
Johnathan Bi How a $17B Investor Beat Wall Street By Reading Shakespeare | Jim O'Shaughnessy
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Jan 3, 2026 Jim O'Shaughnessy, an influential investor and philanthropist, discusses how a love for the humanities shaped his financial strategies. He shares insights on family traditions of curiosity and intellectual exploration. Jim delves into the impact of Eastern philosophy on his temperament and the emotional dynamics of investing. With a fascinating journey from handwritten letters to algorithmic strategies, he emphasizes the importance of adaptability and learning from mistakes. Additionally, he explores the future of publishing with AI and reflects on the cultural mission of his ventures.
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Study Humans For Durable Edge
- Human nature changes far slower than markets, so studying humans yields durable investment edges.
- Jim O’Shaughnessy calls this 'arbitraging human nature' as the last sustainable advantage.
Letters For Future Children
- Jim started writing handwritten letters to his children beginning when his oldest was six days old and planned to give them at 21.
- He kept them unedited to let his kids see who he was at each age and how he changed.
Reread Books At Different Ages
- Rereading favorite books at different life stages reveals new meanings and practical lessons.
- Jim learned the Dao De Jing and other classics gave different guidance as he matured.










