10 Years of Why Not Now?: Amy Jo Martin & Richard Grewar on the Conversations That Changed Us (Ep 353)

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For 10 years, Amy Jo Martin has asked hundreds of entrepreneurs, creators, athletes and cultural icons one deceptively simple question: Why not now?

In this special 10-year anniversary episode of the Why Not Now? podcast, the person usually behind the scenes steps up to the mic. Longtime producer Richard Grewar joins Amy Jo to look back at a decade of conversations, unexpected moments and lessons that have shaped the show – and both of their lives.

They go back to the beginning: launching the podcast from a boat in San Diego, landing Mark Cuban as their first guest and figuring out production as they went. From there, they revisit memorable conversations with guests including Tony Robbins, Matthew McConaughey, Billy Corgan and more, along with the moments that proved some of the most powerful stories don’t always come from the biggest names.

Amy Jo and Richard also unpack how podcasting has changed over the past decade, why genuine curiosity still beats a perfectly prepared question, and what producing hundreds of hours of conversation can teach you about listening, decision-making, the power of a follow up question and knowing when not to edit out the silence.

There are stories about recording through steam trains, unreliable Wi-Fi, an RV and even a makeshift studio near the NICU. But at its core, this episode is about what happens when you keep following your curiosity – even when you don’t know where it’s leading.

Ten years later, the question remains the same.

Why Not Now?

Amy Jo Martin speaks globally on Humanizing AI, Leadership, Decision-Making, and the Future of Work. Learn more about keynote topics and availability: amyjomartin.com/speaking

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