We Study Billionaires - The Investor’s Podcast Network TIP732: The Mindset and Skills That Build Investing Legends w/ Ian Cassel
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Jun 27, 2025 
Ian Cassel, who manages a high-performing fund since 2019, explores the mindset of legendary investors. He delves into five essential skills that lead to stock-picking success and emphasizes the importance of radical self-honesty for improvement. Drawing parallels to Brazilian Jiu-Jitsu, he discusses the adaptability and psychological resilience needed in investing. Cassel also shares insights on distinguishing good investors from great ones, highlighting the hidden skills that provide an edge and the balance between offensive and defensive strategies in portfolio management.
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Tom Kite's Concentration Anecdote
- Tom Kite, a top golfer, explained concentration loss shifts outcomes from winning to missing the cut.
- One or two strokes lost per round differentiates top players by a sliver but with huge outcome differences.
Time and Return Define Skill
- Investing success is judged mainly by time tested returns and how long the record lasts.
- Short-term outperformance is common, but sustained performance over years truly reflects skill.
Benchmark Against S&P 500
- Compare your investment performance against the S&P 500 as it is the toughest benchmark.
- Embrace volatility if pursuing absolute returns; set client expectations accordingly.
