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

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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 by far the number one blessing is that she, yeah, we created this, we have created this life together in a way that the thousand things, the 10,000 things that she's done that add up to that 20 years is Which was awful. But I think about him all the time because without him, none of this would have happened and this life wouldn't exist. And so I love this story because, and I love this question, because Whole lives are downstream of simple, quick acts of kindness. And without Tim, my life doesn't look anything like what it looks like today. All the things I care the most about don't exist, probably. And so I remind myself of that every day, which is why I love Assim's question.”
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 we go to a place called Boat Club, which let me in with this fake ID and was shut down for letting people in with this sort of fake ID like three weeks later permanently. May it rest in peace. And I walked into boat club, and the story of meeting Lauren, my wife was that was my first night in Notre Dame, the first bar I walked into, and she was the first girl that I talked to. And that is a crazy stroke of divine luck or something. But it was lucky because I was 19 when I met her. She was 20. We've been together and married and have kids ever since. The true answer to kindness is her because for 20 years now, we just crossed the point of our lives where I've been with her more than I haven't in my life, which is so crazy. I'm not young anymore. I'm 40, but not old. And to have been with her for more than half my life and to have grown up as an adult, whatever they say your prefungal cortex like matures when you're 25 or something. So like six years with her where I didn't even have a fully developed brain.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“He went so out of his way for like the first six months to organ transplant me into his social circle. And like maybe Tim owed me a beer or two, you know, a couple nights out and a beer was his obligation as a family member. But instead, he would like call ahead to his friends saying, like, I'm sick. I can't go out. But Patrick's coming out, can you just like show him a good time? Just like over and over and over again. Like literally, he just injected me into this community. Tim is the reason that I met my wife, which I'm going to come back to in a second, met my best man, met the only other groomsman in my wedding that wasn't a family member. So, you know, through this active over the top kindness of just, there's nothing in it for him. He was just doing the right thing. It sort of set me up for the rest of my life, which brings me to the second thing. So my first night at Notre Dame, Kim shows up with this fake ID that says I'm 5'4 with blonde hair and blue eyes.”
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 call them and I said, where are some schools that have a compatible curriculum with yours? Because I would really love to work hard and then transfer. So they gave me a list. I went to one of those schools. I got very good grades. I transferred to Notre Dame. So now I'm a sophomore at Notre Dame. And I didn't know anybody. I met. It's not like freshman year where you have all this amazing orientation. You transfer to they're like, here's your room number, like, see you later. So I met like a couple other transfer students and that was it. And back to being shy, like I wasn't at the time good at like navigating a new social situation. I just wasn't good at it. So Tim, who I had met like maybe, I didn't know Tim well. You know, Tim was from the Midwest. I didn't know him that well growing up. took it upon himself to come meet me, find me. I remember distinctly he brought me a fake ID.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“One of my third cousins was a guy named Tim O'Shaughnessy. And when I was a bad student in high school, I was like a very good student as a young kid. I went to this giant high school in Connecticut, like 4,000 students. And I just partied way too hard and didn't get good grades and didn't take it seriously. And so there was a day very distinctly. I was at a friend's house having stayed up too late the night before. And my dad called me and said, hey, you know, you should probably come home. There's a whole bunch of very small envelopes here from college. So I actually got, I got rejected from every college I applied to the first time I applied to colleges. And I got all the rejection letters on the same day. It was a bad day. So then I reapplied to some other schools. I had wanted to go to the University of Notre Dame.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“One is the related. So I'll tell them in order. The first was I had a cousin. I come from an Irish Catholic family where when you go to the family reunion, you get a sheet that looks like one of those maps from the 90s where you just have to keep unfolding it because it's just so goddamn many people. And so I have cousins who are technically my third or fourth cousins that feel in my family more like a first cousin.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“To deserve that group of people. And even if they don't feel the same way about me, that's okay. If I'm in their list of 50 and I'm 15, it's fine. Yeah, I think that role game is quite fun because I think it pulls out of you like where you have the most energy.”
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 more generally, like the, maybe this is the theme of our conversation today, the set of small set of relationships with people for whom I would do anything. And that's how I'm wired. Like there's a certain category of person, you're one of them whatever you need. You need to explain it. Like, I'll do it. And getting to that point with people, I don't think life's too short and 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. 15, you know, follow Dunbar's number or something. You can probably do it for 15. And that is my prized possession. That list of people for whom I would do anything is my prize 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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“The story was so overwhelming. I honestly don't remember. It was probably husband or father, one of those two. To me, those are the most interesting roles in life. You know, you and I have talked, you know how I feel about those two things. And so it's probably one of those two where I probably cheated and said, can I have both? And I hope it's that till it's grandfather, I guess. But 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 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, those are the most interesting to 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
“The people that we all worship in the business world. I'm amazed by them too. But there are flavors of success. And to me, that sort of devotion, even if it's to one person, to your wife, to your kids, whatever, is every bit as successful. And if not more so. Because that shit will ripple through history. My son and my daughter will now behave differently because of the experience that Dan and my mother-in-law and my dad and my mom gave to my kids. So what's better than 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
“I never met Bill Campbell. I wish I had. It's this beautiful archetype of older guy from just working with a couple executives that he worked with Google and some of the most famous companies, but was apparently transformative in the lives of these people. But it was like five people or three people or whatever small set of people. And that's it. And he wasn't doing it for money or fame or power, any of this stuff. He was just doing it to help these couple people. I think that's a really cool exercise to be like, what if the only thing I was allowed to do in my life? Nothing else was allowed, was help three people. Who would they be and what would I do for them? Dan helping his four grandkids or something like that. That makes me excited for later stages of life when I think the ability to do something like that goes up. And that is every bit as successful in my mind and in my book as Elon Musk or Jeff Bezos or”
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, honestly. There's something very beautiful about the scope of the ambition shrinking so narrow. We talk a lot about the trillion dollar coach. What's his first name? Bill Campbell. Bill Campbell.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Be the most fun just over and over and over again. In this case, in the role of grandfather. So I think that's exciting for my own life that maybe when I'm 70, I 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. 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.”
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 that was like the role that he kept as his final most important one. And he is an unbelievable grandparent. Like the Michael Jordan of grandfathers, like he is unbelievably good at being a grandfather. It makes me emotional thinking about it and so thankful for it. And the difference it makes in my kids' life and his other grandkids' life is extraordinary. And so, Dan, this name, Dan is no longer a major healthcare executive. He's still an entrepreneur. He can't. He's not given enough completely, but he definitely devotes himself more to something like that, which in some sense is much smaller. And in other senses the biggest possible thing you could do. And so even the people that sort of like stop the commercial side that I love tend to find a thing to pour themselves into. And in this case, it's the same thing we've been talking about this whole time. It's an active service to show up at everything to be the most reliable.”
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 you tear them up so it's just one thing on each sheet of paper. And then you have to, in reverse order, 10 down to 1, slowly throw the rolls away until you're left with one. Okay, so one roll left. It's a really interesting game. It's interesting for yourself, but also super interesting to see what your friends pick. First of all, what's on the list of 10? You could do this with attributes for yourself too. Curious, hardworking, whatever. And then jettison those one by one. Fun game. I played this with my wife and my kids and my in-laws one time. And I'll never forget it. My father-in-law had a very, very successful career as an entrepreneur and executive in the kind of healthcare and insurance world. And we were doing this game. And his last one was grandfather.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Here's an example. There's this really fun game if you could do it with your friends. You sit down and on a piece of paper, you write down 10 roles that you play in the world, podcaster, father, whatever, friend.”
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. Just wired this way. You are too. I just need to be doing something. I can't sit around. And so I'm drawn to people that are, that want to make stuff. And so I have tons of examples of people who have been, have tried lots of things and made lots of things and moved on from things and had chapters in their life and then a new chapter with doing something totally different. There's one investor that comes to mind whose name is John Peffer. And John has been wildly successful in like the, it's almost like he picks whatever he's doing and as it gets to the tail end of it, he tries to find like the thing in the world that is the most different from what he's doing. He says with glee that require him completely abandon his current network because they're irrelevant for it. 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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“To make great investments. And it's really rare. But the leadership qualities of life, like the reward for great work is more work. The reason I started talking about life's work and investing is these people realize, come to realize you will not be rewarded with great work if you do not become a good leader. And a common pitfall that I certainly have fallen in before is when there's someone really talented, they can do a lot themselves. They can get a lot done themselves. And I refer to this as like heroics. And that's always necessary. A founder always has the sort of, is the flamekeeper of the spirit of the company. And I think founder-led companies are so, of course, so much more interesting preaching to the choir here than professionally managed companies for the most part. But I do think that becoming a great leader becomes the most important way to secure”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“A lifelong quest to build something for others that expresses who you are. And we have trained ourselves to see this in people. By the way, the best way to figure this out, my favorite question for founders, is literally just give me two hours. Tell me your whole life story up until the point you founded your company. We'll talk about your company later. Like just tell me what got you to here, back to Best Story Wins, originality, hardship, transformation. In the business context, it's I want someone that's lived a very unique path. I find success in startups is the result of path dependency very often. Some unique set of lessons and experience led to you being the right person to do this thing. And then hardship, of course, you know, the harder the business is to build, the harder it will be to copy. I think that's really important. Transformation is about the customer. If you build something crazy hard, the customer's life will get way better service. So I think this powerful concept of life support can be applied to ourselves.”
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 describe his life, but one of them is not that he was the president of the United States, author of the Declaration of Independence, founder of the University of Virginia, not president. I think that's so interesting. And so I think a lot about like, is this thing, this person is doing going to be on their tombstone? And usually the answer is no. The reason I like this concept of life's work so much, which I would define as a lifelong quest to build something for others that expresses who you are. All three parts are really important.”
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 joy of that sort of thing and that sort of leader, my favorite, my view of all these great maxims, my favorite maxim, pretty much the only one we use in my business with my team, is the reward for great work is more work. And I find that saying that maxim to the right person, like the kind of person I want to spend time with, their eyes go wide and they understand it immediately that the reward for great work is not money, power, fame. It is the privilege to get to do more of this thing that I love doing. The problem with coming up with like good terms for this stuff, we use this term life's work, is that immediately everyone else just starts saying it and it ceases to have any meaning because like now every goddamn meeting I'm in, like I'm doing my life's work. And my experience is that almost nobody is doing their life's work. Even a lot of great founders, I would say it's not their life's work. I love the fact that Thomas Jefferson on his tombstone has three 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
“One of the big ones is that they are hyper communicative with those people and they're consistent and Think I was quite bad on that dimension for a long time. Not because I was trying to be bad, just because I was so excitable. I am so excitable. Like when I find something new and interesting, like I just cannot get enough. But very often that means I'm billy goating up ahead of the pack. And forgetting, like, oh, wait, I need to like, there's all these people that I want to do this with. I don't want to just do this alone. So that's been a big lesson for me that has taken a while to learn. But yet another thing to credit Sam with.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Robbie's was my favorite. And what I've learned about what is shared in common amongst people that others want to follow.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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 were backing that are usually pretty early in their company building journey. So you're mostly or largely backing the person and the team versus the mature business story. And pretty important that that person's a good leader. I think one of the things I underestimated about great leaders that Ravi Gupta, who's another person that I would list and people that have really impacted me, at one point I called everyone I knew, I was like, define good leader. I'm going to do a survey. And Ravi gave my favorite answer. He was like, it's not hard. Like a great leader is someone that other people want to follow. And everyone else had given much more ornate definitions.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“An idea. And then I would change my, and it 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 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 that are like signed on to do a thing. And then a week later, you're like, what are you talking about? What thing? We're doing this thing. So I've worked pretty hard to narrow, simplify my life with rhythm and harmony, focus on fewer things, like get less distracted by what I would call like the flavor of the month club, which is something that can definitely snare me for sure.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Tighter situation. And I have to reduce the amount. And he started to tease me because he was like, wait, so when I first called you a month ago, you had never even thought about having a fund. You have 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 I think that's a good example of like, yeah, some opportunity came out of left field. There was this investment opportunity in one company that led to a fund very quickly in the summer of 2020. And so, yes, I like to move really, really fast when I'm interested in something, but my interest does shift around. And I don't think this is a good thing, by the way. I don't want to whiplash people. And I realized thanks to Sam that I was whiplashing people, I would be so excited and willing and able to galvanize people around.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“The example he gave was that Sam at the time was raising his first fund. And I was going to be an investor in the fund. And so he called me and said, you know, putting this fund together, it's small, limited group of people. I'd love to have you if you want to do it. Hell yeah, I wanted to do it, of course. and told him the amount or whatever. And then he called me back like a month later and was like, okay, like I have the docs already and we're ready to go. And you're still in for this much. And I said something like, well, I can't. Yes, I'm still in, but I can't do that much because actually like I have also launched a fund. And he was like, what? And I said, yeah, you know, I need to make a GP commit to my own fund. And so I'm, you know, this is before I sold my business. It's a little bit, you know.”
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, yeah, yeah. He was very disturbed by this, and he tried to fix it. Yeah, I know. Yeah. He tried to, he put me through a guided, like, he tried to hypnotize me into visualizing something. It didn't work. So anyway. The other side of that sword, it freaked me out that I couldn't see anything with my eyes closed. But the other side of that sword is like, when I'm focused on something like here, right now, I am not thinking about other stuff. It's just all of this. I wish it wasn't the eye of Sauron. That sounds so bad. It said in a loving way. I understand. So Sam's point was you're red on the color wheel.”
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 know, it's interesting I learned something about myself recently, which I at first was terrified about, and now I've come to view as everything is everything is double-edged, which is I have, if you close your eyes and try to visualize something, a red cardinal or something, there's a degree of how visually sharp that thing looks in your mind's eye when you close your eyes. For me, it's just black. I can't visualize anything. I can't see anything. I'm like, I discovered this like a year ago. I'm like, wait a minute. You can see things with your eyes closed. What are you remembering? We were bragging.”
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 am intense, and I've always been this way. I am voracious and intense and aggressive. And I would say I have a skill at making things happen when I'm interested in them happening. And maybe that's one side of the sword. The other side of being red on the color wheel is this like locked in intensity. The other side of it is that the moment that attention is focused elsewhere I can tend to whiplash around a lot and change my opinion really fast.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Character and judgment and fidelity and just so many things about him. But like what a role to play in somebody's life. He's the one I invoke in my head, one of three or four people that I invoke in my head of like, what would this person think about this thing I'm about to decide on? But back to the story. So he said, yeah, it was something like what's my biggest weakness. And he described me as being red on the color wheel, which he explained meant that when I'm in.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“What is it? Well, first, just a thought on Sam, which is Hard to imagine a higher compliment I could pay someone than the role that Sam plays in my life. The way I would phrase it maybe is I have more conversations with Sam when he's not there than when he is. What I mean by that is I'm often finding myself wondering in a situation like what would Sam think about what I'm going to do here. I so value his.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Obligatory disclaimer that I've been so unbelievably lucky. I had the privilege to sit and read a gazillion books and not be spending all of that time just getting ahead like you had to because, again, I was very lucky the situation I was born into in life with the parents I had and the things that were easy for me. I didn't have to pay for college, all this stuff made it possible for me to do these things. And I think that's important to acknowledge but nonetheless, like you found your way there. You found the passion. You found the high rep passion. And now look now look. That's like my constant urging to people. Like it's there. I promise. There's something. Just go find it.”
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 had told me when I sent that first email to list my goals, none of those things that I just listed would have been on my sheet. I wouldn't have even known to think about them. My own experience has cemented my belief in this growth without goals. Like I wanted to grow. I love the idea in weightlifting, Jeremy Given and I talk about it all the time, a progressive overload of like always like a little bit harder, a little bit more, like go to failure, go to failure, go to failure. But you don't, the beautiful thing about life is you don't know where that's going to take you. God, I never in a million years could have predicted any of this crap. What's even more exciting is it doesn't stop some set of stuff's going to happen over the next 10 years, which if I tried to make a goal this today, I would be unable to predict. It's going to be so much fun. But it all started with, I had a thing I loved naturally. I just liked to read books. And I think that's profoundly cool. Now,”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Is Daisy chained together because I loved reading books in my 20s and I did something about it and I started telling other people which ones I liked. That's how it started. That's it. And all of that was unpredictable. Back to why I don't like goals.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Crazy high rep count of, probably that's a good clue to where you could go build one of these compounding curves for yourself. And for me, it was my first love was reading. That love of reading became the email list. You know, here's my four favorite books from the month. The email list gave me my first set of people to listen to the podcast. The podcast introduced me to all these people, helped me build my business and sell it successfully. And on and on and on. That led to positive sum and me building my business successfully in software got me to all of these people building early stage companies, writing these small checks, writing these small checks got me to this Series A investment that caused me to create this new investment firm. Creating this new investment firm caused me to go invest in all these companies in a bigger way and be more impactful on them and their trajectories than I could have been on my own. The whole thing.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Still works, and it's maybe that's my governing principle, probably like you said before. And yeah, it's an incredibly powerful loop to go on. But the 10 years of reading prepared me to be a good producer of profiles because I've seen great. I've seen good. I've seen average. I've seen bad. My reps are very, very, very high. And that's another thing I always tell people, especially young people, is like, what is the thing where you naturally have a lot of reps because you just like it and find some, build off that because there's this learning by doing concept, like you get better at something just through being prolific in the thing. And most people have a thing for which they are naturally prolific. If that's following your sports team or whatever it might be, like what's the thing you just can't help but 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
“The way I spent my 20s basically just reading. And I read more than you can imagine. I mean, you're probably the one person that can imagine it because you did something similar. But I wasn't just doing, I mean, literally everything I could get my hands on thousands and books and profiles and everything. And I started the podcast in part because I started to feel this all.”
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, yeah, people show you. And I think that also, if you invert that to use another mungerism, it serves as great advice too, which is if you're trying to get ahead, put stuff out in the world that people can find Hinky would call these breadcrumbs, put breadcrumbs out into the world so that people see it and are amazed by it. Like if you create a single thing, not you don't do 10 things, just one thing that people are amazed by. Pour a year of your life into making one amazing thing that people are amazed by and amazing things will happen, I promise you. The internet is amazing at sharing something that is great. You say there's always room for great? Yeah. One of your maxims. That's true. Great takes time. Great's hard.”
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 people started, you know, this, they're this, they're this. And this one investor's face started contorting. And you could just see that he was frustrated by all these answers. And it got to him. And he was like, morons, who cares? Did they make a good invention? If the invention is good, the inventor is probably good. And so I think you and I have taken that approach to I certainly have to finding people. Just look at what they did. If they're the Jeremy wrote the best profile that I read. It turns out he's a great profile writer. He's written 10 more and we'll write 100 more. I was then on the hunt after I had this I and we had this idea to go now, okay, now let's go find the let's go find the best people to do this thing”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Before. So I was then on the hunt. And this is another idea that you and I talk about often, which is if you want to hire someone for a thing, just go consume as much of the thing made by a million people as possible. Whoever made the best one, go for them. There was this funny conversation during COVID, an investor friend of mine, one of the great investors ever who's now retired was part of the Zoom conversation. And it was the topic of the conversation was attributes of great founders. And at some point, someone goes, well, maybe it'd be easier to think about them not as founders, but as inventors. And everyone thought, oh, this cool idea. Okay, let's talk about them as inventors, not as founders. And then someone said, well, what are the attributes of a gradient?”
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 had all these incredible people on the cover, and I thought this is strange. Like, why are these people doing this magazine that no one's ever heard of? Big names. And it dawned on me. I was like, oh, it's the cover. Like people can't say no to a cover. And so I tested that theory out and it was true. And I think what that means is it's like the ultimate form of spotlight and attention that you can give to somebody. And so that's what got me actually literally spinning on like, oh, maybe we should, I would love to have a cover that I could dole out. Did that idea come before or?”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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 yeah, I'm interested in stuff that's very hard to make that's singular, that can't be easily copied. I mean, the literal answer to your question is kind of funny, was somebody, I'm actually seeing him Monday, gave me the idea to potentially buy this existing magazine. And we didn't buy it because I like to create our own things primarily. But it was notable to me that this magazine, which had been around for a long time, had all these incredible, I'd never heard of the magazine.”
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 maybe we'll write something in 10 years. So things that are really hard to make are really interesting to me. And I think people stopped doing profiles because they're really hard to make. They take time. The business model kind of sucks. Like the pay is terrible. You know, profile writers are not paid well. The world went a different direction. It's much cheaper and faster to make a stupid fucking TikTok than write a 50 page profile about someone that's careful and intricate and well written. 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 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.”
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 we write 10 years from now that we start working on today. We have this idea, which we've started to do where we just ask people, can I just have lunch with you once a year? I'm not going to do anything with it. Just like, I'm just going to, I just want to start collecting the line.”
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 the other part that's exciting is because I like things that are really hard. Okay, so originally hardship, we didn't talk as much about hardship. I think you've been talking a lot about doing something that's different just because it's different. I would add on, which I think is interesting and correct, but I would add on to that, like it should be different and really hard, like really hard to do. If I just, I'm sampling all the profiles we've written in my head. Some of them are ridiculously hard to write not only because of all the hours and work that has to go into it and the talent as a writer that has to go into it, but sometimes it's sensitive parts of the person's life that's never been written about and they've never talked about and maybe they don't want to talk about it or they don't want you to talk about and it's the coaxing it out of them and that takes time and trust. And so the thing I can't wait for is the profile.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source
“Not needed at all because that means we're creating more of them. Obviously, I'm limited by my own bandwidth and time. I'll always do interviews. I hope it gets bigger and bigger. And I don't want to fade into the sunset. But I hope this is much bigger because that means I get to hire more incredible talented people and hopefully put them on a career trajectory that's the best it could possibly be. And that's incredibly gratifying. I get to read more of these things. I get to do this thing that we love to do for more people and point the light that we're trying to cultivate on more and more talented people. That's unbelievably exciting. I hope it's not just writing. I hope it's documentary. I hope it's, who knows where it goes. I hope we start convening people in small situations where meet this person, meet this. That to me is the most fun thing in the world. And so a world.”
2026-01-20 · Invest Like the Best · Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] · IDENTIFIED FROM THE TRANSCRIPT · source