Big Questions with Cal Fussman

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.

As we approach the fifth anniversary of Kobe Bryant’s passing, Cal dives deep into a fascinating discussion with Claude AI about the relentless spirit of competition that defined the NBA great. But the conversation takes an unexpected turn when Cal asks Claude if it competes with ChatGPT and other AI models. Join this thought- provoking journey as Cal uncovers lessons about the two sides to competition and simultaneously learns how to ask AI better questions to unlock its potential.

January 17th marks what would have been Muhammad Ali’s 83rd birthday. To honor his legacy, Cal embarks on a unique journey—reconnecting with his childhood hero through ChatGPT. Along the way, he discovers a powerful truth: asking the right questions is the key to unlocking the answers we seek about artificial intelligence and beyond. This episode explores the intersection of curiosity, technology, and the timeless lessons of The Greatest.

Discover the astonishing ways your daily life reveals more about you than you could ever imagine. Columbia University professor Sandra Matz takes you on a journey through the hidden world of data collection, showing how a single routine hour in the morning can generate more data than was used to send a spacecraft to the moon. In this eye-opening conversation with Cal, explore an era in which those who collect our data may know us better than we know ourselves. See the power your digital footprint holds over your life and what it means for our future.