Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]

This week is a special episode. Only David Senra could get me to be on the other side of the mic. Because I don’t plan on being interviewed often, I wanted to share this conversation, which I so enjoyed, with our audience. It went in a very different direction than I expected. We barely talk about investing or interviewing. Instead, we talk about finding an organizing principle for life, undiscovered talent, and the idea that “the reward for good work is more work.” We also discuss the principles that guide how I think about building Invest Like the Best, Colossus, and Positive Sum. This conversation was originally recorded and released on David Senra, and I wanted to share on the Invest Like The Best feed as well. Please go follow what he’s doing, there’s no one like David. Enjoy! For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠'s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. ----- ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta is trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest. ----- ⁠Rogo⁠ is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps (00:00:00) Welcome to Invest Like The Best (00:04:26) Intro (00:05:14) The Joy of Championing Undiscovered Talent (00:07:33) How One Tweet Changed David's Life (00:10:16) The Upanishads Passage That Shaped Patrick's Worldview (00:15:32) Growth Without Goals (00:17:24) Why Media and Investing Are the Same Thing (00:33:05) The Search for True Understanding (00:35:36) The Daniel Ek Dinner That Launched David’s Podcast (00:39:02) Making Your Own Recipe From the Ingredients of Great Lives (00:43:46) The Privilege of a Lifetime Is Being Who You Are (00:52:06) Bruce Springsteen (00:57:23) Clean Fuel vs Dirty Fuel: The Source of Your Ambition (01:01:43) The Unfair Advantage of Podcasting (01:04:12) Relationships Run the World (01:11:10) The Origin Story of Invest Like the Best (01:12:45) Building Colossus: Why Start a Magazine in 2025 (01:18:42) People Are More Interested in People Than Anything Else (01:22:12) Hiring Through Output (01:26:23) Learn, Build, Share, Repeat (01:30:01) The Daisy Chain: How Reading Books Led to Everything (01:33:15) Red on the Color Wheel: Sam Hinkie's Observation (01:40:17) Finding Your Superpower and Becoming More Yourself (01:45:06) Repetition Doesn't Spoil the Prayer: Teaching as Leadership (01:48:11) Life's Work: A Lifelong Quest to Build Something for Others (01:52:00) The Ten Roles Game and What Matters Most (01:59:12) Husband, Father, Grandfather (02:01:52) The Kindest Thing

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Patrick O'Shaughnessy?

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• 0:42Patrick O'Shaughnessy?

  draft SIMs, run buyer outreach, and do diligence on data rooms, all with full security and compliance handled. Every action feeds Rogo Intelligence, the firm's context layer, turning years of deal experience into a secure, governed institutional memory that makes each new transaction stronger than the last. To learn more, visit rogo.com/invest. OpenAI, Cursor, Anthy, and Vercel all have something in common. They all use WorkOS. To achieve enterprise adoption at scale, you have to deliver on core capabilities like SSO, SCIM, RBAC, and audit logs. Instead of spending months building these mission-critical capabilities yourself, you can just use WorkOS APIs to gain all of them on day zero. Visit workos.com to get started.

• 1:30Patrick O'Shaughnessy?

  Hello and welcome, everyone. I'm Patrick O'Neal, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus, along with all of our podcasts, at colossus.com.

• 1:54Speaker 01

  Patrick O'Neal is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.

• 2:22Patrick O'Shaughnessy?

  This week, we have an unusual episode because I am on the other side of the mic on my friend David Senra's new show called David Senra, in which he interviews me. I've chosen for the last five or six years to never be interviewed, mostly because I love doing what I do so much, shining a light on an investor, a founder, a thinker of some type who I can learn from. But after we did the show, I thought it would be a neat and rare opportunity to share with you all how I think about a lot of things as we build Invest Like the Best, Colossus, and Positive Sum. I really hope you enjoy this little bit different and special episode with David Senra. And please be sure to go check out his new show, where he is interviewing some of the greatest living thinkers, builders, entrepreneurs in the world called David Senra. Make sure you go subscribe to that as well and enjoy the interview.

• 3:10Speaker 02

  You have this almost obsession with finding talented, but not well-known or relatively unknown people. And then you essentially spend a lot of time talking to them, developing relationships, and then putting all of your resources behind that person.

• 3:28Patrick O'Shaughnessy?

  Yeah.

• 3:28Speaker 02

  What is going on there?

• 3:30Patrick 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, I just enjoy that. 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. It's just what I enjoy doing. If I look back on my life,

• 4:14Patrick O'Shaughnessy?

  the, the sort of like wins that I've had, the, the things that if you were to write like a Wikipedia article about me would be like 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.

• 4:32Patrick O'Shaughnessy?

  For whatever reason, I just, that's just not what I enjoy. But when your success happens, or when many other people that I and my team have championed have a win, I feel that deep in my like 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, my, you know, the CEOs of companies that we've invested in, people that we have on our show that we tell the world about. That's the repeated thing that I love. And I also kind of like picking sides. I like saying I like this person and by extension, I like them more than the other available options in this field

• 5:16Patrick O'Shaughnessy?

  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.

• 5:28Speaker 02

  I screenshotted this text, this is like many years ago, somebody was asking me, I can't remember who it was now, but they were asking me like what Patrick is like. And I was like, well, positive sum is definitely like a way to describe him was like, and he doesn't do things for money. Like that doesn't mean he's not commercial, like he makes a lot of money. He's going to continue to make a lot of money, but that's like not the driver behind it. Let me go back to like the one of the craziest days of my life has directly involved you, right? Like I was like in the middle of this like five and a half year struggle of like being obsessed with something I know I truly cared and thought was really good. But the external world was like, no, like nobody gives a shit about what you're doing, David. And, you know, I kept doing it.

• 6:13Speaker 02

  And we have a mutual friend in Sam Hinkie, who's going to get, keep getting annoyed because I bring him up on every podcast that I go on.

• 6:19Patrick O'Shaughnessy?

  Cause like He's deserving of the mentions.

• 6:21Speaker 02

  The two episodes he did with you, like especially the one about like find your people, I think is that

• 6:25Patrick O'Shaughnessy?

  That's a beautiful one.

• 6:26Speaker 02

  I go back to that one all the time and the notes that he says in there. And like one of the things I think about all the time. Which, again, I'm not an investor, but I want like access and I want deep relationships with people, very high quality people. And I, it's just like, he's like, people are power law and the best ones change everything. And so, once you actually see that, you are very, almost like ruthless with who you let have access to you. And I think I'm getting very ruthless and continue to be ruthless because of like what I'm, you know, kind of chasing after. But I had like no followers on Twitter at all. And just like tweeting to the oblivion, like no one gave a shit what I'm doing. And one day, this is why it's like one of the first things that I think speaks volumes about you

• 7:11Speaker 02

  and how you actually live your life. And like, I think you've now leaned into this more over the last like 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? The only time, there used to be a same guy that had my name and he was like a Brazilian MMA fighter. So when he would fight.

• 7:30Patrick O'Shaughnessy?

  Oh, that's funny.

• 7:31Speaker 02

  Yeah, it's like, but all the tweets are in Portuguese, so I don't know what they're talking about. It's not about my podcast. And I almost remember verbatim, I should go and find, see how much I can get the text inside the tweet, correct? But you're like, I never find new podcasts to listen to. And you know, that's like the best. It's like, people don't know, it's just like insanely, one of the most insanely valuable audiences in the world. If you could like sketch out the average net worth of listener service, 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 Center's Founder's Podcast is excellent. You should listen to it. And you linked to an episode on Estee Lauder, which is one of my favorite ones.

• 8:15Patrick O'Shaughnessy?

  I loved that episode, yeah.

• 8:16Speaker 02

  And you sent 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, you know, 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 logged into my email and it's just

• 8:39Patrick O'Shaughnessy?

  A wall.

• 8:40Speaker 02

  Whoosh, all the way down, just like, 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 is going on there? You didn't see it as a competition, you didn't, what was, what was happening?

• 8:55Patrick O'Shaughnessy?

  The first thing that flashes to 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, those 500 answers or whatever, and categorized them and like made a pie chart of like 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, first answering the question, before I deserved it, or like they saw something in me that maybe I didn't even see in myself. They, they bet on me before others would. And that was the answer to the, the kindest thing.

• 9:34Patrick O'Shaughnessy?

  And when I was 26, I, I became very interested in, uh, all of the, I, 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, I was kind of, uh, I was in a weird spot in life. 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's 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 thousands of years ago that were oral, passed down orally through, through generations and then eventually written down.

• 10:17Patrick O'Shaughnessy?

  And I remember getting stuck by this, on this one passage that literally felt like someone hit me in the face with a hammer. And there, there's a, a line in this passage that basically says something like, like, "Those who feed the hungry protect me, those who don't are consumed by me." And

• 10:36Patrick O'Shaughnessy?

  It just felt like there was like a moment of understanding that happened in my head. But up until that point from teenage, you know, middle of teenage, I was a nice, sweet boy. And then I got kind of hard hardened and went through a period of life that was tough. And it just, it like 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 that like, that's probably the thing that most informed my worldview. 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

• 11:16Patrick O'Shaughnessy?

  in somebody before everyone else and then helping the world see what I see. Like if I could 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.

• 11:41Speaker 02

  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.

• 11:56Patrick O'Shaughnessy?

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• 12:26Patrick O'Shaughnessy?

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• 13:10Patrick O'Shaughnessy?

  I believe that the firms that come out ahead in the AI era will be the ones running on RidgeLine's unified platform. If you're serious about your firm's AI strategy, RidgeLine should be part of that conversation, and you can request a demo at ridgeline.ai. You said before you're chasing something, right? Yeah. I'm not chasing anything. I think it might be an interesting conversation today to talk about 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 "Growth Without Goals." And so I'm not chasing any particular thing. I don't have a big,

• 13:55Patrick O'Shaughnessy?

  hairy, audacious goal or something like this. I don't want to put someone on Mars like Elon Musk. And I'm not 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? Yeah. It was a talk given by a computer scientist named Brett Victor, and he espouses this idea that you should find a principle. That you want to, his principle was creators, digital creators, should have instant feedback with their creation.

• 14:38Patrick O'Shaughnessy?

  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 a result, there was this gap. And so his principle was 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. It's, that's the point.

• 15:16Speaker 02

  Well, 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 see like the media, we've talked about this a million times, but like the media and investing are not two separate things. They're the exact, if you actually know Patrick and what is important to him, like they are the exact same thing.

• 15:34Patrick O'Shaughnessy?

  It's taken me a long time to articulate that principle, decade. And that's okay. Like, don't get discouraged if you don't watch Brett Victor's talk and can't name your principle an hour later. Like, it takes time. But you know you 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. 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?

• 16:15Patrick O'Shaughnessy?

  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. 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 is it's a great way to make progress. 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.

• 16:57Patrick O'Shaughnessy?

  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, text me about you. Like, I wasn't looking for a podcaster to promote. Yeah. You were not, you were not the result of some goal that I was seeking. You were just something that like came out of the 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, and so I'm very enamored of this idea for how to live. At what age did you stop having goals?

• 17:36Patrick O'Shaughnessy?

  Well, this essay that I wrote, I wrote, I'm 40 now. I wrote when I was 28. Because I wrote it, I wrote it on the train. I used to commute back and forth from New York City to Stanford, Connecticut. And I was, I was about to have my first child, my son Pierce. 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 on his birthday every year and things like this. And I'm going to give him a packet of letters as well when he turns 21.

• 18:21Patrick O'Shaughnessy?

  And I remember starting, starting this process of wanting to write him a letter before he was born. And it gets, 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. It's so, it's, I don't like telling. I'd rather just set an example. But I was thinking, what example do I want to show Pierce? And, and then I don't remember my exact chain of thinking, but it ended up in this idea of, 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.

• 19:04Patrick O'Shaughnessy?

  They don't do what you tell them. They do what you do. They just copy you. 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.

• 19:22Speaker 02

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

• 19:30Patrick 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 Brett 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 Brett Victor. 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,

• 20:14Patrick O'Shaughnessy?

  and applied it as the primary design principle to software that I built in my last business, which worked really well. The software itself worked really well. 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, I 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.

• 20:48Speaker 02

  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. And I find that in my own self. Like, I do think... I can't explain, like, I have like a lot of willy, like, foo-foo part of, obviously, this is the line you laugh, but like, I have this like willy-foo-foo part of it, it's just like, I just go off feeling, like, an intuition for like, a lot of things that I do, and like, I don't wanna have to like, describe why I believe this to be true, or why I wanna, um, like, pursue this path, or why I think this idea is interesting. I think it's just something inside of me that, like, language cannot describe.

• 21:24Patrick O'Shaughnessy?

  I don't know if it was Alan Watts that said this, uh, he was, he had such a way with words that maybe it was him. It might have been Joseph Campbell, but something to the effect of, um, 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, uh, 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. 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,

• 22:06Patrick O'Shaughnessy?

  I think is a really, a really great thing, and that's certainly how I, I remember that line, reading that line 15 years ago as well. And then starting to chase the feeling of being alive, not, not a goal, but just that feeling. And, um, everyone can answer this question, by the way, it's, it's a really, it's a great way to have a conversation with someone, is to kind of feel, ask them where they feel this, and, and then also why they're not doing more of whatever the answer happens to be, which is a funny, 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.

• 22:38Speaker 02

  That's a very interesting question, what's your guess on why they don't?

• 22:41Patrick O'Shaughnessy?

  Usually, it's, it's, it's simple, which is, um, fear. Fear that by pursuing an original path, I have this idea that, uh, the best story always wins. And I actually spent the last couple of months, like, really trying to figure out, what, 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. And if you dig into originality,

• 23:11Patrick O'Shaughnessy?

  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. 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.

• 23:47Speaker 02

  You've said to me before that you used to be a masochist for introspection. First of all, when did that stop? And then do you think that helped you find this organizing principle for your life?

• 24:00Patrick 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 like sit and hold my hand for me to fall asleep at night. And the reason was I would just sit there like spiraling on this crazy idea, maybe this is why I studied philosophy, that like someday I would not exist. And that just freaked me out and did for decades. 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.

• 24:44Patrick O'Shaughnessy?

  Because I wanted to know what the hell is the point of all this? Like, what's the point? 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. 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 like 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. And now I have very little introspection left in my life.

• 25:29Patrick O'Shaughnessy?

  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.

• 25:44Speaker 02

  You solved the problem that you were using it.

• 25:46Patrick O'Shaughnessy?

  Yeah, maybe.

• 25:47Speaker 02

  Introspection was the tool and then like you don't need to use the tool once the job is done.

• 25:50Patrick O'Shaughnessy?

  Yeah, maybe. Maybe that's right.

• 25:52Speaker 02

  You mentioned earlier that we have different approaches and then you wanted to talk about that. What do you think? Like, I'm always curious, again, like some of the stuff I should not say on a podcast, but I'm always curious, like, people that know me well.

• 26:06Patrick O'Shaughnessy?

  Yeah.

• 26:06Speaker 02

  Like, what is their interpretation of like their view of me that is different than my own? So like, what do you think my organizing principle is?

• 26:17Patrick O'Shaughnessy?

  Your organizing principle?

• 26:20Speaker 02

  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.

• 26:28Patrick 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.

• 26:38Speaker 02

  Okay.

• 26:38Patrick O'Shaughnessy?

  And my principle is that is when I do, it is my obligation with nothing. Maybe I invest, 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, 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.

• 27:22Patrick O'Shaughnessy?

  The world when that happens pulls you into this branching exercise where you end up doing lots of different stuff. And that, you know, 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, you know, why are you doing it?

• 27:47Patrick O'Shaughnessy?

  I mean, I think you've talked about this certainly in private with me, but also in public about, you know, you came from, we came from opposite circumstances. Like I was, 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, in the United States. He was an oil wildcatter. First, first oil hole he ever drilled, I think, still pumps oil to this day in, in the Midwest. And so he was a giant, he was broken up in the antitrust, you know, in the Rockefeller antitrust stuff

• 28:32Patrick O'Shaughnessy?

  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. My dad tells the 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, and they would say, well, Mr. IA, you know, I cut his hair and he put my kids through college and bought me a house, or Mr. IA did this or this, this. And we didn't even know where it went. And I have benefited from this tremendous history of business success in my, in and around my family forever. Whereas you came from a very different set

• 29:17Patrick O'Shaughnessy?

  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. You're fond of saying the story of the father and the son are, you know, are the same. And it takes tremendous.

• 29:43Patrick O'Shaughnessy?

  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. 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. 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.

• 30:26Patrick O'Shaughnessy?

  And so what is your principle or why? 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.

• 30:39Speaker 02

  I think there's a lot of times, I really resonate with you said when you were, you found that book and you're like, you know, this paragraph, this sentence just like hits you with like a hammer to the face. This is also like, you know, 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 fast. Like, I'm not speed reading here. I think I want understanding. And like, I want understanding of how things actually are, not how humans say they are. And humans, not only are we lying to ourselves constantly, which if you're lying to yourself,

• 31:24Speaker 02

  like, of course, you're lying to other people about like, why you're doing what you're doing or what you're doing, what it is that you're doing. And this is why I like autobiographies and biographies 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, like, I have no, I'm not incentivized to lie. And like, here's the stuff I went through and the trouble with whatever, being, what kind of dad you are, trouble with women, trouble with business, which you realize like, there's nothing that you're experiencing that somebody else hasn't already experienced. And so what I want is like, true understanding of like 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.

• 32:09Speaker 02

  It's like about you. And I think this, I don't think this is me. I think like 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, like I'm in the middle of this right now. We were just having lunch upstairs. And, you know, essentially like I'm just like in the middle of like trying to find the story that I want to tell with this book that grabbed a hold of me for six months. And I told you about, this is Bruce Springsteen's autobiography. I'm not, I don't even listen to his music. And I told you about this right, like right when I was like, there's stuff in this book that like this dude looks like he crawled inside of my mind.

• 32:53Speaker 02

  And like, especially in regards to how he views his work and the impact that it has on it. It's like, that is not a sentence. That is not a paragraph. That is like, that was made for me to read this at this point. And it's insanely powerful and to the point where like, it's like a drug. You know, I told you like right away. You, again, I need to like give you credit. We'll go back to this drug and understanding because like, I think this is really important about like people understanding why I want to talk to certain people and why like I was freaking adamant and like kind of pushing you on this. And we rescheduled a few times and like, I wouldn't be doing this if it wasn't for you. Not only because the, the platform that you gave founders, right?

• 33:35Speaker 02

  The podcast, then that crazy episode that we did together, which I think is like, we're never like, that was like lightning in the bottle. It was, yeah. It's Invest Like the Best, the, the title is Passion and Pain. And, you know, people are always like, oh, like, did you guys sketch this? I was like, no, Patrick doesn't sketch things out like that. He's like, I, we built a friendship. I want you on the show. Like, I don't think you told me anything we're gonna talk about. I do remember you texting me a few hours where you're supposed to do it like 10 a.m. You're like, hey, I got pushed back. Can we do 1 p.m.? I'm like, oh, no, my brain only works in the morning. So I took like a quick power nap and I'm in this booth. 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 all in these offices and I had one.

• 34:18Speaker 02

  They came and delivered to my house and 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. And then we just had the conversation and you know, that was like 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're like, you should be recording conversations. You should be recording these conversations. What are you doing? And I was like, no, no, it's distraction. I don't want to do it. I don't want to do it. And then, you know, I've told the story a bunch, but I think like it's really important. We're like, 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.

• 35:03Patrick O'Shaughnessy?

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

• 35:06Speaker 02

  Cause I'm not.

• 35:07Patrick O'Shaughnessy?

  I just had this four hour lunch with someone.

• 35:08Speaker 02

  Yeah, cause I'm not interested in superficial at all. Like, I met, I can't tell you who it was. I just had dinner.

• 35:16Patrick O'Shaughnessy?

  How long was it?

• 35:17Speaker 02

  I'm gonna tell you right now, but it was an incredible dinner the first time we met. And, you know, 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 just, I have no, 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 like warmed up and like feel the person out. 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 gonna, you know, relive, but like me and you just had an insane two and a half hour conversation at, in Tel Aviv. At like. Two in the morning. You know, that to have that level of honesty in conversation,

• 36:02Speaker 02

  like you would have to have like years of like getting to know somebody. So I do think.

• 36:07Patrick 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. Like you shouldn't just want to live like person X, Y, Z. 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 like screw base rates. I don't care what the I never care what the base rate is. Like the whole, the most interesting stuff is outliers by definition. So I don't care what happened to everybody else. I don't care if, you know, there's common pitfalls. Like, I think it's important that people take their, 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.

• 36:52Patrick O'Shaughnessy?

  Like, that's, that's been the search.

• 36:54Speaker 02

  I think it is for myself. You are interested in other people and frankly, in a way that I'm not. And I've seen, it's like very real and it happens every time we're with other people together. I'm like, oh, he like actually wants to know. Where like I am on the search of like, how the hell do I not have a terrible life? This is why I think the skill set that gets you to where you are, like so many people plateau. And like, I'm not, I'm not interested in plateauing. Like, I'm not interested in, you know, mailing it in. Like, I'm interested in, I want to get to the end of my life. Like, I don't want to tap dance on a giant reservoir of potential. I want like, there's, there was nothing more that I could have possibly done with my skill set and everything else. Like, I want to figure out how to get the most out of that. And this is, there's something you just said about like, there's a line in this Bruce Springsteen autobiography,

• 37:36Speaker 02

  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 is in a, in a 400-page biography of somebody. What you're going to realize is just like, 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 you mean, me and you always describe founders, like, it's church. It's church for entrepreneurs.

• 38:06Patrick O'Shaughnessy?

  In that church, I think the animated, interesting question is, you read these stories, all of which, back to my, my idea of originality, hardship transformation, you know, best story wins. That originality is, you're inspiring people to wonder, what's my thing?

• 38:24Patrick O'Shaughnessy?

  Everyone's got something, I guarantee it. Like, 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. 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, like, nothing meaningful is easy. And that's fine. And then, once you learn that, I think that's when it gets really fun, is that the...

• 39:08Patrick O'Shaughnessy?

  I always, I always have this feeling, 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.

• 39:36Speaker 02

  I, I think when I say this, like, what is my organizing principle? It's like, I want to understand things, or I want to understand not things, I want to understand people. And to understand people, you have to, like, go deep and like, what happened, like, where were you born? What was going on? Like, what was this experience like? You have to just spend a lot of time asking them questions and having these, like, 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, you know, at least a hundred hours of conversation, you know, on, on the low end.

• 40:05Patrick O'Shaughnessy?

  You mentioned, you said organizing principle.

• 40:08Speaker 02

  Yeah.

• 40:08Patrick O'Shaughnessy?

  Which, I think it's, I think that's correct. Just to push, because this could 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, for other people, not for yourself. It's not about you. And that's what makes the idea so powerful. I agree that that's your organizing principle. That's like, 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.

• 40:54Patrick O'Shaughnessy?

  Which is the most fun and rewarding experience of a lifetime. And I remember the little opening quote, you know, 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, you know, 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. I think what we all want is to make, participate in the act of creation

• 41:37Patrick O'Shaughnessy?

  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, that's gone, that's 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 the show.

• 42:13Speaker 02

  I think like one of the biggest things I want to avoid is like finding the thing, doing the thing, being great at the thing. And then like something you do causes that to stop. Where like, you know, I'm kind of obsessed with like the sustained success. You know, like I don't want to, you know, have this huge spike. I don't want to flame out. Like I'd rather just do like the slow build decade after decade, get better and like keep doing it. This is why essentially I read fiction and I read biography. Like that's basically what I read. And like the biography part is like, okay, what happens after they got what they wanted? And the conversations I've been having, a lot of these have been having on camera, but after, off camera, I'm always asking, because most of these people are older and more experienced

• 42:57Speaker 02

  and obviously more successful, smarter and everything else, just like, what do I have to worry about? Like, what am I not seeing that could like cause me to stop? Like, I like what I'm doing, I love it. What am I doing that would cause it to like, for me to not be able to do that? And there's like interesting like human questions about this.

• 43:15Patrick O'Shaughnessy?

  Well, the trap is.

• 43:20Patrick O'Shaughnessy?

  Before you do the work to figure out the thing that makes you feel alive,

• 43:25Patrick O'Shaughnessy?

  there's this great line in the Upanishads that it's always referred to abiding joy, like joy that doesn't, 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. I think those, those things are huge traps because they be, once you start to get one, it's the thing you start chasing.

• 44:06Patrick O'Shaughnessy?

  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, that, 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 like, 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, it's when we get sucked and I've of course have, just like everybody else, like 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.

• 44:46Speaker 02

  You're over fame, though. You don't like it.

• 44:50Patrick O'Shaughnessy?

  Yeah, I don't. I, I don't. I think it is, uh, I wish I could do what I do. And you know that thing in Men in Black where they, where they flash you in the face?

• 45:02Patrick O'Shaughnessy?

  I wish like at the end of each of my episodes, like flash people in the face and they forgot who I was and they didn't recognize me.

• 45:08Speaker 02

  I've been thinking about this lately. It's like, What I actually, you're limited, you have limited time that you're like every day like what it would, where do I like 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, like we can't do anything else. But other than that, like if you look at like 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 like having really strong relationships with other people. And like, I was not like that 10 years ago.

• 45:49Patrick 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. And during that time when I had lots of health problems, I ate unbelievably well. I worked out every day. I did all, I did everything you're supposed to do.

• 46:24Speaker 02

  Yeah.

• 46:25Patrick O'Shaughnessy?

  And, and then some, I was crazy about it. I kept daily logs of all this stuff, like there's nothing I didn't try. There's no willy foo foo thing that I didn't, 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, like I'm just one of those people that's going to be sick in life, like that's just how it's going to be for me. And it cannot be 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.

• 47:08Patrick O'Shaughnessy?

  I'm not arguing with the three, the three key things, but I found that an interesting experience in life. The body keeps the score.

• 47:15Speaker 02

  The fame part is interesting because this is something that like you uniquely understand and I can talk to you about. It's like, it's not to be known for the sake of being known, like these like reality TV show people, that's weird. Like I want. My work to be so good that it can't help but like become known and like talked about and like spread because they find value in it. This is just human nature. Like if you find value in a song, a movie, a book, a podcast, like no one keeps that to themselves. A restaurant, like we are compelled to tell other people about the things that we like. What I would say is like, the reason I think I view it differently than you, and you could tell me if I'm wrong or whatever, it's just like, not even wrong, but like, it's the relationships that you get to build as a result of you being easy to understand to other people.

• 48:00Speaker 02

  So like, no one's gonna stumble upon any of my work and be like, what is this guy actually interested in? Like, it's like very...

• 48:06Patrick O'Shaughnessy?

  Quite clear.

• 48:07Speaker 02

  Yeah, it's quite clear, very obvious. And then if you think there's like some kind of like, uh, unique insight, but my, my point being is just like, I think this comes down to a principle of like, all, like, why are people, all the people that I've studied, either had a conversation with or, or, um, or read about, it's like, 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.

• 48:33Patrick O'Shaughnessy?

  Of course.

• 48:34Speaker 02

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

• 49:03Patrick O'Shaughnessy?

  Well, because of course, on your deathbed, that's what you're gonna be thinking about, not your 5,000 podcasts. You're not gonna lie there and think...

• 49:12Speaker 02

  But that's surprising to me, Patrick. Like, this is why I get this freaking Bruce Springsteen book, 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, now he's like 76, and I just heard him on another interview talking about it, where the first half of the book is like, this guy, like, has one of the most insane work ethics that you've ever, ever seen. And it's channeled into one thing, and he has no doubt since he was 15 that this is what he's gonna do. And he realizes that he does not have the skillset, or he has all these things that he has not developed the skillset to handle. Like, I'm just gonna like, try to like, explain this.

• 49:53Speaker 02

  I mean, just record a whole podcast about it, so maybe, like, 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. It is important." And his biggest struggle was, he becomes famous. This is what Jimmy Iovine told me, because like, I got to meet him,

• 50:35Speaker 02

  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 Delivery Me From Nowhere. And I thought it was gonna be like a biography of his life, that's not what it's not at all. It is like a dark, I was shocked, dark movie. This is the key to understanding. Unbelievable, like, terrible environment born into. You're gonna, there's gonna be two actions there. You're just like, "This is what life is, I'm gonna 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 wanna live like that." My, 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,

• 51:20Speaker 02

  now he's, everybody knows who he is, he's world war fa- worldwide famous, he's rich, everything. 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 what he, this is what it goes by, I think I told you this upstairs, or maybe I even mentioned this, it's like, I 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. 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 is that his parents had so messed up his emotional well-being.

• 52:05Speaker 02

  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. And he was even writing, he has a whole album fantasizing about this before he's able to do it. And what he would run into the same thing where like, he, it's gotta be such a crazy juxtaposition of like, he's onstage in front of 40,000 people, they all love him. And yet, like 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, they'd have, she'd have feelings for him back, okay? Then he immediately goes, why do you love me?

• 52:50Speaker 02

  Like, I am so fucked 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 he'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. And then he winds up meeting the woman, he's married by the way. He winds up meeting another woman who's in his band and getting divorced because he realizes like, this is the person that can, like, I'm willing to do the work necessary to fix. Which is like a crazy thing. And then he goes through 25 years of therapy and in some cases, he has to get on antidepressants.

• 53:32Speaker 02

  And like, he's unbelievably honest from what took place, it's like from 35 until 67, when he's writing his book. And so, I think there's all kinds of lessons in there from personal. Like, what do you actually want in your personal life? Like, the kind of relationships you want with friends, romantic partners, whatever the case is. But this is what I meant about like, 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. Like, we have a million conversations, 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 fucking trust anybody. Like, that's obvious, like, why that is. And I do think I'm like, getting better and better and better to like, even the stuff me and you talk about, like, 10 years ago, there's zero chance I would have let that come out of my mouth. Zero.

• 54:18Patrick O'Shaughnessy?

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

• 54:23Speaker 02

  I know.

• 54:23Patrick 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,

• 54:37Patrick O'Shaughnessy?

  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." Like, who gives a shit? Like, 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 I, like you, and like 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.

• 55:15Speaker 02

  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 like, like the conversation I've had with you, with Sam Hinkie, it's really important. It's like, I'm getting to the point where like, 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. Like, 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.

• 55:46Patrick O'Shaughnessy?

  Yeah, the clean fuel, dirty fuel debate is really interesting. And look, a lot of, many, most, 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, you know, success, but having... People that could count on me, rely on me, I was faithful to, that I was loyal to. Like, 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. Like, working backwards from what you hope is

• 56:28Patrick O'Shaughnessy?

  true is a simple heuristic for finding what to do well. And I think, yeah, I think I can't wait to read the book.

• 56:35Speaker 02

  This is why I think, you know, reading a bunch at the same time, or not same time, but like, having a lot to pull from, is like, I'm reading the Bruce Springsteen book, but then you realize, like, 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. Took him a while to figure it out, but like, he got on the other side of that, where LBJ never did. And even though their source is very similar, like, there's a great story that Robert Caro tells in one of his books, where like, you know, LBJ finally gets to Washington. I think he's like a intern. I don't even remember what the job he has.

• 57:17Speaker 02

  He has no money, it's cold, and it'd be like, the sun would be coming up at like 5:30, and this woman that worked with him would always see him, like, running everywhere. And they just assumed, oh, he's got no coat, he got no money, he's like, 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 like, of course he was running. He like, finally made it to the spot, because he was talking about, he wanted to be president since, like, third grade or something. He's like, he finally made it to the city, to the spot of where all his dreams are. And like, he was going to run after his dreams. There's so much in between these two stories. One guy's a rock star, one guy comes to president of the United States. And it's the same thing.

• 57:58Speaker 02

  One is generative, one is unbelievably manipulative, and, you know, probably not a guy that you'd, like, want in your life to be around. And so I think also, learning from, like, great examples, but almost like, seeing like, oh, I don't want to be that way. This is like, something that, you know, one of the best things about, like, our friendship is like, I actually want to, like, let people in. Like, I want to have

• 58:20Patrick O'Shaughnessy?

  Of course.

• 58:21Speaker 02

  Friends, and like, deep friends. And in the past, like, that wasn't an important, like, thing to me.

• 58:26Patrick O'Shaughnessy?

  Agreed.

• 58:28Speaker 02

  This conversation is now therapy for Dave. But this is my, this is my point was like when I wanted to sit down with you, like there's a bunch of things I want to talk about, but it's like, I also want to like, kind of like talk about the stuff that like we normally talk about. The reason I think it's important for like me and you too is like how much of our ideas actually came from the creation of the podcast. Like you think about like 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 like we're like a professional learner, you know, like you, 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 like, who do you let like influence your, the way

• 59:13Speaker 02

  you think?

• 59:14Patrick O'Shaughnessy?

  I mean, how long you got?

• 59:18Patrick O'Shaughnessy?

  I, I could easily rattle off 50 people.

• 59:22Speaker 02

  Let's take one, like just some of the most important ideas and where they came from.

• 59:27Patrick O'Shaughnessy?

  To take the simplest example possible, in the early days of the show, this is a very like practical, real world example.

• 59:37Patrick O'Shaughnessy?

  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 Chathin Putigundat 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'd never built software before. I had an amazing team at the time that, you know, was able to pull it off. But the direction of the resources and what to do strategically just came from asking

• 1:00:23Patrick O'Shaughnessy?

  You know, those three are 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, you know, three people. Did you have all three on your podcast? You're two out of three. I've never met Brett. Okay, so you have two out of three. These ideas came from conversations that you had on the podcast? No, the, 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 Chathen the demo, you know, 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.

• 1:01:06Patrick O'Shaughnessy?

  He was just doing it out of, you know, just the goodness of his heart, I guess. And same thing with the others, just, and the three, there's many, 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 Chathen several times and Daniel sometimes. Your finance team isn't losing money on big mistakes. It's leaking through a thousand tiny decisions nobody's watching. Ramp puts guardrails on spending before it happens. Real-time limits, automatic rules, zero firefighting. Try it at ramp.com/invest. As your business grows, Vanta scales with you, automating compliance and giving you a single source of truth for security and risk.

• 1:01:50Patrick O'Shaughnessy?

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• 1:02:22Patrick O'Shaughnessy?

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• 1:02:35Speaker 02

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

• 1:02:51Patrick O'Shaughnessy?

  Yeah.

• 1:02:52Speaker 02

  You try to email the Aman in New York and ask them if they may 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 like, 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, where 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?

• 1:03:28Patrick O'Shaughnessy?

  Yeah.

• 1:03:30Speaker 02

  What about like, larger things in your life? Like, who do you think had like, an impact, like a, my life would not be the same if not for that one conversation, that one idea with that person?

• 1:03:41Patrick O'Shaughnessy?

  Two people came to mind right away.

• 1:03:45Patrick O'Shaughnessy?

  The first is Herb Allen from Allen and Company, who I don't know well. These lessons came from one incredibly, you know, incredibly interesting conversation about, my sense of him, again, don't know him well, is that he is uncompromising in his values. He does, he's maybe like, the apex predator of like, 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, I won't tell the examples, but like, I think willing famously to like, throw away huge commercial opportunities

• 1:04:28Patrick O'Shaughnessy?

  just because the person wasn't who he wanted to support. So 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 Dukka, who's been, who's very, very private. And, you know, there's no content about him or interviews with him. I wish to God I could, he would let me interview him. I know, I know he never will, who has been incredibly impactful on, at like, a philosophical level. He has, 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,

• 1:05:09Patrick O'Shaughnessy?

  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, you know, the feeling of aliveness. Like, 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 Berrudi, who I, I'm 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 what, he's like Reece, he's completely uncompromising in the most principled way of

• 1:05:53Patrick O'Shaughnessy?

  living I've ever seen. Just like, refuses to get sucked into the, the game. And I could, God, man, I could rattle off names for, for hours and hours. I mean, there's so many, so many people that have influenced me. And that's what makes this all, that's what makes what you and I do so fun is. I'm inspired constantly. And you're doing this new show. I interview people once a week, but really I interview like 10 people a day. That's what I do. I just happen to have mics there one of the times. You know, 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.

• 1:06:38Speaker 02

  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 a kind of an outlier and you just ask like, what the hell is going on with this person?

• 1:06:47Patrick O'Shaughnessy?

  Yeah.

• 1:06:47Speaker 02

  And you just keep asking that question to try to get like deeper and deeper and deeper. Well, like reverse engineer of what they're doing and like why they're really successful. There's another fascinating thing where like everybody, there's like this meme where it's like, everybody has a podcast now and everybody starts podcasts. And as soon as that like takes hold, you've been doing podcasting for 10 years. And you decide, no, I'm going to go in a different direction. And 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 that was like, they were like really well written, kind of like doing my job for me.

• 1:07:27Patrick O'Shaughnessy?

  Yeah.

• 1:07:28Speaker 02

  Why did you decide to do that?

• 1:07:31Patrick O'Shaughnessy?

  I'm in the abstract, very interested in how can I create and control valuable scarce units of attention? And then dole those things out to the people that we believe in. At a very high level, the reason we now have a magazine, which on its face, I think was as everyone would have 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? Well, the reason is, I think it's just in a beautiful way to shine the light beyond like podcasting on people that we admire.

• 1:08:14Patrick O'Shaughnessy?

  And to teach someone, teach the world about a compelling founder, or a compelling investor, or artist, or whatever. And the thing that I didn't realize 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 this, his compilation of his favorite New Yorker profiles. There's this line that says, "The best profiles over the last hundred years are defined by

• 1:08:57Patrick O'Shaughnessy?

  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, I want to read, that's what I want to read. And, you know, so I went and I read a million profiles, and the very best one I read was in a publication called Tablet on Palmer Lucky from Andorl. And I reached out to the author, his name is Jeremy Stern, who's now the editor in chief at Colossus. And, you know, the rest of that story is sort of history. He joined, we've got other people, you know, that have joined or are joining to write these profiles.

• 1:09:38Patrick O'Shaughnessy?

  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. And, you know, the fact, the one that we wrote about Josh Kushner and Thrive was one of these like 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 forty five minutes into reading it and I was still reading about the Holocaust.

• 1:10:17Patrick 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. And I thought that was the coolest, most beautiful thing. I never would have, you know, so this, this project has become an excuse to, first of

• 1:10:58Patrick O'Shaughnessy?

  all, find more talented people, the writers, that we can support, which is great, see the, see the potential, you know, same thing we've been talking about over and over again. So now, 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, you know, if we tell the honest stories and, and, you know, we want to tell the hard parts and the, and the interesting parts. And it's been successful beyond what I ever could have imagined. 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.

• 1:11:41Patrick O'Shaughnessy?

  When we started Canvas, everyone said, I think, like, if people say something's a good idea, I always get a little nervous because if it's, 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. And I think that's what I would, you know, starting a magazine in two thousand twenty five, I think, falls in that category of, it 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.

• 1:12:19Speaker 02

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

• 1:12:22Patrick O'Shaughnessy?

  What, what specifically?

• 1:12:24Speaker 02

  Colossus being bigger than the podcast.

• 1:12:26Patrick O'Shaughnessy?

  Of course.

• 1:12:27Speaker 02

  That's not an of course thing. You gotta unpack that. You gotta 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. Like, they're like, this is the best, you know, business interviewer in the world. And this is incredible. Like, why would he not want that to be the biggest thing?

• 1:12:46Patrick O'Shaughnessy?

  I'm not saying I want to keep doing that.

• 1:12:48Speaker 02

  I know you, I know that.

• 1:12:49Patrick O'Shaughnessy?

  For sure. I love it.

• 1:12:50Speaker 02

  But I think in your heart, if you had to choose, you'd be like, no, I'd rather have the profile to be bigger. Because you like, again, this goes back to, I think, how we started the conversation. Like, I really do believe you'd like to be the guy behind the guy.

• 1:13:01Patrick O'Shaughnessy?

  That's true, but the reason for me is like, 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, 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. Like, 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 report on an investment created by my incredible team on that side, who in many ways are just doing turtles all the way down.

• 1:13:39Speaker 02

  Yeah.

• 1:13:39Patrick O'Shaughnessy?

  It's the same, like, 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. I hope that they, I hope it gets bigger and bigger. And I don't want to like 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.

• 1:14:23Patrick O'Shaughnessy?

  I get to do this thing that we love to do for more people and point this, point the light that we're trying to cultivate on more and more talented people. That, that's like unbelievably exciting. I hope it's not just writing. I hope it's documentary. I hope it's, who knows where it goes. I hope we start convening people in small situations where, meet this person, 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. And so, yes, I would vastly prefer that all the rest dwarf whatever

• 1:15:04Patrick O'Shaughnessy?

  I do, even though I hope what I do lasts forever and is big itself.

• 1:15:09Speaker 02

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

• 1:15:16Patrick O'Shaughnessy?

  Yeah, now everyone's launching a magazine and it's gonna be like podcasts.

• 1:15:19Speaker 02

  But not only that, like specifically profiles, where like, people have been reading, like you just mentioned it, I bought that book too that you told me about, The New Yorker.

• 1:15:27Patrick O'Shaughnessy?

  Yeah, yeah.

• 1:15:27Speaker 02

  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.

• 1:15:43Patrick O'Shaughnessy?

  Yeah.

• 1:15:43Speaker 02

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

• 1:15:57Patrick O'Shaughnessy?

  From Dumb and Dumber, that's from Dumb and Dumber.

• 1:15:59Speaker 02

  But I don't know, I don't know what it's called.

• 1:16:04Patrick O'Shaughnessy?

  David, not an investor, podcaster.

• 1:16:07Speaker 02

  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 being the same vein as IBM or Microsoft. And so, he's like, the way I'm gonna do that is I'm gonna pick a fight with Bill Gates and Microsoft. And he does this huge fight. And originally, he thought that it was gonna 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.

• 1:16:38Patrick O'Shaughnessy?

  Of course.

• 1:16:39Speaker 02

  So it became billionaire A versus billionaire B, and it greatly elevated his profile. And then he said that Oracle and Oracle's products were risen, like came along with the increase. 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, anything else. You just, what were you thinking? Because like, that was something that existed forever, and who writes great profiles now? I don't even see any of them.

• 1:17:05Patrick 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 on to that, like, it should be different and really hard, like, really hard to do. And if I just, I'm sampling all the profiles we've written in my head, 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

• 1:17:50Patrick O'Shaughnessy?

  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 gonna do anything with it, just like, I'm just gonna, I just wanna start collecting the line. 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

• 1:18:30Patrick O'Shaughnessy?

  kinda 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. And I believe, 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 it's, it's, 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. It's the same thing

• 1:19:13Patrick O'Shaughnessy?

  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 like 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.

• 1:19:42Patrick O'Shaughnessy?

  I mean, the literal answer to your question is kind of funny was somebody I'm actually seeing in 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. 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. Like, people can't say no to a cover. And so I tested that theory out and it was true.

• 1:20:23Patrick O'Shaughnessy?

  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 literary spinning on like, oh, maybe we should, I would love to have a cover that I could dole out. Did that idea come before or after you read Jeremy Stern's piece on Palmer Lucky? Before. So I was, 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.

• 1:21:07Patrick O'Shaughnessy?

  An investor friend of mine, one of the, one of the, one of the great investors ever who's now retired. It was part of the Zoom conversation. And it was, the topic of the conversation was

• 1:21:20Patrick O'Shaughnessy?

  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, it's a cool idea. 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? If the invention is good, the inventor is probably good.

• 1:21:58Speaker 02

  Yeah.

• 1:21:58Patrick O'Shaughnessy?

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

• 1:22:25Speaker 02

  People vastly underestimate the importance of volume. 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. Where it was like this visit to Rick Rubin's house. And I'm a huge Rick Rubin fan. Like I, like I read a biography on him. I think it's like 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, it's like a 45 second clip that makes everything, like it just makes perfect sense on, on like, I needed to hear that whole three hour conversation just to get that 45 second clip and that 45 second idea, uh, in my head.

• 1:23:07Speaker 02

  But if you think of like, the guy started, you know, his, his record company in like 1984 in his dorm room. 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, that's, you, you worked with everybody. You've had a four decade long career. Like, why is that the case? Like, that makes me want to know more about that. Uh, our mutual friend, Brent Bayshore. Told me this hilarious story one time, you know, Brent Scott, he owns a bunch of different companies and sometimes those companies need a CEO and he found himself, I think, at like a lunch or dinner with Charlie Munger. And so he's like, you know, I'm this young guy.

• 1:23:52Speaker 02

  I think he was probably like 35 at the time. He said, I own these like 12 companies. How, you know, how do you and Warren find like great CEOs? And Charlie's just like, we just find somebody that is a great CEO and say, come do that for us.

• 1:24:06Patrick O'Shaughnessy?

  Yeah.

• 1:24:06Speaker 02

  And Brent's follow up goes, yeah, but what about hiring for potential? And he goes, we don't do that. It's a beautifully simple like idea. He's really good. Can you come do this over here?

• 1:24:16Patrick O'Shaughnessy?

  Yeah. Yeah, people show you. And it's that 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. I think he would call these breadcrumbs. Put stuff, put breadcrumbs out into the world so that people see it and are amazed by it. Like if you create a single thing, not, it'll be 10 things, just one thing that people are amazed by. Put it, 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.

• 1:25:01Speaker 02

  Yeah.

• 1:25:01Patrick O'Shaughnessy?

  One of your maxims. That's true. Great takes time. Great's hard.

• 1:25:05Speaker 02

  You just, you just proved this. The, 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?

• 1:25:13Patrick O'Shaughnessy?

  Yeah.

• 1:25:14Speaker 02

  We're gonna stop making music? We're gonna stop making movies? Like, no, it's just like, we need less bad shit, but that's always gonna happen. Like, there's always room for great. You just proved this with the profiles.

• 1:25:22Patrick O'Shaughnessy?

  Yeah.

• 1:25:23Speaker 02

  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, Walt Disney, towards the end of his life, was very fascinating because, you know, everybody associates him with animation and Mickey Mouse and everything else. And yet, when he's towards the end of his life, he's asked like, what is the things that he's most proud of? And he said, and 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 Disney was his obsession. 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 like low quality.

• 1:26:06Patrick O'Shaughnessy?

  Yeah, sure.

• 1:26:06Speaker 02

  They were like kind of scammy because.

• 1:26:08Patrick O'Shaughnessy?

  Traveling carnies.

• 1:26:09Speaker 02

  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 like trashy. He's like, that's the point. Mine won't be.

• 1:26:27Patrick O'Shaughnessy?

  Yeah.

• 1:26:27Speaker 02

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

• 1:26:31Patrick O'Shaughnessy?

  Yeah.

• 1:26:31Speaker 02

  And he's just like, I'm just gonna take every single part of this and make it better. And then they remove the parts that don't make any sense. And like, that's a great filter for like finding, you know, new things to create in the world.

• 1:26:44Patrick O'Shaughnessy?

  By the way, I spent my twenties 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 like, this is happening in this weird, isolated way, like just me and my notes. I'm not talking to anyone about these books. And so I wanted to, 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 the saying, learn, build, share, repeat. And just like, do that until I die. And I believe in that. And so.

• 1:27:28Speaker 02

  It's still, wait, learn, build, share, repeat.

• 1:27:30Patrick O'Shaughnessy?

  Yeah.

• 1:27:31Speaker 02

  Still really good.

• 1:27:32Patrick O'Shaughnessy?

  Still works.

• 1:27:32Speaker 02

  Yeah.

• 1:27:33Patrick O'Shaughnessy?

  And it's, maybe that's my, that's my governing principle, probably, like you, you said before. And yeah, it's, it's an incredibly powerful loop to go on. But that 10 years of reading prepared me to be a good producer of profiles. Cause I've seen great, I've seen good, I've seen average, I've seen bad. My, my reps are very, very, very high. And that's another thing I always tell people, especially young people, is like, what is the thing where you naturally have a lot of reps because you just like it? And find some, build off that, because there's this learning by doing concept, like you get better at something just through being prolific in the thing.

• 1:28:15Patrick O'Shaughnessy?

  And most people have a thing for which they are naturally prolific. Even that, if that's following your sports team, or whatever it might be, like, what's the thing you just can't help but do crazy high rep count of? Probably that's a good clue to like where you could go build one of these compounding curves for yourself. And for me, it was read, 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, helped me build my business and sell it successfully, you know, and on and on and on. That led to, it led to positive some.

• 1:28:58Patrick O'Shaughnessy?

  And me building my business successfully in software got me to all of these people building early-stage companies, writing these small checks. Writing these small checks got me to this series A investment that caused me to create this new investment firm. Creating this new investment firm caused me to go invest in all these, you know, companies in a bigger way and be more impactful on them and their trajectories than I could have been on my own. The whole thing is daisy chained together because I loved reading fucking books in my twenties. And I did something about it and I started telling other people which ones I liked. That's what, 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

• 1:29:43Patrick O'Shaughnessy?

  that I just listed would have been on my sheet. I wouldn't have even known to think about them. My own experience has cemented my belief in this growth without goals. Like, I wanted to grow. I love the idea in weightlifting, Jeremy Giffen and I talk about it all the time, of progressive overload of like, always like a little bit harder, a little bit more, like, go to failure, go to failure, go to failure. But you don't, the beautiful thing about life is you don't know where that's gonna take you. I, God, I never in a million years could have predicted any of this crap. What's even more exciting is they don't, it doesn't stop. Something, some set of stuff's gonna happen over the next 10 years, which if I tried to make a goal as today, I would be unable to predict. It's gonna be so much fun. But it all started with, I had a thing I loved naturally. I just liked to read books.

• 1:30:28Patrick O'Shaughnessy?

  And I think that's profoundly cool. Now, you know, obligatory disclaimer that like, 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, I, I was very lucky, the situation I was born into in life with the parents I had and, you know, the, the, the things that were easy for me, I didn't have to pay for college, all this, all this stuff, made it possible for me to do these things. And I, I think that's important to acknowledge. But nonetheless, like, you found your way there, you found the passion, you found the high rap passion, and now look, now look. That's like my constant urging to people, like, it's there, I promise. There's something.

• 1:31:13Patrick O'Shaughnessy?

  Just go find it.

• 1:31:14Speaker 02

  I think it was beautifully said. We haven't even touched on investing, which I want to.

• 1:31:19Patrick O'Shaughnessy?

  Let's do it.

• 1:31:19Speaker 02

  I want to talk about, is it code red? Seeing red? What is, there's this fantastic story that we've talked about before, where you were gonna make an investment in somebody's fund. Is it seeing red? What did this person say about you?

• 1:31:37Patrick O'Shaughnessy?

  He said I was red on the color wheel.

• 1:31:39Speaker 02

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

• 1:31:41Patrick O'Shaughnessy?

  Sure. So you, you, me and Sam Pinky were walking, and I think you asked Sam, what's my biggest weakness or something?

• 1:31:48Speaker 02

  No, you were interviewing, okay, so. When you just said, like, this all started from, cause I, I like, loved to read, and then that started this whole chain of events, and now you have this other parallel thing that you just do compulsively that you can't help? Which is like, exactly what you said, I'm doing 10 Invest Like the Best episodes a day, I'm just recording, you know, I'm doing 50 a week and I'm just recording one? Like, if we're in a group, I know what's gonna happen, you're just gonna start lighting people up with questions. So we go on this five hour walk, which Sam did not like. People don't know that you're like a goddamn billy goat. Okay, like, I, it's just, you, 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, there's a mountain here, like,

• 1:32:33Speaker 02

  I'll follow the trail around it. It's like, no, billy goats just go straight over and up. 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, and that's like the best episode, except you're interviewing both of us.

• 1:32:48Patrick O'Shaughnessy?

  Yeah.

• 1:32:49Speaker 02

  And you would ask the other person questions about the other person. It was like, really, actually, 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 in heart, and is not trying to criticize you just for criticism. I think a lot of people are hypersensitive to criticism. And if it's like some random stranger, okay, that makes sense. But you know that person cares about you. You know that person wants the best for you, and they're telling this about you. You should, even if you don't agree, you should think about it for a little bit. And I've thought a lot about what he said in, 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.

• 1:33:34Patrick O'Shaughnessy?

  Red on the color wheel.

• 1:33:34Speaker 02

  There you go.

• 1:33:35Patrick O'Shaughnessy?

  Yeah.

• 1:33:35Speaker 02

  What does that mean?

• 1:33:36Patrick O'Shaughnessy?

  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. What I mean by that is, I'm often finding myself wondering, in a, in a situation, like, what would Sam think about what I'm gonna do here?

• 1:34:02Patrick O'Shaughnessy?

  I so value his character and judgment and fidelity and, and just so many things about him. But like, what a role to play in somebody's life. Like, he's the one I invoke in my head, one of three or four people that I invoke in my head of like, what would this person think about, you know, this thing I'm about to decide on? But back to the story, so, he said, uh, yeah, it was something like, what's my biggest weakness? And he, he described me as being red on the color wheel, which, uh, he explained meant that, uh, when I'm interested in something, I am intense, like, and I've always been this way. I am voracious and intense and aggressive. And, uh...

• 1:34:48Patrick O'Shaughnessy?

  I would say I have a skill at making things happen when I'm interested in them happening. And maybe that's one side of the sword. The other side of being red on the color wheel is this like locked in intensity. The other side of it is that like the moment that attention is focused elsewhere, I can tend to whiplash around a lot and change my opinion.

• 1:35:11Speaker 02

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

• 1:35:16Patrick O'Shaughnessy?

  Okay.

• 1:35:17Speaker 02

  Where like if Patrick is focused on you, he will 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, I'm like, we need to focus on this. I had to get in your, because you're, in some cases it's like a physical presence thing.

• 1:35:36Patrick O'Shaughnessy?

  Yeah, yeah.

• 1:35:37Speaker 02

  It's not just like, I can get you on the phone, but I was like, no, this is not good enough. So that's the strength, your strength can be your weakness.

• 1:35:43Patrick 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, everything is double edged, you know? Which is I have, if you close your eyes and try to visualize something, a red cardinal or something, there's, 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, 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?

• 1:36:12Speaker 02

  We were at Brad Jacobs' house having breakfast.

• 1:36:14Patrick O'Shaughnessy?

  Yeah, yeah, yeah.

• 1:36:14Speaker 02

  He was very disturbed by this and he tried to fix it.

• 1:36:16Patrick 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. 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 it wasn't the Eye of Sauron. That sounds so bad.

• 1:36:43Speaker 02

  But said in a loving way.

• 1:36:44Patrick O'Shaughnessy?

  I understand. So Sam's point was you're red on the color wheel and.

• 1:36:50Patrick O'Shaughnessy?

  When your attention shifts, it can be whiplashy for those around you. What was the example he gave, though? It's too good of a story not to tell. 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. Hell, yeah, I want to, of course.

• 1:37:22Patrick O'Shaughnessy?

  And told him the amount or whatever. And then he called me back like a month later and was like, OK, like I have the docs already and, you know, we're ready to go. And you're still in for this much? And I said something like, well, I can't. Yes, I'm still in, but I can't do that much because actually like I have also launched a fund. And he was like, what? And I said, yeah, you know, I need to make a GP commit to my own fund. And so I'm, you know, this is before I sold my business. It's a little bit, you know, tighter situation. And I have to reduce the amount. And he started to tease me because he was like, wait. So when I first called you a month ago, you had never even thought about having a fund. I've never heard you talk about that.

• 1:38:08Patrick O'Shaughnessy?

  I don't think you'd ever thought about it. And now a month later, like you already have a fund like a month later, like it's raised and done. And I think that's a good example of like, yeah, some opportunity came out of left field. There was this investment opportunity in one company that led to a fund very quickly in the summer of 2020. And 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. Like I don't want to whiplash people. And I realized, thanks to Sam, that I was whiplashing people. I would be so excited and willing and able to galvanize people around an idea.

• 1:38:49Patrick O'Shaughnessy?

  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. I don't ever think about stuff in the past, like ever. And so I not only can I change my idea, but I literally never think about that thing again, that I was so passionate about in the moment, you know, for a short period of time. And that is jarring for people, you know, that are like signed on to do a thing. And then a week later, you're like, what are you talking about? What thing? We're doing this thing. And so I've worked pretty hard to narrow the simplify my life with rhythm and harmony, focus on fewer things, like get less distracted by what I would call like the flavor of the month club, which is something that can definitely snare me for sure.

• 1:39:34Speaker 02

  Yeah, now that you say that, I haven't had any like eye of sorrow moments with you in quite a while. You've kind of fixed that. I heard Ari Emanuel on your podcast say something that was like actually pretty smart, where his like, his idea of like, especially when he's trying to do a deal, he like over communicates. 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 I'm like, oh, like, I'm like, having an issue, and we've never even had an argument or a fight. I mean, one thing that I love about it's like, we worked together for years and we had like, 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, like, it was just like exactly how I want to.

• 1:40:19Speaker 02

  I don't want to deal with people where there's like, 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 like, this is what we're gonna do, like, figure it out. But the, I think what was happening there is it's like, there's all this like, unsaid stuff that you think we are looking at on the same way, and yet if we just said, oh, like, this is how I'm thinking about this thing, and this is how I'm thinking about that thing, and like, just essentially just over, communicate as much as possible with the people that are important to you, because then you're not gonna have, there's no unspoken assumption, you know, and then if you let it sit there too long, then you have another unspoken assumption on top of that one, then things can get like, really, really weird.

• 1:40:56Patrick 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 journeys. So you're mostly or largely backing the person and the team versus the, you know, mature business story. And pretty important that that person's a good leader. And I think one of the things I underestimated about great leaders, that Ravi Gupta is another person that I would list, you know, and people that have really impacted me. At one point, I called like everyone I knew, I was like, define good leader, just, I'm gonna, I'm gonna do a survey.

• 1:41:40Patrick 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 Robbie's was my favorite. And what I've learned about what is shared in common amongst people that others want to follow. One of the big ones is that they are hyper communicative with those people. And they're consistent and they lead from the front. They, you know, they, they take risk, they take arrows for the team. They communicate like crazy with the team. If something's changing, they over communicate it, you know. They're, they're honest, like all these things add up to someone that people want to follow.

• 1:42:25Patrick O'Shaughnessy?

  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, I am so excitable, like when I find something new and interesting, like I just cannot get enough. But very often that means I'm billy goat-ing up ahead of the pack. And forgetting like, oh, wait, I, I need to like, there's 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.

• 1:43:00Speaker 02

  Some of the best leaders, like when you see in like company buildings, like history speakers, entrepreneurs, like you really think of them as like, they, they're teachers and then they understand they need to repeat, repeat, repeat. I always say repetition is persuasive. You gave me a great like Catholic saying where it's like repetition doesn't spoil the prayer. So I think like Jim Sinigal, 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. Jim Sinigal 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 like how influential this guy was and most people don't know who he, he is.

• 1:43:43Speaker 02

  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. And what he is is like, it means like teaching what our philosophy is, what is our purpose? How, 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. Like it's just nuts. And what I was shocked is even you think of, you don't think of Elon as like, 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 an 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.

• 1:44:24Speaker 02

  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. And I think that has to do with like over-communication. 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 gonna do it. And so I think about that like a ton, like, repeat, repeat, repeat.

• 1:44:49Patrick O'Shaughnessy?

  Yeah, the joy of that sort of thing and that sort of leader, the, 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. 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. Cause like now every goddamn meeting I'm in, like, I'm doing my life's work.

• 1:45:32Patrick O'Shaughnessy?

  And my experience is that almost nobody is doing their life's work. Even great, a lot of great founders, I would say it's not their life's work. 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. He 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. 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.

• 1:46:13Speaker 02

  Say that one more time.

• 1:46:14Patrick 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 take me, 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 a best story wins, originality, hardship, transformation. In the business context, it's I want someone that's lived a very unique path. I find success in startups is 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, you know, I think that's really important.

• 1:46:58Patrick O'Shaughnessy?

  Transformation is about the customer, you know? If you build something crazy hard, the customer's life will get way better service. So I think this powerful concept of life's work can be applied to ourselves to make great investments. And it's really rare, but these, the, the leadership qualities of like, like the reward for great work is more work. Reason I started talking about life's work and, and investing is these people realize, come to realize you will not be rewarded with great work if you do not become a good leader. And a common pitfall that I certainly have fallen in before is when there's someone really talented, they can do a lot themselves, they can get a lot done themselves. And I refer to this as like heroics. And that's always necessary.

• 1:47:43Patrick O'Shaughnessy?

  A founder always has the sort of, is the flame keeper of the spirit of the company. And, and I think founder led companies are so much, of course, so much more interesting, preaching to the choir here, than professionally managed companies for the most part. But I do think that like becoming a great leader becomes the most important way to secure more right to do great work.

• 1:48:07Speaker 02

  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 can, you admire personally that stopped?

• 1:48:23Patrick O'Shaughnessy?

  There's 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.

• 1:48:31Speaker 02

  But they're doing something.

• 1:48:32Patrick O'Shaughnessy?

  Yeah, I don't.

• 1:48:38Patrick O'Shaughnessy?

  I'm just wired this way, you are too. I just need to be doing something. I can't sit around.

• 1:48:45Patrick O'Shaughnessy?

  And so I'm drawn to people that are, that want to make stuff. And so I have tons of examples of people who have been,

• 1:48:56Patrick O'Shaughnessy?

  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, there's one investor that comes to mind, his name is John Pfeffer. And John has been wildly successful in like the, it's almost like he picks whatever he's doing and it gets to the tail end of it. He tries to find like the thing in the world that is the most different from what he's doing. He says with glee that require him completely abandon his current network because they're irrelevant for it. Like one time he went from being one of the key guys at KKR, and then went to be like one of the most important guys in cryptocurrency. And then 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.

• 1:49:41Patrick 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, I don't spend a lot of time with people that were prolific creators of things that just stopped.

• 1:50:02Speaker 02

  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.

• 1:50:12Patrick O'Shaughnessy?

  Here's an example.

• 1:50:15Patrick O'Shaughnessy?

  I love, 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.

• 1:50:31Patrick O'Shaughnessy?

  And and then you tear them up so it's just one, you know, one, one thing on each sheet of paper and then you have to in reverse order, ten down to one, slowly throw the rolls away until you're left with one. Okay, so one, one roll 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 ten? You could do this with attributes for yourself, too. Curious, hardworking, whatever, and then and then jettison those one by one. Fun game. I played this with my, my wife and my kids and my in-laws one time. And I'll never forget it. My, my father-in-law had a very, very successful career as an

• 1:51:13Patrick O'Shaughnessy?

  entrepreneur and executive in the kind of healthcare and insurance world. And we were, we were doing this game and his last one was grandfather. So that was like the role that he kept as his final, most important one. And he is an unbelievable grand, like, like the Michael Jordan of grandfathers. Like he is, he is unbelievably good at being a grandfather. It's like, makes me emotional thinking about it and so thankful for it. And the, the difference it makes in my kid's life and his other grandkids' life is extraordinary. And so Dan, is his name, Dan is no longer a major healthcare executive. He's still

• 1:51:56Patrick O'Shaughnessy?

  an entrepreneur. He can't, 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 the, in this case, in the role of grandfather. So I think that's exciting for my own life. That maybe when I'm 70, I, I won't do any of this stuff. And I'll do something else that's totally different, but my attitude

• 1:52:38Patrick O'Shaughnessy?

  towards it hopefully will be the same. And that will be because I've gotten the privilege of watching people like him do that sort of role at that stage of their life. So back to your original question. The people I love and admire most do pour themselves into what they're doing, regardless of what that role is, even as that role shifts around as life goes on.

• 1:53:01Speaker 02

  You gave me this term that we describe people that we don't want to spend time with, that now I think I just use and I make that I came up with it, and it's casual. It's like, you know, do you want to go to dinner with this person or do you want to meet this person? And like shorthand between me and you, we're always like, no, they're casual. Like, they're just not, it's the exact opposite. That's a beautiful story. Like, I, 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.

• 1:53:27Patrick 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?

• 1:53:42Speaker 02

  Bill Campbell.

• 1:53:43Patrick O'Shaughnessy?

  Bill Campbell. I never met Bill Campbell. I wish I had. It's this, this beautiful archetype of older guy from just working with a couple executives. And he worked with Google and 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. 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, 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, later stages of life when I think

• 1:54:28Patrick O'Shaughnessy?

  the ability to do something like that goes up. 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, the people that we all worship. In the business world, of course, I'm amazed by them too. But there are flavors of success. 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 shit will ripple through history. My son and my daughter will now behave differently because of the experience

• 1:55:10Patrick O'Shaughnessy?

  that Dan and my mother-in-law and my dad and my mom gave to my kids. So what's better than that?

• 1:55:16Speaker 02

  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 that you're gone. Somebody, we talked about this, I think yesterday. Somebody took a bunch of like interviews I'd done and stuff I've said on the podcast and like literally made like a hip hop album. And it was like eight-track hip hop album. I think it's called like David Sandler founders or something like that. And I, we keep talking about it, but I sent it, sent it to Hinkie. Cause the first one was like this idea of like general generational inflection point.

• 1:55:48Patrick O'Shaughnessy?

  Yeah.

• 1:55:48Speaker 02

  Generational inflection point, which is like the founder of the family. And you know, Hinkie's rather religious in a way that maybe I'm not. And you know, he's like, 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 about myself? Like, go on.

• 1:56:04Patrick O'Shaughnessy?

  I wouldn't put it past you.

• 1:56:11Speaker 02

  And so I was like, no. And, uh, you know, he's like, yeah, I listened to a bunch of them, but like that, that first song, he's like, that's obviously like a, that's a sign from God. You should consider it a sign from God. I'm like, what? What is this? And we were on the phone. I was like, what are you talking about? The reason that came to mind is just in that song. I guess I talked about, I think it was on your show where I was just like, you know, this, this, this choice by this man I don't remember and I never met. I met him, but I don't remember him, which is my grandfather, who is 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.

• 1:56:48Patrick O'Shaughnessy?

  Not here.

• 1:56:49Speaker 02

  Yeah, I don't speak the language. And like, that's just one choice. You know, three decades later, whatever, I'm gonna be born. And now I'm born in a, 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. This 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?

• 1:57:14Patrick O'Shaughnessy?

  The story was so overwhelming, I honestly don't remember. It was probably husband or father, one of those two.

• 1:57:22Patrick O'Shaughnessy?

  To me, those are the most interesting roles in life.

• 1:57:27Patrick O'Shaughnessy?

  You know, you and I, 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?

• 1:57:37Patrick O'Shaughnessy?

  And I hope it's, you know, I hope it's that till it's grandfather, I guess. But the, the available, we said, I said something like this earlier, but the depths available in those relationships are crazy to me. I can't believe that every couple of years, you, I find a new level of those things. I just can't believe, every time it happens, I'm like, I can't believe it's happening again. And in terms of like, a place that can yield rewards,

• 1:58:07Patrick O'Shaughnessy?

  those are the most interesting to me. But more generally, like, the, maybe this is the theme of our conversation today, that the, the set of, small set of relationships with people for whom I would do anything. And that's how I'm wired. Like, there's a certain category of person, you're one of them, that I, whatever you need. You need to explain it, like, I'll do it. And getting to that point with people, I don't think, life's too short and, 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.

• 1:58:51Patrick O'Shaughnessy?

  That list of people for whom I would do anything. Is my prized possession. 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, even if they don't feel the same way about me, that's okay. If I'm in their list of 50 and I'm 50, it's fine. Yeah, I think, I think that, that role game is quite fun because it, it, I think it pulls out of you like where you have the most energy.

• 1:59:22Speaker 02

  I think this, exactly what like 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 like, this is why I'm gonna keep holding on to 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 learned stuff about you that I did not know. 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?

• 1:59:58Patrick O'Shaughnessy?

  One is, uh, 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, um, I have cousins who are technically my like third or fourth cousins that feel in my family more like a first cousin. 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, as a young kid. I went to this giant high school in, uh, in Connecticut, like 4,000 students.

• 2:00:43Patrick O'Shaughnessy?

  And I just partied way too hard and didn't get good grades and didn't take it seriously. And so I, there was a day, uh, I remember very distinctly. I was at a friend's house having stayed up too late the night before. And I, my dad called me and said, hey, you know, you should, you should probably come home. There's a whole bunch of very small envelopes here from colleges. So I actually got, I 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. 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

• 2:01:27Patrick O'Shaughnessy?

  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. I met, they do, it's not like freshman year where you have all this amazing orientation. You transfer students, they're like, here's your room number, like, see you later. So I met like the couple other transfer students and that was it. And back to being shy, like I wasn't at the time good at like navigating a new social situation. I just, I 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

• 2:02:09Patrick O'Shaughnessy?

  upon himself to come meet me, find me. He, I remember distinctly, he brought me a fake ID. He, he went so out of his way for like the first six months to like organ transplant me into his social circle. And like maybe Tim owed me a beer or two, you know, a couple, a couple nights out and a beer was his obligation as a family member. But instead, he would like 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. 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

• 2:02:49Patrick O'Shaughnessy?

  groomsmen in my wedding that wasn't a family member. So, you know, through this act of over the top kindness of just, there's 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. 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

• 2:03:30Patrick O'Shaughnessy?

  Dame, the first bar I walked into, and she was the first girl that I talked to. And 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. I'm not, I'm not young anymore, I'm 40, but 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

• 2:04:14Patrick O'Shaughnessy?

  years with her where I didn't even have a fully developed brain. It's by far the number one blessing is that she, yeah, we created this, we have created this life together in a way that I, I mean, the thousand things that's 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 have happened and this life wouldn't exist. And so I love this story

• 2:04:52Patrick O'Shaughnessy?

  because, 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.

• 2:05:16Speaker 02

  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.

• 2:05:22Patrick O'Shaughnessy?

  Thanks, buddy.

• 2:05:24Patrick O'Shaughnessy?

  If you enjoyed this episode, visit colossus.com. You'll find every episode of this podcast complete with hand-edited transcripts. You can also subscribe to Colossus, our quarterly print, digital and private audio publication, featuring in-depth profiles of the founders, investors and companies that we admire most. Learn more at colossus.com/subscribe.

• 2:06:03Patrick O'Shaughnessy?

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