Invest Like the Best with Patrick O'Shaughnessy
· Patrick O'Shaughnessy
[00:00:00] S0: That led to PositiveSum, and me building my business successfully in software got me to all of these people building early-stage companies, writing these small checks. Writing these small checks got me to this series A investment that caused me to create this new investment firm. Creating this new investment firm caused me to go invest in all these, you know, companies in a bigger way and be more impactful on them and their trajectories than I could've been on my own. The whole thing is daisy-chained together because I loved reading fucking books in my 20s and I did something about it, and I started telling other people which ones I liked. That's how it started, that's it. And all of that was unpredictable. Back to why I don't like goals, if you had told me when I sent that first email to list my goals, none of those things that I just listed would've been on my sheet. I wouldn't have even known to think about them. My own experience has cemented my belief in this growth without goals. Like, I wanted to grow. I love the idea in weightlifting, Jeremy Giffin and I talk about it all the time, of progressive overload, of always, like, a little bit harder, a little bit more. Go to failure, go to failure, go to failure. The beautiful thing about life is you don't know where that's going to take you. God, I never in a million years could've predicted any of this crap. What's even more exciting is it doesn't stop. Some set of stuff's going to happen over the next 10 years, which, if I tried to make a goal list today, I would be unable to predict. It's going to be so much fun. But it all started with I had a thing I loved naturally, I just liked to read books, and I think that's profoundly cool. Now, you know, the obligatory disclaimer is that I've been so unbelievably lucky, I had the privilege to sit and read a gazillion books and not be spending all of that time just getting ahead like you had to, because, again, I was very lucky. The situation I was born into in life with the parents I had and, you know, the things that were easy for me, I didn't have to pay for college, all this stuff made it possible for me to do these things and I think that's important to acknowledge. But nonetheless, you found your way there, you found the passion, you found the high-rep passion and now look.
· Patrick O'Shaughnessy, David Senra
That's like my constant urging to people, like, "It's there, I promise. There's something, just go find it." [00:00:00] S1: I think that was beautifully said. We haven't even touched on investing which I want to. [00:00:00] S0: Let's do it. [00:00:00] S1: I want to talk about, is it code red? Seeing red? There's this fantastic story that we've talked about before where you were going to make an investment in somebody's fund. Is it seeing red? What did this person say about you? [00:00:00] S0: He said I was red on the color wheel. [00:00:00] S1: Okay, red on the color wheel. Can you tell that story? [00:00:00] S0: Sure. So you, me, and Sam Hinkie were walking, and I think you asked Sam what's my biggest weakness or something? [00:00:00] S1: No, you were interviewing... Okay, so- [00:00:00] S0: Oh, I was doing that.
· Patrick O'Shaughnessy, David Senra
[00:00:00] S0: Oh, I was doing that. [00:00:00] S1: When you just said, like, this all started from... because I loved to read and then that started this whole chain of events, and now you have this other parallel thing that you just do compulsively that you can't help. Which is, like, exactly what you said, I'm doing 10 Invest Like The Best episodes a day, I'm doing 50 a week and I'm just recording one. Like, if we're in a group, I know what's going to happen, you're just going to start lighting people up with questions. So we go on this five-hour walk, which Sam did not like, by the way. People don't know that you're like a goddamn billy goat, okay? Like, it's just, you walk way too fast, you don't go around obstacles, you just go straight over them. That's why I call you a billy goat because they do that in real life. Like, you know, if you're out in nature and usually people, they'll say, "Oh, it's a mountain here. I'll follow the trail around it." It's like, no, billy goats just go straight over and up. And that's like walking around with you. And so we're in Columbia, Missouri, of all places, we go on this, like, five-hour walk, and essentially it's a five-hour private Invest Like The Best episode, except you're interviewing both of us. [00:00:00] S0: Yeah, yeah, I remember.
· Patrick O'Shaughnessy, David Senra
[00:00:00] S0: Yeah, yeah, I remember. [00:00:00] S1: And you would ask the other person questions about the other person and it was, like, really impactful and important for me to understand myself because again, like, somebody you trust and you know has your best interests at heart and is not trying to criticize you just for the sake of criticism. I think a lot of people are hypersensitive to criticism and if it's like some random stranger, okay, that makes sense. But you know that person cares about you. You know that person wants the best for you and they're telling this about you. Even if you don't agree, you should think about it for a little bit. And I've thought a lot about what he said over the years and I definitely agree, like he was right. So I don't know how this got turned on you, but that's when he said you're code red – no. [00:00:00] S0: Red on the color wheel. [00:00:00] S1: There you go. What does that mean?
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: There you go. What does that mean? [00:00:00] S0: First, just a thought on Sam, which is it's hard to imagine a higher compliment I could pay someone than the role that Sam plays in my life. The way I would phrase it maybe is I have more conversations with Sam when he's not there than when he is. What I mean by that is I'm often finding myself wondering, in a situation like, "What would Sam think about what I'm going to do here?" I so value his character and judgment and fidelity and just so many things about him. But, like, what a role to play in somebody's life. Like, he's the one I invoke in my head, one of three or four people that I invoke in my head of like, "What would this person think about this thing I'm about to decide on?" But back to the story. So he said, yeah, it was something like, "what's my biggest weakness?" And he described me as being red on the color wheel, which he explained meant that when I'm interested in something, I am intense. And I've always been this way. I am voracious and intense and aggressive and I would say I have a skill at making things happen when I'm interested in them happening, and maybe that's one side of the sword. The other side of being red on the color wheel is this, like, locked-in intensity. The other side of it is that the moment that attention is focused elsewhere, I can tend to whiplash around a lot and change my opinion really fast. [00:00:00] S1: This is known lovingly amongst your friends as your Eye of Sauron. [00:00:00] S0: Okay.
· Patrick O'Shaughnessy, David Senra
[00:00:00] S0: Okay. [00:00:00] S1: Where like, if Patrick is focused on you, like, he will make shit happen. But if it's elsewhere, you're not... I've had to fly literally to Greenwich, like, "Dude, get back on, like, we need to focus on this." I had to get in your, because you're… in some cases it's like a physical presence thing. [00:00:00] S0: Yeah, yeah. [00:00:00] S1: It's not just like, "I can get you on the phone," but I was like, "No, no, this is not good enough." So that's the strength, your strength can be your weakness. [00:00:00] S0: You know, it's interesting. I learned something about myself recently, which I, at first, was terrified about, and now I've come to view as everything is double-edged, you know? Which is if you close your eyes and try to visualize something, a red cardinal or something, there's a degree of how visually sharp that thing looks in your mind's eye when you close your eyes. For me, it's just black. I can't visualize anything. I can't see anything. I'm like, wait... I discovered this, like, a year ago. I'm like, "Wait a minute, you can see things with your eyes closed?" Like, "What are you talking about?" [00:00:00] S1: Do you remember we were at Brad Jacobs’ house having breakfast or something? [00:00:00] S0: Yeah, yeah. [00:00:00] S1: He was very disturbed by this, and he tried to fix it.