Why do smart, well intentioned investors still make costly mistakes? In this episode, I sit down with Barry Ritholtz to explore why investing success has less to do with intelligence and more to do with behavior. Barry explains how bad ideas, bad numbers, and bad habits quietly derail portfolios, even for people who know better. We talk about how to think probabilistically instead of emotionally, why markets do not crash on a schedule, and what actually brings bull markets to an end. We also dig into the limits of forecasting, how to evaluate market commentary without getting swept up in hype, and where artificial intelligence truly fits into modern investing. This conversation is not about predicting the next crash or chasing the next trend. It’s about building a decision-making process that works across uncertainty, volatility, and long time horizons. Key Takeaways Most investing mistakes come from bad ideas, bad data, or bad behavior, not from lack of access to information. Good investing decisions should be judged by process, not by short-term outcomes. Markets do not crash because they are “old” and recessions do not arrive on a calendar. They require a catalyst. Thinking probabilistically helps investors prepare for a range of outcomes instead of anchoring to a single prediction. Large language models are powerful tools for efficiency, but they are not replacements for human judgment or original thinking. Following commentators requires evaluating their incentives, temperament, track record, and consistency, not just their confidence. Resources Barry's Blog: https://ritholtz.com/ Rithotltz Wealth Management: https://www.ritholtzwealth.com/ Barry's Book - How Not to Invest: https://amzn.to/3LPaxPu Chapters (00:00) Introduction: Why focusing on investing mistakes matters (03:00) Does avoiding mistakes make investors too conservative? (06:30) The three categories of investing mistakes (10:45) How to tell good investing ideas from bad ones (16:30) Process vs outcome: evaluating decisions correctly (23:00) Probabilistic thinking, risk, and market uncertainty (30:00) Market crashes, downturns, and long-term opportunity (38:30) Why recessions and bull markets don’t run on a calendar (47:00) Market commentators, archetypes, and investor bias (55:30) Luck vs skill, halo effects, and knowing who to trust _______________ Subscribe via Apple Podcasts: https://affordanything.com/applepodcasts Full show notes for the episode: https://affordanything.com/episode Get our show notes in your inbox: https://affordanything.com/shownotes Follow us! IG: https://instagram.com/paulapant Twitter: https://twitter.com/affordanything FB: https://facebook.com/affordanything Community: https://affordanything.com/community