Bill Bernstein: 50 Years of Investing Wisdom

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?
01:03:50 The future of Social Security
01:07:00 Closing thoughts and book recommendations

LINKS:

The Four Pillars of Investing — Bill Bernstein (2nd ed., 2023)

If You Can — Free PDF from Bill Bernstein

The Bessembinder Study — "Do Stocks Outperform Treasury Bills?"

Bainbridge Community Foundation

Ben Carlson's New Book on Risk and Reward