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How Not to Invest with Barry Ritholtz: Behavioral Finance & Timeless Strategies | Jake & Gino show

Wall Street noise is loud—Barry Ritholtz shows you How Not to Invest. In this episode, we cut through models, headlines, and hype to focus on the few decisions that actually compound.

Barry shares a practical framework for decision-making grounded in behavioral Finance: why models are “wrong but useful,” how to build a checklist to filter signal from noise, and why broad indexing should anchor most portfolios. We dig into direct indexing for tax management, the attention Economy’s impact on investors, and the real effects of tariffs and Fed timing on markets and Main Street. He also maps the “two businesses” every investor must master: deploying capital quietly for decades and consuming information without getting captured by clickbait. If you’re curious about AI’s productivity boost, global mean reversion beyond the U.S., and realistic expectations after back-to-back strong years, this conversation is for you. By the end, you’ll know How Not to Invest—and what to do instead.

Connect with Barry Ritholtz: hownottoinvestbook.com

Chapters:
00:00 – Introduction
02:32 – “All models are wrong, some are useful” & avoiding media-driven fear
16:21 – Wealthy vs. middle-class planning: indexing, direct indexing, tax loss harvesting
20:19 – AI’s real impact on advisors, workflows, and productivity
24:46 – Where are the opportunities? U.S. vs. developed ex-U.S., mean reversion
35:14 – Rates, the Fed, soft landing probabilities & realistic return expectations
49:33 – Gino wraps it up

Gino Barbaro is a Multifamily educator, Investor, and Operator with over $350,000,000 in assets under management. As co-founder of Jake & Gino, the premier multifamily education community, he focuses on his students’ results and growth. To date, his students have closed over 76,000+ units and have $5 Billion in Deal volume! Gino also co-authors the best-selling books, Wheelbarrow Profits & The Honey Bee. He resides in St. Augustine, Florida with his beautiful wife Julia and their six children.