Invest Like the Best with Patrick O'Shaughnessy
· Patrick O'Shaughnessy
[00:00:00] S0: Two people came to mind right away. The first is Herb Allen from Allen & Company, who I don't know well. These lessons came from one incredibly interesting conversation about… my sense of him – again, don't know him well – is that he is uncompromising in his values. He's maybe the apex predator of the thing I want to do, which is like picking and supporting people. I think that's what he's done for a really long time with unbelievable success. And that he is so incredibly uncompromising about how he does that and willing, I won't tell the examples, but I think willing famously to throw away huge commercial opportunities just because the person wasn't who he wanted to support. Sometimes it's literally a conversation with a person that just smacks you in the face and makes you feel validated, maybe for what you're trying to do. There's a gentleman named Reece Duca who's very, very private. And there's no content about him or interviews with him. I wish to God he would let me interview him. I know he never will. Who has been incredibly impactful at a philosophical level, he has all these amazing little phrases, but his life kind of boils down to simplicity, the beauty of simplicity. He gave me this line one time, "Simplify your life with rhythm and harmony." And that line is what you're talking about. Fewer deeper relationships, fewer things better, everything aligned with what gives you energy, listening to your own, the feeling of aliveness. He lived that to a degree that's rare, that I've never seen. So, I could keep, I literally could rattle names. A gentleman that I spend a ton of time with now named Jesse Beyroutey, who I am with basically every day, who also I think has no interest in fame or accolades or recognition, but I think is one of the great – will go down, I would predict, as one of the great investors ever. And he's like Reece, he's completely uncompromising and has the most principled way of living I've ever seen. Just like, refuses to get sucked into the game. God, man, I could rattle off names for hours and hours. I mean, there's so many people that have influenced me. And that's what makes this all fun, that's what makes what you and I do so fun, is I'm inspired constantly. And you're doing this new show. I interview people once a week, but really I interview 10 people a day. That's what I do.
· Patrick O'Shaughnessy, David Senra
I just happen to have mics there one of the times, if I'm doing it 40 or 50 times a week, which is not an exaggeration. It really is that many people every week, just like, "Who are you? What's your deal?" I love doing that. And there's just too many, too many to name, but those are a couple that came to mind. [00:00:00] S1: Munger said, I'm paraphrasing, but he's like, you know, "One of the best ways to learn is, like, you find somebody that's kind of an outlier and you just ask them, like, 'What the hell is going on with this person?'" [00:00:00] S0: Yeah. [00:00:00] S1: And you just keep asking that question to try to get deeper and deeper and deeper about like, reverse engineer of what they're doing and why they're really successful. There's another fascinating thing where there's like, this meme where it's like everybody has a podcast now, and everybody starts podcasts. And as soon as that takes hold, you've been doing podcasting for 10 years, and you decide, "No, I'm going to go in a different direction." And the majority of our conversations, I would say, now are not even about the podcast, they're about these profiles that you're writing on Colossus. Some of them have been so incredible that I actually used them as source material for a "Founders" episode. Which I think, we should do more of those collabs, because I was like, they were really well written. Kind of, like, doing my job for me. [00:00:00] S0: Yeah. [00:00:00] S1: Why did you decide to do that?
· Patrick O'Shaughnessy
[00:00:00] S0: I'm, in the abstract, very interested in how I can create and control valuable scarce units of attention and then dole those things out to the people that we believe in. At a very high level, the reason we now have a magazine, which on its face I think everyone would've agreed was a stupid idea, or told me it was a stupid idea when we started it. Why are we doing these profiles that take months or quarters or years to write and require lots of investment? Why do them? Well, the reason is, I think it's just a beautiful way to shine the light beyond, like, podcasting on people that we admire, and to teach someone, to teach the world about a compelling founder or a compelling investor or artist or whatever. And the thing that I didn't realize with that was that because I'm not writing the profiles, our amazing team is writing them, it would actually be a double whammy that not only… when we started doing this, I went and read David Remnick, who's the editor, longtime editor for The New Yorker. And New Yorker profiles were always my favorite growing up, these incredibly detailed, amazing, well-written profiles. He wrote in the introduction to this – his compilation of his favorite New Yorker profiles. There's this line that says, "The best profiles over the last 100 years are defined by somebody doing a thing they're obsessed with and a writer that is as obsessed with the person as the person is with the thing." And I remember reading that paragraph and just thinking, "Wow, that's what I want to read." And so I went and I read a million profiles, and the very best one I read was in a publication called Tablet on Palmer Luckey from Anduril. And I reached out to the author, his name is Jeremy Stern, who's now the editor-in-chief at Colossus, and the rest of that story is sort of history. He joined, we've got other people that have joined or are joining to write these profiles. And it just felt like, wow, this is another way to do the thing we love to do, which is to find the person, become obsessed, learn everything about them, take great time and pain to write a definitive thing about them, and then share it with millions of people. And, you know the fact, the one that we wrote about, Josh Kushner and Thrive, was one of these bizarre "break the internet" moments when it just like, completely took over the internet for a while.
· Patrick O'Shaughnessy
And I remember reading it the first time, and I was, like, 45 minutes into reading it, and I was still reading about the Holocaust. And I don't think anyone else would take that risk in a profile of Josh and his family and his team, but it was so important to understanding the soil out of which his family and eventually he emerged. And Jeremy also, the writer, was the product of Holocaust survivors himself and knew a tremendous amount about Josh's family history because it was also his family's history. And I thought that was the coolest, most beautiful thing. I would never have written… you know, this project has become an excuse to first of all, find more talented people, the writers, that we can support, which is great. See the potential, you know? Same thing we've been talking about over and over again. So now team members become more people that we can do this supporting thing with, and for them to write things they're obsessed with and passionate about, and then for the rest of the world to benefit, for the people being profiled hopefully to benefit if we tell the honest stories, and we want to tell the hard parts and the interesting parts. And it's been successful beyond what I ever could've imagined. And I think it's important to note, when I started with the first idea, everyone said it was stupid… I mean, literally everybody said it was a stupid idea. When I started the podcast, everyone said it was a stupid idea. When we started Canvas, everyone said it... I think if people say something's a good idea, I always get a little nervous because if it sounds like a good idea, it just feels you're in a more competitive space, it's going to be harder. I think the key is stuff that sounds dumb but isn't. And I think that's what I would, you know, starting a magazine in 2025 I think falls in that category of, "Sounds dumb, magazines are dead or dying. " But the thing underneath it was this desire to have more ways to do the thing that we love to do, which is find people, learn about them, tell the world about them. I suspect it won't be long until that's much bigger than even the podcast, which itself is, you know, very, very big.
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: The surprising thing is I think you want that to be the case. [00:00:00] S0: What specifically? [00:00:00] S1: Colossus being bigger than the podcast. [00:00:00] S0: Of course. [00:00:00] S1: That's not an "of course" thing, you've got to unpack that. You've got to explain why you feel that way. I know you don't know how other people view you, but I get a lot of this because they know of our association. They're like, "This is the best business interviewer in the world and this is incredible. Like, why would he not want that to be the biggest thing?" [00:00:00] S0: I'm not saying… I want to keep doing that. [00:00:00] S1: I know you, I know that. [00:00:00] S0: For sure. I love it. [00:00:00] S1: But I think in your heart, if you had to choose, you'd be like, "No, I'd rather have the profiles be bigger." Cause you like, again this goes back to how we started the conversation. Like, I really do believe you would like to be the guy behind the guy.
· Patrick O'Shaughnessy
[00:00:00] S0: That's true, but the reason for me is almost so obvious that it's uninteresting, which is, well, if a bunch of other talented people are doing this and then creating these things, first of all, I'll have more of them, so I can enjoy them more. And I'll get to enjoy it just like everybody else. Like, I can't tell you how fun it is to get the first draft of one of these things in Slack. The things that make me the most giddy in my work are some new draft that they've created for Colossus and some new research reports on an investment created by my incredible team on that side, who, in many ways, are just doing the... it's turtles all the way down, like it's the same deep investigation, publishing, writing, clear thinking. When I get one of those two things in the morning, sometimes there's days where I have several of them, those are the best days. And so, selfishly, I would just love a world where I'm not needed at all because that means we're creating more of them. Obviously, I'm limited by my own bandwidth and time. I'll always do interviews. I hope it gets bigger and bigger and I don't want to fade into the sunset. But I hope this is much bigger, because that means I get to hire more incredible, talented people and hopefully put them on a career trajectory that's the best it could possibly be, and that's incredibly gratifying. I get to read more of these things. I get to do this thing that we love to do for more people and point the light that we're trying to cultivate on more and more talented people. That's unbelievably exciting. I hope it's not just writing. I hope it's a documentary. Who knows where it goes? I hope we start convening people in small situations where, "Meet this person. Meet this person." Like, that, to me, is the most fun thing in the world. And so, a world where it's no longer rate limited by my time and energy is much more exciting than a world where it's me. So yes, I would vastly prefer that all the rest dwarfs whatever I do, even though I hope what I do lasts forever and is big itself.