Rule Breaker Investing

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 wise...

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 t...

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...

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...

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 Life3...

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...

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 mathema...

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 har...

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 grea...

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 abou...

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 li...

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...

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—...

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 thei...

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 (a...

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, pic...

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 dec...

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 r...

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 outsco...

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 unde...

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 Hallowe...

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?...

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 workin...

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 re...

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 c...