Lightning in a Bottle & Knowing When to Stop

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you could do Basecamp again today? — Yeah, no way. No way. No way could I do it again. — The amount of friends that I have that sold a company — Yeah. — and just thought like, "I'm good at company building." — Yeah. — And then their second shot is not going well or ended in failure — Right. — and really made them question who they are. I think that's actually an important thing to say. It's like, maybe you don't know why it actually succeeded. — Yeah. I think that's true. You don't know why it didn't work, and you don't know why it worked. I really think that's true. — But people don't understand how devastating that is, where you sold a successful company... First of all, it's almost nearly impossible to build a successful company. — Right. Yes. — Just a tiny percentage of — Lighting in a bottle. — humans that have ever existed have been able to accomplish this goal. — Yes. — This is why I started one of the shows, because I want to celebrate the people

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that have done this and say, "Hey, if you want a role model, maybe we should... You know, people that build companies and products that make other people's lives better, those are maybe good people to listen to hear speak. They probably — Yeah. — know some shit if they've been doing it for multiple decades." — Right. — Turns out, they have a lot of wisdom, or they've acquired a lot of knowledge in that. But it's so devastating to have had that, — Yeah. — and then in the case... I always think of Trader Joe's, because again, talk about different... Me and you bond over the fact that we want to make products that are different, — Yeah. — where I'm not interested in making a me- too product. Doesn't need to exist. — Yeah. — He had a completely differentiated product. He loved it. He wrote this autobiography. It was very fascinating because he writes it... I would say 90% of the pages are building Trader Joe's. He clearly loves it. It's very difficult. — Yeah. — Just put his whole heart and soul into it.

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Then he gets scared, and he winds up selling it, I think in the 1970s, if I remember correctly. It may have been the '80s. Sold it because he was fearful. — Yeah. — Then lives another few decades. — Mm. — I think at least three, maybe four decades. — Yeah. — Like, a long time. — Yeah. — And the last 10% is like, "Yeah, I did some investing, I did some real estate, I did consulting." But then the last paragraph is, he's like, "I must admit something to my own self. I wasn't true. I regret selling." — Mm. — "Thanks for listening, Joe Coulombe..." I don't know how to pronounce his last name. I don't know how to pronounce anything. — Yeah. — I'll call him Joe Coulombe. — Do it in a French accent, please. Do it in a French accent. — But then he goes, you know, "Thanks for listening, Joe Coulombe." Book gets published, he dies the same week. — Oh! — Yeah.

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— Wow, that's quite a story. — And I always think about that when you're like... — Yeah. — This guy's life, you could tell, is full of regret. — Yeah. — Full of regret. — Yeah. I know people like that. — Yeah. — And it tends to happen in your thirties, once you've built this big thing and sold the first thing, and you're like, "I'm loaded now and I'm going to... — You have decades ahead of you. — Decades left. And it's not arrogance, it's just belief, like, "Oh, I can do that again." And some people can. Most people cannot. Or if they can, they don't reach the same height. And so, they're jumping, and it's like if you try to jump a 100 times, you can't get to those first jumps because you're tired, and that's just what ends up happening. And so then, they might build something great, but they can't see the greatness in it because it's not as great as the thing before,

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and that's even more tragic, is that they can't see something that's still an incredible achievement, but it's not the same. And other people will see it as less than, and it's just a terrible outcome. I'm afraid of it, not so much now anymore. But David and I talk about this all the time, which is, we do negative visualization, and practice. So, like AI, what if this just changes the whole damn landscape, and soft SaaS is just dead in three years? Our answer is, "Well, we had a great run." Like, 27 years, amazing, and by that time, maybe 30 years. What a run. We should be happy and proud of that experience. Not like, "Oh, damn, that sucks that we're out of this now." More like, "We should be enjoying this, and I hope we sure did,