It was during the pandemic when Cal first realized how many people were searching for mental health professionals and couldn’t find them. Cal wished everyone could have access to the best therapist he’s ever met – Sallie Sanborn. But nearly 40 percent of Americans now live in what’s called Mental Health Professional Shortage Areas. So it should be no surprise that artificial intelligence has stepped into the void. Cal talks with Neil Parikh, one of the founders of TalkToAsh.com about the app tha...
Jul 22, 2025•22 min•Season 4Ep. 134
Cal has long believed the best way to avoid regret is to really listen when someone talks about theirs. One answer came to him during an interview with the actor Robert De Niro. Another, just recently, from the Godfather of Artificial Intelligence on a podcast. Both answers led Cal to a day he’ll never forget—and they just might lead you to one, too.
Jul 15, 2025•12 min•Season 4Ep. 133
Cal hears an interview with Kevin O’Leary – Mr. Wonderful on Shark Tank -- that puts into focus the loss of jobs coming with the onset of AI. Then he sees a robot cleaning floors at the convenience store of his gas station. And he wonders about the possibility and potential of Universal Basic Income in a world where there may not be that many jobs for humans to find. That leads Cal to Bill Gates and some thoughts on UBI that you definitely want to hear.
Jul 08, 2025•16 min•Season 4Ep. 132
Cal reads a Wall Street Journal story about a graduation speech that ends with the audience asked to sing Bill Withers’ Lean On Me—a soulful anthem for uncertain times. The Class of ’25 faces a tough job market. Internships are disappearing to AI. Roughly 70% of Americans say they don’t trust companies to use artificial intelligence responsibly. And only one in six people are using it at work. Many who don’t use it are fearful of trying. Instead of commiserating, Cal makes a case for collaborati...
Jul 01, 2025•15 min•Season 4Ep. 131
After speaking at a CREW conference in Texas, Cal meets a smart young Uber driver who was curious about the number of jobs that we can anticipate losing in America because of AI. The driver wanted to know what the lives of Americans who’d most likely lose their jobs were going to look like, and how these people might get by and transition. Cal finds some answers from Sam Altman, the CEO of OpenAI, and Geoffrey Hinton, the Godfather of Artificial Intelligence. He also discovers a half-helicopter/...
Jun 24, 2025•23 min•Season 4Ep. 130
When an interview on AI and the future of warfare gets postponed by the birth of a child,Cal turns to the web to satisfy his curiosity on the topic —and stumbles upon something larger than he expected. What he finds is a fresh way to look at conflict in the age of intelligent machines… and an idea that could change everything. It’s simple. It’s ancient. And it’s something Elon Musk says may be our last best hope: curiosity. Tune in—this episode might just rewire how you see the future of war… an...
Jun 17, 2025•18 min•Season 4Ep. 129
Cal reads about artificial intelligence models that have written their own code in order to escape being shut down. He ponders the friction between the light side and dark side of AI as he mourns the passing of the photographer Sebastiao Salgado, who made a life of finding the best in humanity in some of the darkest times imaginable. Sebastiao and his wife, Lelia, replanted a denuded ranch in Brazil that had lost its birds and animals with 2.5 million trees and restored it into a pristine forest...
Jun 10, 2025•12 min•Season 4Ep. 128
Cal takes a breath of fresh air after a friend goes through double lung-transplant surgery and comes out with a new life. This story will make anyone with a medical problem wonder about the possibilities of medicine in the age of AI.
Jun 03, 2025•8 min•Season 4Ep. 127
What kind of person runs 1,000 kilometers in 12 days – twice? Meet Natalie Dau, a Guinness World Record holder who doesn’t just push the limits of human endurance — she redefines them. Cal dives deep with Natalie to uncover how she uses pain as fuel, movement as a message, and her voice — amplified by AI — to raise money, shift perspectives, and help people live better lives. But beneath the inspiration lies a bigger global question: What happens to a world divided between those who have access ...
May 27, 2025•30 min•Season 4Ep. 126
In times when college students are using artificial intelligence to answer even introductory course questions like: “Briefly introduce yourself and say what you’re hoping to get out of this class?” we really have to wonder about how education is going to adapt to a future where students delegate nearly all their classwork to AI. Cal speaks with James D. Walsh after Walsh’s New York Magazine article revealed a seismic shift that’s redefining the word “cheating” and nudging teachers to think about...
May 20, 2025•50 min•Season 4Ep. 125
In ten years, we’ll create content as fast as we can think it. That’s what the owner of a cutting-edge AI studio told Cal—and something clicked. This wasn’t just about technology. It was about humanity, about carbon merging with code. That’s when Cal decided to document the great unfolding: The evolution of our species as we begin to step into the future with artificial minds. This podcast isn’t exactly Charles Darwin sketching “I think” above the first evolutionary tree before going on the path...
May 13, 2025•13 min•Season 4Ep. 124
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 could one day remove the walker entirely. This is more than a comeba...
May 06, 2025•55 min•Season 4Ep. 123
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 enhances our creativity. This is not the time to turn away from AI with ...
Apr 29, 2025•14 min•Season 4Ep. 122
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 this episode, Cal explores what happens when we hand over the mic ...
Apr 22, 2025•13 min•Season 4Ep. 121
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.
Apr 15, 2025•13 min•Season 4Ep. 120
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 that no one else seems to be talking about. Ozan travels the wor...
Apr 08, 2025•26 min•Season 4Ep. 119
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 te...
Apr 01, 2025•36 min•Season 4Ep. 118
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 rewri...
Mar 25, 2025•22 min•Season 4Ep. 117
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: ...
Mar 18, 2025•47 min•Season 4Ep. 116
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 . . .
Mar 11, 2025•21 min•Season 4Ep. 115
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. S...
Mar 04, 2025•33 min•Season 4Ep. 114
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 arou...
Feb 25, 2025•12 min•Season 4Ep. 113
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 . . .
Feb 18, 2025•18 min•Season 4Ep. 112
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 th...
Feb 11, 2025•23 min•Season 4Ep. 111
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.
Feb 04, 2025•48 min•Season 4Ep. 110
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 Ca...
Jan 28, 2025•29 min•Season 4Ep. 109
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.
Jan 21, 2025•43 min•Season 4Ep. 108
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.
Jan 14, 2025•29 min•Season 4Ep. 107
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 footprin...
Jan 07, 2025•52 min•Season 4Ep. 106
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.
Dec 31, 2024•14 min•Season 4Ep. 105
