Siri didn’t emerge from a single mind—it was the product of many brilliant innovators. But in this episode, Cal talks with one of the key founders behind the company that built the digital assistant Steve Jobs had to have. Norman Winarsky takes us back to the moments Siri first stunned the world in the testing phase in 2009 and 2010 and shares his thoughts on today’s AI revolution—what excites him, what concerns him, and what leaves him in awe.

Donald Trump divides opinions like few others—some love him, others loathe him. But over the next four years, his most impactful decisions might not be about politics as usual. Instead, they could shape the future of artificial intelligence -- and humanity. In this thought-provoking episode, Cal dives into why the President’s moves in AI policy will matter to everyone regardless of their political stance—and why getting it right is crucial. A commentary from NotebookLM.com adds some twists to Cal’s insights and is further evidence that AI will continue to take us to places we can’t yet imagine.

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.

Emmy nominated Producer, Author, Animator and Creative Executive for Disney, NBCUniversal and Wayfair has a fascinating conversation with Cal about the ever-evolving intersection of humanity, creativity and technology. Sandro has opened the door for Cal to translate the power of questions and storytelling into new areas, and this episode will leave you inspired to embrace the future while staying rooted in who you are.

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.

Feeling stuffed after Thanksgiving? Meet YUKA, the revolutionary app with over 64 million users worldwide. Just scan a product's barcode, and YUKA instantly reveals whether it's BAD, POOR, GOOD or EXCELLENT for your health. Join Cal as he dives into how this app is changing the way we shop—and why you should start using it too. This quick, fun, and eye opening episode can improve your health. Don’t miss it!

Cal talks with the founder of Cicero – a company that uses artificial intelligence to allow you to have conversations with Aristotle, Abraham Lincoln, Winston Churchill, Michael Jackson and many other influential figures over the centuries. You see them as they actually looked and hear them in their own voices (when possible). Content is based on records of what they wrote and said. It fulfills a vision of Steve Jobs – who, back in 1985, believed that one day we’d be able to talk to people of this magnitude through the computer. Listen to the story of how it all came together and join the waiting list at heycicero.com.