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

You have this almost obsessive interest in finding talented but not well-known or relatively unknown people. Then you essentially spend a lot of time talking to them, developing relationships, and putting all of your resources behind that person. What is going on there?

Patrick O’Shaughnessy

Mm-hmm.

And then you essentially spend a lot of time talking to them, developing relationships, and putting all of your resources behind that person. What is going on there?

Patrick O’Shaughnessy

Yeah.

What is going on there?

1. Championing Hidden Talent

Patrick O’Shaughnessy

Given 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 enjoy that. I’ve read so much and spent my whole life as a constant-learning-type person, so finding something fresh and new is very exciting to me, and you can usually do that with people like this.

I’ve 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, the wins that I’ve had—the things that, if you were to write a Wikipedia article about me, would be the accolades or accomplishments—I don’t care about those things. I don’t think about them. When they happened, they didn’t do anything for me, emotionally or otherwise.

For whatever reason, that’s just not what I enjoy. But when your success happens, or when many other people that my team and I have championed have a win, I feel that deep in my soul, heart, and gut in a way that is more gratifying to me than anything else in the world. This extends to my kids, my wife, my friends, the CEOs of companies that we’ve invested in, and people that we have on our show that we tell the world about. That’s the repeated thing that I love. I also like picking sides. I like saying I like this person and, by extension, I like them more than the other available options in this field or industry, and I get tremendous joy out of that. Now I’m architecting my life to be able to do as much of that as possible, and I hope I get to do it for a long time.

I screenshotted this text many years ago. Somebody was asking me—I can’t remember who it was now—what Patrick is like, and I wrote, “Well, Positive Sum is definitely a way to describe him.”

I wrote, “And he doesn’t do things for money.” That doesn’t mean he’s not commercial. He makes a lot of money, and he’s going to continue to make a lot of money, but that’s not the driver behind it.

Let me go back to one of the craziest days of my life, which directly involved you. I was in the middle of a five-and-a-half-year struggle of being obsessed with something I knew I truly cared about and thought was really good. But the external world was saying, “No.”

Patrick O’Shaughnessy

Yeah.

“Nobody gives a shit about what you’re doing, David.” I kept doing it. We have a mutual friend in Sam Hinkie, who’s going to keep getting annoyed because I bring him up on every podcast I go on.

Patrick O’Shaughnessy

He’s deserving of the mentions.

The 2 episodes he did with you, especially the one about “Find Your People”—

Patrick O’Shaughnessy

Mm. It’s a beautiful one.

I go back to that one all the time and to the notes that he says in there. One of the things I think about all the time—which, again, I’m not an investor—is that I want access, and I want deep relationships with very high-quality people. He’s like, “People are power law, and the best ones change everything.”

Once you actually see that, you are almost ruthless about who you let have access to you. I think I’m getting very ruthless and continuing to be ruthless because of what I’m chasing after.

I had no followers on Twitter at all, just tweeting into oblivion. No one gave a shit about what I was doing. One day—this is why it’s one of the first things that speaks volumes about you and how you actually live your life, and why I think you’ve leaned into this more over the last 4 years we’ve been talking—I saw a bunch of notifications on Twitter. I don’t get notifications on Twitter. What is this?

Patrick O’Shaughnessy

Oh, that’s funny.

Yeah. The only time I used to get notifications was from a guy who had my name and was a Brazilian MMA fighter. When he would fight, all the tweets were in Portuguese. I don’t know what they’re talking about. It’s not about my podcast.

I almost remember it verbatim. I should go and see how much of the text inside the tweet I can get correct. You wrote, “I never find new podcasts to listen to. I think David Senra’s Founders podcast is excellent. You should listen to it.” You linked to an episode on Estée Lauder.

Patrick O’Shaughnessy

Mm.

It’s one of my favorite ones.

Patrick O’Shaughnessy

I love that episode, yeah.

You sent me a link. At the time, it was a paywalled podcast because I couldn’t figure out the business model—I had no listeners. Back then, I would get an email every time you had a new subscriber. There weren’t many emails coming in every day; I could count them on 2 hands. The first thing I did—well, the next day, I logged into my email, and it was just—

Patrick O’Shaughnessy

A wall.

Whoosh, all the way down. But that is such an unusual instinct. If I’m being honest, I don’t think I would have done that. What the hell is going on there? You didn’t see it as a competition. What was happening?

Patrick O’Shaughnessy

The first thing that flashes to my head is that, on my show, I’ve always asked people the same question at the end: “What’s the kindest thing anyone’s ever done for you?” Some person on Twitter went and compiled every answer. There are 500 answers or whatever, categorized them, and made a pie chart of what people say.

Something like 2/3 of the answers to this question were the same: The kindest thing was that someone made a bet on me before I deserved it.

Or they saw something in me that maybe I didn't even see in myself. They bet on me before others would, and that was the answer to the question—the kindest thing.

When I was 26, I became very interested in all of the world's religious texts. I studied philosophy early in life, and I've always been interested in that stuff, but I was in a weird spot in life. I hadn't found anything to do yet, I wasn't that good at anything, and I was searching. I was always searching for, “What the hell should I do? What the hell's the point of all this?”

I found this passage in the Upanishads, which, as a book, is probably the most important book to me. The Upanishads is a collection of stories from many thousands of years ago that were oral, passed down orally through generations and then eventually written down. I remember being struck by this one passage; it literally felt like someone had hit me in the face with a hammer. There's a line in this passage that basically says something like, “Those who feed the hungry protect me. Those who don't are consumed by me.”

It felt like there was a moment of understanding that happened in my head. Up until that point, from the middle of my teenage years, I was this nice, sweet boy, and then I got kind of hardened and went through a period of life that was tough. It just woke me up: 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.

I think it's interesting that that's probably the thing that most informed my worldview, and then the answer to this question that I love to ask is predominantly that someone bet on me. As I told you before, the thing I love more than anything is seeing the potential in somebody before everyone else and then helping the world see what I see. If I could do one thing over and over and over again for the rest of my life, it would be auditioning people to see if there's something that I see that no one else sees, and then helping 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.

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

You said before you were chasing something, right?

Yeah.

2. Growth Without Goals

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 know 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 called “Growth Without Goals,” so I'm not chasing any particular thing.

I don't have a big, hairy, audacious goal or something like this. I don't want to put someone on Mars like Elon Musk, and I'm not saying 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 Bret Victor, and he espouses this idea that you should find a principle that you want to pursue. His principle was that digital creators should have instant feedback with their creations. 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 to collapse that gap.

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

But you're one of the few people in the world who have actually identified this organizing principle and then built a wonderful business around that.

Yeah.

And I see the media and investing as not two separate things. We've talked about this a million times, but they're the exact same thing. If you actually know Patrick and what is important to him, they are the exact same thing.

It's taken me a long time to articulate that principle—a decade—and that's okay. Don't get discouraged if you don't watch Bret Victor's talk and can't name your principle an hour later. 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. It becomes universal.

On my team, for example, we're 16 people, something like that. This is how I think about my team: Who can I find and see something in, bring them in, and then make their career explode, hopefully in an amazing way? It can be investing. It can be just in friendship. It can be on your team. 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.

I have no idea where it will take us. That's the other fun part. One of the reasons I don't like goals is I think very talented people, when they set a goal, tend to do it, and that's why goals are interesting to lots of people: 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. You know the road in front of you, and you have blinders on. I don't actually like having blinders on.

Everything that's ever worked for me has come out of the periphery. Sam Hinkie texted me about you. I wasn't looking for a podcaster to promote. You were not the result of some goal that I was seeking. You were just something that came out of left field, and everything interesting I've ever done came out of left field. That's why I don't keep long-term goals or short-term goals. I'm very open to opportunity along this principle, and so I'm very enamored of this idea for how to live.

At what age did you stop having goals?

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

My dad, when I was 21, handed me this book of letters that he had been writing to me since I was born. A lot of them were from when I was a baby. 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. Now I do one every year, on his birthday, and things like this. I'm going to give him a packet of letters as well when he turns 21.

I remember starting this process of wanting to write him a letter before he was born, and it got me wondering about what good parenting is. What do I want to do as a dad? I believe deeply in showing, not telling. I think maybe that's another reason I don't like being interviewed.

I don't like telling. I'd rather just set an example. But I was thinking, “What example do I want to show Pierce?” I don't remember my exact chain of thinking, but it ended up in this idea of everything I just talked about.

So it was born of wondering, what example do I want my son to see and emulate? I'm sure you've learned this about kids as well: They don't do what you tell them. They do what you do. They just copy you. And so how you behave is how you parent, and I was thinking about that at age 28 and wrote this thing. That's where it came from. Right around then is probably the first time I thought about it.

How long was it from age 28 until you realized, “This is going to be the simple organizing principle of how I'm going to live my life and spend my time”?

I actually don't think I could have articulated the principle as I just laid it out until very recently. I could have told you about the power of Bret Victor's “Inventing on Principle” starting 10 years ago, or whenever I first saw it, but I would not have been able to articulate the principle to you cleanly, and that's because it's hard. For whatever reason, it's really hard to pin this down.

Interestingly, I've never met Bret 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. I took his principle—not my own, but his principle of instant feedback—and applied it as the primary design principle to software that I built in my last business, which worked really well.

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. 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.

3. The Feeling Of Aliveness

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.” It's like, no, life is meant to be experienced.

Mm.

And I find that in myself. I do think—I can't explain. I have a really woo-woo part of it. I always just say that line, and you laugh. But I have this really woo-woo part of it. It's just that I go off feeling, an intuition for a lot of things that I do, and I don't want to have to describe why I believe this to be true, why I want to pursue this path, or why I think this idea is interesting. I think it's just something inside of me that language cannot describe.

I don't know if it was Alan Watts who said this. He had such a way with words that maybe it was him. It might have been Joseph Campbell. But something to the effect of, “We're not searching for the meaning of life but for the feeling of being alive,” and I think that's correct.

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. People know what it's like to feel alive. They can call to mind these moments in their lives where they felt the most present and alive, and using those as a signpost to what your principle might be or what you should be doing, I think, is a really great thing.

I remember reading that line 15 years ago as well, and then I started to chase the feeling of being alive. It wasn't a goal, but just that feeling. Everyone can answer this question, by the way. It's a really great way to have a conversation with someone: Ask them where they feel this and then also why they're not doing more of whatever the answer happens to be.

It's a funny circumstance of humans that they kind of know what makes them feel most alive and then they don't do it most of their lives.

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

Usually, it's simple: fear. It's fear that by pursuing an original path—I have this idea that the best story always wins—and I spent the last couple of months really trying to figure out what I think “best story” means. The best principles for a great story that I could come up with were originality, hardship, and transformation.

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

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?

It definitely helped me find it because I wanted to not waste life. When I was a little kid, 5 years old or whatever, I had this crippling fear of death. I remember my mom and dad would have to sit and hold my hand for me to fall asleep at night because I would just sit there, spiraling on this crazy idea—maybe this is why I studied philosophy—that someday I would not exist, and that just freaked me out for decades.

That probably kicked off this introspective period of my life where I was very curious about philosophical traditions and religious traditions and metaphysics and all this kind of stuff because I wanted to know what the hell the point of all this was. What's the point? What's the meaning? What's the purpose? Otherwise, it's just terrifying, right? We're here for a blip and then gone.

Yeah.

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 where I wanted to understand myself and others, and so I was very introspective. Of course, that made me want to not live a dull life, and I was very scared of just living this train-track existence.

So it did help a lot. But interestingly, once I've clicked into, I think, understanding what I want to do, I don't think about it at all. Now I have very little introspection left in my life. I used to be so obsessed with all of these personality tests and what they mean, psychology, seeking, and 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.

Patrick O’Shaughnessy

You solved the problem that you were using it—

Yeah, maybe.

Patrick O’Shaughnessy

Introspection was the tool.

Yeah.

Patrick O’Shaughnessy

And then you don't need to use the tool once the job is done.

Yeah, maybe. Maybe that's right.

Patrick O’Shaughnessy

You mentioned earlier that we have different approaches, and then you wanted to talk about that. I'm always curious—again, some of this I should not say on a podcast—but I'm always curious about people who know me well: What is their interpretation of their view of me that's different from my own? What do you think my organizing principle is?

Your organizing principle.

Patrick O’Shaughnessy

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—

Just to clarify, it's not helping as many people as possible. It is trying to see enormous, not-yet-realized potential. My principle is that when I do, it is my obligation to tell people about it and to help foster it into existence. Maybe I invest, maybe I end up benefiting, but that's not the point.

4. Breaking The Family Pattern

Patrick O’Shaughnessy

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-you-do person that I know, in the sense that most people who have achieved a level of success in their field or job that you have begin to branch.

The world, when that happens, pulls you into this branching exercise, where you end up doing lots of different stuff. You end up monetizing in different ways or going into different lines of business, changing how you do things, expanding. The single-mindedness that you have is quite distinct from that of the people I know.

And why are you doing it? I mean, I think you've talked about this certainly in private with me, but also in public. We came from opposite circumstances. I was born on proverbial third base or sliding into home. I come from a history of extremely successful entrepreneurs. My great-grandfather had the best name ever: Ignatius Aloysius O'Shaughnessy.

Everyone called him IA. He was, I think, the 13th of 13 kids. He was one of the richest men in the United States. He was an oil wildcatter. The first oil well he ever drilled, I think, still pumps oil to this day in the Midwest.

He was a giant. His company was broken up in the antitrust action around Standard Oil. Our family takes great inspiration from him because he made this fortune, but 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 this story about being at his funeral when my dad was 11. All these people were there, and no one knew who they were. My dad would go up to one and say, “Who are you?” And they would say, “Well, Mr. IA, I cut his hair, and he put my kids through college and bought me a house,” or, “Mr. IA did this,” or, “Mr. IA did that.” We didn’t even know where it went.

I have benefited from this tremendous history of business success in and around my family forever, whereas you came from a very different set of circumstances. Our friend Sam has this idea that there are founders of businesses and founders of families, and I think of you as the founder of your family. 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 that the story of the father and the son are the same. It takes tremendous character, willpower, talent, and lots of other things to break from that family tradition and go in a new direction, which you’ve done. I just think that’s remarkable. I don’t know if that’s the underlying why—that you refused to let your family continue to go in the same direction it had gone up until you were born.

You went, as Sam would say, and as we’ve talked about, 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. It worked. It worked for you to change your life, and now we know, based on your work, that your work is changing other people’s lives in the same way that you changed your own first. But you were the first beneficiary of it.

So what is your principle or why? I don’t know. Maybe it’s that you don’t have to just keep going in the same direction that you were given. You can break off and found something new. I think that’s pretty amazing.

I really resonate with what you said when you found that book and thought, “This paragraph, this sentence just hits you with a hammer to the face.”

Patrick O’Shaughnessy

Mm-hmm.

5. Understanding People Deeply

I use podcasts for this. I read mainly. I think people are rushing through things too fast. 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.” I’m not speed-reading here.

I want understanding. I want understanding of how things actually are, not how humans say they are. Humans are constantly lying to themselves. If you’re lying to yourself, of course you’re lying to other people about why you’re doing what you’re doing, or what you’re doing, or what it is that you’re doing.

This is why I like autobiographies and biographies so much. In many cases, the person is long past dead, or they’re older and they’re just like, “I’m writing this book when I’m 80.” I have no incentive to lie. Here’s the stuff I went through: the trouble with being a dad, what kind of dad you are, trouble with women, trouble with business.

But you realize that there’s nothing you’re experiencing that somebody else hasn’t already experienced. So what I want is true understanding of humanity as it is, human nature as it is, and the world that we’re creating. Then I use their stories. It’s not really about them. It’s about you.

I don’t think this has anything to do with me. I think when you watch a great movie, hear a great story, or hear a great song, you’re not thinking, “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.” It’s a form of understanding: I’m in the middle of this right now.

We were just having lunch upstairs, and essentially I’m in the middle of trying to find the story that I want to tell with this book that grabbed hold of me for 6 months. I told you about this: it’s Bruce Springsteen’s autobiography. I’m not even—I don’t even listen to his music. I told you about this right when I read it. I was like, “There’s stuff in this book that this dude looks like he crawled inside of my mind.”

Especially in regard to how he views his work and the impact that it has, it’s like that is not a sentence, that is not a paragraph. That was made for me to read at this point.

Patrick O’Shaughnessy

Mm.

It’s insanely powerful, to the point where it’s like a drug. I told you right away—you need to give me credit. We’ll go back to this drug and understanding, because I think this is really important about people understanding why I want to talk to certain people and why I was adamant and pushing you on this.

We rescheduled a few times, and I wouldn’t be doing this if it wasn’t for you. Not only because of the platform that you gave Founders—the podcast—but also that crazy episode that we did together, which I think was lightning in a bottle.

Patrick O’Shaughnessy

It was, yeah.

It’s Invest Like the Best. The title is “Passion and Pain,” and people are always like, “Did you guys sketch this out?” I was like, “No, Patrick doesn’t sketch things out like that. We built a friendship. He wanted me on the show.” I don’t think you told me anything we were going to talk about.

I do remember you texting me a few hours before. We were supposed to do it at around 10:00 a.m., and you were like, “Hey, I got pushed back. Can we do 1:00 p.m.?” I’m like, “Oh, no, my brain only works in the morning.” So I took a quick power nap, and I’m in this booth.

We didn’t do video, but you can see me. I’m in this phone booth that I put in my house. I was the only person who had one. These phone booths are all in offices. They came and delivered it to my house, and I was like, “This isn’t a phone booth. This is a podcast studio. This makes perfect sense to me.”

Then we just had that conversation, and that was a huge inflection point. That weekend after that was one of the craziest weekends of my entire life.

But then you pushed me for years. You were like, “You should be recording conversations. You should be recording these conversations. What are you doing?” And I was like, “No, no, it’s a distraction. I don’t want to do it. I don’t want to do it.”

I’ve told this story a bunch, but I think it’s really important. I would not be doing what I’m doing right now, at this very moment, if we hadn’t had this dinner with Daniel Ek in New York. It lasted 4 hours. I know you don’t like when I tell you how long I talk to people.

Patrick O’Shaughnessy

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

Because I’m not interested in superficial at all.

Patrick O’Shaughnessy

I just had this 4-hour lunch with so-and-so.

Yeah, because I’m not interested in superficial. I met—I can’t tell you who it was—I just had dinner.

Patrick O’Shaughnessy

How long was it?

I’m going to tell you right now. It was an incredible dinner the first time we met, and it was unexpected, requested by them. Three hours into this, this person was like, “I have told you things no one else knows about me,” the very first time I met them.

I have no interest in the superficial, and I think you have to talk for a long time because it takes a little while to get warmed up and feel the person out.

Patrick O’Shaughnessy

Mm.

This is why what you said earlier is so important: fewer deep relationships. Think about the crazy conversation—which we’re not going to relive—but you and I just had an insane 2-and-a-half-hour conversation in Tel Aviv at around 2:00 in the morning.

Patrick O’Shaughnessy

Mm-hmm.

To have that level of honesty in conversation, you would have to have years of getting to know somebody. So I do think—

Patrick O’Shaughnessy

I also think you’re providing people with a sort of set of ingredients, maybe, through these episodes and conversations, but it’s important that people then go make their own recipe. You shouldn’t just want to live like person XYZ.

A lot of people you cover have the same pitfalls in their lives, and one might be tempted to think those pitfalls are inevitable byproducts of success. But I hate that kind of thinking. I think, screw base rates. I don’t care what the base rate is.

The most interesting stuff is outliers by definition. I don’t care what happened to everybody else. I don’t care if there are common pitfalls. I think it’s important that people take their own ingredients and make their own recipe from what you’ve offered them through all these amazing and interesting lives that you’ve studied. You’re just doing that for yourself.

That's been the search.

I think it is for myself. You are interested in other people, frankly, in a way that I am not. It's very real, and it happens every time we're together with other people. I'm like, “Oh, he actually wants to know,” whereas I am on this search of how the hell do I not have a terrible life?

Patrick O’Shaughnessy

Hmm.

This is why I think the skill set that gets you to where you are is where so many people plateau. I'm not interested in plateauing. I'm not interested in mailing it in. I'm interested in getting to the end of my life. I don't want to tap-dance on a giant reservoir of potential.

Patrick O’Shaughnessy

Hmm.

I want to figure out how to get the most out of my skill set and everything else. There's something you just said about a line in this Bruce Springsteen autobiography where he's like, “People don't come to concerts to learn. They come for you to remind them of stuff they already know is true.”

Patrick O’Shaughnessy

Hmm.

And I think you're going to learn. There are obviously creative ideas about how to build a company in a 400-page biography of somebody, but what you're going to realize is that there's a lot of stuff you already know is true.

Patrick O’Shaughnessy

Hmm.

Either you haven't applied it, you forgot it, or you did it for a little bit and need a reminder. This is why you and I always describe Founders like it's church. It's church for entrepreneurs.

Patrick O’Shaughnessy

In that church, I think the animating, interesting question is this: You read these stories, all of which come back to my idea of originality, hardship, and transformation—best story wins—and that originality is inspiring people to wonder, “What's my thing?” Everyone's got something, I guarantee it. It's my favorite thing to search for in conversation, especially if someone's not yet doing it, which is kind of the same search for unrealized potential or something.

Everyone has a thing, and searching for that thing—whatever the reasons, whether their life experiences, how they're wired, or their naturally endowed gifts—is really interesting and really hard. I think that's what Founders continues to do for me: show me examples of people who went to the trouble to find their thing and then, once they found it, fostered it for the rest of their lives.

Again, once you find your thing, the second thing is hardship. It's not supposed to be easy. Nothing meaningful is easy, and that's fine. Once you learn that, I think that's when it gets really fun. I always have this feeling that the second something feels easy and I'm going through the motions, I get really uncomfortable and want to try to push myself in some new way.

I think that's what Founders does so well. Back to the very beginning of our relationship, when I sent that tweet out and we talked to each other for an hour the first time we talked, it's because it was so unique, different, and inspiring. I think it's a powerful thing to do for people.

When I say, “What is my organizing principle?” it's like I want to understand things. Or, well, not things—I want to understand people. To understand people, you have to go deep: Where were you born? What was going on? What was this experience like? You have to spend a lot of time asking them questions and having these long, deep conversations. There's a handful of people I feel I truly know.

Patrick O’Shaughnessy

Hmm.

It takes a long time—at least 100 hours of conversation, on the low end.

Patrick O’Shaughnessy

You mentioned—you said organizing principle.

Yeah.

Patrick O’Shaughnessy

Just to push, because this is going to be something we talk about for the next couple of years—which is probably how long it'll take to articulate—that's different from, “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 correction is an act of service for other people, not for yourself. It's not about you. That's what makes the idea so powerful. I agree that that's your organizing principle. That's the thing behind why you're doing what you're doing.

It will be fun to try to pin down what the principle is for invention, because that's what you're doing. You're making new things, which is the most fun and rewarding experience of a lifetime. I remember the opening quote in this compilation of Joseph Campbell's life's writings, which 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.”

People who make the most interesting things make things that are a reflection of themselves. That's the most sustainable form of creation. If you can spill yourself onto the thing you're making, which benefits others—being of service to other people in some way—I think that's what we're all after.

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

6. Sustaining Success

One of the biggest things I want to avoid is finding the thing, doing the thing, being great at the thing, and then having something I do cause that to stop. I'm obsessed with sustained success. I don't want to have this huge spike. I don't want to flame out. I'd rather just do the slow build decade after decade, get better, and keep doing it.

This is why, essentially, I read fiction and biography. That's basically what I read. The biography part is just: Okay, what happens after they got what they wanted?

In the conversations I've been having—a lot of these have been on camera, but afterward, off camera, I'm always asking, because most of these people are older and more experienced, and obviously more successful, smarter, and everything else: “What do I have to worry about? What am I not seeing that could cause me to stop? I like what I'm doing. I love it. What am I doing that would cause me not to be able to do that?”

Patrick O’Shaughnessy

Hmm.

There are interesting human questions about this.

Patrick O’Shaughnessy

Well, the trap is that, before you do the work to figure out the thing that makes you feel alive, there's a great line in the Upanishads that's always referred to as “abiding joy”—joy that doesn't run out. You don't use it up like you use up so many resources. As you use it, you get more of it. That's abiding joy.

The target for most people becomes traditional money, power, and fame, because those are worldly proxies for success that we all recognize and that are, to some degree, true. It's hard to get a lot of those three things without being successful in some way. I think those things are huge traps because, once you start to get one, it's the thing you start chasing, and that's different from chasing the feeling of being alive—that abiding joy of feeling alive that we talked about earlier, which you'll never run out of.

That will always guide you well, always. Money, power, and fame will not. I think the answer to your question, or your worry, is just to make sure you're chasing the feeling of being alive and trust the intuition around that, and you'll be fine. It's when we get sucked in. I've, of course, like everybody else, been intoxicated by those three things at various points in my life, because they're intoxicating, and it feels really good the first time you have a lot of one of those things.

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

Patrick O’Shaughnessy

Yeah, I don't. I don't. I wish I could do what I do—and you know that thing in Men in Black where they flash you in the face? I wish that, at the end of each of my episodes, it would flash people in the face so they forgot who I was and didn't recognize me.

I've been thinking about this lately. You have limited time, and every day, where do I spend it?

Patrick O’Shaughnessy

Hmm.

It's three things: health, work, and relationships. I can't think of anything else I care deeply about. Health has to come first, because if we're sick or have no energy, we can't do anything else.

Other than that, if you look at how I spend my time, it's essentially that I'm creating work that I hope makes somebody else's life better, that I'm truly chasing that abiding joy, and then I'm deeply interested—in a shocking way—in having really strong relationships with other people. I wasn't like that 10 years ago.

Patrick O’Shaughnessy

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. When you're doing something you love and have great core relationships, all of a sudden, magically, your health gets way better. During that time when I had lots of health problems, I ate unbelievably well, I worked out every day, and I did everything you're supposed to do.

Yeah.

And then some. I was crazy about it. I kept daily logs of all this stuff. There was nothing I didn't try. There was no woo-woo thing that I didn't explore. I tried everything to solve some of these problems, and I couldn't solve them. At one point, I felt resigned to just, I guess, being one of those people who's going to be sick in life. That's just how it's going to be for me.

It cannot be a coincidence that when I finally started doing the thing that I think I was meant to do with my life, spent all my time with the people I cared about, and focused on those relationships, all of a sudden my health got better. So now, of course, I still invest a lot in my health. I'm not arguing with the 3 key things, but I found that an interesting experience in life. The body keeps the score.

The fame part is interesting because this is something that you uniquely understand and I can talk to you about. It's not to be known for the sake of being known. Those reality TV people—that's weird. I want my work to be so good that it can't help but become known, talked about, and spread because people find value in it.

This is just human nature. If you find value in a song, a movie, a book, a podcast, no one keeps that to themselves. A restaurant—we are compelled to tell other people about the things that we like. What I would say is that the reason I think I view it differently from you—and you can tell me if I'm wrong, or not even wrong—is that it's the relationships that you get to build as a result of being easy for other people to understand.

No one's going to stumble upon any of my work and be like, “What is this guy actually interested in?” It's quite clear.

Quite clear.

Yeah, it's quite clear, very obvious. My point is that I think this comes down to a principle: Why are all the people that I've studied, either had a conversation with, or read about, great at what they do? I do think it has to do with the most fundamentally important thing that you do in life: choose who's around you.

Of course.

Your friends, the people you work for—your company is the people that you're able to recruit and build. What I couldn't understand is that I was not interested at all in relationships with other people 10 years ago, somewhere around there, whereas now I invest a ton in that element. I think it's the part I'm most excited about and have been for quite a while.

I'm very excited about my work. That has never diminished, but I think relationships are the part I'm most excited about.

Well, because, of course, on your deathbed, that's what you're going to be thinking about, not your 5,000 podcasts.

But that's surprising to me, Patrick. This is why this freaking Bruce Springsteen book, Born to Run, is messing with me so much. I'm seeing this: He's 66 when he writes it—so 67, something like that. Now he's 76, and I just heard him in another interview talking about it. The first half of the book is about this guy who has one of the most insane work ethics that you've ever seen, channeled into one thing, and he has had no doubt since he was 15 that this is what he's going to do. He realizes that he does not have the skill set to handle all these things.

I'm just going to try to explain this. We just recorded a whole podcast about it, so maybe this will hopefully make sense. It was surprising to me that this man, who is psychopathically obsessed with professional achievement, fame, stardom, and all the things that he was very upfront about wanting from a young age, gets it—which I'll get to in a minute—and his final realization is that life is more important. Work is a part of life. It is not my full life. Life is life. It is important.

His biggest struggle was that he became famous. Jimmy Iovine told me this because I got to meet him, and right when I was leaving his house, he said, “You need to go watch the new Bruce Springsteen movie,” and it's called Deliver Me from Nowhere. I thought it was going to be a biography of his life. That's not what it's about at all. It is a dark movie. I was shocked.

This is the key to understanding: an unbelievable, terrible environment that he was born into. You're going to have 2 reactions there. You're just like, “This is what life is. I'm going to accept it,” or you're going to have this maniacal will to change things.

Mm.

He has that maniacal will, and he's like, “I don't want to live like that.” His dad was one of the worst human beings to him. He takes all that pain and channels it into a work ethic that gets him exactly what he wanted. He gets what he wants: Now everybody knows who he is. He's worldwide famous, he's rich, everything, and then he immediately drops, in his mid-30s, into the deepest depression of his life.

Mm-hmm.

What he realizes is, “That's not what I actually wanted.” This is what it comes down to. I think I told you this upstairs, or maybe I even mentioned this. I had a very interesting conversation at dinner last night, and it started with, “What is the lie that you're telling yourself?” Another person and I went around that for quite a while.

Mm.

It was very fascinating. The lie Bruce was telling himself was that work was the most important thing, that becoming a rock star was the most important thing, and that fame was the most important thing. What he realizes is that his parents had so messed up his emotional well-being that he was incapable of doing the thing that he wanted. In his case, he desperately wanted to have kids, to be married, to break the chain, as we mentioned earlier, so that his kids would not experience what he experienced.

Mm-hmm.

He even wrote a whole album fantasizing about this before he was able to do it. He would run into the same thing: He'd be onstage in front of 40,000 people. They all love him, and yet, in his case, he talks a lot about women in the book. He would get close to a woman, have some kind of feelings for her, and she'd have feelings for him back. Then he would immediately go, “Why do you love me? 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.”

Mm.

Patrick O’Shaughnessy

Then he'd run away, and then he'd get into another relationship, and he'd go over and over and over again. He didn't realize the source of his depression was that he didn't know what he actually wanted.

Mm.

Then he winds up meeting another woman who's in his band—he's married, by the way—and getting divorced because he realizes, “This is the person I'm willing to do the work necessary to fix things for.” Then he goes through 25 years of therapy, and in some cases he has to get on antidepressants. He's unbelievably honest about what took place from 35 until 67, when he's writing his book.

I think there are all kinds of lessons in there, from the personal question of what you actually want in your personal life to the kind of relationships you want with friends, romantic partners, whatever the case is. But this is what I meant about wanting 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.” We have a million conversations. You're just like, “Why don't you have a team? Why don't you do all this?” It makes sense why I don't have a team, because I don't fucking trust anybody.

Mm.

Patrick O’Shaughnessy

It's obvious why that is. I do think I'm getting better and better and better, even with the stuff you and I talk about. 10 years ago, there's zero chance I would have let that come out of my mouth.

Right.

Zero.

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

I know.

And maybe my arrival at the aspiration—I’m by no means perfect—is to be more service-oriented. My grandmother, who just passed away, was 99. She banged on me. Every time she'd see me, this would be the topic of conversation. She's like, “Yeah, yeah, yeah, congratulations on all the success. Who gives a shit? What are you doing for other people? That's what I want to know.”

I'm convinced that's the way out. I think, like you and so many people listening, I have a set of demons that I'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 need to read the book, obviously, but that seems like a tale as old as time.

But this is something I learned from you: this idea of making sure that your source of fuel and energy and ambition is generative—

Yeah.

Patrick O’Shaughnessy

—and not negative.

Yeah.

And I do think the conversation I've had with you and with Sam Hinkie is really important. I'm getting to the point where I push myself because I love it. I'm way nicer to myself than I have ever been because I'm like, “Oh, this doesn't serve me anymore.” I 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. If I get really good at it, money will come as a result because it's an act of service.

Patrick O’Shaughnessy

The clean fuel, dirty fuel debate is really interesting. And look, many—most, nearly all—of the books that you've read were about people who were fueled by dirty fuel. Dirty fuel works really well, but it consumes the person in a way that I would far rather die with nobody knowing who I am and with no worldly success, but having people who could count on me, whom I was faithful to and loyal to. That's what I want at the end.

So if you can work backwards from that, that's another cool way to think about it. Working backwards from what you hope is true is a simple heuristic for finding what to do well, and I think—yeah, I think I can't wait to read the book.

This is why I think reading a bunch at the same time—or not the same time, but having a lot to pull from—is valuable. I'm reading the Bruce Springsteen book, but then you realize another person with a superhero work ethic, drive, and ambition was LBJ, which Robert Caro brilliantly writes about, and you realize Bruce is generative. It took him a while to figure it out, but he got out on the other side of that, whereas LBJ never did.

Mm.

Patrick O’Shaughnessy

And even though their sources are very similar, there's a great story that Robert Caro tells in one of his books where LBJ finally gets to Washington. I think he's an intern—I don't even remember what job he has. He has no money; it's cold. The sun would be coming up at around 5:30, and this woman who worked with him would always see him running everywhere.

Mm-hmm.

Patrick O’Shaughnessy

And they just assumed, “Oh, he's got no coat, he's got no money; he's running to warm himself up.” Then summer comes and he's still running. Obviously, Robert Caro is a master with words and storytelling, and his whole point is, of course he was running. He finally made it to the spot because he was talking about how he wanted to be president since third grade or something. He finally made it to the city, to the place where all his dreams were, and 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 becomes the president of the United States, and it's the same thing. One is generative; one is unbelievably manipulative and probably not a guy that you'd want in your life, to be around. And so I think there's also value in learning from great examples, but almost seeing, “Oh, I don't want to be that way.”

Right.

Patrick O’Shaughnessy

This is something—one of the best things about our friendship is that I actually want to let people in. I want to have friends and deep friendships, and in the past that wasn't an important thing to me.

Of course.

Patrick O’Shaughnessy

This conversation is now therapy for David. But this is my point: when I wanted to sit down with you, there are a bunch of things I want to talk about, but I also want to talk about the stuff that we normally talk about. The reason I think it's important for me and you, too, is how much of our ideas actually came from the creation of the podcast. Think about all the different ideas and topics and things that you've learned as a byproduct of just making this thing.

Mm-hmm.

Patrick O’Shaughnessy

And then the unfair advantage that we have is essentially being professional learners.

Yeah.

Patrick O’Shaughnessy

You get to study somebody, you get to have a multihour conversation with them, and say, “Oh, wait, he said that,” or, “She said this.” I'm going to take that idea. Who have you grabbed ideas from, and who do you let influence the way you think?

How long have you got? I could easily rattle off 50 people.

Patrick O’Shaughnessy

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

To take the simplest example possible, in the early days of the show, this is a very practical, real-world example: I took the ideas that I got from Daniel Ek, whom you mentioned before at Spotify, about how to build software; from Brett Victor, whom I mentioned before, about this principle for great software and what it looks like; and from a guy named Chathan Pudigunta at Benchmark, one of the partners at a very storied investing firm called Benchmark, who taught me how to sell software—just those 3 guys.

I basically just stole their ideas and applied them 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 was able to pull it off, but the direction of the resources and what to do strategically just came from asking 3 of the greatest in the world at what they do, “How do I do this?”—and then not thinking too hard about what they told me, just doing it, and having it work.

And so there's a tiny example: 3 people.

Did you have all 3 on your podcast? You had 2 out of 3.

Patrick O’Shaughnessy

I've never met Brett.

Okay, so you have 2 out of 3.

Patrick O’Shaughnessy

I've never met Brett. Yeah.

These ideas came from conversations that you had on the podcast?

No, I didn't ask them this stuff on the podcast, but in time spent just offline with them. I'll never forget: I was in Benchmark's office in San Francisco showing Chetan the demo. I'd show him the demos, and it was amazing. He'd give me feedback. They weren't investors in my business or anything. He was just doing it out of the goodness of his heart, I guess, and the same thing with the others.

There were many more than 3 people who contributed to that project, who influenced me and taught me things. But mostly just offline, asking questions. I did interview Chetan several times, and Daniel sometimes.

Patrick O’Shaughnessy

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

Yeah.

Patrick O’Shaughnessy

You try to email the Aman in New York and ask them if they'd let you 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 would say relationships run the world, and our jobs are essentially learning and then taking what we learned and packaging it for somebody else to easily consume and benefit from that learning—

Mm-hmm.

Patrick O’Shaughnessy

—whether it's a conversation, a book review, or whatever the case is.

Mm-hmm.

Patrick O’Shaughnessy

So that's very practical. That was in the early days when you were doing Canvas, right?

Yeah.

Patrick O’Shaughnessy

What about larger things in your life? Who do you think had an impact—my life would not be the same if not for that one conversation or that one idea with that person?

Two people came to mind right away.

Patrick O’Shaughnessy

The first is Herb Allen from Allen & Company, whom I don’t know well. These lessons came from one incredibly interesting conversation. My sense of him, again, not knowing him well, is that he is uncompromising in his values. He’s maybe the apex predator of the thing I want to do, which is picking and supporting people.

Mm-hmm.

Patrick O’Shaughnessy

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. I think he’s famously willing to throw away huge commercial opportunities just because the person wasn’t who he wanted to support. Sometimes it’s literally a conversation with a person that smacks you in the face and makes you feel validated, maybe, for what you’re trying to do.

There’s a gentleman named Reese Duca who’s been very, very private, and there’s no content about him or interviews with him. I wish to God he would let me interview him. I know he never will. He has been incredibly impactful on me at a philosophical level. He has all these amazing little phrases.

But his life kind of boils down to simplicity—the beauty of simplicity. He gave me this line one time: “Simplify your life with rhythm and harmony.” And that line is what you’re talking about: fewer, deeper relationships; fewer things, better; everything aligned with what gives you energy; listening to your own feeling of aliveness. He lived that to a degree that’s rare, that I’ve never seen.

A gentleman I spend a ton of time with now, named Jesse Beyrouthy, who I am with basically every day, also, I think, has no interest in fame or accolades or recognition. But I think he will go down—I would predict—as one of the great investors ever. He’s like Reese. He’s completely uncompromising in the most principled way of living I’ve ever seen. He just refuses to get sucked into the game.

God, man, I could rattle off names for hours and hours. There are so many people that have influenced me, and that’s what makes this all fun. That’s what makes what you and I do so fun: I’m inspired constantly, and you’re doing this new show. I interview people once a week, but really I interview 10 people a day. That’s what I do.

I just happen to have mics there one of the times. If I’m doing it 40 or 50 times a week, which is not an exaggeration, it really is that many people every week, just asking, “Who are you? What’s your deal?” I love doing that. So there are just too many to name, but those are a couple that came to mind.

Munger said—I’m paraphrasing—but he’s like, “You know, one of the best ways to learn is you find somebody who’s kind of an outlier, and you just ask, ‘What the hell is going on with this person?’”

And you just keep asking that question to try to get deeper and deeper and deeper, reverse-engineering what they’re doing and why they’re really successful. There’s another fascinating thing where everybody has a podcast now. Everybody starts podcasts. And as soon as that takes hold, you’ve been doing podcasting for 10 years, and you decide, “No, I’m going to go in a different direction.”

A 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 use them as source material for our Founders episode. I think we should do more of those collaborations, because they were really well written, kind of doing my job for me.

Patrick O’Shaughnessy

Yeah.

Why did you decide to do that?

7. Building A Media Flywheel

Patrick O’Shaughnessy

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

At a very high level, the reason we now have a magazine—which, on its face, I think everyone would have agreed was a stupid idea, or told me was a stupid idea when we started it—is this: 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 a beautiful way to shine the light beyond podcasting on people that we admire, and to teach the world about a compelling founder or a compelling investor or artist or whatever.

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. When we started doing this, I went and read David Remnick, the longtime editor of The New Yorker, and New Yorker profiles were always my favorite growing up: these incredibly detailed, amazing, well-written profiles. In the introduction to his compilation of his favorite New Yorker profiles, he wrote, “The best profiles over the last 100 years are defined by somebody doing a thing they’re obsessed with and a writer that is as obsessed with the person as the person is with the thing.” I remember reading that paragraph and thinking, “Wow, that’s what I want to read.”

So I went and read a million profiles, and the very best one I read was in a publication called Tablet, on Palmer Luckey from Anduril. I reached out to the author; his name is Jeremy Stern, who’s now the editor-in-chief at Colossus. The rest of that story is history. He joined.

We’ve got other people that have joined or are joining to write these profiles, and it just felt like, wow, this is another way to do the thing we love to do: 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.

The one that we wrote about Josh Kushner at Thrive Capital was one of these bizarre break-the-internet moments when it completely took over the internet for a while. I remember reading it the first time, and I was 45 minutes into reading it, and I was still reading about the Holocaust. 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.

Jeremy, 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. I thought that was the coolest, most beautiful thing.

This project has become an excuse to, first of all, find more talented people—the writers—that we can support, which is great. See the potential, you know? It’s the same thing we’ve been talking about over and over again. So now team members become more people that we can do the supporting thing with, and for them to write things they’re obsessed with and passionate about, and then for the rest of the world to benefit, for the people being profiled, hopefully to benefit.

If we tell the honest stories—and we want to tell the hard parts and the interesting parts—it’s been successful beyond what I ever could have imagined. And I think it’s important to note: when I started with the first idea, everyone said it was a stupid idea. I mean, literally everybody said it was a stupid idea. When I started the podcast, everyone said it was a stupid idea. When we started Canvas, everyone said it was a stupid idea.

I think if people say something’s a good idea, I always get a little nervous, because if it sounds like a good idea, it just feels like 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. Starting a magazine in 2025, I think, falls in that category of sounding 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 very, very big.

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

Patrick O’Shaughnessy

What specifically?

Colossus being bigger than the podcast.

Patrick O’Shaughnessy

Of course.

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

Patrick O’Shaughnessy

I’m not saying I want to stop doing that.

I know you. I know that.

Patrick O’Shaughnessy

For sure. I love it.

But I think in your heart, if you had to choose, you’d be like, “No, I’d rather have the profiles be bigger.” Again, this goes back to how I think we started the conversation.

Patrick O’Shaughnessy

Yeah.

I really do believe you’d like to be the guy behind the guy.

Patrick O’Shaughnessy

That’s true, but the reason for me is almost so obvious that it’s uninteresting, which is, well, if a bunch of other talented people are doing this and then creating these things...

First of all, I’ll have more of them.

Mm-hmm.

Patrick O’Shaughnessy

I’ll get to enjoy them just like everybody else. I can’t tell you how fun it is to get the first draft of one of these things in Slack. The things that make me the most giddy in my work are some new draft that they’ve created for Colossus and some new research report on an investment created by my incredible team on that side, who in many ways are just doing... It’s turtles all the way down.

Yeah.

Patrick O’Shaughnessy

It’s the same deep investigation, publishing, writing, and clear thinking. When I get one of those two things in the morning—sometimes there are days where I have several of them—those are the best days. 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 it gets bigger and bigger, and I don’t want to fade into the sunset, but I hope this is much bigger because that means I get to hire more incredible, talented people and hopefully put them on a career trajectory that’s the best it could possibly be, and that’s incredibly gratifying. I get to read more of these things. I get to do this thing that we love to do for more people and point the light that we’re trying to cultivate on more and more talented people. That’s unbelievably exciting.

I hope it’s not just writing. I hope it’s documentary. Who knows where it goes? I hope we start convening people in small situations where it’s, “Meet this person, meet this person...” That, to me, is the most fun thing in the world. 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. So, yes, I would vastly prefer that all the rest dwarf whatever I do, even though I hope what I do lasts forever and is big itself.

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

Patrick O’Shaughnessy

Yeah, now everyone’s launching a magazine, and it’s just going to be like podcasts.

But not even that—specifically profiles, where people have been reading. You just mentioned it. I bought that book too that you told me about, The New Yorker Book of Profiles.

Patrick O’Shaughnessy

Yeah, yeah.

People have always been interested in people. I remember reading about Larry Ellison, who loves to pick fights, and he thought it was really good. He didn’t like the fact that Oracle had no media strategy. He was like, “Oracle is just compared to other database companies, and I don’t like that. I want to be compared to the best companies in the world.”

Patrick O’Shaughnessy

Yeah.

It’s almost like this idea that you and I 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 Sybase or any of the...”

Patrick O’Shaughnessy

Yes.

“Sea Bass.”

Patrick O’Shaughnessy

What is it?

That’s from Dumb and Dumber.

Patrick O’Shaughnessy

But I don’t know.

Siebel.

Patrick O’Shaughnessy

I don’t know what it’s called. All my vocabulary comes from the written word.

David, not an investor. Podcaster.

Way to go. Forever. All my vocabulary comes from the written word. Everybody makes fun of me because all my DMs are like, “You mispronounced this word. It’s very obvious, buddy.”

Patrick O’Shaughnessy

Yeah.

But his whole point is, “I don’t want to be associated with these people. I want Oracle to be in the same vein as IBM or Microsoft.”

Patrick O’Shaughnessy

Yeah.

So he’s like, “The way I’m going to do that is I’m going to pick a fight with Bill Gates and Microsoft.” He does this huge fight, and originally he thought it was going to be Microsoft versus Oracle. Then he’s like, “But people are interested in personalities more than they’re interested in companies or technologies.”

Patrick O’Shaughnessy

Of course.

So it became billionaire A versus billionaire B—

Patrick O’Shaughnessy

Hmm.

—and it greatly elevated his profile. Then he said that Oracle and Oracle’s products rose along with the increase.

Patrick O’Shaughnessy

Right.

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

8. Great Work Takes Time

Patrick O’Shaughnessy

That’s the other part that’s exciting, because I like things that are really hard. 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 to that, which I think is interesting and correct: it should be different and really hard, really hard to do.

If 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 have to go into them and the talent as a writer that has to go into them, but sometimes they’re sensitive parts of the person’s life that have never been written about and they’ve never talked about. Maybe they don’t want to talk about it, or they don’t want you to talk about it. It’s coaxing it out of them, and that takes time and trust.

The thing I can’t wait for is the profile that we write 10 years from now that we start working on today. We have this idea, which we’ve started to do, where we just ask people, “Can I just have lunch with you once a year? I’m not going to do anything with it. I just want to start collecting the line.” Maybe we’ll write something in 10 years.

Things that are really hard to make are really interesting to me, and I think people stopped doing profiles because they’re really hard to make. They take time. The business model kind of sucks. The pay is terrible. 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.

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 all day, every day. It’s just crap. Everyone makes the junk-food comparison because it’s a perfect comparison. 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 with most content, and everyone knows this in their gut. We all want something more carefully created.

I think a profile might be perhaps the ultimate expression of that. If a documentary is the ultimate profile, maybe that’s even harder than writing a profile. I’m interested in stuff that’s very hard to make and that’s singular, that can’t be easily copied.

The literal answer to your question is kind of funny. Somebody—I’m actually seeing him Monday—gave me the idea to potentially buy this existing magazine. 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 people on the cover. I’d never heard of the magazine, and I thought, “This is strange. Why are these people doing this magazine that no one’s ever heard of?” They were big names.

It dawned on me: it was the cover. People can’t say no to a cover. I tested that theory out, and it was true. I think what that means is that it’s the ultimate form of spotlight and attention that you can give to somebody. That’s what got me literally spinning: 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 Luckey?

Patrick O’Shaughnessy

Before. I was then on the hunt, and this is another idea that you and I talk about often: if you want to hire someone for a thing, just go consume as much of the thing made by a million people as possible. Whoever made the best one, go for them.

There was this funny conversation during COVID. An investor friend of mine, one of the great investors ever, who’s now retired, was part of a Zoom conversation. The topic of the conversation was the attributes of great founders. At some point someone goes, “Well, maybe it would be easier to think about them not as founders, but as inventors.” Everyone thought, “Oh, it’s a cool idea. Okay, let’s talk about them as inventors, not as founders.”

Then someone said, “What are the attributes of a great inventor?” People started saying, “They’re this, they’re this, they’re this.” This one investor’s face started contorting, and you could just see that he was frustrated by all these answers. 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.

Yeah.

Patrick O’Shaughnessy

And so I think you and I have taken that approach to finding people. Just look at what they did. Jeremy wrote the best profile that I read. It turns out he’s a great profile writer. He’s written 10 more and will write 100 more.

I was then on the hunt, after we had this idea, to go find the best people to do this thing.

People vastly underestimate the importance of volume. Whatever you’re into, just be into it more than anybody else, and you’ll be able to tell what is a good idea and what is a bad idea. It’s this constant refinement of taste.

In fact, I was shocked at the way your profile about Josh Kushner started.

Patrick O’Shaughnessy

Mm.

It was this visit to Rick Rubin’s house, and I’m a huge Rick Rubin fan. I did a biography on him. I think it’s Episode 245 of Founders.

In some of his interviews and stuff, he says that it can be a 3-hour conversation, and you just hear a 45-second clip that makes everything—it just makes perfect sense. I needed to hear that whole 3-hour conversation just to get that 45-second clip and that idea in my head.

But think of the guy who started his record company in 1984 in his dorm room.

Patrick O’Shaughnessy

Mm-hmm.

He’s been in the same business and has worked with all these different musicians. In fact, he said something that was interesting to me, and I actually screenshotted it, saved it, and reread it on my phone. He talked about how the most obsessive artist he ever worked with was Eminem.

It’s like, wait a minute, you worked with everybody. You’ve had a 4-decade-long career. Why is that the case? That makes me want to know more about that.

Our mutual friend Brent Beshore told me this hilarious story one time. Brent owns a bunch of different companies, and sometimes those companies need a CEO. He found himself, I think, at a lunch or dinner with Charlie Munger, so he said, “You know, I’m this young guy”—I think he was probably 35 at the time—“I own these 12 companies. How do you and Warren find great CEOs?”

Charlie just said, “We just find somebody that is a great CEO and say, ‘Come do that for us.’”

Patrick O’Shaughnessy

Yeah.

Brent’s follow-up was, “Yeah, but what about hiring for potential?” And Charlie said, “We don’t do that.”

It’s just a beautifully simple idea: He’s really good. Can you come do this over here?

Patrick O’Shaughnessy

Yeah. People show you. I think that, if you invert that, to use another Mungerism, it serves as great advice, too. 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 breadcrumbs out into the world so that people see it and are amazed by it. If you create a single thing—you don’t have to do 10 things, just 1 thing—that people are amazed by, pour a year of your life into making 1 amazing thing that people are amazed by, and amazing things will happen. I promise you.

The internet is amazing at sharing something that is great. You say there’s always room for great.

Yeah.

Patrick O’Shaughnessy

That’s true. Great takes time. Great’s hard.

You just proved this. The idea that there’s always room for great came because so many people were like, “We don’t need another podcast.” And I was like, “Okay, so we don’t need any more music? We’re going to stop making music? We’re going to stop making movies?”

No. We need less bad shit, but that’s always going to happen. There’s always room for great. You just proved this with the profiles.

Patrick O’Shaughnessy

Yeah.

That idea was just hiding in plain sight. It was just not being done well. What if I just take this idea and not make it shitty?

Well, Walt Disney, toward the end of his life, was asked what he was most proud of. Everybody associates him with animation and Mickey Mouse and everything else, and yet when he was toward the end of his life, he named 2 things. He said, “Keeping control of my company,” because he lost control of his first company and the first characters he made, and Disneyland.

Disneyland was his obsession. In fact, I read this book called Disney’s Land by Richard Snow. 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.

At the time, amusement parks were thought of as low quality.

Patrick O’Shaughnessy

Yeah, sure.

They were kind of scammy.

Patrick O’Shaughnessy

Traveling carnies.

Yeah, exactly. You would come in there, and there would be games to play, and you’d get ripped off because the games were set up that way and everything else.

He was going around trying to raise money for this, very unsuccessfully, and people were like, “Yeah, but amusement parks are kind of trashy.”

He was like, “That’s the point. Mine won’t be.”

Patrick O’Shaughnessy

Yeah.

Mediocrity is always invisible until passion shows up and exposes it. He was just like, “I’m going to take every single part of this and make it better, and then remove the parts that don’t make any sense.”

Patrick O’Shaughnessy

Mm.

That’s a great filter for finding new things to create in the world.

Patrick O’Shaughnessy

By the way, I spent my 20s basically just reading, and I read more than you can imagine. You’re probably the one person who can imagine it because you did something similar, but I was reading literally everything I could get my hands on—thousands of books and profiles and everything.

I started the podcast in part because I started to feel this awful feeling of, “This is happening in this weird, isolated way.” It was just me and my notes. I wasn’t talking to anyone about these books, so I wanted to start sharing. That’s where that book email came from, which is where the audience came from.

I used to have this saying: “Learn, build, share, repeat.” Just do that until I die.

That’s right.

Patrick O’Shaughnessy

I believe in that.

It’s still—wait. “Learn, build, share, repeat.”

Patrick O’Shaughnessy

Yeah.

Still really good.

Patrick O’Shaughnessy

Still works.

Yeah.

Patrick O’Shaughnessy

Maybe that’s my governing principle, probably, like you said before. It’s an incredibly powerful loop to go on.

The 10 years of reading prepared me to be a good producer of profiles because I’ve seen great, I’ve seen good, I’ve seen average, and I’ve seen bad. My reps are very, very, very high.

That’s another thing I always tell people, especially young people: What is the thing where you naturally have a lot of reps because you just like it? Find some way to build off that, because there’s this learning-by-doing concept. You get better at something just through being prolific in the thing, and most people have a thing for which they are naturally prolific.

Even if that’s following your sports team or whatever it might be, what’s the thing you just can’t help but do a crazy-high rep count of? Probably that’s a good clue to where you could go build one of these compounding curves for yourself.

For me, it was reading. My first love was reading. That love of reading became the email list: “Here are my 4 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, and on and on and on. That led back to the profiles.

Led back to the profiles.

Patrick O’Shaughnessy

That led to Positive Sum, and me building my business successfully in software got me to all of these people building early-stage companies and 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 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 20s, and I did something about it. I started telling other people which ones I liked. That’s how it started. That’s it.

All of that was unpredictable. Back to why I don’t like goals: If you had told me, when I sent that first email, to list my goals, none of those things that I just listed would 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. I wanted to grow. I love the idea in weightlifting—Jeremy Giffon and I talk about it all the time—of progressive overload: always a little bit harder, a little bit more. Go to failure, go to failure, go to failure.

But you don’t know where that’s going to take you. The beautiful thing about life is that you don’t know where that’s going to take you.

God, I never in a million years could have predicted any of this crap. What’s even more exciting is that it doesn’t stop. Some set of stuff is gonna happen over the next 10 years that, if I tried to make a goal list today, I would be unable to predict. It’s gonna be so much fun.

But it all started with a thing I loved naturally: I just like to read books, and I think that’s profoundly cool. Now, obligatory disclaimer: I had the privilege to sit and read a gazillion books and not spend all of that time just getting ahead, like you had to, because, again, I was very lucky. The situation I was born into in life, with the parents I had and the things that were easy for me—I didn’t have to pay for college—all this stuff made it possible for me to do these things, and I think that’s important to acknowledge.

Nonetheless, you found your way there. You found the passion. You found the high-rep passion, and now look. That’s my constant urging to people: it’s there, I promise. There’s something. Just go find it.

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

Yeah.

I want to talk about: is it code red? Seeing red? What is it? There’s this fantastic story we’ve talked about before, where you were going to make an investment in somebody’s fund.

Hmm.

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

He said I was red on the color wheel.

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

9. The Eye Of Sauron

Sure. So you, me, and Sam Hinkie were walking, and I think you asked Sam what my biggest weakness was or something.

No, you were interviewing—

Oh, I was doing the interview.

When you just said, “This all started from—I love to read,” and then that started this whole chain of events, you now have this other parallel thing that you do compulsively, that you can’t help.

Mm-hmm.

Which is 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.” If we’re in a group, I know what’s gonna happen. You’re just gonna start lighting people up with questions.

Yeah.

So we go on this 5-hour walk, which Sam did not like, by the way. People don’t know that you’re a goddamn billy goat. 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. If you’re out in nature and there’s a mountain, people usually say, “I’ll follow the trail around it.” No, billy goats just go straight over and up. That’s what it’s like walking around with you.

Yeah.

And so we’re in Columbia, Missouri, of all places. We go on this 5-hour walk, and essentially it’s a 5-hour private Invest Like the Best episode, except you’re interviewing both of us.

Yeah, yeah.

And you would ask the other person questions about the other person, which was really impactful and important for me to understand myself. Again, somebody you trust and know has your best interest at heart and is not trying to criticize you just to criticize you.

Mm-hmm.

I think a lot of people are hypersensitive to criticism, and if it’s 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 you this about yourself. You should—even if you don’t agree—think about it for a little bit.

Mm.

I’ve thought a lot about what he said over the years, and I definitely agree. He was right. I don’t know how this got turned on you, but that’s when he said—

Mm.

—you’re code red. No.

Red on the color wheel.

There you go.

Yeah.

What does that mean?

First, just a thought on Sam: it’s hard to imagine a higher compliment I could pay someone than the role that Sam plays in my life. The way I would phrase it, maybe, is I have more conversations with Sam when he’s not there than when he is.

What I mean by that is I’m often finding myself wondering, in a situation, “What would Sam think about what I’m going to do here?” I so value his character and judgment and fidelity, and just so many things about him. What a role to play in somebody’s life. He’s the one I invoke in my head—one of 3 or 4 people that I invoke in my head—with, “What would this person think about this thing I’m about to decide on?”

But back to the story. He said, yeah, it was something like, “What’s my biggest weakness?” He described me as being red on the color wheel, which he explained meant that, when I’m interested in something, I’m intense. I’ve always been this way. I am voracious and intense and aggressive, and I would say I have a skill at making things happen when I’m interested in them happening. Maybe that’s one side of the sword.

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

Yeah.

If Patrick is focused on you, he will make shit happen. But if it’s focused elsewhere, you’re not going to get that attention. I’ve had to fly literally to Greenwich. “Dude, get back. We need to focus on this.” In some cases, it’s a physical-presence thing. It’s not just that I can get you on the phone; I was like, “No, this is not good enough.” So that’s the strength. Your strength can be your weakness.

You know, it’s interesting. I learned something about myself recently, which I was terrified about at first, and now I’ve come to view as everything being double-edged. If you close your eyes and try to visualize something—a red cardinal or something—there’s a degree to how visually sharp that thing looks in your mind’s eye when you close your eyes. For me, it’s just black. I can’t visualize anything. I can’t see anything. I’m like, “Wait.” I discovered this about a year ago. I’m like, “Wait a minute. You can see things with your eyes closed? What are you talking about?”

Do you remember? We were at Brad Jacobs’s house having breakfast or something.

Yeah, yeah, yeah.

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

Yeah, I know. He tried to put me through a guided exercise. He tried to hypnotize me into visualizing something. 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 that, when I’m focused on something, like here right now, I am not thinking about other stuff. It’s just all of this. I wish it wasn’t the Eye of Sauron. That sounds so bad. But I understand.

It’s said in a loving way.

So Sam’s point was, you’re red on the color wheel, and when your attention shifts, it can be whiplashy for those around you.

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. He called me and said, “I’m putting this fund together. It’s a small, limited group of people. I’d love to have you if you want to do it.” I was like, “Hell yeah, I want to do it. Of course.” I told him the amount or whatever.

Then he called me back a month later and was like, “Okay, I have the docs all ready, and we’re ready to go. Are you still in for this much?” I said something like, “Yes, I’m still in, but I can’t do that much because, actually, I’ve also launched a fund.” I said, “I need to make a GP commitment to my own fund, and this is before I sold my business, so it’s a little bit tighter situation. I have to reduce the amount.”

He started to tease me because he was like, “Wait, so when I first called you a month ago, you had never even thought about having a fund? I’ve never heard you talk about that. I don’t think you’d ever thought about it. And now, a month later, you already have a fund? A month later, it’s raised and done?”

I think that’s a good example of, 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. I don't think this is a good thing, by the way. I don't want to whiplash people, and I realized, thanks to Sam, that I was whiplashing people. I would be so excited and willing and able to galvanize people around an idea, and then I would change my mind and completely forget about the idea.

Yeah.

Patrick O’Shaughnessy

Back to people that have this lack of visualization thing: they also have quite bad event memory. I don't ever think about stuff in the past—ever. So I not only can change my idea, but I literally never think about that thing again that I was so passionate about in the moment, for a short period of time. That is jarring for people that are 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.”

I've worked pretty hard to simplify my life with rhythm and harmony, focus on fewer things, and get less distracted by what I would call the “flavor of the month club,” which is something that can definitely snare me, for sure.

Now that you say that, I haven't had any Eye of Sauron moments with you in quite a while. You've kind of fixed that. I heard Ari Emanuel on your podcast say something that I thought was actually pretty smart: especially when he's trying to do a deal, he overcommunicates.

Patrick O’Shaughnessy

Mm.

I think a lot of the problem was that 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. What's going on here?” And then other people that knew you explained that, and then I'm like, “Oh, I'm having an issue.” We've never even had an argument or a fight.

One thing that I love about it is that we worked together for years, and we never had to put anything on paper. We never had a contract. We just said, “Hey, this is what the agreement is.” We shook hands, and we did what we were supposed to do up until the very end.

Patrick O’Shaughnessy

Yeah.

I don't want to have to deal with people where there's a bunch of contracts. I want to know that you gave me your word, I gave you mine, and then this is what we're going to do, and we'll figure it out.

But I think what was happening there was that there was all this unsaid stuff that you thought we were looking at in the same way. Yet if we just said, “Oh, wait, this is how I'm thinking about this thing, and this is how I'm thinking about that thing,” and just essentially overcommunicated as much as possible—

Patrick O’Shaughnessy

Mm-hmm.

—with the people that are important to you, then you're not going to have an unspoken assumption. If you let it sit there too long, then you have another unspoken assumption on top of that one. Then things can get really, really weird.

10. Leaders Teach By Repeating

Patrick O’Shaughnessy

I think a lot about leadership because, ultimately, my main job is to back people with LP dollars—lots of them—that have been entrusted to me as a fiduciary, into companies led by these people we're backing that are usually pretty early in their company-building journey. So you're largely backing the person and the team versus the mature business story. It's pretty important that that person be a good leader.

I think one of the things I underestimated about great leaders—Ravi Gupta is another person that I would list among the people who have really impacted me—is how to define a good leader. At one point, I called everyone I knew. I was like, “Well, define a good leader. I'm going to do a survey.”

Mm-hmm.

Patrick O’Shaughnessy

Ravi gave my favorite answer. He was like, “It's not hard. A great leader is someone that other people want to follow.” That's it. Everyone else had given much more ornate definitions, and Ravi's was my favorite.

What I've learned about what is shared in common among people that others want to follow—one of the big ones is that they are hypercommunicative with those people, they're consistent, and they lead from the front. They take risks. They take arrows for the team. They communicate like crazy with the team. If something's changing, they overcommunicate it. They're honest. All these things add up to someone that people want to follow.

I think I was quite bad on that dimension for a long time, not because I was trying to be bad, just because I was so excitable. I am so excitable. When I find something new and interesting, I just cannot get enough. But very often that means I'm billy-goating up ahead of the pack and forgetting, “Oh, wait, there are all these people that I want to do this with. I don't want to just do this alone.”

So that's been a big lesson for me that has taken a while to learn, yet another thing to credit Sam with.

Some of the best leaders, when you look at history's greatest entrepreneurs, you really think of them as teachers, and they understand they need to repeat, repeat, repeat. I always say repetition is persuasive. You gave me that great Catholic saying: “Repetition does not spoil the prayer.”

I think of Jim Sinegal, the founder of Costco. He has this great line in the book, a biography of his mentor, a guy named Sol Price, who was basically the most influential retailer of all time. Jim Sinegal was mentored by him. Sam Walton took more ideas from him than anybody. Bernie Marcus got the idea for doing Home Depot from Sol Price. Jeff Bezos took ideas from Sol Price. It's just incredible how influential this guy was, and most people don't know who he is.

In that book, he says that if you're not spending 90% of your time teaching, you're not doing your job as the leader of the company.

Patrick O’Shaughnessy

Mm-hmm.

What he means is teaching what our philosophy is. What is our purpose? What do we do? How do we do it? Why are we doing it? You just repeat it over and over again.

I just did this episode called “How Elon Musk Works,” which is, I think, the most downloaded episode of Founders ever.

Patrick O’Shaughnessy

Mm-hmm.

It's just nuts. What shocked me is that, even though you don't think of Elon as a—he's definitely a singular character. There's nobody else like him that I've found, living or dead. There's usually some kind of historical equivalent of anybody. I haven't found a historical equivalent of him.

You would think, “Oh, he's working on seven different companies at a time. He can't possibly be like this.” He was mentioning that algorithm, that four-part algorithm he had—

Patrick O’Shaughnessy

Mm-hmm.

—that he uses in all his companies. He's like, “I say it so much, I repeat it so much, that you'll be in a meeting and my executives will be mouthing the words along with me. They know what I'm about to say.”

Patrick O’Shaughnessy

Hmm.

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

Patrick O’Shaughnessy

Hmm.

I think about that a ton. Repeat, repeat, repeat.

Patrick O’Shaughnessy

Yeah, the joy of that sort of thing and that sort of leader. 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.” I find that saying that maxim to the right person—the kind of person I want to spend time with—their eyes go wide, and they understand it immediately: the reward for great work is not money, power, or fame. It is the privilege to get to do more of this thing that I love doing.

The problem with coming up with good terms for this stuff—we use this term “life's work”—is that immediately everyone else starts saying it, and it ceases to have any meaning. Now every goddamn meeting I'm in is, “I'm doing my life's work.”

My experience is that almost nobody is doing their life's work. Even with 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. It's author of the Declaration of Independence, founder of the University of Virginia—not president. I think that's so interesting.

I think a lot about whether this thing a person is doing is going to be on their tombstone. Usually the answer is no. 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,” is that all three parts are really important.

Say that one more time.

Patrick O’Shaughnessy

A lifelong quest to build something for others that expresses who you are. 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 2 hours. Tell me your whole life story up until the point you founded your company. We'll talk about your company later. Just tell me what got you to here.

Back to originality: best story wins—originality, hardship, transformation. In the business context, I want someone who's lived a very unique path. I find success in startups is often the result of path dependency. Some unique set of lessons and experience led to you being the right person to do this thing. Then hardship, of course. The harder the business is to build, the harder it will be to copy.

Transformation is about the customer. If you build something crazy hard, the customer's life will get way better. I think this powerful concept of life's work can be applied to ourselves to make great investments, and it's really rare, but… The reward for great work is more work.

The reason I started talking about life's work and investing is these people come to realize you will not be rewarded with great work if you do not become a good leader. A common pitfall that I certainly have fallen into before is when there's someone really talented: they can do a lot themselves, and they can get a lot done themselves. I refer to this as heroics, and that's always necessary. A founder always has to be the flame keeper of the spirit of the company.

Founder-led companies are, of course, so much more interesting—preaching to the choir here—than professionally managed companies for the most part. But I do think that becoming a great leader becomes the most important way to secure more right to do great work.

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 you admire personally who stopped?

Patrick 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.

But they're doing something.

Patrick O’Shaughnessy

Yeah. I'm just wired this way. I just need to be doing something. I can't sit around. I'm drawn to people who want to make stuff, and so I have tons of examples of people who have tried lots of things and made lots of things, moved on from things, had chapters in their life, and then started a new chapter doing something totally different.

There's one investor who comes to mind whose name is John Pfeffer, and John has been wildly successful. It's almost like he picks whatever he's doing, and as he gets to the tail end of it, he tries to find the thing in the world that is the most different from what he's doing, which he says with glee requires him to completely abandon his current network because they're irrelevant for it.

One time, he went from being one of the key guys at KKR to being one of the most important guys in cryptocurrency, and then went from that to building a grocery store chain in the UK. Each time, he's like, “I literally had to start from scratch, and I love it. I had to build a completely new network of people.”

I know lots of people like John who have successfully hopped around. I know your focus is more on people who do a thing for a really, really long time, but I don't spend a lot of time with people who were prolific creators of things and just stopped.

I think they're the saddest people. You're in this infinite game, and there's some set of circumstances that causes you to make that decision, and…

Patrick O’Shaughnessy

Here's an example. There's this really fun game you can do 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. Then you tear them up so there's just one thing on each sheet of paper, and you have to, in reverse order, 10 down to 1, slowly throw the roles away until you're left with one. One role left.

It's a really interesting game. It's interesting for yourself, but also super interesting to see what your friends pick. First of all, what's on the list of 10? You can do this with attributes for yourself, too: curious, hardworking, whatever. Then you jettison those one by one. It's a fun game.

I played this with my wife, my kids, and my in-laws one time, and I'll never forget it. My father-in-law had a very, very successful career as an entrepreneur and executive in the healthcare and insurance world. We were doing this game, and his last one was “grandfather.” That was the role that he kept as his final, most important one.

He is an unbelievable grandfather—like the Michael Jordan of grandfathers. He is unbelievably good at being a grandfather. It makes me emotional thinking about it, and I'm so thankful for it. The difference it makes in my kids' lives and his other grandkids' lives is extraordinary.

Dan is his name. Dan is no longer a major healthcare executive. He's still an entrepreneur; he hasn't given it up completely. But he definitely devotes himself more to something like that, which in some sense is much smaller and in another sense is the biggest possible thing you could do.

Even the people who stop the commercial side that I love tend to find something to pour themselves into. In this case, it's the same thing we've been talking about this whole time. It's an act of service: to show up at everything, to be the most reliable, to be the most fun, just over and over and over again—in this case, in the role of grandfather.

I think that's exciting for my own life. Maybe when I'm 70, I won't do any of this stuff, and I'll do something else that's totally different. But my attitude toward it will hopefully be the same, and that will be because I've had 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 pour themselves into what they're doing, regardless of what that role is, even as that role shifts around as life goes on.

You gave me this term that we use to describe people we don't want to spend time with, and I now think I just use it and make it seem like I came up with it.

It's casual. You know, “Do you want to go to dinner with this person, or do you want to meet this person?” As shorthand between you and me, we're always like, “No, they're casual.” It's the exact opposite. That's a beautiful story.

Patrick O’Shaughnessy

Hmm.

I went from pitying these people who don't work anymore to thinking, “That person's better than I am. That guy's a better person than I am.”

Patrick O’Shaughnessy

Honestly, there's something very beautiful about the scope of the ambition shrinking so narrowly. We talk a lot about the trillion-dollar coach. What's his first name? Last name—

Bill Campbell.

Patrick O’Shaughnessy

Bill Campbell. I never met Bill Campbell. I wish I had. It's this beautiful archetype of an older guy who just worked with a couple of executives. He worked with Google and some of the most famous companies, but was apparently transformative in the lives of these people.

It was five people or three people, or however small a set of people, and that's it. He wasn't doing it for money or fame or power or any of this stuff. He was just doing it to help these few people.

I think that's a really cool exercise: What if the only thing I was allowed to do in my life—nothing else was allowed—was help 3 people? Who would they be, and what would I do for them? Dan helping his 4 grandkids, or something like that.

That makes me excited for later stages of life, when I think the ability to do something like that goes up. That is every bit as successful, in my mind and in my book, as Elon Musk or Jeff Bezos—or pick the people that we all worship in the business world.

Of course, I'm amazed by them too, but there are flavors of success. 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, if not more so, because that shit will ripple through history.

My son and my daughter will now behave differently because of the experience that Dan, my mother-in-law, my dad, and my mom gave to my kids. What's better than that?

It is so unusual for us even to contemplate that some of the decisions you're making right now are going to ripple through the generations. They're going to affect things long after you're gone.

Somebody took a bunch of interviews I'd done and stuff I said on the podcast and literally made an 8-track hip-hop album. I think it's called David Senra Founders or something like that. We keep talking about it, but I sent it to Hinkey because the first one was this idea of a generational inflection point.

Patrick O’Shaughnessy

Yeah.

Generational inflection point, which is the founder of the family. Hinkey's rather religious in a way that maybe I'm not, and he's like, he…

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. Somebody just sent it to me. Do you think I’m making music about myself? Come on.”

Patrick O’Shaughnessy

I wouldn’t put it past you.

And so I was like, “No.” And he’s like, “Yeah, I listened to a bunch of them, but that first song...” He’s like, “That’s obviously a sign from God. You should consider it a sign from God.”

Patrick O’Shaughnessy

Mm.

“What? What is this?” We’re on the phone. I was like, “What are you talking about?” The reason that came to mind is because in that song, I guess I talked about—I think it was on your show—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 was 30 years old, living in Cuba, with no education, didn’t speak English, didn’t have money, had 2 jobs, worked in a shoe factory, and was a butcher.

Somehow he realized, “Oh, Fidel Castro. This is probably bad. I have to—”

Patrick O’Shaughnessy

Mm.

“—go to a country where I don’t know anybody.”

Patrick O’Shaughnessy

Not here.

Yeah, I don’t speak the language. And that’s just one choice. Three decades later, whatever, I’m going to be born in a capitalistic country, maybe the greatest country in the world, as opposed to that. That one decision by somebody I don’t remember ripples through entire generations.

Patrick O’Shaughnessy

Mm.

I think this is a very interesting thing to contemplate when you are trying to make your decisions. The last thing on his list was grandfather. What was the last thing on yours?

Patrick O’Shaughnessy

The story was so overwhelming, I honestly don’t remember. It was probably husband or father, one of those two. To me, those are the most interesting roles in life. You and I have talked about how I feel about those two things. It’s probably one of those two, or I probably cheated and said, “Can I have both?” I hope it’s that until it’s grandfather, I guess.

But more generally, maybe this is the theme of our conversation today, the small set of relationships with people for whom I would do anything. That’s how I’m wired. There’s a certain category of person—you’re one of them—for whom, whatever you need, you don’t need to explain it. I’ll do it.

Getting to that point with people, I don’t think it’s that hard. Life’s too short, and there’s only so much energy in a day, so you can’t do this for a thousand people. But you can do it for 10 or 15, following Dunbar’s number or something. You can probably do it for 15, and that is my prized possession.

That list of people for whom I would do anything is my prized possession, and I think that can probably be true for just about anybody. I try and hope to act in a certain way to deserve that group of people. Even if they don’t feel the same way about me, that’s okay. If I’m in their list of 15 and they’re not in mine, it’s fine.

I think that role game is quite fun because it pulls out of you where you have the most energy.

I think this is exactly what we talked about today: why I’m so obsessed with having conversations with people I find interesting, and obviously with people I have deep relationships with. This is why I’m going to 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 where I learned things about you that I did not know.

Patrick O’Shaughnessy

Mm.

And so I really appreciate you saying yes to me and coming, kicking and screaming, onto the podcast. I want to end by turning it around on you. What is the kindest thing someone’s ever done for you?

11. The Kindest Thing

Patrick O’Shaughnessy

One is—they’re related, so I’ll tell them in order. 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 keep unfolding it because there are so many people. I have cousins who are technically my third or fourth cousins but feel in my family more like first cousins.

One of my third cousins was a guy named Tim O’Shaughnessy. When I was in high school, I was a bad student. I was a very good student as a young kid, but I went to this giant high school in Connecticut, with 4,000 students, and I just partied way too hard, didn’t get good grades, and didn’t take it seriously.

I remember one day very distinctly. I was at a friend’s house, having stayed up too late the night before, and my dad called me and said, “Hey, you should probably come home. There are a whole bunch of very small envelopes here from colleges.” I actually got rejected from every college I applied to the first time I applied. I got all the rejection letters on the same day. It was a bad day.

Then I reapplied to some other schools. I had wanted to go to the University of Notre Dame, and I called them and said, “Where are some schools that have a compatible curriculum with yours? I would really love to work hard and then transfer.” They gave me a list. I went to one of those schools, got very good grades, and transferred to Notre Dame.

Now I’m a sophomore at Notre Dame, and I didn’t know anybody. They do a transfer-student orientation, but it’s not like freshman year, where you have all this amazing orientation. For transfer students, they’re like, “Here’s your room number. See you later.” I met the couple of other transfer students, and that was it.

Back to being shy, I wasn’t good at navigating a new social situation at the time. I just wasn’t good at it. Tim, whom I’d met maybe once, was from the Midwest, and I didn’t know him that well growing up. He took it upon himself to come meet me, to find me. I remember very distinctly that he brought me a fake ID.

He went so out of his way for the first 6 months to transplant me into his social circle. Maybe Tim owed me a beer or 2—a couple nights out and a beer was his obligation as a family member—but instead he would call ahead to his friends and say, “I’m sick. I can’t go out, but Patrick’s coming out. Can you just show him a good time?”

He did that over and over and over again. He literally 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. I met my best man and the only other groomsman in my wedding who wasn’t a family member.

Through this act of over-the-top kindness, there was nothing in it for him. He was just doing the right thing. It set me up for the rest of my life.

Which brings me to the second thing. My first night at Notre Dame, Tim shows up with this fake ID that says I’m 5 feet 4 inches tall, with blonde hair and blue eyes, and we go to a place called Boat Club. It let me in with this fake ID and was shut down permanently for letting people in with that sort of fake ID 3 weeks later. May it rest in peace.

I walked into Boat Club, and the story of meeting Lauren, my wife, is that it was my first night at Notre Dame, the first bar I walked into, and she was the first girl I talked to. That is a crazy stroke of divine luck or something.

It was lucky because I was 19 when I met her. She was 20, and we’ve been together, married, and have had kids ever since. The true answer to kindness is her, because for 20 years now, we’ve just crossed the point in our lives where I’ve been with her more than I haven’t in my life.

That’s so crazy. 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 matures when you’re 25 or something, so I had 6 years with her where I didn’t even have a fully developed brain.

It’s by far the number one blessing that she—yeah, we created this life together in a way that I mean... The 1,000 things, the 10,000 things that she’s done that add up to those 20 years are 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. I love this story and this question because whole lives are downstream of simple, quick acts of kindness.

Without Tim, my life doesn’t look anything like what it looks like today. All the things I care about most probably don’t exist. I remind myself of that every day, which is why I love asking this question.

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.

Patrick O’Shaughnessy

Thanks, Patrick.

Thanks, buddy.