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)
2025-08-03 · 80 min · 94 entities
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Link in episode "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)": https://amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484
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Link in episode "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)": https://en.wikipedia.org/wiki/George_Tenet
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Link in episode "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)": https://en.wikipedia.org/wiki/Bill_Graham_(promoter
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Link in episode "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)": https://ted.com/talks/elizabeth_gilbert_your_elusive_creative_genius
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Link in episode "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)": https://esalen.org/
-
0.38
evidence rules-v4
Link in episode "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)": https://ted.com/talks/elizabeth_gilbert_your_elusive_creative_genius
-
0.38
evidence rules-v4
Link in episode "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)": https://illpushyou.com/
-
0.38
evidence rules-v4
Link in episode "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)": https://flyranch.burningman.org/
persons 18
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0.90
evidence rules-v4
Link in episode "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)": https://linkedin.com/in/sheryl-sandberg-5126652
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0.90
evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/George_Tenet
-
0.90
evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Bill_Graham_(promoter
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0.90
evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Maslow%27s_hierarchy_of_needs
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0.77
evidence rules-v4
Link in episode "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)": https://linkedin.com/in/sheryl-sandberg-5126652
-
0.77
evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/George_Tenet
-
0.77
evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Bill_Graham_(promoter
-
0.77
evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Maslow%27s_hierarchy_of_needs
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0.70
evidence rules-v4
Feed author/publisher: Lenny Rachitsky
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0.55
evidence rules-v4
Feed author/publisher: Lenny Rachitsky
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0.45
evidence rules-v4
Link in episode "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)": https://hyatt.com/jdv-by-hyatt/en-US
-
0.45
evidence rules-v4
Link in episode "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)": https://nytimes.com/2025/07/07/business/ai-job-cuts.html
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0.45
evidence rules-v4
Link in episode "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)": https://brenebrown.com/articles/2018/05/24/the-midlife-unraveling
-
0.45
evidence rules-v4
Link in episode "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)": https://meawisdom.com/wisdom-well
-
0.38
evidence rules-v4
Link in episode "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)": https://hyatt.com/jdv-by-hyatt/en-US
-
0.38
evidence rules-v4
Link in episode "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)": https://nytimes.com/2025/07/07/business/ai-job-cuts.html
-
0.38
evidence rules-v4
Link in episode "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)": https://brenebrown.com/articles/2018/05/24/the-midlife-unraveling
-
0.38
evidence rules-v4
Link in episode "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)": https://meawisdom.com/wisdom-well
companys 11
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0.68
evidence rules-v4
founder of Joie
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0.60
evidence rules-v4
joined Airbnb
-
0.54
evidence rules-v4
founder of Joie
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0.54
evidence rules-v4
founder of Joie
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0.50
evidence rules-v4
Feed category: Technology
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0.50
evidence rules-v4
founder of Joie
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0.50
evidence rules-v4
founder of Joie
-
0.48
evidence rules-v4
joined Airbnb
-
0.48
evidence rules-v4
joined Airbnb
-
0.40
evidence rules-v4
Feed category: Technology
-
0.35
evidence rules-v4
MEA
concepts 4
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0.50
evidence rules-v4
Feed category: Business
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0.50
evidence rules-v4
Feed category: Entrepreneurship
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0.40
evidence rules-v4
Feed category: Business
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0.40
evidence rules-v4
Feed category: Entrepreneurship
Episode description as stored
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
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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 Mildenha