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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What was it like for Chip to join Airbnb in his 50s and work with Brian Chesky?
Let's paint a picture of just what it was like to join Airbnb in your fifties.
I was mentoring Brian, but he was also my boss. I was fifty-two, the average age was twenty-six. I had to be both wise and curious, and often the dumbest person in the room.
So it's great to be in founder mode, it's not as great to be working for someone in founder mode.
Brian assumed everybody else was going to work at the same pace and duration. His point of view is like, hey, we're having a meeting in the office tonight at 10 o'clock. You know, be there.
Everyone's talking about we gotta make the product better. We gotta optimize this button and improve conversion.
Isn't the product the homes and the apartments? Joe Bot said, no product in the tech industry is something different. I just said, listen, let's get some older people who are hosts in here.
This whole story is a really good example of the value of having folks that are older.
When you have older brains connecting the dots, younger team members being really fast and focused, it's brilliant. And people won't notice your wrinkles as much as they'll notice your energy. The
Airbnb experience led you to starting something called the modern elder academy.
So if you think about the caterpillar to butterfly journey, midlife is the chrysalis. Midlife is not crisis.
How does Chip describe the value of intergenerational collaboration at Airbnb?
I'm happier today at sixty-four than I was at forty-seven when I was going through my flatline experience.
Well, let's back up a little bit. This near death experience. Today, my guest is Chip Connolly. Chip is one of the most extraordinary and interesting people that you'll ever meet. He was a founding member of the Board of Burning Man.
What does Chip say about ageism in tech and how it’s changing?
He was on the board of the Essolent Institute in Big Sur. At 26, he started a hotel chain called Juwadaviv, which went on to become the second largest boutique hotel chain in the US. After selling it, Brian Chesky personally recruited Chip to join Airbnb to help Brian and the company transform from a foundation. Growing startup to the world's most valuable hospitality brand. After leaving Airbnb, where he was known as the Modern Elder, Chip started the Modern Elder Academy, now known as MEA, the world's first midlife wisdom school, with large, sprawling, beautiful campuses in Baja and Santa Fe. He's also written seven books, given a TED Talk, and is just a genuinely interesting and amazing human and friend.
In our conversation, we explore. How to be successful in tech as you age, what he's learned working with and for Brian Chesky, including a lot of real talk, how to build a great culture at your company, his near-death experience, and how it changed the trajectory of his life, and so much more. If you enjoyed this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of a bunch of incredible products, including Replit. Lovable, bolt, n8n, linear, superhuman, d script, whisper flow, gamma, perplexity, warp, granola, magic patterns, raycast, check our D Mobbin, and more. Check it out at Lenny's Newsletter.com and click bundle.
With that, I bring you Chip Connolly. This episode is brought to you by Great Question, the all-in-one UX research platform loved by teams at Brex, Canva, Intuit, and more. One of the most common things I hear from PMs and founders that I talk to is: I know I should be speaking to customers more, but I just don't have the time or the tools. That's exactly the gap Great Question fills.
How did Chip’s early hospitality career lead to founding Joie de Vivre?
Great Question makes it easy for anyone on your team, not just researchers, to recruit participants, run interviews, send surveys, test prototypes. types and then share it all with powerful video clips. It's everything you need to put your customers at the center of your product decisions. With a prompt as simple as why did users choose us over competitors, great question not only reveals what your customers have already shared, but it also makes it incredibly easy to ask them in the moment for fresh insights from the right segment.
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Chapters
8 chapters
1
What was it like for Chip to join Airbnb in his 50s and work with Brian Chesky?
0:00–1:04
2
How does Chip describe the value of intergenerational collaboration at Airbnb?
1:04–1:21
3
What does Chip say about ageism in tech and how it’s changing?
1:21–3:01
4
How did Chip’s early hospitality career lead to founding Joie de Vivre?
3:01–4:34
5
What impact did Chip’s near‑death experience have on his life and career?
4:34–5:22
6
Why does Chip believe company culture is critical for distributed teams?
5:22–5:56
7
How does Chip explain the upside of aging and the midlife “chrysalis”?
5:56–7:19
8
What practical formulas does Chip share for managing anxiety and fear?
7:19–1:19:32
Speakers
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