The Long View

Jim O’Shaughnessy: Investing Lessons From a Lifelong Learner

49 snips
Feb 17, 2026
Jim O’Shaughnessy, founder of O’Shaughnessy Asset Management and author known for What Works on Wall Street, reflects on quantitative investing and lifelong learning. He digs into price versus narrative, how quant methods avoid emotional pitfalls, long-term portfolio and bond roles, and what matters in pre-seed founder selection and valuations. He also shares the origin of his quotes book and his Infinite Loops podcast.
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INSIGHT

Price Precedes Narrative

  • Price tends to lead narrative; narratives often form to justify price moves after the fact.
  • When narrative dominates valuation, prospective returns over the next 3–5 years often suffer.
ANECDOTE

1987 Lesson In Emotional Bias

  • In 1987 Jim sold large put positions a day before the crash after succumbing to peers' advice.
  • That mistake taught him to trust quantitative signals over crowd emotion going forward.
ADVICE

Think Like Your Future Self

  • Invest with a long-term horizon and use bear markets to add shares rather than panic.
  • Keep portfolios simple and aligned with your future-self goals.
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