A Compulsive Search for the Most Interesting People with Patrick O'Shaughnessy

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“I don't know if there's a trick here. What you get on my podcast is just me. It's not a character I'm playing, it's just me, and that's a very sustainable strategy.”

If you work in finance or technology, you’ve heard of Patrick O’Shaughnessy, the prolific host of the podcast Invest Like the Best, (and podcast firm Colossus), head of O’Shaughnessy Asset Management (now part of Franklin Templeton), and venture firm Positive Sum.

‍"The ambition is how do we create multiple a day that are as good as our very best episodes? That's my only real question with Colossus.”

My guiding question for this conversation was to figure out how Patrick was so good at finding and interviewing the world’s most interesting people in technology and investing - and manage two asset management businesses at the same time. What is his secret?

“Having a singular goal that's far in the future, that kind of crowds out serendipity and discovery along the way, is just not my style.”

Our conversation touched on finding unique creators, his philosophy of growth without goals (and rejection of Big Hairy Audacious Goals), the philosophy behind Colossus, world-building founders, game design, collecting and filtering great ideas, and great interviewers.

Stay tuned for part II next week.

Conversation Highlights

‍Finding new podcast hosts doing their life's work.

• “You find these people that are on one of these scent trails and will stop at nothing to stay on the trail. It's infectious. You finish a conversation with him, and you want to run harder at whatever it is you're running at.”
• “The main focus in my career is finding people like this and figuring out how to partner with them, mostly through investing, but sometimes through media. You just do whatever you can to be around them more. The world feeds off the energy of people like David [Senra].”

The power of audio.

• “Audio feels like a secret hiding in plain sight. It's leverage on both sides, and it's unbelievably easier to create something that's great in audio. It's also drastically easier to consume.”
• “And it has an emotional resonance, that the written word just can't match. If you read David's words versus listened to them, some huge percentage of the value would be lost. So that trifecta is amazing to me, much easier to create, much easier to consume, and much more impactful when consumed. Those are what make audio so powerful.”

Learning from experts vs. books.

• “The reason I started my podcast was that I was frustrated by how imprecise even the best book on a topic was, as it related to my specific questions and curiosities. When I went to the world's best expert on whatever, I got exactly what I wanted quickly, with higher impact. I think if you wanted to learn about anything in the world, you'd be far better off, if you could get access to them, spending time with the world's leading thinkers on it and asking them questions directly, than by reading the five or 10 best books on that topic.”

Raising the bar for content.

• “I want the next conversation that I record to be the best one I've done. That's certainly not always the case, or not always true, but we're always trying to think about what makes these good in the first place, and what can make them better.”
• “The ones that I don't enjoy are ones that were sort of not originated from us. It wasn't the result of some curiosity that we had. It was a big name that views us as a New York Times equivalent in the investing industry, and sought us out, and it's hard to say no.”

The guiding philosophy behind Colossus.

• “I'm not striving towards some end state for Colossus. Big, hairy, audacious goals may work some of the time, I'm actually very suspicious of them. I actually think most of the time they're very bad.”
• “I'm incredibly high energy in some regards and I'm incredibly lazy in other regards, which I think is an asset of mine. I think it's good to be lazy in certain ways. My instinct is always that there's something that needs doing that's important, but that I don't want to do. Build infrastructure around it, build systems around it, hire people, hire contractors, create a repeatable system for something that's valuable, but boring to me, and it's usually not boring to someone else.”
• “How do we find as many hosts that we can serve, me being the first. And what can we arm them with to reach a bigger audience and do a better job, and extract as much interesting knowledge as possible? The mindset doesn't need to be any more complicated than that. That will lead us in really interesting directions.”

What's the essence of Colossus?

• “Every single day I spend my days talking to people that I think are at the fringes of distributions. Outliers in intelligence and interest and performance. Extreme people. And it's a compulsion more than it's a commitment. I cannot help myself. I do it every Saturday morning, nonstop, or every day, I'm just doing it. It's what I like to do.”
• “That commitment might be to get rid of the stuff that gets in the way of the compulsion, to protect my schedule. I have a lot of open time, so that I can call these people. Protect time at all costs to do the thing that is your compulsion.”

Finding interesting people.

• “If you're attuned to the thing you're interested in, you see breadcrumbs that are interesting everywhere. People like this tend to be on Twitter. Twitter is a powerful place because it's like a matching algorithm for people like this, but it's everywhere, not just Twitter.”

What makes a good interviewer?

• “I consider myself a very curious person. Moments of joy for me are when I figure out how something works.”
• “I'm just incredibly easily bored. I just cannot stick around something that is boring me. I'm not saying that's just a positive, it can be a large negative too, but that's just how I'm wired. I think that combination of things makes for good interviewers.”

Having a great (podcast) conversation.

• “If you can put the compulsion at the center of your platform, everything becomes much easier. Because I'm compulsive about all this stuff, I'm always preparing. When I sat down for that conversation with Mitch, I didn't prepare at all. I literally showed up at the appointed Zoom hour and started asking questions.”

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The following is an edited transcript of our conversation.

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Frederik Gieschen: I was very happy to see David Senra join Colossus. He takes a book and translates a summary of it into audio. I'm curious what you saw in David.

‍Patrick O'Shaughnessy: I don't think it's very hard. If you listen to David for five minutes to see what I saw in David, I think everyone does, which is insane, curiosity, passion, intensity, and obsessiveness, in his case for biographies of founders through history, and wanting to share that back with an eager audience that's interested in the same topics. And David has used the term “life's work”, something I think a lot about.

David has this quality that is very rare to encounter. You find somebody onto a problem, it doesn't really matter what the problem is. I love how he profiles James Dyson, the vacuum cleaner maker. I don't think there's anything terribly, inherently interesting about vacuum cleaners, which just shows you the problem itself sometimes doesn't matter. But you find these people that are on one of these scent trails and will stop at nothing to stay on the trail and you can just tell that David has it within seconds, if not minutes, of talking to him.. And it's infectious, you finish a conversation with him, and you want to run harder at whatever it is you're running at.

Focus more than you were, be more intentional, think longer term, you know, all these platitudes that everyone pays lip service to in business and investing and then doesn't do, he actually is doing it. And when you find one of those people, which is basically the main focus in my career, is finding people like this and figuring out how to partner with them, mostly through investing, but sometimes through the media, as is the case with David, you just do whatever you can to be around them more. The world feeds off the energy of people like David. And inertia is a hell of a thing, like most stuff just stays the same, so it takes tremendous energy, trajectory and focus to change the status quo. It takes people like him. So that's what we saw in him, is this rare quality of someone doing their life's work with an energy that's hard to understate.

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Frederik Gieschen: You previously mentioned this idea of the Gutenberg Parenthesis and even said that you stopped reading books, or that they should be 1/10th of the length. How do you think about the value of audio, the role of books, and how do you learn?

Audio feels to me like a secret hiding in plain sight. Everyone loves to learn, everyone loves content and loves consuming it, and it seems as though no matter how much great content is created, there's not enough of it. I find myself all the time without a great piece of content to consume. And the demand-supply thing just hasn't reached an equilibrium yet, maybe it never will. And audio is unique in the sense that it is at least 10 times easier to create an unbelievable hour of audio for me, and my format's interview, interviewing someone great like David. That episode between him and I took an hour and a half to record. It will probably be listened to, my guess is, millions of times by the time it's all said and done. An hour and a half for millions of listens. And people will listen all the way through, and they'll consume it all. If you translated that conversation into text, it would be about the length of a short book. If we wanted to create a book of similar quality, it would take a year, probably. I mean I've written a book, it took me a year, and my book was not nearly as good as that conversation with David was.

It's leverage on both sides, and it's unbelievably easier to create something that's great in audio. It's also drastically easier to consume. It takes someone an hour and a half, or if you're like most people, and you listen at one and a half times speed or whatever, it takes less than that. And it has an emotional resonance, that the written word just can't match. If you read David's words versus listened to them, some huge percentage of the value would be lost. So that trifecta is amazing to me, much easier to create, much easier to consume, and much more impactful when consumed. Those are what make audio so powerful.

Now, this isn't some panacea, I want all this stuff. I want great books, great movies, great podcasts, great works of art, and all of it. Some things are perfect in text, so I'm back to reading a lot more books, but usually fiction, you know, very specific kinds of books. I think most non-fiction stuff is better in conversation. The reason I started my podcast way back when was I was frustrated by how imprecise even the best book on a topic was, as it related to my specific questions and curiosities. When I went to the world's best expert on whatever, I got exactly what I wanted quickly, with higher impact. I think if you wanted to learn about anything in the world, you'd be far better off, if you could get access to them, spending time with the world's leading thinkers on it and asking them questions directly, than by reading the five or 10 best books on that topic. That's almost always the case. If I want to learn about something, I am not reading books to start, books are diluted on average, they have to be 224 pages because the stupid binding has to be a certain width. There are all these ridiculous things that drive content formats. So, if I wanted to learn about something new, I would figure out who the five best people are, and I'd get to them, I’d talk to them, I'd ask them questions, and I would probably know more than anyone else that had read every book on the topic.

So that, to me, is the power of audio. It’s just this crazy leverage it represents and the fact that it's the oldest form of communication. Before the written word, we were drawing pictures, and picture stories and certainly audio language is kind of the oldest thing we're aware of. It's incredibly fun, it's incredibly powerful, it's underestimated, and the audience is huge.

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Frederik Gieschen: You said there's not enough great content. Has the bar shifted for you?

Patrick O'Shaughnessy: Has the bar shifted? Yes, hopefully it's always shifting, right? I want the next conversation that I record to be the best one I've done. That's certainly not always the case, or not always true, but we're always trying to think about what makes these good in the first place, and what can make them better. But for me, I need to enjoy the hell out of it. But the ones that I don't enjoy, always suck, and invariably, the ones that I don't enjoy are ones that were sort of not originated from us. It wasn't the result of some curiosity that we had, or that I had, it was a big name that views us as a New York Times equivalent in the investing industry, and sought us out, and it's hard to say no. That happens over and over again, and I'd much rather talk to someone completely unknown that's obsessed about some niche. So yeah, they can always get better, the quality bar should always be going up, and that will always be true. 

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Frederik Gieschen: I think you're investing more in the business than most podcasts and you're building a platform, you have a team, and you bring on people like David and others. Is there a guiding philosophy behind Colossus?

Patrick O'Shaughnessy: I'm not a goals person. I'm not striving towards some end state for Colossus. Big, hairy, audacious goals may work some of the time, I'm actually very suspicious of them. I actually think most of the time they're very bad. Putting a man on Mars, or building a city on Mars, maybe that's an amazing goal, and if anyone can achieve it, it's Elon or these other very ambitious founders, it's just not my personal style. Having a singular goal that's far in the future, that kind of crowds out serendipity and discovery along the way, is just not my style. So, I have no ten year plan for Colossus. I have a perennial plan: how can we produce as many 10 out of 10 audio content episodes as possible? 

The ambition is how do we create multiple a day that are as good as our very best episodes? That's my only real question with Colossus. David is doing that. We encountered David and are like, how do we work with this person? This person is doing what we want to do. Can we join forces in some productive way?

I'm incredibly high energy in some regards, and I'm incredibly lazy in other regards, which I think is an asset of mine. I think it's good to be lazy in certain ways. My instinct is always that there's something that needs doing that's important, but that I don't want to do. Build infrastructure around it, build systems around it, hire people, hire contractors, create a repeatable system for something that's valuable, but boring to me, and it's usually not boring to someone else. Everyone's got different interests and tastes. That looks like ambition from the outside, but in many ways it's really laziness.

In many ways, I'm just Colossus’ main customer, and first customer. And if they can cover all the stuff that I don't want to do for me and do it for others, I think that's a really powerful model on the route to creating more of these really valuable audio conversations or audio episodes.

David's is just him talking, so I don't care about the format. So I just listened to what he did on Henry Clay Frick, and I wanted to learn about him, but I don't want to go read the 1000-page biography, I want to go listen to David talk for 45 minutes at two times speed, and get 90 something percent of it and be energized and have gotten a walk in, rather than sit for two weeks and read this dense biography.

That's the ambition for Colossus. How do we find as many hosts that we can serve, me being the first. And what can we arm them with to reach a bigger audience and do a better job and all those things, and extract as much interesting knowledge from that platform as possible? The mindset doesn't need to be any more complicated than that, and that will lead us in really interesting directions. Where, I don't know.

I never would have guessed that we'd be partnering with David in the way that we are. Or that we’d partner with someone like Will Thorndike, who's an investor that I respect deeply and sort of got me interested in investing in many ways in my early 20s. And now he’s in partnership with us, doing his own show. None of these things were predictable, and weren't a big, hairy, audacious goal, they're just byproducts of this natural search that we're doing. So, we're gonna keep doing that, and I don't know where that goes, but if you want to call that ambition, great, I just think of it as curiosity and wanting to learn, and getting as much of that as possible.

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Frederik Gieschen: You wrote about growth without goals. You said that it meant to commit to something daily and protect it with your life. I guess for you it's being this scout and router of ideas. As Colossus grows as an organization, what's the thing that you're fighting to protect? What's the essence you have to protect?

Patrick O'Shaughnessy: I think the soul, or the essence to protect is just making sure that everyone else has that same mindset. So, let's take Will as an example. The Outsiders is one of the greatest investing books of all time. It's eight companies profiled in eight chapters. Each of those chapters took a year to research. So incredibly deep detail that Will did with graduate students, profiling some very famous CEOs and companies. And in each of those eight cases, it's probably the best piece of content on that company. Maybe not the most thorough or the most in-depth for sure, but the most incisive, or insightful, and most interesting, at least to me. And each of them took a year, it was like an eight-year project to write that book; eight years’ worth of time anyway.

Will, not surprisingly, wants to keep doing that, he wants to build his own podcast, and he owns it, and we're his partner to help produce it and distribute it, and we just don't want to get in his way. We don't care what the format is, but he can't help himself but do this again. 

He just did it for TransDigm, he's gonna do it for other companies, and he has partners too. The format wouldn't be my format. They did four hours on TransDigm, and it was an incredibly deep dive. While I absolutely loved listening to it, I wouldn't create that personally. It wouldn't be my form factor, but we just want to find people that are like that. Commitment is one way of thinking about it. It's not that I'm committed, commitment makes it sounds like it's hard. Compulsion is maybe a more powerful way of thinking about it. Every single day I spend my days talking to people that I think are at the fringes of distributions, like outliers. Outliers in intelligence and interest and performance. Extreme people. And it's a compulsion more than it's a commitment. I cannot help myself. I do it every Saturday morning, nonstop, or every day, I'm just doing it. It's what I like to do. That commitment might be to get rid of the stuff that gets in the way of the compulsion. To protect my schedule, I have a lot of open time, so that I can call these people. Protect time at all costs to do the thing that is your compulsion.

My friend Graham Duncan has this amazing essay on building an investing platform. He has this line in there, it’s like figure out what your compulsion is, and put that at the center of the platform. And if you can do that, and crowd out distractions, you'll probably do a pretty great job. So, whether it's Will, whether it's Jesse Pujji, whether it's Zach Fuss, whether it's David Senra. Any other hosts that we might work with in the future, enable that compulsion and get out of the way.

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Frederik Gieschen: How do you find those people? Does it mostly come organically, one person leads you to the next interesting person, or does it come out of the podcast? How do you go about finding the people at the fringes or the outliers?

Patrick O'Shaughnessy: I find if you're onto a good compulsion, you don't really have to think about the answer to this question. Yes, it's Twitter, it's books, it's conversations, it's in the woods, it's at a dinner party, it's anywhere you are engaging with other people or stuff. You see breadcrumbs, like ooh, that's an interesting tweet. Oh, that book cover looks interesting, or this person seems switched on and isn't just talking about the latest round of golf or some nonsense. It's everywhere. If you're attuned to the thing you're interested in, you see breadcrumbs that are interesting everywhere. And yeah, people like this tend to be on Twitter, so Twitter is a powerful place because it's like a matching algorithm for people like this, but it's everywhere, not just Twitter.

Frederik Gieschen: I've heard you say before that you're a good or great interviewer, but you hate to be interviewed. What do you think makes you or anyone a good interviewer? And how would you say your style or approach to it has changed after hundreds of episodes?

Patrick O'Shaughnessy: I guess at the core, I am very curious about how things work in general. We talked about game design. I'm just very interested in systems, I really like knowing how stuff works. I think I've always been like this, and it's probably innate, and it's cultivated. I consider myself a very curious person. Moments of joy for me are when I figure out how something works. I'm sure everyone's had the experience of some click of understanding. Like a second ago, I didn't understand this, and now I do. That phase transition is a source of tremendous joy for me. I don't know why, it just is. So that's part one. Part two is I'm just incredibly easily bored. I just cannot stick around something that is boring me. I'm not saying that's just a positive, it can be a large negative too, but that's just how I'm wired. I think that combination of things makes for good interviewers. Because if I'm bored, I'm probably a pretty good proxy for the listener, and then they're bored. So, if someone's boring me with an answer, I just completely jump topics, I just get out of that zone. We edit boring stuff out after the fact. 

So, I think avoiding boredom is a great tactic for good interviewing. Your own boredom, not what you think others will want or care about. I think that defines a lot of the great interviewers. If you listen to Howard Stern interviewing somebody, it couldn't be a more different style than me. But I do think those two things are there. He's deeply curious about the people, and he doesn't want to talk about the normal stuff, he wants to talk about weird stuff. He's more interesting, and that's why everyone tuned into Howard Stern for so long. So that, to me, is the recipe. Some sort of innate curiosity and constantly not satisfied with the state of understanding that they have, they want to know more, and they're just bored easily. I think that's true of most of the great interviewers, and it's definitely true of me.

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Frederik Gieschen: How do you strike a balance between preparation and spontaneity in the conversation? What do you look for in a conversation? When do you follow a rabbit hole versus stick to your script?

Patrick O'Shaughnessy: I guess the way I think about this is, if you're always preparing, you don't actually have to prepare. Most of the time, by the time I interview someone, I've already been preparing without meaning to. David is a good example. I was listening to this guy's podcasts, and I was doing it because I wanted to do it, whether or not I ever interviewed him. Same thing for everyone, if I read someone's investor letters, or I see them doing something else, whatever the breadcrumbs are. Sam Hinkie turned me on to that term, “always looking for these breadcrumbs.” There's an amazing blind that Danny Meyer the restaurateur has called ABCD: “always be collecting dots, so that you can always be connecting dots.” Dots or breadcrumbs, if your whole life is oriented around that collection, which mine is, then you're always preparing. 

This Mitch one that we released this morning is just on my mind. Mitch is an unbelievable domain expert. I wish everyone I talked to is like Mitch, in the sense that they've lived their life in an area of deep passion. He was an operator, he was an executive, he was an investor, and enormous success in all three. But first and foremost, he is a fan, he loves the world that he operates in. You can hear it in his voice, and in his answers, like this guy he's got it dead to rights, he just knows it. And so, you could ask the question on that one, How did I prepare for that interview? Well, I prepared for it because I started talking to Mitch years ago about games because I liked games. And I talked to him a lot, and I read a lot of stuff he had written that he sent me. I asked him questions, and I knew his partners at Benchmark, there's just this mosaic of stuff around Mitch. And none of that was because I was like someday I'll interview Mitch, it was because I was interested in it. And so all that was really good preparation. If you listen to that conversation, it sounds like I was really well prepared because I was, I was preparing for years. 

If you can put the compulsion at the center of your platform, everything becomes much easier. Because I'm compulsive about all this stuff, I'm always preparing. When I sat down for that conversation with Mitch, I didn't prepare at all. I literally showed up at the appointed Zoom hour and started asking questions. I did some refreshers, I looked at some notes very briefly, and I never wrote any questions, I never sent topics to the guest, I never do any of that stuff because I'm preparing all the time.

Frederik Gieschen: So, the final recorded conversation is kind of an organic extension of all the conversations or the interactions you've had before. 

Patrick O'Shaughnessy: That's true of almost every one of the best episodes. Of the ones I'm most proud of, that I go back and listen to. It's almost always that same pattern of often years in the making, sometimes more condensed, but often years.

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Frederik Gieschen: If you thought about it as a game and you put yourself back to level zero, and you had the same compulsions and interests, but you hadn't spent the last years building what you've built, how would you go about counter positioning to Invest Like the Best?

Patrick O'Shaughnessy: I've never actually thought of this question. I wish I had some cool answer. This is what I would do differently now to position myself against, but I don't think that's true. I think I would literally do exactly the same thing. And I think that I would get back to where I am now in six or seven years. I don't know if there's like a trick here. I think what you get on my podcast is just me, it's not a character I'm playing, it's just me, and that's a very sustainable strategy. And so, it's very hard for me to imagine if I started with zero audience today, that I could or would do anything different. Because I think in the long run, the only thing that is sustainable in this specific example is being yourself. So, if you're not that, it's not going to work, and if you're not committed for the long term, it's not going to work. If you want quick wins, do not start a podcast. It's a terrible idea because it takes time, and people commit to new ones reluctantly. And then usually, once you commit, you get a new listener, and if your show is good, you'll have them forever.

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