September 2026 Mailbag: 16 Years Old to 25 Years Foolish

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 GardnerGuests: Yasser El-Shimy, Mac GreerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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 megaphone.fm/adchoices

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 Yourself (The Jacksons) * Faith (George Michael) * Follow that Dream (Elvis Presley) * Go Your Own Way (Fleetwood Mac) Watching investments compound and grow: * Chain Reaction (Diana Ross) * Celebration (Kool and the Gang) * Hitch a Ride (Boston) * More Today than Yesterday (Spiral Staircase) For spiffy pops: * Breakout (Swing Out Sister) * Feels So Good (Chuck Mangione) * Can’t Help Falling in Love (Elvis Presley) * Do It Again (Steely Dan) * Glad All Over (Dave Clark Five) * Happy (The Carpenters) Paying capital gains tax: * Don’t Fear the Reaper (Blue Öyster Cult) When a stock doubles: * Double Lovin’ (The Osmonds) Selling stocks: * Breaking Up is Hard to Do (Neil Sedaka) Inevitable market downturns: * Don’t Go Breaking My Heart (Elton John and Kiki Dee) * Don’t Worry, Baby (The Beach Boys) * Hold On (Wilson Phillips) * I’m Still Standing (Elton John) * It’s All Right (Gerry and the Pacemakers) * It’s Gonna Be Okay (Piano Guys and Cliff Richard) * Let’s Hang On (The Four Seasons) When deciding to buy a new stock: * How Will I Know? (Whitney Houston) Investing in thirds: * Just a Little Bit (Robbie Nevil) Before you figure out your sleep number: * (Last Night) I Didn't Get to Sleep at All (The Fifth Dimension) * If You Can’t Sleep (She & Him) Putting all your money in only one stock: * Brink of Disaster (Lesley Gore) Investing for the long-term: * Carry On (Crosby, Stills, Nash, and Young) Retiring after a successful investing career: * Cake by the Ocean (DNCE) * Fun, Fun, Fun (The Beach Boys) RBI’s optimistic attitude: Life is Good (Ringo Starr) This episode was sponsored by Coveron. One scam can cost you everything. Protect yourself now. The first 100 users get 20% off with code rule20 at coveron.com/rule20 Learn more about your ad choices. Visit megaphone.fm/adchoices

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

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

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 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