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Blast From The Past, Vol. 12: ABB
Some truths are too good to say only once. This week, David re-blasts five timelessly powerful ideas from the past—about identity, investing, serenity, frameworks, and questioning—and brings them together in a fresh 2026 mix. One quietly po
March 2026 Mailbag: Habits, Hacks & “Boom”
March Madness may be over, but the Mailbag is just beginning—and as always, you’re the star of the show. This month we hear from listeners who tracked the data on our Market Cap Game Show strategies (does “always disagree”… really work?), r
2026 March Market Cap Madness Championship: Loren v. Emily
The bracket is complete. The stakes are highest. And now… it’s time to crown a champion. This week on Rule Breaker Investing, defending champion Emily Flippen faces off against Cinderella challenger Loren Horst in the March Market Cap Madne
2026 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 Emily Flippen faces long-time Motley Fool advisor Bill Barker for a place in the championship
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 champion Andy Cross (6–1 lifetime) squares off against Cinderella contender Loren Horst (1–0) in o
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 unanswered points” to the curious inflation of words like “countless,” to the conversational re
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 irritations—all original, no repeats. This year’s edition takes aim at the slippery phrase “Buy Now,
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 longtime Fool Rick Munarriz revisit that full basket—not after a month, a quarter, or a year, but
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 about how the future actually shows up. We don’t trade in predictions here. Instead, Kevin sh
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 dilemma around owning Robinhood, explore what it looks like to turn investing into a real,
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 Alicia Alfiere and Yasser El-Shimy to walk through his full 25-point risk rating system, a fram
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 leadership burnout, meaning, and why wholeness may be a strategic advantage. Rather than treating h
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 revisits four Rule Breaker essays written between 2006 and 2014—spanning market sell-offs,
December 2025 Mailbag: “Am I a Fool?”
It’s the final Rule Breaker Investing podcast of 2025, and the year ends as it always does—with your Mailbag. David shares his annual year-forward market call, then works through listener notes that capture the heart of the Foolish journey.
Market Cap Game Show: Bubble Wrap & Sidewalk Robots
It’s time once again for the Market Cap Game Show Holiday Edition, where intuition meets valuation and everyday life meets market caps. Bill Barker and Matt Argersinger take the stage, vying for the final spot in our 2026 March Market Cap M
The Besties of 2025
t’s the 50th week of the year, which means it’s time once again for the Besties—a celebration of the episodes that educated, amused, and enriched us most in 2025. David highlights ten standout episodes from this year, revisiting the ideas,
Old, New, Borrowed & Blue, Vol. 10
This week, David returns to one of his favorite flexible formats: Old, New, Borrowed, Blue. In this tenth volume, he brings back a few personal lifehacks, peeves, and perks from past episodes; introduces a new financial holiday—“National Sh
Games, Games, Games, Vol. 7
It’s that time of year again—our annual tabletop gift guide returns with Games, Games, Games, Vol. 7. From family-friendly favorites to rich, strategic adventures, David shares five “in case you missed it” classics and then moves through a
November 2025 Mailbag: Be a FOR Person
As November comes to a close and Thanksgiving arrives, our Mailbag is brimming! From Gratitude Challenge triumphs to a brand-new five-stock sampler, from Winter Soldier fortitude to navigating concentrated positions, inheritance questions,
Extra: Funding the Future with Gooding
David is joined by George Khalaf, executive director of the Fool Community Foundation, for a special Weekend Extra featuring Gooding — musician, storyteller, and founder of Funding the Future. Together they explore Gooding’s mission to reac
Gratitude: 2025
As the final months of 2025 ebb away, it is time once again to pause, reflect, and openly acknowledge the gratitude we feel. From great companies that make great stocks possible, to the unifiers who build bridges instead of walls, to the qu
10 Years Later: 5 Lesser Known Rule Breakers
We’re back with the second episode of a new series—10 Years Later—where we blast through time to peek in on a 5-Stock Sampler from 10 years in the past, then zoom back to the present to see what really happened. On the marquee today are 5 L
Great Quotes, Vol. 21: The Primary Pull is the Vision
In this 21st installment of one of our longest-running series, David shares five insightful quotes—really more like passages this time—particularly aimed at business and entrepreneurs. Whether it’s making your vision manifest, providing gen
October 2025 Mailbag: Add Up, Don’t Double Down
From Diwali’s lights in India to a “spiffy-drop” on Netflix, this Mailbag travels widely and thinks deeply. A listener celebrates the Rule Breaker habit of lighting candles, not fanning flames, while others ask how to “Add Up, Don’t Double
Financial Horror Stories Vol. 4, Grave Financial Robbing
By the pricking of my thumbs, something SPOOKY this way comes. That icy chill in the air tells us that it’s that season again. It’s that time of year when Robert Brokamp brings his ghoulishly chilling tales of frightful scams, legal guillot
Stock Stories, Vol. 11: Silicon, Supply Chains & Spicy Wings
Every stock tells a story. This week we gather around the campfire for five fresh tales—from silicon driving the AI era to supply-chain software that keeps retail humming, from a Latin American marketplace that became a fintech/logistics fl
9 Foolish Truths I Hold to Be Self-Evident: 2025
Today is that day—once every two years—when this podcast goes back to basics and we restate and recommit to the eternal verities David sees in business, in investing, and in Rule Breaker Investing. So put down those oars, join us aboard our
Blast from the Past, Vol. 11: Character
David slips on his Fred Roger’s cardigan to revisit five valuable lessons, intertwined with the theme of “how to win in life.” Pulled from classic episodes spanning the last decade of weekly podcasts, David spotlights lessons that light can
September 2025 Mailbag: The House That Netflix Built
It’s a Mailbag of gratitude as the reviews are rolling in for David’s new book. A listener invests $100 for each of his daughters’ birthdays, positioning them for success in their financial futures, as another listener follows David’s advic
Market Cap Game Show: Planes, Steaks & Automobiles
Welcome back to our quarterly Market Cap Game Show! Two past champions—Andy Cross and Yasser El-Shimy—take the stage to test their market-cap mettle (and yours) across ten public companies, vying for a spot in the 2026 March Market Cap Madn
