DiscoverJake and Gino Multifamily Investing EntrepreneursHow Not to Invest with Barry Ritholtz: Behavioral Finance, Indexing & Timeless Strategies | Jake & Gino show
How Not to Invest with Barry Ritholtz: Behavioral Finance, Indexing & Timeless Strategies | Jake & Gino show

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

Update: 2025-11-10
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 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

We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/


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

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

Barry Ritholtz, Jake Stenziano, Gino Barbaro