Invest Like the Best with Patrick O'Shaughnessy
· Patrick O'Shaughnessy, David Senra
[00:00:00] S0: I don't know if it was Alan Watts that said this. He had such a way with words that maybe it was him. It might've been Joseph Campbell. But something to the effect of, we're not searching for the meaning of life but for the feeling of being alive. And I think that's correct. And I think a great... If you play red light, green light with principle, as you search for your principle, I think you could do a lot worse than knowing you're on the right path if the thing makes you feel more alive. Like, if you go in the direction… and people know what it's like to feel alive. They can call to mind these moments in their lives where they felt the most present and alive. And using those as a signpost to what your principle might be or what you should be doing, I think, is a really great thing. And that's certainly how I remember reading that line 15 years ago as well, and then starting to chase the feeling of being alive. Not a goal, but just that feeling. And everyone can answer this question, by the way. It's a really great way to have a conversation with someone, to kind of ask them where they feel this and then also why they're not doing more of whatever the answer happens to be. Which is a funny circumstance of humans, that they kind of know what makes them feel most alive and then they don't do it most of their lives. [00:00:00] S1: That's a very interesting question. What's your guess on why they don't?
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: That's a very interesting question. What's your guess on why they don't? [00:00:00] S0: Usually it's simple, which is fear. It's fear that by pursuing an original path... I have this idea that the best story always wins, and I actually spent the last couple of months really trying to figure out what do I think "best story" means. And the best principles for a great story that I could come up with were originality, hardship, and transformation. And if you dig into originality, that one is really interesting to me because people don't pursue original paths usually because they're fearful of the unknown. Because an original path, by definition, means it's all going to be on you. And that's uncomfortable and hard. And because an original path usually means leaving a very comfortable current existence in a way that's scary. And so I think when you really drill people on why not, they'll give reasons that add up to, "I'm afraid," and that's hard to get over. [00:00:00] S1: You've said to me before that you used to be a masochist for introspection. First of all, when did that stop? And then do you think that helped you find this organizing principle for your life?
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: You've said to me before that you used to be a masochist for introspection. First of all, when did that stop? And then do you think that helped you find this organizing principle for your life? [00:00:00] S0: It definitely helped me find it because I wanted to not waste life. When I was a little kid, young, five years old or whatever, I had this just crippling fear of death. Like, I remember my mom and dad would have to sit and hold my hand for me to fall asleep at night because... And the reason was I would just sit there spiraling on this crazy idea – maybe this is why I studied philosophy – that someday I would not exist, and that just freaked me out and did for decades. So that probably kicked off this introspective period of my life where I was very curious about philosophical traditions and religious traditions and metaphysics and all this kind of stuff because I wanted to know, what the hell is the point of all this? Like, what's the point? What's the meaning? What's the purpose? And otherwise, it's just terrifying, right? That we're here for a blip and then gone. [00:00:00] S1: Yeah.
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: Yeah. [00:00:00] S0: It's just terrifying. I try not to sit down and think about it too much. In fact, I'd like to move on. But that kicked off this period of, yeah, I wanted to understand myself and others, and so I was very introspective. And of course, that made me want to not live a dull life, and I was very scared of just living this train track existence. So yeah. It did help a lot. But interestingly, once I had clicked into, I think, understanding what I want to do, I don't think about it at all. And now, I have very little introspection left in my life. I used to be so obsessed with all of these personality tests and what they mean, and psychology and seeking all the modern methods for doing that, and I've kind of just lost, not total interest, but I've lost a lot of my interest in that. [00:00:00] S1: You solved the problem that you were using it for, introspection was the tool and then, like, you don't need to use the tool once the job is done. [00:00:00] S0: Yeah, maybe. Maybe that's right. [00:00:00] S1: You mentioned earlier that we have different approaches and that you wanted to talk about that. What do you think... like, I'm always curious. Again, some of this stuff I should not say on a podcast, but I'm always curious. People that know me well, like, what is their interpretation of their view of me that is different than my own? So, like, what do you think my organizing principle is? [00:00:00] S0: Your organizing principle.
· Patrick O'Shaughnessy, David Senra
[00:00:00] S0: Your organizing principle. [00:00:00] S1: If yours is just helping as many people as possible and this is what life's about and then you have all these resources to do so, through media and capital and relationships. [00:00:00] S0: Just to clarify, it's not helping as many people as possible. It is trying to see enormous, not yet realized potential. [00:00:00] S1: Okay.
· 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.