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James O'Shaughnessy

James O'Shaughnessy

American investor and venture capitalist

Feb 17, 2026

20:36
So when you think about the whole of your career, what factors do you think investors can kinda take to the bank in terms of how they might construct their portfolios, whether they're individual stock investors or using funds? Which do you think have some predictive power and could carry them forward to better results?
20:56
So my advice in this regard tends to be really boring, um, because I think that the vast majority of investors would be well-served to think of their future selves.
21:11
We really tend to be hyperbolic discounters, um, and that really skews our ability to think about, you know, when do I...
21:20
Let's say you're 45 or you're 50, right? And you wanna retire from your job at the traditional age of 65.
21:28
You've still got another 15 years, right? And when I see it happen with young people, that really kills me because young people are time billionaires, right? And so the simplest advice I think is also the best, and that is understand why you're investing in the first place.
21:47
It's not to have a blast.
21:49
It's not to have fun.

20 MINS LATER

41:37
You know, what was, what was the genesis for this book?
JordiHOST
13:28
Patrick, why don't you jump off? Uh, you shouldn't need an introduction at this point, but introduce yourself, and then we'll get into, uh, the news with DoorDash.
13:34
Sure.
13:34
I'm, I'm Patrick O'Shaughnessy.
13:36
I run a media business called Colossus and an investment business called Positive Sum.
13:41
Uh, the, the shared DNA between the two of them is looking for the very best stories, to interview the people, profile the firms, invest in the businesses.
13:49
Uh, so we try to do that all year, every year.
Tony Xu
Tony XuGUEST
17:01
Yeah.
17:01
And when I asked around amongst friends that cover the business, the common thing that you'd hear was that Tony's ability to get in- and the business's ability to get into, like, the fine-grain, tiny details that, like, all p- all tied together was unlike anybody else.

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