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)

August 3, 2025

AI Summary

5 min read

Chip Conley joined Airbnb at 52 as head of global hospitality and strategy, recruited by Brian Chesky to mentor amid a young team averaging 26. He shares operating principles from scaling Joie de Vivre hotels, adapting to tech, fostering culture, and now running the Modern Elder Academy (MEA), a midlife wisdom school. Key lessons center on intergenerational collaboration, working under founder-led intensity, and applying crystallized intelligence in fast-paced environments.

Adapting to Tech and Founder Mode

Conley entered Airbnb without tech experience, learning product lingo while advocating for hosts as the true product—not just app buttons. Reporting to Chesky, 21 years younger, required humility, curiosity, and credibility built through a world tour visiting hosts in 20 cities. Challenges included Chesky's workaholism (e.g., 10pm meetings), Jobs-like scrutiny, and aggressive goals that stressed teams, though Conley credits Chesky's growth mindset for successes. Tactics for thriving: Align on goals upfront in meetings, limit slide decks for flexibility, and gain leverage via customer proximity.

Continue reading the full summary in the app — free to try.

Read Full Summary →

Free • No credit card required

Listen to Audio Summary Open in App

What you'll learn

1 `* (00:04) **Joining Airbnb at 52 amid young team**`
2 `* (05:41) **Working for Brian Chesky in founder mode**`
3 `* (12:30) **Intergenerational collaboration in tech**`
4 `* (21:28) **Overcoming ageism: hiring generalists and mutual mentorship**`
5 `* (42:46) **Building Joie de Vivre: culture via Maslow's hierarchy**`
6 `* (44:23) **Near-death experience and pivot to MEA**`
7 `* (57:28) **MEA's midlife wisdom and future bets**`

+ Full timestamped outline available in the app

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)

—

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

—

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