Rule Breaker Investing

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



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



Host: David GardnerGuests: Andy Cross, Robert BrokampProducer: Bart Shannon
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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
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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 drives us, and what reminds us why we invest. Let’s feel grateful together.



Companies mentioned: AAPL, CMG, CRM, SHOP



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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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 Bylund, joins David on this trip through time to share the what, why, and when of these stocks’ march through the decade. Did we beat the market?



Companies Discussed: MIDD, MSTR, N (Acquired by Oracle- ORCL), NUVA (Acquired by Globus Medical - GMED), TREX

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: Anders Bylund

Producer: Bart Shannon
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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 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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