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.

A charity poker night kicks off with a thrilling win, setting the stage for an evening that soon becomes about more than just luck. Amidst laughter and camaraderie, attendees forge deep connections, emphasizing the power of community and meaningful questions. As the night unfolds, the true fortune reveals itself through shared stories and support for cancer initiatives. With the goal of raising $300,000 in honor of a beloved friend, the atmosphere vibrates with hope and the spirit of giving.

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!

Norman Winarsky, a venture capitalist and one of the founding minds behind Siri, sheds light on the revolutionary journey of AI. He reflects on Siri's stunning early tests and the collaborative innovation that shaped its development. Norman discusses AI's transformative potential, comparing it to the internet's impact, and emphasizes the importance of human-AI collaboration. He also addresses the changing landscape of higher education in the context of these advancements and the need for creativity in the evolving job market.

The discussion dives into Donald Trump's polarizing impact on AI policy and its potential to reshape humanity. Listeners explore his evolving views on technology and the ethical dilemmas posed by AI advancements. Insights are shared on how personal experiences influenced Trump's leadership style. The conversation urges a rethink of political ideologies amidst the rise of robotics and the implications for immigration and economic strategies. There's a focus on the necessity of citizen engagement as society navigates these complex technological changes.