Rule Breaker Investing

ChatGPT Asks & David Answers, Vol. 4

September 16, 2026·50 min
Episode Description from the Publisher

ChatGPT is back on the mound, David is back in the batter’s box, and for the first time in more than a year it’s time for five fresh pitches.This time, the questions aren’t quizzes—they’re provocations. What advantages did David have as an investor at 30 that he no longer has at 60—and what has he gained in return? Which Rule Breaker principle might prove less durable over the decades ahead? What could the future price of a single company tell us about the future of the world? And when two very different kinds of Rule Breakers compete for one spot in your portfolio, which way do you swing? Five questions designed to challenge assumptions, expose blind spots, summon a few strange hypotheticals, and perhaps produce an answer or two David himself didn’t know he had.ChatGPT asks. David answers. Five questions, five swings. Play ball! Companies Mentioned: AAPL, AMZN, GOOG, ISRG, NFLX, NVDA, PLTR, RKLB, SPCX, SPY, TSLA Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

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