Patrick O'Shaughnessy, Colossus & Positive Sum artwork

Patrick O'Shaughnessy, Colossus & Positive Sum

David Senra

December 21, 2025

Patrick O'Shaughnessy is the Chairman Emeritus of O'Shaughnessy Asset Management, the founder of Colossus, and the founder and CEO of Positive Sum. He is an investor, author, and podcaster who has devoted his career to understanding the world's best investors and entrepreneurs.
Speakers: David Senra, Patrick O'Shaughnessy
**David Senra** (0:02)
You have this almost obsession with finding talented but not well known or relatively unknown people, and then you essentially spend a lot of time talking to them, develop relationships, and then putting all of your resources behind that person.

**Patrick O'Shaughnessy** (0:21)
Yeah.

**David Senra** (0:21)
What is going on there?

**Patrick O'Shaughnessy** (0:23)
Well, for how my personality is wired, that is the most exciting possible thing to do. Because it means I get to learn about a person and whatever they're doing before other people do, and I like that. I like being at the frontier of what's going on, and learning things that aren't widely known. I just enjoy that. I read so much and I've spent my whole life just as a constant learning type person. So to find something fresh and new is very exciting to me, and you can usually do that with people like this. Then I've just learned about myself that by far my favorite thing in the world is championing other people. That's just what I enjoy doing. If I look back on my life, the winds that I've had, the things that if you were to write a Wikipedia article about me, would be the accolades or the accomplishments. I don't care about those things. I don't think about them. When they happened, they didn't do anything for me emotionally or otherwise.
For whatever reason, that's just not what I enjoy.
But when your success happens or when many other people that I and my team have championed have a win, I feel that deep in my soul and heart and gut in a way that is just more gratifying to me than anything else in the world. This extends to my kids, my wife, my friends, the CEOs of companies that we've invested in, people that we have on our show, that we tell the world about. That's the repeated thing that I love. And I also kind of like picking sides. I like saying, I like this person. And by extension, I like them more than the other available options in this field or this industry or whatever. And I just get tremendous joy out of that. So now I'm architecting my life to just be able to do as much of that as possible. And I hope I get to do it for a long time.

**David Senra** (2:21)
I screenshotted this text, this was like many years ago. Somebody was asking me, I can't remember who it was now, but they were asking me like what Patrick is like. And I was just like, well, Positive Sum is definitely like a way to describe him. I was like, and he doesn't do things for money. Like that doesn't mean he's not commercial. Like he makes a lot of money. He's going to continue to make a lot of money. But that's like not the driver behind it. Let me go back to like one of the craziest days of my life has directly involved you, right? Like I was like in the middle of this like five and a half year struggle of like being obsessed with something I know I truly cared and thought was really good. But the external world was like, no, like nobody gives a shit about what you're doing, David. And you know, I kept doing it. And we have a mutual friend in Sam Hinkie who's going to keep getting annoyed because I bring him up on every podcast I go on.

**Patrick O'Shaughnessy** (3:12)
Because like he's deserving of the mentions.

**David Senra** (3:14)
The two episodes he did with you, like especially the one about like Find Your People, I think is that I go back to that one all the time and the notes that he says in there. And like one of the things I think about all the time, which again, I'm not an investor, but I want like access and I want deep relationships with people, very high quality people. And it's just like he's like, people are power law and the best ones change everything. And so once you actually see that, you are very, almost like ruthless with who you let have access to you. And I think I'm getting very ruthless and continue to be ruthless because of what I'm kind of chasing after. But I had like no followers on Twitter at all. And just like tweeting into the oblivion, like no one gave a shit what I'm doing. And one day, this is why it's like one of the first things that I think speaks volumes about you and how you actually live your life. And like I think you've now leaned into this more over the last four years that we've been talking.

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