David Senra: You have this almost obsession with finding talented but not well-known or relatively unknown people.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And then you essentially spend a lot of time talking to them, developing relationships, and then putting all of your resources behind that person.

Patrick O'Shaughnessy: Yeah.

David Senra: What is going on there?

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: I read so much and have 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. And 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.

Patrick O'Shaughnessy: If I look back on my life, the sort of, like, wins that I've had, the things that if you were to write, like, 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.

Patrick O'Shaughnessy: 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, and 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.

Patrick O'Shaughnessy: 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: 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 what Patrick was like, and I was just like, "Well, 'positive sum' is definitely, like, a way to describe him," was like, and he doesn't do things for money. 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 one of the craziest days of my life has directly involved you, right?

David Senra: Like, I was in the middle of this five and a half year struggle of being obsessed with something I know I truly cared and thought was really good but the external world was like, "No."

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: Yeah.

David Senra: 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. Because like-

Patrick O'Shaughnessy: He's deserving of the mentions.

David Senra: The two episodes he did with you, especially the one about, like, find your people, I think, I go back to that one all the time and the notes that he says in there. And, like, one of the things that 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."

Patrick O'Shaughnessy: Mm-hmm. The beautiful one.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: 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've gotten very ruthless and continue to be ruthless because of, like, what I'm kind of chasing after. But I had no followers on Twitter at all and just tweeting into the oblivion. Like, no one gave a shit what I'm doing, and one day...

Patrick O'Shaughnessy: Yeah.

David Senra: This is why it's 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, and I'm like, see a bunch of notifications on Twitter. I'm like, "I don't get notifications on Twitter." Like, "What is this?" There used to be a same guy that had my name, and he was a Brazilian MMA fighter, so when he would fight...

Patrick O'Shaughnessy: Oh, that's funny.

David Senra: Yeah. It's like-- So, but all the tweets were in Portuguese, so I don't know what they're talking about. It's just not about my podcast. And I almost remember verbatim, I should go and find, see how much I get the text inside the tweet correct, but you were like, "I never find new podcasts to listen to," and, you know, that's, like, the best. It's just like people don't know, it's just like, insanely, one of the most insanely valuable audiences in the world.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: If you could sketch out the average net worth of listeners to this, it's just, like, mind-boggling, and we're about to see that in action with this story. And you're like, "I never find new podcasts to listen to. I think David Senra's Founders Podcast is excellent. You should listen to it." And you linked to an episode on Estee Lauder, which is one of my favorite one.

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: I love that episode. Yeah.

David Senra: And you send me a link, and so at the time, it was a paywalled podcast because I couldn't figure out the business model because I had no listeners. And, you know, back then, I would get an email every time you had a new subscriber. There was not many emails coming in every day. I could count them on two hands, you know? And I was like, first thing I did, well, one, the next day, I log into my email, and it's just whoosh all the way down. Just like, no, no, no, no, no, no, no, but that is such an unusual instinct. If I'm being honest, like, I don't think I would have done that. What the hell was going on there?

Patrick O'Shaughnessy: A wall.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: You didn't see it as a competition. What was happening?

Patrick O'Shaughnessy: The first thing that flashes through my head is, you know, in my show, I always ask people the same question at the end of, "What's the kindest thing anyone's ever done for you?" Some person on Twitter or something went and compiled every answer, there's 500 answers or whatever, and categorized them and, like, made a pie chart of what people say, and something like two-thirds of the answer to this question were the same, which was the kindest thing was some person made a bet on me, the person answering the question, before I deserved it.

Patrick O'Shaughnessy: Or, like, they saw something in me that maybe I didn't even see in myself. They bet on me before others would. And that was the answer to the kindest thing. And when I was 26, I became very interested in all of the... I studied philosophy early in life and I've always been interested in that stuff. But I became really interested in the religious texts, like all the world's religious texts. And I was in a weird spot in life.

Patrick O'Shaughnessy: I kind of hadn't found anything to do yet. I wasn't that good at anything and I was searching. I was always searching for, like, "What the hell should I do? What the hell is the point of all this?" And I found this passage in the Upanishads, which, as a book, is probably the most important book to me. And the Upanishads is this collection of stories from many of thousands of years ago that were passed down orally through generations and then eventually written down.

Patrick O'Shaughnessy: And I remember getting stuck on this one passage that literally felt like someone hit me in the face with a hammer. And there's a line in this passage that basically says something like, "Those who feed the hungry protect me. Those who don't are consumed by me." And it just felt like there was a moment of understanding that happened in my head.

Patrick O'Shaughnessy: But up until that point, from, you know, middle of teenage, I was this nice, sweet boy, and then I got kind of hardened and went through a period of life that was tough. And it woke me up that the whole point of this is to help other people. That's it. That's the entire point of this existence. And from that point forward, that's been my worldview. And so I think it's interesting, like, that's probably the thing that most informed my worldview.

Patrick O'Shaughnessy: And then the answer to this question that I love to ask is predominantly, "Someone bet on me." And like I told you before, the thing I love more than anything is, like, seeing the potential in somebody before everyone else and then helping the world see what I see.

Patrick O'Shaughnessy: Like, if I can do one thing over and over and over again the rest of my life, it would be audition people to see if there's something that I see that no one else sees and then help foster that and show everyone else what I think I see in a way that can be impactful in that person's life, which is what you described with our experience together.

David Senra: I think in the probably hundreds, I don't know, thousand conversations we've had, I don't think you've ever described it in such an easy-to-understand, impactful way like you just did, where it's just, like, the whole point of this whole thing is just to help other people.

Patrick O'Shaughnessy: You said before you were chasing something, right?

David Senra: Yeah.

Patrick O'Shaughnessy: I'm not chasing anything. I think it might be an interesting conversation today to talk about... Or, you know, how we view what we're doing in slightly different ways. But I have no goals. I'm not a goals person. I've written essays about not having goals. The most read thing I ever wrote, back when I used to do a lot of writing, was about... It was called The Growth Without Goals. And so, I'm not chasing any particular thing. I don't have a big, hairy, audacious goal or something like this.

Patrick O'Shaughnessy: I don't want to put someone on Mars like Elon might and to say that that's a bad thing. I think some people are goal-oriented and that's awesome. But that's not me. And I guess I've realized that if I have a goal in the abstract sense, it's just this thing over and over and over again. There's this amazing talk that I recommend everyone watch called Inventing on Principle. Have you seen this?

David Senra: Yeah.

Patrick O'Shaughnessy: It was a talk given by a computer scientist named Bret Victor and he espouses this idea that you should find a principle that you want to... His principle was digital creators should have instant feedback with their creation. So just like if you paint something with a paintbrush, you get instant feedback. You see the paint immediately. Whereas in computer science, you'd have to code over here and compile, and then you'd eventually see your result. There was this gap.

Patrick O'Shaughnessy: And so his principle was to collapse that gap. That was his life's mission. And I love that way of thinking about finding one's life's mission, is find a principle. Don't necessarily have a goal, but find a principle. And my principle is, like, when I see undiscovered talent, it is my obligation to do this thing, to get to know them, to learn from them, to start introducing them to people, to start... I don't need to get anything out of it. Like, what I get out of it is the thing. That's the point.

David Senra: But you're one of the few people in the world that have actually identified this organizing principle and then built a wonderful business around that. And I could see, like... We've talked about this a million times, but the media and investing are not two separate things. If you actually know Patrick and what is important to him, like, they are the exact same thing.

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: It's taken me a long time to articulate that principle. A decade. And that's okay. Like, don't get discouraged if you don't watch Bret Victor's talk and can't name your principle an hour later. Like, it takes time. But, you know you've found your principle when it starts informing literally every decision you make every day with your time. And that's what it does for me and it becomes universal.

Patrick O'Shaughnessy: Like, on my team, for example, we're 16 people, something like that. Now, this is how I think about my team. It's like, "Who can I find and see something in and bring them in and then make their career explode, hopefully, in an amazing way?" And so it can be investing, it can be just in friendship, it can be on your team. Like, a good principle can be applied everywhere.

Patrick O'Shaughnessy: And that's why I think this idea is so powerful to do the work to find your principle for invention. And I have no idea where it will take us. That's the other fun part, is one of the reasons I don't like goals is I think very talented people, when they set a goal, they tend to do it. And that's why goals are interesting to lots of people, it's a great way to make progress.

Patrick O'Shaughnessy: But I find it unexciting because the second you set some big goal, you kind of know what's going to happen because you go do it and you know the road in front of you, and you have blinders on. And I don't actually like having blinders on. I like to go-- Everything that's ever worked for me has come out of the periphery. You know, Sam Hinkie, vroom, texts me about you. Like, I wasn't looking for a podcaster to promote.

David Senra: Mm-hmm.

David Senra: Yeah.

David Senra: Yeah.

David Senra: Yeah.

Patrick O'Shaughnessy: You were not the result of some goal that I was seeking. You were just something that, like, came out of left field. And everything interesting I've ever done came out of left field, and it's which is why I don't keep long-term goals or short-term goals, is that opportunity just... I'm very open to opportunity along this principle, and so I'm very enamored of this idea for how to live.

David Senra: Having Patrick as one of the first guests on my new show was very important to me because of the role that he has played in my life and the quality of the product that he puts out. His podcast, "Invest Like The Best," has taught me so much and has made my life better in the more than seven years that I've been listening to it. Patrick and I both have a deep, multi-year partnership with the presenting sponsor of this podcast, Ramp, and I think there's a lesson in there that is applicable to anyone who is trying to make something great in the world.

David Senra: The founders of Ramp know, just like Steve Jobs knew, that you always bet on talent. The founders of Ramp wanted to be associated with the podcasts that they listened to, enjoyed, and benefited from. They wanted to bet on talent in everything that their company does. To Steve Jobs, this was mandatory. Steve once said, "You must find the extraordinary people. A small group of A-players can run circles around a giant team of B and C players." And so you must build a team that pursues the A-players. And this is exactly what Ramp has done.

David Senra: Ramp has the most talented technical team in their industry. Becoming an engineer at Ramp is nearly impossible. In the last year, Ramp has hired only .23% of the people that applied. This means when your company uses Ramp, you now have top-tier technical talent and some of the best AI engineers in the world working on your behalf 24/7 to automate and improve all of your business's financial operations. And they do this on a single platform.

David Senra: Ramp gives your business fully programmable corporate credit cards for your entire team, automated expense reporting, bill payments, accounting, and more, all in one place. The longer you use Ramp, the more efficient your company becomes. This is important because, as Sam Walton said in his autobiography, "You can make a lot of different mistakes and still recover if you run an efficient operation, or you can be brilliant and still go out of business if you're too inefficient." Ramp helps you run an efficient organization. I run my business on Ramp and so do most of the other top founders and CEOs that I know.

David Senra: I hear from people all the time that listen to this podcast that have switched to Ramp and rave about the quality of the product. In fact, Matt Paulson, the founder of Marketbeat just sent me a message. He said that Ramp helped him save $420,000 in monthly expenses. Make sure you go to ramp.com today to learn how they can help your business save both time and money. That is ramp.com.

David Senra: At what age did you stop having goals?

Patrick O'Shaughnessy: Well, this essay that I wrote, I'm 40 now. I wrote when I was 28 because I wrote it on the train. I used to commute back and forth from New York City to Stamford, Connecticut. And I was about to have my first child, my son Pierce.

Patrick O'Shaughnessy: And my dad, when I was 21, handed me this book of letters that he had been writing to me since I was born, and a lot of them were when I was like a baby, like the... And I've done the same thing for my son, and it's the same pattern. There's tons of letters in the first couple of years, and then it gets more spaced out, and now I do one on his birthday every year and things like this.

David Senra: Mm-hmm.

Patrick O'Shaughnessy: And I'm going to give him a packet of letters as well when he turns 21. And I remember starting this process of wanting to write him a letter before he was born. And it got me wondering about, like, "What is good parenting? Like, what do I want to do as a dad?" And I believe deeply in showing, not telling. Like, I think maybe that's another reason I don't like being interviewed. I don't like telling, I'd rather just set an example.

Patrick O'Shaughnessy: But, I was thinking, "What example do I want to show Pierce?" And then I don't remember my exact chain of thinking, but it ended up in this idea of everything I just talked about. So it was born of wondering, like, "What example do I want my son to see and emulate?" Because I'm sure you've learned this about kids as well, they don't do what you tell them. They do what you do. They just copy you.

Patrick O'Shaughnessy: And so how you behave is how you parent, and I was thinking about that at age 28 and wrote this thing. And so that's where it came from. So right around then is probably the first time I thought about it.

David Senra: And then how long from 28 till you realized this is going to be the simple organizing principle of how I'm going to live my life and spend my time?

Patrick O'Shaughnessy: I actually don't think I could have articulated the principle as I just laid it out until very recently. So I could have told you about the power of Bret Victor's Inventing on Principle starting 10 years ago or whenever I first saw it, but I would not have been able to articulate the principle to you cleanly and that's because it's hard. It's hard to pin for whatever reason, it's really hard to pin this down. Interestingly, I've never met Bret Victor.

Patrick O'Shaughnessy: If he's listening, I'd love to meet him. I owe him an enormous debt of gratitude for one of my bigger career successes, which was... I took his principle, not my own, but his principle of instant feedback and applied it as the primary design principle to software that I built in my last business, which worked really well.

Patrick O'Shaughnessy: The software itself worked really well and the business grew a lot because of the software, and the software worked well because of his principle of instant feedback on choices being made by the user showing up in this case in a visual that described their portfolio. And so I actually, before I had my own principle, stole his principle to great effect, which just goes to show the power of a great principle. But I couldn't have articulated it for a really long time and I can't explain to you why that's the case. I don't know.

David Senra: There's a great line from Alan Watts that I always think about. He's like, "People think that life is meant to be understood," and it's like, no, "Life is meant to be experienced."

Patrick O'Shaughnessy: Mm.

David Senra: And I find that in my own self. Like, I do think I can't explain. I have a lot of really foo-foo part of... I know I always just say that line and you laugh, but I have this really foo-foo part of it where I just go off feeling. An intuition for a lot of things that I do, and I don't want to have to describe why I believe this to be true or why I want to pursue this path or why I think this idea is interesting. I think it's just something inside of me that language cannot describe.

Patrick O'Shaughnessy: I don't know if it was Alan Watts that said this. He had such a way with words that maybe it was him. It might've been Joseph Campbell. But something to the effect of, we're not searching for the meaning of life but for the feeling of being alive. And I think that's correct. And I think a great... If you play red light, green light with principle, as you search for your principle, I think you could do a lot worse than knowing you're on the right path if the thing makes you feel more alive.

Patrick O'Shaughnessy: Like, if you go in the direction, and people know what it's like to feel alive. They can call to mind these moments in their lives where they felt the most present and alive. And using those as a signpost to what your principle might be or what you should be doing, I think, is a really great thing. And that's certainly how I remember reading that line 15 years ago as well, and then starting to chase the feeling of being alive. Not a goal, but just that feeling. And everyone can answer this question, by the way.

Patrick O'Shaughnessy: It's a great way to have a conversation with someone to kind of ask them where they feel this and then also why they're not doing more of whatever the answer happens to be. Which is a funny circumstance of humans that they kind of know what makes them feel most alive and then they don't do it most of their lives.

David Senra: That's a very interesting question. What's your guess on why they don't?

Patrick O'Shaughnessy: Usually it's simple, which is fear. It's fear that by pursuing an original path... I have this idea that the best story always wins, and I actually spent the last couple of months really trying to figure out what do I think "best story" means. And the best principles for a great story that I could come up with were originality, hardship, and transformation.

Patrick O'Shaughnessy: And if you dig into originality, that one is really interesting to me because people don't pursue original paths usually because they're fearful of the unknown, because an original path, by definition, means it's all going to be on you, and that's uncomfortable and hard and because an original path usually means leaving a very comfortable current existence in a way that's scary.

Patrick O'Shaughnessy: And so I think when you really drill people on why not, they'll give reasons that add up to, "I'm afraid," and that's hard to get over.

David Senra: You've said to me before that you used to be a masochist for introspection.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: First of all, when did that stop? And then do you think that helped you find this organizing principle for your life?

Patrick O'Shaughnessy: It definitely helped me find it because I wanted to not waste life. When I was a little kid, young, five years old or whatever, I had this just crippling fear of death. Like, I remember my mom and dad would have to sit and hold my hand for me to fall asleep at night because... And the reason was I would just sit there spiraling on this crazy idea, maybe this is why I studied philosophy, that someday I would not exist, and that just freaked me out and did for decades.

Patrick O'Shaughnessy: So that probably kicked off this introspective period of my life where I was very curious about philosophical traditions and religious traditions and metaphysics and all this kind of stuff because I wanted to know, what the hell is the point of all this? Like, what's the point?

Patrick O'Shaughnessy: What's the meaning? What's the purpose? And otherwise, it's just terrifying, right? That we're here for a blip and then gone.

David Senra: Yeah.

Patrick O'Shaughnessy: It's just terrifying. I try not to sit down and think about it too much. In fact, I'd like to move on. But that kicked off this period of, yeah, I wanted to understand myself and others, and so I was very introspective, and of course, that made me want to not live a dull life, and I was very scared of just living this train track existence. So yeah. It did help a lot. But interestingly, once I have clicked into, I think, understanding what I want to do, I don't think about it at all.

Patrick O'Shaughnessy: And now, I have very little introspection left in my life. I used to be so obsessed with all of these personality tests and what they mean and psychology and seeking and, like, all the modern methods for doing that, and I've kind of just lost, not total interest, but I've lost a lot of my interest in that.

David Senra: You solved the problem that you were using it, introspection was the tool and then, like, you don't need to use the tool once the job is done.

Patrick O'Shaughnessy: Yeah, maybe.

Patrick O'Shaughnessy: Yeah, maybe.

Patrick O'Shaughnessy: Yeah, maybe. Maybe that's right.

David Senra: You mentioned earlier that we have different approaches and that you wanted to talk about that. What do you think... Like, I'm always curious. Again, some of this stuff I should not say on a podcast, but I'm always curious. People that know me well, like, what is their interpretation of their view of me that is different than my own? So, like, what do you think my organizing principle is?

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: Your organizing principle.

David Senra: If yours is just helping as many people as possible and this is what life's about and then you have all these resources to do so through media and capital and relationships.

Patrick O'Shaughnessy: Just to clarify, it's not helping as many people as possible. It is trying to see enormous, like, not yet realized potential.

David Senra: Okay.

Patrick O'Shaughnessy: And my principle is that, when I do, it is my obligation with nothing... And maybe I end up benefiting, but that's not the point. That it's my obligation to tell people about it and to help foster it into existence. So, you know, important difference. Well, it took me a decade to state my organizing principle, I'm not going to be able to name yours in a minute.

Patrick O'Shaughnessy: But you're probably the most single-minded and devoted to what they do person that I know, in the sense that most people that have achieved a level of success in their field or in their job that you have begin to branch... The world, when that happens, pulls you into this branching exercise where you end up doing a lots of different stuff.

Patrick O'Shaughnessy: And that, you end up monetizing in different ways, or going into different lines of business, or changing how you do things, expanding. The single-mindedness that you have is quite distinct from the people that I know. And why are you doing it? I think you've talked about this certainly in private with me, but also in public about, we came from opposite circumstances.

Patrick O'Shaughnessy: Like, I was born on proverbial third base, or sliding into home. I come from a history of extremely successful entrepreneurs. My great-grandfather, who had the best name ever, his name was Ignatius Aloysius O'Shaughnessy. Everyone called him IA. He was, I think, the 13th of 13 kids. He was one of the richest men in the United States.

Patrick O'Shaughnessy: He was an oil wildcatter first oil hole he ever drilled, I think, still pumps oil to this day in the Midwest. And so he was a giant. He was broken up in the antitrust in the Rockefeller antitrust stuff around Standard Oil. And our family takes great inspiration from him because he made this fortune, he did not give a shit about money. He didn't really spend it, he gave away basically all of it in his lifetime, mostly anonymously.

Patrick O'Shaughnessy: My dad tells this story about being at his funeral when my dad was 11, and all these people were there, and no one knew who they were, and my dad would go up to one and be like, "Who are you?" And they would say, "Well, Mr. IA, I cut his hair, and he put my kids through college and bought me a house," or, "Mr. IA did this, or this, or this." And we didn't even know where it went. And I have benefited from this tremendous history of business success in and around my family forever.

Patrick O'Shaughnessy: Whereas you came from a very different set of circumstances. Our friend Sam has this idea of there's founders of businesses and there's founders of families, and I think of you as the founder of your family, and I think that's incredibly powerful, and I think it's your greatest accomplishment that things repeat through the generations.

Patrick O'Shaughnessy: You're fond of saying, "The story of the father and the son are the same." And it takes tremendous character, willpower, talent, lots of stuff to break from that family tradition and go a new direction, which you've done, which I just think is remarkable.

Patrick O'Shaughnessy: And I don't know if that's the underlying why that you refused to let your family continue to go the same direction that it had gone up until you were born, and you went, as Sam would say and we've talked about, you went searching for mentors because you didn't have them in your life, you found them in books and in founders, and you've been telling everybody about it ever since, and it worked for you to change your life and now we know, based on your work, that your work is now changing other people's lives in that same way that you changed your own first, but you were the first beneficiary of it. And so what is your principle or why?

Patrick O'Shaughnessy: I don't know, maybe it's that you can... You don't have to just keep going the same direction that you were given, you can break off and found something new. I think that's pretty amazing.

David Senra: I think there's a lot of times... I really resonate with what you said when you were, you found that book and you're like, "This paragraph, this sentence just hits you with, like, a hammer to the face."

Patrick O'Shaughnessy: Mm-hmm.

David Senra: This is also like I use podcasts for this reading mainly it's like, I think people are rushing through things too fast. You know, I'm famous for only listening to podcasts on 1x. Everybody's like, "Oh, you read a lot, you must read fast." I'm like, "Yeah, 25 pages an hour is fast." Like, I'm not speed reading here. I think I want understanding, and I want understanding of how things actually are, not how humans say they are.

David Senra: And humans, not only are we lying to ourselves constantly, which if you're lying to yourself, of course you're lying to other people about why you're doing what you're doing or what it is that you're doing. And this is why I like autobiographies and biography so much, because in many cases the person's like long past dead or they're older and they're just like, "I'm writing this book when I'm 80. I'm not incentivized to lie, and here's the stuff I went through."

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And the trouble with whatever, being what kind of dad you are, trouble with women, trouble with business, which you realize there's nothing that you're experiencing that somebody else hasn't already experienced. And so what I want is true understanding of humanity as it is, human nature as it is, and the world that we're creating, and then I use their stories. It's not really about them, it's about you. And I think this...

David Senra: I don't think this has nothing to do with me, I think when you watch a great movie or you hear a great story, you hear a great song, you're not thinking about, like, "Oh, this happened to Taylor Swift." You're like, "Oh, I had that same experience in this relationship." Or, "I went through this exact same thing." And it's like a form of understanding, I'm in the middle of this right now.

David Senra: We were just having lunch upstairs and essentially I'm just in the middle of trying to find the story that I want to tell with this book that grabbed ahold of me for six months. And I told you about... This is Bruce Springsteen's autobiography. I don't even listen to his music. And I told you about this, right? Like, right when-- I was like, there is stuff in this book that this dude looks like he crawled inside of my mind.

Patrick O'Shaughnessy: Hm.

David Senra: And, like, especially in regards to how he views his work and the impact that it has on... It's like, that is not a sentence, that is not a paragraph, that is, like...That was made for me to read at this point.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And it's insanely powerful, and to the point where, like, it's like a drug. You know, I told you, like, right away, when you... Again, I need to give you credit. We'll go back to this drug and understanding because I think this is really important about people understanding why I want to talk to certain people and why I was freaking adamant and kind of pushing you on this, and we rescheduled a few times. I wouldn't be doing this if it wasn't for you, not only because of the platform that you gave founders, right? The podcast. Then that crazy episode that we did together, which I think is like, we're never... Like, that was like lightning in a bottle.

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: It was, yeah.

David Senra: It's "Invest Like The Best." The title is Passion & Pain, and people were always like, "Oh, like, did you guys sketch this out?" I was like, "No, Patrick doesn't sketch things out like that." He's like, "we built a friendship. I want you on the show." Like, I don't think you told me anything we were going to talk about. I do remember you texting me a few hours. We were supposed to do it at 10:00 AM. You're like, "Hey, I got pushback. Can we do 1:00 PM?" I'm like, "Oh no, my brain only works in the morning." So I took, like, a quick power nap, and then I'm in this booth.

David Senra: We didn't do video, but you can see me, and I'm in, like, this phone booth that I put in my house that... I was the only person... These phone booths are in all these offices, and I had one... They came and delivered to my house, and they're like, "You know, we've never delivered to somebody's house before." I was like, "This isn't a phone booth. This is a podcast studio. This makes perfect sense to me."

Patrick O'Shaughnessy: Yeah.

David Senra: And then we just had that conversation and that was a huge inflection point. Like, that weekend that happened after that was, like, one of the craziest weekends of my entire life. But then you pushed me for years. You were like, "You should be recording conversations. You should be recording these conversations. What are you doing?" And I was like, "No, no, it's a distraction.

David Senra: I don't want to do it, I won't do it." And then, you know, I've told this story a bunch, but I think, like, it's really important, where I would not be doing what I'm doing right now at this very moment if we didn't have... Me and you had this dinner with Daniel Ek in New York. It lasted four hours. I know you don't like when I tell you how long I talk to people.

Patrick O'Shaughnessy: This is one of David's quirks. He tells you how long he talked to someone every time.

David Senra: Because I'm not in-

Patrick O'Shaughnessy: You just had this four-hour lunch, so it's-

David Senra: Yeah, because I'm not interested in superficial at all. I can't tell you who it was. I just had dinner.

Patrick O'Shaughnessy: How long was it?

David Senra: I'm going to tell you right now. But it was an incredible dinner the first time we met, and it was unexpected, requested by them, and three hours into this, this person's like, "I have told you things no one else knows about me." The very first time I met them. So it's just, I have no interest in the superficial, and I think you have to talk for a long time because it takes a little while to get warmed up and feel the person out.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And this is why what you said earlier is so important, like, fewer deep relationships. Dude, think about the crazy conversation, which we're not going to relive, but, like, me and you just had an insane two-and-a-half-hour conversation in Tel Aviv at 2:00 in the morning. And to have that level of honesty in conversation, you would have to have years of getting to know somebody. So, I do think...

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: I also think you're providing people with a sort of set of ingredients, maybe, through these episodes and conversations, but that it's important that people then go make their own recipe. You shouldn't just want to live like person XYZ. A lot of people you cover have the same pitfalls in their lives, and one might be tempted to think those pitfalls are just inevitable byproducts of success, but I hate that kind of thinking. I think, screw base rates. I never care what the base rate is.

Patrick O'Shaughnessy: The most interesting stuff is outliers by definition. So, I don't care what happened to everybody else. I don't care if there's common pitfalls. I think it's important that people make their own recipe from the ingredients that you've offered them from all these amazing and interesting lives that you've studied. And you're just doing that for yourself. Like, that's been the search.

David Senra: I think it is for myself. You are interested in other people and, frankly, in a way that I am not. And I've seen, it's very real, and it happens every time we're with other people together. I'm like, "Oh, he actually wants to know," whereas I am on this search of like, "How the hell do I not have a terrible life?" This is why I think the skillset that gets you to where you are, like, so many people plateau, and I'm not interested in plateauing. I'm not interested in mailing it in. I'm interested in... I want to get to an end in my life. I don't want to tap dance on a giant reservoir of potential. I want, like, there was nothing more that I could've possibly done with my skillset and everything else. I want to figure out how to get the most out of that.

Patrick O'Shaughnessy: Mm.

Patrick O'Shaughnessy: Mm.

David Senra: And there's something you just said about, like, there's a line in this Bruce Springsteen autobiography where he's like, "People don't come to rock shows," or to concerts, rather, "to learn." They come to remind them, for you to remind them of stuff they already know is true." And I think, yeah, you're going to learn, like, there's obviously creative ideas on how to build a company in a 400-page biography of somebody. But what you're going to realize is just that there's a lot of stuff that you already know and you know is true and either you haven't applied it, or you forgot it, or you did it for a little bit and you need a reminder. This is why me and you always describe Founders. Like, it's church. It's church for entrepreneurs.

Patrick O'Shaughnessy: Mm.

Patrick O'Shaughnessy: Mm.

Patrick O'Shaughnessy: Well, in that church, I think the animating interesting question is you read these stories, all of which back to my idea of originality, hardship, transformation, you know, best story wins, that originality is you're inspiring people to wonder, "What's my thing?" Everyone's got something. I guarantee it. It's my favorite thing to search for in conversation, especially if someone's not yet doing it, which is kind of the same, the same search for unrealized potential or something.

Patrick O'Shaughnessy: Everyone has a thing that, for whatever set of reasons, their life experiences, how they're wired, their naturally endowed gifts, and searching for that thing is really interesting and really hard. And I think that's what Founders continues to do for me, is show me examples of people that went to the trouble to find their thing and then, once they found it, foster it the rest of their life. And again, once you find your thing, the second thing is hardship. It's not supposed to be easy. Nothing meaningful is easy, and that's fine.

Patrick O'Shaughnessy: And then once you learn that, I think that's when it gets really fun is that I always have this feeling that the second something just feels easy, and I'm kind of going through the motions, I get really uncomfortable and want to try to push myself in in some new way. But I think that's what Founders does so well, is it shows... It's what, back to the very beginning of our relationship and why I sent that tweet out and why we talked to each other for an hour the first time we talked. It's because it was so unique, and so different, and inspiring. So, I think it's a powerful thing to do for people.

David Senra: I think when I say, "What is my organizing principle?" It's like I want to understand things, or I want to understand about things. I want to understand people, and to understand people, you have to go deep and, like, where were you born? What was going on? What was this experience like? You have to just spend a lot of time asking them questions and having these long, deep conversations. And I don't think... I mean, there's a handful of people that I feel I truly know. It takes a long time. It takes at least 100 hours of conversation on the low end.

Patrick O'Shaughnessy: Mm.

Patrick O'Shaughnessy: You mentioned, you said, "organizing principle," which I think that's correct. Just to push, because this can now be something we talk about for the next couple of years, which is probably how long it'll take to articulate. That's different than, "What is your principle for invention?" So back to the idea of inventing on principle. The principle should be something that when you see it violated, it is your obligation to go correct it, and that that correction is an act of service for other people, not for yourself. It's not about you.

David Senra: Yeah.

Patrick O'Shaughnessy: And that's what makes the idea so powerful. I agree that that's your organizing principle. That's the thing behind why you're doing what you're doing. It will be fun to try to pin down what the principle is for invention because that's what you're doing. You're making new things, which is the most fun and rewarding experience of a lifetime.

Patrick O'Shaughnessy: And I remember the opening quote in this compilation of his life's writing by Joseph Campbell that was done by his niece or something. The little opening quote in the book is, "The privilege of a lifetime is being who you are," and the people that make things that are the most interesting, those things are a reflection of themselves. That's the most sustainable form of creation. If you can sort of spill yourself onto the thing you're making, which benefits others, the thing being of service to other people in some way, I think that's the thing that we're... Actually, I think that's what we're all after.

Patrick O'Shaughnessy: I think what we all want is to participate in the act of creation in a small way that reflects the act of creation going on at a grand scale, and to have that experience of, in so doing, by pouring oneself out into the thing, and then having the thing be of service to others, that's an amazing feeling. And it's hard to get going, but once you do, I don't know anybody, I've never met anybody had that experience and gone back. Not one. And it's because I think it's the thing that we're all after, and that's what you're doing too with this show.

David Senra: I think one of the biggest things I want to avoid is finding the thing, doing the thing, being great at the thing, and then something you do causes that to stop, where, like, I'm kind of obsessed with the sustained success. I don't want to have this huge spike. I don't want to flame out. I'd rather just do the slow build decade after decade, get better, and keep doing it. This is why essentially I read fiction and I read biography.

David Senra: That's basically what I read, and the biography part is just like, "Okay. What happens after they got what they wanted?" And the conversations I've been having, a lot of these I've been having on camera, but after, off camera, I'm always asking because most of these people are older and more experienced and obviously more successful, smarter, and everything else, just like, "What do I have to worry about? What am I not seeing that could cause me to stop? I like what I'm doing. I love it. What am I doing that would cause it to, for me to not be able to do that?" And there's interesting human questions about this.

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: Well, the trap is, before you do the work to figure out the thing that makes you feel alive, there's this great line in the Upanishads that it's always referred to as abiding joy, joy that doesn't run out. You don't use it up, like you use up so many resources. As you use it, you get more of it. That's abiding joy. The target for most people becomes the traditional money, power, fame, because those are worldly proxies for success that we all recognize and are, for sure, to some degree, true. It's hard to get a lot of those three things without being successful in some way.

Patrick O'Shaughnessy: I think those things are huge traps because once you start to get one, it's the thing you start chasing, and it's different than chasing the feeling of being alive, that abiding joy of feeling alive that we talked about earlier, which you'll never run out of. That will always guide you well, always, and money, power, fame will not. And so I think the answer to your question, or your worry, is just that make sure you're chasing the feeling of being alive and that the intuition around that, and you'll be fine. And it's when we get sucked... And I've, of course, just like everybody else, I've been intoxicated by those three things at various points in my life, and that's because they're intoxicating. It feels really good the first time you have a lot of one of those things.

David Senra: Yeah.

David Senra: You're over fame though. You don't like it.

Patrick O'Shaughnessy: Yeah, I don't. I wish I could do what I do, and you know that thing in "Men In Black," where they flash you in the face. I wish at the end of each of my episodes, to flash people in the face, and they forgot who I was and didn't recognize me.

David Senra: I've been thinking about this lately. It's like, what I actually... You have limited time that like, every day, where do I spend this? And it's like three things, health, work, relationships, and I can't think of anything else that I care deeply about. Health has to come first because if we are sick or we have no energy, we can't do anything else. But other than that, if you look at how I spend my time, it's essentially just like, I'm building, I'm creating work that I hope it makes somebody else's life better, that I truly am, like the abiding joy, like chasing that, and then I'm just deeply interested in a shocking way of having really strong relationships with other people. And I was not like that 10 years ago.

Patrick O'Shaughnessy: Mmm.

Patrick O'Shaughnessy: My experience actually, I would disagree with the order. I had tremendously bad health problems for a long time, and I don't anymore, thankfully. But I'm convinced, I'm certain that the reason is that I finally got my work and my relationships correct, and that when you're doing something you love and have great core relationships, all of a sudden, magically, your health gets way better.

Patrick O'Shaughnessy: And during that time when I had lots of health problems, I ate unbelievably well. I worked out every day. I did everything you're supposed to do and then some. I was crazy about it. I kept daily logs of all this stuff. There's nothing I didn't try. There's no willy-foofoo thing that I didn't explore. I tried everything to solve some of these problems, and I couldn't solve them. And at one point, I felt resigned to just like, "I guess I'm just one of those people that's going to be sick in life. That's just how it's going to be for me."

Patrick O'Shaughnessy: And it cannot be a coincidence that when I finally started doing the thing that I think I was meant to do with my life, and spend all my time with the people and focused on the relationships, that all of a sudden, my health got better. So now, of course, I still invest a lot in my health. I'm not arguing with the three key things, but I found that an interesting experience in life. The body keeps the score.

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David Senra: The fame part is interesting because this is something that you uniquely understand and I can talk to you about. It's not being known for the sake of being known, like these reality TV show people, that's weird. I want my work to be so good that it can't help but become known and talked about and spread because they find value in it. This is just human nature. If you find value in a song, a movie, a book, or a podcast, no one keeps that to themselves. A restaurant.

David Senra: We're compelled to tell other people about the things that we like. What I would say is the reason I think I view it differently than you, and you can tell me if I'm wrong or whatever, it's just like, and not even wrong, but it's the relationships that you get to build as a result of you being easy to understand to other people. So, no one's going to stumble upon any of my work and be like, "What is this guy actually interested in?"

David Senra: It's like very... Yeah, it's quite clear, very obvious, and then if you think there's some kind of unique insight, but my point being is just, I think this comes down to a principle of why are all the people that I've studied, either had a conversation with, or read about, why are they great at what they do? And it has to do with, I do think, the most fundamentally important thing that you do in life is choose who's around you.

Patrick O'Shaughnessy: Quite clear.

Patrick O'Shaughnessy: Of course.

David Senra: Your friends, people you work for. Your company is the people that you are able to recruit and to build. And so, what I couldn't understand is, I was not interested at all in relationships with other people, I would say 10 years ago, somewhere around there, where now it's like I invest a ton in that element. I think it's the part that I'm very excited about my work, that has never diminished, but I think it's the part that I'm most excited about and have been for quite a while.

Patrick O'Shaughnessy: Well, because of course, on your deathbed, that's what you're going to be thinking about, not your 5,000 podcasts. You're not going to lie there and think-

David Senra: But that's surprising to me, Patrick. This is why I get... This f***** Bruce Springsteen book can't... It's like messing with me so much. It's because I'm seeing this, he's 70, he's 66, when he writes it, 67, something like that, and now he's 76 and I heard him on another interview talking about it. Where the first half of the book is like, this guy has one of the most insane work ethics that you've ever seen. And it's channeled into one thing and he has no doubts since he was 15 that this is what he's going to do.

David Senra: And he realizes that he does not have the skill set, or he has all these things that he has not developed the skill set to handle. I'm just going to try to explain this. Let me just record a whole podcast about it so maybe this'll hopefully make sense. It was surprising to me that this man, who is psychopathically obsessed with professional achievement, and fame, and stardom, and all the stuff that he was very upfront about what he wanted from a young age, okay? He gets it, which I'll get to in a minute. And his final realization is, life is more important. Work is a part of life, it is not my full life. Life is life.

David Senra: It is important. And his biggest struggle was, he becomes famous as I... This is what Jimmy Iovine told me because I got to meet him, and right when I was leaving his house, he's like, "You need to go watch the new Bruce Springsteen movie." And it's called "Deliver Me from Nowhere." And I thought it was going to be like a biography of his life. That's not what it's about at all. It is like a dark... I was shocked. Dark movie. This is the key to understanding. Unbelievable, like, terrible environment born into. There's going to be two actions there.

David Senra: You're just like, "This is what life is, I'm going to accept it," or you're going to have this like maniacal will to change things. He has the maniacal will. And he's like, "I don't want to live like that." His dad was one of the worst human beings to him. He takes all that pain, channels it into a work ethic that is, gets him exactly what he wanted. Gets what he wants, which is now everybody knows who he is, he's worldwide famous, he's rich, everything.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And then immediately drops in his mid-30s into the deepest depression of his life. And what he realizes is, "That's not what I actually wanted." And this is what it goes by. I think I told you this upstairs, or maybe we mentioned this. It's like, we had a very interesting conversation at dinner last night, and it started with, "What is the lie that you're telling yourself?" And me and another person going around that for quite a while.

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And it was very fascinating. And the lie that Bruce was telling himself was that work was the most important, that becoming a rock star was the most important, fame was the most important. And what he realizes that his parents had so messed up his emotional well-being, he was incapable of doing the thing that he wanted. In his case, he wanted, desperately wanted, to have kids, to be married, to break the chain, like we mentioned earlier, of like, "My kids will not experience what he experienced."

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And he was even writing... He has a whole album fantasizing about this before he's able to do it. And he would run into the same thing where it's going to be such a crazy juxtaposition of, like, he's on stage in front of 40,000 people, they all love him. And yet, in his case, he talks a lot about women in the book. He would get close to a woman, he'd have some kind of feelings for her, she'd have feelings for him back, okay? Then he immediately goes, "Why do you love me?"

David Senra: Like, "I am so f***** up and undeserving, so the fact that you love me means there's something wrong with you, and I'm going to hurt you because you love me." And then he'd run away, and then he'd get into another relationship, and it'd go over and over and over again. And he didn't realize the source of his depression was he didn't know what he actually wanted, and he didn't have the skill set.

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: Mmm.

David Senra: And then he winds up meeting the woman, he's married, by the way, he winds up meeting another woman who was in his band and getting divorced because he realizes, like, this is the person that can... I'm willing to do the work necessary to fix, which is a crazy thing. And then he goes through 25 years of therapy, and in some cases, he has to get on antidepressants and he's unbelievably honest from what took place in his life from 35 until 67 when he's writing his book.

David Senra: And so, I think there's all kinds of lessons in there from personal, like, what do you actually want in your personal life? The kind of relationships you want, with friends, romantic partners, whatever the case is. But this is what I meant about, I want to make sure I develop the skill set not just to stay where I am, and you've pushed me in this direction a million times. You're like, "Stop doing everything yourself."

David Senra: We have a million conversations where you're just, like, "Why don't you have a team? Why don't you do all this?" It's like, it makes sense why I don't have a team, because I don't f**** trust anybody. That's obvious why that is. And I do think I'm getting better and better and better, even with the stuff me and you talk about, like, 10 years ago, there's a zero chance I would've let that come out of my mouth. Zero.

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: Mm.

Patrick O'Shaughnessy: I mean, you tell Bruce's story, but I think you're talking about yourself to a large degree.

David Senra: I know.

Patrick O'Shaughnessy: And maybe my arrival at the aspiration, I'm by no means perfect, to be more service-oriented. My grandmother who just passed away, she was 99, banged on me. Every time she'd see me, this would be the topic of conversation. She's like, "Yeah, yeah, yeah, congratulations on all the success." Who gives a shit? "What are you doing for other people? That's what I want to know." And I'm convinced that's the way out. That I think, like you, and so many listening have their set of demons that they've struggled with, and the path out is others. Simple as that. And it sounds like Bruce, I don't know Bruce, I'm not a huge Springsteen fan, I'd love to... I need to read the book obviously, but that seems like a tale as old as time.

David Senra: But this is something I learned from you, this idea of making sure that your source of fuel and energy and ambition is generative and not negative. And I do think the conversation I've had with you, with Sam Hinkie, it's really important. It's like I'm getting to the point where I push myself because I love it. I'm way nicer to myself than I have ever been because I'm like, "Oh, this doesn't serve me anymore." I'm not going like, I will be successful because I love it, and if I love it, I'll do it all the time, and if I do it all the time, I'll get really good at it. And if I get really good at it, money will come as a result because it's an act of service, right?

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: Yeah. The clean fuel/dirty fuel debate is really interesting. And look, a lot of most, or nearly all of the books that you've read were people that were fueled by dirty fuel. Dirty fuel works really well, but it consumes the person in a way that I would far rather die, you know, nobody knowing who I am with no worldly success, but having people that could count on me, rely on me, I was faithful to, that I was loyal to. That's what I want at the end. So, if you can work backwards from that, that's another cool way to think about it, working backwards from what you hope is true is a simple heuristic for finding what to do well. And yeah, I think I can't wait to read the book.

David Senra: This is why I think reading a bunch at the same time or not the same time, but having a lot to pull from, is like, I'm reading the Bruce Springsteen book, but then you realize another person with like superhero work ethic and drive and ambition was the LBJ, which Robert Caro brilliantly writes about. And you realize Bruce is generative. It took him a while to figure it out, but he got on the other side of that, where LBJ never did. And even though their source is very similar, there's a great story that Robert Caro tells in one of his books where LBJ finally gets to Washington. I think he's an intern. I don't even remember what job he has. He has no money, it's cold, and it'd be like the sun would be coming up at 5:30, and this woman that worked with him would always see him running everywhere.

Patrick O'Shaughnessy: Mm.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And they just assumed, "Oh, he's got no coat, he got no money. He's running to warm himself up." And then the summer comes, and he's still running. And obviously Robert Caro's a master with words and storytelling, and his whole point is, of course he was running. He finally made it to the spot because he was talking about he wanted to be president since he was in third grade or something. He's like, he finally made it to the city, to the spot of where all his dreams are, and he was going to run after his dreams. There's so much in between these two stories.

David Senra: One guy's a rock star, one guy becomes the President of the United States, and it's the same thing. One is generative, one is unbelievably manipulative and probably not a guy that you'd want in your life to be around. And so I think also learning from great examples, but almost seeing, like, "Oh, I don't want to be that way." This is something that one of the best things about our friendship is, I actually want to let people in. I want to have friends, and deep friends. And in the past, that wasn't an important thing to me.

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: Mmm.

Patrick O'Shaughnessy: Of course.

Patrick O'Shaughnessy: Mm-hmm. Agreed.

David Senra: This conversation is now therapy for David. But this is what I... This is my point was, when I wanted to sit down with you, there's a bunch of things I want to talk about, but it's just like, I also want to kind of talk about the stuff that we normally talk about. The reason I think it's important for me and you too is how much of our ideas actually came from the creation of the podcast. You think about all the different ideas, and topics, and things that you've learned as a byproduct of just making this thing. And then the unfair advantage that we have is essentially, we're professional learner. You get to study somebody, you get to have a multi-hour conversation with them, and like, "Oh wait, he said that," or, "She said this." Like, "I'm going to take that idea." Who have you grabbed ideas from, and who do you let influence the way you think?

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: I mean, how long have you got? I could easily rattle off 50 people.

David Senra: Let's take some of the most important ideas and where they came from.

Patrick O'Shaughnessy: To take the simplest example possible, in the early days of the show, this is a very practical real-world example. If you take the ideas that I got from Daniel, who you mentioned before at Spotify, about how to build software from Brett Victor, who I mentioned before about this principle for great software and what it looks like, and from a guy named Chetan Puttagunta at Benchmark, one of the partners at a very storied investing firm called Benchmark, who taught me how to sell software. Just those three guys, I basically just stole their ideas and applied it to my situation, and it worked to a spectacular degree. I didn't know anything about software. I had never built software before. I had an amazing team at the time that was able to pull it off.

Patrick O'Shaughnessy: But the direction of the resources and what to do strategically just came from asking those three or three of the greatest in the world at what they do, "How do I do this?" To somebody that could help me, and then not thinking too hard about what they tell me and just doing it and having it work. And so, there's a tiny example, three people and many more.

David Senra: Did you have all three on your podcast?

David Senra: You had two out of three.

Patrick O'Shaughnessy: I've never met Brett.

David Senra: Okay, so you have two out of three.

Patrick O'Shaughnessy: I've never met Brett. Yeah.

David Senra: These ideas came from conversations that you had on the podcast.

Patrick O'Shaughnessy: No, I didn't ask them this stuff on the podcast. But in time spent just offline with them, I'll never forget, I was in Benchmark's office in San Francisco showing Chetan the demo, I'd show him the demos. And, it was amazing. He'd give me feedback. They weren't an investor in my business or anything. He was just doing it out of just the goodness of his heart, I guess. And, same thing with the others, just... And there's many more than three people that contributed to that project that influenced me and taught me things. But yeah, mostly just offline asking questions, but I did interview Chetan several times and Daniel several times.

David Senra: This goes back to the beneficial nature of relationships. You start out as like, okay, I had a conversation with them, and then if there's some kind of mutual respect, you build a relationship. Right now we're filming, this is the first podcast ever filmed at the Aman in New York.

Patrick O'Shaughnessy: Yeah.

David Senra: You try to email the Aman in New York and ask them if they set up and film a podcast here for free, that's not going to happen. That happens because of the relationship, a personal relationship that I have with a friend of mine who is involved with Aman. This is why I always say relationships run the world, and our jobs are essentially like learning and then taking what we learned and packaging it for the consumption of somebody else, for an easy way for somebody else to consume and benefit from that learning, whether it's a conversation, a book review, or whatever the case is. So that's like very practical. That was in the early days when you were doing Canvas, right?

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: Mm.

Patrick O'Shaughnessy: Yeah.

David Senra: What about larger things in your life? Who do you think had an impact, like, my life would not be the same if not for that one conversation, that one idea with that person.

Patrick O'Shaughnessy: Two people came to mind right away. The first is Herb Allen from Allen & Company, who I don't know well. These lessons came from one incredibly interesting conversation about, I think, my sense of him. Again, don't know him well, is that he is uncompromising in his values. He's maybe the apex predator of the thing I want to do, which is like picking and supporting people. I think that's what he's done for a really long time with unbelievable success. And that he is so incredibly uncompromising about how he does that and willing, yeah, I won't tell the examples, but I think willing famously to throw away huge commercial opportunities just because the person wasn't who he wanted to support.

David Senra: Mm-hmm.

Patrick O'Shaughnessy: Sometimes it's literally a conversation with a person that just smacks you in the face and makes you feel validated, maybe for what you're trying to do. There's a gentleman named Reece Duca who's very, very private. And there's no content about him or interviews with him. I wish to God I could, he would let me interview him. I know he never will. Who has been incredibly impactful on at a philosophical level, he has all these amazing little phrases, but his life kind of boils down to simplicity, the beauty of simplicity. He gave me this line one time, "Simplify your life with rhythm and harmony." And that line is what you're talking about. Fewer deeper relationships, fewer things better, everything aligned with what gives you energy, listening to your own, the feeling of aliveness.

Patrick O'Shaughnessy: He lived that to a degree that's rare that I've never seen. So, I could keep, I literally could rattle names. A gentleman that I spend a ton of time with now named Jesse Beyroutey, who I am with basically every day, who also I think has no interest in fame or accolades or recognition, but I think is one of the great, will go down, I would predict, as one of the great investors ever. And he's like Reece, he's completely uncompromising and the most principled way of living I've ever seen. Just like refuses to get sucked into the game. And, God, man, I could rattle off names for hours and hours. I mean, there's so many people that have influenced me. And that's what makes this all fun, that's what makes what you and I do so fun is I'm inspired constantly.

Patrick O'Shaughnessy: And you're doing this new show. I interview people once a week, but really I interview 10 people a day. That's what I do. I just happen to have mics there one of the times, if I'm doing it 40 or 50 times a week, which is not an exaggeration, it really is that many people every week, just like, "Who are you? What's your deal?" I love doing that. And so there's just too many, too many to name, but those are a couple that came to mind.

David Senra: ... Munger said, I'm paraphrasing, but he's like, you know, "One of the best ways to learn is, like, you find somebody that's kind of an outlier and you just ask them, like, 'What the hell is going on with this person?'"

Patrick O'Shaughnessy: Yeah.

David Senra: And you just keep asking that question to try to get deeper and deeper and deeper about, like, reverse engineer of what they're doing and why they're really successful. There's another fascinating thing where there's, like, this meme where it's like everybody has a podcast now, and everybody starts podcasts. And as soon as that takes hold, you've been doing podcasting for 10 years, and you decide, "No, I'm going to go in a different direction."

David Senra: And the majority of our conversations, I would say, now are not even about the podcast, they're about these profiles that you're writing on Colossus. Some of them have been so incredible that I actually used them as source material for a "Founders" episode. Which I think we should do more of those collabs, because I was like, "They were really well written," kind of, like, doing my job for me.

Patrick O'Shaughnessy: Hmm.

Patrick O'Shaughnessy: Yeah.

David Senra: Why did you decide to do that?

Patrick O'Shaughnessy: I'm, in the abstract, very interested in how I can create and control valuable scarce units of attention and then dole those things out to the people that we believe in.

Patrick O'Shaughnessy: At a very high level, the reason we now have a magazine, which on its face I think everyone would've agreed was a stupid idea, or told me it was a stupid idea when we started it, why are we doing these profiles that take months or quarters or years to write and require lots of investment? Why do them?

Patrick O'Shaughnessy: Well, the reason is, I think it's just a beautiful way to shine the light beyond, like, podcasting on people that we admire, and to teach someone, to teach the world about a compelling founder or a compelling investor or artist or whatever.

Patrick O'Shaughnessy: And the thing that I didn't realize with that was that because I'm not writing the profiles, our amazing team is writing them, it would actually be a double whammy that not only when we started doing this I went and read David Remnick, who's the editor, longtime editor for The New Yorker, and New Yorker profiles were always my favorite growing up, these incredibly detailed, amazing, well-written profiles. He wrote in the introduction to his compilation of his favorite New Yorker profiles.

Patrick O'Shaughnessy: There's this line that says, "The best profiles over the last 100 years are defined by somebody doing a thing they're obsessed with and a writer that is as obsessed with the person as the person is with the thing." And I remember reading that paragraph and just thinking, "Wow, that's what I want to read." And so I went and I read a million profiles, and the very best one I read was in a publication called Tablet on Palmer Luckey from Anduril. And I reached out to the author, his name is Jeremy Stern, who's now the editor-in-chief at Colossus, and the rest of that story is sort of history.

Patrick O'Shaughnessy: He joined, we've got other people that have joined or are joining to write these profiles, and it just felt like, wow, this is another way to do the thing we love to do, which is to find the person, become obsessed, learn everything about them, take great time and pain to write a definitive thing about them, and then share it with millions of people.

Patrick O'Shaughnessy: And, you know, the fact the one that we wrote about, Josh Kushner and Thrive, was one of these bizarre "break the internet" moments when it just, like, completely took over the internet for a while. And I remember reading it the first time, and I was, like, 45 minutes into reading it, and I was still reading about the Holocaust.

Patrick O'Shaughnessy: And I don't think anyone else would take that risk in a profile of Josh and his family and his team, but it was so important to understanding the soil out of which his family and eventually he emerged. And Jeremy also, the writer, was the product of Holocaust survivors himself and knew a tremendous amount about Josh's family history because it was also his family's history.

Patrick O'Shaughnessy: And I thought that was the coolest, most beautiful thing. I would, you know... So this project has become an excuse to first of all, find more talented people, the writers, that we can support, which is great see the potential, you know? Same thing we've been talking about over and over again. So now team members become more people that we can do this supporting thing with, and for them to write things they're obsessed with and passionate about, and then for the rest of the world to benefit, for the people being profiled hopefully to benefit if we tell the honest stories, and we want to tell the hard parts and the interesting parts. And it's been successful beyond what I ever could've imagined.

Patrick O'Shaughnessy: And I think it's important to note, like, when I started with the first idea, everyone said it was a stupid, I mean, literally everybody said it was a stupid idea. When I started the podcast, everyone said it was a stupid idea. When we started Canvas, everyone said it... I think if people say something's a good idea, I always get a little nervous because if it sounds like a good idea, it just feels you're in a more competitive space, it's going to be harder. I think the key is stuff that sounds dumb but isn't.

Patrick O'Shaughnessy: And I think that's what I would, you know, starting a magazine in 2025 I think falls in that category of sounds dumb, magazines are dead or dying. But the thing underneath it was this desire to have more ways to do the thing that we love to do, which is find people, learn about them, tell the world about them. I suspect it won't be long until that's much bigger than even the podcast, which itself is, you know, very, very big.

David Senra: The surprising thing is I think you want that to be the case.

Patrick O'Shaughnessy: What specifically?

David Senra: Colossus being bigger than the podcast.

Patrick O'Shaughnessy: Of course.

David Senra: That's not an "of course" thing, you've got to unpack that, you've got to explain why you feel that way. I know you don't know how other people view you, but I get a lot of this because they know of our association. They're like, "This is the best business interviewer in the world and this is incredible. Like, why would he not want that to be the biggest thing?"

Patrick O'Shaughnessy: I'm not saying I want to keep doing that.

David Senra: I know you, I know that.

Patrick O'Shaughnessy: For sure. I love it.

David Senra: But I think in your heart, if you had to choose, you'd be like, "No, I'd rather have the profiles be bigger." Again, this goes back to how I think, how we started the conversation. Like, I really do believe you would like to be the guy behind the guy.

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: That's true, but the reason for me is almost so obvious that it's uninteresting, which is, well, if a bunch of other talented people are doing this and then creating these things, first of all, I'll have more of them so I can enjoy them more. And I'll get to enjoy it just like everybody else. Like, I can't tell you how fun it is to get the first draft of one of these things in Slack. The things that make me the most giddy in my work are some new draft that they've created for Colossus and some new research reports on an investment created by my incredible team on that side, who, in many ways, are just doing the...

David Senra: Mm-hmm.

Patrick O'Shaughnessy: It's turtles all the way down, like it's the same deep investigation, publishing, writing, clear thinking. When I get one of those two things in the morning, oftentimes, sometimes there's days where I have several of them, those are the best days. And so, selfishly, I would just love a world where I'm not needed at all because that means we're creating more of them. Obviously, I'm limited by my own bandwidth and time. I'll always do interviews.

David Senra: Yeah.

Patrick O'Shaughnessy: I hope it gets bigger and bigger and I don't want to fade into the sunset. But I hope this is much bigger, because that means I get to hire more incredible, talented people and hopefully put them on a career trajectory that's the best it could possibly be. And that's incredibly gratifying. I get to read more of these things. I get to do this thing that we love to do for more people and point the light that we're trying to cultivate on more and more talented people.

Patrick O'Shaughnessy: That's unbelievably exciting. I hope it's not just writing. I hope it's a documentary. Who knows where it goes? I hope we start convening people in small situations where, "Meet this person." Like, that, to me, is the most fun thing in the world. And so, a world where it's no longer rate limited by my time and energy is much more exciting than a world where it's me.

Patrick O'Shaughnessy: So yes, I would vastly prefer that all the rest dwarf whatever I do, even though I hope what I do lasts forever and is big itself.

David Senra: I don't remember the first time you brought up this idea to me. Now, it seems obvious in hindsight, right? Because people have been reading profiles-

Patrick O'Shaughnessy: Yeah, now everyone's launching a magazine and it's going to be like podcasts.

David Senra: But not only that, like, specifically profiles. Where people have been reading, like you just mentioned it. I bought that book too that you told me about, the New Yorker called... Like, people have been... They're always interested in people. I remember reading, Larry Ellison loves to pick fights, and he thought it was, like, really good. And he didn't like the fact that Oracle... He had no media strategy for Oracle and he's like, "Oracle is just compared to other database companies and I don't like that. I want to be compared to the best companies in the world."

Patrick O'Shaughnessy: Yeah, yeah.

Patrick O'Shaughnessy: Of course.

Patrick O'Shaughnessy: Yeah.

David Senra: It's almost like this idea me and you bond over that we both learned from Jared Kushner, constant refinement of association. So he's like, "I don't want to be compared to CBASS or however you say it." Like these other state. What is it?

Patrick O'Shaughnessy: CBASS?

Patrick O'Shaughnessy: From Dumb and Dumber, that's from Dumb and Dumber.

David Senra: Well, I don't know what it's called.

Patrick O'Shaughnessy: CBELL? That's probably it for you.

Patrick O'Shaughnessy: David, not an investor. Podcaster.

David Senra: There you go. Forever. All my vocab comes from the written word. So, you know, everybody makes fun of me because all my DMs are like "You mispronounced this word. It's very obvious, buddy." But his whole point is like, "I don't want to be associated with these people. I want Oracle be in the same vein as IBM or Microsoft."

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: Yeah.

David Senra: And so he's like, "The way I'm going to do that is I'm going to pick a fight with Bill Gates and Microsoft," and he does this huge fight. And originally, he thought that it was going to be, you know, Microsoft versus Oracle. And he's like, "But people are interested in personalities more than they're interested in companies or technologies."

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: Of course.

David Senra: So it became billionaire A versus billionaire B.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And it greatly elevated his profile, and then he said that Oracle and Oracle's products were risen, like, came along with the increase.

Patrick O'Shaughnessy: Right.

David Senra: So, the reason I bring that up is because people are fascinated with profiles of other people. We are fundamentally more interested in other people and, like, what they can teach us about ourselves than anything else. What were you thinking? Because that was something that existed forever, and who writes great profiles now? I don't even see any of them.

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: That's the other part that's exciting, is because I like things that are really hard. Okay, so originally... Hardship, we didn't talk as much about hardship. I think you've been talking a lot about doing something that's different just because it's different. I would add on, which I think is interesting and correct, but I would add onto that, like, it should be different and really hard. Like, really hard to do. And I'm sampling all the profiles we've written in my head.

Patrick O'Shaughnessy: Some of them are ridiculously hard to write. Not only because of all the hours and work that has to go into it and the talent as a writer that has to go into it, but sometimes, it's sensitive parts of the person's life that's never been written about and they've never talked about, and maybe they don't want to talk about it or they don't want you to talk about. And it's the coaxing it out of them, and that takes time and trust. And so the thing I can't wait for is the profile that we write 10 years from now that we start working on today. We have this idea, which we've started to do, where we just ask people, "Can I just have lunch with you once a year? I'm not going to do anything with it, like, I just want to start collecting the line."

David Senra: Mm-hmm.

Patrick O'Shaughnessy: "And maybe we'll write something in 10 years," you know? So, things that are really hard to make are really interesting to me, and I think people stopped doing profiles because they're really hard to make. They take time, the business model kind of sucks. Like, the pay is terrible. You know, profile writers are not paid well. The world went a different direction. It's much cheaper and faster to make a stupid fucking TikTok than write a 50-page profile about someone that's careful and intricate and well-written.

Patrick O'Shaughnessy: You and I certainly talk about this all the time, the world is desperate for some stuff like that. The world is so sick of this crap, just all day, every day. It's just crap. And everyone makes the junk food comparison because it's a perfect comparison. Like, junk food got to where it was because it's been optimized for us to want the most of it possible. Whether or not it's good for us, it's obviously horrible for us.

Patrick O'Shaughnessy: It's the same thing with most content, and everyone knows this in their gut, and we all want something more carefully created. And I think Profile might be perhaps the ultimate expression of that. If a documentary is the ultimate profile, maybe that's even harder than writing a profile. But, yeah, I'm interested in stuff that's very hard to make and that's singular, that can't be easily copied.

Patrick O'Shaughnessy: And, I mean, the literal answer to your question, it's kind of funny, was somebody I'm actually seeing him Monday, gave me the idea to potentially buy this existing magazine. And we didn't buy it because I like to create our own things primarily, but it was notable to me that this magazine, which had been around for a long time, had all these incredible... I'd never heard of the magazine, and it had all these incredible people on the cover and I thought, "This is strange."

Patrick O'Shaughnessy: Like, "Why are these people doing this magazine that no one's ever heard of?" Big names. And it dawned on me, I was like, "Oh, it's the cover." People can't say no to a cover. And so I tested that theory out and it was true, and I think what that means is it's, like, the ultimate form of spotlight and attention that you can give to somebody, and so that's what got me actually literally spinning on, like, "Oh, maybe we should... I would love to have a cover that I could dole out."

David Senra: Did that idea come before or after you read Jeremy Stern's piece on Palmer Luckey?

Patrick O'Shaughnessy: Before. So I was then on the hunt, and this is another idea that you and I talk about often, which is, if you want to hire someone for a thing, just go consume as much of the thing made by a million people as possible. Whoever made the best one, go for them. There was this funny conversation during COVID, an investor friend of mine, one of the great investors ever who's now retired, it was part of the Zoom conversation, and the topic of the conversation was attributes of great founders, and at some point someone goes, "Well, maybe it'd be easier to think about them not as founders, but as inventors," and everyone thought, "Oh, that's a cool idea.

David Senra: Yep.

Patrick O'Shaughnessy: Okay, let's talk about them as inventors, not as founders." And then someone said, "Well, what are the attributes of a great inventor?" And people started, you know, "They're this, they're this, they're this," and this one investor's face started contorting and you could just see that he was frustrated by all these answers, and it got to him, and he was like, "Morons, who cares? Did they make a good invention?" Like If the invention is good, the inventor is probably good.

David Senra: Yeah.

Patrick O'Shaughnessy: And so I think you and I have taken that approach to... I certainly have, to finding people. Like, just look at what they did. Jeremy wrote the best profile that I read. Turns out he's a great profile writer. Like, he's written 10 more and will write 100 more. I was then on the hunt after and we had this idea to go now, "Okay, now let's go find the best people to do this thing."

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David Senra: A few months after I started using Eight Sleep, I randomly ran into Mateo at a restaurant, and I was with some friends, and I went over to say hi. When I got back to my table, my friend asked me who that was. I said, "That's Mateo, the founder of Eight Sleep." And then my friend said something hilarious. He replied, "He looks like he gets good sleep." Mateo is living and breathing his product. I never had the ability to change the temperature of my bed before I had an Eight Sleep. I had no idea how much that would improve the quality of my sleep. I keep my Eight Sleep ice cold.

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David Senra: People vastly underestimate the importance of volume.

Patrick O'Shaughnessy: Yeah.

David Senra: Like, whatever you're into, just be into it more than anybody else and, like, you'll be able to tell, like, what is a good idea, what is a bad idea. It's, like, this constant refinement of taste. In fact, I was shocked at the way your profile started with, about Josh Kushner and where it was, like, this visit to Rick Rubin's house, and I'm a huge Rick Rubin fan.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: Like, I read a biography on him, I think it's episode 245 of Founders, did that, I think some of his interviews and stuff he says in an interview, it can be a three-hour conversation and you just hear, like, there's, like, a 45-second clip that makes everything, like, it just makes perfect sense on like, I needed to hear that whole three-hour conversation just to get that 45-second clip and that 45-second idea in my head. But if you think of the guy started his record company in, like, 1984 in his dorm room.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And he's been in the same business, he's worked with all these different musicians. In fact, he said something that was interesting to me, and I actually screenshotted it, saved it, and I reread it on my phone. And he talked about that the most obsessive artist he ever worked with was Eminem, which is, like, wait a minute, you worked with everybody, you've had a four-decade-long career. Why is that the case? Like, that makes me want to know more about that. Our mutual friend, Brent Beshore, told me this hilarious story one time. You know, Brent's got a...

David Senra: He owns a bunch of different companies, and sometimes those companies need a CEO. And he found himself, I think, at a lunch or a dinner with Charlie Munger, and so he's like, "You know, I'm this young guy." I think he was probably 35 at the time. He said, "I own these, like, 12 companies. How do you and Warren find great CEOs?" And Charlie's just like, "We just find somebody that is a great CEO and say, 'Come do that for us.'"

Patrick O'Shaughnessy: Yeah.

David Senra: And Brent's followed up, he goes, "Yeah, but what about hiring for potential?" He goes, "We don't do that." It's just a beautifully simple idea. "He's really good. Can you come do this over here?"

Patrick O'Shaughnessy: Yeah. Yeah. People show you. And I think that also, if you invert that, to use another Mungerism, it serves as great advice too, which is if you're trying to get ahead, put stuff out in the world that people can find. Hinkey would call these breadcrumbs. Put breadcrumbs out into the world so that people see it and are amazed by it. Like, if you create a single thing, not... You don't have to do 10 things. Just one thing that people are amazed by.

Patrick O'Shaughnessy: Pour a year of your life into making one amazing thing that people are amazed by and amazing things will happen, I promise you. Like, the internet is amazing at sharing something that is great. You say there's always room for great.

David Senra: Yeah.

Patrick O'Shaughnessy: One of your maxims. That's true. Great takes time. Great's hard.

David Senra: Well, you just proved this. The idea of there's always room for great came because so many people are like, "We don't need another podcast." I was like, "Okay, so we don't need any more music?"

Patrick O'Shaughnessy: Yeah.

David Senra: "We're going to stop making music? We're going to stop making movies?" Like, no, it's just like we need less bad shit, but that's always going to happen. Like, there's always room for great. You just proved this with The Profiles.

Patrick O'Shaughnessy: Yeah.

David Senra: Like, that idea was just hiding in plain sight. It was just not being done well. And it's like, well, what if I just take this idea and not make it shitty? Well, how Walt Disney towards the end of his life was very fascinating because everybody associates him with animation and Mickey Mouse and everything else. And yet, when he's towards the end of his life, you just ask, "What is the things that he's most proud of?" And he said he named two things. He said, "Keeping control of my company," because he lost control of his first company, and he's lost control of the first characters he made, "and Disneyland." And Disneyland was his obsession.

David Senra: In fact, I read this book called "Disney's Land." I think it's by Richard, this guy named Richard Snow. And it's not about the animation, it's not about everything we know him for. It's about how he thought about making this amusement park. And at the time, amusement parks were think of low quality.

Patrick O'Shaughnessy: Yeah, sure.

David Senra: They were kind of scammy because-

Patrick O'Shaughnessy: Traveling carnies.

David Senra: Yeah, exactly. Like, you would come in there, and there'd be, like, games to play, and you'd get ripped off because the games were set up and everything else. And he's going around trying to raise money for this, very unsuccessfully. And they're like, "Yeah, but, you know, amusement parks are, like, kind of trashy." He's like, "That's the point. Mine won't be."

Patrick O'Shaughnessy: Yeah.

David Senra: It's because, like, mediocrity is always invisible until passion shows up and exposes it.

Patrick O'Shaughnessy: Yeah.

David Senra: And he's just like, "I'm just going to take every single part of this and make it better, and then remove the parts that don't make any sense."

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And, like, that's a great filter for finding, you know, new things to create in the world.

Patrick O'Shaughnessy: By the way, I spent my 20s basically just reading. And I read more than you can imagine. I mean, you're probably the one person that can't imagine it because you did something similar. But I wasn't just doing... I mean, literally everything I could get my hands on. Thousands of books and profiles and everything. And I started the podcast in part because I started to feel this awful feeling of this is happening in this weird, isolated way. Like, it's just me and my notes.

Patrick O'Shaughnessy: I'm not talking to anyone about these books. And so I wanted to start sharing, which is where that book email came from that you originally... That's where the audience came from. Like, I used to have this saying, "Learn, build, share, repeat," and just do that until I die. And I believe in that. And so it's-

David Senra: Still, wait. Learn, build, share, repeat?

Patrick O'Shaughnessy: Yeah.

David Senra: Still really good.

Patrick O'Shaughnessy: Still works.

David Senra: Yeah.

Patrick O'Shaughnessy: And maybe that's my governing principle, probably, like you said before. And, yeah, it's an incredibly powerful loop to go on. But that 10 years of reading prepared me to be a good producer of Profiles because I've seen great, I've seen good, I've seen average, I've seen bad. My reps are very, very, very high.

Patrick O'Shaughnessy: And that's another thing I always tell people, especially young people, like, what is the thing where you naturally have a lot of reps because you just like it? Build off that because there's this learning-by-doing concept. Like, you get better at something just through being prolific in the thing, and most people have a thing for which they are naturally prolific. Even if that's following your sports team or whatever it might be. Like, what's the thing you just can't help but do a crazy high rep count of?

Patrick O'Shaughnessy: Probably that's a good clue to, like, where you could go build one of these compounding curves for yourself. And for me, my first love was reading. That love of reading became the email list. You know, here's my four favorite books from the month. The email list gave me my first set of people to listen to the podcast. The podcast introduced me to all these people who helped me build my business and sell it successfully. You know, and on and on and on. That led to it-

David Senra: Led back to The Profiles.

Patrick O'Shaughnessy: That led to The Positive Sum 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 An 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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, now look. That's like my constant urging to people, like, "It's there, I promise. There's something, just go find it."

David Senra: I think that was beautifully said. We haven't even touched on investing which I want to.

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: Let's do it.

David Senra: 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.

Patrick O'Shaughnessy: Hm.

David Senra: Is it seeing red? What did this person say about you?

Patrick O'Shaughnessy: He said I was red on the color wheel.

David Senra: Okay, red on the color wheel. Can you tell that story?

Patrick O'Shaughnessy: Sure. So you, me, and Sam Hinkie were walking, and I think you asked Sam what's my biggest weakness or something?

David Senra: No, you were interviewing... Okay, so-

Patrick O'Shaughnessy: Oh, I was doing that.

David Senra: 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.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: Which is, like, exactly what you said. I'm doing 10 Invest Like The Best episodes a day, I'm just recording, you know. I'm doing 50 a week and I'm just recording one.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: 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. Like, I'll follow the trail around it." It's like, no, billy goats just go straight over and up.

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: Yeah.

David Senra: And like, 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.

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: Yeah, yeah, I remember.

David Senra: 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, like, 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.

Patrick O'Shaughnessy: Yeah, yeah.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: 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.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: 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.

Patrick O'Shaughnessy: Hm.

Patrick O'Shaughnessy: Red on the color wheel.

David Senra: There you go.

Patrick O'Shaughnessy: Yeah.

David Senra: What does that mean?

Patrick O'Shaughnessy: So well, 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

David Senra: This is known lovingly amongst your friends as your Eye of Sauron.

Patrick O'Shaughnessy: Yeah.

Patrick O'Shaughnessy: Okay.

David Senra: 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...

Patrick O'Shaughnessy: Yeah. I-

David Senra: In some cases it's like a physical presence thing.

Patrick O'Shaughnessy: Yeah, yeah.

David Senra: 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.

Patrick O'Shaughnessy: 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?"

David Senra: Do you remember we were at Brad Jacob's house having breakfast or something?

Patrick O'Shaughnessy: Yeah, yeah.

David Senra: He was very disturbed by this, and he tried to fix it.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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. But I understand.

David Senra: It's said in a loving way.

Patrick O'Shaughnessy: 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.

David Senra: What was the example he gave, though? It's too good of a story not to tell.

Patrick O'Shaughnessy: 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?"

Patrick O'Shaughnessy: 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 so, this is before I sold my business. "It's a little bit, you know, tighter situation, and I have to reduce the amount."

Patrick O'Shaughnessy: 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?"

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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: Yeah.

Patrick O'Shaughnessy: 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."

Patrick O'Shaughnessy: 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: 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.

David Senra: Hey, real quick, I need a favor from you. Right now, I'm conducting a survey to better understand the listeners of this show. So, the survey is entirely anonymous. It's going to ask you things like what your position is at your company, what your household income is, things like that. This information is going to help me both keep and attract the best possible sponsors for the show, which then, in turn, allows me to create the best possible conversations for you.

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David Senra: 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.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: 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...

Patrick O'Shaughnessy: Yeah.

David Senra: 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...

Patrick O'Shaughnessy: Mm-hmm.

David Senra: 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: 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, you know, mature business story. And pretty important that that person's a good leader.

Patrick O'Shaughnessy: 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, like, everyone I knew. I was like, "Define good leader. I'm going to do a survey."

David Senra: Mm-hmm.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

David Senra: Some of the best leaders, like when you see in company buildings, like history's greatest entrepreneurs, really think of them as, like, they're teachers, and then they understand the need to repeat, repeat, repeat. I always say repetition is persuasive. You gave me that great Catholic saying where it's like, "Repetition doesn't spoil the prayer." So, I think of, like, Jim Sinegal, founder of Costco. He has this great line in the book, this biography of his mentor, this guy named Sol Price, who basically influenced... He's, like, the most influential retailer of all time.

David Senra: Jim Sinegal was mentored by him, Sam Walton took more ideas from him than anybody, Bernie Marcus got the idea for doing Home Depot from Sol Price, Jeff Bezos took ideas from Sol Price. Like, it's just incredible how influential this guy was, and most people don't know who he is. And in that book, he says that if you're not spending 90% of your time teaching, you're not doing your job as the leader of the company.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And what it is, is like, it means teaching what our philosophy is, what is our purpose, what we do, how we do it, why we're doing it, and you just repeat it over and over again. I just did this episode called "How Elon Works," which is, I think, the most downloaded episode of Founders ever.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: Like, it's just nuts. And what I was shocked, is you don't think of Elon as, like, a... He's definitely a singular character. There's nobody else like him that I've found, living or dead. There's usually some kind of historical equivalent of anybody. I haven't found a historical equivalent of him. And you would think, "Oh, he's working on, like, seven different companies at a time, he can't possibly be like this." And he was mentioning, like, that algorithm, that four-part algorithm he had that he uses in all his companies.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: He's like, "I say it so much, I repeat it so much, that you'll be in a meeting, and my executives will be mouthing the words along with me. They know what I'm about to say."

Patrick O'Shaughnessy: Mm.

David Senra: And I think that has to do with, like, overcommunication. It's like, "We are going to be on the same page. I'm not worried that you hear this for the 10th time, I'm worried that you're not understanding where we're going, or how we're going to do it."

Patrick O'Shaughnessy: Mm.

David Senra: And so I think about that a ton. Like, repeat, repeat, repeat.

Patrick O'Shaughnessy: Mm. Yeah. The joy of that sort of thing and that sort of leader, my favorite... You have all these great maxims. My favorite maxim, pretty much the only one we use in my business with my team, is, "The reward for great work is more work." And I find that saying that maxim to the right person, like the kind of person I want to spend time with, their eyes go wide and they understand it immediately, that the reward for great work is not money, power, fame.

Patrick O'Shaughnessy: It is the privilege to get to do more of this thing that I love doing. The problem with coming up with, like, good terms for this stuff, we use this term "life's work," is that immediately everyone else just starts saying it, and it ceases to have any meaning, because, like, now every goddamn meeting I'm in, like, "I'm doing my life's work." And my experience is that almost nobody is doing their life's work. Even a lot of great founders, I would say, it's not their life's work.

Patrick O'Shaughnessy: I love the fact that Thomas Jefferson, on his tombstone, has three things that describe his life, but one of them is not that he was the President of the United States. It was, you know, author of the Declaration of Independence, founder of the University of Virginia, not President. And I think that's so interesting. And so I think a lot about like, is this thing this person is doing going to be on their tombstone? And usually the answer is no.

Patrick O'Shaughnessy: And the reason I like this concept of life's work so much, which I would define as a lifelong quest to build something for others that expresses who you are, all three parts are really important...

David Senra: Say that one more time?

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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: 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?

Patrick O'Shaughnessy: 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.

David Senra: But they're doing something.

Patrick O'Shaughnessy: Yeah. I don't...

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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."

David Senra: Mm.

Patrick O'Shaughnessy: 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: I think they're like 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: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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. 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.

Patrick O'Shaughnessy: 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.

David Senra: 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.

Patrick O'Shaughnessy: Mm-hmm.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: And it's casual.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: 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.

Patrick O'Shaughnessy: Mm-hmm.

David Senra: Like, I went from like, "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."

Patrick O'Shaughnessy: 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?

David Senra: Bill Campbell.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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 s*** 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: It is so unusual for us to even contemplate that, like, 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.

David Senra: 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, like, generational inflection point.

Patrick O'Shaughnessy: Yeah.

David Senra: 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..."

Patrick O'Shaughnessy: I wouldn't put it past you.

David Senra: 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?"

Patrick O'Shaughnessy: Hm.

David Senra: 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...

David Senra: 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."

Patrick O'Shaughnessy: Mm.

Patrick O'Shaughnessy: "I'm outta here."

David Senra: Yeah, "I don'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.

Patrick O'Shaughnessy: Mm.

David Senra: 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: 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.

Patrick O'Shaughnessy: 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."

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: You don't need to explain it, like, 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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: 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.

Patrick O'Shaughnessy: Hm.

David Senra: 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: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: 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.

Patrick O'Shaughnessy: He went so out of his way for, like, the first six months to, like, organ transplant me into his social circle. And maybe Tim owed me a beer or two, you know, a couple nights out and a beer was his obligation as a family member. But instead, he would call ahead to his friends, saying like, "I'm sick, I can't go out, but Patrick's coming out. Can you just, like, show him a good time?" Just, like, over and over and over again. Like, literally, he just injected me into this community.

Patrick O'Shaughnessy: Tim is the reason that I met my wife, which I'm going to come back to in a second, met my best man, met the only other groomsman in my wedding that wasn't a family member. So, you know, through this act of over-the-top kindness, of just, there was nothing in it for him, he was just doing the right thing, it sort of set me up for the rest of my life. Which brings me to the second thing.

Patrick O'Shaughnessy: So, my first night at Notre Dame, Tim shows up with this fake ID that says I'm five foot four with blonde hair and blue eyes, and we go to a place called Boat Club, which let me in with this fake ID, and was shut down for letting people in with this sort of fake ID, like, three weeks later, permanently. May it rest in peace. And I walked into Boat Club, and the story of meeting Lauren, my wife, was that was my first night in Notre Dame, the first bar I walked into, and she was the first girl that I talked to.

Patrick O'Shaughnessy: And so that is a crazy stroke of divine luck or something, but it was lucky because I was 19 when I met her, she was 20, and, you know, we've been together and married and have kids ever since. And the true answer to kindness is her, because for 20 years now, we just crossed the point of our lives where I've been with her more than I haven't in my life, which is so crazy.

Patrick O'Shaughnessy: I'm not young anymore. I'm 40, but I'm not old. And to have been with her for more than half my life and to have grown up as an adult, whatever they say your prefrontal cortex, like, matures when you're 25 or something, so, like, six years with her where I didn't even have a fully developed brain...

Patrick O'Shaughnessy: It's by far the number one blessing, is that she... Yeah, we have created this life together in a way that... I mean, the 1,000 things, the 10,000 things that she's done that add up to that 20 years is, like, the very clear true answer. Tim tragically died very young, which was awful, but I think about him all the time because without him, none of this would've happened, and this life wouldn't exist.

Patrick O'Shaughnessy: And so I love this story, and I love this question, because whole lives are downstream of simple, quick acts of kindness. And without Tim, my life doesn't look anything like what it looks like today. All the things I care the most about don't exist, probably. And so I remind myself of that every day, which is why I love asking this question.

David Senra: That was awesome. Now everybody else gets to see what I get to see in private, and this is why you should do more podcasts. Thanks, Patrick.

Patrick O'Shaughnessy: Thanks, buddy.

David Senra: I hope you enjoyed this episode. Please remember to subscribe wherever you're listening and leave a review, and make sure you listen to my other podcast Founders. For almost a decade, I have obsessively read over 400 biographies of history's greatest entrepreneurs, searching for ideas that you can use in your work. Most of the guests you hear on this show first found me through Founders.