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How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

8 May 2025 15 published claims 2 attributable people

Speakers in the public record

Claim mix

evaluation 5recommendation 3belief 3preference 2commitment 1observation 1

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The useful parts, with receipts.

15 published records

01 / recommendation

Recommends Soldiers and Kings.

“I mean, I was reminded recently, I'm reading a book called Soldiers and Kings, which I highly recommend, which is about human smuggling from Central America into the United States, and it's an extraordinary book.”
Speaker
Jerry Colonna
Publisher
Lenny's Podcast

02 / belief

What I think what happens is let's hope this is happening for your audience right now, good quality intimate conversation between people who are authentic and real, creates space for someone to be authentic and real, even if it's just with themselves.

“What I think what happens is let's hope this is happening for your audience right now, good quality intimate conversation between people who are authentic and real, creates space for someone to be authentic and real, even if it's just with themselves.”
Speaker
Jerry Colonna
Publisher
Lenny's Podcast

03 / belief

Interesting. So there's this fear I think people have with Buddhist teachings that you will not be as ambitious and you will not achieve as much if you're not attaching.

“Interesting. So there's this fear I think people have with Buddhist teachings that you will not be as ambitious and you will not achieve as much if you're not attaching.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

04 / belief

The way I think about these sorts of conversations and episodes, I call them Trojan Horse episodes where people come for the other stuff, tactical, practical stuff, and then they get stuff they really need to hear.

“The way I think about these sorts of conversations and episodes, I call them Trojan Horse episodes where people come for the other stuff, tactical, practical stuff, and then they get stuff they really need to hear.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

05 / evaluation

What if you could enjoy the puzzle of trying to create something new, trying to create magic, something out of nothing, but it doesn't matter to your sense of self-esteem if you succeed or fail.

“What if you could enjoy the puzzle of trying to create something new, trying to create magic, something out of nothing, but it doesn't matter to your sense of self-esteem if you succeed or fail.”
Speaker
Jerry Colonna
Publisher
Lenny's Podcast

06 / evaluation

That super connects with exactly again, the way I started this whole thing is I started writing just to crystallize my own thinking, and it ends up being useful to other people.

“That super connects with exactly again, the way I started this whole thing is I started writing just to crystallize my own thinking, and it ends up being useful to other people.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

07 / evaluation

The reason they don't ask these questions is because they worry that this is going to be like, okay, I got to quit my job, move to the woods, give up all these luxuries they have.

“The reason they don't ask these questions is because they worry that this is going to be like, okay, I got to quit my job, move to the woods, give up all these luxuries they have.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

08 / recommendation

A big takeaway for me here, and it just keeps coming up and again and again, is if you're struggling as a leader, if your company's not working as well as you wanted to, if you're having a hard time with your team, going back to that equation, it's not about building more skills like public speaking skills or email skills, or I don't know, financial skills.

“A big takeaway for me here, and it just keeps coming up and again and again, is if you're struggling as a leader, if your company's not working as well as you wanted to, if you're having a hard time with your team, going back to that equation, it's not about building more skills like public speaking skills or email skills, or I don't know, financial skills.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

09 / commitment

I would argue that the more power you have, the more moral responsibility you have to actually pause and figure out what it is that you're doing to be complicit in creating the conditions you say you don't want.

“I would argue that the more power you have, the more moral responsibility you have to actually pause and figure out what it is that you're doing to be complicit in creating the conditions you say you don't want.”
Speaker
Jerry Colonna
Publisher
Lenny's Podcast

10 / evaluation

" And then, we start to deviate from that because life happens and then the anxiety starts. So the question is, how do you hold a growth mindset loosely knowing that you ought to stay present to the world as it is, respond to the changing dynamics, figure out what's next because that's the growth.

“" And then, we start to deviate from that because life happens and then the anxiety starts. So the question is, how do you hold a growth mindset loosely knowing that you ought to stay present to the world as it is, respond to the changing dynamics, figure out what's next because that's the growth.”
Speaker
Jerry Colonna
Publisher
Lenny's Podcast

11 / preference

I love that you can ask these hard questions of Claude/ChatGPT, these questions that make you really scared could ask it what are the answers, and even not have to do the hard work and maybe get a better answer.

“I love that you can ask these hard questions of Claude/ChatGPT, these questions that make you really scared could ask it what are the answers, and even not have to do the hard work and maybe get a better answer.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

14 / observation

seen this a thousand times Lenny, entrepreneurs sabotaging their successful businesses because the belief system from their childhood goes something like, I don't deserve success so let me blow it up.

“seen this a thousand times Lenny, entrepreneurs sabotaging their successful businesses because the belief system from their childhood goes something like, I don't deserve success so let me blow it up.”
Speaker
Jerry Colonna
Publisher
Lenny's Podcast
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