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Published · transcript-backed

Brian Halligan: 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)

“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.”

— Brian Halligan

Source trail

Everything needed to verify it.

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

Transcript context

…And so, is there any tips here for doing this well, is it just give people a chance? 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]. 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?…

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