Episode 16: Barry Ritholtz - Chairman of Ritholtz Wealth Management

This week, I had the distinct honor of speaking with Barry Ritholtz, one of the most original and influential voices in modern finance, and the co-founder, chairman, and CIO of Ritholtz Wealth Management. With a career that has spanned law, trading, strategy, and media, Barry’s unique path has given him a perspective that few in the industry can match.

After beginning his professional life as a lawyer, Barry made the unconventional leap into finance—first as a trader, then as a strategist, and ultimately as the architect of one of the fastest-growing wealth management firms in the U.S. Alongside Josh Brown, he built Ritholtz Wealth Management on the foundation of transparency, evidence-based investing, and a deep respect for behavioral finance.

Barry’s latest book, How Not to Invest, is a culmination of decades of experience studying markets, investor psychology, and systemic failures. Rather than offering yet another formula for beating the market, the book takes a different approach—highlighting the most common mistakes investors make and the thinking traps that lead to underperformance. Organized into three categories—bad ideas, bad numbers, and bad behavior—it’s a guide for avoiding the pitfalls that derail so many investment journeys.

In our conversation, we covered Barry’s unconventional upbringing, the twists and turns of his career, and the mental models that have shaped his approach to investing and decision-making. We also dug into the principles behind his book, his thoughts on media consumption, and how young people can navigate their own paths in an increasingly noisy world.

I hope you enjoy this episode as much as I did.