Lenny's Podcast: Product | Career | Growth
01:01:02 · Lenny Rachitsky, Brian Halligan
[01:01:02] S1: Incredible. I don't, it's just like a dream, a way to operate, I love that you made it possible for him, and it created all this opportunity for him to tinker and innovate. [01:01:14] S0: Yes, yes, it freed him up to really think and be creative. [01:01:15] S1: Yeah. I'm excited to get him back on the podcast someday, we're going to link to that episode. Maybe a last question, I'm curious if there's anything else you think we missed? As a company grows and scales, the job of a CEO changes. You've written a bit about this, of just how different the job is when you're a starter versus a scale up. What are some of the things that most change where your time goes as a CEO, as the company grows? [01:01:38] S0: Well, you clicked on this earlier, but that inspiration thing. I have a little rubric where it's like, in the startup phase it's 90% perspiration, 10% inspiration. When you get the scale up phase, it's 90% inspiration, 10% perspiration. And over time you're doing every job in a startup, and you still need to be very attached to it, and you still need to talk to customers, you can't give it up. But man, you have to let go of so much stuff over time in order for the organization to scale, and I have trust issues. I only trusted a small number of people at HubSpot to be a DRI, and to really drive something important. It drove people crazy, that I didn't have a larger trust surface. Every one of the CEOs I work with has the same problem. And that's a scaling limit, that was a limit for me. I wasn't trusting enough.
01:01:38 · Brian Halligan, Lenny Rachitsky
[01:01:38] S0: Well, you clicked on this earlier, but that inspiration thing. I have a little rubric where it's like, in the startup phase it's 90% perspiration, 10% inspiration. When you get the scale up phase, it's 90% inspiration, 10% perspiration. And over time you're doing every job in a startup, and you still need to be very attached to it, and you still need to talk to customers, you can't give it up. But man, you have to let go of so much stuff over time in order for the organization to scale, and I have trust issues. I only trusted a small number of people at HubSpot to be a DRI, and to really drive something important. It drove people crazy, that I didn't have a larger trust surface. Every one of the CEOs I work with has the same problem. And that's a scaling limit, that was a limit for me. I wasn't trusting enough. [01:02:33] S1: Brian, I feel like I could chat with you for hours, there's a whole list of Halliganisms I'm going to link to that we didn't even touch on. But before we get to our very exciting lightning round, is there anything else that you think we should chat about? Anything you want to leave [inaudible 01:02:48] with?
01:02:33 · Lenny Rachitsky, Brian Halligan
[01:02:33] S1: Brian, I feel like I could chat with you for hours, there's a whole list of Halliganisms I'm going to link to that we didn't even touch on. But before we get to our very exciting lightning round, is there anything else that you think we should chat about? Anything you want to leave [inaudible 01:02:48] with? [01:02:49] S0: Well, I would say if you are a CEO and you're interested in scaling, I think the Halliganism posts is all the mistakes I made in my 15 years of being CEO, I tried to summarize them there, to help you avoid them. And I have a pod, you should first listen to Lenny's pod because it's amazing, but I have a pod just for CEOs, called Long Strange Trip. Where I interview, I interview CEOs about this. So, Lenny's interviewing me about being a CEO, I get to interview other people about being... I'm kind of a CEO geek these days. [01:03:17] S1: And the name of the podcast is a Grateful Dead reference, which- [01:03:20] S0: Yes. [01:03:20] S1: We haven't touched on, but you're a huge Deadhead, as they say. [01:03:23] S0: [inaudible 01:03:25]. [01:03:25] S1: That could be a whole other podcast conversation. [01:03:27] S0: I think there sure, actually. Because I wrote a book called Marketing Lessons from the Grateful Dead, and there's so much... The Grateful Dead were like the ultimate Silicon Valley startup. They started in 1964... Do you know where they started, Lenny? [01:03:43] S1: No.
01:03:43 · Lenny Rachitsky, Brian Halligan
[01:03:43] S1: No. [01:03:44] S0: Palo Alto. Their early concerts were at Stanford, were all over Silicon Valley. They're a Silicon Valley company. They were very first principles in their thinking, they created a new category, a new way to distribute their music, they disintermediated the ticketing companies, very innovative. Steve Jobs and Jerry Garcia are very similar in my mind, real craftspeople. So, I think of them as a great Silicon Valley success story. [01:04:14] S1: You said you had a whole book about this, what's the book called just in case people want to dig in? [01:04:18] S0: Marketing Lessons From the Grateful Dead. [01:04:20] S1: Amazing. And I read that you bought Jerry Garcia's guitar for a large sum at some point. [01:04:26] S0: Yes, I did. And I consider myself the steward of his guitar. It gets played, like Dead and Co played it, and there's a million Grateful Dead cover bands, I let them play it, but I'm taking care of it for the Deadheads. [01:04:41] S1: What's one nugget of wisdom or lesson that people can take away from the Grateful Dead for startups?
01:04:41 · Lenny Rachitsky, Brian Halligan
[01:04:41] S1: What's one nugget of wisdom or lesson that people can take away from the Grateful Dead for startups? [01:04:48] S0: Okay, people talk about spiky teams, the Grateful Dead team was interesting. Garcia himself was a bluegrass guy, he was a banjo player. And then Bob Weir, recently passed, was a country crooner, like country music. Then their bass player was a avant-garde jazz trombonist, Phil Lesh. And their keyboard player was a guy named Ron McKernan, Pig Pen, and he was a harmonica guy. And the drummer was a marching band drummer. And so, spikiest of spiky teams came together and made a new genre, they created a new category of music. It wasn't rock and roll, it wasn't sort of Rolling Stones, it wasn't Buddy Holly, it was this new thing. And then they called it a jam band, because they played rock and roll in a bluesy, open, organic kind of jazzy way. And so, spiky teams in creating categories, underrated. [01:05:47] S1: Incredible. Are you one of these people that have been to 100 Grateful Dead concerts [inaudible 01:05:51]- [01:05:51] S0: Yes. [inaudible 01:05:53]. [01:05:53] S1: Makes sense. Okay, this could be a whole podcast, but we're going to move along. Okay. With that, we've reached our very exciting lightning round. Brian, are you ready? [01:06:06] S0: Yeah. [01:06:06] S1: Let's do this. [01:06:07] S0: Fire it up, I've watched you do the lightning round so many times. [01:06:10] S1: I'm flattered. Unsurprising questions. What are two or three books that you find yourself recommending most to other people?
01:06:10 · Lenny Rachitsky, Brian Halligan
[01:06:10] S1: I'm flattered. Unsurprising questions. What are two or three books that you find yourself recommending most to other people? [01:06:17] S0: I haven't read a book in a long time. I listen to podcasts, I'm on X, I talk to a lot of other CEOs. I can't remember the last time I actually sat down and read a book. [01:06:26] S1: Much respect. I had Marc Andreessen on recently, and I don't know if you've heard his whole thing on what he consumes, he talks about he has a very barbell strategy to media. It's either Twitter or books that are 10 years or older and nothing in between. [01:06:40] S0: I've heard him say that. Yeah, I kind of stopped reading. I looked at that, I was getting ready for this, Lenny, and I was like, I can't remember the last book I read. [01:06:49] S1: I think this is going to make a lot of people feel better that don't read books, are like, all right, this is okay. Favorite recent movie or TV show you've really enjoyed? [01:06:58] S0: I love the new Ken Burns, very long, very good Revolutionary War documentary. He's a crass person, it's exceptionally well done. And what I like about it is America's really a disruptor startup, so many startup lessons from those... They were gutsy. Talked about two steps forward, one step back. They got into the details of how George Washington ran the Army. We were very close to losing that war most of the time, and two steps forward, 10 step back, two step forward, 10 steps back. [01:07:36] S1: Lots of lead bullets.