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a comeback in the Age of AI, what it says about trust, choice, and control — and how sometimes the stuff we think is obsolete becomes in vogue all over again.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!

Neil Parikh, the founder of TalkToAsh.com, discusses the urgent need for mental health resources, especially during the pandemic when access to therapists became limited. The conversation highlights how AI, unlike traditional assistants, can engage with users like a therapist. Parikh shares insights into user experiences, illustrating how the app offers a stigma-free space for emotional exploration. He also touches on the balance between AI and human therapists, suggesting a collaborative future for mental wellness.

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.

The discussion kicks off with insights from Kevin O’Leary about the job losses driven by AI. A surprising encounter with a cleaning robot at a gas station raises questions about our workforce's future. The idea of Universal Basic Income becomes a hot topic, exploring its role as a safety net in an automated world. Cal delves into the concept of taxing robots, inspired by Alaska's revenue-sharing model, to support those displaced by technology. The potential benefits of equitable wealth distribution amid rapid automation are compellingly examined.