Invest Like the Best with Patrick O'Shaughnessy
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: He was very disturbed by this, and he tried to fix it. [00:00:00] S0: Yeah, I know. Yeah. He tried to... He put me through a guided, like... He tried to hypnotize me into visualizing something, and it didn't work. So anyway, the other side of that sword. It freaked me out that I couldn't see anything with my eyes closed. But the other side of that sword is like, when I'm focused on something, like here, right now, I am not thinking about other stuff. Like, it's just all this. I wish I wasn't the Eye of Sauron. That sounds so bad. [00:00:00] S1: It's said in a loving way. [00:00:00] S0: I understand. So, Sam's point was, you're red on the color wheel, and when your attention shifts, it can be whiplashy for those around you. [00:00:00] S1: What was the example he gave, though? It's too good of a story not to tell.
· Patrick O'Shaughnessy
[00:00:00] S0: The example he gave was that Sam, at the time, was raising his first fund. And I was going to be an investor in the fund. And so he called me and said, you know, "Putting this fund together. It's small, limited group of people. I'd love to have you if you want to do it." I went, "Hell yeah, I want to do it, of course," and told him the amount or whatever, and then he called me back, like, a month later, and was like, "Okay, like, I have the docs all ready, and, you know, we're ready to go. You still in for this much?" And I said something like, "Well, I can't... yes, I'm still in, but I can't do that much, because actually, like, I have also launched a fund." And he goes, "What?" And I said, "Yeah, you know, I need to make a GP commit to my own fund." And this is before I sold my business. it's a little bit, you know, tighter situation, and I have to reduce the amount. And he started to tease me, because he was like, "Wait, so when I first called you a month ago, you had never even thought about having a fund. I've never heard you talk about that. I don't think you'd ever thought about it. And now, a month later, like, you already have a fund? Like, a month later? Like, it's raised and done?" And I think that's a good example of like, yeah, some opportunity came out of left field. There was this investment opportunity in one company that led to a fund very quickly in the summer of 2020. So, yes, I like to move really, really fast when I'm interested in something, but my interest does shift around. And I don't think this is a good thing, by the way. I don't want to whiplash people, and I realized, thanks to Sam, that I was whiplashing people. I would be so excited and willing and able to galvanize people around an idea, and then I would change my... And this still happens, but I would change my mind, and completely forget about the idea. Back to, like, people that have this lack of visualization thing also have quite bad event memory.
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: Yeah. [00:00:00] S0: I don't ever think about stuff in the past, like ever. And so, not only could I change my idea, but I literally never think about that thing again that I was so passionate about in the moment, for a short period of time. And that is jarring for people that are, like, signed on to do a thing, and then a week later, you're like, "What are you talking about? What thing? We're doing this thing." And so I've worked pretty hard to narrow the... Simplify my life with rhythm and harmony, focus on fewer things, like get less distracted by what I would call, like, the flavor of the month club, which is something that can definitely snare me, for sure.
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: Yeah, now that you say that, I haven't had any, like, Eye of Sauron moments with you in quite a while. You've kind of fixed that. I heard Ari Emanuel on your podcast say something that I thought was, like, actually really smart, where he's like... His idea of, especially when he's trying to do a deal, he, like, overcommunicates. And I think a lot of that is, like, the problems... Like, I didn't understand that about you because I had never worked with you before, and then I was like, "I don't get it." Like, "What's going on here?" And then other people that knew you explained that, and then I'm like, "Oh, like, I'm having an issue..." And we've never even had an argument or a fight. I mean, one thing that I love about it is, like, we worked together for years, and we never had paper anything. We never had a contract. We just said, "Hey, this is what the agreement is." We shook hands, and like, we did what we were supposed to do up until the very... It was just, like, exactly how I want to... [00:00:00] S0: Yeah.
· Patrick O'Shaughnessy, David Senra
[00:00:00] S0: Yeah. [00:00:00] S1: I don't want to have to deal with people where there's, like, a bunch of contracts. I want to know it's like, you gave me your word, I gave you mine, and then this is what we're going to do, and we'll figure it out. But I think what was happening there is just, like, there's all this, like, unsaid stuff that you think we are looking at in the same way. And yet if we just said, "Oh wait, this is how I'm thinking about this thing, and this is how I'm thinking about that thing." And essentially just overcommunicate as much as possible with the people that are important to you, because then you're not going to have...there’s no unspoken assumption, you know? And then if you let it sit there too long, then you have another unspoken assumption on top of that one. Then things can get, like, really, really weird.
· Patrick O'Shaughnessy
[00:00:00] S0: I think a lot about leadership because ultimately, my main job is to back people with LP dollars, lots of them, that have been entrusted to me as a fiduciary, into companies led by these people that we're backing, that are usually pretty early in their company-building journey. So, mostly, you're largely backing the person and the team versus the mature business story. And pretty important that that person's a good leader. And I think one of the things I underestimated about great leaders that... Ravi Gupta is another person that I would list, and people that have really impacted me. At one point, I called everyone I knew. I was like, "Define good leader. I'm going to do a survey." And Ravi gave my favorite answer. He was like, "It's not hard. Like, a great leader is someone that other people want to follow." That's it. And everyone else had given much more ornate definitions, and Ravi's was my favorite. And what I've learned about what is shared in common amongst people that others want to follow, one of the big ones is that they are hyper-communicative with those people. And they're consistent, and they lead from the front. They take risk, they take arrows for the team, they communicate like crazy with the team. If something's changing, they overcommunicate it, you know? They're honest. Like, all these things add up to someone that people want to follow. And I think I was quite bad on that dimension for a long time, not because I was trying to be bad, just because I was so excitable. I am so excitable. Like, when I find something new and interesting, I just cannot get enough. But very often that means I'm billy-goating up ahead of the pack and forgetting that, oh wait, there are all these people that I want to do this with. I don't want to just do this alone. So, that's been a big lesson for me that has taken a while to learn, but yet another thing to credit Sam with.