EP.005 Jason Shapiro with Jeff Boccaccio

  • May 4, 2025

Jason Shapiro

Jeff Boccaccio chats with fund manager Jason Shapiro on Why Money Can’t Buy Freedom: A Journey from Monastery to Markets

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Overview

In this episode, Jeff Boccaccio interviews Jason Shapiro, a well-known contrarian trader and an initially reluctant participant in Jack Schwager's 'Unknown Market Wizards.' Jason discusses his current trading strategies, the stresses of trading and the tolls it can take along with how he incorporates the Commitment of Traders (COT) report into his decision-making process. He also shares personal anecdotes about his life, including a transformative experience spending a month in a Buddhist monastery in Burma and how it shaped his views on freedom and wealth. The episode packs valuable lessons on trading psychology, maintaining discipline and how his last minute decision to be included in ‘Unknown Market Wizards’ has led to a fulfilling community of traders at the Crowded Market Report.


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Topics:

  • 00:00 Introduction and Personal Reflections on Wealth

  • 01:01 Current Market Focus and Trading Strategies

  • 01:27 Insights on Gold and Market Sentiment

  • 02:14 Contemplating Retirement and Life Choices

  • 03:07 Jason Shapiro's Background and Monastery Experience

  • 08:41 Lessons from the Monastery and Life Reflections

  • 21:21 Trading Philosophy and Community Engagement

  • 33:42 Reflections on Market Wizards and Legacy

  • 38:33 Struggles and Discipline in Trading

  • 40:27 Managing Investor Expectations

  • 41:43 Running a Small Trading Shop

  • 43:45 Starting a Hedge Fund or CTA

  • 48:58 Systematic vs. Discretionary Trading

  • 56:07 Position Sizing and Risk Management

  • 01:02:54 Client Relationships and Correlation

  • 01:05:50 Personal Investments and Retirement Accounts

  • 01:09:12 Understanding the Trading System

  • 01:10:46 Trade Execution and Position Sizing

  • 01:11:31 Profit Exits and COT Reports

  • 01:15:57 Risk Management and Learning from Mistakes

  • 01:20:26 Trade Timing and Execution

  • 01:27:24 Community Insights and Market Analysis

  • 01:34:35 Final Thoughts and Resources

For more information about Jeff Boccaccio & Rfactory visit us at https://www.rfactory.io

For more information about Jason Shapiro &the Crowded Market Report visit https://www.crowdedmarketreport.com/


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