Episode
Bill Bernstein: 50 Years of Investing Wisdom
- Podcast
- Sound Investing
- Published
- May 20, 2026
- Duration seconds
- 4243
- Processing state
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Summary
In this interview from the 2026 Bainbridge Community Foundation Annual Financial Education Series, Paul sits down with Bill Bernstein — neurologist, financial historian, and author of The Four Pillars of Investing and If You Can — for a wide-ranging conversation drawn from 50-plus years of investing experience. Bill explains why you're only rewarded for taking risk in well-regulated markets (and why crypto doesn't qualify), how today's market echoes the late 1990s, why the "reverse glide path" makes sense the older you get, and what the Bessembinder research really tells us about the cost of trying to pick winners. Paul and Bill also debate withdrawal strategies, the case against long bonds, and whether tilted small-value investing still works once "the bozos know about it." A masterclass in evidence-based investing from one of the most respected voices in the field. CHAPTERS 00:00 Intro from Matt Longmire, Bainbridge Community Foundation 02:50 Welcoming Bill Bernstein 03:50 Why The Four Pillars of Investing belongs on every DIY investor's shelf 05:50 Risk vs. reward — and why Bitcoin doesn't qualify 08:30 How many asset classes do you really need? 11:50 Where today's market resembles the late 1990s 13:40 Are REITs still worth holding? 15:50 The case for automating everything 19:45 Why retirees need to fear sequence-of-returns risk 21:30 Paul's 5% rule vs. the 4% rule 25:30 The two-bucket theory and the reverse glide path 27:30 Prediction markets, gambling, and "being the house" 32:00 The sociological signs of a bubble 35:00 Speculation vs. gambling — gold's real return 40:00 The Bessembinder study: why 4% of stocks make most of the returns 46:00 Why rich people plan three generations ahead 49:00 Audience Q&A 58:30 Tilted index funds (DFA, Avantis) — worth it? 01:0…