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

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

Host: David Gardner
Guests: Emily Flippen, Loren Horst
Producer: Bart Shannon

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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 Gardner
Contestants: Bill Barker, Emily Flippen
Producer: Bart Shannon

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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 Gardner
Contestants: Andy Cross, Loren Horst
Producer: Bart Shannon

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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 Gardner
Producer: Bart Shannon

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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 Gardner
Producer: Bart Shannon

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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, PLNT
Host: David Gardner
Guest: Rick Munarriz
Producer: Bart Shannon

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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 Gardner
Guest: Kevin Kelly
Producer: Bart Shannon

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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 Gardner
Producer: Bart Shannon

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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 Gardner
Guests: Alicia Alfiere, Yasser El-Shimy
Producer: Bart Shannon

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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 Gardner
Guests: Nilima Bhat, Raj Sisodia
Producer: Bart Shannon

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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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