Invest Like the Best with Patrick O'Shaughnessy
· Patrick O'Shaughnessy
[00:00:00] S0: Here's an example. There's this really fun game. You can do it with your friends. You sit down, and on a piece of paper, you write down 10 roles that you play in the world. Podcaster, father, whatever, friend. And then you tear them up… so it's just on, you know, one thing on each sheet of paper. And then you have to, in reverse order, ten down to one, slowly throw the roles away until you're left with one. Okay? So, one role left. It's a really interesting game. It's interesting for yourself, but also super interesting to see what your friends pick. First of all, what's on the list of 10? You can do this with attributes for yourself, too. Curious, hardworking, whatever, and then jettison those one by one. Fun game. I played this with my wife and my kids and my in-laws one time, and I'll never forget it. My father-in-law had a very, very successful career as an entrepreneur and executive in the kind of healthcare and insurance world. And we were doing this game, and his last one was grandfather. So, that was, like, the role that he kept as his final, most important one. And he is an unbelievable grandfather, like, the Michael Jordan of grandfathers. Like, he is unbelievably good at being a grandfather. It's like, makes me emotional thinking about it, and so thankful for it. And the difference it makes in my kid's life and his other grandkid's life, it's extraordinary. And so, Dan is his name. Dan is no longer a major healthcare executive. He's still an entrepreneur. He's not given it up completely, but he definitely devotes himself more to something like that, which in some sense is much smaller, and in other senses, the biggest possible thing you could do. And so, even the people that sort of, like, stop the commercial side, that I love, tend to find a thing to pour themselves into. And in this case, it's the same thing we've been talking about this whole time. It's an act of service to show up at everything, to be the most reliable, to be the most fun, just over and over and over again. In this case, in the role of a grandfather. So, I think that's exciting for my own life, that maybe when I'm 70, I won't do any of this stuff, and I'll do something else that's totally different.
· Patrick O'Shaughnessy, David Senra
But my attitude towards it, hopefully, will be the same, and that will be because I've gotten the privilege of watching people like him do that sort of role at that stage of their life. So, back to your original question, the people I love and admire most do pour themselves into what they're doing regardless of what that role is, even as that role shifts around as life goes on. [00:00:00] S1: You gave me this term that we describe people that we don't want to spend time with, that now I think I just use and I make that I came up with it. And it's casual. It's like, do you want to go to dinner with this person, or do you want to meet this person? And, like, shorthand between me and you, we're always like, "No, they're casual." Like, they're just not... It's the exact opposite. That's a beautiful story. Like, I went from, "I pity these people that don't work anymore," to like, "That person's better than I am. That guy's a better person than I am." [00:00:00] S0: I mean, honestly, there's something very beautiful about the scope of the ambition shrinking so narrow. We talk a lot about, you know, The Trillion Dollar Coach. What's his first name, last name? [00:00:00] S1: Bill Campbell.
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: Bill Campbell. [00:00:00] S0: Bill Campbell. I never met Bill Campbell. I wish I had. It's this beautiful archetype of older guy, just working with a couple executives. Now, he worked with Google, and, you know, some of the most famous companies, but was apparently, like, transformative in the lives of these people. But it was, like, five people or three people, or whatever small set of people, and that's it. And he wasn't doing it for money, or fame, or power, or any of this stuff. He was just doing it to help these couple people. I think that's a really cool exercise to be like, "What if the only thing I was allowed to do in my life, nothing else was allowed, was help three people. Who would they be, and what would I do for them?" Dan helping his four grandkids or something like that. That makes me excited for later stages of life, when I think the ability to do something like that goes up. And that is every bit as successful in my mind and in my book as Elon Musk or Jeff Bezos or, you know, pick the people that we all worship in the business world. I'm amazed by them too, but there are flavors of success. And to me, that sort of devotion, even if it's to one person, to your wife, to your kids, whatever, is every bit as successful, and if not more so, because that shit will ripple through history. My son and my daughter will now behave differently because of the experience that Dan and my mother-in-law and my dad and my mom gave to my kids. So, what's better than that?
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: And it is so unusual for us to even contemplate that some of the decisions you're making right now are going to ripple through the generations, they're going to affect things way after you're gone. We talked about this, I think, yesterday. Somebody took a bunch of, like, interviews I'd done and stuff I said on the podcast and, like, literally made, like, a hip-hop album, and there's, like, an eight-track hip-hop album. I think it's called, like, "David Senra: Founders" or something like that, and we keep talking about it, but I sent it to Hinkie because the first one was like this idea of a generational inflection point. [00:00:00] S0: Yeah. [00:00:00] S1: Generational inflection point, which is like the founder of the family. And, you know, Hinkie is rather religious in a way that maybe I'm not. And, you know, he's like, "Did you script this out?" I was like, "No, I didn't." He's like, "Did you know about this?" I was like, "No, like, somebody just sent it to me. Like, I didn't... You think I'm making music by myself? Like, come on here, that's..." [00:00:00] S0: I wouldn't put it past you.
· Patrick O'Shaughnessy, David Senra
[00:00:00] S0: I wouldn't put it past you. [00:00:00] S1: And so I was like, "No." And, you know, he's like, "Yeah, I listened to a bunch of them, but, like, that first song," he's like, "That's obviously like a sign from God. You should consider it a sign from God." I'm like, "What? What is this?" And we were on the phone, I was like, "What are you talking about?" The reason that came to mind is because in that song, I guess I talked about, I think it was on your show, where I was just like, you know, this choice by this man I don't remember and I never met... I met him, but I don't remember him. Which is my grandfather, who was 30 years old, living in Cuba, no education, doesn't speak English, doesn't have money, has two jobs, works in a shoe factory, and is a butcher, somehow realized, "Oh, Fidel Castro. This is probably bad. I have to go to a country that, like, I don't know anybody." [00:00:00] S0: "I'm outta here." [00:00:00] S1: Yeah, didn't speak the language. And like, that's just one choice. You know, three decades later, whatever, I'm going to be born, and now I'm born in, you know, a capitalistic, greatest country, in my opinion, greatest country in the world, as opposed to that. Like, that one decision by somebody I don't remember, like, ripples through the entire generations. Which I think is a very interesting thing to contemplate when you're trying to make your decisions. The last thing on his list was grandfather. What was the last thing on yours?
· Patrick O'Shaughnessy
[00:00:00] S0: The story was so overwhelming, I honestly don't remember. It was probably husband or father, one of those two. To me, those are the most interesting roles in life. You know, you and I have talked... You know how I feel about those two things. And so it was probably one of those two, or I probably cheated and said, "Can I have both?" And, you know, I hope it's that until it's grandfather, I guess. But the available... I said something like this earlier, but the depths available in those relationships are crazy to me. I can't believe that every couple years, I find a new level of those things. I just can't believe it. Every time it happens, I'm like, "I can't believe this is happening again." And in terms of, like, a place that can yield rewards, those are the most interesting to me. But more generally, like, maybe this is the theme of our conversation today, the small set of relationships with people for whom I would do anything. And that's how I'm wired. Like, there is a certain category of person, you're one of them, that... whatever you need. You don't need to explain it, I'll do it. And getting to that point with people, I don't think it... life's too short, and, you know, there's only so much energy in a day, and so you can't do this for a thousand people. But you can do it for 10 or 15. You know, follow Dunbar's number or something, you could probably do it for 15, and that is my prized possession. That list of people for whom I would do anything is my prized possession. And I think that that can probably be true for just about anybody. And so I try, hope, to act in a certain way to deserve that group of people, and even if they don't feel the same way about me, that's okay. If I'm in their list of 50 and not 15, it's fine. Yeah, I think that that role game is quite fun because I think it pulls out of you, like, where you have the most energy.