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Lenny Rachitsky: belief

15 Feb 2026 Lenny's Podcast Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)

“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.”

— Lenny Rachitsky

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Everything needed to verify it.

Speaker
Lenny Rachitsky
Attribution
Verified speaker
Claim type
belief
Recorded
15 Feb 2026
Publisher
Lenny's Podcast

Transcript context

…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? 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]- [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.…

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