Rule Breaker Investing

After three weeks of Authors in August, the authors step aside and Rule Breaker listeners take the conversation somewhere new.

A middle-school teacher wrestles with what happens when the measurements meant to improve education begin defining it instead. A father investing for his daughters wonders whether “Add Up, Don’t Double Down” applies to index funds. There are Rule Breaker songs, Spiffy Pops shared between old friends, and, near episode end, the Fool who originated Pet Perks returns with an audio reminder that some of life’s most valuable moments can be hiding inside the everyday hassles we’re tempted to hurry through.

Host: David GardnerProducer: Bart Shannon

Ken's full playlist:

For failing to become an active financial investor:

* Cast Your Fate to the Wind (George Winston)

For letting your winners run high:

* Along for the Ride (Mates of State)

* All Time High (Rita Coolidge)

For brand new investors:

* Any Dream Will Do (Donny Osmond)

* Come and Get It (Badfinger)

* Don’t Be Afraid (Boston)

* Enjoy Yourself (The Jacksons)

* Faith (George Michael)

* Follow that Dream (Elvis Presley)

* Go Your Own Way (Fleetwood Mac)

Watching investments compound and grow:

* Chain Reaction (Diana Ross)

* Celebration (Kool and the Gang)

* Hitch a Ride (Boston)

* More Today than Yesterday (Spiral Staircase)

For spiffy pops:

* Breakout (Swing Out Sister)

* Feels So Good (Chuck Mangione)

* Can’t Help Falling in Love (Elvis Presley)

* Do It Again (Steely Dan)

* Glad All Over (Dave Clark Five)

* Happy (The Carpenters)

Paying capital gains tax:

* Don’t Fear the Reaper (Blue Öyster Cult)

When a stock doubles:

* Double Lovin’ (The Osmonds)

Selling stocks:

* Breaking Up is Hard to Do (Neil Sedaka)

Inevitable market downturns:

* Don’t Go Breaking My Heart (Elton John and Kiki Dee)

* Don’t Worry, Baby (The Beach Boys)

* Hold On (Wilson Phillips)

* I’m Still Standing (Elton John)

* It’s All Right (Gerry and the Pacemakers)

* It’s Gonna Be Okay (Piano Guys and Cliff Richard)

* Let’s Hang On (The Four Seasons)

When deciding to buy a new stock:

* How Will I Know? (Whitney Houston)

Investing in thirds:

* Just a Little Bit (Robbie Nevil)

Before you figure out your sleep number:

* (Last Night) I Didn't Get to Sleep at All (The Fifth Dimension)

* If You Can’t Sleep (She & Him)

Putting all your money in only one stock:

* Brink of Disaster (Lesley Gore)

Investing for the long-term:

* Carry On (Crosby, Stills, Nash, and Young)

Retiring after a successful investing career:

* Cake by the Ocean (DNCE)

* Fun, Fun, Fun (The Beach Boys)

RBI’s optimistic attitude:

Life is Good (Ringo Starr)

This episode was sponsored by Coveron. One scam can cost you everything. Protect yourself now. The first 100 users get 20% off with code rule20 at coveron.com/rule20

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Why do we work? A paycheck matters, of course. And, when so much of life is spent working, might we reasonably hope for something more?Closing out the ninth year of Authors in August, David welcomes Dave Ulrich, one of the world’s leading thinkers on organizations, leadership, and human capability. Using the longtime favorite The Why of Work as a jumping-off point, their conversation ranges widely across what gives work meaning, what great leaders understand about people, and what decades spent studying organizations have taught Dave about the ways we work—and why!

As technology transforms the workplace and old assumptions keep getting rewritten, some decidedly human questions endure. What makes work worth doing? What brings out the best in people? And how might we create workplaces that leave employees, customers, and the world better off?

Host: David GardnerGuest: Dave UlrichProducer: Bart ShannonCompanies Mentioned: ADBE, JWN, WMT
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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
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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 GardnerGuest: Thi NguyenProducer: 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 GardnerProducer: Bart Shannon

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