179. Ryan Levesque Walked Away From a $70,000,000 Deal and Moved Into a Tent

What happens when you build the successful life you thought you wanted—and realize you want to escape from it?

In this episode, Kate sits down with entrepreneur and Return to Real author Ryan Levesque, who spent a decade building a hyper-growth company that generated more than $100 million in revenue. When a $70 million acquisition fell apart just days before signing, Ryan found himself confronting a question bigger than the deal itself: What was all of this actually for?

That question eventually led him somewhere unexpected—a tent on a farm in Vermont. Ryan shares how learning to grow food and work with his hands awakened a part of himself he’d lost, why his family sold their home and moved across the country without knowing exactly where they would land, and how they ultimately built a life centered around nature, food, family, and what feels real.

Kate and Ryan also explore the hidden cost of scale. Ryan opens up about realizing that for seven years, virtually everything published under his name had actually been written by other people—and how returning to writing his own words brought more opportunities in six months than he’d experienced in the previous six years. They unpack authenticity, cortisol as a “molecule of misalignment,” and why some of the most valuable things in life simply cannot be scaled.

This conversation is an invitation to question the endless pursuit of more. In a world increasingly filled with AI, automation, and artificial everything, Ryan makes the case that what’s real—your voice, your relationships, your body, your attention, and the ordinary moments of your actual life—may be more valuable than ever.

“It's like you get to that level of real and it becomes almost like this craving where you want real in your life.”   -  Ryan Levesque

🎤 Let’s Dive into the Good Stuff on Plenty 🎤

00:00 Escaping the Life He Built

03:42 Investing at 10 Years Old

13:00 Preparing Kids for an AI Future

22:50 The $70 Million Deal

24:59 Moving Into a Tent