Big Questions with Cal Fussman

Raveling passed away early this month at 88 after living a life shaped by being in the right place at the right time — and knowing what to do when he got there. As a boy, after losing his father and seeing his mother institutionalized, he found stability at a Catholic boarding school. That path led him to become the first African-American basketball player at Villanova … to meet coaching legend Bobby Knight … to join the U.S. Olympic coaching staff in 1984, where he met a young Michael Jordan’s and helped guide Jordan toward a Nike contract that would change sports, culture, and business forever. But Raveling’s greatest “right place, right time” moment? Standing at the Lincoln Memorial in 1963, when Dr. Martin Luther King Jr. had just finished speaking. Raveling asked for a copy of the speech — and King handed him the original “I Have a Dream” manuscript. A lesson to all of us on how to get the most out of our moments.

Billie Eilish was just 13 when she recorded the song Ocean Eyes in the bedroom of her home and her brother Finneas uploaded it to SoundCloud. Within weeks, hundreds of thousands had listened to it. That’s how one haunting voice changed pop forever. Now, Cal’s friend Phillip is a finalist for SoundCloud’s Tomorrow’s Breakthrough Artist Award. He’s not the next Billie — he’s the first Phillip. And his story will stop you cold and make you want to root for him.

Cal was ready to dump his storage bins of CDs, tape cassettes, and DVDs — until he discovered a twist: the world is racing back to the very things he was about to throw away. Parents are pulling out old DVD players so their kids can choose movies without being spoon-fed by algorithms. Taylor Swift just announced her next album will also drop on cassette. And suddenly “Old School Cal” looks like he’s ahead of the curve. In this episode, Cal explores why physical media is making a comeback in the Age of AI, what it says about trust, choice, and control — and how sometimes the stuff we think is obsolete becomes in vogue all over again.

Cal sits down with Jeff Burningham, author of The Last Book Written by a Human, to unpack the AI tidal wave about to hit classrooms, boardrooms, governments, and even religions. This isn’t doomscrolling—it’s a positive roadmap through the disruption ahead. If you want to become wise in the age of AI, start here.

The NFL passed on Shedeur Sanders — son of Deion “Prime Time” Sanders — through the first four rounds of its 2025 draft, despite the quarterback’s two electric seasons in college with Heisman trophy winner Travis Hunter. It felt eerily like the way algorithms reject qualified people in the job market. Shedeur’s notoriety and connections got him a shot . . . and his exhibition season debut with the Cleveland Browns proved doubters wrong. Here’s what his story can teach you about surviving in a world where the first gatekeeper isn’t human: Make sure you’re connected.

Jim Carrey’s $10 Million Lesson Cal has an epiphany as he’s giving one of his storytelling workshops. He’s able to tie the thought to the moment in 1985 when a down and out actor named Jim Carrey wrote a check to himself for $10 million to be cashed 10 years later when he became a film star. The $10 million did come to Carrey ten years later with the release of the hit Dumb and Dumber. Cal wonders how to visualize the most out of yourself even when you don’t believe you’re talented in a particular area. The answer applies to everyone and you might want to use it. Check out the episode.

On a sunny Sunday morning, Cal shares breakfast with friends—when a woman reveals how a shady third-party travel site jacked up her airline ticket price. It was no fluke: The company is flooded with complaints on Yelp. The story sparks a deeper question in Cal: what’s happened to trust in our time? That question is answered by billionaire investor Mark Cuban: “In three years, AI will flood us with so much fake video, we won’t know what’s real anymore. That’s why face-to-face meetings, events and jobs will explode.” Could AI be pushing us back toward face-to-face connections and a renaissance in trust? Listen up!

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 that is very different breed of AI than ChatGPT. It’s not an assistant that follows commands. It questions like a therapist and has helped many of the 50,000 people who’ve tested it. It launches today. And for now, it’s free.

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.

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.

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 collaboration. He believes AI can help us unlock our most creative selves—and shape a future that feels more like

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/half-airplane taxi service that looks like a job for the future as we head into the age of the Jetsons. Listen up and get to the cutting edge.

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… and peace.

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, leaving behind a powerful legacy of light over darkness.

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.

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 to AI – and those who don’t? This is not just a conversation about running. It’s about resilience, purpose, technology and inequality -- and what happens when they all collide. Listen now. Share widely. The world needs this story.

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 finding new professions.

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 to write The Origin of The Species. But maybe something unforgettable will come of Cal’s work that touches every life it reaches. Cal welcomes you to the next chapter of Us.

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 comeback story. It’s a masterclass in overcoming adversity, reshaping identity, and pushing past limits—no matter the odds. If you’re facing any kind of challenge, this conversation will give you strength. Share it with someone who needs hope today.

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 fear, Cal concludes. It’s the time to be curious about how to understand it, regulate it and get the most out of it.