未発見の才能に光を当てる——パトリック・オショネシー

Mhm.

Yeah.

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

Oh, that's funny.

I love that episode. Yeah.

whoosh all the way down just like no no no no no. But that is such an unusual instinct if I'm being honest. Like I don't think I would have done that. What the hell was going on there? You didn't see it as a competition. You didn't What What was What was happening?

You said before you were cha some chasing something, right?

I'm not chasing anything. I think it might be an interesting conversation today to talk about our, you know, how how we view what we're doing in in slightly different ways. But I have no goals. I'm not a goals person. I I I've written essays about not having goals. Um the most read thing I ever wrote back when I used to do a lot of writing was about uh it was called growth without goals. And so I'm not chasing any particular thing. I don't have a big hairy audacious goal or something like this. I don't want to put someone on Mars like Elon Mer. Um, and I'm not to say not to say that that's a bad thing. I think some people are goal oriented and that's awesome, but that's not me. And uh, 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 um, called inventing on principle. Have you seen this?

Yeah. You were not

You were just something that like came out of the left field. And everything interesting I've ever done came out of left field. And it's which is why I don't keep long-term goals or short-term goals is that opportunity just I'm very open to opportunity along this principle and and so I'm very enamored of this idea for how to live. Having Patrick as one of the first guests on my new show was very important to me because of the role that he has played in my life and the quality of the product that he puts out. His podcast, Invest Like the Best, has taught me so much and has made my life better in the more than seven years that I've been listening to it. Patrick and I both have a deep multi-year partnership with the presenting sponsor of this podcast, Ramp. And I think there's a lesson in there that is applicable to anyone who's trying to make something great in the world. The founders of RAMP know, just like Steve Jobs knew that you always bet on talent. The founders of RAMP wanted to be associated with the podcast that they listen to, enjoyed, and benefited from. They wanted to bet on talent in everything that their company does. To Steve Jobs, this was mandatory. Steve once said, "You must find the extraordinary people. A small group of A players can run circles around a giant team of B and C players." And so, you must build a team that pursues the A players. And this is exactly what Ramp has done. Ramp has the most talented technical team in their industry. Becoming an engineer at RAMP is nearly impossible. In the last year, RAMP has hired only 23% of the people that applied. This means when your company uses RAMP, you now have top tier technical talent and some of the best AI engineers in the world, working on your behalf 24/7 to automate and improve all of your business's financial operations. And they do this on a single platform. RAMP gives your business fully programmable corporate credit cards for your entire team, automated expense reporting, bill payments, accounting, and more, all in one place. The longer you use RAM, the more efficient your company becomes. This is important because as Sam Walton said in his autobiography, you can make a lot of different mistakes and still recover if you run an efficient operation or you can be brilliant and still go out of business if you're too inefficient. Ramp helps you run an efficient organization. I run my business on RAMP and so do most of the other top founders and CEOs that I know. I hear from people all the time that listen to this podcast that have switched to RAMP and rave about the quality of the product. In fact, Matt Pollson, the founder of Marketby, just sent me a message. He said that RAMP helped him save $420,000 in monthly expenses. Make sure you go to ramp.com today to learn how they can help your business save both time and money. That is ramp.com. At what age did you stop having goals?

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

there's a great line from Alan Watts that I always think about he's People think that life is meant to be understood and it's like no life is meant to be experienced

I don't know if it was Alan Watts that said this. Uh he was he had such a way with words that maybe it was him. Um it might have been Joseph Campbell, but something to the effect of um we're not searching for the meaning of life, but for the feeling of being alive. And I think that's correct. And I think a great uh if you play red light green light with principle as you search for your principle, I think you could do a lot worse than knowing you're on the right path if the thing makes you feel more alive. Like if you go in the direction and people know what it's like to feel alive, they can call to mind these moments in their lives where they felt the most present and alive. And using those as a signpost to what your principle might be or what you should be doing, I think is a really a really great thing. And that's certainly how I I remember that line reading that line 15 years ago as well. And then starting to chase the feeling of being alive, not not a goal, but just that feeling. And um everyone can answer this question, by the way. It's a really it's a great way to have a conversation with someone is to kind of feel ask them where they feel this and and then also why they're not doing more of whatever the answer happens to be which is a funny funny circumstance of humans that they kind of know what makes them feel most alive and then they don't do it most of their lives.

Usually it's it's it's simple which is um fear. fear that by pursuing an original path, I have this idea that uh the best story always wins. And I sp actually spent the last couple of months like really trying to figure out what what what do I think best story means? And the best principles for a great story that I could come up with were originality, hardship, and transformation. And if you dig into originality, that one is really interesting to me because people don't pursue original past usually because they're fearful um of the unknown because an original path by definition means it's all going to be on you and that's uncomfortable and hard. Um, and because an original path usually means leaving a very comfortable current existence in a way that's scary. And so I think when you really drill people on why not, um, they'll give reasons that add up to I'm I'm afraid and that's hard to get over.

It definitely helped me find it because I wanted to not waste life. When I was a little kid, young uh 5 years old or whatever, I had I had this just crippling fear of death. Like I remember my mom and dad would have to like sit and hold my hand for me to fall asleep at night cuz and and the reason was I would just sit there like spiraling on this crazy idea maybe this is why I studied philosophy that like someday I would not exist and that just freaked me out and did for decades. So that probably kicked off this introspective period of my life where I was very curious about philosophical traditions and religious traditions and metaphysics and all this kind of stuff because I wanted to know what the hell is the point of all this? Like what's the point? What's the meaning? What's the purpose? And otherwise it's just terrifying, right? That we're here for a blip and then gone. Just terrifying. I try not to sit down and think about it too much. In fact, I'd like to move on. [laughter] But that kicked off this period of yeah I wanted to understand myself and others and so I was very introspective and of course that made me want to not live a dull life and I was very scared of just like living this train track existence. So yeah it did help a lot but interestingly once I have clicked into I think understanding what I want to do I don't think about it at all and now I have very little introspection left in my life. I used to be so obsessed with all of these personality tests and what they mean and psychology and um seeking and like all the modern methods for doing that

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

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

Like what is their interpretation of like their view of me that is different

Your organizing principle? 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.

Okay. And my principle is that is when I do it is my obligation with nothing maybe I invest maybe maybe I end up benefiting but that's not the point that it's my obligation to tell people about it and to help foster it into existence. Um so you know important difference. Well it took me a decade to state my organizing principle. I'm not going to be able to name yours in a minute, but you're probably the most single-minded and devoted to what they do person that I know in the sense that most people that have achieved uh a level of success in their field or in their job that you have begin to branch the world when that happens pulls you into this branching exercise where you end up doing a lots of different stuff. uh and that you know you end up monetizing in different ways or going into different lines of business or changing how you do things expanding the single-mindedness that you that you have is quite distinct from the people that I know and um you know why are you doing it I I mean I think you've talked about this certainly in private with me but also in public about you know you came from we came from opposite circumstances like I was I was born on proverb a real third base or sliding into home. I come from a history of extremely successful entrepreneurs. My great-grandfather who had the best name ever, his name was Ignatius Alawishas Oshanaugh. Everyone called him a he was I think the 13th of 13 kids. He was one of the richest men in in the United States. He was an oil wildcatter. First first oil uh hole he ever drilled. I think still pumps oil to this day in uh in the Midwest. And so he was a giant, he was broken up in the antitrust, you know, in the Rockefeller antitrust stuff around Standard Oil. And our family takes great inspiration from him because he made this fortune. He did not give a … about money. Uh he didn't really spend it. He gave away basically all of it in his lifetime, mostly anonymously. My dad tells the story about being at his funeral when my dad was 11 and all these people were there and no one knew who they were. And my dad would go up to one and be like, "Who are you?" and and they would say,"Well, Mr. IIA, you know, I cut his hair and he put my kids through college and bought me a house or Mr. IIA did this or this this and we didn't even know where it went." And I have benefited from this tremendous history of business success in my in and around my family forever. Whereas you came from an op a very different set of circumstances. Our friend Sam has this idea of um there's founders of businesses and there's founders of families. And I think of you as the founder of your family. And I think that's incredibly powerful and I think it's your greatest accomplishment that uh things repeat through the generations. You're fond of saying the story of the father and the son, you know, are the same. And it takes tremendous um character, willpower, talent, lots of stuff to break from that family tradition and go a new direction, which you've done, which I just think is remarkable. And I don't know if that's the underlying why that you refused to let your family continue to go the same direction that it had gone up until you were born. And um you went, as Sam would say and we've talked about, you went searching for mentors cuz you didn't have them in your life. You found them in books and in founders. And you've been telling everybody about it ever since. And it worked. It worked for you to change your life. And now we know based on your work that your work is now changing other people's lives in that same way that you changed your own first, but you were the first beneficiary of it. And so what is your principle or why? I don't know. Maybe it's that you can you don't have to just keep going the same direction that you were given. You can break off and and found something new. Um I think that's pretty amazing.

This is also like you know I use podcast for this reading mainly. It's like I think people are rushing through things too too fast. You know, I'm famous for only listening to podcasts on one X. Everybody's like, "Oh, you read a lot. You must read fast." I'm like, "Yeah, 25 pages an hour fast." Like, I'm not speedreading here. I think I want understanding. And like I want understanding of how things actually are, not how humans say they are. And humans, not only are we lying to ourselves constantly, which is if you're lying to yourself, like of course you're lying to other people about like why you're doing what you're doing or what you're doing uh what it is that you're doing. And this is why like autobiography is a biography so much because in many cases the person's like long past dead or they're older and they're just like I'm writing this book when I'm 80. like I have no I'm not incentivized to to lie and like here's the stuff I went through and the trouble with whatever being what kind of dad you are trouble with women trouble with business but you realize like there's nothing that you're experiencing that somebody else hasn't already experienced and so what I want is like true understanding of like humanity as it is human nature as it is and the world that we're creating and then I use their stories it's not really about them. It's like about you. And I think this I don't think this has nothing to do with me. I think like when you watch a great movie, you hear a great story, you hear a great song, you're not thinking about like, oh, this happened to Taylor Swift. You're like, oh, I had that same experience in this relationship or I went through this exact same thing. And it's like a form of understanding like I'm in the middle of this right now. We were just having lunch upstairs and you know essentially like I'm just like in the middle of like trying to find the story that I want to tell with this book that grabbed a hold of me for 6 months. And I told you about this is Bruce Springsteen's autobiography. I'm not I don't even listen to his music. And I told you about this right like right when I was like there's stuff in this book that like this dude looks like he crawled inside of my mind

it's invest like the just the the the title is passion and pain and you know people are always like oh like did you guys sketch this out? I was like no Patrick doesn't sketch things out like that. He's like I we built a friendship. I want you on the show. Like I don't think you told me anything we're going to talk about. I do remember you texting me a few hours. We're supposed to do it at like 10:00 a.m. You're like hey I got pushed back. Can you do 1 p.m.? I'm like oh no my brain only works in the morning. So I took like a quick power nap and I'm in this booth. We didn't do video, but you can see me. And I'm in like this phone booth that I put in my house that I was the only person. These phone booths are all in these offices and I had one. They came and delivered to my house and like, you know, we've never delivered to somebody's house before. I was like, this isn't a phone booth. This is a podcast studio. This makes perfect sense to me. Um,

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

I'm going to tell you right now, but it was an incredible dinner the first time we met and you know it was unexpected uh requested by them and 3 hours into this person's like I have told you things no one else knows about me the very first time I met them. there just I just I have no I have no interest in the superficial and I think you have to talk for a long time because it takes a little while to get like warmed up and like feel the person out and this is why what you said earlier is so important like fewer deeper relationships dude think about the crazy conversation which we're not going to you know relive but like me and you just had an insane 2 and 1 half hour conversation at in Tel Aviv at like 2 in the morning

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

and either you haven't applied it or you forgot it or you did it for a little bit and you need a reminder. This is why you mean me and you always describe founders like it's church.

in that church. I think the animating interesting question is you read these stories all of which back to my my idea of originality hardship transformation you know best story wins that uh originality is you're inspiring people to wonder what's my thing everyone's got something I guarantee it like it's my favorite thing to search for in conversation especially if someone's not yet doing it which is kind of the same the same search for un unrealized potential or something everyone has a thing that for whatever set of reasons their life experiences, how they're wired, their naturally endowed gifts, and searching for that thing is really interesting and really hard. And I think that's what founders continues to do for me is show me examples of people that went to the trouble to find their thing and then once they found it, foster it the rest of their life. And again, once you find your thing, the second thing is hardship. It's not supposed to be easy. Like nothing meaningful is easy and that's fine. And and then once you learn that, I think that's when it gets really fun is that the m I always I always have this feeling the second something just feels easy and I'm kind of going through the motions, I get really uncomfortable and want to try to push myself in in some new way. Um, but I think that's what Founders does so well is it shows it's what back to the very beginning of our relationship and why I sent that tweet out and why we talked to each others for an hour the first time we talked. It's because it was so unique and so different and inspiring. Um, so I think it's a powerful thing to do for people.

You mentioned, you said organizing principle, uh, which I think it's I think that's correct. Just to push because this can now be something we talk about for the next couple of years, which is probably how long it'll take to articulate. That's different than what is your principle for invention. So, back to the idea of inventing on principle. The principle should be something that when you see it violated, it is your obligation to go correct it and that that correction is an act of service for for other people, not for yourself. It's not about you. And that's what makes the idea so powerful. I agree that that's your organizing principle. That's like the thing behind why you're doing what you're doing. It will be fun to try to pin down what the principle is for invention because that's what you're doing. for making new things, which is the most fun and rewarding experience of a lifetime. And I remember the the the little opening quote in this compilation of his life's writing by Joseph Campbell that was done by his niece or something. The little opening quote in the book is the privilege of a lifetime is being who you are. And the people that make things that are the most interesting, those things are a reflection of themselves. That's the most sustainable form of creation. If you can sort of spill yourself onto the thing you're making which benefits others, the thing you know being of service to other people in some way. I think that's the thing that we actually I think that's what we're all after. I think what we all want is to make participate in the act of creation on a in in a small way that reflects the act of creation going on at on a grand scale and to have that experience of in so doing by pouring oneself out into the thing and then having the thing be of service to others. That's a that's an amazing feeling and it's hard to get going, but once you do, I don't know anybody I've never met anybody that's gone that's had that experience and gone back. Not one. And it's because I think it's the thing that we're we're all after. And that's what you're doing too with this show. I think like one of the biggest things I want to avoid is like finding the thing, doing the thing, being great at the thing, and then like something you do causes that to stop where like, you know, I'm kind of obsessed with like this sained success. Uh, you know, like I don't want to, you know, have this huge spike. I don't want to flame out. Like I'd rather just do like this slow build decade after decade, get better, and like keep doing it. This is why essentially I read fiction and I read biography like that's basically what I read and like the biography part is like okay what happens after they got what they wanted and the conversations I've been been having a lot of these have been having uh on camera but after off camera I'm always asking because most of these people are older and more experienced and obviously more successful smarter and everything else just like what what do I have to worry about like what am I not seeing that could like cause me to stop like I like what I'm doing I love What am I doing that would cause it to like for me to not be able to do that?

Well, the trap is before you do the work to figure out the thing that makes you feel alive. There's this great line in the um in the panachads that it's always referred to abiding joy. Like joy that doesn't doesn't run out. You don't use it up like you use up so many resources. As you use it, you get more of it. That's abiding joy. The target for most people becomes the traditional money, power, fame because those are worldly proxies for success that we all recognize and are for sure to some degree true. It's hard to get a lot of those three things without being successful in some way. I think those those things are huge traps because they become once you start to get one it's the thing you start chasing and it's different than chasing the feeling of being alive that abiding joy of feeling alive that we talked about earlier which you'll never run out of that that that will always guide you well always and money power fame will not and so I think the answer to your question or your worry is just like make sure you're chasing the feeling of being alive and that the intuition around that and you'll be fine. And it's when we it's when we get sucked and I've of course have just like everybody else like I've been intoxicated by those three things at various points in my life and that's because they're intoxicating. It feels really good the first time you have a lot of one of those things.

and it's like three things health work relationships and I can't think of anything else that I care deeply about health has to come first because if we are sick or we have no energy like we can't do anything else but other than that like if you look at like how I spend my time it's essentially just like I'm building I'm creating work that I hope it makes other somebody else's life better that I truly am like the abiding joy like uh chasing that and then I'm just deeply interested in a shocking way of like having really strong relationships with other people and like I was not like that 10 years ago.

Yeah.

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

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

And what he realizes is that's not what I actually wanted. And what he this is what it goes by. Hey, I I think I told you this upstairs or maybe I even mentioned this. like had a very interesting conversation at dinner last night and it started with what is the lie that you're telling yourself and me and another person going around that for quite a while and it was very fascinating and the lie that Bruce was telling himself was that work was the most important that becoming a rockstar was the most important fame was the most important and what he realizes that his parents had so messed up his emotional well-being he was incapable of doing the thing that he wanted in his He wanted desperately wanted to have kids, to be married, to break the chain like we mentioned earlier of like my kids will not experience what I he experienced.

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

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

and they just assumed, oh, he's got no coat, he got no money, he's like running to warm himself up. And then the summer comes and he's still running. And obviously Robert Carter was a master with words and storytelling. And his whole point is like of course he was running. He like finally made it to the spot cuz he was talking about he wanted to be president like third grade or something. He's like he finally made it to the city to the spot of where all his dreams are. And like he was going to run after his dreams. There's so much in between these two stories. One guy's a rockstar. One become one guy becomes president of the United States. And it's the same thing. One is generative. One is unbelievably manipulative. then, you know, probably not a guy that you'd like want in your life to be around. And so, I think also learning from like great examples, but almost like seeing like, oh, I don't want to be that way.

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

This conversation is now therapy for David.

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

Let's take one like just some of the most important ideas and where they came from. to take the the simplest example possible in the early days of the show. This is a very like practical real world example. Uh if you take the ideas that I got from Daniel who you mentioned before at Spotify about how to build software uh from Brett Victor who I mentioned before about this principle for great software and what it looks like and from a guy named Chaan Pudigont at Benchmark uh one of the partners at a very storied investing firm called Benchmark who taught me how to sell software. just those three guys. I basically just stole their ideas and applied it to my situation and it worked to a spectacular degree. I didn't know anything about software. I'd never built software before. I had an amazing team at the time that, you know, was able to pull it off. But the direction of the resources and what to do strategically just came from asking, you know, those three or three of the greatest in the world at what they do. uh how do I do this to somebody that could help me and then not thinking too hard about what they tell me and just doing it and having it work and and so there's a tiny example, you know, three people and and

Um two I've never met Brett.

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

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

You try to email the Aman in New York and ask them if they let me set up and film a podcast here for free. That's not going to happen. And that happens because of the relationship, a personal relationship that I have with a friend of mine who it like is involved with Aman. This is why I would say like relationships run the world. And our jobs are essentially like learning and then taking what we learned and packaging it for the consumption of somebody else and for an easy way for somebody else to consume and benefit from that learning where it's a conversation, a book review or whatever the case is.

Yeah.

Two people came to mind uh right away. Uh the first is Herb Allen from Allen and Company who I don't I don't know well. um these lessons came from one incredibly, you know, incredibly interesting conversation about I my sense of him, again, don't don't know him well, is that he is uncompromising in his values. He he does he's maybe like the apex predator of like the thing I want to do, which is like picking and supporting people.

Munger said, u I'm paraphrasing, but he's like, you know, one of the best ways to learn is like you find somebody that's like kind of an outlier, and you just ask like what the hell is going on with this person. Yeah. And you just keep asking that question to try to get like deeper and deeper and deeper, but like reverse engineer of what they're doing and like why uh they're they're really successful. There's another fascinating thing where like everybody there's like this meme where it's like everybody has a podcast now and everybody starts podcasts and as soon as that like takes hold. You've been doing podcasting for 10 years and you decide no I'm going to go in a different direction and the majority of our conversations I would say now are not even about the podcast. They're about these profiles

on Colossus. Some of them have been so incredible that I actually used them as source material for a founders episode, which I think we should do more of those collabs because that was like they're like really well written, kind of like doing my job for me.

Why did you decide to do that? I'm in the abstract very interested in how can I create and control valuable scarce units of attention and then dole those things out to the people that we believe in at a very high level. Uh the reason we now have a magazine which on its face I think was a everyone would have agreed was a stupid idea or told me it was a stupid idea when we started it. um why are we doing these profiles that take months or quarters or years to write um 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 like podcasting on people that we admire um and to teach someone teach the world about a compelling founder or a compelling investor or or artist or whatever. And the thing that I didn't realize would that was was that because I'm not writing the profiles, our amazing team is writing them. It would actually be a double whammy that not only uh when we started doing this, I went and read David Remnick, who's the editor, longtime editor for the New Yorker, and New Yorker profiles were were always my favorite growing up. These incredibly detailed uh amazing well-written profiles. He wrote in the introduction to this his compilation of his favorite New Yorker profiles. There's this line that says, "The best profiles over the last hundred years are are defined by somebody doing a thing they're obsessed with and a writer that is as obsessed with the person as the person is with the thing." And I remember reading that paragraph and just thinking, "Wow, that like I want to read. That's what I want to read." And um you know so I went and I read a million profiles and the very best one I read was in a a publication called tablet on on Palmer Lucky from Andre and I reached out to the author his name is Jeremy Stern who's now the editor-in chief at Colossus and you know the rest of that story is sort of history. He he joined. We've got other people, you know, that have joined or are joining to write these profiles. And it just felt like, wow, this is another way to do the thing we love to do, which is to find the person, become obsessed, learn everything about them, take great time and pain to write a definitive thing about them, and then share it with millions of people. And you know, the fact the one that we wrote about um Josh Kushner and Thrive was one of these like bizarre break the internet moments when it just like completely took over the internet for a while. And I remember reading it the first time and I was like 45 minutes into reading it and I was still reading about the Holocaust and um 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 the soil out of which his family and eventually he emerged. And Jeremy also the writer was the product of Holocaust survivors himself and knew a tremendous amount about Josh's family history because it was also his family's history. And I thought that was the coolest most beautiful thing. I never would have I would you know so this this project has become an excuse to uh first of all find more talented people the writers that we can support which is great see the see the potential you know same thing we've been talking about over and over again. So now now team members become more people that we can do this supporting thing with and for them to write things they're obsessed with and passionate about and then for the rest of the world to benefit for the people being profiled hopefully to benefit you know if we tell the honest stories and and you know we want to tell the hard parts and the and the interesting parts and it's been successful beyond what I ever could have imagined. And I think it's important to note like when I started with the first idea, everyone said it was a stupid I mean literally everybody said it was a stupid idea. When I started the podcast, everyone said it was a stupid idea. When we started Canvas, everyone said I think like if people say something is a good idea, I always get a little nervous because if it's if it sounds like a good idea, it just feels you're in a more competitive space. It's going to be harder. I think the key is stuff that sounds dumb but isn't. Uh and I think that's what I would, you know, starting a magazine in 2025. I think falls in that category of sounds dumb. Magazines are dead or dying. Um, but the thing underneath it was this desire to have more ways to do the thing that we love to do, which is find people, learn about them, tell the world about them. I suspect it won't be long until that's much bigger than even the podcast, which itself is, you know, very, very big. The surprising thing is I think you want that to be the case.

Colossus being bigger than the podcast.

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

I know you I know that

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

so I can enjoy them more and I'll I'll get to enjoy it just like everybody else. Like, I can't tell you how fun it is to get the first draft of one of these things in Slack. Like the things that make me the most giddy in my work are uh 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 like it's the same like deep investigation publishing writing clear thinking. Um when I get one of those two things in the morning often sometimes there's days where I have several of them those are the best days. And so selfishly, I would just love a world where I'm not needed at all. Um because that means we're creating more of them. Obviously, I'm limited by my own bandwidth and time. Uh I'll always do interviews. I hope that they I hope it gets bigger and bigger and I I don't want to like fade into the sunset, but I hope this is much bigger because that means I get to hire more incredible, talented people and hopefully put them on a career trajectory that's the best it could possibly be. And that's incredibly gratifying. I get to read more of these things. Um, I get to do this thing that we love to do for more people and point this point the light that we're trying to cultivate on more and more talented people. That that's like unbelievably exciting. I hope it's not just writing. I hope it's documentary. I hope it's who knows where it goes. I hope we start convening people in small situations where meet this person, meet this. Like that to me is the most fun thing in the world. And so a world where it's no longer rate limited by my time and energy is much more exciting than a world where it's me. And so yes, I would vastly prefer that all the rest dwarf whatever I do, even though I hope what I do lasts forever and is big itself.

You know, everyone's launching a magazine. It's gonna be like podcasts.

where like people have been reading like you mentioned that I bought that book too that you told me about the New Yorker like people have been they're always interested in people. I remember reading um

and he thought it was like really good and he didn't like the fact that Oracle he had no media strategy for Oracle and he's like uh 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.

what is it

Well I don't know I don't know what it's called.

There you go [clears throat] forever. All my vocab comes from the written word. So, you know, everybody makes fun of me cuz all my DMs are like, you mispronounce this word. It's very obvious, buddy. But his whole point is like, I don't want to be associated with these people. I want Oracle as IBM or Microsoft. And so, he's like, the way I'm going to do that is I'm going to pick a fight with Bill Gates and Microsoft. And he does this huge fight.

So the reason I bring that up is because people are fascinated with profiles of other people. We are fundamentally more interested in other people and like what they can teach us about ourselves anything else.

and maybe we'll write something in 10 years, you know? So things that are really hard to make are really interesting to me. And I think people stopped doing profiles because they're really hard to make. They take time. The business model kind of sucks. like the the pay is terrible. You know, profile writers are not paid well. Um the world went a different direction. It's much cheaper and faster to make a stupid … Tik Tok than write a 50page profile about someone that's careful and intricate and well written. And I believe you and I certainly talk about this all the time. The world is desperate for some stuff like that. The world is so sick of this crap just all day, every day. It's just crap. And it's it's everyone makes the junk food comparison because it's a perfect comparison. Like junk food got to where it was because it's been optimized for us to want the most of it possible. Whether or not it's good for us, it's obviously horrible for us. It's the same thing with most content. And everyone knows this in their gut and we all want something more carefully created. And I think profile might be perhaps the ultimate expression of that. If a documentary is like the ultimate profile, maybe that's even harder than writing a profile. But um yeah, I'm interested in stuff that's very hard to make and that's singular that can't be easily copied. And uh I mean the literal answer to your question, it's kind of funny was somebody uh I'm actually seeing seeing him Monday gave me the idea to potentially buy this existing magazine. And um we we didn't buy it because I like to create our own things primarily. But it was notable to me that this magazine, which had been around for a long time, had all these incredible I'd never heard of the magazine. And it had all these incredible people on the cover. And I thought, "This is strange." Like, "Why are these people doing this magazine that no one's ever heard of, big names?" And it it dawned on me. I was like, "Oh, it's the cover. Like, people can't say no to a cover." And so, I tested that theory out and and it was true. And I think what that means is it's like the ultimate form of spotlight and attention that you can give to somebody. And so that that's what got me actually literally spinning on like, oh, maybe we should I would love to have a cover that I could dole out.

People vastly underestimate the important of volume.

visit to Rick Rubin's house

and he's been in the same business. He's worked with all these different musicians. In fact, he said something that was interesting to me. I actually screenshotted it, saved it, and I reread it on my phone. And he talked about that the most obsessive artist he ever worked with was Eminem, which is like, wait a minute, that's you worked with everybody. You've had a four decade long career. Like, why is that the case? Like, that makes me want to know more about that. Uh, our mutual friend Brent Bashore told me, it's a hilarious story one time. You know, Brent's got he owns a bunch of different companies and sometimes those companies need a CEO and he found himself, I think, at like a lunch or dinner with Charlie Mer. And so he's like, you know, I'm this young guy. I think he was probably like 35 at the time. I own these like 12 companies. How, you know, how do you and Warren find like great cos and Charlie's just like we just find somebody that is a great co and say come do that for us. Yeah.

Yeah. Yeah. People show you. And um it's that I think that also if you invert that to use another mungerism, it serves as great advice, too, which is if you're trying to get ahead, put stuff out in the world that people can find. Hanky would call these breadcrumbs. put stuff, put breadcrumbs out into the world so that people see it and are amazed by it. Like if you create a single thing, not you don't have to do 10 things, just one thing that people are amazed by. Put it pour a year of your life into making one amazing thing that people are amazed by and amazing things will happen. I promise you. Like the the internet is amazing at sharing something that is great. You say there's always room for great. Yeah.

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

Yeah.

traveling caries.

Um, and like that's a great filter for like finding, you know, new things to create in the world.

Still really good.

Yeah. I think it was beautifully said we haven't even touched on investing which Is it seeing red? What did this person say about you? Okay. Red on the color wheel. Can you tell that story? When you just said like this all started from because I had I like love to read and then that started this whole chain of events and now you have this other parallel thing that you just do compulsively that you can't help which is like exactly what you said. I'm doing 10 invest like the best episodes a day. I'm just recording, you know, I'm doing 50 a week and I'm just recording one. Like if we're in a group, I know what's going to happen. You're just going to start lighting people up with questions. So we go on this 5 hour walk, which Sam did not like, by the way. [laughter] People don't know that you're like a goddamn billy goat, okay? Like I It's just you you walk way too fast. You don't go around obstacles. You just go straight over them. That's why I call you a billy goat because they do that in real life. Like you know if you're out in nature and usually people there's a mountain here like I'll follow the trail around it. It's like no billy goats just go straight over and up and like that's like walking around with you. Columbia, Missouri of all places. We go on this like 5 hour walk and essentially it's a 5h hour private invest like the best episode except you're interviewing both of us the other person questions about the other person who's like really actually was like really impactful and important for me to understand myself because again like You know that person wants the best for you and they're telling this about you, you should even if you don't agree, you should think about it for a little bit. And I've [clears throat] thought a lot about what he said in over the years and I definitely agree like he he was right. So I don't know how this got turned on you, but that's when he said Red on the color wheel. Yeah. Well, first just a thought on Sam, which is it's hard to imagine a higher compliment I can pay someone than the role that Sam plays in my life. Uh the way I would phrase it maybe is I have more conversations with Sam when he's not there than when he is. What I mean by that is I'm often finding myself wondering in a in a situation like what would Sam think about what I'm going to do here? Um, I so value his character and judgment and fidelity and and just so many things about him. But like what a role to play in somebody's life. Like he's the one I invoke in my head. One one of three or four people that I invoke in my head of like what would this person think about, you know, this thing I'm about to decide on? Um, but back to the story. So he said uh yeah it was something like what's my biggest weakness and he he described me as being red on the color wheel which uh he explained meant that uh when I'm interested in something I I am intense like and I've always been this way. I am voracious and intense and aggressive and uh I would say I have a skill at making things happen when I'm interested in in in them happening. And maybe that's one side of the sword. The other side of the of being red on the color wheel is this like locked in intensity. The other side of it is that like the moment that attention is is is focused elsewhere, This is known lovingly amongst your friends as your eye of Sauron. in some cases it's like a physical presence thing. It's not just like I can get you on the phone, but I was like no no this is not good enough. So that's the strength your strength can be your weakness. we were at Brad Jacob's house having breakfast. He was very disturbed by this. He tried to fix it. Um, so anyway, the the the the other side of that sword, it freaked me out that I couldn't see anything with my eyes closed. But, uh, the other side of that sword is like when I'm focused on something like like here right now, I am not thinking about other stuff. Like, it's just all this. I'm I'm I wish it wasn't the eye of Sauron. That sounds so bad. But it's said in a loving way. 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 uh fund and we I was going to be an investor in the fund and uh so he called me and said you know putting this fund together it's small limited group of people I'd love to have you if if you want to do it. Hell yeah, I want to. Of course. Um, and told him the amount or whatever. And then he called me back like a month later and was like, "Okay, like I have the docs already and you know, we're ready to go." And uh, you still in for this much. And I said something like, "Well, I can't. Yes, I'm still in, but I I can't do that much because actually like I I have also launched a fund." And he was like, "What?" and and I said, "Yeah, you know, I need to make a a GP commit to my own fund." And so I'm, you know, this is before I sold my business. It's a little bit, you know, tighter situation. And I have to reduce the amount. And he he started to tease me because he was like, "Wait, so when I first called you a month ago, you had never even thought about having a fund. I've never heard you talk about that. I don't think you'd ever thought about it. And now a month later, like you already have a fund. like a month later like it's raised and done and um I think that's a good example of like yeah some opportunity came out of left field. there was this investment opportunity in one company that led to a fund very quickly in the summer of 2020 and um so yes I I I like to move really really fast when I'm interested in something but my interest does shift around and um I don't think this is a good thing by the way like I I I don't want to whiplash people and and I realized thanks to Sam that I was whiplashing people I would be so excited and willing and able to galvanize people around an idea And then I would change my and this still happens but I would change my mind and completely forget about the idea back to like people that have this lack of visualization thing also have quite bad event memory. I don't ever think about stuff in the past like ever. And so I not only can I change my idea but I literally never think about that thing again that I was so passionate about in the moment you know for a short period of time. And that is jarring for people you know that are like signed on to do a thing and then a week later you're like what are you talking about? What thing? like we're doing this thing. And [snorts] um so I' I've worked pretty hard to narrow the uh simplify my life with rhythm and harmony, focus on fewer things, like get less distracted by what I would call like the flavor of the month club, which is something that that can definitely snare me for sure. Hey, real quick. I need a favor from you. Right now, I'm conducting a survey to better understand the listeners of this show. So, the survey is entirely anonymous. It's going to ask you things like what your position is at your company, what your household income is, things like that. This information is going to help me both keep and attract the best possible sponsors for the show, which then in turn allows me to create the best possible conversations for you. Now, I don't want to just ask for something without giving you something. So, as a thank you for completing the survey, I'm going to host a live stream on YouTube where I talk about some of the most important things I've learned from spending hours with the guests on this show and some of the best ideas that they have shared with me after our conversation. So, please do me a huge favor and complete the survey. Takes just 5 minutes, probably less than 5 minutes for you, but after you complete the survey, I'll email you a link to the live stream. A link for the survey is in the show notes of this episode and is also available on davidenra.com. I heard Ari Emanuel on your podcast say something that was like actually pretty smart where he's like his idea of like when especially when he's trying to do a deal he like overcommunicates with the people that are important to you because then you're not going to have there's no unspoken assumption you know and then if you let it sit there too long then you have another unspoken assumption on top of that one then things can get like really really weird. I think a lot about leadership because ultimately my main job is to back people with LP dollars, lots of them that have been entrusted to me as a fiduciary into companies led by these people that we're backing that are usually pretty early in their company building journey. So you're you're mostly or largely backing the person in the team versus the you know mature business story. and pretty important that that person's a good leader. And I think one of the things I underestimated about lead great leaders that Ravi Gupta who's another person that I would list, you know, and people that have really impacted me. I I at one point I called like everyone I knew. I was like define good leader just I'm going to I'm going to do a survey some of the best leaders like when you see in like company buildings like history's greatest Twitter is like really think of them as like they they they're teachers and then they understand they need to repeat repeat repeat. I always say repetition is perspective. You gave me that great like Catholic saying where it's like repetition doesn't spoil the prayer. So I think of like Jim Synagol founder of Costco. He has this great line in the book, this biography of his mentor, this guy named Soul Price, who basically influenced, he's like the most influential retailer of all time. Jim Synagol was mentored by him. Sam Walton took more ideas from him than anybody. Bernie Marcus got the idea for doing Home Depot from Soul Price. Jeff Bezos took ideas from Soul Price. Like, it's just incredible like how influential this guy was and most people know he he uh he is. And in that book, he says that if you're not spending 90% of your time teaching, you're not doing your job as the leader of the company. And what he is is like means like teaching what our philosophy is, what is our purpose, how what we do, how we do it, why we're doing it, and you just repeat it over and over again. I just did this episode uh called How Elon Works, which is I think the most downloaded episode of Founders ever. Like it's just nuts. Yeah. The the joy of that sort of thing and that sort of leader the the my favorite my you have all these great maxims. My favorite maxim pretty much the only one we use in my business with my team is the reward for great work is more work. And I find that saying that maximum to the right person, like the kind of person I want to spend time with, they their eyes go wide and they understand it immediately. That the reward for great work is not money, power, fame. It is the privilege to get to do more of this thing that I love doing. The problem with coming up with like good terms for this stuff, we use this term life's work, is that immediately everyone else starts saying it and it ceases to have any meaning because like now every goddamn meeting I'm in, like I'm doing my life's work. Um and and my experience is that almost nobody is doing their life's work. Even great a lot of great founders, I would say it's not their life's work. I love the fact that Thomas Jefferson on his tombstone uh has three things that describe his life. But one of them is not that he was the president of the United States was, you know, author of the Declaration of Independence, founder of the University of Virginia, not not president. And I think that's so interesting. Um, and so I think a lot about like is this thing this person is doing going to be on their tombstone? And uh, usually the answer is no. And the reason I like this concept of life's work so much, which I would define as a lifelong quest to build something for others that expresses who you are. All three parts really important. Say that one more time. 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, Yeah. I I don't um I'm just wired this way. You are too. I I just need to be doing something. I can't sit around. I'm And so I'm I'm drawn to people that are that want to make stuff. And so I have tons of examples of people who have been uh have tried lots of things and made lots of things and moved on from things and had chapters in their life and then a new chapter with doing something totally different. There's there's one um investor that comes to mind whose name is John Feffr. And John has been wildly successful in like the it's almost like he picks whatever he's doing and as he gets to the tail end of it, he tries to find like the thing in the world that is the most different from what he's doing. He says with glee that require him completely abandon his current network because they're irrelevant for it. Like one time he went from being one of the key guys at KKR and then went to be like one of the most important guys in cryptocurrency and then went from that to building like a grocery store chain in the UK. And each time he's like I literally had to start from scratch and I love it. Like I had to build a completely new network of people. And so I know lots of people like John who um have successfully hopped around. You know, I know your focus is more on people that do a thing for a really really long time. Uh, but I don't I don't spend a lot of time with people that were uh prolific creators of things that just stopped. I here's an example. Um I love there's this really fun game you could do it with your friends. You sit down and on piece of paper you write down 10 roles that you play in the world. Podcaster, father, whatever, friend. And and then you pair them up so it's just one, you know, one one thing on each sheet of paper. And then you have to in reverse order, 10 down to one, slowly throw the rolls away until you're left with one. Okay, so one one roll left. It's a really interesting game to 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. Um, you could do this with attributes for yourself, too. Curious, hardworking, whatever. And then and then jettison those one by one. Fun game. I played this with my uh my wife and my kids and my in-laws one time. And I'll never forget it. My my father-in-law had a very very successful career as an entrepreneur. and executive in the kind of healthcare and insurance world and uh we were we were doing this game and his last one was grandfather. So that was like the role that he kept as his final most important one and he is an unbelievable grand like like the Michael Jordan of grandfathers like he is he is unbelievably good at being a grandfather. like makes me emotional thinking about it and so thankful for it and the the difference it makes in my kid's life and his other grandkids life is extraordinary and so Dan is his name Dan is no longer a major healthcare executive he's still an entrepreneur he can't he's not given it up completely but he definitely devotes himself more to something like that which in some sense is much smaller and in another sense is the biggest possible thing you could do and so even the people that sort of like stop the commercial side that I love tend to find a thing to pour themselves into. And in this case, it's the same thing we've been talking about this whole time. It's an act of service to show up at everything to be the most reliable, to be the most fun, just over and over and over again in the in this case, in the role of grandfather. Um, so I think that's exciting for my own life that maybe when I'm 70 I I won't do any of this stuff and I'll do something else that's totally different, but my attitude towards it hopefully will be the same. And that will be because I've gotten the privilege of watching people like him do that sort of role at that stage of their life. So, back to your original question, the people I love and admire most do pour themselves into what they're doing, regardless of what that role is, even as that role shifts around as life goes on. It's like, you know, do you want to go to dinner with this person or do you want to meet this person? And like shorthand between me and you, we're always like, no, they're casual. Like, they're just not. It's the exact opposite. This is a beautiful story. Like I I went from like I pity these people that don't work anymore to like that person's better than I am. That guy's a better person than I am. Bill Campbell. It is so unusual for us to even contemplate that like some of the decisions you're making right now are going to ripple through the generations. They're going to affect things way after that you're you're gone. Somebody, we talked about this uh I think yesterday, somebody took a bunch of like interviews I've done and stuff I've said on the podcast and like literally made like a hip-hop album and there's like eight track hip-hop album. I think it's called like David Center of Founders or something like that. And I we keep talking about it, but but I sent it sent it to Hanky. Uh cuz the first one was like this idea of like general generational inflection point. Generational inflection point, which is like the founder of the family. And you know, Hink is rather religious in a way that maybe I'm not. And you know, he's like he he's like, "Did you script this out?" I was like, "No, I didn't." Like, "Did you know about this?" Like, "No, like somebody just sent it to me." Like, I didn't. You think I'm making music about myself? Like, come on. You Somehow realized, oh, Fidel Castro, this is probably bad. I have to go to a country that like I don't know anybody. Yeah, I don't speak the language. And like that's just one choice, you know, three decades later or whatever, I'm going to be born and now I'm born in a, you know, a capitalistic greatest country in my opinion, greatest country in the world as opposed to that like that one decision by somebody I don't remember like ripples through the entire generations. The story was so overwhelming I honestly don't remember. It was probably husband or father, one of those two. Um, to me, those are the most interesting roles in life. Um, you know, you and I have tal, you know how I feel about those two things. And so, it's probably one of those two where I probably cheated and said, can I have both? Um, and I hope it's, you know, I hope it's that till it's grandfather, I guess. Uh but but the the the available we said I said something like this earlier but the depths available in those relationships are crazy to me. I can't believe that every couple years you I find a new level of those things. I just can't believe every time it happens I'm like I can't believe it's happening again. And in terms of like a place that can yield rewards um th those are the most interesting to me. But uh more generally like the maybe this is the theme of our conversation today. the the the set of small set of relationships of with people for whom I would do anything and that's how I'm wired like there's a certain category of person you're one of them that I whatever you need you don't need to explain it like I'll do it and getting to that point with people I don't think life's too short and and you know there's only so much energy in a day and so you can't do this for a thousand people but you can do it for 10 or 15 you you know, follow Dunar's number or something. You could probably do it for 15 and that is my prized possession. That list of people for whom I would do anything is my prized possession. And I think that that can probably be true for just about anybody. And so I try hope to act in a certain way to deserve that group of people. And even if they even if they don't feel the same way about me, that's okay. If I'm in their list of 50 and I'm 15, it's fine. Um, yeah. I think I think that that role game is quite fun because it it I think it pulls out of you like where you have the most energy. And so I really appreciate you saying yes to me and coming kicking and screaming on. I want to end by turning it around on you. What is the kindest thing someone's ever done for you? That was awesome. Now everybody else gets to see what I get to see in private. And this is why you should do more podcasts. Thanks, Patrick. I hope you enjoyed this episode. Please remember to subscribe wherever you're listening and leave a review. And make sure you listen to my other podcast founders. For almost a decade, I've obsessively read over 400 biographies of history's greatest entrepreneurs, searching for ideas that you can use in your work. Most of the guests you hear on this show first found me through Founders.