Rule Breaker Investing

The Motley Fool
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Mar 25, 2026 • 36min

March 2026 Mailbag: Habits, Hacks & “Boom”

Listeners probe whether contrarian rules hold up and share hard data from the Market Cap game. A debate about habits, recipes, and algorithmic approaches to investing sparks a larger look at how we learn and decide. A clever Google News trick reveals foreign headlines. And a quirky locker-room sound debate contrasts “Bamm” with “Boom” while pondering shared-space manners.
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Mar 18, 2026 • 1h 10min

2026 March Market Cap Madness Championship: Loren v. Emily

Lauren Hurst, Motley Fool investment analyst and Market Cap Game regular. Emily Flippen, Motley Fool advisor and two-time champion with Survivor fame. They face off in a high-stakes market cap showdown. Ten companies, surprise valuations, tight throwdowns, and playful word games. Expect market cap guesses, disagreements, and championship bragging rights.
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Mar 11, 2026 • 1h 13min

2026 March Market Cap Madness: Emily vs. Bill (BEMILY 2!)

Bill Barker, a longtime Motley Fool analyst and market-cap game veteran, faces Emily Flippen, the reigning Market Cap Game Show champion and former Survivor contestant. They clash over ten companies' market-cap ranges. Tense guesses, surprise reveals, playful banter, and the famous Barker protocol make for lively competition.
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Mar 4, 2026 • 1h

2026 March Market Cap Madness: Andy vs. Loren

Lauren Hurst, Rule Breakers investment analyst and Market Cap Game Show standout. Andy Cross, Motley Fool CIO and past Market Cap champion. They clash in a March Market Cap Madness semifinal. Short rounds cover Globant, Accenture, Boeing, Tencent, Wix, AMD, Intuit, IDEX, Serve Robotics and more. Expect tight ranges, playful banter, and competitive strategy.
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18 snips
Feb 25, 2026 • 47min

February 2026 Mailbag: Countless… Right?

A lively mailbag about language quirks and how word choice nudges thinking. Short takes on overused phrases like "countless" and conversational tags such as "Right?". Tangents cover note apps and Evernote in an AI era. A bit on currency risk for Australian investors and the habit of buying before a market drop.
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8 snips
Feb 18, 2026 • 28min

Pet Peeves, Vol. 9: Buy Now, Pay Later… Right?

Short rants about corporate purpose overstatements and marketing spin. A critique of the phrase “if I’m being honest” and other conversational tics. A warning about Buy Now, Pay Later encouraging overspending. Complaints about tiny “fun-sized” packaging and one-word replies like “right.” A loud Amtrak bin noise and a push to stop nostalgic “in my day” thinking.
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50 snips
Feb 11, 2026 • 43min

10 Years Later: 5 Stocks to Feed the Bear

Rick Munarriz, longtime Motley Fool analyst known for clear company analysis. He revisits a 10-year stock sampler and discusses which picks soared and which stumbled. They examine causes like buyouts, competition, and demographic shifts. Conversation highlights a standout compounder, resilient subscriptions, and lessons about volatility and long-term perspective.
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48 snips
Feb 4, 2026 • 1h 4min

Let’s Talk About the Future in 2026 with Kevin Kelly

Kevin Kelly, founding editor of Wired and longtime tech futurist, guides a patient, long-arc view of technology. He talks about AI as day one and specialized AIs, why robots lag language models, the rising U.S.-China duopoly, and why optimism and practical testing matter. Short takes on transparency, sci-fi probes, and working at unnamed frontiers round out the conversation.
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37 snips
Jan 28, 2026 • 38min

January 2026 Mailbag: Values, Kids, Games & Inspiration

A values-versus-ownership dilemma around Robinhood sparks a conversation about product harm and stewardship. Turning investing into a score-kept game for kids and clever Market Cap Game Show tactics come up. A retired coach’s patient saving and compounding story highlights temperament, optimism, and long-term financial freedom.
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39 snips
Jan 21, 2026 • 1h 24min

Calculating Risk Foolishly, Vol. 4: ETSY v. DUOL

Join Alicia Alfieri, a savvy Motley Fool analyst specializing in consumer and e-commerce, and Yasser El-Shimy, an expert on global partnerships, as they dissect risk in the context of Etsy and Duolingo. They tackle Alicia's concerns about Etsy's vulnerability to larger rivals, while Yasser praises Duolingo's strong market position and brand loyalty. Their scorecard approach reveals not just the companies' financials but also their competitive advantages and potential pitfalls, making for a compelling discussion about investment risk.

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