Chip Conley, Founder and Executive Chairman, Modern Elder Academy (MEA)

What happens after you build the company? After the exit? After the identity you wrapped yourself in no longer fits?

In this no-BS conversation, Ryan Heckman sits down with Chip Conley, founder of Joie de Vivre Hospitality, former Head of Global Hospitality & Strategy at Airbnb, bestselling author, and founder of the Modern Elder Academy.

Chip shares how he raised $1.1M at 26 to buy a broken-down motel in San Francisco, turning it into 52 boutique hotels before selling to Hyatt. But the most pivotal chapter was not the growth. It was the unraveling. Burnout, personal loss, and a near-death experience forced him to confront a deeper question: Who am I if I am not this company?

That reckoning led him to Airbnb, where he joined as a 52-year-old mentor to Brian Chesky during the company’s meteoric rise. Together, they navigated scale versus soul, ego versus service, and what it means to lead from behind.

This episode explores the difference between knowledge and wisdom, how to reframe accountability with your team, why midlife is a chrysalis not a crisis, and how founders can move from return on investment to ripple of impact.

For founders focused on building value, this is a reminder that you are also building a life, including your own.

Chip Conley is not an investor in one or more of Rallyday Partners private funds and did not receive any cash or non-cash compensation for participating in this podcast.

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