Brian Chesky’s secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Chip Conley is the founder of Joie de Vivre hotels, the second-largest boutique hotel brand in the world. At age 52, he joined Airbnb as Head of Global Hospitality and Strategy, reporting to CEO Brian Chesky, who was 21 years younger. He earned the title of Airbnb’s “Modern Elder” by guiding the young founders on leadership and culture while learning Silicon Valley’s tech mindset himself. Today, Chip leads the Modern Elder Academy, the world’s first midlife wisdom school, and is the author of best-selling books like Wisdom@Work and Peak. He champions the idea that age and experience are assets—and that midlife can be a launchpad for renewed purpose and impact. *In this conversation, we discuss:* 1. The reality of Brian Chesky in “founder mode”—the good, bad, and stressful 2. How Chip went from running 52 boutique hotels to becoming Airbnb’s in-house mentor in his 50s 3. The “mentor and intern” mindset: how to simultaneously teach others and stay curious like a beginner 4. Why AI might actually favor older workers (hint: human wisdom vs. artificial intelligence) 5. His framework for navigating midlife transitions and finding meaning after 40 6. Specific tactics for older professionals to thrive in tech companies 7. Surprising data that midlife is often the happiest time of life—and how to leverage your 40s, 50s, and beyond 8. Chip’s formula for managing anxiety and fear (and how to regain control when worry strikes) *Brought to you by:* Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Coda—The all-in-one collaborative workspace: https://coda.io/lenny *Transcript:* https://www.lennysnewsletter.com/p/chip-conley *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/168435278/my-biggest-takeaways-from-this-conversation *Where to find Chip Conley:* • LinkedIn: https://www.linkedin.com/in/chipconleysf/ • Website: https://chipconley.com/ • Modern Elder Academy: https://www.meawisdom.com/ • Podcast: https://www.meawisdom.com/podcast/ *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Chip Conley (04:30) Chip’s journey with Airbnb (11:44) Insights on working with Brian Chesky (18:27) Tactics to be effective when working with founders…