Lightning in a Bottle & Knowing When to Stop

`1:42:28`

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

`1:43:14`

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.

`1:44:00`

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.

`1:44:45`

— 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,

`1:45:31`

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,

`1:46:19`

because that's a rare and fortunate experience to even have that experience." But I wouldn't go and start another business after that. I would just do something else. I don't know what it would be, but I wouldn't want to try to do this again because I don't think I could. I don't think I could, and I think it's totally fair to admit, I don't think I'm good enough again to do what I did before. I don't have the stamina. I don't have the drive. I don't have the thirst and the hunger to build a brand-new software company from scratch again. I just don't. I would have the curiosity, but I know that wouldn't carry me enough. Probably early on, I was, again, more aggressive, younger, pumped, you know, it was the early days, and we were pioneers. There's that kind of energy that you have, that you just don't have again, and it's fine.

`1:47:05`

It's fine. I think one of the great... I think it was Bob Dylan, being interviewed on 16 Minutes, and I think it was Morley Safer or something was asking him about songwriting, and he was saying something... I don't know if you've seen this quote, but it's great. He was reciting one of his great songs. I forget the name of the song or whatever, and he still has an incredible memory to remember these incredible lyrics. And he's like, "I used to be able to write music like that," or "writes..." I'm paraphrasing. "I used to be able to do that. There was a certain magic to that. I don't know how I did that. I know I couldn't do it again, but I can do other things now." And when I saw that, I'm like, "That is a mature..." I mean, he's in his 80s now. I hope he's mature. But that is a mature human being to go, "I could do that before. I don't really know how I did it. Somehow I did it.

`1:47:53`

I can't do it anymore, but I can do other things." And I think that's important because if you identify as an entrepreneur and you sell your business if your identity is tied up into entrepreneurship, you have to go start another because you have to... There's continuity there, that you have to be that person again. And then if you, again, can't achieve the heights, you just feel like you're a disappointment. I've seen this in friends who've sold businesses, and it's just like, it's so sad to me to see that in them, when they can't just see that what they did was incredible, in that moment. These are moments that you have. These are periods of time that you have. These are experiences you have, and that's what happened in that time. Actually, can I go back to psychedelics for a second? — Yeah.

`1:48:40`

— I'm going to tell you a little story. I don't know if it's good or not, but it's meaningful to me. The last time I did... These are mushrooms, by the way. So, the last time I did mushrooms, I remember going into it, telling the guide I did it with, because I did it the first time, and I had this incredible experience to this one song. She was playing different songs, had this one song, that I had this experience where I just felt like I learned everything in an instant. The next time I did it, I'm like, "Can you play that song again at some point? I want to see if I have that experience again." And so she was like, "Yeah, maybe, we'll see," you know, whatever. And so, at some point, I was aware enough that she played the song, and I had no experience. It was blank and empty.

`1:49:29`

And after the song ended, I broke out in laughter, and I go, "Of course, you cannot have the same experience again. You cannot have the same experience twice. You don't deserve the same experience twice. It's not even possible to relive something again. That thing happened then, and this is now. They're detached, they're separate, they can never be the same. And it was a wonderful thing. So, I've now used that with my kids. My kids are growing up. They're 11 and seven. I'm never going to have the experience with my 11-year-old again as an 11-year-old. Once he's 12, he's 12. I can't have that again. So, you have to really savor those things now, and recognize that they are what they are now, and you will never get them again, and don't be sad about that. It just is. And that's the kind of stuff that, like,

`1:50:17`

those experiences that I had in those times, really, those are the things I carry with me, and hopefully do affect the way I move through the world now today. — That's beautiful. — Mm. — When you were talking about selling a company, and then maybe your next company in this entrepreneur's life is not as financially successful or big, — Right. —...as well-respected. I've never heard a great definition of "What success means?" And the best answer I ever heard to "What is success to you," actually came from Steve Jobs, — Mm. —...and it was beautifully simple. It was like, "Did I make something I'm proud of?" — It's good. — Yeah. — It's good. — And that's the way I think about it, is like, for your podcast, you need X amount of listeners. It's like, no, did I make something I'm proud of? — Yeah. That's great. I think that's great.