This June, ChatGPT took its first swing with five big questions about Rule Breaker Investing, and a new episodic series was born. Now, we’re back for Volume 2—with a baseball twist! ChatGPT pitches David five questions, each a unique pitch type:

1. Hardball: What separates Rule Breakers built to last from those destined to fizzle out?

2. Softball: Can David sum up Rule Breaker Investing in one sentence?

3. Curveball: What would make him rethink a long-term winner?

4. Screwball: Is there a traditional investing rule David (begrudgingly) respects?

5. Knuckleball: If he could pass on just one Rule Breaker principle, what would it be?

Come for the hardball, stay for the knuckleball!

Host: David Gardner

Guest: ChatGPT

Producer: Desirée Jones

Companies Mentioned: AAPL, AOL, ARM, AXON, BB, DDD, FIT, GPRO, IOM, K, META, NOK, P, TSLA, YHOO

Ever felt the chill of a silent room after asking for questions, only to be met with zero raised hands? Or maybe you’ve found yourself buried in commercials, losing valuable family moments during the big game. This week, David shares his latest volume of Mental Tips, Tricks, and Lifehacks with seven unique strategies to make life smoother, smarter, and a bit more joyful. From the Hemingway Bridge to transforming “FAILURE” into an unexpected love message, get ready for a dose of elegance, insight, and a little Rule Breaker flair — this week, only on Rule Breaker Investing!

Host: David Gardner

Producer: Desirée Jones

Mailbag! This week, David welcomes back an expert as we open up focusing on risk... in its prominent forms of tolerance and also capacity. Then, a non-partisan look at the upcoming election: “What truly drives America forward—regardless of political tides?” Some chicken soup for American souls..... At close, a special missive from a Foolish investor who shares his Magnificent Seven score along with a story that cannot fail to inspire.

Producer: Desirée Jones

Host: David Gardner

Guest: Amanda Kish

Do you want to hear something really scary? The kind of scary that could drain your accounts and seize your assets? Do not adjust your podcatcher, Fool! Robert Brokamp is back to shock, scare, and surprise you with stories from the dark side of finance. But fret not! He will also give you the keys to your survival.

• (7:08) There's No Theft Like Home
• (13:19) A Broker Making You Broker
• (20:40) The Silence of the Hams
• (29:36) Scamazon Prime
• (37:32) The Perfect Storm
• (47:48) Guardians of the Graceland

Host: David Gardner Guest: Robert Brokamp Producer: Rick Engdahl

You're already pretty smart, but let's go for even smarter! Our all-Fool cast is here to help you understand some common and not-so-common investing terms, so that you can be more fun at cocktail parties — and more importantly, be a better investor! Are we heroes? Are we zeros? Keep score and let us know.

Host: David Gardner Guests: Amanda Kish, Andy Cross, Sanmeet Deo Producer: Rick Engdahl

This week on Rule Breaker Investing, David welcomes Elaine Hungenberg, Senior VP of Partnerships & Impact at XPRIZE. Elaine explains how XPRIZE’s unique competition model sparks world-changing innovations, from space exploration to clean water solutions. In this lively conversation, discover how prize-driven innovation accelerates breakthroughs, hear about some of the most exciting XPRIZE projects, and learn valuable lessons from Elaine’s journey as a thoughtful disrupter. Tune in for a deep dive into creating impact, followed by our always fun, signature round of Buy, Sell, Hold!

Host: David Gardner

Guest: Elaine Hungenberg

Producer: Desirée Jones

Every stock tells a story. This week on Rule Breaker Investing, we gather around the campfire for the ninth time to share our best stock stories. From Meta Platforms’s long arc of growth to Warner Bros. Discovery’s debt-ridden saga, these stories aren’t just tales of companies; they are lessons for life and investing. David and his Motley Fool friends—Dave Meier, Mary Long, Nathan Alderman, and Tracy Dahl—recount their most memorable stock experiences.  Join us at the campfire!

• (3:17) The Long Arc
• (11:52) Catching Flies with Honey
• (22:22) David and Goliath but Not the Way You Think
• (36:46) You Have More Than You Think
• (46:28) That’s the Last Time I’m Ever Going to Do That

Companies Mentioned:

BMBL, BRK, META, WBD, YHOO

Host: David Gardner

Guests: Dave Meier, Mary Long, Nathan Alderman, Tracy Dahl

Producer: Desirée Jones

On the road and looking at a light mailbag, David writes his own beautiful question this month, using it as an opportunity to highlight five favorite moments from the Rule Breaker Investing podcast in 2024.

Companies Discussed: AAPL, AMZN, GOOG, META, MSFT, NVDA, TSLA

Host: David Gardner

Producer: Desirée Jones

Welcome back to our quarterly Market Cap Game Show! This week, two past champions, Matt Argersinger and Yasser El-Shimy, face off in a battle of wits and estimates, each vying for the coveted seat in our 2025 “March Market Cap Madness” World Championships. With 10 stocks on the line and two throwdown rounds, who will come out on top? And how will you fare against our contestants? Whether it’s semiconductors, space exploration, or the future of sound systems, we’ve got an exciting lineup of companies for you to test your market cap knowledge. Can you outscore both guests?!

Companies Discussed:

NBIX, RKLB, AMD, SHOP, SYNA, MSFT, LOW, SONO, HEI, KFRC

Host: David Gardner

Guests: Matt Argersinger, Yasser El-Shimy

Producer: Desirée Jones

Investing rewards those who play the long game. While short-term trading can capture gains, true wealth comes from thinking in years, even decades. This applies not just to investing, but also in business, leadership, and life. This week, David interviews Rand Stagen, Managing Director of Stagen Leadership Academy, and one of David’s favorite people in business. Rand shares his wisdom on the long-term development of leaders and organizations, why conscious leadership is crucial for businesses today, and the lessons we can all learn from playing the long game in every aspect of life. Along the way, they’ll explore the balance of business, family, and legacy, and even tackle some Buy, Sell, or Hold predictions for the future of leadership.

Host: David Gardner

Producer: Desirée Jones

In this sixth installment of Essays from Yesterday, David takes us on a journey back through time to revisit some of his earliest (and sometimes prophetic) investment writings from his days as a Motley Fool newsletter contributor. From reflections on the volatility of 2007-8, to introducing new terms like “Big Dumb Money,” and thoughts on building mental frameworks for investing, David reacts to his past essays with fresh insights for today’s markets. Join us as we explore the lessons learned from history and how they continue to guide our investing journeys today.

3:56 - #1 January is the Best Month

12:14 - #2 Big Dumb Money

21:34 - #3 Frameworks for Investors

31:46 - #4 Fool’s Eye on Investing

Companies Discussed: CHKP, CSCO, FTNT

Host: David Gardner Producer: Desirée Jones