In this episode of Joe's Happy Hour, Joe Fahmy welcomes Mike Webster, Senior Market Strategist at Investor’s Business Daily, for an engaging, deep-dive conversation into the history, philosophy, and practical lessons of stock trading. They discuss Mike’s journey working with investing legend William O’Neil, the psychological traps traders fall into, how historical patterns continue to shape modern markets, and why flexibility, humility, and discipline are essential in trading. Packed with anecdotes, market wisdom, and humor, this is a must-listen for investors at any level.00:00 – Intro & Mike Webster’s Background01:10 – Influential Investing Books02:15 – Studying Market History: 1880s to Now04:00 – Rebuilding Pre-1960 Charts by Hand05:50 – Validating O’Neil’s System Across Eras07:10 – Market Bubbles: Railroads to Dotcom08:10 – Bill O'Neil’s Frugality & Vision09:20 – Mike’s Entry into Finance & IBD10:55 – 1600% Return and Early Swing Trading12:45 – Gaining Bill O’Neil’s Trust14:15 – Co-Managing O'Neil’s Institutional List16:00 – Bill O'Neil’s Flexibility in Market Interpretation18:10 – Importance of Cutting Losses & Avoiding Hope20:50 – Why Most Stocks Don’t Come Back23:30 – Personal Advice from Bill: “Sell 6%”26:00 – Life Lessons: Helping Others & Giving Back28:00 – CD Collection to Trading Capital30:00 – The Logic Behind Sharing Market Knowledge32:00 – The Stress of Managing Concentrated Portfolios34:00 – Building Market Recall Through Chart Volume36:00 – Charting is a Learned Skill, Not a Gift38:00 – Active Trading vs. Dollar Cost Averaging40:30 – Risk of Treating Trading Like Gambling42:10 – Why Rules Matter for Every Trader43:45 – Position Sizing: From 5% to Full Margin45:30 – Lessons in Holding vs. Selling Too Early48:00 – The “Quick, Quicksand, Grateful Dead” Framework50:30 – Creating Tools for Traders, Giving It Away Free52:00 – Mike’s Podcast & Sharing Legacy with Kids54:00 – Where to Find Mike Webster’s Work56:30 – Balancing Life, Markets, and Purpose58:00 – Final Reflections on Career and Perspective

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