Rule Breaker Investing

Artificial intelligence may feel suddenly everywhere, but AI pioneer Vasant Dhar has had a front-row seat for more than four decades—teaching AI, building companies around it, and bringing machine learning to Wall Street long before ChatGPT entered the conversation.

For the second week of Authors in August, David sits down with Dhar to ask not merely what machines can do, but how humans can think with them. When should we trust AI? When does it sharpen our thinking—and when does it make our brains lazy? If intelligence itself is becoming a commodity, where will tomorrow’s value be created? And in a future where machines become extraordinarily capable, what are humans for?
A conversation about AI, investing, trust, judgment, and our increasingly intelligent future.

The Damodaran Bot is available for public use at: damodaranbot.com

Vasant's monthly newsletter can be found at: vasantdhar.substack.com

Host: David Gardner
Guest: Vasant Dhar
Producer: Bart Shannon

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Authors in August is back! It’s our 9th year featuring authors of books that David loves and thinks you’ll love too.

So for the third time, philosopher and game scholar Thi Nguyen joins back with Rule Breaker Investing—and this time the conversation reaches far beyond games.

What happens when the scores we invent to measure success begin quietly reshaping what we value?

Together, in an incredibly wide-ranging discussion, David and Thi explore rankings, metrics, investing, institutions, artificial intelligence, and the subtle difference between playing a game… and letting the game play you. And we close with a rousing round, as ever, of Buy, Sell, or Hold?

Whose scorecard are you living by?

Host: David Gardner
Guest: Thi Nguyen
Producer: Bart Shannon

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As Rule Breaker Investing enters its twelfth year, it is fitting to hand the microphone back to the people who have helped shape it from the very beginning: our listeners.
This month’s Mailbag spans investing, artificial intelligence, financial freedom, World Cup soccer, custodial Roth IRAs, Rule Breaker stock selection… and even a soundtrack for Foolish living?! Along the way are a heartbreaking story, practical questions, imaginative ideas, and reminders that the best investing community doesn’t simply exchange stock tips—we help all of us become smarter, happier, richer. And perhaps a little wiser, too.
Host: David Gardner
Producer: Bart Shannon

Companies Mentioned: AMZN, AXON, ISRG, MELI, NVDA, PLTR, RKLB, SERV, SHOP, TEM

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It’s become something of a midsummer tradition on Rule Breaker Investing: set aside the markets for a week and simply follow curiosity wherever it leads.
This year’s sampler wanders through technology, sports, business, demographics, literature, and a few unexpected places in between. Along the way are thoughts about how to get the most out of AI, a few tweaks that could improve the world’s biggest sporting event, a prediction about who may be becoming the world’s most valuable people, and a dramatic reading of one of David’s favorite short stories.
Two pages.
Idle thoughts for you, of a summer’s day.
Host: David Gardner
Producer: Bart Shannon

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In the anxious days following Brexit, rather than predict the future, David asked a different question: Where are the opportunities? The result was a five-stock sampler built not on politics, but on optimism.
Now a full decade has passed. Joined by longtime Fool Karl Thiel, we crack open the time capsule, revisit the original investment theses, score all five stocks against the market, and ask what a ten-year scorecard can teach that three years never could. Some ideas exceeded expectations. Others humbled us. All of them remind us why Rule Breakers look beyond the headlines and invest for the long haul.

Host: David Gardner
Guest: Karl Thiel
Producer: Bart Shannon
Companies Mentioned: GOOGL, EEFT, HAIN, BKNG, TSLA

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Every so often, five quotations come along that don’t merely make you nod. They make you stop, put the book down, and think.
This week we explore why the best investors first become students of themselves, why our minds work better when they’re surrounded by rich ideas, why business is one of humanity’s great engines for creating value, why prosperity may make societies not just wealthier but wiser, and why one vision of America argues that a nation’s greatest competitive advantage isn’t its geography or its resources—it’s its ability to continually renew itself.
Five quotations. Five conversations. And perhaps one or two ideas that will quietly change the way you see investing, business, and life.
Happy 250th to the US of A!
Host: David Gardner
Producer: Bart Shannon
Companies Mentioned: AMZN, MCD, NVDA

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Each Independence Week, Rule Breaker Investing asks a simple question: What have you done over the past year to create financial freedom—for yourself or for others? This year’s answers feature a listener’s Declaration of Financial Independence and a young woman whose very first stock purchase turned out to be… Nvidia. Along the way, we revisit three favorite moments from the first three years of this annual tradition, discovering that the path toward financial freedom may be simpler than it first appears: Believe. Persist. Pass it on.
Happy Independence Week—and may financial freedom continue to echo like a Liberty Bell.
Host: David Gardner
Producer: Bart Shannon
Companies Mentioned: NVDA, SCHW

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This month’s Mailbag ranges from Washington, D.C. to Germany, from the SEC to the moon, and from individual stock ownership to the deeper question of what freedom is actually for. Along the way, fellow Fools write in about transparency, curiosity, market caps, parenting, AI, adding to winning investments, and what can happen when decades of patient investing quietly compound into opportunities to help others.
As always, the best part of the Mailbag is you.
Host: David Gardner
Producer: Bart Shannon
Companies Mentioned: HAS, ISRG, JEPI, KO, MAT, MSCI, NKE, NVDA

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The Market Cap Game Show returns for its 42nd installment, with longtime Motley Fool personalities Charly Travers and Jason Moser battling for a coveted spot in next March’s Market Cap Madness Final Four.
But this episode marks something new. For the first time, players can invoke the King-Sharon Rule, adding an extra layer of strategy, risk, and reward to the game. Agree or disagree is no longer the only choice. Feeling confident? Call “higher” or “lower” and put an extra half-point on the line.
Ten stocks. Two seasoned competitors. One brand-new rule. And for reasons that only became apparent while recording, an unusually heavy concentration of food, cars, food delivered by car, food consumed after getting out of a car, car parts, collector cars, and at least one company that makes spices for the food.

Host: David Gardner
Producer: Bart Shannon

Companies Mentioned: DASH, GPC, HGTY, MKC, MTN, OC, RACE, SYY, TDG, TEAM

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For the twelfth time, we gather around the campfire for one of RBI’s favorite traditions: Stock Stories. Five Fools. Five investing lessons.
This summer’s tales share a surprising common thread: A biotech shell company that refused to die. An old gift of IBM stock quietly compounding for decades. A Fool who finally bought Alphabet nearly twenty years after he first meant to. A company called Life360 proving that “obvious” doesn’t mean “fully valued.” And a producer awakening to stock-market investing in his 50s.
The lesson? You may think you missed it. You probably didn’t.
Pull up a chair, grab a marshmallow, and join us around the campfire.

Host: David Gardner
Producer: Bart Shannon

Companies Mentioned: GOOGL, IBM, LIF, UBER (and some random CUSIP#!)

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