Lenny's Podcast: Product | Career | Growth
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.
00:21:00 · Brian Halligan, Lenny Rachitsky
[00:21:00] S0: Yes. Yes. [00:21:01] S1: Okay, so when you're helping Sequoia decide should we invest in this company, what you look for is, LOCK... I like the S, I'm going to include it there. So, are they lovable? Are they inspiring? O, are they obsessed with this problem they're going after? Do they have a chip on their shoulder? Are they extremely knowledgeable about the problem they're going after? And it sounds like not just the problem but just the studying company's business strategy, things like that. And then, S was a student. I guess that's what S is, student is studying, being a founder, being a CEO. Okay. So, I guess going back just to the question, do you think, just to put it very simply, do you think CEOs are born, or do you think they're made? Can anyone turn into an amazing CEO?
00:21:44 · Brian Halligan, Lenny Rachitsky
[00:21:44] S0: I don't think anyone can do it, I don't think it's just anyone. I will say, I've noticed... So, another little rubric I have, and I don't see a lot of these, but Bret Taylor's one, there's a few out there that are in Sequoia's portfolio. I call them back to the baseball thing, a five tool player. In baseball when you rank a player it's, can they hit? Can they hit with power? Can they run? Can they catch a ball? Can they throw the ball? And they rate them one to 10 at each. And it's very rare that you have a five tool player, extremely rare. And the thing that's kind of new now, are there are five tools CEOs, like Bret Taylor's one. You can code, you have taste, you have vision, you can sell the product, you can convince employees. This kind super CEO. And there's a bunch of them now. And I don't know, I didn't see a lot of those. That certainly wasn't Steve Jobs, he wasn't programming. It wasn't Jeff Bezos. I think there's kind of a new breed that's quite impressive. [00:22:49] S1: These folks you mentioned were this good before AI became a thing, I imagine AI helps more CEOs fill the gaps that they have.
00:22:49 · Lenny Rachitsky, Brian Halligan
[00:22:49] S1: These folks you mentioned were this good before AI became a thing, I imagine AI helps more CEOs fill the gaps that they have. [00:22:58] S0: I think AI is, it's hard to fill the gap of this guy's a developer, he's genius level, obsessive, but can he sell? Can he convince an investor to give him a lot of money and a high valuation? Can he convince brilliant employees to leave OpenAI and join him? Can he convince some big skeptical Fortune 500 enterprise to buy his product? Being able to do that, and have taste, and be able to code really well at next levels, I think is rare. I actually think it might be the other way though, where mere mortals like me, who can kind of code, all of a sudden we're going to be able to build stuff. I think it kind of goes the other way. [00:23:42] S1: I love this list you shared of things that you find CEOs most have to learn. BS detection, inspiring people, giving hard feedback. Maybe the one thing that most often people that become CEOs/founders have to work on, is there a most common thread of, here's the thing you probably need to work on most?
00:23:42 · Lenny Rachitsky, Brian Halligan
[00:23:42] S1: I love this list you shared of things that you find CEOs most have to learn. BS detection, inspiring people, giving hard feedback. Maybe the one thing that most often people that become CEOs/founders have to work on, is there a most common thread of, here's the thing you probably need to work on most? [00:24:00] S0: It's that feedback thing. All of the CEOs are building their teams, and so many are like, I have a co-founder that runs product and engineering, but I need that co-founder to step aside and be the CTO, and the thinker, and the labs person, and I need to hire somebody who can actually run the engineering machine. So many of the CEOs are going through that right now. That's a tricky transition. So many of the CEOs are layering folks, like you hired that early head of sales, he hired 10 people, but just can't quite figure out the sales profile, can't quite unpack the sales process, can't quite forecast accurately. We need to layer the person. Those types of conversations are very tricky and quite unnatural for homo sapiens to have if you're 25 and you've never done anything like that before. So, I see the best ones getting really good at that and studying it, and it's super uncomfortable, but they have to suck it up and get good at it. [00:25:05] S1: What do you find most helps them build these skills, get better at this? Is there some tidbits of advice you give them? Is it something that they study to improve?