Rule Breaker Investing

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

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

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

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

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

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

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

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

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

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