Mar 24 2025 67 mins 229
What do weddings, wineries, and Whoppers have to do with smart investing? This week, Joe, OG, and Doug kick off the episode with stories from the road—including a surprise credit card confession that somehow involves a Burger King (because of course it does).
But then the gang shifts gears and dives into real money talk, breaking down investing wisdom from the legendary Barry Ritholtz. From navigating market cycles to keeping your emotions in check, Barry’s top 10 tips serve up the kind of grounded, no-BS advice your portfolio will thank you for—especially the next time the market gets jumpy or the headlines go haywire.
They also tackle what politics really mean for your investments (spoiler: maybe less than you think) and why getting your expectations right could be the most important investment decision you make.
Stick around to hear a listener question that hits close to home: How should you invest for an 84-year-old mom? It’s a multigenerational money moment that brings the discussion full circle.
Here’s what you’ll learn:
- Why market cycles matter (and how to avoid getting whiplash)
- The hidden dangers of investing with your heart instead of your head
- What Barry Ritholtz says about predicting political impacts on your portfolio
- How to set realistic return expectations (and why that’s surprisingly freeing)
- A practical investing strategy for elderly parents—without the jargon
- Plus: Doug’s trivia takes a nostalgic turn into the wild world of Beanie Babies
FULL SHOW NOTES: https://stackingbenjamins.com/how-not-to-invest-1660
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
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