Rule Breaker Investing

Today we go back to the bottomless well of great quotations. Whether touching on culture, games, brand, or indeed investing, we like to keep this podcast Motley! These 5 quotes (plus a few) will leave you with new thoughts and new perspectives to take with you on your Foolish journey.

Today David picks up the long, skinny, game show microphone to play host in our first ever Market Cap Game! Contestant and special guest, Matt Argersinger will compete against you, dear listener. Your prize for winning will be bragging rights and free use of the #IBeatMatt hashtag on Twitter!

 Make your organization’s corporate culture more engaging, rewarding, happier, more productive… more Foolish! David welcomes back return guests Kara Chambers and Lee Burbage.

What is Amazon-safe? Is there an Amazon killer? Why does the market go up over time? And hey, did I just hear NFLX pop a hundred-bagger? The end of the month brings us to the RBI mailbag episode, where David gives his irreverent take on these questions and more.

This week David offers a new take on the term “story stocks.” He and a few of his fellow Fools share some of their favorite stock stories. Some will make you laugh, some cry, and all are Motley.

It’s been just over a year since Britain decided to leave the European Union and David made five Brexit-inspired stock picks. While those were meant as long-term picks (3 years at least), it’s fun to check on their progress. The FTSE 100 (or Footsie) is up since then. How we doin’?

David interviews McKenna Haase, a 20-year-old student, race car driver, entrepreneur, and Rule Breaking investor. They discuss how she started racing, what it is like to be one of the only females in her sport, and how she balances racing, school, and her two companies. Plus McKenna shares some of her favorite stock picks and investing heroes.

It's the end of June and you've outdone yourselves again! Our mailbag is full and we've got a packed show. Today David tackles how to build a new portfolio from scratch, considers whether to sell or add to losers, and attempts to solve an ancient, riddle that left Plato pondering. All that and more on this week's mailbag. Thanks to Harry's for supporting The Motley Fool. Get your Free Trial — go to Harrys.com/fool

Let's face it, the stock market has been a raging bull for a long time now. It can't go on forever, right? It might even crash, and hard! So, what's a Rule Breaker to do? Pick 5 stocks that are hitting all-time highs, of course! Because great companies are worth owning. Because today's highs will be tomorrow's memories. And, well, because that's just the way we roll.

By now you have heard the news of the shooting at a Congressional baseball practice here in Alexandria, just a few blocks from us here at Fool HQ. In response, David urges us to maintain independent thinking, civility, a motley influence, and the humility that is the core of Foolishness.

Are you concerned by the “market drop” we experienced over the last few days? If you’re a Rule Breaking Investor, chances are it hit you pretty hard, and that can be painful. But if you’re a Rule Breaking Investor, chances are you’re also going to be holding some of the best companies for a decade or more, and that is sure to cheer you up. As David has said before, and will say again, “Stocks always go down faster than they go up, but they always go up more than they go down.”

You may not yet be familiar with Zack Kanter, but the self-described entrepreneur, speaker, futurist, writer, amateur chef, and all-around nerd is someone you should get to know if you’re curious about the future. Today Zack is here to talk with David about why Ford and Geico should fear the autonomous car, how an entrepreneur like you could improve the news, and Amazon’s path to becoming the world’s most valuable company. Sponsored link: www.casper.com/fool, code: fool

It is the last day of the month, which means, as always, it’s mailbag time! Today David looks at the Great Man Theory vs. the Cultural View of investing, whether to invest a little bit at a time or in big lump sums, and why the market’s P/E ratio shouldn’t guide your investing decisions. Plus, another misattributed quote and quite possibly a dirty joke! Get $25 off your first purchase at bombfell.com/fool

The sun is settling in, the pool is almost open, grills are heating up... That’s right: ‘tis the season for graduation speeches! Any day now, successful alumni will be returning to their alma maters to dole out optimism and advice to bright-eyed, graduating seniors. One such speech from back in 1995 is worth revisiting, and today David does just that with special guest, Guy Kawasaki. Join us as we look ahead from the past in this, our 100th episode! Thanks to Harry’s for supporting The Motley Fool. Get your Free Trial Set – go to Harrys.com/fool.

When Warren Buffet was asked on CNBC why he still isn’t buying Amazon – a company he greatly admires – he quipped, “Stupidity.” But why should the greatest investor of our time regret sitting out on a single company that sits outside the framework of his self-ascribed circle of competence? Buffett doesn’t need to be a Rule Breaker. That’s for you and me, fellow Fools! Thanks to Slack for supporting Motley Fool Answers. Learn more at slack.com.

Nick Epley is a social psychologist and the author of "Mindwise: Why We Misunderstand What Others Think, Believe, Feel, and Want." Today David speaks with Nick about the errors we make when we try to understand each other, why we fail at The Newlywed Game, and the dangers of anthropomorphizing stocks. Thanks to Harry’s for supporting Motley Fool. Get your Free Trial Set – go to Harrys.com/fool

This time last year, David picked “5 Winners in a Thinking World,” highlighting 5 companies for the Information Age (or is it the Internet Age?). As always, these were meant as long-term picks (3 years at least), but today we’re checking in to see how they’ve doing in year one. Did you buy shares? Are you doing a happy-dance?

Our mailbag is an embarrassment of riches! So many great questions that we can’t possibly get to them all, which is indeed a great problem to have. After a quick guide on how to get your questions answered, both here and elsewhere at The Fool, David takes on how many stocks make the perfect portfolio, how much cash to save for the next down market, how to add to winners, and much more.

Spring is here! The air is warming, cherry trees have peaked, and showers are bringing flowers. But if you Google “April” today, your first page of results will be all about April the Giraffe and her brand new, web-cam-friendly calf. David doesn’t mention any of this specifically in today’s show, but he does pick 5 stocks that he thinks will go giraffishly up. We’ll check back in 3 years to see how these stocks have performed, and to see if anyone remembers our long-necked YouTube sensation. Thanks to Warby Parker for supporting Motley Fool. Order your FREE Home Try-On's at http://www.warbyparker.com/fool

In the early years of The Motley Fool, an unlikely opportunity came knocking. This is the tale of how David almost became the next Warrior Princess -- and a lesson in how keeping the long game in mind will help you in life, in business, and in investing.