Investing by the Books Investing by the Books

#88 Ian Cassel: Stock Picker

Sep 22, 2026 · 1h 14m

Summary

Ian Castle discusses his new book, *Stock Picker*, detailing his journey from a high school investor to a full-time microcap fund manager. He reflects on how his upbringing and early wins in the dot-com bubble shaped his risk tolerance and passion for small-cap stocks. The conversation covers the distinct phases of microcap investing, the importance of building relationships with management teams, and the evolution of his strategy from story stocks to quality businesses. Castle also addresses the stigma surrounding microcaps and the critical role of capital raising in these companies.

Topics discussed

Introduction to Ian Castle and his book 'Stock Picker' Ian's background and the decision to write the book Upbringing in Lancaster and its influence on investing First exposure to stocks and the dot-com bubble The impact of the 2000 crash and first big win The XM Satellite Radio story and obsession with microcaps The stigma of microcaps and the 'penny stock' label European vs US microcap markets and discovery phases Investing in sub-$50M nano caps and market dynamics Evolution of investment styles: story stocks to deep value The importance of management relationships and due diligence Common mistakes and the risk of capital dilution Portfolio concentration and the 'life is too short' philosophy Battle scars: selling winners and the auditor scandal Becoming a full-time investor and avoiding outside capital Launching the fund and finding the right investors Building the MicroCap Club community and reputation Institutional behavior and liquidity in microcap stocks Evolution of portfolio size and position sizing Monitoring stocks and emotional detachment from prices Reading habits, writing process, and closing remarks
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