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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)

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Aug 3, 2025

Guest

Chip Conley

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.

01:19:36

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00:00 / 00:00

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.

00:00 / 00:00

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.

00:00 / 00:00

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.

Get the Snipd Podcast app to discover more snips from this episode

Navigating Tech at 50: Embracing Change and Diversity

04:49 • 15min

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Bridging Generations in Tech

20:06 • 14min

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Fostering Curiosity and Collaboration in the Workplace

33:44 • 5min

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Curiosity, Culture, and Career Reflection

38:53 • 15min

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Embracing Aging and Purpose

53:23 • 21min

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Favorite Find and Wisdom from Hardships

01:14:09 • 3min

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Exploring Wisdom and Online Engagement

01:16:57 • 3min

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#4391

• Mentioned in 7 episodes

Learning to Love Midlife

Chip Conley

#6293

• Mentioned in 5 episodes

Wisdom at Work

Chip Conley

Chip Conley's "Wisdom at Work" explores the concept of the modern elder, emphasizing the value of experience and wisdom in today's rapidly changing world. The book challenges traditional notions of aging and retirement, suggesting that older individuals can maintain relevance and contribute significantly to society. Conley shares his personal journey, including near-death experiences and career transitions, to illustrate his points. He offers practical advice and strategies for navigating midlife transitions, fostering creativity, and cultivating wisdom. The book encourages readers to embrace lifelong learning and find purpose in their second half of life.

#53

• Mentioned in 154 episodes

Range

Why Generalists Triumph in a Specialized World

David Epstein

In this book, David Epstein examines the success of generalists in various fields, including sports, arts, music, invention, forecasting, and science. He argues that generalists, who often find their path late and juggle multiple interests, are more creative, agile, and able to make connections that specialists cannot. Epstein uses stories and research studies to show that wide sampling and late specialization can be more valuable than early specialization, especially in complex and unpredictable environments. He also discusses the distinction between 'kind' and 'wicked' learning environments and the importance of balancing specialization with range for long-term success.

#681

• Mentioned in 30 episodes

Peak

Secrets from the New Science of Expertise

Anders Ericsson

Robert Pool

This book summarizes Anders Ericsson's 30-year research on the acquisition of expertise. It introduces the concept of 'deliberate practice,' a specific learning method used by experts to achieve superior performance. The authors distinguish between different types of practice, such as naive practice, purposeful practice, and deliberate practice, emphasizing the importance of mental representations in achieving expertise. The book also addresses the misconception of the '10,000-hour rule' popularized by Malcolm Gladwell and provides practical tips for improving skills in various areas.

• Mentioned in 448 episodes

Man's Search for Meaning

Viktor Frankl

The book is divided into two parts. The first part recounts Frankl's harrowing experiences as a prisoner in Nazi concentration camps, including Auschwitz, between 1942 and 1945. He describes the inhumane conditions and the psychological and emotional struggles of the prisoners. The second part introduces Frankl's theory of logotherapy, which posits that the primary human drive is the search for meaning, rather than pleasure. Frankl argues that meaning can be found through three main avenues: work (doing something significant), love (caring for another), and suffering (finding meaning in one's own suffering). The book emphasizes the importance of finding purpose and meaning in life, even in the most adverse conditions, as a key factor in survival and personal growth.

#9442

• Mentioned in 3 episodes

Emotional Equations

Chip Conley

In 'Emotional Equations', Chip Conley presents a unique approach to understanding emotions through simple, non-numeric equations. The book offers practical strategies for managing emotions and finding happiness by focusing on controllable variables in life. Conley shares personal stories and those of inspiring role models who have applied these emotional equations to overcome challenges.

#264

• Mentioned in 58 episodes

Big Magic

Elizabeth Gilbert

In 'Big Magic', Elizabeth Gilbert delves into the mysteries of creativity, encouraging readers to live more creative and fulfilling lives. The book is divided into six parts: Courage, Enchantment, Permission, Persistence, Trust, and Divinity. Gilbert argues that creativity is an essential part of human nature and that it requires courage to accept and overcome fears. She emphasizes the importance of persistence, trust in the creative process, and the need to separate creativity from the pressure of making a living. Through personal anecdotes and insights from other artists, Gilbert demystifies the creative process and inspires readers to pursue their passions with curiosity rather than fear.

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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Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny

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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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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

To hear more, visit www.lennysnewsletter.com

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