Investor Mistakes, Financial Media Noise, and the Case for Consistently Being Less Wrong
After 30 years in markets, Barry Ritholtz didn't write a book about how to invest. He wrote a book about all the ways we get in our own way — because that turns out to be a more useful guide.
The premise of How Not to Invest is simple: consistently being less wrong beats occasionally being very right. The execution is witty, irreverent, and backed by 279 documented mistakes. Some of them are his.
Chopping Wealth is Shaping Wealth's flagship conversation series — where Brian Portnoy goes deep with the sharpest minds in investing, psychology, and human behavior.
In this episode, Brian sits down with Barry Ritholtz — founder, chairman, and CIO of Ritholtz Wealth Management, host of the Masters in Business podcast, and one of the most widely-read voices in finance — for a conversation about investor mistakes, the inversion principle, what money is actually for, and why Charlie Ellis and Charlie Munger deserve a joint dedication page.
If you work with investors — or are one — this one will make you smarter, and probably laugh.
What you'll take away:
Why "less stupid, less often" beats "smarter" as an investment philosophy
The winner's game vs. the loser's game — and which one your clients are actually playing
Barry's own worst mistakes: the Apple trade, the Robinhood pass, and what they teach
What money actually is — and why most people have never really thought it through
How social instincts and cognitive wiring set investors up to fail
The full library lives on Compass — Shaping Wealth's learning platform built exclusively for financial advisors ready to go deeper on the human side of advice.
🌐 https://compass.shapingwealth.com/
Already on Compass? Meet Lydia — Shaping Wealth's AI behavioral coaching tool for advisors who want to put this work into practice with every client. She's live now. https://meetlydia.ai/
👉 Watch now for 30 years of hard-won perspective on what it means to actually invest well.
👍 Like the video if Barry's inversion framework shifted something in how you think about advice
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💬 What's the investing mistake you've seen most often — in clients or in yourself? Drop it below.