Rule Breaker Investing

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!

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Pre-order David’s upcoming Rule Breaker Investing book here: https://www.amazon.com/gp/product/1804091219/



Host: David GardnerGuest: Andy CrossProducer: Bart Shannon
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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/



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www.fool.com/breakfastnews



Guest Host (first one ever): Chris Hill

Guest: David Gardner

Producer: Bart Shannon
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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






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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
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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
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