Rule Breaker Investing

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 shares ways of noticing long arcs, understanding why certain platforms and ideas compound, and staying optimistic without getting swept up in hype. From AI working alongside other AIs to the power of patience and perspective, this episode is an invitation to slow down just enough to see what really matters as change unfolds. Sign up for The Motley Fool’s Breakfast News here: ⁠⁠www.fool.com/breakfastnews⁠⁠ Order David’s Rule Breaker Investing book here: ⁠⁠https://www.amazon.com/gp/product/1804091219/⁠⁠ Host: David GardnerGuest: Kevin KellyProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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, score-kept game for kids (including outperforming Dad), consider a mischievous strategy for the Market Cap Game Show, and close with an inspiring note from a retired basketball coach whose patient, optimistic approach built lasting financial freedom. Along the way, we’re reminded that investing isn’t just about returns—it’s about judgment, temperament, family, and choosing to be a “for” person over time. Sign up for The Motley Fool’s Breakfast News here: ⁠www.fool.com/breakfastnews⁠ Order David’s Rule Breaker Investing book here: ⁠https://www.amazon.com/gp/product/1804091219/⁠ Companies mentioned: HOOD, MELI, NFLX, TTD Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 framework he’s used for more than a decade to replace vague labels like “medium risk” with something concrete and measurable. Using Etsy and Duolingo as live 2026 case studies, the trio scores each company question by question—covering the business, financials, competition, leadership, and the investor’s own willingness to dig deeper. Along the way, listeners get a deeper look at how studying risk is really about studying quality—and how seeing risk clearly with a number is just another way Rule Breaker investors can learn to break the rules…. Companies mentioned: DUOL, ETSY Host: David GardnerGuests: Alicia Alfiere, Yasser El-ShimyProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 healing as a “soft” idea, Raj and Nilima walk through the book’s seven steps and explore how inner state shapes judgment, patience, courage, and long-term thinking—in business, investing, and life. Along the way, they connect the “Wise Fool” archetype and the idea of Shakti to conscious capitalism, rule-breaking optimism, and the kind of leadership that compounds over time. Host: David GardnerGuests: Nilima Bhat, Raj SisodiaProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 GardnerGuests: Bill Barker, Matt ArgersingerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Sign up for The Motley Fool’s Breakfast News here: ⁠www.fool.com/breakfastnews⁠ Order David's Rule Breaker Investing book here: ⁠https://www.amazon.com/gp/product/1804091219/ Host: David GardnerGuests: Andy Cross, Chris Hill, Emily Flippen, Morgan Housel, Randi Zuckerberg, Rick Engdahl, Sam Horn, Sem Verbeek, Shirzad ChamineProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Sign up for The Motley Fool’s Breakfast News here: www.fool.com/breakfastnews Order David's Rule Breaker Investing book here: https://www.amazon.com/gp/product/1804091219/ Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 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 Sign up for The Motley Fool’s Breakfast News here: www.fool.com/breakfastnews Order David’s Rule Breaker Investing book here: https://www.amazon.com/gp/product/1804091219/ Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Sign up for The Motley Fool’s Breakfast News here: ⁠⁠⁠www.fool.com/breakfastnews⁠⁠⁠ Order David's Rule Breaker Investing book here: ⁠⁠⁠https://www.amazon.com/gp/product/1804091219/⁠⁠ Host: David GardnerGuests: Andy Cross, Robert BrokampProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Sign up for The Motley Fool’s Breakfast News here: ⁠⁠www.fool.com/breakfastnews⁠⁠ Order David's Rule Breaker Investing book here: ⁠⁠https://www.amazon.com/gp/product/1804091219/⁠⁠ Host: George Khalaf, David GardnerGuest: GoodingProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Sign up for The Motley Fool’s Breakfast News here: www.fool.com/breakfastnews Order David's Rule Breaker Investing book here: https://www.amazon.com/gp/product/1804091219/   Host: David Gardner Producer: Bart Shannon   Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Sign up for The Motley Fool’s Breakfast News here: ⁠www.fool.com/breakfastnews⁠ Order David's Rule Breaker Investing book here: ⁠https://www.amazon.com/gp/product/1804091219/⁠ Host: David Gardner Guest: Anders Bylund Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 genuine help for free, or choosing the better story when faced with a decision, this episode offers food for thought on visualizing your goals, deepening your customer relationships, and leading a more interesting life. Sign up for The Motley Fool’s Breakfast News here:⁠⁠⁠www.fool.com/breakfastnews⁠⁠⁠ Order David’s Rule Breaker Investing book here:⁠⁠⁠ https://www.amazon.com/gp/product/1804091219/⁠⁠⁠ Host: David Gardner Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Down” in practice, what makes a business cyclical, and how to think about price momentum. Plus, a 67-year-old Fool goes all-in, a Boilermaker misses Investor Island, and a Brit reminds us that some “periods of time” are best left to translation. Sign up for The Motley Fool’s Breakfast News here: www.fool.com/breakfastnews Order David’s Rule Breaker Investing book here: https://www.amazon.com/gp/product/1804091219/ Companies mentioned: AMZN, CRWD, MELI, META, NFLX, NVDA, RKLB, SHOP, TOST Host: David Gardner Producer: Dan Boyd Learn more about your ad choices. Visit megaphone.fm/adchoices

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 guillotines, and savings depleting poltergeists. But, along with every tale of fright, comes a lesson and a warning, to help you beware these dark and malevolent pitfalls. Let the tales begin! (5:35) -  The Chimera of Omaha(12:15) - The Vanguard Vanishing(16:55) - Helter Shelter(23:35) - Invasion of the Crypto Snatchers!(31:00) - I Know What You Signed Last Century(39:22) - The Nightmare on Margaritaville Street Sign up for The Motley Fool’s Breakfast News here: ⁠⁠www.fool.com/breakfastnews⁠⁠ Order David’s Rule Breaker Investing book here: ⁠⁠https://www.amazon.com/gp/product/1804091219/⁠ Host: David GardnerGuest: Robert BrokampProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 flywheel to a spicy franchiser scaling flavor by the bucket… and a legendary spiffy-pop that still makes us smile. Expect lessons in patience, optionality, moats—and why a single day can sometimes pay back an entire cost basis. Companies Discussed: AMD, AQNT, MANH, MELI, WING, Sign up for The Motley Fool’s Breakfast News here:⁠⁠www.fool.com/breakfastnews⁠⁠ Order David’s Rule Breaker Investing book here:⁠⁠ https://www.amazon.com/gp/product/1804091219/⁠⁠ Host: David Gardner Guests: Sanmeet Deo, Asit Sharma, David Meier, Andy Cross Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 sailboat, and let the winds guide you back toward these valuable core beliefs. Whether you’re well steeped in Foolishness or at the beginning stages of your investing journey, these are nine foundational truths not to be forgotten. Stocks Mentioned: AMZN, GOOG, HUBS, ISRG, MELI, MRNA, NFLX, PFE, SBUX Sign up for The Motley Fool’s Breakfast News here:⁠www.fool.com/breakfastnews⁠ Order David’s Rule Breaker Investing book here:⁠ https://www.amazon.com/gp/product/1804091219/⁠ Host: David Gardner Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 candles—at a time when too many are busy fanning flames. The five growth-minded blasts from the past: Roy Spence on being a “For” Person “Do you have a ________ friend?” Accept responsibility; blame no one Judge yourself by your results, and others by their intentions Sam Horn’s “proactive grace” An oh-so-timely Blast from the Past—equal parts warmth and backbone—here to help you lead with character, win with kindness, and keep the light on for others. Fool on! Sign up for The Motley Fool’s Breakfast News here:⁠www.fool.com/breakfastnews⁠ Order David’s Rule Breaker Investing book here:⁠ https://www.amazon.com/gp/product/1804091219/⁠ Host: David Gardner Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices