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) · Lenny's Podcast: Product | Career | Growth summary

Key takeaways

Age diversity in the workplace can lead to brilliant collaborations between younger and older employees, enhancing creativity and problem-solving.
Being effective in a leadership role often requires aligning goals and creating an open space for honest communication.
Midlife can be a transformative period of growth, where new opportunities for engagement and purpose emerge.
The Modern Elder Academy offers resources for individuals navigating midlife transitions, promoting wisdom and meaningful growth.
AI and older professionals can coexist, with older employees bringing invaluable context and experience that AI cannot replicate.

Summary

Journey to Airbnb: Embracing Change at 52

Chip Conley shares his experience of joining Airbnb in his early fifties, reflecting on the challenges and triumphs of navigating a youthful work culture. Despite being a seasoned hotelier, Chip found himself needing to adapt to a fast-paced tech environment, often feeling like the ‘dumbest person in the room’. His unique perspective as a mentor brought valuable insights into intergenerational collaboration within the company.

Working with Brian Chesky: The Founder Mode Perspective

Conley provides candid insights into working under Airbnb's CEO, Brian Chesky. He describes Brian's intense passion for work, highlighting both the inspiring and the challenging aspects of his leadership style. Conley emphasizes the importance of aligning goals and understanding the emotional intelligence necessary for effective teamwork, especially in a tech-driven environment.

The Value of Age Diversity in Tech

The discussion pivots to the ageism often prevalent in tech industries and the untapped potential of older employees. Conley highlights the contrast between fluid intelligence of younger workers and the crystallized wisdom of older generations, advocating for the benefits of intergenerational collaboration. He shares his experiences from Airbnb where older employees helped bridge gaps in understanding, particularly relating to customer experiences.

Midlife: A Chrysalis for Transformation

Conley introduces the metaphor of midlife as a chrysalis, a transformational phase rather than a crisis. He discusses the growth opportunities during this stage and how shifts in mindset towards aging can lead to greater happiness. By comparing midlife challenges to personal development journeys, he reassures that age should be seen as an asset.

The Modern Elder Academy: Wisdom Reimagined

The establishment of the Modern Elder Academy (MEA) is a focal point of Conley's current work. MEA aims to provide a space for midlife individuals to explore transitions, creativity, and purpose. Chip emphasizes the importance of wisdom management amidst an era dominated by AI and technological advancements, positioning MEA as a nurturing environment for personal growth.

Show notes

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)

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Transcript: https://www.lennysnewsletter.com/p/chip-conley

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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168435278/my-biggest-takeaways-from-this-conversation

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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/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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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

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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/

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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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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)