Lightning in a Bottle & Knowing When to Stop

`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.