Chip Conley
Hospitality Entrepreneur & Mentor at Airbnb / Joie de Vivre Hotels
Founding board member of Burning Man, board member of Esalen Institute; founded Joie de Vivre at 26 (became 2nd largest boutique hotel chain in US); joined Airbnb at 52 to mentor Brian Chesky and help the company scale its hospitality expertise.
Dimension Profile
Key Themes
Episode Summary
Chip Conley, who founded the second-largest boutique hotel chain in the US at 26 and then joined Airbnb at 52 as a mentor to Brian Chesky, shares the extraordinary experience of being an older leader inside a young tech company. He discusses the value of intergenerational mentorship, how his hospitality expertise reframed Airbnb's understanding of their product, and the reality of working for someone in founder mode.
Leadership Principles
- → At Airbnb I had to be both wise and curious, and often the dumbest person in the room — the combination of age and humility creates unique value
- → The real 'product' at Airbnb was the homes and apartments, not the software — bringing hospitality expertise reframed what they were building
- → It's great to be in founder mode; it's not as great to be working for someone in founder mode — understand both sides
Notable Quotes
"I was mentoring Brian, but he was also my boss. I was 52, the average age was 26. I had to be both wise and curious, and often the dumbest person in the room."
— On the unique dynamic of joining Airbnb in his fifties
"Isn't the product the homes and the apartments? Jobot said, 'Nope. Product in the tech industry is something different.' I just said, 'Listen, let's get some older people who are hosts in here.'"
— On bridging the hospitality-tech gap at Airbnb
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