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Brian Halligan

Published podcast speaker

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18
Episodes
1
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1
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1

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Delphi

“I love my Delphi clone, I teach a course called Scaling Entrepreneurial Ventures, and I don't do office hours, I have Delphi do my office hours.”

Lenny's Podcast · 15 Feb 2026

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What Brian said.

18 transcript-backed records

01 / evaluation

And almost by definition somebody who goes to work for McKinsey is very conservative in their outlook. And so, I think that almost always fails.

“And almost by definition somebody who goes to work for McKinsey is very conservative in their outlook. And so, I think that almost always fails.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

03 / belief

I think you can, I think the blind references are key, I think doing real interactive, working on a project together is key.

“I think you can, I think the blind references are key, I think doing real interactive, working on a project together is key.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

06 / belief

The founders are seven days a week, they're always on, I [inaudible 00:48:40] on Sunday nights, it's full contact. And I think what's going on there, particularly now, is people just see this massive platform change, massive opportunity, they don't want to waste the opportunity.

“The founders are seven days a week, they're always on, I [inaudible 00:48:40] on Sunday nights, it's full contact. And I think what's going on there, particularly now, is people just see this massive platform change, massive opportunity, they don't want to waste the opportunity.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

07 / belief

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.

“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.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

08 / belief

I think people think they're going to live forever and they're not. As somebody who's 58, yeah, life's very short, and I'm much more intentional about the decisions I make, much more intentional about the people I hang out with today than I was before that.

“I think people think they're going to live forever and they're not. As somebody who's 58, yeah, life's very short, and I'm much more intentional about the decisions I make, much more intentional about the people I hang out with today than I was before that.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

10 / evaluation

I think CEOs and everyone dramatically overrates their ability to interview, and overrates their gut feeling, and underrates a really high quality blind reference.

“I think CEOs and everyone dramatically overrates their ability to interview, and overrates their gut feeling, and underrates a really high quality blind reference.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

11 / evaluation

Baseball's also deeply flawed, it doesn't have a salary cap. And so, you've got the Dodgers, who I take my hat off to, have a $400 million payroll, and then Miami Marlins with a 100 million dollars payroll, and in other leagues that all kind of balances out pretty well, baseball, it's set up incorrectly.

“Baseball's also deeply flawed, it doesn't have a salary cap. And so, you've got the Dodgers, who I take my hat off to, have a $400 million payroll, and then Miami Marlins with a 100 million dollars payroll, and in other leagues that all kind of balances out pretty well, baseball, it's set up incorrectly.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

12 / evaluation

I'll just follow on to, most of the good things that happened in HubSpot came out of a crisis because we would take pretty drastic measures to fix it and make sure we didn't do the same thing again.

“I'll just follow on to, most of the good things that happened in HubSpot came out of a crisis because we would take pretty drastic measures to fix it and make sure we didn't do the same thing again.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

13 / preference

I don't know any of the founders I work with that have work-life balance. By the way, this is not something I recommend.

“I don't know any of the founders I work with that have work-life balance. By the way, this is not something I recommend.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

14 / evaluation

Let's say you found your beachhead market, and that beachhead market is really good, and it's very deep, there's a lot of work to do, I think what's dangerous for companies is they hop to that second act too quickly, and they lose focus on that first act.

“Let's say you found your beachhead market, and that beachhead market is really good, and it's very deep, there's a lot of work to do, I think what's dangerous for companies is they hop to that second act too quickly, and they lose focus on that first act.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

16 / preference

Before he's got a C-level interview, CFO, chief product officer, whatever, he has some sign an NDA, and sends them the last board deck, or the board memo, or some important doc, and he schedules a half hour interview with them, and he just has a chat about the decks. And if they're just very complimentary, and it's so great, and you're doing this amazing thing, it's a major red flag to him because he wants someone that will challenge him and not a yes person.

“Before he's got a C-level interview, CFO, chief product officer, whatever, he has some sign an NDA, and sends them the last board deck, or the board memo, or some important doc, and he schedules a half hour interview with them, and he just has a chat about the decks. And if they're just very complimentary, and it's so great, and you're doing this amazing thing, it's a major red flag to him because he wants someone that will challenge him and not a yes person.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

17 / recommendation

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.

“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.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast

18 / preference

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.

“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.”
Speaker
Brian Halligan
Publisher
Lenny's Podcast
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