Chip Conley: Modern Mentorship is Mutual


Life is a Festival 016:

Chip Conley (Modern Elder Academy)

Without today’s guest there would be no Life is a Festival Podcast.

Chip Conley is my mentor, my dear friend and the co-founder of Fest300, an online guide to the world’s best festivals where I once worked as Creative Director. Chip hired me in 2013 and that year he went to 36 festivals in 20 countries. Chip got his start in hospitality, creating Joie de Vivre hotels. After founding Fest300, he went on to become the Head of Global Hospitality & Strategy for Airbnb. He is on the board of both the Esalen Institute and Burning Man and has written five books including his most recent “Wisdom@Work: The Making of a Modern Elder.” His most recent venture is The Modern Elder Academy, a campus for midlife identity refreshment in Baja where this interview took place.

On the podcast we talk about Chip’s love of the “collective effervescence” of festivals. We go deep on mentorship from his first mentor, Herb Kelleher, and how to find a mentor to winding down a mentorship. We end the podcast talking about the role of the modern elder in today’s society and Chip’s creation of the world’s first midlife wisdom school.

I hope you enjoy this podcast as much as I enjoyed interviewing my mentor, Chip.




  • 4.  The Phoenix Hotel in San Francisco with David Chapelle, David Bowie, and Timothy Leary.

  • 10. Ritual at Burning Man, Bali and the Maha Kumbh Mela in India. 

  • 16. Rights of Passage and the liminal space.

  • 18. “Collective Effervesce” & founding Fest300.

  • 22. Chip’s favorite festivals.

  • 28. How Chip to became my mentor.

  • 32. How does one find a mentor?

  • 40. Who was Chip’s first mentor?

  • 44. Why would someone want to be a mentor?

  • 47. Chip becomes a “mentern” at Airbnb.

  • 51. Eldership and the world’s first midlife wisdom school. 

  • 58. Mentorship at the Modern Elder Academy.

  • 1:02. Chip and I discuss his mentorship of me and what I learned from him. 

  • 1:10. Is Chip still into festivals?

Special thanks to my rad producer Ari Andersen (Host of the Millennials Don’t Suck Podcast)

My multi-disciplinary design partner Andy McErlean

And the most delightful dj atish for the truly festive theme song: “Peculiar Colors” [Manjumasi]