Asked what he would tell his younger self, Selby says he has been too cautious to play momentum markets, and explains why he doesn't chase venture rounds at today's AI valuations.
…land your lap or to mix metaphors, the music stops and you don't have a chair to sit in, it's a great way to make money. And I just have it's just my personality to just fight that and not play in that type of momentum market. And that has probably been a costly mistake, but it is what it is.
So another way you want to play investing games, not narrative games. I'm
an investor. I'm not a trader. The market and venture for the last several years has been a trading market. Like you can't underwrite Anthropic at $2 trillion. There's no way you can do that. There's no way anyone can do that. It's a trading market. So I'm an investor. And so I need to be able to get out my pencil and make the assumptions and underwrite the deal. That's what I do. And so that serves me well with what I do. And, you know, when this market currently corrects, which it will happen, it'll be when, not if, I will be relatively fine. And when our trader friends who are investing in these crazy valuations, they will not. But in the meantime, they've made a ton of money.
Just to go contrarian on your mistake, I study the compounding of things. I'm obsessed with this concept of different things compounding. I think much more things compound than people realize. Is there not a compounding to being more of a fundamental investor that could compound throughout your…
I think so. I mean, when the current market corrects, the only impact that it'll have on what I do with my Copper Sky strategy is it will make the multiples that when I take my companies to Sandhill Road, the multiples undoubtedly will contract. And that will have an impact on what I do. But…
Well, Jack, this has been absolute masterclass. Thanks so much for jumping on. Thanks