Johnathan Bi

Johnathan Bi

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Transcript of Interview with Jim O'Shaughnessy

An interview with Jim O'Shaughnessy on the life of contemplation and action

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Johnathan Bi
Jan 03, 2026
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Chapter 0. Introduction

Johnathan Bi: It’s rare to find someone who combines action and contemplation. And that’s my guest, Jim O’Shaughnessy, a legendary Wall Street financier who has an unquenchable thirst for the humanities as a student, patron and writer. I met Jim a couple of years ago when he first interviewed me on Girard, and we became fast friends because of how rare that combination is. And then I met one of his sons, Patrick, who’s also become a friend. Patrick studied philosophy and is now one of the top venture capitalists. And then I thought, huh, rare still. But then, as I was preparing for this interview, I came across a book written about Jim’s grandfather, IA O’Shaughnessy who was one of the most successful oil men in the 20th century.

Johnathan Bi: He trained in the liberal arts. He was the then largest donor to Notre Dame, who endowed the Humanities Building. It’s rare enough to synthesize action and contemplation in one individual. How does one sustain that across now four generations? That’s what we will begin this interview discussing before talking about how Jim’s love of the humanities shaped his varied career across finance, media and philanthropy. My name is Johnathan Bi. I’m a founding member of Cosmos. We deliver educational programs, fund research, invest in AI startups, and believe that philosophy is critical to building better technology. If you want to join our ecosystem of philosophy builders, you can find roles we’re hiring for, events we’re hosting, and other ways to get involved on johnathanbi.com/cosmos. Without further ado, my friend, Jim O’Shaughnessy.

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