What happens when the ancient magic of theatre meets the disruptive energy of artificial intelligence? In this episode of The Tech Talks Daily Podcast, I sit down with Emmy-nominated producer and 440 Media founder Jeffery Keilholtz to unpack how AI is reshaping entertainment, licensing, and the very soul of live performance. From his time leading Broadway Licensing Global, home to thousands of acclaimed titles including Harry Potter and the Cursed Child, Jeffery brings a rare blend of creative and commercial insight to one of the most transformative moments in entertainment history.

Our conversation explores how live entertainment faces twin challenges of visibility and scarcity in a digital age. As Jeffery explains, the rise of ChatGPT has changed how people search, discover, and decide what to see, forcing a shift from SEO to AEO, or Answer Engine Optimization. Yet even as AI floods the world with abundance, theatre’s scarcity, that irreplaceable “live, local, urgent” energy, is becoming more precious than ever. Together we examine how AI can simultaneously empower and endanger creative industries, from copyright battles worth billions to the promise of smarter audience engagement and new paths to discover hidden works.

Jeffery also shares his framework for balancing technology and artistry, urging creators to stay nimble like a blade of grass. He argues that surviving this era of AI-driven disruption requires humility, flexibility, and a renewed belief in human connection. It’s a powerful reminder that the heartbeat of theatre, and perhaps of creativity itself, still belongs to people gathered together in the same room, sharing something that can never be replicated by a machine.

How do you see AI reshaping the arts and entertainment world? Is it an existential threat to creativity or the tool that will help artists reach new heights? I’d love to hear your thoughts.