The Stacking Benjamins Show

Even the Pros Are Wrong Half the Time. Here's What They Do Differently SB1820

20 snips
Mar 25, 2026
Lee Freeman-Shor, an investment manager and author who studies fund manager behavior, and Claire Flynn Levy, founder of Essentia Analytics and former CIO, discuss how top investors win by process not pick accuracy. They cover why pros are often wrong, rules-based selling and sizing, handling losers and letting winners run, and real-world case studies on repeatable systems and market quirks.
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ADVICE

Let Winners Run Don’t Bank Small Gains

  • When positions win, be a connoisseur and let winners run instead of banking small gains as a raider.
  • The maestros show two or three big winners usually account for most returns, so avoid selling winners after 10–20% routinely.
INSIGHT

Use Signals And Data Driven Holding Periods

  • Strong execution relies on signals and holding-period rules, not prediction.
  • Josh Goldberg waits for earnings surprises, then typically holds ~15 months as his statistical sweet spot before re-evaluating.
ADVICE

Ask Would I Buy This Today Before Holding

  • When reviewing losers, ask honestly: would I buy this today at the current price with current info?
  • Use that direct question as a checklist trigger to overcome loss aversion and sell if the answer is no.
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