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.

Quincy Jones, Toby Keith, David Sanborn and others passed on in the last year – but their music lives on. Which makes Cal wonder if we all have a shot at immortality in the age of AI. Listen up, and get more out of your life.

The remarkable story of a boy who once dove into a swimming pool that didn’t have any water in it because he couldn’t admit that he was going blind and couldn’t see that he was headed for concrete, and how that boy turned into the CEO of Guiding Eyes for the Blind, a married father of four, a board member and a finisher of The Boston Marathon and The New York Marathon. Thomas Panek’s story is relevant to all of us, for it shows us the gifts that we can all receive once we push aside our pride and reach out for help.    

Sandro Corsaro, Head of Global Creative and Content at Wayfair, discusses the intricate dance between humanity and technology. He shares his father's inspiring immigrant story, highlighting resilience and dreams. The conversation delves into creativity in the age of AI, balancing traditional artistry with modern tech. Sandro emphasizes the importance of storytelling in maintaining human connections and reflects on how our legacy evolves in a rapidly digital world. His insights inspire listeners to embrace innovation while staying true to their roots.

What happens when an artist at the peak of his craft—known for iconic Time Magazine covers, music videos for legends like U2 and Metallica, Sundance documentaries and photographs in the permanent collection of the Metropolitan Museum of Art—navigates the rise of AI? Discover how Matt Mahurin sees creativity in this thought-provoking episode. Perfect for anyone curious about staying on top in an ever-changing world.