YouSaid · the spoken record

Patrick O'Shaughnessy

lines on the record: 107
first: 2026-01-20
most recent: 2026-01-20
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“So, I can enjoy them more. And I'll get to enjoy it just like everybody else. Like, I can't tell you how fun it is to get the first draft of one of these things in Slack. Like the things that make me the most giddy in my work are some new draft that they've created for Colossus and some new research report on an investment created by my incredible team on that side, who in many ways are just doing its turtles all the way down. It's the same deep investigation, publishing, writing, clear thinking. When I get one of those two things in the morning, oftentimes there's days where I have several of them, those are the best days. And so selfishly, I would just love a world where”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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 we want to tell the hard parts 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 idea. I mean, literally, everybody said it was a stupid idea. When I started the podcast, everyone said it was a stupid idea. When I started Canvas, everyone said it. I think like if people say something's a good idea, I always get a little nervous because if it sounds like a good idea, it just feels you're in a more competitive space. It's going to be harder. I think the key is stuff that sounds dumb but isn't. And I think that's what I would, starting a magazine in 2025, I think falls in that category of sounds dumb. Magazines are dead or dying. But the thing.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Holocaust. And I don't think anyone else would take that risk in a profile of Josh and his family and his team. But it was so important to understanding the soil out of which his family and eventually he emerged. And Jeremy also, the writer, was the product of Holocaust survivors himself and knew a tremendous amount about Josh's family history because it was also his family's history. And I thought that was the coolest, most beautiful thing. I never would have, you know, so this 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. Same thing we've been talking about over and over again. So now team members become.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“On Palmer Lucky from Andrew, and I reached out to the author. His name is Jeremy Stern, who's now the editor-in-chief at Colossus. And the rest of that story is sort of history. He joined. We've got other people that have joined or are joining to write these profiles. And it just felt like, wow, this is another way to do the thing we love to do, which is to find the person become obsessed, learn everything about them, take great time and pain to write a definitive thing about them, and then share it with millions of people. And, you know, the fact, the one that we wrote about Josh Kushner and Thrive was one of these like bizarre break the internet moments when it just like completely took over the internet for a while. And I remember reading it the first time. And I was like 45 minutes into reading it. And I was still reading about the”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Because I'm not writing the profiles, our amazing team is writing them, it would actually be a double whammy that not only, when we started doing this, I went and read David Remnik, who's the head of the longtime editor for The New Yorker and New Yorker profiles were always my favorite growing up, these incredibly detailed, amazing, well-written profiles. He wrote in the introduction to this, his compilation of his favorite New Yorker profiles. There's this line that says the best profiles over the last hundred years are defined by somebody doing a thing they're obsessed with and a writer that is as obsessed with the person as the person is with a thing. And I remember reading that paragraph and just thinking, wow, I want to read, that's what I want to read. And, you know, so I went and I read a million profiles and the very best one I read was in a publication called Tablet.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm in the abstract very interested in how can I create and control valuable scarce units of attention and then build those things out to the people that we believe in at a very high level. The reason we now have a magazine, which on its face I think was, as everyone would have agreed, was a stupid idea or told me it was a stupid idea when we started it. Why are we doing these profiles that take months or quarters or years to write and require lots of investment why do that? Well, the reason is I think it's just in a beautiful way to shine the light beyond like podcasting on people that we admire. And to teach someone, teach the world about a compelling founder or a compelling investor or artist or whatever. And the thing that I didn't realize was that.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Two people came to mind right away. The first is Herb Allen from Allen Company, who I don't know well. These lessons came from one incredibly interesting conversation about my sense of him, again, don't know him well, is that he is uncompromising in his values. He does He's maybe like the apex predator of the thing I want to do, which is picking and supporting people. I think that's what he's done for a really long time with unbelievable success. And that is so incredibly uncompromising about how he does that and willing, I won't tell the examples, but like I think willing famously to like throw away huge commercial opportunities just because the person wasn't who he wanted to support. So sometimes it's literally a conversation with a person that just Smacks you in the face.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Chathan the demo, you know, the demo. I'd show him the demos. And it was amazing. He gave me feedback. They weren't an investor in my business or anything. He was just doing it out of just the goodness of his heart, I guess. And same thing with the others. And there's many, many more than three people that contributed to that project that influenced me and taught me things. But yeah, mostly just offline asking questions, but I did interview Chathan several times and Daniel several times.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Too hard about what they tell me and just doing it and having it work. And so there's a tiny example, three people. Did you have them all three on your phone?”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Take the simplest example possible. In the early days of the show, this is a very practical real world example. If you take the ideas that I got from Daniel, who you mentioned before at Spotify about how to build software, from Brett Victor, who I mentioned before about this principle for great software and what it looks like, and from a guy named Chathan Pudagunta at Benchmark, one of the partners at a very story 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 those three or three of the greatest in the world what they do, how do I do this to somebody that could help me and then not think.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, the clean fueled, dirty fuel debate is really interesting. And look, a lot of many, most, nearly all of the books that you've read were people that were fueled by dirty fuel. Dirty fuel works really well, but it consumes. The person in a way that I would far rather die, you know, nobody knowing who I am with no worldly success, but having people that could count on me, rely on me. I was faithful to, that I was loyal to. That's what I want at the end. So if you can work backwards from that, that's another cool way to think about it. Like 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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, you tell Bruce's story, but I think you're talking about yourself to a large degree. I And maybe my arrival at the aspiration, I'm by no means perfect, to be more service-oriented, my grandmother, who just passed away, she was 99, banged on me. Every time she'd see me, this would be the topic of conversation. She's like, yeah, yeah, yeah, congratulations on all the success. Like, who gives a shit? Like, what are you doing for other people? That's what I want to know. I'm convinced that's the way out that I think I like you and like so many listening have their set of demons that they've struggled with and the path out is others. Simple as that. And it sounds like Bruce, I don't know, Bruce. I'm not a huge Springsteen fan. I need to read the book, obviously. But that seems like a tale as old as time.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, because of course on your deathbed, that's what you're going to be thinking about, not your 5,000 podcasts. You're not going to lie there and think.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“And then some, I was crazy about it. I kept daily logs of all this stuff. Like there's nothing I didn't try. There's no Willy Fufu thing that I didn't explore. I tried everything to solve some of these problems. And I couldn't solve them. And at one point, I felt resigned. It's just like, I guess I'm just one of those people that's going to be sick in life. Like that's just how it's going to be for me. It cannot be coincidence that when I finally started doing the thing that I think I was meant to do with my life and spend all my time with the people and focused on the relationships that all of a sudden my health got better. So now, of course, I still invest a lot in my health. I'm not arguing with the three key things. But I found that an interesting experience in life. The body keeps the score.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“My experience actually, I would disagree with the order. I had tremendously bad health problems for a long time. And I don't anymore, thankfully. But I'm convinced I'm certain that the reason is that I finally got my work and my relationships correct and that when you're doing something you love and have great core relationships, all of a sudden magically your health gets way better. During that time when I had lots of health problems, I ate unbelievably well. I worked out every day. I did all I did everything you're supposed to do.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I don't. I think it is. I wish I could do what I do. And the thing in men in black where they flash you in the face. I wish at the end of each of my episodes, flash people in the face. And they forgot who I was and they didn't recognize me.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, the trap is. Before you do the work to figure out the thing that makes you feel alive. This great line in the Upanishads that it's always referred to abiding joy, like joy that doesn't run out, you don't use it up like you use up so many resources. As you use it, you get more of it. That's abiding joy. The target for most people becomes the traditional money power fame because those are worldly proxies for success that we all recognize and are for sure to some degree true. It's hard to get a lot of those three things without being successful in some way. I think those things are huge traps because once you start to get one, it's the thing you start chasing and it's different than chasing the feeling of being alive, that abiding joy of feeling alive that we talked about earlier, which you'll never run out of. That will always guide you well, always. And money powerful.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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 had that experience and gone back. Not one. And it's because I think it's the thing that we're all after. And that's what you're doing too with this show.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“And I remember 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 being of service to other people in some way, I think that's the thing that actually 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 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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“You mentioned organizing principle, which. I think that's correct. Just to push, because this can now be something we talk about for the next couple of years, which is probably how long it'll take to articulate, that's different than what is your principle for invention. So back to the idea of inventing on principle. The principle should be something that when you see it violated, it is your obligation to go correct it and that that correction is an act of service for other people, not for yourself. It's not about you. That's what makes the idea so powerful. I agree that that's your organizing principle. That's like the thing behind why you're doing what you're doing. It will be fun to try to pin down what the principle is for invention because that's what you're doing. You're making new things, which is the most fun and rewarding experience of”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“And that's fine. And then once you learn that, I think that's when it gets really fun. 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 some new way. But I think that's what founders does so well is it shows it's what back to the very beginning of our relationship and why I sent that tweet out and why we talked to each other for an hour the first time we talked It's because it was so unique and so different and inspiring. So I think that's a powerful thing to do for people.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Church for entrepreneurs in that church. I think the animating interesting question is you read these stories, all of which back to my idea of originality, hardship transformation, you know, best story wins, that originality is you're inspiring people to wonder, what's my thing? Everyone's got something. I guarantee it. It's my favorite thing to search for in conversation, especially if someone's not yet doing it, which is kind of the same search for unrealized potential or something. Everyone has a thing that for whatever set of reasons their life experiences, how they're wired, their naturally endowed gifts.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“I also think you're providing people with a sort of set of ingredients, maybe through these episodes and conversations, but that it's important that people then go make their own recipe. Like you shouldn't just want to live like person X, Y, Z. A lot of people you cover have the same pitfalls in their lives. And one might be tempted to think those pitfalls are just inevitable byproducts of success. But I hate that kind of thinking. I think screw base rates. I don't care what the base. I never care what the base rate is. The most interesting stuff is outliers by definition. So I don't care what happened to everybody else. I don't care if there's common pitfalls. I think it's important that people take their own recipe from the ingredients that you've offered them from all these amazing and interesting lives that you've studied. And you're just doing that for yourself. That's been the search.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“This is one of David's quirks. He tells you how long he talked to someone every time. I just had this four hour lunch with zones.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Have to just keep going the same direction that you were given. You can break off and found something new. I think that's pretty amazing.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Sun are the same. And it takes tremendous character, willpower, talent, lots of stuff to break from that family tradition and go a new direction, which you've done, which I just think is remarkable. 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. You went, as Sam would say, and we've talked about you went searching for mentors because you didn't have them in your life. You found them in books and in founders and you've been telling everybody about it ever since and it worked for you to change your life and now we know based on your work that your work is now changing other people's lives in that same way that you changed your own first but you were the first beneficiary of it and so what is your principle or why I don't know maybe it's that you can you don't”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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 they would say, well, Mr. IA, I cut his hair and he put my kids through college and bought me a house. Or Mr. IA did this or this, this. And we didn't even know where it went. And I have benefited from this tremendous history of business success in and around my family forever. Whereas you came from a very different set of circumstances. Our friend Sam has this idea of there's founders of businesses and there's founders of families. And I think of you as the founder of your family. And I think that's incredibly powerful. And I think it's your greatest accomplishment that things repeat through the generations. You're fond of saying the story of the father and the father.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, I think you've talked about this certainly in private with me, but also in public about you came from opposite circumstances. Like I was born on proverbial third base or sliding into home. I come from a history of extremely successful entrepreneurs. My great-grandfather, who had the best name ever, his name was Ignatius Aloysius O'Shaughnessy. Everyone called him IA. He was, I think, the 13th of 13 kids. He was one of the richest men in the United States. He was an oil wildcatter, first oil hole he ever drilled, I think still pumps oil to this day in the Midwest. And so he was a giant, he was broken up in the antitrust, 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 shit about money. He didn't really spend it.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“So, important difference. Well, it took me a decade to state my organizing principle. I'm not going to be able to name yours in a minute. But you're probably the most single-minded and devoted to what they do person that I know in the sense that most people that have achieved a level of success in their field or in their job that you have begin to branch the world when that happens pulls you into this branching exercise where you end up doing lots of different stuff and you end up monetizing in different ways or going into different lines of business or changing how you do things expanding the single mindedness that you have is quite distinct from the people that I know and why are you doing it i”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Just to clarify, it's not helping as many people as possible. It is trying to see enormous, like not yet realized potential. And my principle is that when I do, it is my obligation. With nothing, maybe I invest up benefiting, but that's not the point it's my obligation to tell people about it and to help foster it into existence.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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 seeking and like all the modern methods for doing that. And I've kind of just lost, not total interest, but I've lost a lot of my interest in that.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“It definitely helped me find it because I wanted to not waste life. When I was a little kid, young, five years old or whatever, I had this just crippling fear of death. I remember my mom and dad would have to sit and hold my hand for me to fall asleep at night. And the reason was I would just sit there spiraling on this crazy idea. Maybe this is why I studied philosophy that someday I would not exist. And that just freaked me out and did for decades. 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? 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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Usually it's simple, which is fear. Fear that by pursuing an original path, I have this idea that the best story always wins. And I actually spent the last couple of months really trying to figure out what do I think best story means. And the best principles for a great story that I could come up with were originality, hardship, and transformation. 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 of the unknown because an original path by definition means it's all going to be on you and that's uncomfortable and hard. And because an original path usually means leaving a very comfortable current existence in a way that's scary.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Everyone can answer this question, by the way. It's a really great way to have a conversation with someone is to kind of ask them where they feel this and then also why they're not doing more of whatever the answer happens to be, which is a funny circumstance of humans that they kind of know what makes them feel most alive and then they don't do it most of their lives.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't know if it was Alan Watts that said this. He had such a way with words that maybe it was him. It might 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. And I think a great, if you play red light, green light with principle as you search for your principle, I think you could do a lot worse than knowing you're on the right path if the thing makes you feel more alive. 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 remember that reading that line 15 years ago as well. And then starting to chase the feeling of being alive, not a goal, but just that feeling.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Worked well because of his principle of instant feedback on choices being made by the user, showing up in this case in a visual that described their portfolio. And so I actually, before I had my own principle, I stole his principal 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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“I actually don't think I could have articulated the principle as I just laid it out until very recently. So I could have told you about the power of Brett Victor's inventing on principle starting 10 years ago or whenever I first saw it, but I would not have been able to articulate the principle to you cleanly. And that's because it's hard. It's hard to pin for a variety of reasons. It's really hard to pin this down. Interestingly, I've never met Brett Victor. If he's listening, I'd love to meet him. I owe him an enormous debt of gratitude for one of my bigger career successes, which was I took his principle, not my own, but his principle of instant feedback 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”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“And emulate because I'm sure you've learned this about kids as well, they don't do what you tell them. They do what you do. They just copy you. And so how you behave is how you parent. And I was thinking about that at age 28 and wrote this thing. And so that's where it came from. So right around then is probably the first time.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, this essay that I wrote, I'm 40 now. I wrote when I was 28 because I wrote it on the train. I used to commute back and forth from New York City to Stanford, Connecticut. And I was about to have my first child, my son Pierce. And my dad, when I was 21, handed me this book of letters that he had been writing to me since I was born. And a lot of them were when I was like a baby, like the, and I've done the same thing for my son. And it's the same pattern. There's tons of letters in the first couple of years. And then it gets more spaced out. And now I do on his birthday every year and things like this. And I'm going to give him a packet of letters as well. When he turns 21. And I remember starting this process of wanting to write him a letter before he was born. And it got me wondering.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Invention. And 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, they tend to do it. And that's why goals are interesting to lots of people is it's a great way to make progress. But I find it unexciting because the second you set some big goal, you kind of know what's going to happen because you go do it and you know the road in front of you and you have blinders on. I don't actually like having blinders on. I like everything that's ever worked for me has come out of the periphery. You know, Sam Hanke text me about you. Like 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 the left field and everything interesting I've ever done came out of left field. And which is why I don't keep long-term.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“It's taken me a long time to articulate that principle. And that's okay. Don't get discouraged if you don't watch Brett Victor's talk and can't name your principal an hour later. Like it takes time. But you know you found your principal when it starts informing literally every decision you make every day with your time. And that's what it does for me. And it becomes universal. on my team, for example. were 16 people, something like that. Now this is how I think about my team. It's like who can I find and see something in and bring them in and then make their career explode, hopefully, in an amazing way. And so it can be investing. It can be just in friendship. It can be on your team. 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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“You should find a principle that you want to. His principle was creators, digital creators, should have instant feedback with their creation. So just like if you paint something with a paintbrush, you get instant feedback. You see the paint immediately. Whereas in computer science, you would have to code over here and compile, and then you'd eventually see your result. There was this gap. And so his principle was collapse that gap. That was his life's mission. I love that way of thinking about finding one's life's mission is find a principle. Don't necessarily have a goal, but find a principle. And my principle is like when I see undiscovered talent, it is my obligation to do this thing, to get to know them, to learn from them, to start introducing them to people, to start, I don't need to get anything out of it. Like what I get out of it is the thing. That's the point.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Said before you're chasing something, right? Yeah. I'm not chasing anything. I think it might be interesting. Conversation today to talk about how we view what we're doing in slightly different ways. But I have no goals. I'm not a goals person. I've written essays about not having goals. The most red thing I ever wrote back when I used to do a lot of writing was about, it was called Growth Without Goals. And so I'm not chasing any particular thing. I don't have a big, hairy, audacious goal or something like this. I don't want to put someone on Mars like Elon Miter. And I'm not to say that that's a bad thing. I think some people are goal-oriented and that's awesome, but that's not me. And I guess I've realized that if I have a goal in the abstract sense, it's just this thing over and over and over again. There's this amazing talk that I recommend everyone watch called Inventing on Principle. Have you seen this? Yeah. It was a talk given by a computer scientist named Brett Victor. And he espouses this idea that”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Period of life that was tough. And it just woke me up that the whole point of this is to help other people. That's it. That's the entire point of this existence. And from that point forward, that's been my worldview. And so I think it's interesting that that's probably the thing that most informed my worldview. And then the answer to this question that I love to ask is predominantly someone bet on me. And like I told you before, the thing I love more than anything is like seeing the potential in somebody before everyone else and then helping the world see what I see. Like if I can do one thing over and over and over again, the rest of my life, it would be audition people to see if there's something that I see that no one else sees and then help foster that and show everyone else what I think I see in a way that can be impactful on that person's life, which is what you described with our experience together.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“I was in a weird spot in life. I kind of hadn't found anything to do yet. I wasn't that good at anything. And I was searching. I was always searching for like, what the hell should I do? What the hell's the point of all this? And I found this passage in the Upanishads, which as a book is probably the most important book to me. And the Upanishads is this collection of stories from many thousands of years ago that were oral passed down orally through generations and then eventually written down. And I remember getting stuck by this on this one passage that literally felt like someone hit me in the face with a hammer. And there's a line in this passage that basically says something like those who feed the hungry protect me. Those who don't are consumed by me. And it just felt like there was like a moment of understanding that happened in my head that up until that point from middle of teenage, I was a nice sweet boy and then I got kind of hardened and went.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source