Hello everyone,

A few months ago I had the pleasure of interviewing Patrick O’Shaughnesssy, the prolific host of Invest Like The Best, as part of my work for Compound.

We started our conversation on the topic of David Senra, host of the amazing Founders podcast, who had just joined Patrick’s Colossus podcasting platform. David is one of the most focused people I know. Patrick one other hand is prolific but involved in a variety of efforts. Aside from podcasting, there is his venture capital firm Positive Sum, he is the CEO of O’Shaugnessy Asset Management, and he co-hosts Capital Camp.

“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.”

I was very interested in finding the unifying themes and the philosophy behind his work. Curiosity is a big driver for Patrick.

“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.”

If Patrick is a fox, his mission is to find hedgehogs whose knowledge he can tap into.

“It turns out that a podcast (a media business) and an investing firm are two really great things to have when your game is people-centric. Your game is effectively searching for interesting people. Being able to interview them and or invest in them are kind of the two most fun things to be honest with you. It's a great way for me to have a world around my interests. And in our investing activity, this is something we explicitly look for, we call it world building.”

On the topic of David and Founders, Patrick hit the nail on the head. It’s electrifying to meet someone on a mission.

“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.”

‍You can listen to our conversation on Spotify, Apple, anchor (and via RSS) or find a full transcript at Compound (part I, part II).

If you’re looking for an all-in-one solution to manage your personal finances, Compound can help (disclosures).

A few things I learned from Patrick:

Follow authentic curiosity and joy.

“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.”

“I expect to do very well in the things that I do, not because I want some achievement badge, but because the process of doing that is joyful to me.”

Conversation as a game.

“To me, conversation is kind of like a game. I'm always interested in how much more interesting I can make a conversation that I'm in. I don't do small talk well. If I'm at a party, I'm always interested in how interesting something could get relative to the baseline.”

Eastern philosophy as an operating system for life.

“If you put a lot out there for others, with no expectation of a selfish return, you end up actually getting more than if you didn't do that. It's a strange worldview, because it's not a business school case study. The inputs and the outputs don't connect via some formula. You have no idea how it's going to come back to you.

It is my form of faith. If I do this, it will come back. I have no idea how, but it will, and that's been my experience too. But if you were just trying to approach something strategically, irrationally, you would never behave this way because you can never tie the input to the output.”

On working with founders.

“Investors, I think, mistake a founder's desire for their capital for a founder’s desire for them, and all the things that come with them."

“My experience is that founders want the capital to fuel their business, and they want someone that they can have as a confidant, that they can trust, that they can call when needed. But they don't want a steady stream of ideas and advice. The classic one is, have you seen this competitor yet? Some large percent of texts from VCs to founders is like the website of a competitor. What I think we can do is ask really good questions, the theme in my life, and not mistake what a customer actually wants from us for what we think they want.”

The good life.

“I optimize for learning, I optimize for freedom of time, to be with my family, especially. Learning, reading, talking to people, spending time with people, moving in the woods, ideally, or outside somewhere on the water somewhere with my family and my friends.

Everyone has something they love, or a set of things they love, but very few people really work to protect those things. And to structure their life so that they get as much of the things they love, and get joy from as they can.”

Growth without goals, the guiding philosophy behind Colossus.

See also Patrick’s essay on the topic.

“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.”

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Gwendolyn Wright: America and the spirit of modernity.