Invest Like the Best with Patrick O'Shaughnessy
· Patrick O'Shaughnessy
[00:00:00] S0: A lifelong quest to build something for others that expresses who you are. And we have trained ourselves to see this in people. By the way, the best way to figure this out, my favorite question for founders is literally just give me two hours, tell me your whole life story up until the point you founded your company. We'll talk about your company later. Like, just tell me what got you to here. Back to best story wins. Originality, hardship, transformation. In the business context, it's, I want someone that's lived a very unique path. I find success in startups is the result of path dependency very often. Some unique set of lessons and experience led to you being the right person to do this thing. And then hardship, of course, you know, the harder the business is to build, the harder it will be to copy. I think that's really important. Transformation is about the customer. You know, if you build something crazy hard, the customer's life will get way better service. So, I think this powerful concept of life's work can be applied to ourselves, to make great investments. And it's really rare, but the leadership qualities of like, the reward for great work is more work. The reason I started talking about life's work and investing is these people come to realize you will not be rewarded with great work if you do not become a good leader. And a common pitfall that I certainly have fallen in before is, when there's someone really talented, they can do a lot themselves. They can get a lot done themselves. And I refer to this as, like, heroics. And that's always necessary. A founder always is the flame keeper of the spirit of the company. And I think founder-led companies are, of course, so much more interesting, preaching to the choir here, than professionally managed companies for the most part. But I do think that, like, becoming a great leader becomes the most important way to secure more right to do great work.
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: Is there anybody that you admire that was doing great work and then stopped? Whether they sold their company, they retired, whatever the case is? Is there anybody that you know that, like, you admire personally that stopped? [00:00:00] S0: There are tons of people I admire who change what they do a lot, or have changed what they do a lot, who stopped one thing and went to another thing. [00:00:00] S1: But they're doing something.
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: But they're doing something. [00:00:00] S0: Yeah. I don't... I’m just wired this way. You are, too. I just need to be doing something. I can't sit around. And so, I'm drawn to people that want to make stuff. And so, I have tons of examples of people who have tried lots of things and made lots of things and moved on from things and had chapters in their life, and then a new chapter with doing something totally different. There's one investor that comes to mind, whose name is John Pfeffer. And John has been wildly successful in like the... it's almost like he picks whatever he's doing, and as it gets to the tail end of it, he tries to find, like, the thing in the world that is the most different from what he's doing. He says with glee, that require him completely abandon his current network because they're irrelevant for it. Like, one time, he went from being one of the key guys at KKR, and then went to be, like, one of the most important guys in cryptocurrency, and then he went from that to building, like, a grocery store chain in the UK. And each time, he's like, "I literally had to start from scratch, and I love it. Like, I had to build a completely new network of people." And so, I know lots of people like John, who have successfully hopped around. You know, I know your focus is more on people that do a thing for a really, really long time. But I don't spend a lot of time with people that were prolific creators of things that just stopped.
· David Senra
[00:00:00] S1: I think they're the saddest people. Like, you're in this infinite game, and there's some set of circumstances that cause you to, like, make that decision and...
· 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.