In this episode of the Main Character Podcast, Keaton takes us on a trip back to his roots in Jackson, Wyoming—before the billionaires, before the resort town vibe, back when it was just a wild, rugged place to grow up. We talk through how the town has changed, what gets lost in the process of “development,” and how community identity gets tested as the cost of living climbs and culture shifts. From his college years at Texas A&M to wrestling with AI's role in our future, this one’s about the intersections of place, progress, and personal growth.

We also dig into his aviation journey—building an airplane from the ground up, navigating airworthiness regulations, and chasing the absolute joy of flight. It’s a story about curiosity, failure, persistence, and freedom. Along the way, we reflect on family dynamics, education reform, the survival skills no one teaches, and the importance of asking big questions about purpose, parenting, and what kind of world we’re building next.

Whether you’re flying high or stuck on the runway, this episode is a reminder to keep learning, stay grounded, and build something worth piloting.

Chapters

00:00 Introduction and Podcast Dynamics

02:02 Summer Activities and Outdoor Adventures

04:52 Growing Up in Jackson: A Personal Journey

08:12 The Evolution of Jackson: From Cowboy Town to Billionaire Haven

11:08 Family Dynamics and Community Connections

14:00 Cultural Differences: From Jackson to Texas A&M

16:51 The Impact of Wealth on Community and Society

19:57 Navigating Change: Development and Affordable Housing

22:52 College Experience and Career Aspirations

26:15 The Role of AI in Modern Society

29:06 Philosophical Implications of AI and Society

32:11 Future of Work and Human Purpose

35:01 Survival and Preparedness in a Tech-Dependent World

38:01 Conclusion and Reflections on Community and Change

45:55 Navigating Career Choices

50:03 Reconnecting with Emily

54:02 The Journey of Building an Airplane

01:05:46 Understanding Aviation Regulations

01:17:46 The Flight Testing Process

01:24:01 The Joy of Flying and Adventure

01:34:16 The Ideal Family Size

01:38:06 The Joys and Challenges of Parenting

01:45:09 Exploring Life's Purpose

01:54:11 Innovations in Space Exploration

02:07:31 The Flaws in Education and Financial Literacy

02:18:43 Megaphone Moment

02:20:17 Outro