dream your idea of some technical AI product into existence. Yeah. And that's what we set out to build. [00:07:55] S2: Okay. So your first company, you were the founding engineer. Your next company depict, you were co founder, CTO. Now you're a CEO. Is it everything you ever hoped? [00:08:08] S0: That's a good question. I think it's quite different. What I love about it is that I get to know myself and how to surround myself with the right complementary skill sets and be challenged in all the possible ways much more than being a co founder and CTO. And like, I run the company on founder mode, I would mostly empathize with. But at this stage, I mean, there's a big shift in focusing on empowering and blocking the leaders in the company. And I mean, I like that. And it's more analytical. [00:08:50] S2: Is being a CEO what you thought like? What surprised you about it?
00:08:50 · Brian Halligan, Anton Osika
[00:08:50] S2: Is being a CEO what you thought like? What surprised you about it? [00:08:54] S0: You have to do so many things. Or I mean, unless you're very disciplined about what delegate and how you delegate it, it's like there's so many, many different things thrown at you, especially as you start hyperscaling. [00:09:09] S2: Yes. How about for you? You're CEO, your first time CEO. What's harder than you thought? What's easier than you thought? What's different than you thought?
00:09:09 · Brian Halligan, Mati Staniszewski
[00:09:09] S2: Yes. How about for you? You're CEO, your first time CEO. What's harder than you thought? What's easier than you thought? What's different than you thought? [00:09:20] S1: Yeah, I think the first one is definitely you want to hire people better than yourself in all those areas that you know for the first time. In our case, things like legal or finance or building the go to market motion in sales. All of these things which I've seen results of that work but never have actually done the work. So it was a very quick learning of how do you do that so you actually understand it. You need to understand at least a little bit to then be able and assess the person that you want to bring in. So that was kind of the two things that they now repetitively try to do when we have a new area. I'm trying to first put myself in those shoes, understand the basics and then hire a person so I know that they are doing that work. And the delegation too was something that I think I hold on for too long, to do myself rather than delegate. And then actually how to delegate was an interesting piece in itself where I think you do want to give a lot of the work to other leaders that you hire, to other people that you grow, but you still want to understand the detail that's happening. And then how do you let them own it, be the leaders they want to be, but still remain in the details in the funder mode to be able to jump in when needed? That balance of how do you interact for that is a tricky thing is still, I think, a continuous learning for me.
00:10:38 · Brian Halligan, Mati Staniszewski
[00:10:38] S2: And like, I finally have this kind of three types of CEOs, these people who are really in all the details in everyone's shorts all the time. Their CEOs are pretty high level and like I have an expression, keep your feet in the ground, your head in the clouds, or you're in the details and you're up high. Some people who stay very high. And then there's what I call spelunkers, people who kind of go down deep in one thing for a while, they come back out and go down into another thing. Have you got one of those models? What are you? It sounds like you're the first. [00:11:12] S1: I do like the details. I think similar like the, I think to how Anton mentioned that you operate is you do on the funding model. You want to understand the product. You want to actually work with the product all the time so you know how to actually use the product better than most. I'm trying to stay extremely detailed in what it is that we are shipping, how we're shipping it, how it works behind the scenes. So that's probably the key thing. I like your analogy of head in the clouds, I the feet on the think the thing that I'm trying and I think where the magic happens if you do it well is being able to zoom out and zoom in extremely quickly before those contexts. So you're able to understand the problem, zoom into the detail, you understand the detail. And then the next second, you need to go to another problem which requires the same activity. [00:12:05] S2: So a lot of context switching being a CEO.
00:12:05 · Brian Halligan, Mati Staniszewski, Anton Osika
[00:12:05] S2: So a lot of context switching being a CEO. [00:12:07] S1: Exactly. And you kind of need to be immediate in that. My co founder, who is the smartest person I know and is kind of leading the research work, in his case, he needs to go extremely deep for a very long time. So we frequently speak about this very different way of approaching the work where one is all about context switching, the other one is all about going as deep as possible. [00:12:31] S2: And how are you feeling about delegation? Is it natural to just delegate all this stuff? Or is it like, I want to be in the details? I had very hard time delegating. [00:12:42] S0: I think it's often the, ah, when I'm very impatient And like, there is some friction when I when there's many things that are feel very urgent and I know one thing, but maybe not all of the other ones. [00:12:59] S2: Are you driving people crazy? [00:13:01] S0: No, mostly no. Mostly they like me, feel where I'm coming from and actually this is coming from a good place. [00:13:08] S2: Okay, let's talk about team. You just hired a friend of mine to run sales. Yep. You're building out your team. How are you thinking about building out your team? Your senior team in particular. And then are you looking for people with high slope or high experience?