Rule Breaker Investing

Latest Episodes:

Essays From Yesterday, Vol. 8 Jan 07, 2026

Show notes

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, forgotten drawdowns, early buyouts, language that shapes behavior, and the enduring power of mindset. Along the way, we’re reminded that sharp declines happen more often than we remember, that short-term scorecards mislead, and that a handful of great winners can overwhelm many mistakes. This lesson-filled episode makes the case for capital “H” History as an investor’s secret weapon—and for why perspective, patience, and precise thinking continue year after year to crush the stock market averages.

• (5:02) Introduction to July 2006 Issue
• (15:55) The Tim Beyers Issue
• (27:42) Greatest Issue Ever
• (37:26) Starter Stocks

Companies mentioned: AKAM, APKT, CRM, GOOG, ISRG, MELI, NILE, PDLI, QLIK

Host: David Gardner
Producer: Bart Shannon

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December 2025 Mailbag: “Am I a Fool?” Dec 31, 2025

Show notes

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. We hear from a father investing alongside his seven-year-old son, an investor who audited his own selling history and discovered just how early he’d stepped off some great rides, and Fools thinking carefully about contribution timing, position sizing, and excellence that keeps winning. Along the way, David revisits core ideas like letting winners run, being a “for” person, and ultimately answers the question that brings the year full circle: How do you know—really know—Am I a Fool?

Companies mentioned: CRWD, NFLX, RKLB, SPOT, TSLA

Host: David Gardner
Producer: Bart Shannon

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Market Cap Game Show: Bubble Wrap & Sidewalk Robots Dec 24, 2025

Show notes

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 Madness World Championships, as they test their mettle—and yours—across ten public companies. From Bubble Wrap and sidewalk robots to semiconductors, ski resorts, biotech pipelines, and online commerce platforms, the matchups span the familiar and the delightfully unexpected, with plenty of raucous banter along the way. Play along at home, challenge your market-cap intuition, and see whether you can outscore Bill, Matt… or both.

Companies mentioned: ANET, DAVA, DFH, INCY, MTN, QCOM, SEE, SERV, SHOP, TSLA

Host: David Gardner
Guests: Bill Barker, Matt Argersinger
Producer: Bart Shannon

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The Besties of 2025 Dec 17, 2025

Show notes

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, stories, and lessons that lingered long after the microphones were off. And all of the voices behind those moments return for brief cameos, reflecting on the year that was and looking ahead to what comes next. From Authors in August and a Market Cap Game Show world championship, to character, community, games, and the many ways listeners took concrete steps toward financial freedom, this episode captures the breadth of what Rule Breaker Investing aims to be: thoughtful, optimistic, playful, and practical. A year in review — not ranked, just remembered.

Companies mentioned: VKTX

Order David's Rule Breaker Investing book here: ⁠https://www.amazon.com/gp/product/1804091219/

Host: David Gardner
Guests: Andy Cross, Chris Hill, Emily Flippen, Morgan Housel, Randi Zuckerberg, Rick Engdahl, Sam Horn, Sem Verbeek, Shirzad Chamine
Producer: Bart Shannon

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Old, New, Borrowed & Blue, Vol. 10 Dec 10, 2025

Show notes

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 Share Day”—imagining a country where every American becomes an owner; borrows a passage from his free downloadable book chapter to explore how AI may (or may not) fit into Rule Breaker investing; and closes with a blue reflection on the rise and fall of Bed Bath & Beyond—and asks, was this the very first stock The Motley Fool ever shorted?

Something old, something new, something borrowed, something blue—only on this week’s Rule Breaker Investing!

Companies mentioned: BBBY

Order David's Rule Breaker Investing book here: https://www.amazon.com/gp/product/1804091219/

Host: David Gardner
Producer: Bart Shannon

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Games, Games, Games, Vol. 7 Dec 03, 2025

Show notes

It’s that time of year again—our annual tabletop gift guide returns withGames, 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 curated list of 12 games, arranged from lightest to heaviest. Expect quick, joyful picks like Wavelength and Dorfromantik, followed by deeper journeys into titles such as Dune Imperium: Uprising and SETI. There’s something here for every level of gamer, gift-giver, and holiday gathering.Whether you’re choosing a reliable crowd-pleaser or hunting for a challenge for your most seasoned gaming friends, this seventh edition of David’s holiday games guide is here to spark joy around the table. Fool on… and Game on!

Companies Mentioned: AMZN

Order David’s Rule Breaker Investing book here: https://www.amazon.com/gp/product/1804091219/

Host: David Gardner
Producer: Bart Shannon

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November 2025 Mailbag: Be a FOR Person Nov 26, 2025

Show notes

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, regrets, and remarkable investing wins—this month’s notes run deep and wide. David is joined by Andy Cross and Robert Brokamp to explore strategies for retirement withdrawals, building children’s portfolios, and managing dominant holdings, while also celebrating generosity, unity, and candle-lighting stories from across the Fool community. It’s a warm, thoughtful Mailbag to close the month—and a reminder of why this community is such a joy to read and host each year.

Companies mentioned: AAPL, AMZN, CHWY, COST, DIS, DUOL, HOOD, NFLX, NVDA, PLTR, RDDT, SHOP, SNOW, TSLA

Order David's Rule Breaker Investing book here: ⁠⁠⁠https://www.amazon.com/gp/product/1804091219/⁠⁠

Host: David Gardner
Guests: Andy Cross, Robert Brokamp
Producer: Bart Shannon

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Extra: Funding the Future with Gooding Nov 22, 2025

Show notes

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 reach young people across America with dynamic, music-driven performances that make financial literacy not just understandable, but unforgettable. From inspiring students to pursue their dreams to equipping them with practical tools for money and investing, this conversation highlights the power of creativity, purpose, and education to change lives.

Order David's Rule Breaker Investing book here: ⁠⁠https://www.amazon.com/gp/product/1804091219/⁠⁠

Host: George Khalaf, David Gardner
Guest: Gooding
Producer: Bart Shannon

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Gratitude: 2025 Nov 19, 2025

Show notes

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 quiet power of candles and the people who share their flame — this episode celebrates them all. David even offers five simple ways you can build a bridge in your own life this week. This week’s podcast is an expression of thankfulness for what inspires us, what drives us, and what reminds us why we invest. Let’s feel grateful together.

Companies mentioned: AAPL, CMG, CRM, SHOP

Order David's Rule Breaker Investing book here: https://www.amazon.com/gp/product/1804091219/

Host: David Gardner

Producer: Bart Shannon

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10 Years Later: 5 Lesser Known Rule Breakers Nov 12, 2025

Show notes

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 Lesser Known Rule Breakers (from 11/11/2015)that feature a company providing commercial kitchen solutions, a few big name changes, a couple of even bigger acquisitions, and a wood alternative decking company. Longtime contributing writer at the Fool, Anders Bylund, joins David on this trip through time to share the what, why, and when of these stocks’ march through the decade. Did we beat the market?

Companies Discussed: MIDD, MSTR, N (Acquired by Oracle- ORCL), NUVA (Acquired by Globus Medical - GMED), TREX

Order David's Rule Breaker Investing book here: ⁠https://www.amazon.com/gp/product/1804091219/⁠

Host: David Gardner

Guest: Anders Bylund

Producer: Bart Shannon

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