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Chip Conley, Founder at Modern Elder Academy — Using regret as fuel; how and why founders need to shift their identities; how to manage people older than you; and his favorite interview question


Rebel hospitality entrepreneur and New York Times bestselling author, Chip Conley disrupted his favorite industry… three times. At age 26 he founded Joie de Vivre Hospitality (JdV), transforming an inner-city motel into the second largest boutique hotel brand in America. He sold JdV after running it as CEO for 24 years, and soon the young founders of Airbnb asked him to help transform their promising start-up into the world’s leading hospitality brand. Chip served as Airbnb’s Head of Global Hospitality and Strategy for four years and remains the company’s Strategic Advisor for Hospitality and Leadership. Chip is the founder of the Modern Elder Academy (MEA), where a new roadmap for midlife is offered at a beautiful oceanfront campus in Baja California Sur, Mexico, and forthcoming campuses in Santa Fe, NM. His five books have made him a leading authority at the intersection of psychology and business. Chip was awarded “Most Innovative CEO” by the San Francisco Business Times, is the recipient of hospitality’s highest honor, the Pioneer Award, and holds a BA and MBA from Stanford University.

Chip had tons of wisdom to share in this talk, including how to use regret as fuel for the future, what founders can learn when they shift their identities, how to manage people older than you, what Chip learned from the people that he mentored, and his favorite interview question.

Let’s tap into some of his wisdom.

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Key highlights in this episode

Know our guest; Chip Conley (00:30)

The identity cleanse and why it is important (03:19)

Chip’s near-death experience and how it made him shift his identity when he sold his company (07:30)

The Anatomy of a transition; Three stages of transition (14:48)

How Chip became a mentor and an intern to Airbnb Co-Founder&CEO Brian Chesky (18:46)

Using regret as raw material for the future (19:45)

How insights from Airbnb led him to start the Modern Elder Academy (21:55)

Ways of scaling your company’s culture & soul as the company grows (26:46)

Culture fit vs. Culture add approach to hiring (28:48)

His favorite interview questions (31:20)

Why Chip has developed a strong personal brand and how it has served him (37:55)

His advice to new founders who about having a personal brand (41:06)

What Chip teaches his mentees (46:37)

What he has learned from his mentees (51:10) 

How to manage people older than you. And how to operate in an environment where your boss is younger than you (56:18)

Ways through which founders can find the truth in their companies (1:01:30)

The adjustments Chip has made in his leadership style and the feedback he received (1:04:13)

What Chip wishes he had known earlier on his entrepreneurship journey (1:08:11)

His advice for other founders as they embark on their journey to grow into leaders (1:09:41)

Notable Quotes

  • “A regret is not a bad thing as long as it makes you wiser.” (20:47)
  • “One of the most important things any kind of leader can do is to articulate a leadership perspective of what it means to be a leader.” (38:24) 
  • “You can’t be an open-door leader with a closed-door mind. Just because you have a slogan doesn’t necessarily mean your behaviors embody that slogan and doesn’t necessarily mean that slogan, which is a cliche is really the best definition of how you show up as a leader.” (42:08) 
  • “Wisdom is metabolized experience that leads to distilled compassion.” (57:04) 


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Resources Mentioned

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