-I like to ask questions at cocktail parties where I say, like, "So what are you a beginner at these days?"

And people look at me like, "What are you talking about?"

[ Laughs ] There's a guy named Peter Drucker, famous management theorist.

And he had a practice that every two to three years, he would study something new that had nothing to do with being a business school professor.

And he felt like that curiosity was an elixir for his life.

And, you know, the man lived till age 94.

He wrote two-thirds of his 40 books after the age of 65.

So there's no doubt in my mind that learning how to be curious and a beginner again, it's sort of its own form of a fountain of youth.

[Clapboard snapping] -Where were you when you came into this world, and what was that environment like for you as you were a young person?

-So, I was born in Orange, California, I say in the shadows of Disneyland.

I was born in 1960, and Disneyland had just opened.

And, you know, it was sort of a robust, optimistic world I grew up in, in Long Beach, California.

I was the first of three kids, the only boy to my parents, Steve and Fran, who were both firstborns.

So I was the firstborn of two firstborns, so that -- [ Laughs ] That meant I was gonna be somebody who was gonna have a lot of responsibility and be pretty type "A."

[ Laughs ] And that's sort of how I grew up.

But I really was an introvert when I was young and then became an extrovert as a teenager.

-And can you tell us a little bit about Steve and Fran?

-My father was a tough guy and is a tough guy.

He's 86.

We're very close today, But, man, I was sort of scared of him when I was growing up.

He was a Marine captain in the reserves and very conservative and sort of -- Yeah.

He was a macho dude.

And my mom was quieter, very conservative, also, and she was an elementary school teacher until she had me.

And she became just sort of the classic, you know, 1960s homemaker.

And in many ways, with the '60s being as tumultuous as it was, I sort of felt like I lived in this bubble in the '60s and early '70s, in a very suburban, generally white, middle-class community.

-How did that feel to you, to have a dad that was so strict and conservative?

-You know [sighs] it was hard to have a dad that was as demonstrative as my dad was.

And I was, also, Stephen Townsend Conley Jr., so I was the chip off the old block.

My dad was my baseball coach.

I was the star pitcher.

My dad was the scout leader and an Eagle Scout.

I became an Eagle Scout.

I went to the same high school as my dad, played water polo and swam there just like him.

I went to Stanford University, where my dad went.

[ Chuckles ] I joined a different fraternity than my dad was in.

[ Laughs ] I was a rebel!

But to be honest with you, I spent most of my, you know, teen years and early adulthood trying to be a better version of my dad.

And it wasn't until I was 22 years old, living here in New York in 1983, that I, on Independence Day, really broke free from the -- And liberated myself from trying to be a better version of my dad.

-How did you do that?

-Well, I did that -- I had been dating women during high school and college, but also knew that I had -- I was, you know, in love with my best friend, who I played water polo with.

And we went to high school and played water polo at Stanford.

And long story short is I, on Independence Day 1983, I walked from 86th and Riverside, which is where I was living for the summer, working for Morgan Stanley investment bank, and I walked down to the Village and walked into a bar called Uncle Charlie's -- sort of infamous place.

I really didn't know where to go.

I hadn't done any research.

And when I walked inside, my black-and-white world went into Technicolor, and I realized, "Oh.

Okay.

This is where I'm supposed to be."

And met somebody that night.

I was 22.

He was 19 -- Victor.

And had a summerlong romance.

So I was doing Morgan Stanley, cigars and suspenders during the day, and going out dancing with my Puerto Rican boyfriend at night.

And it was a very unusual summer.

I loved it.

But I had to go back to California and come to grips with the fact that this was news was not gonna be well-received by my dad or a lot of the people I grew up with and a lot of the people I was in business school with.

My father's initial reaction was very considerate, actually.

But within a week, he was worried that I was gonna become a florist and a hairdresser.

Truly, truly.

These were his words.

And I love my dad.

I love my dad so much.

But his biggest worry was that I was gonna lose my ambition, you know, which is what happens with a firstborn born to two firstborn, is like, "Okay.

You know, where does your ambition go?"

I said, "Dad, I'm still ambitious.

There's still a lot I want to do in the world."

-Okay.

So, you get to Stanford.

What are some of your interests early on at Stanford?

-So, I got to Stanford, and I was playing water polo on the national champion water polo team.

So [chuckling] a lot of my time was doing that.

I was fascinated by politics.

And so between my first and second year of college, I went to D.C.

and worked for a congressman there.

So politics was an interesting thing for me in my freshman year.

By my second year in college, after I came back from Washington, D.C., I was like, "I'm not going into politics."

[ Laughs ] And I started focusing a little bit more on business.

Stanford didn't have a business degree, but I started studying economics and started working for my uncle, who was a very successful real- estate developer and broker, commercial real-estate developer and broker in Silicon Valley.

And I did well, you know?

But I also felt very much like I'd just taken all my fraternity brothers and put them in an office.

And they were 10 or 15 years older than me, and they were all trying to one-up each other in terms of who had the best BMW, and it really didn't work for me.

I liked my business-school classmates individually, but as a group, it felt a little bit like they were, I don't know, conventional and conformist and type "A."

And so I think I was looking in the mirror.

[Laughs] And I was having a hard time looking in the mirror, this is who I could be two, four, six years from now, because they're all older than me.

And yeah, didn't like it.

Came to New York, working for Morgan Stanley's real-estate division.

And that's the summer I came out and went back to my second year of business school.

And I was like, "I can be a rebel.

You know what?

I want to be somebody different at business school."

And, so, in my second year of business school, I decided I was gonna go work for a commercial real-estate developer in San Francisco, because I liked the idea of living in San Francisco.

And instead of taking $100,000 a year offer from Morgan Stanley, I was gonna take an offer at $24,000 a year, which is ridiculous for someone graduating from Stanford Business School, even in 1984.

But 2 1/2 years later, I was bored, and I wanted to do my own thing.

And that's when I decided to start my boutique hotel company at age 26.

-Tell me about that.

-So, I'd gotten to know a guy named Bill Graham.

Bill Graham was a famous concert promoter in San Francisco and all over the world, but he was based in San Francisco.

And he said to me one day -- We were looking at doing a project with him, with the developer I was working for.

And he said, "Hey, sonny, you know what San Francisco really needs?

It needs a rock-and-roll hotel.

And I said, like, "Okay.

I'll work on that."

[ Chuckles ] And so I went to the C.E.O.

of the development company and said like, "Hey.

How about if I go out and look for that?"

And he was like, "No way.

We don't want to be in the hotel business."

So I decided to go look for it myself, and I found a broken-down motel -- pay-by-the-hour motel in the Tenderloin of San Francisco and on an acre of land, 44 rooms around a pool and with a restaurant facing the pool.

It was terrible.

It was in bad shape.

The biggest corporate account was Vinnie and his girls.

And, I mean, it was very much -- It was the kind of place that people went on their lunch hour.

And it was for sale for almost no money.

And so I decided I was gonna buy it and raise some money to buy it.

And I did.

I was 26 -- I just turned 26.

I went out and started this hotel.

Called it The Phoenix.

You know, rising from its own ashes.

It's sort of the unofficial mythological bird for San Francisco because of the 1906 earthquake and fire.

And I called the company Joie de Vivre, because I liked the idea that the mission statement of the company, creating joy, was also the name of the company.

Joie de Vivre means joy of life in French.

And at age 26, I was the C.E.O.

of a small boutique-hotel company that ultimately grew into the second-largest boutique-hotel company in the United States.

24 years later, when I sold the company, we had 52 boutique hotels around California, and I'd grown that little company from one person -- me -- to 3,500 people.

But my late 40s, toward the end of that time, I was miserable.

-What happened in that later period?

-Yeah.

So, for so much of the time of the 24 years I was running that company as C.E.O., Joie de Vivre described me pretty well.

I was pretty joyful.

I enjoyed being a leader.

I enjoyed running this company.

I felt really lucky, again, as a gay C.E.O., that boutique hotels are very design-oriented and I have a pretty good design eye.

They are very much about service and being empathetic and understanding people.

I'm pretty good at that.

They're very much about being creative about marketing.

So all these things that actually, in some ways, I felt like I wouldn't want to show the world, because it might show me as being sort of a weird creative dude, I could do those things.

And so I loved it.

But in my late 40s, at that point, I'd written three books.

And my books were doing well, and people were enjoying them.

And I was enjoying writing them.

And so in my late 40s, I was like, "Okay.

I got to figure out a way to maybe spend more of my time just writing books and going out and giving speeches and being a bit of a, you know, what's called today a "thought leader."

And, so, in that time, I was sort of mentally starting to check out from being C.E.O., because I was also a little bored, and I was, also -- I started the company for creativity and freedom.

By the time, we had 3,500 employees in 52 hotels and lots and lots of different owner groups or partners that we were responsible for.

My job was pretty stressful.

And we had the dotcom bust and 9/11 in California, especially the Bay Area, in the early part of the new millennium.

And, then, just a few years later, we had the Great Recession.

And so I had, like, two once-in-a-lifetime downturns in the same decade.

And so in my late 40s, at a time when I really wanted to go and just have some freedom to go write and be creative, I felt like I was stuck in with a seat belt on a rocket ship.

Or it wasn't even a rocket ship.

It was -- Yeah, a rocket ship that was actually about to crash into Earth.

And I didn't have any way to get out of it.

So there was that, so I felt -- And, you know, I didn't take a salary for three years.

I was running out of cash.

You know, I'd taken four mortgages on my home.

I mean, like, it was not a good time.

I had a long-term partner who was trying to end the relationship during that same time.

I lost five male friends age 42 to 52 to suicide between 2008 and 2010.

And then I had a flatline experience.

I got a bacterial infection in my leg because I had a cut on my leg, and that went septic.

And so I was put on an antibiotic that was strong and that I was allergic to.

And so right after giving a speech one day, on crutches with a septic leg [chuckles] and an allergic reaction going on.

I was signing books, and I, like, went unconscious in my chair.

And they put me on the ground, and paramedics showed up, and I came to, and they put me on a gurney.

And that was the first of nine times that I flatlined.

I died.

I sort of died 9 times in 90 minutes.

And that was a real wake-up call for this hotelier to say, "You know what?

You don't have to do this anymore."

I sort of felt like I had to -- I had obligation to stay, you know, in that seat belt, you know, just like, "I'm not leaving."

And I realized, "Man, if I'm gonna die, you know, tomorrow or today or whenever, is this how I want to live my life?"

And I really was able to see that I didn't want to live my life that way.

And as I was in the hospital, interestingly enough, I had a book that I love, one of my favorite books of all time in my day pack, you know, when I was there giving the speech.

And it's, you know, Viktor Frankl's book "Man's Search for Meaning," about being in a concentration camp and who lived and who didn't and how do you find meaning in the worst of times.

And so here I am for two days in a hospital as they're trying to figure out what was wrong with me, reading a book about this man being in a concentration camp.

And I realized that I was in my own prison, and the prison I was in was this prison of my identity and my ego.

I was really struck by these three sentences from Viktor Frankl.

And they are, "Between stimulus and response, there is a space.

In that space is your power to choose your response.

And in your response lies your growth and your freedom."

So what I take from that -- and I think it's maybe the three most powerful sentences I've ever read -- is that when things go off the rails in your life, you don't have to react.

You can create a response, create some space.

In that space, you have the power to choose your response.

And, then, in your response lies your growth and your freedom.

So at the bottom of the Great Recession, I sold my company.

Didn't make a ton of money.

But it made enough to be okay.

And I was ready for what's next.

And so I ended up writing a book called "Emotional Equations" that became a New York Times best-seller.

So I was like, "Okay.

Yep."

You know, I mean, I've had best-sellers before, but never a top-10 New York Times best-seller.

And that was a big deal.

I was a founding board member of the Burning Man nonprofit.

And, so, I've always been fascinated by festivals, so I started something called Fest300, this festival website, and went to 36 festivals in 16 countries in a year.

So, in my early 50s, all of a sudden I was like, "Wow!

I have freedom."

So I was sort of in this place of like, "I don't know what's next for me, but I just want to go out and have some joyous time."

'Cause I hadn't felt a lot of joie de vivre in the last few years running my company.

And, then, out of the blue, I got a call from a guy named Brian Chesky.

This was in early 2013.

And I really didn't know much about his company.

His company was called Airbnb.

And they were a tiny tech startup.

The hospitality industry knew nothing about them.

But they were growing pretty quickly globally, more so in Europe than anywhere.

And they were based in San Francisco.

Their headquarters was just 12 blocks from my home.

And he called me, and he said, "You know what?

How would you like to democratize hospitality?"

And I said [chuckling] "Who are you?"

[ Laughs ] And he told me who he was.

And, then, he came over and spent four hours in my backyard, and we just hit it off.

And I realized, "You know, I want to help this guy.

I want to help what they're doing.

I know they're controversial.

They don't have a clue about the travel or hospitality business, and they're gonna piss a lot of people off along the way, because they're a disrupter."

And there's a lot to the business that I think -- You know, one of the things that helps as you get older is you can sort of see the future a little bit better.

You are not so focused -- When you're young, your brain's -- You know, it's called fluid intelligence.

It's very fast and focused.

As you get older, you have crystallized intelligence.

You can sort of see around the corners, and you're better at sort of connecting the dots and thinking holistically and synthetically.

And so in many ways, they needed somebody who could be that.

And I joined, and they called me "the modern elder."

I didn't like that so much.

But, you know, the truth was I was 52 years old.

The average age in the company was 26.

And, then, they said, "Chip, a modern elder, is someone who's as curious as they are wise.

And what we really like about you is how curious you are.

The wisdom we expected, the curiosity we didn't."

And I spent 7 1/2 years there as really the in-house mentor to the founders, but, also, the head of global hospitality and strategy, taking the company almost up to its IPO.

I was like the Secretary of State.

That's what Brian called me.

"Chip, we've got problems with the mayor in Paris.

Why don't you go over there?"

And I was just, you know -- There are other people in the company doing all kinds of other great things, too.

But I had a role that was sort of unique in the sense that I was perceived as this sort of senior entrepreneur and leader.

And I loved it.

I loved it because I was a mentor.

I was a mentor and an intern at the same time.

I was learning as much from these millennials as they were learning from this baby boomer.

And, so yeah, it ultimately led me to writing a book called "Wisdom @ Work: the Making of a Modern Elder," which I started writing in Baja, down in Mexico.

One day, I went for a run on the beach and I had a Baja aha.

My Baja aha, my epiphany, was where are the midlife-wisdom schools?

Where are the places where people can learn how to reimagine and repurpose themselves, whether it's professionally or personally or spiritually, whatever.

I mean, the reality is midlife -- our 40s, 50s, and 60s -- are a ripe time for change.

And yet all we know about midlife as a culture is the idea of the crisis.

And I started thinking, "Well, maybe it's not a crisis.

Maybe it's a chrysalis.

Because midlife for the butterfly is that cocoon where it's dark and gooey and liminal, but it's also where the transformation happens."

And, so, knowing that I had lost five male friends to suicide during the Great Recession -- that was also another reason that I just felt very committed to this.

And, you know, probably stupidly, I called it the Modern Elder Academy, because that's what they called me at -- And I say it's stupid because people hear the word "elder," and they think, "Oh, it's for people in their 80s and 90s."

It's like, "No.

That's elderly.

Elder is -- You know, Tom Brady was an elder in the NFL at 42.

And if you're a fashion model at 35, you're an elder.

And at 30, if you're a Silicon Valley software engineer, you're probably an elder at 30.

So elder is a relative term.

And I just wanted to bet on that, and so MEA became a thing.

And we've had 5,000 people from 48 countries come to our Baja campus to experience this midlife-wisdom school and how to reframe our relationship with aging and navigate transitions and cultivate purpose and learn how to own our wisdom.

And so it's been a beautiful experience.

And we've just opened our second campus, a 2,600-acre regenerative horse ranch just outside Santa Fe, New Mexico.

So there is definitely a need for this.

And yeah, it's really the third chapter in my career, and each chapter being a bit of a pioneer -- one of the first boutique hoteliers, you know, going into home-sharing when nobody knew what that was and now creating a midlife-wisdom school and really helping people to understand what longevity travel is about, the idea of traveling for an experience to help you live a happier, longer life.

We call it long life learning, how you live a life that's as deep and meaningful as it is long.

And yeah, I'm loving it.

-So, in your latest book, "Learning to Love Midlife," you write, "Your wounds contain your wisdom."

What are some of your wounds that created wisdom?

-Yeah.

I like to say that our painful life lessons are the raw material for our future wisdom.

And what I mean by that is that, you know, the raw material of wisdom is your experiences.

And if you can metabolize those experiences, digest them in such a way that you can see the lesson in them, you become wiser.

So it doesn't mean a 70-year-old's wiser than a 30-year-old.

If the 30-year-old's better at metabolizing their experiences and the 70-year-old hasn't learned anything from their experiences, the 30-year-old might be more wise.

For me -- wow.

I've learned so many lessons along the way.

I see cancer with a big capital "C" as like a spiritual teacher, something that I'm supposed to learn from.

And so when I first got the news almost six years ago that I had just stage one prostate cancer, "Oh, okay."

You know, it was scary, because, like, the big "C."

But I was like, "Okay, stage one.

Not too much to worry about."

And it's prostate cancer.

You know, even though prostate cancer is the number-two cancer killer of men in the United States.

But, you know, a lot of men have prostate cancer and it tends to move slowly.

But it went to stage two and then went to stage three.

And so I've gone through quite a journey and had a lot of time in hospitals.

And, you know, I'm on hormone depletion therapy right now, so I have 1% to 2% of my normal testosterone.

So my voice is a little weaker.

My energy is a little bit weaker.

So, the cancer's taught me a lot.

Cancer's taught me to be in the moment.

Cancer is sort of like doing the same thing over again as the divine intervention of my flatline experience.

How do I slow down?

How do I appreciate things in my life that if I were not to spend time doing that now, that I would regret.

And so learning how to be less of a hero and really delegating more in the company is a lesson that I'm continuing to learn.

Yeah, and just taking care of my body.

I mean, I have not gone crazy.

Like, you know, but I'm thoughtful about how to take care of this rental vehicle that I was issued at birth and know that, you know, at the end of the day, it matters a lot more what it feels like on the inside than when it looks like on the outside.

But, you know, so, I focus on my health and my body, not for short-term vanity, but more for the long-term maintenance of the vehicle.

And so those have been some of my lessons.

And I've been very public about them.

I have a daily blog called Wisdom Well.

It's on the MEA website, as well as my own personal website.

And yeah, on a daily basis, I'm writing about this stuff.

And, you know, it's been hard for my parents who don't -- You know, my parents are still living.

They're 86 years old.

I'm 63.

And my parents have a hard time seeing me as like, "Who -- Where did you come from?"

We are a very private family.

We do not talk about our emotions and our feelings and our foibles.

And, like, "Why are you talking about, you know, pooping in your pants and things like that, I mean, like, on the way to the hospital?"

I'd be like, "Yeah.

You know, what does it feel like to have radiation?

And what does it feel like to have your prostate taken out?

And what does it feel like to have 1% or 2% of your normal testosterone levels?"

So, you know, I'm doing my best to be a poster child for why there's value in talking about it.

-You mentioned earlier Viktor Frankl's book, "Man's Search for Meaning."

There's another quote that you sometimes reference that is related to what you're saying, is Erik Erikson's "I am what survives me."

-Yeah.

I love Erik Erikson's eight stages of adult development that came from the mid-20th Century.

And he said that, you know, midlife and beyond the most important stage -- the most important thing to think about is "I am what survives me."

And that suggests legacy.

And it doesn't have to be your name on a building or a book you've written.

It literally could be the fact that you have a dog park in, you know, your neighborhood park or that you are a mentor to somebody that made a difference to them.

And, you know, learning to move from ego to soul is I think part of the experience of midlife.

And so I love that statement, "I am what survives me."

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