Lenny's Podcast: Product | Career | Growth
00:59:12 · Lenny Rachitsky, Brian Halligan
[00:59:12] S1: Dharmesh was on the podcast, your illustrious co-founder, and he developed a whole system to avoid this sort of thing. Flash tags, where it's like, this is just an FYI. [00:59:22] S0: We had a whole system. Because we would say something on an email to the management team, or Slack, and everyone would be like, okay, this is what they want, let's do it. And sometimes it is like, you need to do this, and sometimes it is like, we should talk about doing this, and sometimes it is, this is just kind of an FYI, we're thinking about it. And because it got big, we came up with that rubric of, we needed to tag each email with, do you want me to get this done this week, or is this something we should talk about, or is this something that's just FYI, I'm thinking about? [00:59:51] S1: I love that... One of them is plea. Pleading you to do it. I'm not telling you to do this, I'm just pleading that you do what I ask. Oh man. Okay. This all connects. And by the way, you guys were co-founders for 20 years, you shared something before we started recording. So, Dharmesh famously did not ever want direct reports, he's just like, Brian, I want to start this with you, but I don't want to ever manage anyone. And you were talking about how you had to take on engineering, which didn't make any sense.
00:59:51 · Lenny Rachitsky, Brian Halligan
[00:59:51] S1: I love that... One of them is plea. Pleading you to do it. I'm not telling you to do this, I'm just pleading that you do what I ask. Oh man. Okay. This all connects. And by the way, you guys were co-founders for 20 years, you shared something before we started recording. So, Dharmesh famously did not ever want direct reports, he's just like, Brian, I want to start this with you, but I don't want to ever manage anyone. And you were talking about how you had to take on engineering, which didn't make any sense. [01:00:19] S0: No, I'm an engineer and I can code, but it's not good. So, when we started the company he's like, "I was a CEO before, I was terrible at it, I don't want to do it again, you're going to be the CEO." I'm like, "Great." And he's like, "And by the way, I'm not going to have any direct reports." I'm like, "Well, it's just the two of us so don't have worry about it." He's like, "No, ever, never." I'm like, "Yeah, yeah, yeah." And then we get 10, 12 people, we're starting to hire engineers, and onboard them, and making up big decisions, and I would go to him and be like, "Well, can you manage him?" He is like, "Don't you remember I told you I don't want to have any direct reports?" It's like, "Surely you were kidding when you said that?" He said, "Nope." And so, Dharmesh Shah has never had a single direct report at HubSpot. [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.
01:01:02 · 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?