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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)

Overview

Shownote

Highlights

Transcript

Chapters

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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)

Lenny's Podcast: Product | Career | Growth

2025/08/03
Lenny's Podcast: Product | Career | Growth

Lenny's Podcast: Product | Career | Growth

2025/08/03
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

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 o...

Highlights

Chip Conley’s journey from boutique hotel entrepreneur to Airbnb’s strategic mentor offers a unique lens into leadership, intergenerational collaboration, and the evolving role of wisdom in the modern workplace. Entering the tech world in his 50s, Chip bridged the gap between youthful innovation and seasoned experience, shaping not only Airbnb’s culture but also the broader conversation around midlife reinvention. His insights into emotional intelligence, company culture, and the value of life experience reveal a compelling narrative about the power of wisdom in driving both personal and organizational growth.
00:00
Chip Conley joined Airbnb in his 50s and mentored Brian Chesky
06:56
Chip went from mentoring Brian Chesky part-time to leading global hospitality and strategy at Airbnb.
16:34
Brian Chesky has grown as a leader by applying emotional intelligence
23:14
John Q. Smith exemplified 'invisible productivity' by bringing out the best in younger colleagues.
31:57
Older workers can thrive by combining wisdom with curiosity and positive energy
43:00
Transforming a broken-down motel into the Phoenix hotel
43:57
Realizing every day is a gift after a near-death experience
46:40
Culture guides decision-making and is essential in remote work environments
58:45
A positive mindset on aging can add 7.5 years of life according to Becca Levy's research
1:04:42
Midlife is a time of increased emotional intelligence, wisdom, and life editing.
1:08:10
The speaker uses ChatGPT for inspiration and first drafts of the Wisdom Well blog
1:09:16
Despair equals suffering minus meaning, a key emotional equation

Chapters

Introduction to Chip Conley
00:00
Chip’s journey with Airbnb
04:09
Insights on working with Brian Chesky
10:35
The value of intergenerational collaboration
19:56
Addressing ageism in tech
25:57
Chip’s early career and founding Joie de Vivre
41:33
A life-changing near-death experience
43:54
The importance of company culture
46:39
The Modern Elder Academy
55:57
The upside of aging
59:21
AI in daily life
1:06:53
Lightning round and final thoughts
1:09:14

Transcript

Lenny Rachitsky: Let's paint a picture of just what it was like to join Airbnb in your 50s. Chip Conley: I was mentoring Brian, but he was also my boss. I was 52, the average age was 26. I had to be both wise and curious, and often the dumbest person in t...