Rule Breaker Investing

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 But this year, the ghosts of celebrity misfortunes have been replaced by something even more frightening: financial horrors that may be lurking in YOUR own life.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 GardnerGuest: Robert BrokampProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 GardnerGuest: Kimball CrossleyProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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, SBUXHost: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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…

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 GardnerProducer: Bart Shannon Learn more about your ad choices. Visit…

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 GardnerGuest: Rick MunarrizProducer: Bart ShannonCompanies Mentioned: AAPL, CNI, DIS, ECL, GOOG Learn more about your ad choices. Visit megaphone.fm/adchoices

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 GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

After three weeks of Authors in August, the authors step aside and Rule Breaker listeners take the conversation somewhere new. A middle-school teacher wrestles with what happens when the measurements meant to improve education begin defining it instead. A father investing for his daughters wonders whether “Add Up, Don’t Double Down” applies to index funds. There are Rule Breaker songs, Spiffy Pops shared between old friends, and, near episode end, the Fool who originated Pet Perks returns with an audio reminder that some of life’s most valuable moments can be hiding inside the everyday hassles we’re tempted to hurry through. Host: David GardnerProducer: Bart Shannon Ken's full playlist: For failing to become an active financial investor: * Cast Your Fate to the Wind (George Winston) For letting your winners run high: * Along for the Ride (Mates of State) * All Time High (Rita Coolidge) For brand new investors: * Any Dream Will Do (Donny Osmond) * Come and Get It (Badfinger) * Don’t Be Afraid (Boston) * Enjoy…

Why do we work? A paycheck matters, of course. And, when so much of life is spent working, might we reasonably hope for something more?Closing out the ninth year of Authors in August, David welcomes Dave Ulrich, one of the world’s leading thinkers on organizations, leadership, and human capability. Using the longtime favorite The Why of Work as a jumping-off point, their conversation ranges widely across what gives work meaning, what great leaders understand about people, and what decades spent studying organizations have taught Dave about the ways we work—and why! As technology transforms the workplace and old assumptions keep getting rewritten, some decidedly human questions endure. What makes work worth doing? What brings out the best in people? And how might we create workplaces that leave employees, customers, and the world better off? Host: David GardnerGuest: Dave UlrichProducer: Bart ShannonCompanies Mentioned: ADBE, JWN, WMT Thank you to our sponsor: Coveron: One scam can cost you everything.…

Artificial intelligence may feel suddenly everywhere, but AI pioneer Vasant Dhar has had a front-row seat for more than four decades—teaching AI, building companies around it, and bringing machine learning to Wall Street long before ChatGPT entered the conversation. For the second week of Authors in August, David sits down with Dhar to ask not merely what machines can do, but how humans can think with them. When should we trust AI? When does it sharpen our thinking—and when does it make our brains lazy? If intelligence itself is becoming a commodity, where will tomorrow’s value be created? And in a future where machines become extraordinarily capable, what are humans for?A conversation about AI, investing, trust, judgment, and our increasingly intelligent future. The Damodaran Bot is available for public use at: damodaranbot.com Vasant's monthly newsletter can be found at: vasantdhar.substack.com Host: David GardnerGuest: Vasant DharProducer: Bart Shannon Thank you to our sponsor: Coveron: One scam can cost…

Authors in August is back! It’s our 9th year featuring authors of books that David loves and thinks you’ll love too. So for the third time, philosopher and game scholar Thi Nguyen joins back with Rule Breaker Investing—and this time the conversation reaches far beyond games. What happens when the scores we invent to measure success begin quietly reshaping what we value? Together, in an incredibly wide-ranging discussion, David and Thi explore rankings, metrics, investing, institutions, artificial intelligence, and the subtle difference between playing a game… and letting the game play you. And we close with a rousing round, as ever, of Buy, Sell, or Hold? Whose scorecard are you living by? Host: David GardnerGuest: Thi NguyenProducer: Bart Shannon Thank you to our sponsors: Coveron: One scam can cost you everything. Protect yourself now. The first 100 users get 20% off with code rule20 at https://coveron.com/rule20. Learn more about your ad choices. Visit megaphone.fm/adchoices

As Rule Breaker Investing enters its twelfth year, it is fitting to hand the microphone back to the people who have helped shape it from the very beginning: our listeners.This month’s Mailbag spans investing, artificial intelligence, financial freedom, World Cup soccer, custodial Roth IRAs, Rule Breaker stock selection… and even a soundtrack for Foolish living?! Along the way are a heartbreaking story, practical questions, imaginative ideas, and reminders that the best investing community doesn’t simply exchange stock tips—we help all of us become smarter, happier, richer. And perhaps a little wiser, too.Host: David GardnerProducer: Bart Shannon Companies Mentioned: AMZN, AXON, ISRG, MELI, NVDA, PLTR, RKLB, SERV, SHOP, TEM Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s become something of a midsummer tradition on Rule Breaker Investing: set aside the markets for a week and simply follow curiosity wherever it leads.This year’s sampler wanders through technology, sports, business, demographics, literature, and a few unexpected places in between. Along the way are thoughts about how to get the most out of AI, a few tweaks that could improve the world’s biggest sporting event, a prediction about who may be becoming the world’s most valuable people, and a dramatic reading of one of David’s favorite short stories.Two pages.Idle thoughts for you, of a summer’s day.Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

In the anxious days following Brexit, rather than predict the future, David asked a different question: Where are the opportunities? The result was a five-stock sampler built not on politics, but on optimism.Now a full decade has passed. Joined by longtime Fool Karl Thiel, we crack open the time capsule, revisit the original investment theses, score all five stocks against the market, and ask what a ten-year scorecard can teach that three years never could. Some ideas exceeded expectations. Others humbled us. All of them remind us why Rule Breakers look beyond the headlines and invest for the long haul. Host: David GardnerGuest: Karl ThielProducer: Bart ShannonCompanies Mentioned: GOOGL, EEFT, HAIN, BKNG, TSLA Learn more about your ad choices. Visit megaphone.fm/adchoices

Every so often, five quotations come along that don’t merely make you nod. They make you stop, put the book down, and think.This week we explore why the best investors first become students of themselves, why our minds work better when they’re surrounded by rich ideas, why business is one of humanity’s great engines for creating value, why prosperity may make societies not just wealthier but wiser, and why one vision of America argues that a nation’s greatest competitive advantage isn’t its geography or its resources—it’s its ability to continually renew itself.Five quotations. Five conversations. And perhaps one or two ideas that will quietly change the way you see investing, business, and life. Happy 250th to the US of A!Host: David GardnerProducer: Bart ShannonCompanies Mentioned: AMZN, MCD, NVDA Learn more about your ad choices. Visit megaphone.fm/adchoices

Each Independence Week, Rule Breaker Investing asks a simple question: What have you done over the past year to create financial freedom—for yourself or for others? This year’s answers feature a listener’s Declaration of Financial Independence and a young woman whose very first stock purchase turned out to be… Nvidia. Along the way, we revisit three favorite moments from the first three years of this annual tradition, discovering that the path toward financial freedom may be simpler than it first appears: Believe. Persist. Pass it on. Happy Independence Week—and may financial freedom continue to echo like a Liberty Bell.Host: David GardnerProducer: Bart ShannonCompanies Mentioned: NVDA, SCHW Learn more about your ad choices. Visit megaphone.fm/adchoices

This month’s Mailbag ranges from Washington, D.C. to Germany, from the SEC to the moon, and from individual stock ownership to the deeper question of what freedom is actually for. Along the way, fellow Fools write in about transparency, curiosity, market caps, parenting, AI, adding to winning investments, and what can happen when decades of patient investing quietly compound into opportunities to help others. As always, the best part of the Mailbag is you.Host: David GardnerProducer: Bart ShannonCompanies Mentioned: HAS, ISRG, JEPI, KO, MAT, MSCI, NKE, NVDA Learn more about your ad choices. Visit megaphone.fm/adchoices

The Market Cap Game Show returns for its 42nd installment, with longtime Motley Fool personalities Charly Travers and Jason Moser battling for a coveted spot in next March’s Market Cap Madness Final Four.But this episode marks something new. For the first time, players can invoke the King-Sharon Rule, adding an extra layer of strategy, risk, and reward to the game. Agree or disagree is no longer the only choice. Feeling confident? Call “higher” or “lower” and put an extra half-point on the line.Ten stocks. Two seasoned competitors. One brand-new rule. And for reasons that only became apparent while recording, an unusually heavy concentration of food, cars, food delivered by car, food consumed after getting out of a car, car parts, collector cars, and at least one company that makes spices for the food. Host: David GardnerProducer: Bart Shannon Companies Mentioned: DASH, GPC, HGTY, MKC, MTN, OC, RACE, SYY, TDG, TEAM Learn more about your ad choices. Visit megaphone.fm/adchoices

For the twelfth time, we gather around the campfire for one of RBI’s favorite traditions: Stock Stories. Five Fools. Five investing lessons. This summer’s tales share a surprising common thread: A biotech shell company that refused to die. An old gift of IBM stock quietly compounding for decades. A Fool who finally bought Alphabet nearly twenty years after he first meant to. A company called Life360 proving that “obvious” doesn’t mean “fully valued.” And a producer awakening to stock-market investing in his 50s.The lesson? You may think you missed it. You probably didn’t.Pull up a chair, grab a marshmallow, and join us around the campfire. Host: David GardnerProducer: Bart Shannon Companies Mentioned: GOOGL, IBM, LIF, UBER (and some random CUSIP#!) Learn more about your ad choices. Visit megaphone.fm/adchoices

Why do some organizations seem unable to solve the very problems they were created to fix? Why do seemingly rational people end up chasing the wrong goals? And why does one innocent purchase so often lead to five more? In this new volume of RBI’s recurring cerebral series, David explores a handful of memorable laws and principles that help explain how people, businesses, markets, and institutions actually behave… from the sublime to the silly. Some are famous. One is his own. All are useful. Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

What happens when Nvidia’s annual dividend suddenly exceeds David’s original Motley Fool cost basis—six times over? This month’s Mailbag brings back a Foolish old term, “divvy-pop,” while also revisiting the power of doing less, holding more, and letting great companies keep surprising you.Also inside: a Buffett-meets-Rule-Breaker reflection from British Columbia, a jellybean contest gone mathematically sideways, a GameStop question that runs straight into the Snap Test, and a closing shout-out to Mr. Ernst’s personal finance class at Kopachuck Middle School in Gig Harbor, Washington—where the next generation is already learning that investing means ownership. Companies Mentioned: AAPL, AMZN, ANET, BIDU, BN, BRK.A, BRK.B, CHWY, EBAY, ⁠FFH.TO⁠, GME, GOOG, ISRG, MELI, META, NFLX, NVDA, SHOP, TMFC, TSLAHost: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

To mark his 60th birthday, David delivers what may be the most distilled episode in Rule Breaker Investing history: 20 thoughts about investing, 20 about business, and 20 about life—gathered from decades of entrepreneurship, stock-picking, reading, losing, winning, and trying to stay Foolish along the way. From the “Ship of Fools” and the spiffy-pop, to optionality, fads that weren’t fads, the hardest thing in life, divergence and convergence, and why the longer Frank Lloyd Wright lived, the more beautiful life became… this is a fast-moving collection of convictions, stories, quotes, and life-earned observations designed to stick with you long after the episode ends.A milestone birthday. A landmark episode. [And yes: somehow, he fit 60 thoughts within 60 minutes.] Host: David GardnerProducer: Bart Shannon Companies Mentioned: ABNB, AMZN, CROX, GOOG, LUV, NFLX, SBUX, TSLA Learn more about your ad choices. Visit megaphone.fm/adchoices

Once a year, around David’s birthday, listeners send in notes sharing what they’ve learned from this podcast over the years—about investing, business, and life. This year’s volume includes reflections on “dips wait for dips,” learning to appreciate mistakes instead of fearing them, the surprising power of simply doing nothing during market volatility, and why optimism itself may be one of the great competitive advantages in life.Along the way: a physician assistant on the front lines of COVID, a renowned cancer surgeon who juggles, a Foolish Leprechaun who finally stopped trading and started investing, and a Scotsman reminding us all to look for L’Optimisme in the world.Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

What happens when you actually do the thing most investors only talk about… and hold stocks for a full decade? This week, David welcomes The Motley Fool’s Tim Beyers and together they go back exactly 10 years—to the week—to revisit five companies picked in May 2016, scoring how they really did and, more importantly, asking why. From biotech to big data to media to real estate, this episode is about both the scoreboard and the lessons only time can teach. If you’ve ever wondered what a true 10-year mindset looks like—voilà. Host: David GardnerGuest: Tim BeyersProducer: Kristi Waterworth Companies Mentioned: CELG, DIS, MNDY, SPLK, TWTR, Z Learn more about your ad choices. Visit megaphone.fm/adchoices

From buying in thirds instead of waiting for dips, to a dishwasher hack that still requires the humans to remember the hack, to one listener’s beautifully rebalanced “harbor-and-horizon” portfolio, this month’s mailbag is as motley as ever. Along the way, David cleans up a long-used reference to Heisenberg vs. Hawthorne, hears how Magical Athlete has become a family hit, and considers a pair of listener suggestions that may permanently improve the Market Cap Game Show. Companies Mentioned: ADBE, DUOL, HUBS, INTU, ISRG, MELI, NBIS, NVDA, RKLB, TSMHost: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

What happens when you bring together three storytellers, three themes, and a podcast devoted to making you smarter, happier, and richer? You get Three Fools, our continuing episodic series! This time ’round, David is joined by superstar guests Bill Burke and Mahan Tavakoli as they each share three stories—one to educate, one to amuse, and one to enrich. From investing lessons that last a lifetime to laugh-out-loud anecdotes and heartwarming life insights, these nine stories are packed with inspiration and practical takeaways.Host: David GardnerGuests: Bill Burke, Mahan TavakoliProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Some financial terms sound scarier than they are. Others sound familiar… right up until you realize you don’t actually know what they mean.This week, David returns with Volume 8 of Gotta Know the Lingo, welcoming Fool analysts Alicia Alfiere, Amanda Kish, and Nick Sciple to help translate the language of investing for the rest of us. Some terms are simpler, some more advanced, all of them useful—and if you’ve ever nodded along to financial jargon hoping nobody would ask a follow-up, this episode is for you. As always, there’s a scoring system, a little Foolish fun, and a few concepts that may stick with you longer than the ticker tape.Host: David GardnerGuests: Alicia Alfiere, Amanda Kish, Nick ScipleProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Can you quickly decide which AI companies deserve your attention—and which to skip? What do you believe that most people don’t? And is there a simple trick, learnable in one afternoon, that can delight kids (and maybe yourself) for a lifetime? This week, David returns with Volume 11 of one of our OG episodic series: Mental Tips, Tricks & Lifehacks. He shares seven small ideas that punch above their weight: from a clever $10 household fix, to a mindset shift borrowed from Kevin Kelly, to dialing down big ambitions into “little bets” that actually get done. Oh, and some recent boardgame picks! Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Some truths are too good to say only once. This week, David re-blasts five timelessly powerful ideas from the past—about identity, investing, serenity, frameworks, and questioning—and brings them together in a fresh 2026 mix. One quietly powerful idea runs underneath: What you do, repeatedly, becomes who you are.Along the way: A single line that might rewire how you think about your own habits (and your portfolio) A Silicon Valley inversion that flips investing on its head Shakespeare, serenely out-investing most of Wall Street Why Warren Buffett shouldn’t have bought Amazon—and why that’s good news And a modern upgrade to “question everything” for the age we’re actually living in Companies mentioned: AMZN, CMG, ISRG, MELI, NFLX, NVDA, SHOP, TSLAHost: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

March Madness may be over, but the Mailbag is just beginning—and as always, you’re the star of the show. This month we hear from listeners who tracked the data on our Market Cap Game Show strategies (does “always disagree”… really work?), revisit a thoughtful challenge from Professor Jason Corso on whether Rule Breaker Investing is built on habits, recipes, or something closer to an algorithm, pick up a clever Google News hack that lets you see the world through another country’s headlines, and yes… return to Pet Peeves territory with a “Bamm!” vs. “Boom!” breakdown of locker room acoustics. Along the way, we touch on how we think, how we learn, and how we behave—in markets and in life.And we close with one Fool’s simple question: Does the Snap Test apply… beyond stocks? 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: AXON, DIS Host: David…

The bracket is complete. The stakes are highest. And now… it’s time to crown a champion.This week on Rule Breaker Investing, defending champion Emily Flippen faces off against Cinderella challenger Loren Horst in the March Market Cap Madness World Championship. As always, you’re not just watching—you’re playing along. Ten companies. Ten chances to test your market cap intuition. Range it… and decide: in or out?From elevators to hotel loyalty programs to the strange ways we all think about “blood,” this one takes a few delightfully unexpected turns along the way. Throwdowns raise the stakes, instincts get tested, and you’re right there in it the whole time. Keep your own score, trust your gut, and see how you stack up. Companies mentioned: DGX, H, LYV, MAR, OTIS, PLTR, SBUX, SNOW, TRMB, TXN 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: Emily…

The Madness continues! This week on Rule Breaker Investing, the second semifinal of March Market Cap Madness tips off as defending world champion Emily Flippen faces long-time Motley Fool advisor Bill Barker for a place in the championship round. It is a rematch of the epic Final Four game they played this very week one year ago. As always, the real game is for you: ten companies, ten market-cap ranges, and one simple question each round: Inside or outside? Play along and keep score as you listen—and see if your intuition can meet or beat our two veteran Foolish analysts. Companies mentioned: ABNB, ACM, ADYEY, GRAB, MIELY, MSCI, PAYC, SKYT, TDG, WIX Host: David GardnerContestants: Bill Barker, Emily FlippenProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

March Market Cap Madness tips off its Final Four this week on Rule Breaker Investing, and you’re not just watching—you’re playing. Past world champion Andy Cross (6–1 lifetime) squares off against Cinderella contender Loren Horst (1–0) in our first semifinal matchup, with a spot in the World Championship at stake. Grab a pencil, set your ranges, and see whether your market-cap intuition can outscore Andy, Loren… or both. The Madness is on, and the bracket is tightening. Companies mentioned: ACN, AMD, BA, CSU, GLOB, IDXX, INTU, SERV, TCEHY, WIX 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 GardnerContestants: Andy Cross, Loren HorstProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

This week’s Mailbag picks up where Pet Peeves left off—and then some. Listeners write in with their own linguistic grievances, from “10 straight unanswered points” to the curious inflation of words like “countless,” to the conversational reflex of “Right?” that may or may not actually validate anything. Along the way, we touch on Evernote in an AI world, foreign exchange risk from a Fool down under, and the eternal market phenomenon of buying the day before the drop. It’s playful, pointed, and a reminder that words shape how we think… and how we invest. 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 GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s been 27 months since this series’s last installment, which means David has had time to quietly bottle up a fresh batch of entirely new irritations—all original, no repeats. This year’s edition takes aim at the slippery phrase “Buy Now, Pay Later,” the suspicious preface “If I’m being honest…,” and the curious cultural surrender embedded in “In my day…“.Along the way, there’s a certain Halloween-sized marketing sham, a conversational tic that may deserve early retirement, and a high-decibel train experience you may never un-hear again.Part humor, part language audit, part cultural critique—Pet Peeves returns to remind us that words matter, incentives matter, and yes… it is still your day. 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 GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Ten years ago this week, in the teeth of a downturn, David picked five stocks under the banner “5 Stocks to Feed the Bear.” This week, he and longtime Fool Rick Munarriz revisit that full basket—not after a month, a quarter, or a year, but after a much better, truer timeframe for the Rule Breaker Investor: 10 years. To the very day.Which stocks did David get really right? Which ones really wrong? And why? As always, in this third installment of our new episodic series, it’s not about cherry-picking highlights—it’s about accountability and perspective. It’s about what a 10-year scorecard teaches that the financial media’s shorter windows simply can’t.And the results of this sampler—along with the full program of all 30 5-stock samplers—once again prove the eye-popping success and durable wins that come to Rule Breaker investors. Sign up for The Motley Fool’s Breakfast News here: ⁠⁠www.fool.com/breakfastnews⁠⁠ Order David’s Rule Breaker Investing book here:…

Kevin Kelly—founding editor of Wired magazine and a lifelong observer of technology in motion—returns to Rule Breaker Investing for a conversation about how the future actually shows up. We don’t trade in predictions here. Instead, Kevin shares ways of noticing long arcs, understanding why certain platforms and ideas compound, and staying optimistic without getting swept up in hype. From AI working alongside other AIs to the power of patience and perspective, this episode is an invitation to slow down just enough to see what really matters as change unfolds. 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: Kevin KellyProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

This week’s Rule Breaker Investing Mailbag brings together beautiful questions and stories to start the new year. We wrestle with a values-alignment dilemma around owning Robinhood, explore what it looks like to turn investing into a real, score-kept game for kids (including outperforming Dad), consider a mischievous strategy for the Market Cap Game Show, and close with an inspiring note from a retired basketball coach whose patient, optimistic approach built lasting financial freedom. Along the way, we’re reminded that investing isn’t just about returns—it’s about judgment, temperament, family, and choosing to be a “for” person over time. 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: HOOD, MELI, NFLX, TTD Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Risk gets talked about a lot in investing—and often defined poorly. This week on Rule Breaker Investing, David is joined by Motley Fool analysts Alicia Alfiere and Yasser El-Shimy to walk through his full 25-point risk rating system, a framework he’s used for more than a decade to replace vague labels like “medium risk” with something concrete and measurable. Using Etsy and Duolingo as live 2026 case studies, the trio scores each company question by question—covering the business, financials, competition, leadership, and the investor’s own willingness to dig deeper. Along the way, listeners get a deeper look at how studying risk is really about studying quality—and how seeing risk clearly with a number is just another way Rule Breaker investors can learn to break the rules…. Companies mentioned: DUOL, ETSY Host: David GardnerGuests: Alicia Alfiere, Yasser El-ShimyProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

This week on Rule Breaker Investing, David is joined by Raj Sisodia and Nilima Bhat, co-authors of Healing Leaders, for a conversation about leadership burnout, meaning, and why wholeness may be a strategic advantage. Rather than treating healing as a “soft” idea, Raj and Nilima walk through the book’s seven steps and explore how inner state shapes judgment, patience, courage, and long-term thinking—in business, investing, and life. Along the way, they connect the “Wise Fool” archetype and the idea of Shakti to conscious capitalism, rule-breaking optimism, and the kind of leadership that compounds over time. Host: David GardnerGuests: Nilima Bhat, Raj SisodiaProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

As we open 2026, David looks backward to get clearer about what really matters going forward. In the eighth installment of Essays From Yesterday, he revisits four Rule Breaker essays written between 2006 and 2014—spanning market sell-offs, forgotten drawdowns, early buyouts, language that shapes behavior, and the enduring power of mindset. Along the way, we’re reminded that sharp declines happen more often than we remember, that short-term scorecards mislead, and that a handful of great winners can overwhelm many mistakes. This lesson-filled episode makes the case for capital “H” History as an investor’s secret weapon—and for why perspective, patience, and precise thinking continue year after year to crush the stock market averages. • (5:02) Introduction to July 2006 Issue • (15:55) The Tim Beyers Issue • (27:42) Greatest Issue Ever • (37:26) Starter Stocks Companies mentioned: AKAM, APKT, CRM, GOOG, ISRG, MELI, NILE, PDLI, QLIK Host: David GardnerProducer: Bart Shannon Learn more about your ad choices.…

It’s the final Rule Breaker Investing podcast of 2025, and the year ends as it always does—with your Mailbag. David shares his annual year-forward market call, then works through listener notes that capture the heart of the Foolish journey. We hear from a father investing alongside his seven-year-old son, an investor who audited his own selling history and discovered just how early he’d stepped off some great rides, and Fools thinking carefully about contribution timing, position sizing, and excellence that keeps winning. Along the way, David revisits core ideas like letting winners run, being a “for” person, and ultimately answers the question that brings the year full circle: How do you know—really know—Am I a Fool? Companies mentioned: CRWD, NFLX, RKLB, SPOT, TSLA Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s time once again for the Market Cap Game Show Holiday Edition, where intuition meets valuation and everyday life meets market caps. Bill Barker and Matt Argersinger take the stage, vying for the final spot in our 2026 March Market Cap Madness World Championships, as they test their mettle—and yours—across ten public companies. From Bubble Wrap and sidewalk robots to semiconductors, ski resorts, biotech pipelines, and online commerce platforms, the matchups span the familiar and the delightfully unexpected, with plenty of raucous banter along the way. Play along at home, challenge your market-cap intuition, and see whether you can outscore Bill, Matt… or both. Companies mentioned: ANET, DAVA, DFH, INCY, MTN, QCOM, SEE, SERV, SHOP, TSLA Host: David GardnerGuests: Bill Barker, Matt ArgersingerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

t’s the 50th week of the year, which means it’s time once again for the Besties—a celebration of the episodes that educated, amused, and enriched us most in 2025. David highlights ten standout episodes from this year, revisiting the ideas, stories, and lessons that lingered long after the microphones were off. And all of the voices behind those moments return for brief cameos, reflecting on the year that was and looking ahead to what comes next. From Authors in August and a Market Cap Game Show world championship, to character, community, games, and the many ways listeners took concrete steps toward financial freedom, this episode captures the breadth of what Rule Breaker Investing aims to be: thoughtful, optimistic, playful, and practical. A year in review — not ranked, just remembered. Companies mentioned: VKTX 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…

This week, David returns to one of his favorite flexible formats: Old, New, Borrowed, Blue. In this tenth volume, he brings back a few personal lifehacks, peeves, and perks from past episodes; introduces a new financial holiday—“National Share Day”—imagining a country where every American becomes an owner; borrows a passage from his free downloadable book chapter to explore how AI may (or may not) fit into Rule Breaker investing; and closes with a blue reflection on the rise and fall of Bed Bath & Beyond—and asks, was this the very first stock The Motley Fool ever shorted? Something old, something new, something borrowed, something blue—only on this week’s Rule Breaker Investing! Companies mentioned: BBBY 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 GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s that time of year again—our annual tabletop gift guide returns with Games, Games, Games, Vol. 7. From family-friendly favorites to rich, strategic adventures, David shares five “in case you missed it” classics and then moves through a curated list of 12 games, arranged from lightest to heaviest. Expect quick, joyful picks like Wavelength and Dorfromantik, followed by deeper journeys into titles such as Dune Imperium: Uprising and SETI. There’s something here for every level of gamer, gift-giver, and holiday gathering.Whether you’re choosing a reliable crowd-pleaser or hunting for a challenge for your most seasoned gaming friends, this seventh edition of David’s holiday games guide is here to spark joy around the table. Fool on… and Game on! Companies Mentioned: AMZN 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 GardnerProducer: Bart Shannon Learn more about your ad…

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…

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