Long Strange Trip: CEO to CEO with Brian Halligan
00:47:51 · Mati Staniszewski, Brian Halligan
[00:47:51] S1: First of all, I think go for it. It's amazing to build a company. Of course, maybe I was in a lucky position where I had savings and I didn't have the dependencies. But if you are in that similar situation, I think it's go for it. The learning experience you get across building a company, even if it doesn't go the way you expect, I think it's so much more valuable than frequently joining other companies and being a smaller coggle in a big machine. And then I think obsess about the problem, try to deeply understand what you are actually solving for, talk with customers. And the simplest advice I think is the most valuable here, which is actually working with the user and iterating very deeply. And then I think it's all about the team and hiring. So the people you bring across and who you build with will be defining for the company. So pick your co founders carefully and well know them ideally for a longer time before you decide to start something. And then assemble the team. You really want the trusted individuals that you want to go for the next decades together. [00:48:55] S2: Anton?
00:48:55 · Brian Halligan, Anton Osika, Mati Staniszewski
[00:48:55] S2: Anton? [00:48:57] S0: I think you want to learn things very, very fast if you're getting started. And you want to learn a lot of things. You want to learn how to hire. I mean, you don't have to be so good at managing, but having high expectations of people and giving them clear feedback. And you want to know, learn how to sell. You want to sell to your customers or sell to them or under market, to your the people you want to hire, if you want to you're always selling. And you should do that all the time and fail, and ask someone who you respect to give it to you hard on like how bad you are. [00:49:32] S2: I see. [00:49:33] S0: Because you just get it started. [00:49:33] S2: Were bad [00:49:34] S0: at first? Yeah, of course. [00:49:37] S1: Like it's nice. [00:49:39] S0: That's just so you just go out there and and I try to find joy probably by having a co founder, as you're talking about, in failings and the learnings. Yes. [00:49:49] S1: Yeah, that's the other thing which I was thinking about your earlier question, what you don't expect as a CEO's role. You don't expect that you don't have anyone to complain to [00:49:59] S2: effectively. So [00:50:00] S1: your co founder is your soulmate that you can speak for. And then there are some sometimes amazing people on the team you can iterate through, but not to the same, not to the same.
00:50:00 · Mati Staniszewski, Brian Halligan, Anton Osika
[00:50:00] S1: your co founder is your soulmate that you can speak for. And then there are some sometimes amazing people on the team you can iterate through, but not to the same, not to the same. [00:50:09] S2: Yes, I totally agree with that. I want to congratulate you guys on all your success. I admire what you guys are doing. I sure hope you guys build trillion dollar companies in Europe. That'd be amazing. Good luck to you. Thanks for doing the pod. [00:50:23] S0: Thank you so much. Appreciate Brian.
00:50:24 · Brian Halligan
[00:50:24] S2: Appreciate you. Thank you. Yeah. Okay. Those two are terrific, and it's nice to see them kind of blossoming before our eyes. What they have in common is they both had, like, seven or eight years of experience with, like, one good company in there. And I know it's fashionable to drop out of Harvard and start a company like Zuck did, but at least for me, I did two startups before HubSpot. One was very successful, went public and got very large. Man, did I learn a lot from that. And man, are there a lot of lessons inside HubSpot about scaling? But you do you, but I don't think it hurts a founder to be in a really good startup to learn before they start a company. They talked a lot about their cofounders. And one of the things about being a CEO is you're you're you're a shit umbrella. Like, all the shit rains on you and you've got an umbrella for your whole organization. It's hard. The other thing about being a CEO is like no one is coming to save you. In my startups, my boss would come and save me. Another team would come and save me. There was a lot of resources around. You're pretty alone, and it's on you as a founder. The one person you can complain to is your co founder. And so my advice to you would be to really get to know your cofounder because it's an incredibly important relationship for you going forward. We've gone into mechanics of of the job, and we talked about delegation. And they're kind of starting to... It's interesting. They're starting to delegate. They were like, oh, we're kind of founder mode. We're not sure how to do this, but they're starting to do it. It's impressive to see what they're doing. My experience, the way that work as HubSpot scaled, I was very founder mode in sales and in product and man, the rest of the organization, I was very manager mode. And I drove both constituencies crazy. The the sales and product folks, I was in their shorts and they always complained I was too much in the details. All the rest of them complained that they didn't respond to their emails. So that was sort of the blend for me. I wasn't all manager mode. I wasn't all founder mode, and that kind of worked for me. And may... Maybe that would work for you running your company. I like the way they were thinking about their teams. I ask all the CEOs on these episodes, you know, what's their span of control? And it's all over the map. I...
00:52:39 · Brian Halligan
By the way, I thought everyone was copying, Justin Huang and having 60 direct reports. That is definitely not true. He is an n of one on that. And, like, Anton Helmley has five direct reports. I had 10. Mati has 15. So it's a little bit all over the map. If I were you, I would think about that. What do you want your span of control to be? And I would have it as wide as you can tolerate. As you scale from a 100 to a thousand employees, all those layers in there really will slow you down. So you wanna keep it as flat as you can. The other thing I liked about that we're thinking about teams is they were definitely starting to bring in some been there, done that people. The whole team wasn't been there, done that. The way HubSpot ended up is we had about half been there, done that, and a half homegrown. And VCs try to jam you full of been there, done that. I like that balance having a little bit of both. The homegrown talent is underrated on your teams most likely. We also talked about just managing the chaos, like they're growing crazy. They have so much opportunity. It's just a hurricane of of input coming into them. And a couple things, couple hacks I liked. Anton is really good on Twitter, by the way. If you don't follow him, he's really good. I like that every Monday morning, he has a fifteen minute meeting with a couple of his staff members and they brainstorm on tweets. So he's not just coming up with that extemporaneously. He's thought about it a little bit and he's very good at it. Most of them, or at least I had a no meaning day where I could actually think and get some room and work on projects. I think that's a good hack. I had it on Fridays for a while. Everyone thought it was a long weekend. They moved it to Wednesdays. And they're gonna have to get good at saying no. Like, I I was working on saying no, so I made myself this hat, my no hat, and I had a no shirt too. And I think startups are much, much more likely to die of overeating and starvation. That's probably true of yours. You might need your own no hat. You know, speaking of chaos, I asked them, are they nine nine six? And they are both nine nine six plus. And I think that's interesting. I've I've asked all the CEOs I've been interviewing. There's been 10 so far. And the early stage startups are all doing nine nine six, and the bigger ones aren't.
00:54:52 · Brian Halligan
And I think that's probably life in the fast lane. As your employees start having families and you're hiring people to families, it's just hard to get people in the office six days of work working nine to nine. But I think keep it going as long as you can. If you're doing nine nine six, I think it's good. I was nine nine six, but I didn't ask my team to be nine nine six. We talked a lot about Europe. There's two amazing companies in Europe. In Europe, so we started in Boston, and Boston's a little bit out like Europe. You're, like, outside the echo chamber of Silicon Valley, and there's some real pluses and minuses to being outside of the valley. The pluses are you end up being a very large fish in a very small pond, which can help, And you have really good access to talent and not a lot of competition for that talent. So real pluses. The minuses we found out at HubSpot and they're gonna find out is inside of Boston, there's just not a lot of scale tech companies. So we had a hard time finding executives who had seen that movie on that next level of scale. Like, we took a couple people from Akamai and that worked out, but it was pretty lean. And so we started hiring execs out in San Francisco. So real pluses and minuses to being in a big city. If I had to do HubSpot over again, by the way, you didn't ask, but, I would have... We were in Boston. I'd have a big office in Boston, big office in San Francisco, then another big office in, I don't know, Nashville or Denver or Toronto would be pretty good where you can hire lots and lots of people for less money and have them be a little bit more loyal than, let's say, in your San Francisco office. I wouldn't let everybody work from home. I'd have three big hubs. Okay. We wound up obviously talking about Europe. They're both in Europe. Really encouraging for Europe. The world could use more Silicon Valleys, and the world could use, you know, a vibrant European entrepreneurial scene. I love to hear from them that the engineering schools are chock full of kids that want to start companies. I think that's going to be good for the world and good for Europe. So I'm excited about that. I hope you enjoyed the episode. I really liked it. These two are great. I will see you on the next episode of Long Strange Trip.