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 But this year, the ghosts of celebrity misfortunes have been replaced by something even more frightening: financial horrors that may be lurking in YOUR own life.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 lesso...

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 penaltie...

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 thi...

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 compan...

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, c...

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...

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,...

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—i...

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...

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 widel...

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...

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...

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...

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 bigges...

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 wha...

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...