Invest Like the Best with Patrick O'Shaughnessy
· 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.
· David Senra
[00:00:00] S1: I think this, exactly what we talked about today is, like, why I'm so obsessed with having conversations with, you know, people I find interesting, obviously people I have, like, deep relationships with because this is why I'm going to keep holding onto this idea that I'm not interviewing people, I'm having conversations, because we talk all the time. I had no idea where this conversation was going, and it went in places... Like, I had learned stuff about you that I did not know. And so I really appreciate you saying yes to me and coming kicking and screaming on. I want to end by turning it around on you. What is the kindest thing someone's ever done for you?
· Patrick O'Shaughnessy
[00:00:00] S0: One is... they're related. So, I'll tell them in order. The first was, I had a cousin. I come from an Irish Catholic family where, when you go to the family reunion, you get a sheet that looks like one of those maps from the '90s where you just have to, like, keep unfolding it because there's just so goddamn many people. And so I have cousins who are technically my, like, third or fourth cousins that feel, in my family, more like a first cousin. One of my third cousins was a guy named Tim O'Shaughnessy, and when I... I was a bad student in high school. I was, like, a very good student as a young kid. I went to this giant high school in Connecticut, like 4,000 students, and I just partied way too hard and didn't get good grades and didn't take it seriously. And so, there was a day... I remember it very distinctly. I was at a friend's house, having stayed up too late the night before, and my dad called me and said, "Hey, you know, you should probably come home. There's a whole bunch of very small envelopes here from colleges." So, I actually got rejected from every college I applied to the first time I applied to colleges, and I got all the rejection letters on the same day. It was a bad day. So, then I reapplied to some other schools. I had wanted to go to the University of Notre Dame, and I called them, and I said, "Where are some schools that have a compatible curriculum with yours? Because I would really love to work hard and then transfer." So, they gave me a list, I went to one of those schools, I got very good grades, I transferred to Notre Dame. So, now I'm a sophomore at Notre Dame. And I didn't know anybody. It's not like freshman year, where you have all this amazing orientation. You're a transfer student, they're like, "Here's your room number. Like, see you later." So, I met, like, a couple of other transfer students, and that was it. And back to being shy, like, I wasn't at the time good at navigating a new social situation. I just wasn't good at it. So, Tim, who I had met, like, maybe... I didn't know Tim well. You know, Tim was from the Midwest. I didn't know him that well growing up. He took it upon himself to come meet me, find me. I remember very distinctly he brought me a fake ID. He went so out of his way for, like, the first six months to, like, organ transplant me into his social circle.