Rule Breaker Investing

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 episode is for you. As always, there’s a scoring system, a little Foolish fun, and a few concepts that may stick with you longer than the ticker tape.Host: David GardnerGuests: Alicia Alfiere, Amanda Kish, Nick ScipleProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 dialing down big ambitions into “little bets” that actually get done. Oh, and some recent boardgame picks! Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 out-investing most of Wall Street Why Warren Buffett shouldn’t have bought Amazon—and why that’s good news And a modern upgrade to “question everything” for the age we’re actually living in Companies mentioned: AMZN, CMG, ISRG, MELI, NFLX, NVDA, SHOP, TSLAHost: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 yes… return to Pet Peeves territory with a “Bamm!” vs. “Boom!” breakdown of locker room acoustics. Along the way, we touch on how we think, how we learn, and how we behave—in markets and in life.And we close with one Fool’s simple question: Does the Snap Test apply… beyond stocks? 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: AXON, DIS Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 “blood,” this one takes a few delightfully unexpected turns along the way. Throwdowns raise the stakes, instincts get tested, and you’re right there in it the whole time. Keep your own score, trust your gut, and see how you stack up. Companies mentioned: DGX, H, LYV, MAR, OTIS, PLTR, SBUX, SNOW, TRMB, TXN 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: Emily Flippen, Loren HorstProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 listen—and see if your intuition can meet or beat our two veteran Foolish analysts. Companies mentioned: ABNB, ACM, ADYEY, GRAB, MIELY, MSCI, PAYC, SKYT, TDG, WIX Host: David GardnerContestants: Bill Barker, Emily FlippenProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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, AMD, BA, CSU, GLOB, IDXX, INTU, SERV, TCEHY, WIX 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 GardnerContestants: Andy Cross, Loren HorstProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 reminder that words shape how we think… and how we invest. 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 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 train experience you may never un-hear again.Part humor, part language audit, part cultural critique—Pet Peeves returns to remind us that words matter, incentives matter, and yes… it is still your day. 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

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-picking highlights—it’s about accountability and perspective. It’s about what a 10-year scorecard teaches that the financial media’s shorter windows simply can’t.And the results of this sampler—along with the full program of all 30 5-stock samplers—once again prove the eye-popping success and durable wins that come to Rule Breaker investors. 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: CRI, ELLI, IPGP, MELI, PLNTHost: David GardnerGuest: Rick MunarrizProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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