September Mailbag: Different, But The Same

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

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   Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

From Diwali’s lights in India to a “spiffy-drop” on Netflix, this Mailbag travels widely and thinks deeply. A listener celebrates the Rule Breaker habit of lighting candles, not fanning flames, while others ask how to “Add Up, Don’t Double Down” in practice, what makes a business cyclical, and how to think about price momentum. Plus, a 67-year-old Fool goes all-in, a Boilermaker misses Investor Island, and a Brit reminds us that some “periods of time” are best left to translation. 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: AMZN, CRWD, MELI, META, NFLX, NVDA, RKLB, SHOP, TOST Host: David Gardner Producer: Dan Boyd Learn more about your ad choices. Visit megaphone.fm/adchoices

By the pricking of my thumbs, something SPOOKY this way comes. That icy chill in the air tells us that it’s that season again. It’s that time of year when Robert Brokamp brings his ghoulishly chilling tales of frightful scams, legal guillotines, and savings depleting poltergeists. But, along with every tale of fright, comes a lesson and a warning, to help you beware these dark and malevolent pitfalls. Let the tales begin! (5:35) -  The Chimera of Omaha(12:15) - The Vanguard Vanishing(16:55) - Helter Shelter(23:35) - Invasion of the Crypto Snatchers!(31:00) - I Know What You Signed Last Century(39:22) - The Nightmare on Margaritaville Street 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: Robert BrokampProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Every stock tells a story. This week we gather around the campfire for five fresh tales—from silicon driving the AI era to supply-chain software that keeps retail humming, from a Latin American marketplace that became a fintech/logistics flywheel to a spicy franchiser scaling flavor by the bucket… and a legendary spiffy-pop that still makes us smile. Expect lessons in patience, optionality, moats—and why a single day can sometimes pay back an entire cost basis. Companies Discussed: AMD, AQNT, MANH, MELI, WING, 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 Guests: Sanmeet Deo, Asit Sharma, David Meier, Andy Cross Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Today is that day—once every two years—when this podcast goes back to basics and we restate and recommit to the eternal verities David sees in business, in investing, and in Rule Breaker Investing. So put down those oars, join us aboard our sailboat, and let the winds guide you back toward these valuable core beliefs. Whether you’re well steeped in Foolishness or at the beginning stages of your investing journey, these are nine foundational truths not to be forgotten. Stocks Mentioned: AMZN, GOOG, HUBS, ISRG, MELI, MRNA, NFLX, PFE, SBUX 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

David slips on his Fred Roger’s cardigan to revisit five valuable lessons, intertwined with the theme of “how to win in life.” Pulled from classic episodes spanning the last decade of weekly podcasts, David spotlights lessons that light candles—at a time when too many are busy fanning flames. The five growth-minded blasts from the past: Roy Spence on being a “For” Person “Do you have a ________ friend?” Accept responsibility; blame no one Judge yourself by your results, and others by their intentions Sam Horn’s “proactive grace” An oh-so-timely Blast from the Past—equal parts warmth and backbone—here to help you lead with character, win with kindness, and keep the light on for others. Fool on! 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 Learn more about your ad choices. Visit megaphone.fm/adchoices