Lenny's Podcast: Product | Career | Growth
00:14:12 · Lenny Rachitsky, Brian Halligan
[00:14:12] S1: I remember that. [00:14:13] S0: And they finally broke, and they finally won it in 2004. And the way they won it was they had a team of a bunch homegrown, really high quality, inexpensive talent that they drafted and came through the farm system. And then they got a few free agents, like David Ortiz, that a lot of people have heard of, that they paid a fair amount of money to. Pedro Martinez and Curt Schilling were kind of the canonical older been there, done that, bigger company folks. And they mixed really nicely, the culture really worked. And I think that's the key. I think people underrate their homegrown talent, almost across the board they underrate it. And I think you want that mix. You don't want to hire a whole bunch of been there, done that, and you don't want to hire [inaudible 00:14:57]. [00:14:57] S1: I imagine this is public, but you're now part owner of the Red Sox, is that right? [00:15:00] S0: I am a part owner of the Red Sox, yes. [00:15:02] S1: Okay, I have questions for you along those lines. [00:15:04] S0: Okay. [00:15:06] S1: Okay, that's amazing advice. Kind of what I'm taking away here is people see all these fancy logos, amazing person, VP, this, that at Salesforce, Amazon, Google, whatever, and what you're saying here is don't underestimate the power of someone internal, rising to the occasion. [00:15:22] S0: Yeah. If you look at HubSpot, half the management team are folks who had been there for approximately 150 years, which I like. And same with, you look at Apple, a lot of those people are homegrown.
00:15:22 · Brian Halligan, Lenny Rachitsky
[00:15:22] S0: Yeah. If you look at HubSpot, half the management team are folks who had been there for approximately 150 years, which I like. And same with, you look at Apple, a lot of those people are homegrown. [00:15:32] S1: And so, is there any tips here for doing this well, is it just give people a chance? [00:15:36] S0: I tend to give people a chance. It's like, if you're interviewing someone that's homegrown, and they're VP for that C-level job, versus hiring someone from the outside. I hire someone from the outside, they're very good at interviewing, from a big company, they look fancy, they're shiny, you haven't seen their warts, hard to figure out their warts unless you're very good at line referencing, and so you tend to overrate them and underrate your homegrown. So, if it's pretty close, I think you give your homegrown a shot at it. What's interesting to me, Lenny, is Brian Chesky sort of rethought a lot of this stuff, and he's like everyone's over-rotating to the homegrown to the experienced talent and management teams and delegation, I think he's mostly right about that. People haven't really followed that. People are, they're hiring people from the outside quite a bit. That's kind of the standard part of the playbook that all of them are following now. It's a little different, it's actually quite different than what Brian [inaudible 00:16:32].
00:16:32 · Lenny Rachitsky
[00:16:32] S1: Going back to the conversation around CEOs, a lot of people listening to this podcast, just a lot of people in the world want to be founders, they want to be CEOs. At the same time, you look at Elon, you look at Jensen, you look at Steve Jobs, you look at you, a lot of people are like, I can't. I'm not this person, I'm not going to be as good as them. There's no world where I'm this good. Do you feel like there are specific profiles or just traits that you have to be born with to be a successful CEO, or do you think it's earnable, anybody can be successful if they really work hard?
00:17:02 · Brian Halligan
[00:17:02] S0: Go ahead and meet all these CEOs coming in, and I have a little algorithm in my head, and I look for four things. I call it my LOCK algorithm. L is for lovable, and Steve Jobs you would say is kind of rough and maybe not lovable, but he would inspire followership. You would want to follow him. And so, could I envision a 28-year-old me, graduating from business school, going to work for this person? Would I crawl across broken glass? That's question one. Two is just obsession. Are they deeply obsessed with this problem? I'm a little negative on people who came up with this problem to solve six months ago and started a company, I like people with deep founder market fit, who've been thinking about it for a long time, and have evidence in their lives of going deep down, obsessively down a rabbit hole because that's kind of what it takes to be a founder/CEO. The C is something I wouldn't have thought of, but this is a Sequoia thing, like chip on the shoulder. Pretty much all of them have a boulder on their shoulder, and I have a bit of a chip on my shoulder too. And the K is just for deeply knowledgeable about the domain. And so, I look for that. If I were to stick an S on it, I would say student. I look at Winston Weinberg from Harvey, or James from Profound, or Gabe from Rogo, some of these new very fast growing companies, they're students of the game. They're not just learn it alls, they're deep, deep, deep students of the game. And they're like LLMs, they're constantly, constantly learning, and it's not just learning stuff for me and their peers, but they go way back in time, and have a lot of history on stuff. So, those are some of the, kind of my little criteria I use when I'm evaluating CEOs. What do you look for, by the way, you've interviewed a ton of folks like me, what do you think is in common?
00:19:11 · Lenny Rachitsky
[00:19:11] S1: Of what successful founders? Oh my god. I wish I had the... My succinct answer, I would go to Lennybot.com, and be like, what is the common pattern across these folks? One that you didn't mention that I think is interesting, I did some research on this recently, with Terence Rohan, one is just extremely ambitious. Just trying to do something really wild that most people are like, that's crazy. You're not going to get a subscription service for all music in the world, that's just... What are you doing? [inaudible 00:19:38]-
00:19:40 · Brian Halligan, Lenny Rachitsky
[00:19:40] S0: [inaudible 00:19:40]. Is it learnable? I notice some of, a lot of the CEOs struggling with a couple of things. Like let's say you're Winston, you're late 20s, you've never managed a team, you're probably never even captain of a sports team before, and in order to scale, you have to give people feedback constantly. It's very unnatural. It's like, I'm going to give this VP I hired a bunch of feedback, positive and negative. And if you don't get good at that, you really pay the price later. That's something I think they have to learn. They all have to learn to get a good bullshit detector. They're constantly being spun, everyone's trying to sell to them, the org is always trying to sell to them. So, that's sort of something they have to develop over time. They have to all get good at the inspiration thing over time. Like, you're Winston, you've never had to inspire anyone in your entire life. You went to school, and you're a lawyer for a few years, and you started this thing... Inspiration wasn't your thing. So, there's certain things you have to learn on that startup to scale up path, and the best ones learn it very fast. [00:20:50] S1: This is extremely interesting and useful. So, LOCK, with an S at the end, just to kind of mirror back what you're sharing. And when you were saying you evaluate CEOs, is this for investing as a- [00:21:00] S0: Yes. Yes.