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My First Million · Startups & Venture · October 2026
Kokonas, who has moved from options trading to restaurants to reservation software, explains why he keeps starting over. He says it gets harder with age, and that once you've had some success there is little incentive to quit and lose money for a while.
Yeah, the ladder. What
is, what is it? What are you looking for?
We're here for whatever decades if we're lucky. And in order to keep learning and keep young and wake up, like you guys were coming today. They showed up at what, 6:30, 6:15, something like that. I get excited by that. It's exciting to be uncomfortable in the sense of, hey, we're doing something today. We're making this little thing here. And who knows what that'll lead to and all of that. And if you just put yourself out to pasture, essentially, once you get good at something, it's very, very easy to fall into, well, I'm making good money and I know what I'm doing. And I'm kind of an expert in it now. And expertise is such a trap, right? It's such a trap. And you know that a non-expert is going to come after you. Like once you get to expert level, you're screwed because somebody who's younger, hungrier, fresher eyes, more willing to break convention to find the new way through is going to kick your ass. So before your ass gets kicked, you should quit. It's really hard to do. And then go find something new. And it's really hard. The older you get, the slower you get at doing that, the less incentive you have to do it. Right.…
What's the quote? You know, most men die at 25. They're buried at 75. Or, you know, I think Naval says as well, like the great, the great ones, the truly great ones, they're great because not because they've reached the top of a mountain, it's because they are willing to go back to the bottom of…
One of the things my dad had on his desk was a little Sisyphus. I've got that, you know, always on my desk. I've had it on my desk forever. And for me, like the Sisyphus thing is like, shit, we got to wake up. And, you know, I'm building a wine bar here. Like, I got out of the restaurant, but we'll…
Build a new restaurant. Bring out the boulder. Yeah, right, right, right. Found a new hill. Yeah, yeah, yeah.