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Mr. Wonderful, Bill Gates & Free Money

Big Questions with Cal Fussman

Release Date: 07/08/2025

Great Advice From George Raveling show art Great Advice From George Raveling

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...

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Billie Eilish & My Friend Phillip show art Billie Eilish & My Friend Phillip

Big Questions with Cal Fussman

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.

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Old Is New In The Age of AI show art Old Is New In The Age of AI

Big Questions with Cal Fussman

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...

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The Last Book Written By A Human show art The Last Book Written By A Human

Big Questions with Cal Fussman

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.

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If The NFL Can Overlook Shedeur Sanders, What Are Algorithms Doing To You? show art If The NFL Can Overlook Shedeur Sanders, What Are Algorithms Doing To You?

Big Questions with Cal Fussman

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...

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Jim Carrey’s $10 Million Lesson show art Jim Carrey’s $10 Million Lesson

Big Questions with Cal Fussman

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...

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First A Scam, Then The Future Of Trust show art First A Scam, Then The Future Of Trust

Big Questions with Cal Fussman

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...

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Your New Therapist: Talk To Ash show art Your New Therapist: Talk To Ash

Big Questions with Cal Fussman

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...

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De Niro And A Day Of No Regrets show art De Niro And A Day Of No Regrets

Big Questions with Cal Fussman

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.

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Mr. Wonderful, Bill Gates & Free Money show art Mr. Wonderful, Bill Gates & Free Money

Big Questions with Cal Fussman

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.

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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.