Lenny's Podcast: Product | Career | Growth
00:43:55 · Brian Halligan
[00:43:55] S0: I love this one, it's very true. Let's say, Lenny, you bought a new beautiful plant for your office, and then you went away for a month to Turks and Caicos because your AI agent's doing your podcast, and you asked two of your friends, "Hey, would you mind watering my plant?" And there's one of two outcomes what happens to the plant. The plant would either be over-watered and die, or not watered at all and die. And every CEO in the adults' table has gone through this, and they are religious about the DRI. Everyone talks about DRI in the kids' table, but once it gets to the adults' table, people get deep religion on it. And I think it makes sense. When you're small, and you're in startup mode, everyone's in the room, everyone knows exactly what's going on. So, let's say you're running a pilot project with a big account. You're running that pilot project, everyone's on the same page, the sales person, the service person, developer, everyone's on the same page, and you go out and do it and you execute well. When you get it scale, you've get a sales organization, you've get your [inaudible 00:44:56] deployed engineer organization, you've got your product management organization, you've got some developers working on it. Everyone's kind of separate, no one knows really what's going on in the other departments. And so, let's say you want to really have a good pilot process, you want to rethink it because you're scaling. Everything important happens cross-functionally inside a company at scale, and you need someone powerful to own it. So, let's say it's a sales person, they need the power to tell people in other divisions what to do, even if they don't own it. So, almost every CEO I deal with is like a zealot on the DRI idea, and it doesn't bite you until you get to some sort of scale.
00:45:34 · Lenny Rachitsky, Brian Halligan
[00:45:34] S1: To be super clear about that advice here, it's one person is responsible for a goal, a metric, some outcome you want, versus it may feel like, okay, we have two people on this, it'll be awesome, they'll work together. [00:45:45] S0: Yes. [00:45:45] S1: Your advice here is that doesn't work? [00:45:47] S0: Communities never work. Yes. [00:45:48] S1: Yeah. [00:45:49] S0: Yes. And DRI is directly responsible individual. [00:45:53] S1: The way I always thought about this is just having someone's ass on the line for something makes them so motivated to get it done, versus spreading the responsibility and the upside and the downside, it just doesn't work. [00:46:06] S0: I totally agree with you. [00:46:08] S1: Awesome. Okay, another Halliganism, I don't know if you put it this way, the way I think about it is this idea of, "There's no such thing as a silver bullet, it just takes a lot of lead bullets to get something done." I think the way you wrote about it is it's always one step forward, two steps back. Talk about your advice there.
00:46:08 · Lenny Rachitsky, Brian Halligan
[00:46:08] S1: Awesome. Okay, another Halliganism, I don't know if you put it this way, the way I think about it is this idea of, "There's no such thing as a silver bullet, it just takes a lot of lead bullets to get something done." I think the way you wrote about it is it's always one step forward, two steps back. Talk about your advice there. [00:46:24] S0: Yeah, I always thought, incorrectly, that we would have one hire or one investor or one event or one product release that would... I was wrong about this, but it'd be a silver bullet. And the reality inside the HubSpot machine, the way it felt to me, it looks from the outside, over a long time up into the right, and smooth, but inside it was two steps forward, one step back, two steps forward, one step back, two steps forward, one step back. And a lot of times it was a crisis that caused that step back. So, we just didn't have that. The thing about being a founder/CEO is no one, especially when you're in your 20s, there's no one there to rescue you. Your parents aren't going to rescue you, your VC is not going to rescue you, your teacher, your thesis advisor, you're on your own and you got to figure it out. And that hits you when you hit your first crisis, it's on you. You can get some help, but it's on you. [00:47:23] S1: Sometimes they have you in their corner, if they're lucky at Sequoia. Plug, plug. [00:47:27] S0: Yep. I can't solve it oftentimes, I can be the shoulder they cry on, and I can give them advice, but it's still on them.
00:47:27 · Brian Halligan, Lenny Rachitsky
[00:47:27] S0: Yep. I can't solve it oftentimes, I can be the shoulder they cry on, and I can give them advice, but it's still on them. [00:47:33] S1: Do you feel like too many people start companies just like... When someone comes to you like, hey Brian, should I start a company? I have this idea. Do you often just like, no. You have no idea what you're getting into, this is going to be much more painful?
00:47:44 · Brian Halligan
[00:47:44] S0: Yes. Yes. I heard Jensen Huang say that. "I wouldn't have start started Nvidia if I had it to do over." If someone asked me that question, I would start HubSpot over. It was very hard, there were a lot of sacrifices, it wasn't glamorous at all. But in the end of the day, I'm incredibly proud of it. And on my deathbed, I can look back and really enjoy it. And the Dalai Lama's got a good expression like, "Live a good life so you can live it again on your deathbed." And I'm really glad I did it. But I do talk a lot of founders out of it. The obsession is real, you have to be deeply obsessed. And all these founders and CEOs I talk to, people talk about 9-9-6, it's way more than that. The founders are seven days a week, they're always on, I [inaudible 00:48:40] on Sunday nights, it's full contact. And I think what's going on there, particularly now, is people just see this massive platform change, massive opportunity, they don't want to waste the opportunity. So, I think that mindset's right. But people today are much, much more hardcore than they were in my year. I worked hard, and I was probably, I was 60 to 70 week hours a week the entire time, never really turned it off. But that's kind of how I thought about it. It's different now. People are much more focused, and I think Elon's inspired people.
00:49:09 · Lenny Rachitsky, Brian Halligan
[00:49:09] S1: I had a start back in the day, nowhere near as successful as HubSpot, but the way I thought about it is, let me just give it everything I have and see what I can do. This is the shot, this is my chance, let me just give it all. Forget balance, just go for it. Seven days a week for a while. And then you scale back. And it's just such an empowering thing to do for a while, just like, let me just try. This won't be forever. [00:49:33] S0: Yep. [00:49:35] S1: And I know you've written about this, just like balance for CEO is not, you should not have work-life balance if you want to be incredibly successful. I don't know if that's always true, but just... I don't know, how do you talk about that to founders? [00:49:48] S0: I don't know any of the founders I work with that have work-life balance. By the way, this is not something I recommend. I didn't have it, I don't think my co-founder, Dharmesh had it. The only CEO I know, and he's unusual in this way, is Kareem from Clay. He's like, "Nope, you need balance, take the weekends..." He's got a different mindset. I'm going to have him on my pod to talk about his mindset. But he's sort of the outlier, everyone else is really, really obsessed, and they really don't have much of a life. [00:50:21] S1: It did take them a long time to find product market fit [inaudible 00:50:25]- [00:50:24] S0: [inaudible 00:50:25] definitely pre-AI. It did them a long... [00:50:28] S1: I wonder if there's a correlation, but it did work out. [00:50:31] S0: Worked out great.