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

Jake and Gino Multifamily Investing Entrepreneurs

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

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