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 Background
01:10 – Influential Investing Books
02:15 – Studying Market History: 1880s to Now
04:00 – Rebuilding Pre-1960 Charts by Hand
05:50 – Validating O’Neil’s System Across Eras
07:10 – Market Bubbles: Railroads to Dotcom
08:10 – Bill O'Neil’s Frugality & Vision
09:20 – Mike’s Entry into Finance & IBD
10:55 – 1600% Return and Early Swing Trading
12:45 – Gaining Bill O’Neil’s Trust
14:15 – Co-Managing O'Neil’s Institutional List
16:00 – Bill O'Neil’s Flexibility in Market Interpretation
18:10 – Importance of Cutting Losses & Avoiding Hope
20:50 – Why Most Stocks Don’t Come Back
23:30 – Personal Advice from Bill: “Sell 6%”
26:00 – Life Lessons: Helping Others & Giving Back
28:00 – CD Collection to Trading Capital
30:00 – The Logic Behind Sharing Market Knowledge
32:00 – The Stress of Managing Concentrated Portfolios
34:00 – Building Market Recall Through Chart Volume
36:00 – Charting is a Learned Skill, Not a Gift
38:00 – Active Trading vs. Dollar Cost Averaging
40:30 – Risk of Treating Trading Like Gambling
42:10 – Why Rules Matter for Every Trader
43:45 – Position Sizing: From 5% to Full Margin
45:30 – Lessons in Holding vs. Selling Too Early
48:00 – The “Quick, Quicksand, Grateful Dead” Framework
50:30 – Creating Tools for Traders, Giving It Away Free
52:00 – Mike’s Podcast & Sharing Legacy with Kids
54:00 – Where to Find Mike Webster’s Work
56:30 – Balancing Life, Markets, and Purpose
58:00 – Final Reflections on Career and Perspective