Once a year, around David’s birthday, listeners send in notes sharing what they’ve learned from this podcast over the years—about investing, business, and life. This year’s volume includes reflections on “dips wait for dips,” learning to appreciate mistakes instead of fearing them, the surprising power of simply doing nothing during market volatility, and why optimism itself may be one of the great competitive advantages in life. Along the way: a physician assistant on the front lines of COVID, ...
May 13, 2026•44 min
What happens when you actually do the thing most investors only talk about… and hold stocks for a full decade? This week, David welcomes The Motley Fool’s Tim Beyers and together they go back exactly 10 years— to the week —to revisit five companies picked in May 2016, scoring how they really did and, more importantly, asking why. From biotech to big data to media to real estate, this episode is about both the scoreboard and the lessons only time can teach. If you’ve ever wondered what a true 10-...
May 06, 2026•56 min
From buying in thirds instead of waiting for dips, to a dishwasher hack that still requires the humans to remember the hack, to one listener’s beautifully rebalanced “harbor-and-horizon” portfolio, this month’s mailbag is as motley as ever. Along the way, David cleans up a long-used reference to Heisenberg vs. Hawthorne, hears how Magical Athlete has become a family hit, and considers a pair of listener suggestions that may permanently improve the Market Cap Game Show. Companies Mentioned: ADBE,...
Apr 29, 2026•40 min
What happens when you bring together three storytellers, three themes, and a podcast devoted to making you smarter, happier, and richer? You get Three Fools, our continuing episodic series! This time ’round, David is joined by superstar guests Bill Burke and Mahan Tavakoli as they each share three stories—one to educate, one to amuse, and one to enrich. From investing lessons that last a lifetime to laugh-out-loud anecdotes and heartwarming life insights, these nine stories are packed with inspi...
Apr 22, 2026•56 min
Some financial terms sound scarier than they are. Others sound familiar… right up until you realize you don’t actually know what they mean. This week, David returns with Volume 8 of Gotta Know the Lingo , welcoming Fool analysts Alicia Alfiere, Amanda Kish, and Nick Sciple to help translate the language of investing for the rest of us. Some terms are simpler, some more advanced, all of them useful—and if you’ve ever nodded along to financial jargon hoping nobody would ask a follow-up, this episo...
Apr 15, 2026•48 min
Can you quickly decide which AI companies deserve your attention—and which to skip? What do you believe that most people don’t? And is there a simple trick, learnable in one afternoon, that can delight kids (and maybe yourself) for a lifetime? This week, David returns with Volume 11 of one of our OG episodic series: Mental Tips, Tricks & Lifehacks . He shares seven small ideas that punch above their weight: from a clever $10 household fix, to a mindset shift borrowed from Kevin Kelly, to dia...
Apr 08, 2026•44 min
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 powerful idea runs underneath: What you do, repeatedly, becomes who you are. Along the way: A single line that might rewire how you think about your own habits (and your portfolio) A Silicon Valley inversion that flips investing on its head Shakespeare, serenely...
Apr 01, 2026•36 min
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?), revisit a thoughtful challenge from Professor Jason Corso on whether Rule Breaker Investing is built on habits, recipes, or something closer to an algorithm, pick up a clever Google News hack that lets you see the world through another country’s headlines, and ...
Mar 25, 2026•36 min
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 Madness World Championship . As always, you’re not just watching—you’re playing along. Ten companies. Ten chances to test your market cap intuition. Range it… and decide: in or out? From elevators to hotel loyalty programs to the strange ways we all think about “bl...
Mar 18, 2026•1 hr 10 min
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 round. It is a rematch of the epic Final Four game they played this very week one year ago. As always, the real game is for you: ten companies, ten market-cap ranges, and one simple question each round: Inside or outside? Play along and keep score as you liste...
Mar 11, 2026•1 hr 13 min
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 our first semifinal matchup, with a spot in the World Championship at stake. Grab a pencil, set your ranges, and see whether your market-cap intuition can outscore Andy, Loren… or both. The Madness is on, and the bracket is tightening. Companies mentioned: ACN,...
Mar 04, 2026•1 hr
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 reflex of “Right?” that may or may not actually validate anything. Along the way, we touch on Evernote in an AI world, foreign exchange risk from a Fool down under, and the eternal market phenomenon of buying the day before the drop. It’s playful, pointed, and a...
Feb 25, 2026•47 min
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, Pay Later,” the suspicious preface “If I’m being honest…,” and the curious cultural surrender embedded in “In my day…“. Along the way, there’s a certain Halloween-sized marketing sham, a conversational tic that may deserve early retirement, and a high-decibel...
Feb 18, 2026•28 min
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 after a much better, truer timeframe for the Rule Breaker Investor: 10 years. To the very day. Which stocks did David get really right? Which ones really wrong? And why? As always, in this third installment of our new episodic series, it’s not about cherry-pic...
Feb 11, 2026•43 min
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 slo...
Feb 04, 2026•1 hr 4 min
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...
Jan 28, 2026•38 min
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, ...
Jan 21, 2026•1 hr 24 min
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 th...
Jan 14, 2026•52 min
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 winner...
Jan 07, 2026•53 min
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 exc...
Dec 31, 2025•54 min
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 delightfu...
Dec 24, 2025•1 hr 10 min
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...
Dec 17, 2025•1 hr 25 min
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...
Dec 10, 2025•46 min
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, gif...
Dec 03, 2025•1 hr 3 min
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 celebrati...
Nov 26, 2025•1 hr 18 min
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 c...
Nov 22, 2025•48 min
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 ...
Nov 19, 2025•39 min
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 B...
Nov 12, 2025•56 min
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 New...
Nov 05, 2025•40 min
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 Th...
Oct 29, 2025•55 min
