Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school

Chip Conley, former boutique hotelier who built Joie de Vivre and later joined Airbnb in his fifties as a mentor and head of global hospitality, reflects on intergenerational collaboration, working for founder-mode leaders, and building cultures. He also discusses his near-death experience and the Modern Elder Academy, a midlife wisdom school focused on transitions and reframing aging.

01Key learnings

• When working for a founder, open meetings by aligning on the goal, what defines success, and what the meeting must accomplish, then return to those points when pushed off track.
• Build credibility with demanding leaders by getting close to customers, such as visiting hosts in their homes, so your input carries weight in product debates.
• Keep decks short and principle-focused so they still make sense when a combustible founder derails the meeting.
• Understand a company's culture before accepting a role by asking for three to five adjectives describing it and whether leaders agree on the biggest cultural problem.
• Value age diversity on teams: older brains tend to connect dots systemically while younger colleagues bring speed and focus, and both strengths are needed.
• Show up with curiosity and positive energy; people notice engagement more than wrinkles, which keeps older professionals relevant in tech.
• Frame résumé bullets as a thorny problem, the skills used to solve it, and the result, which works better in interviews than a list of roles.
• Use regret-based reflection: ask what you will regret in ten years if you don't learn or do it now, and treat anticipated regret as a catalyst for action.

02Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.