• The First Job – After AI
    Dec 23 2025

    When Cal visits an old mentor, he's struck by two realizations. First: Some of the most profound moments in a young person's life can happen in entry-level jobs, when the right person takes you in, opens a door, and points you on the right path. Second: As artificial intelligence wipes out many of those first jobs, it will also erase those connections and moments. What disappears isn't just work. It's mentorship. It's the quiet bonds that shape confidence, character, and destiny. What will happen to a generation shaped without them? And an even bigger question: How might we be able to preserve them?

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    12 mins
  • The AI Argument: 2026
    Dec 16 2025

    There are those believe artificial intelligence will cure cancer, reverse global warming, and unlock human potential. There are others who believe it will end everything we know. For the first time in history, both sides may be right. We are living inside the most consequential argument humanity has ever had — and the clock is ticking.

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    11 mins
  • Cal Finds His Destiny
    Dec 9 2025

    When Cal returns to Tampa's Ybor City to speak, he keeps a ritual that's become almost sacred: a meal at the legendary 120-year-old Columbia Restaurant, followed by a quiet moment of thanks to the man who first sent him there — Muhammad Ali's doctor, the renowned Ferdie Pacheco. Ferdie wasn't just the "Fight Doctor." He was an artist, a storyteller, and a man with a taste for a good practical joke. After his meal, Cal goes to pay tribute to Ferdie through his painting that hangs near The Columbia's kitchen. Only this time, the painting is gone, and it feels to Cal like an old friend has vanished. What happened next left Cal with a twist he couldn't see coming — and a hint that destiny sometimes whispers through the strangest openings. Listen in to hear the story unfold.

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    11 mins
  • AI Job Advice: Look Back, Leap Forward
    Dec 2 2025

    The future may not be hiding in Silicon Valley. It could be hidden in your childhood. When a bright young grad sits down at Cal's Thanksgiving table worried about AI layoffs and disappearing careers, Cal offers an unexpected roadmap: Don't try to predict the future . . . remember it. Some of the greatest innovators didn't choose their path — their childhood chose it for them. In this episode, Cal shows how a single moment from your early life can reveal where you're meant to go next in an AI-shaken world. If you're wondering what job will survive the robots, why not start with the kid you used to be, then project forward.

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    13 mins
  • Till Tech Do Us Part
    Nov 25 2025

    Here is a question Cal never thought he'd ask. Let's just say a human marries an AI and they get divorced. Does ChatGPT get the alimony? This is the way we need to begin thinking after news came out that a Japanese woman married an AI bot. Buckle your seatbelts. It's the groundswell of statistics on the romantic mingling between humans and AI that will raise your eyebrows to the middle of your forehead.

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    8 mins
  • Boredom Never Stood A Chance
    Nov 18 2025

    When Cal looks back on his life, he sees a relentless drive that's guided him to his 69th birthday: Never be bored. His past reveals a simple truth. Boredom ends where curiosity begins.

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    14 mins
  • Your Best Thanksgiving
    Nov 11 2025

    Cal looks over a bountiful breakfast menu and remembers the statistics he heard about kids going hungry in Tampa Bay — a city that, through his traveler's eyes, appears to be flourishing. When you hear the numbers, you'll understand how giving just a little can make this your best Thanksgiving ever.

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    10 mins
  • Turning Fandom Into Family
    Nov 4 2025

    When Kobe Bryant watched the Eagles win Super Bowl 52 on television, he wasn't alone — he was holding his 1-year-old daughter, Bianka, in his arms. That moment, captured on home video, wasn't just about football. It was about the way a team becomes a language between generations. Rewatching that clip sends Cal into a reflection of his own: the passion for sporting events his father passed on to him, and the emotions he passed on to his son. This episode is about the deep inheritance that lives inside sports — identity, loyalty and love. The Los Angeles Dodgers recent World Series win shows Cal how the games can outlive us in the hearts of the people we leave behind.

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    8 mins