August 2025 Mailbag: Sports Bettor Turned Investor

A 5-minute listen from Chapter 3 of the Rule Breaker Investing audiobook, out September 16. In “After Yesterday,” David tells the CNBC story of a co-host stunned that he still liked cloud stocks—after yesterday—and why Rule Breaker investors don’t let yesterday’s tape write tomorrow’s script. Enjoy the excerpt, then share it with a friend who could use a smarter, happier, richer mindset. Pre-order Rule Breaker Investing (hardcover, e-book, audiobook) wherever you buy books. Host: David Gardner Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

All year long we’ve opened each episode with a “Page Breaker Preview” sneak peek from David’s forthcoming book. Today, we’ve stitched those 35 snippets into a single, chronological highlight reel—a mini-audiobook that traces the arc of Rule Breaker Investing: from first principles and habits, through stock-picking traits and portfolio rules, to the capstone ideas that tie it all together. With light context, lots of personality, and a lively tempo, this week’s one-of-a-kind episode plays like a curated mixtape of the book’s big ideas. It’s out next week! Pre-order Rule Breaker Investing: https://www.amazon.com/gp/product/1804091219/ Reactions or favorite excerpts? Write us: [email protected] Host: David Gardner Producer: Dan Boyd Companies mentioned: ADBE, AMZN, AXON, CMG, CRM, ISRG, META, NFLX, NVDA, SBUX, SHOP, TSLA Learn more about your ad choices. Visit megaphone.fm/adchoices

We’re launching a new series—10 Years Later—where we open a time capsule, revisit a 5-Stock Sampler on its 10th birthday, and see what really happened. First up is our original (9/2/2015) sampler, 5 Stocks for the Next 5 Years: a motley mix that spanned Latin American e-commerce, rural convenience, blockbuster gaming, frontline cybersecurity, and kitchen-tech roll-ups. Longtime Fool Rick Munarriz joins as David’s sidekick to share the what, why, and when of these stocks’ march through the decade. How did each of these stocks do? How about the sampler’s overall outperformance? David & Rick extract the key lessons. Rule Breaker Investing isn’t just about keeping score; it’s about learning how (and why) we win. Companies Discussed: ATVI, CASY, GOOG (legacy of FEYE/MNDT), MELI, MIDD Sign up for The Motley Fool’s Breakfast News here: www.fool.com/breakfastnews Pre-order David’s upcoming Rule Breaker Investing book here: https://www.amazon.com/gp/product/1804091219/ Host: David GardnerGuest: Rick MunarrizProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

For summer’s final Mailbag, a listener shares how he dropped sports betting and picked up investing, while another wants to know how to allocate portfolios as a Rule Breaker. David brings back Motley Fool Chief Investment Officer, Andy Cross, to discuss tools for tracking your portfolio against the S&P 500, thinking briefly about dividend allocation, then answering the question, “If you were investing your first $1,000 today, what would your approach be?” Those gems, along with Author in August Sam Horn—like a river—running through it! Sign up for The Motley Fool’s Breakfast News here:www.fool.com/breakfastnews Pre-order David’s upcoming Rule Breaker Investing book here: https://www.amazon.com/gp/product/1804091219/ Host: David GardnerGuest: Andy CrossProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

To close out the 2025 Authors in August series, we flip the script—and the mic. Chris Hill, longtime Fool and creator of Motley Fool Money (and host of Money Unplugged) returns as guest host to grill David about his forthcoming book, “Rule Breaker Investing.” David reveals his first-ever Rule Breaker stock (before he’d even coined the phrase), the inspiration for his discipline… he names names on current dark clouds investors may be able to see through, and brings Rule Breaker thinking across diverse topics, from portfolio construction to sports betting. Finally, it’s Chris who leads a round of Buy, Sell, or Hold, with David! Companies Discussed: AAPL, AMZN, AXON, CMG, CRM, DDD, GPRO, ISRG, META, MRNA, MSFT, NFLX, NVDA, ODFL, PTON, SHOP, TREX, TSLA Pre-order Rule Breaker Investing here: https://www.amazon.com/gp/product/1804091219/ Sign up for The Motley Fool’s Breakfast News here: www.fool.com/breakfastnews Guest Host (first one ever): Chris Hill Guest: David Gardner Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Continuing our eighth annual Authors in August series, David welcomes Sam Horn, renowned communications strategist and founder and CEO of the Intrigue Agency, based in Austin, Texas. Sam gamely plays a little book roulette. She starts by detailing how to nail a sixty-second pitch, then walks us through how to handle rude people, blamers, shamers, complainers, non-stop talkers, people who refuse to cooperate, and those who ignore rules or boundaries. They also reveal the word that David is trying his best to avoid saying, and finish with a raucous round of Buy, Sell, or Hold. Sign up for The Motley Fool’s Breakfast Newshere: www.fool.com/breakfastnews Pre-order David’s upcoming Rule Breaker Investing bookhere: https://www.amazon.com/gp/product/1804091219/ Host: David Gardner Guest: Sam Horn Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

In this inaugural episode of our eighth annual Authors in August series, David welcomes back bestselling author, Harvard professor, and Atlantic columnist Arthur Brooks. Arthur brings along counterintuitive ideas about happiness as a habit, the difference between joy and happiness, public vs. anonymous philanthropy, and how the pursuit of money can sometimes… reduce freedom?! David and Arthur also dive into what makes feedback actually helpful, and finish with a spirited round of Buy, Sell, or Hold: Happiness Edition. Sign up for The Motley Fool’s Breakfast Newshere: www.fool.com/breakfastnews Pre-order David’s upcoming Rule Breaker Investing bookhere: https://www.amazon.com/gp/product/1804091219/ Host: David Gardner Guest: Arthur Brooks Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Grab the popcorn—this Mailbag goes well beyond beach talk. A listener uses Rule Breaker tactics, keeps adding as the stock climbs, and lands their first spiffy-pop. David retells the term’s origin and brings back analyst Yasser El-Shimy, whose original pick sparks a rocket-themed chat. Another listener feeds Keats’s “On First Looking into Chapman’s Homer” to AI for a Rule-Breaker remix full of wild surmise. Those nuggets—plus the new Authors in August lineup—power this week’s breezy, idea-packed summer episode. Companies mentioned: RKLB, SBUX Sign up for The Motley Fool’s Breakfast Newshere: www.fool.com/breakfastnews Pre-order David’s upcoming Rule Breaker Investing bookhere: https://www.amazon.com/gp/product/1804091219/ Host: David Gardner Guest: Yasser El-Shimy Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Fresh off of his mixed doubles title at Wimbledon, Sem Verbeek sits back down with David (three years later) to share his journey from professional tennis player, facing a career crossroads, to becoming a Wimbledon champion. He compares the similarities in mindset between tennis and financial strategies, and even turns the tables by becoming the interviewer, asking David some thought-provokingquestions of his own. Sem Verbeek, a man of many talents, on and off the court. Host: David Gardner Guest: Sem Verbeek Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

As summer in the Northern Hemisphere kicks into second gear, David unveils the second volume in this episodic series. He explores the four types of capital, speaks to the importance of embracing good ol’ “R”eality, brings back an honest-to-goodness pet peeve, and unravels a spool of cool words that rhyme with “Fool.”Grab your lemonade, find a comfy spot in the shade, and join us under the summer sun! Companies Discussed: AMZN, NVDA Host: David Gardner Producer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices