Big Questions with Cal Fussman
As a bestselling author, speaker and one of the greatest interviewers of this generation, Cal Fussman has sat down with some of the world’s most influential individuals: Muhammad Ali, Mikhail Gorbachev, Serena Williams, Jeff Bezos, Jack Welch, John Wooden, Al Pacino and hundreds of others, digging deep into their hearts and delivering their wisdom to the rest of the world. Now, in Big Questions, Cal continues his journey. Uncovering the heart, head, and soul of his guests in thoughtful, deep and entertaining conversations.
Episodes
After a devastating rugby injury to his spine seven years ago to this day, Robert Paylor was told he'd never walk again and the best he could hope for would be to one day be able to pick up a slice of pizza. He’s defied every expectation—standing to receive his college diploma and walking today with the help of a walker. In this episode, Robert shares the mindset that rewired his future, and Cal explores how breakthroughs in AI cou...
A single year can easily get lost in time or echo for centuries. A thought-provoking conversation with Simon Sinek makes Cal take a look back at 1925, 1825, 1725, and 1625 — and forward to wonder if 2025 will be the most transformational year humanity has ever seen. Artificial intelligence is accelerating us forward and making us wonder how we’re going to evolve. At the same time, it brings more value to the human touch and enhance...
For decades, Cal steered clear of pharmaceuticals. But after assembling a new team of doctors and stepping on the scale and noticing a few extra pounds, he heard the same three letters over and over: GLP. These new drugs—GLP- 1s—aren’t just helping people shed pounds. They’re helping snuff out the brain’s hijacked hunger signals, replacing the relentless “more, more, more” with something almost revolutionary: “less is enough.” In t...
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...
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 oddl...
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 everythi...
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, remi...
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 some...
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 leave...
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...
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...
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 Gr...
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 b...
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, fo...
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