Brian Chesky's 52-year-old mentor who scaled Airbnb (after dying 9 times and building a hotel empire) | Chip Conley (founder of MEA)

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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)

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/

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 in founder mode

(21:08) The value of intergenerational collaboration

(27:03) Addressing ageism in tech

(31:18) Advice for thriving as an older individual in tech

(35:01) Advice for hiring managers

(42:37) Chip’s early career and founding Joie de Vivre

(44:12) A life-changing near-death experience

(47:51) The importance of company culture

(52:20) The Peak Model

(57:09) The Modern Elder Academy (MEA)

(01:00:30) The upside of aging

(01:06:43) Who MEA is for

(01:08:05) AI in daily life

(01:10:20) 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

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Lenny may be an investor in the companies discussed.

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My biggest takeaways from this conversation: