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)

03 Aug 2025

Audio

Description

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 stressful2. How Chip went from running 52 boutique hotels to becoming Airbnb’s in-house mentor in his 50s3. The “mentor and intern” mindset: how to simultaneously teach others and stay curious like a beginner4. Why AI might actually favor older workers (hint: human wisdom vs. artificial intelligence)5. His framework for navigating midlife transitions and finding meaning after 406. Specific tactics for older professionals to thrive in tech companies7. Surprising data that midlife is often the happiest time of life—and how to leverage your 40s, 50s, and beyond8. 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/lennyVanta—Automate compliance. Simplify security: https://vanta.com/lennyCoda—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(04:09) Chip’s journey with Airbnb(10:35) Insights on working with Brian Chesky(19:56) The value of intergenerational collaboration(25:57) Addressing ageism in tech(41:33) Chip’s early career and founding Joie de Vivre(43:54) A life-changing near-death experience(46:39) The importance of company culture(55:57) The Modern Elder Academy(59:21) The upside of aging(01:06:53) AI in daily life(01:09:14) Lightning round and final thoughts—Referenced:• Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Natalie Tucci on LinkedIn: https://www.linkedin.com/in/natalietuccishoff/• Laura Modi on LinkedIn: https://www.linkedin.com/in/laurahughes6/• How to build a cult-like brand | Laura Modi (Bobbie): https://www.lennysnewsletter.com/p/from-growth-to-slowth-the-making• George Tenet: https://en.wikipedia.org/wiki/George_Tenet• Joie de Vivre Hospitality: https://www.hyatt.com/jdv-by-hyatt/en-US• Fest300: https://en.wikipedia.org/wiki/Fest300• John Q. Smith on LinkedIn: https://www.linkedin.com/in/johnqsmith/•Will A.I. Replace New Hires or Middle Managers?: https://www.nytimes.com/2025/07/07/business/ai-job-cuts.html• Burning Man: https://burningman.org/• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/• Bill Graham: https://en.wikipedia.org/wiki/Bill_Graham_(promoter)• Maslow’s hierarchy: https://en.wikipedia.org/wiki/Maslow%27s_hierarchy_of_needs• Measuring what makes life worthwhile: https://www.ted.com/talks/chip_conley_measuring_what_makes_life_worthwhile• Jonathan Mildenhall on LinkedIn: https://www.linkedin.com/in/mildenhall/• Becca Levy’s website: https://becca-levy.com/• Kabuki Springs & Spa: https://kabukisprings.com/• How positive age beliefs can support positive health outcomes with Becca Levy, PhD: https://www.ama-assn.org/delivering-care/population-care/how-positive-age-beliefs-can-support-positive-health-outcomes-becca• The U-shape of Happiness Across the Life Course: Expanding the Discussion: https://pmc.ncbi.nlm.nih.gov/articles/PMC7529452/• The Midlife Unraveling: https://brenebrown.com/articles/2018/05/24/the-midlife-unraveling/• Four Seasons: https://www.fourseasons.com/• Blue Zones: https://www.bluezones.com/• The Esalen Institute: https://www.esalen.org/• Wisdom Well blog: https://www.meawisdom.com/wisdom-well/• Elizabeth Gilbert TED Talk: Your elusive creative genius: https://www.ted.com/talks/elizabeth_gilbert_your_elusive_creative_genius• Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy• I’ll Push You: https://www.illpushyou.com/• Vuori shorts: https://vuoriclothing.com/collections/shorts• Fly Ranch: https://flyranch.burningman.org/—Recommended books:• Wisdom at Work: The Making of a Modern Elder: https://www.amazon.com/Wisdom-Work-Making-Modern-Elder/dp/0525572902• Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484• Peak: How Great Companies Get Their Mojo from Maslow: https://www.amazon.com/Peak-Great-Companies-Their-Maslow/dp/0787988618• Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age: https://www.amazon.com/Learning-Love-Midlife-Reasons-Better/dp/0316567027• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl/dp/0807060100/• Emotional Equations: Simple Steps for Creating Happiness + Success in Business + Life: https://www.amazon.com/Emotional-Equations-Creating-Happiness-Business/dp/1451607261/• Big Magic: Creative Living Beyond Fear: https://www.amazon.com/Big-Magic-Creative-Living-Beyond/dp/1594634726—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected] may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Transcription

This episode hasn't been transcribed yet

Help us prioritize this episode for transcription by upvoting it.

0 upvotes

🗳️ Sign in to Upvote

Popular episodes get transcribed faster

Other recent transcribed episodes

Transcribed and ready to explore now

3ª PARTE | 17 DIC 2025 | EL PARTIDAZO DE COPE

01 Jan 1970

El Partidazo de COPE

13:00H | 21 DIC 2025 | Fin de Semana

01 Jan 1970

Fin de Semana

12:00H | 21 DIC 2025 | Fin de Semana

01 Jan 1970

Fin de Semana

10:00H | 21 DIC 2025 | Fin de Semana

01 Jan 1970

Fin de Semana

13:00H | 20 DIC 2025 | Fin de Semana

01 Jan 1970

Fin de Semana

12:00H | 20 DIC 2025 | Fin de Semana

01 Jan 1970

Fin de Semana

Comments

There are no comments yet.

Please log in to write the first comment.

Report any issue

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)

This episode hasn't been transcribed yet

Other recent transcribed episodes

3ª PARTE | 17 DIC 2025 | EL PARTIDAZO DE COPE

13:00H | 21 DIC 2025 | Fin de Semana

12:00H | 21 DIC 2025 | Fin de Semana

10:00H | 21 DIC 2025 | Fin de Semana

13:00H | 20 DIC 2025 | Fin de Semana

12:00H | 20 DIC 2025 | Fin de Semana

Sign in to Audioscrape

Share this moment