Invest Like the Best with Patrick O'Shaughnessy
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: Let's take one… just some of the most important ideas and where they came from. [00:00:00] S0: To take the simplest example possible, in the early days of the show, this is a very practical real-world example. If you take the ideas that I got from Daniel, who you mentioned before at Spotify, about how to build software. From Bret Victor, who I mentioned before about this principle for great software and what it looks like, and from a guy named Chetan Puttagunta at Benchmark, one of the partners at a very storied investing firm called Benchmark, who taught me how to sell software. Just those three guys, I basically just stole their ideas and applied it to my situation, and it worked to a spectacular degree. I didn't know anything about software. I had never built software before. I had an amazing team at the time that was able to pull it off. But the direction of the resources and what to do strategically just came from asking – you know those three are three of the greatest in the world at what they do – "How do I do this?" to somebody that could help me, and then not thinking too hard about what they tell me and just doing it and having it work. And so, there's a tiny example, three people and many more. [00:00:00] S1: Did you have all three on your podcast? You had two out of three. [00:00:00] S0: I've never met Bret. [00:00:00] S1: Okay, so you’ve had two out of three. [00:00:00] S0: Yeah. [00:00:00] S1: These ideas came from conversations that you had on the podcast?
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: These ideas came from conversations that you had on the podcast? [00:00:00] S0: No, I didn't ask them this stuff on the podcast. But in time spent just offline with them. I'll never forget, I was in Benchmark's office in San Francisco showing Chetan the demo, I'd show him the demos. And, it was amazing. He'd give me feedback. They weren't an investor in my business or anything. He was just doing it out of just the goodness of his heart, I guess. And, same thing with the others, just... and there's many more than three people that contributed to that project that influenced me and taught me things. But yeah, mostly just offline asking questions, but I did interview Chetan several times and Daniel several times. [00:00:00] S1: This goes back to the beneficial nature of relationships. You start out as like, okay, I had a conversation with them, and then if there's some kind of mutual respect, you build a relationship. Like right now, we're filming, this is the first podcast ever filmed at the Aman in New York. [00:00:00] S0: Yeah.
· Patrick O'Shaughnessy, David Senra
[00:00:00] S0: Yeah. [00:00:00] S1: You try to email the Aman in New York and ask them if they can set up and film a podcast here for free, that's not going to happen. That happens because of the relationship, a personal relationship that I have with a friend of mine who is involved with Aman. This is why I always say relationships run the world, and our jobs are essentially like learning and then taking what we learned and packaging it for the consumption of somebody else, for an easy way for somebody else to consume and benefit from that learning. Whether it's a conversation, a book review, or whatever the case is. So that's like very practical. That was in the early days when you were doing Canvas, right? [00:00:00] S0: Yeah. [00:00:00] S1: What about larger things in your life? Who do you think had an impact, like, my life would not be the same if not for that one conversation, that one idea with that person.
· 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.