Rule Breaker Investing

“Something old, something new, something borrowed, something blue (and a silver sixpence in her shoe)” traditionally refers to what a bride should wear on her wedding day for good luck. No wedding bells here today, but we’re borrowing the old, familiar rhyme to rein in an otherwise disparate collection of Rule Breaking investing thoughts. Spoiler alert: At the end, David will be talking about his beloved – and blue – alma mater. Thanks to Audible for supporting our podcast. Get a free audiobook with a free 30 day trial at audible.com/fool.

Today's mailbag is overstuffed with your excellent contributions! We talk about how to keep cool in the face of big losers, relay a life-hack to make you happy, debut a new investing term, and even leave you with a tune worth whistling. All this and more in the March mailbag!

This week we look at Malcolm Gladwell’s 2009 New Yorker article, “How David Beats Goliath” and extract three inspiring investing lessons. Gladwell spells out the hidden advantages of being the “underdog” in a way well-suited to our Rule Breaker investing style. Thanks to Audible for supporting our podcast. Listen to Audible's new original series: Ponzi Supernova. Details at audible.com/ponzi. Audible and Amazon Prime members listen free.

Often the best way to improve our investing is to improve our thinking. And to improve our thinking, it’s often helpful to reach outside of the disciplines of investing and business. Today we delve into the teachings of education reformer, Deborah Meier, and the “5 Habits of Mind” that she believes should be taught to all 21st Century students. Perhaps these habits should be taught to 21st Century investors as well!

From the earliest days of The Motley Fool, our mission has been to "Educate, Amuse & Enrich." Today we double-down on the "Educate" with an exploration of some commonly used financial terms. Guest analysts Andrew Fredrickson, Abi Malin, Aaron Bush, and Jim Mueller join David to define and discuss net profit margin, cash flow vs. net income, dividend yield, burn rate, and spiffy-pop!

Today we present a third installment of tips, tricks and lifehacks—to help you be a better you. Find a hidden superpower in your Kindle app, improve your investing while learning to draw, achieve your goals by ignoring them, and much more! Do you have a favorite mental tip or trick? Share it with us on Twitter @RBIPodcast.

February may be a short month, but our mailbag is as full as ever, overflowing with great questions and comments from you, our dear listener. Today we tackle why our biggest losers are the stocks we never buy, why predicting the future is getting more difficult, and much more. Plus, David reveals some of his favorite books to inspire and improve your investing.

In a world of “fake news” and “alternative facts,” the political climate seems ever more chaotic and unpredictable. But as investors, by definition, we take a long-term view. And we look to businesses and innovators, not politicians, to bring us into the future. Today, David picks 5 companies that are likely to help us through these troubled times -- and become ever more valuable for doing so.

This time last year, David picked “5 Stocks to Feed the Bear,” highlighting 5 smaller companies with low risk ratings. Though these were meant as long-term picks (3 years at least), today we’re checking in to see how they’re doing so far. Spoiler alert: we’re kind of hoping you bought a few shares!

After last year's Portrait of the Investor as a Young Man, David goes even further back, seeking insights and investing lessons from his early youth. So gather back around the campfire for a few stories and lessons from these formative years. We look back to days of school projects, theater companies, baseball characters and mishaps abroad. Through it all, we learn that as we stumble through this human experiment, character counts, and optimism is justified.

There are plenty of riches in this month's mailbag, including your thoughts on David's biggest losers, how to score your "Golden Ticket" to FoolFest, and how David switches hats when choosing stocks for Rule Breakers or Stock Advisor. Plus, a lightning round of your picks for "Don't Make Me Think" stocks.

In March of 2008, David had just read a wonderful book on information architecture and website design by Steve Krug, entitled. "Don't Make Me Think." Turning lessons learned about design towards his home turf of investing, this inspired David to publish an essay titled, "Great Stocks Don't Make You Think!" Today we revisit that essay, the lessons learned at the time, and reflect on what we've learned in the years that have passed since. 

Last year around this time we released a two-part podcast entitled David's Biggest Losers. Let's make that a tradition here and talk about another half-dozen stocks that have performed poorly over the past 3 years. We don't like to dwell on failure—and indeed can learn a lot more by studying our wins—but it's good to eat some humble pie once in a while and remember that we don't have to win them all to win the game.

Happy New Year! In 2017, as always, we predict that the market will go up. But these great quotes will help you face the coming market, regardless of what it does. And if our prediction is wrong, we'll just "wait for a warm day and shoot off the next one!"

In this final mailbag of 2016 we answer your questions about picking stocks when the market is at all-time highs, what to do when "buy what you know" steers you wrong, how to navigate a short squeeze, and more. Plus, a little flattery from one of our favorite CEOs! This week’s podcast is brought to you by Foolanthropy: Learn more at give.fool.com.

Our newly founded Holiday Tradition here at Rule Breaker Investing is a re-reading of David’s 2010 essay entitled Why We Invest. But first, as special a gift to us all, a brief and illuminating cameo with the living investing legend, Jack Bogle. Jack gives us his recipe for great investing success, his thoughts on investing in our current political climate, the importance of character over success, and much more. It’s a perfect holiday blend of investing wisdom!

December is a month of gratitude here at Rule Breaker Investing. With that in mind, we’re spending today’s episode talking about and, more importantly, listening to Jack Bogle. As the creator of the Index Fund, the founder of Vanguard, and an all-around stand-up guy who has dedicated his life’s work to helping people invest better, you might say that Jack is the ultimate Rule Breaker. Certainly his accomplishments are worth singing about. So indeed, we will!

As the holidays approach, you may be looking for an extra special present for the children in your life. For the gift that truly keeps on giving, today’s show brings you five kid-friendly stocks that are good to hold for the next five years or longer. And never to pass up a teaching moment, David also shares some advice on how to talk about each of the companies those lucky kids will now own. Spoiler alert: The stock you’re probably most expecting is not on the list!

Guy Kawasaki is currently the Chief Evangelist of Canva, an online tool with the mantra of democratizing graphic design. But his resume goes much deeper. From his early days at Apple to his venture capital firm to his bestselling books, Guy has a long history of helping startups succeed. In this RBI Extra episode, we break down some conventional wisdom with Guy's 10 Commandments of Entrepreneurship.

Uh oh, it's both mailbag day and the close of November's Entrepreneur Month. How can we possibly do both? I guess it's time for another RBI Extra episode! Today we answer your questions on investing in the Great Recession, Stock Advisor vs. Rule Breakers, and games for the holidays, and we also address concerns over David's diction. Then, on Saturday watch your feed for a special episode with tech evangelist, Guy Kawasaki.