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
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