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 GardnerGuest: Vasant DharProducer: Bart Shannon
Learn more about your ad choices. Visit megaphone.fm/adchoices

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 GardnerGuest: Thi NguyenProducer: Bart Shannon
Learn more about your ad choices. Visit megaphone.fm/adchoices

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 GardnerProducer: Bart Shannon

Companies Mentioned: AMZN, AXON, ISRG, MELI, NVDA, PLTR, RKLB, SERV, SHOP, TEM
Learn more about your ad choices. Visit megaphone.fm/adchoices

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 GardnerProducer: Bart Shannon
Learn more about your ad choices. Visit megaphone.fm/adchoices

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 GardnerGuest: Karl ThielProducer: Bart ShannonCompanies Mentioned: GOOGL, EEFT, HAIN, BKNG, TSLA
Learn more about your ad choices. Visit megaphone.fm/adchoices