Podcast Episodes
Back to Search2026 March Market Cap Madness: Emily vs. Bill (BEMILY 2!)
The Madness continues! This week on Rule Breaker Investing, the second semifinal of March Market Cap Madness tips off as defending world champion Emi…
2 months, 1 week ago
2026 March Market Cap Madness: Andy vs. Loren
March Market Cap Madness tips off its Final Four this week on Rule Breaker Investing, and you’re not just watching—you’re playing. Past world champio…
2 months, 2 weeks ago
February 2026 Mailbag: Countless… Right?
This week’s Mailbag picks up where Pet Peeves left off—and then some. Listeners write in with their own linguistic grievances, from “10 straight unan…
2 months, 3 weeks ago
Pet Peeves, Vol. 9: Buy Now, Pay Later… Right?
It’s been 27 months since this series’s last installment, which means David has had time to quietly bottle up a fresh batch of entirely new irritatio…
3 months ago
10 Years Later: 5 Stocks to Feed the Bear
Ten years ago this week, in the teeth of a downturn, David picked five stocks under the banner “5 Stocks to Feed the Bear.” This week, he and longtim…
3 months, 1 week ago
Let’s Talk About the Future in 2026 with Kevin Kelly
Kevin Kelly—founding editor of Wired magazine and a lifelong observer of technology in motion—returns to Rule Breaker Investing for a conversation ab…
3 months, 2 weeks ago
January 2026 Mailbag: Values, Kids, Games & Inspiration
This week’s Rule Breaker Investing Mailbag brings together beautiful questions and stories to start the new year. We wrestle with a values-alignment …
3 months, 3 weeks ago
Calculating Risk Foolishly, Vol. 4: ETSY v. DUOL
Risk gets talked about a lot in investing—and often defined poorly. This week on Rule Breaker Investing, David is joined by Motley Fool analysts Alic…
3 months, 4 weeks ago
Healing Leaders: An Inside-Out Path to Better Decisions
This week on Rule Breaker Investing, David is joined by Raj Sisodia and Nilima Bhat, co-authors of Healing Leaders, for a conversation about leadersh…
4 months ago
Essays From Yesterday, Vol. 8
As we open 2026, David looks backward to get clearer about what really matters going forward. In the eighth installment of Essays From Yesterday, he …
4 months, 1 week ago