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In this episode Connor sits down with hospitality legend and Modern Elder Academy founder, Chip Conley. From building Joie de Vivre into one of the largest boutique hotel brands in the U.S., to mentoring the Airbnb founders through their explosive growth, Chip shares the behind-the-scenes stories that shaped his career and personal transformation. He opens up about near-death experiences, midlife awakenings, and the powerful wisdom that comes from reinvention. Whether you're a post-exit founder or just contemplating your next chapter, this conversation is packed with insight, honesty, and heart.
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Chapters:
[00:00:00] Who is Chip Conley?
[00:01:45] Building Boutique Hotel Empire
[00:03:29] Near-Death Experience Changes Everything
[00:06:31] Struggles After Selling the Business
[00:08:19] Joining Airbnb as Modern Elder
[00:10:56] Wisdom Beats Knowledge Today
[00:11:51] Founding Modern Elder Academy
[00:13:32] Creating Space for Serendipity
[00:15:02] Simplifying Airbnb’s Strategy
[00:16:57] Regulation as Competitive Advantage
[00:18:28] Thinking in Decades, Not Months
[00:19:54] Rebuilding Identity After Exit
[00:21:11] Exercising Curiosity at Work
[00:23:37] Managing Visionary Co-Leaders
[00:24:55] Buying First Hotel at 26
[00:28:00] Attracting Rock Bands with Massages
[00:30:43] Why Peripheral Players Matter
[00:31:45] Leading with Emotional Intelligence
[00:33:00] Learning to Love Midlife
[00:34:30] Men and Loneliness in Midlife
[00:36:54] Building Real Wisdom Practices
[00:39:00] Team-Wide Wisdom Reflections
[00:40:30] Aging as a Growth Opportunity
[00:43:00] What is MEA Really Like?
[00:44:45] MEA’s Growing Global Community
[00:46:29] Reframing Aging and Transition
[00:47:45] Becoming a Dad at 64
[00:48:38] Where to Find Chip Online
Chip's Stuff:
Chip's Website: https://chipconley.com/
MEA: https://www.meawisdom.com/
LinkedIn: https://www.linkedin.com/in/chipconleysf/
My Stuff:
Podcast: https://www.madeitpod.com/
Website: https://www.connortomkies.com/
X: https://twitter.com/ConnorTomkies
LinkedIn: https://www.linkedin.com/in/connortomkies/
