Invest Like the Best with Patrick O'Shaughnessy
· Patrick O'Shaughnessy
[00:00:00] S0: And my principle is that, when I do, it is my obligation with nothing... and maybe I invest, maybe I end up benefiting, but that's not the point. It's my obligation to tell people about it and to help foster it into existence. So, you know, important difference. Well, it took me a decade to state my organizing principle, I'm not going to be able to name yours in a minute. But you're probably the most single-minded and devoted to what they do person that I know, in the sense that most people that have achieved a level of success in their field or in their job that you have, begin to branch... the world, when that happens, pulls you into this branching exercise where you end up doing a lots of different stuff. And you end up monetizing in different ways, or going into different lines of business, or changing how you do things, expanding. The single-mindedness that you have is quite distinct from the people that I know. And why are you doing it? I think you've talked about this certainly in private with me, but also in public about… we came from opposite circumstances. Like, I was born on proverbial third base, or sliding into home. I come from a history of extremely successful entrepreneurs. My great-grandfather, who had the best name ever, his name was Ignatius Aloysius O'Shaughnessy. Everyone called him IA. He was, I think, the 13th of 13 kids. He was one of the richest men in the United States. He was an oil wildcatter – first oil hole he ever drilled, I think, still pumps oil to this day in the Midwest. And so he was a giant. He was broken up in the antitrust, in the Rockefeller antitrust stuff around Standard Oil. And our family takes great inspiration from him because he made this fortune, he did not give a shit about money. He didn't really spend it, he gave away basically all of it in his lifetime, mostly anonymously. My dad tells this story about being at his funeral when my dad was 11, and all these people were there, and no one knew who they were, and my dad would go up to one and be like, "Who are you?" And they would say, "Well, Mr. IA, I cut his hair, and he put my kids through college and bought me a house," or, "Mr. IA did this, or this, or this." And we didn't even know where it went. And I have benefited from this tremendous history of business success in and around my family forever.
· Patrick O'Shaughnessy
Whereas you came from a very different set of circumstances. Our friend Sam has this idea of, there's founders of businesses and there's founders of families, and I think of you as the founder of your family. And I think that's incredibly powerful, and I think it's your greatest accomplishment that things repeat through the generations. You're fond of saying, "The story of the father and the son are the same." And it takes tremendous character, willpower, talent, lots of stuff to break from that family tradition and go a new direction, which you've done, which I just think is remarkable. And I don't know if that's the underlying why, that you refused to let your family continue to go the same direction that it had gone up until you were born. And you went, as Sam would say and we've talked about, you went searching for mentors because you didn't have them in your life, you found them in books and in founders, and you've been telling everybody about it ever since. And it worked for you to change your life and now we know, based on your work, that your work is now changing other people's lives in that same way that you changed your own first, but you were the first beneficiary of it. And so what is your principle or why? I don't know, maybe it's that you can... You don't have to just keep going the same direction that you were given, you can break off and found something new. I think that's pretty amazing.
· David Senra
[00:00:00] S1: I think there's a lot of times... I really resonate with what you said when you were, you found that book and you're like, "This paragraph, this sentence just hits you with, like, a hammer to the face." This is also like, you know, I use podcasts for this. Reading mainly, it's like, I think people are rushing through things too fast. You know, I'm famous for only listening to podcasts on 1x. Everybody's like, "Oh, you read a lot, you must read fast." I'm like, "Yeah, 25 pages an hour fast." Like, I'm not speed reading here. I think I want understanding. And I want understanding of how things actually are, not how humans say they are. And humans, not only are we lying to ourselves constantly – which, if you're lying to yourself, of course you're lying to other people about why you're doing what you're doing, or what it is that you're doing. And this is why I like autobiographies and biographies so much, because in many cases the person's like long past dead, or they're older and they're just like, "I'm writing this book when I'm 80. I'm not incentivized to lie, and here's the stuff I went through." And the trouble with whatever, being what kind of dad you are, trouble with women, trouble with business, which you realize there's nothing that you're experiencing that somebody else hasn't already experienced. And so what I want is true understanding of humanity as it is, human nature as it is, and the world that we're creating, and then I use their stories. It's not really about them, it's about you. And I think this... I don't think this has anything to do with me, I think when you watch a great movie or you hear a great story, you hear a great song, you're not thinking about, like, "Oh, this happened to Taylor Swift." You're like, "Oh, I had that same experience in this relationship." Or, "I went through this exact same thing." And it's like a form of understanding – I'm in the middle of this right now. We were just having lunch upstairs, and essentially I'm just in the middle of trying to find the story that I want to tell with this book that grabbed a hold of me for six months. And I told you about... this is Bruce Springsteen's autobiography. I don't even listen to his music. And I told you about this, like, there is stuff in this book that this dude looks like he crawled inside of my mind.
· David Senra, Patrick O'Shaughnessy
And, like, especially in regard to how he views his work and the impact that it has on... it's like, that is not a sentence, that is not a paragraph, that is, like...That was made for me to read at this point. And it's insanely powerful, to the point where it's like a drug. You know, I told you, like, right away, when you... Again, I need to give you credit. We'll go back to this drug and understanding because I think this is really important about people understanding why I want to talk to certain people and why I was freaking adamant and kind of pushing you on this, and we rescheduled a few times. I wouldn't be doing this if it wasn't for you, not only because of the platform that you gave Founders, right? The podcast. Then that crazy episode that we did together, which I think is like, we're never... like, that was like lightning in a bottle. [00:00:00] S0: It was, yeah.
· Patrick O'Shaughnessy, David Senra
[00:00:00] S0: It was, yeah. [00:00:00] S1: It's Invest Like The Best. The title is Passion & Pain, and people were always like, "Oh, like, did you guys sketch this out?" I was like, "No, Patrick doesn't sketch things out like that." He's like, "we built a friendship. I want you on the show." Like, I don't think you told me anything we were going to talk about. I do remember you texting me a few hours. We were supposed to do it at 10:00 AM. You're like, "Hey, I got pushed back. Can we do 1:00 PM?" I'm like, "Oh no, my brain only works in the morning." So I took, like, a quick power nap, and then I'm in this booth. We didn't do video, but you can see me, and I'm in, like, this phone booth that I put in my house that... I was the only person... These phone booths are in all these offices, and I had one... They came and delivered to my house, and they're like, "You know, we've never delivered to somebody's house before." I was like, "This isn't a phone booth. This is a podcast studio. This makes perfect sense to me." [00:00:00] S0: Yeah.
· Patrick O'Shaughnessy, David Senra
[00:00:00] S0: Yeah. [00:00:00] S1: And then we just had that conversation and that was a huge inflection point. Like, that weekend that happened after that was, like, one of the craziest weekends of my entire life. But then you pushed me for years. You were like, "You should be recording conversations. You should be recording these conversations. What are you doing?" And I was like, "No, no, it's a distraction. I don't want to do it, I won't do it." And then, you know, I've told this story a bunch, but I think it's really important, where I would not be doing what I'm doing right now at this very moment if we didn't have... me and you had this dinner with Daniel Ek in New York. It lasted four hours. I know you don't like when I tell you how long I talk to people. [00:00:00] S0: This is one of David's quirks. He tells you how long he talked to someone every time. [00:00:00] S1: Because I'm not in- [00:00:00] S0: You just had this four-hour lunch with so and so. [00:00:00] S1: Yeah, because I'm not interested in superficial at all. I can't tell you who it was. I just had dinner. [00:00:00] S0: How long was it?