What would you choose: A shot at March Madness glory or a massive NBA contract? Cal dives into the $100 billion-dollar question facing Cooper Flagg—and what his decision tells us about ambition, friendship, legacy, and the values we hold as a society. A must-listen for anyone who’s ever faced a difficult choice.

Ever wonder what's truly behind President Trump's controversial tariffs? Cal turns to his go-to expert—Ozan Ozkural, the astute international banker he first met at Larry King's breakfast table and a member of the influential Brookings Institution Foreign Policy Leadership Council. In this episode, you'll uncover the hidden reasons behind the tariffs, the surprising geopolitical implications, and critical deadlines approaching fast that no one else seems to be talking about. Ozan travels the world and gets to understand global finance from many viewpoints. Listen up, and you will, too!

What if you could talk to John F. Kennedy today? In this episode, Cal sits down with an AI recreation of the 35th president for a conversation that’s part history and part mystery. Why did JFK keep a coconut shell on his Oval Office desk? How did he view Greenland during the Cold War? Who was the most magnetic person he ever met? And yes—they even dive into his thoughts on artificial intelligence. Unexpected, illuminating, and oddly timely. Hit play and find out why JFK still has something to teach us.

Cal reflects deeply on a man known by millions as the smiling face behind the grill—and the heavyweight champion who stunned the world by reclaiming the title at age 45. With the recent passing of Foreman at the age 76, Cal looks deeply at George’s greatest accomplishment: his transformation of character. George proved it’s never too late for anyone to reinvent themselves. What can we learn from his remarkable journey? Listen now and discover how George Foreman’s story could inspire you to rewrite your own.

What if you could sit down and talk to John Lennon today? In this one-of-a-kind episode, Cal has an astonishing conversation with an AI-powered persona of the legendary Beatle, created by heycicero.com. At certain moments, the back-and-forth felt eerily real as John reminisced about writing Help!, I Am the Walrus, Strawberry Fields Forever, and, of course, Imagine. But this chat goes far beyond music—John and Cal dive into everything from the Beatles' famous pillow fight to the deeper question: Why do humans harm and kill each other? Pour yourself a cup of tea, press play, and experience a conversation that blurs the lines between past and future. As John reminds us in the end: Love is all you need.

Cal draws pocket aces and wins big in the first hand of a charity poker night raising money for the fight against cancer. The surge of luck makes it feels like it will be his lucky day. But then his luck seems to begin turning up in everyone around him. Only at the end of the night does he realize that it’s his luck to be with everyone that he’s touched. Enjoy the story . . .

As Cal watches the Academy Awards, he has a startling realization—he’s barely stepped inside a movie theater all year. Then, host Conan O’Brien delivers a hilarious skit introducing home streamers to a wild new concept: the movie theater. The moment sparks a memory of an interview Cal once did with Leonardo DiCaprio, where Leo spoke passionately about his favorite films and the power of cinema. That interview is replayed here, reminding us all why the theater experience is worth rediscovering. So sit back, listen, celebrate the magic of the big screen.

Technology, history, and global politics collide in this episode after Cal asks ChatGPT if there is a way that he can stop a war. The question unexpectedly evolves into an exploration of the forgotten Nutmeg War—a historical conflict with surprising modern parallels. Cal connects the dots between this overlooked episode of history, the recent three-year conflict unfolding in Ukraine, and the buzz surrounding Greenland. This analysis is a window into how AI can show you history and the world around you in a way that you can’t get anywhere else.

After reading about Saturday Night Live's 50th anniversary, Cal turns to one of his AI assistants, Arbor, for recommendations on the freshest new comedians. What starts as a simple question about stand-up talents turns into an eye-opening look at how AI is reshaping the way we can discover entertainment—and how we’ll all be interacting with AI in the near future. Naturally, this podcast will also deliver a few laughs . . .

Marketing guru Seth Godin recently shared on The Tim Ferriss Show that people often ask AI simple questions—missing out on the real value of deeper conversations. Cal has been exploring this idea on Big Questions, using AI to dive into the legacies of Muhammad Ali, Kobe Bryant, and beyond. This week, the experiment gets personal. Struggling with his discomfort around social media, Cal turns to AI—not just for strategy, but for something deeper. Can AI help reframe his mindset? Can it act as a therapist, guiding him toward a healthier relationship with the digital world? The conversation takes some surprising turns, and what he discovers might just change how you think about AI. Tune in for an episode that blends tech, psychology, and personal growth in ways you won’t expect!