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What makes someone an optimist? How do you embody optimism? Who is on your Mount Rushmore of Optimists? And, should we “gather all the optimists and eat the pessimists”?! Cultivating optimism, with Bill Burke, founder of The Optimism Institute.

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The 101st mailbag may not seem as momentous as the one that ended with "0" but Fools know that big round numbers are just a milestone on the path to the future. Today we mark our charts for the course ahead, and hear from the delightful crew that we're sailing with on this ship of Fools. Yo, ho, ho, it's the March Mailbag!

Host: David Gardner Producer: Rick Engdahl

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It all comes down to this... Who will be the National World Champion of The Market Cap Game Show? In one corner is Bill Mann and in the other is Andy Cross, both investing gurus and indelible Fools. But we're betting on you to come out smarter, happier, and richer as we all play and learn together!

Companies discussed: UNP, WD, UBER, SYNA, SRAD, USB, NARI, DXCM, TDOC, PI, LYV

Host: David Gardner Guests: Bill Mann, Andy Cross Producer: Rick Engdahl

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We hope you've filled out your bracket because we're back with the second match of the March Market Cap Madness Final Four. Today it's the OG, Matt Argersinger up against the globetrotter, Bill Mann! Who will make it to next week's final? You will, Fool!

Companies discussed: ELF, MIDD, CCL, ABNB, BRC, EBAY, CRNC, KLG, PAC, BBW

Host: David Gardner Guests: Bill Mann, Matt Argersinger Producer: Rick Engdahl

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The Olympics. The World Cup. The Super Bowl. These competitions bring the world together to back their favorite teams as they compete for the ultimate title. But March Market Cap Madness has an even bigger draw, because you not only get to root for your favorite; you get to compete! Strap in and get your pencils ready, it's go time!

Companies discussed: INTU, CMG, MMM, LUV, NTB, TSLA, SNBR, DOC, SSNC, VBAH

Host: David Gardner Guests: Andy Cross, Emily Flippen Producers: Dez Jones, Rick Engdahl

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When the party's over, turn out the lights? No way, Fool! Head on over to the after-party and keep the good times rolling! Last Wednesday we had an epic 100th mailbag, joined by several of our long-time listeners. Today we extend that conversation and dig-in to four beautiful questions to make us all smarter, happier, and richer.

Host: David Gardner Guests: Jason Moore, David Geck, Jumm, Adam Nelson, Mike McMahon, Jason Newman Producer: Rick Engdahl

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We've always held that the mailbag is a chance for us to learn from each other; to hear the thoughts of Fools from around the world who listen to the show and then respond with wisdom of their own. Today, as we celebrate our 100th mailbag, we're kicking it up a notch! Get ready to meet seven of our most brilliant and prolific correspondents, and this time hear their voices as well as their stories.

Host: David Gardner Guests: Jason Moore, David Geck, Jumm, Jason Trice, Adam Nelson, Mike McMahon, Jason Newman Producer: Rick Engdahl

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It's time again for an old format, a new show, borrowed wisdom and some blue sky thinking! You don't have to be a bride to join in the good luck this week.

• (04:31) Style Boxing
• (14:23) The Golden Ticket
• (21:43) The Why of Work
• (29:25) A Study in Blue

Companies Mentioned: MORN, DIS, ABNB, NFLX, TSLA

Host: David Gardner Producer: Rick Engdahl

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Does cost equal quality? Can your smart watch make you even smarter? And where on Earth is rule.breaker.investing? You're about to be smarter, happier, and richer, Fool! Time for some tips, tricks, and lifehacks.

Host: David Gardner Producer: Rick Engdahl

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