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534 passages, newest first · 56 ms

DHH2025-07-12transcript-lex-474-2025source ↗context

`2:50:55`

I could just delegate to his experience and competence and say like, do you know what? I may have an opinion, I have an opinion all the time on design. But I don't have to win the argument because I trust you. Now occasionally we would have overlaps on business or direction where we'd both…

DHH2025-07-12transcript-lex-474-2025source ↗context

`2:51:56`

all the time. Most of our careers, we haven't even lived in the same city. Like I lived in Chicago for a couple of years while we were getting going after I'd moved to the US in 2005. But then I moved to Malibu and then I lived in Spain and then I lived in…

DHH2025-07-12transcript-lex-474-2025source ↗context

`2:52:56`

The more ideas that can bounce back and forth, the better. And both Jason and I, for whatever reason, came to the conclusion early on in careers. Absolutely not, that's complete baloney. This is why we were huge proponents of remote work. This is why I enjoy working in my home office where I can close…

DHH2025-07-12transcript-lex-474-2025source ↗context

`2:53:57`

until next month. — And there is a temptation for the managers and for the people in the executive layer to do something, which that's something usually means a meeting, right? And so that's why you say... — Their job is telling other people what to do. — Yeah, and the meeting, so this is one of the…

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`2:54:59`

There's some amount of time we can spend together where you can wear it out. Jason and I were diligent about not wearing each other out. And I think that is absolutely key to the longevity of the relationship combined with that level of trust. And then just combining with the level that we really like…

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`2:56:01`

— Yes, oh, goddammit. — Get a couple kids. — [Lex] All right. — Like family really is the great antidote to loneliness. And I mean that as sincerely as I can possibly say it. I certainly had exactly that feeling you described early in my career when I was working remotely and I was just a, like me living in…

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`2:57:01`

And I think it's key for both Jason and I that we've had families for quite a long time and it grounds you two in a way where the sprint of a startup can get traded in for the marathon of an enduring company. And you get settled in a way. We talked briefly about…

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`2:58:01`

we'd be better off and we'd have more stable business relationships as well because folks would get that nurturing human relations somewhere else. Now when I say all of that, I also accept that there are plenty of great businesses that's been built over the years that have not been built remote, that have…

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`2:59:02`

which included building up friendships outside of work, having hobbies, finding a mate and having a family. And that entire higher existence, those legs of the stool that work is not the only thing in life is completely related to the fact that we've been around for 25 years. There's way too much, especially in…

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`3:00:03`

Most of the time startups go bust. Most of the time people spend five, seven years or something that does not pan out and they don't get the payout and then they just sit with regret of like, what the fuck happened to my 20s? Early on, Jason and I basically made the pact that working…

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`3:01:04`

in all the ways you've lost. When so much of life is far more open to multiple winners where we can end up with a business that have made hundreds of millions of dollars over the years, and we've kept much of that to do whatever we want and that's enough. That's good…

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`3:02:05`

when you look at who the people like you, like really smart, creative humans, who they actually are and what happiness entails. It actually entails working your whole life a little bit. It's like because you actually love the programming, you love the building, you love the designer and you don't want to exit. And…

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`3:03:05`

Yet so many think that that's why they're doing it. That's why they're sacrificing everything. Because once I get to the finish line, I'm golden. I've won, I can retire, I can sit back, I can just relax. And you find out that that kind of relaxation is actually hell. It…

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`3:04:05`

When are they happy? And what he learned was quite illuminating. He learned that people aren't happy when they sit on Mojito Island. They're not happy when they're free of all obligations and responsibilities. No, they're happy in these moments where they're reaching and stretching their capacities just beyond what they can…

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`3:05:06`

I'm just gonna sacrifice everything, my health, my family, my hobbies, my friends, but in 10 years I'm gonna make it all up because in 10 years I can do it. It never works out like that. It doesn't work out on both ends of it. It does not work out if you're…

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`3:06:08`

— You can't do it again or most people can't do it again. A, because their second idea is not gonna be as good as the first one. It is so rare to capture lightning in the bottle like we have, for example, with Basecamp. I know this from experience because I've been trying to…

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`3:07:09`

And I say bullshit in the sense of the most endearing sense. It's all great to do it. I know too much. This is one of the reasons why, whenever I'm asked the questions, if you could tell your younger self something that would really, what would you say to your younger self? I would…

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`3:08:10`

This notion that responsibility is actually key to me. "Man's Search for Meaning," Viktor Frankl talks about this as well, that we can endure any hardship if there's a reason why. Now he talked about it in truly life altering concentration can't waste. But you can also apply at a smaller scale with less…

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`3:09:13`

And so there is a degree to which you wanna make the mistake. So I think I would still give the advice of you want to have a stretch of your life where you work too hard, including a thing that fails. I don't think you can learn the lessons why that's a bad idea…

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`3:10:15`

about how when he went for a bike ride, he could go really hard all out and he could do the ride I think in whatever 19 minutes. Or he could enjoy the ride, go 5% slower, do the ride in 21 minutes and realize there's only two minutes apart. Either I go all in all…

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