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