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 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