How a $17B Investor Beat Wall Street By Reading Shakespeare

How to Combine Action with Contemplation

It’s rare to find someone who is a thinker and a doer. My guest Jim O’Shaughnessy is one of them: a legendary Wall Street investor who has an unquenchable thirst for the humanities. 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 has also become a friend. Patrick studied philosophy at Notre Dame and is now one of the top venture capitalists. I thought: Huh? Rarer still. 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 oilmen in the 20th century, trained in the liberal arts, and was the 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.

Topics We Cover:

2:38 Humanities: The Entrepreneur’s Last Edge

18:46 Philosophy Applied To Life

27:29 Religion is a Power Play

30:24 The Eastern/Western Overlap

35:59 Psychoanalyzing Wall Street

46:03 Investing Requires Encyclopedic Knowledge

1:06:29 Betting on Culture in The AI Age

1:30:51 Mind-Body Divide: A Western Ailment