Lenny's Podcast: Product | Career | Growth

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 (founder of MEA)

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Aug 3, 2025
Chip Conley, founder of Joie de Vivre hotels and the Modern Elder Academy, shares his journey of joining Airbnb at 52, becoming a mentor in a youth-driven culture. He discusses the 'mentor and intern' mindset, blending teaching with curiosity. Chip reveals how AI may benefit older workers and emphasizes that midlife can be a time of renewed purpose. He shares techniques for managing anxiety and offers insights on why our 40s and 50s can be the happiest years. His experiences highlight the power of intergenerational collaboration in the tech landscape.
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Joining Airbnb in Your 50s

  • Chip Conley joined Airbnb at 52, working with much younger colleagues and reporting to a boss 21 years his junior.
  • He adapted by embracing humility and curiosity, often feeling like the dumbest person in the room while mentoring the founders.
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Set Clear Meeting Goals First

  • Start meetings by clarifying the goals and desired outcomes to ensure alignment.
  • Return to these shared objectives during discussions to stay focused under founder pressure.
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Brain Diversity Boosts Team Success

  • Older brains excel in holistic and systemic thinking; younger brains excel in fast, focused problem-solving.
  • Combining this brain diversity creates brilliant teams that connect dots and execute efficiently.
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