This week’s conversation is with Chip Conley, a boutique hotel entrepreneur who helped Airbnb’s founders turn their fast-growing tech start-up into a global hospitality brand.

After selling Joie de Vivre Hospitality, the company he started as a rebel entrepreneur at age 26, Chip wasn’t sure what was next.

He could have retired at age 52 but the young founders of Airbnb came calling.

Chip served as Airbnb’s Head of Global Hospitality & Strategy for four years — while also being CEO Brian Chesky’s mentor — and continues today as a Strategic Advisor to the company’s leadership.

Chip wrote about that experience in Wisdom@Work: The Making of a Modern Elder where he shares his unexpected journey at midlife — from CEO to intern.

While writing Wisdom@Work, Chip was inspired to build the world’s first “midlife wisdom school,” the Modern Elder Academy, with a 3-acre oceanfront campus in Baja California Sur, Mexico.

So why does Chip care so much about this idea of a “modern elder?”

It’s because there were a few key points in Chip’s life where something was eating at him… he knew he wasn’t on the right path but it could have been easy to stay the course.

Chip made the difficult but necessary decision in those moments to make a change and that’s at the heart of this conversation.

This is about authenticity, it’s about being in touch with your core principles, and ultimately, it’s about wisdom.

Chip’s seen it from every angle – entrepreneur, founder, mentor, and continues to make an impact on the next generation.

“Wisdom is really about pattern recognition. The question is how do you accelerate your process of recognizing patterns? Objectively witnessing what is happening in your own life is the first piece.”

In This Episode:

  • Joined Airbnb in 2013 at age 52 and felt out of place, was scared, and almost left the company immediately
  • Was worried about protecting his ego and the idea of failing at something after he’d been successful for so long really concerned him
  • His dad reminded him that he needed to reframe that moment and figure out how he could turn his fear into curiosity
  • Following in his dad’s footsteps until he finally had the courage to make a change in college… coming out as gay
  • Where did he find the courage to come out?
  • How did he cope with hiding his true nature for so long? Being an admiration addict, an achievement addict, striving to be more and more successful
  • His process for coming to grips with who he was: the concept of attainment vs. atonement
  • The reason he started Joie de Vivre… wanting to create an environment focused on joy, not just performance
  • The framework he works from: gravitas and levity… why it’s a blessing and a curse
  • A freak accident that almost ended his life and how that ultimately changed his course thereafter
  • The wakeup call made him realize how much he’d been suffering … he defined it as “despair = suffering-meaning”
  • How he once again had the courage to make a change
  • Experiencing more moments of flow helped him with his depression… why he believes flow and a growth mindset go hand in hand
  • His favorite meditation techniques
  • Translating insights from mindfulness to the business world… the classic mistakes young entrepreneurs make
  • An important strategy in business: identifying which things are most urgent and important
  • How has he developed wisdom?
  • What it means to be a “modern elder”


Listen via: Apple Podcasts | Android | SpotifyStitcher | Pocket Casts |  RSS



“Regular check-ins with yourself, asking, ‘What did you learn this week?’ is a shorthand way of making sense and creating meaning out of what’s happening in your life.”

“Imagine five years from now in your life. What is it that most gets you jazzed and juiced up? What are we doing today to help you get there?”

“I think you could have one of three relationships with your work: it’s a job, a career, or a calling. When you have a calling there’s a very high threshold for pain.”

“Mastery is all about the love of practice.”

“Joie de Vivre (Joy of Life) was not just the mission of the company, it was what I was aspiring toward. I didn’t want to aspire toward just performance anymore. I wanted to create an environment where we created Joie de Vivre.”

“Happiness and joy are two different things. Joy is something that’s bubbling up from inside of you. Figure out where you find joy and try to put yourself in environments where you’re able to have that.”

“When you’re in flow, you feel that sense of being fully alive.”

“The thing I try to do with the entrepreneurs is to help them see first and foremost, there’s a lot of reasons that a business succeeds or fails that have nothing to do with you. And so let’s start just knowing that. This is not life or death.”


Related Episodes:

  • Finding Mastery 161: Soren Gordhammer, Wisdom 2.0 Founder, on Spirituality, Purpose, and Mindfulness
  • Finding Mastery 141: Michael Murphy, Co-Founder of Esalen Institute, on Personal Growth and Meditation
  • Finding Mastery 015: Elizabeth Lindsey, National Geographic Explorer, on Elders’ Wisdoms





Sign up for our weekly newsletter to receive the transcript to this conversation and additional premium content!


Please support our partners!!

We’re able to keep growing and creating content for YOU because of their support. We believe in their mission and would appreciate you supporting them in return!!

Click HERE for all links and codes to take advantage of deals from our partners.



Chip Conley is an American hotelier, hospitality entrepreneur, author, and speaker. Chip is the founder of Joie de Vivre Hospitality, which he began in 1987 at age 26 and held the position of CEO for nearly 24 years.