Rule Breaker Investing

The house always wins.

David Gardner takes a hard look at America’s booming sports-betting industry, revisiting the math behind the wagers and offering betting listeners a wonderful alternative: investing.

And who else stands to win even when the bettors lose? Superstar athletes and Hollywood celebrities… some of the world’s most admired figures are helping sell gambling to their fans. David has a few questions for them—and for all of us—about the money we make, the influence we wield, and the legacy we leave behind.

Host: David Gardner
Producer: Bart Shannon

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What does it really mean to get 60% of your stock picks right? Can a lifetime of successful investing create a financial problem you never expected? And how do you find your way forward when you’re not quite sure where you’re going?

Eight correspondents bring us questions spanning investing, sports, money, and life. Along the way, we revisit some recent Rule Breaker conversations, challenge a few assumptions, and ultimately find ourselves at the edge of a dark forest, with a lighthouse in the distance. Sometimes the next step is all you need to see.

Host: David Gardner
Guest: George Khalaf
Producer: Bart Shannon

Disclosure: Advertisements are sponsored content and provided for informational purposes only. The Motley Fool and its affiliates (collectively, “TMF”) do not endorse, recommend, or verify the accuracy or completeness of the statements made within advertisements. TMF is not involved in the offer, sale, or solicitation of any securities advertised herein and makes no representations regarding the suitability, or risks associated with any investment opportunity presented. Investors should conduct their own due diligence and consult with legal, tax, and financial advisors before making any investment decisions. TMF assumes no responsibility for any losses or damages arising from this advertisement.

We’re committed to transparency: All personal opinions in advertisements from Fools are their own. The product advertised in this episode was loaned to TMF and was returned after a test period or the product advertised in this episode was purchased by TMF. Advertiser has paid for the sponsorship of this episode.

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The witching hour approaches! For the fifth consecutive Halloween, Motley Fool retirement expert Robert Brokamp returns to haunt Rule Breaker Investing with tales of financial terror. But this year, the ghosts of celebrity misfortunes have been replaced by something even more frightening: financial horrors that may be lurking in YOUR own life.

Seven financial frights. A haunted house full of lessons. From retirement accounts with skeletons in their closets to terrifying tax traps and dangers hiding in plain sight, David and Bro venture into the financial haunted house—and share a few tricks for escaping with your wealth, and your wits, intact. Enter if you dare!

Host: David Gardner
Guest: Robert Brokamp
Producer: Bart Shannon

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It’s football season! America’s most popular sport is in full swing, at both the NFL professional level and, of course, the college professional level. And what better time to ask whether the game we love could be even better?

Longtime sports journalist, coach, and baseball scout Kimball Crossley returns with a provocative proposition: Does football’s punishment always fit the crime? From penalties that can change a game to rules that reward behavior they ought to discourage, Kimball and David take a fresh look at America’s favorite sport. Along the way, they explore what makes a game fairer, smarter, and more entertaining—with a detour into fantasy football and a closing round of Buy/Sell/Hold.

Host: David Gardner
Guest: Kimball Crossley
Producer: Bart Shannon

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A Pet Perk doesn’t need to be profound; it's the noticing that makes it profound. This time around, we leave investing and business behind for seven small pleasures and practices drawn entirely from life.
What can a surprisingly good armchair teach us about spending? How might getting “upstream” today make tomorrow better? Seven reminders to notice, appreciate, and occasionally act on the good things hiding in plain sight—ending with one worth saying while we still can.
Companies Mentioned: CAVA

Host: David Gardner
Producer: Bart Shannon

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This month, eight correspondents bring us questions and stories from very different points along the Foolish journey. We talk time freedom, indexing in a faster-changing world, investing “miracles,” the rewards of choosing stocks even when the scoreboard disagrees—and the challenge of knowing when patience has simply become waiting.
Plus, a little career advice, a one-man podcast production company named Bart, and a final letter 25 years in the making.
Companies Mentioned: AMZN, HOG, JMIA, LFMD, NFLX, NVDA, PLUG, SBUX
Host: David Gardner
Producer: Bart Shannon

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Price per share is only half the story. Multiply it by shares outstanding and you get the number that matters: market capitalization, the market’s current price tag on a public company. And for the 43rd time, it’s time to turn that lesson into a game.

David welcomes Motley Fool analyst Yasser El-Shimy and longtime Fool producer and personality Mac Greer for ten companies spanning cloud software, credit cards, Norwegian energy, sleep apnea, community banking, rare-earth minerals, biotech real estate, and 78,000 miles of pipelines. Along the way: two Throwdowns, the King-Sharon rule, some company-history surprises—and a coveted future seat in the March Market Cap Madness Final Four hanging in the balance.

As always, the most important contestant is you. Agree or disagree with the stated ranges, risk the extra half-point by calling higher or lower when you dare, keep your own score—and see whether you can beat the Fools.

Companies Mentioned: ARE, AXP, EQNR, INSP, JKHY, KMI, LOB, MP, WDAY, ZM

Host: David Gardner
Guests: Yasser El-Shimy, Mac Greer
Producer: Bart Shannon

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ChatGPT is back on the mound, David is back in the batter’s box, and for the first time in more than a year it’s time for five fresh pitches.
This time, the questions aren’t quizzes—they’re provocations. What advantages did David have as an investor at 30 that he no longer has at 60—and what has he gained in return? Which Rule Breaker principle might prove less durable over the decades ahead? What could the future price of a single company tell us about the future of the world? And when two very different kinds of Rule Breakers compete for one spot in your portfolio, which way do you swing?

Five questions designed to challenge assumptions, expose blind spots, summon a few strange hypotheticals, and perhaps produce an answer or two David himself didn’t know he had.
ChatGPT asks. David answers. Five questions, five swings. Play ball!

Companies Mentioned: AAPL, AMZN, GOOG, ISRG, NFLX, NVDA, PLTR, RKLB, SPCX, SPY, TSLA

Host: David Gardner
Producer: Bart Shannon

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en years ago, amid plenty of bearish sentiment, David did something unique in the history of his 5-Stock Samplers: he picked five stocks specifically to beat the market over just the next year. The common denominator? Each ranked among the lowest-risk companies in his investing universe.
A decade later, Rick Munarriz joins him to fire up the time machine. Apple, Canadian National Railway, Disney, Ecolab, and Alphabet go back on the scoreboard—not merely for the one-year contest they were chosen to play, but for the nine bonus years that followed. Which delivered? Which disappointed? And what does a decade teach us about what “low risk” really means?
Five companies. One unusually short original time horizon. Ten years of actual results—and another chance to ask what we got right, what we got wrong, and what we can learn for the decade ahead.
Host: David Gardner
Guest: Rick Munarriz
Producer: Bart Shannon
Companies Mentioned: AAPL, CNI, DIS, ECL, GOOG

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Every once in a while, Rule Breaker Investing sets aside the theme and embraces the hodgepodge. Something Old, something New, something Borrowed, something Blue—four directions, no particular reason they should fit together, and that’s part of the fun.

This time, a World Series champion offers a lesson about sample sizes and staying with a winning process. An old investing truth finds a new home—in exactly 350 words. Kevin Kelly makes the case for becoming the most improbable version of yourself in an increasingly predictable, AI-powered world. And then, because Blue means whatever Blue wants to mean: blueberries! Genuinely blue, surprisingly interesting, and even capable of teaching an investor a thing or two about… compounding.
Baseball, bear markets, improbable lives, and blueberries. Fool on!

Host: David Gardner
Producer: Bart Shannon

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