Why Smart Investors Still Make Bad Decisions | Barry Ritholtz

What if your biggest investing risk is not the market, but your own behavior?In this episode of Executive Connect, Melissa Aarskaug sits down with Barry Ritholtz, co-founder of Ritholtz Wealth Management, to talk about why intelligent investors still make costly mistakes. Barry breaks down the psychology behind bad financial decisions, the danger of overconfidence, why so many people follow terrible advice online, and how behavior often matters more than information. He also shares lessons from major market moments, what AI can and cannot do for investors, and why simple discipline still beats flashy predictions.This episode is for investors, executives, and high earners who want to build wealth without letting noise, ego, or fear wreck the plan. Press play before your next money decision gets made on emotion instead of discipline.What You Will LearnWhy investor behavior matters more than most people realizeHow fiduciary advice differs from traditional Wall Street incentivesWhy social media financial advice can be dangerousThe cognitive biases that quietly wreck portfoliosWhy smart professionals often struggle with investing disciplineHow to think about compounding, planning, and long-term wealthWhat past market crises reveal about investor psychologyWhere AI can help investors and where it still falls shortChapters (0:00) Start with a real financial plan (0:50) Why behavior beats information (2:17) From lawyer to investor (4:48) Why fiduciary advice matters (12:27) The danger of finfluencer advice (17:18) How behavior drives investing results (22:33) Biases that wreck portfolios (32:20) Wealth-destroying habits to avoid (38:48) Lessons from past market calls (48:42) Where AI helps investors (55:58) The tennis lesson for investingGuest Bio Barry Ritholtz is the co-founder of Ritholtz Wealth Management, an independent, employee-owned advisory firm managing billions in assets. Before building the firm, Barry trained in law, started his career as an attorney, and later moved into trading and investing. Over the years, he has become known for cutting through market myths, challenging weak financial thinking, and helping investors make smarter decisions with clearer processes and better discipline.Connect with Barry RitholtzWebsite: https://ritholtz.com/LinkedIn: https://www.linkedin.com/in/ritholtz/Grab a copy: https://www.hownottoinvestbook.com/Connect with Executive ConnectWebsite: https://www.executiveconnectexperience.comLinkedIn: Melissa AarskaugYouTube: Executive ConnectInstagram: @executiveconnectpodcastTikTok: @executiveconnectpodcastFacebook: Executive Connect