Yeah.

Um, f- we had 52 boutique hotels.

The Great Recession was quite punishing, but, uh, it was more than that.

I had a long-term relationship that was meant to end, but I was just holding onto it like a life preserver.

I had a African American foster son who was an adult who was going to prison wrongfully, and I was trying to get him out on appeal.

Um, I lost five male friends to suicide, all of them 42 to 52, all of them men, between 2008 and 2010.

And then I had an NDE.

... not a crisis, that makes you not have to almost die or whatever? Uh-

community.

Yeah, there was something in that is that in the kismet of that evening and of that summer, I still have such an affection for New York.

For that reason.

I mean, I really explored myself, explored this great city, explored culturally.

It was a fundamentally transformative time for me.

It also took me into my second year of business school at Stanford Business School, where Um, I did actually, I did go into reparative therapy and, you know, so because my dad wanted me to, and, and then I had a girlfriend, um, my second year of business school.

Well, the therapist was a famous therapist in the Bay area, in the world.

And I highly recommend anyone nearing or at or thinking they're late in midlife to go spend time with on one of Chip's retreats.

Yeah, well, I would love to know what is the Modern Elder Academy? How does it function? If you show up at one of these gatherings, what happens? Walk us through what people experience.

Even though the name won't tell you this, we've had people as young as 22 and as old as 95 come to MEA.

We're the world's first midlife wisdom school.

Average age of the person who comes is about 54.

So it's really more midlife than it is how we would think of elder.

But you can be an elder in midlife.

At Airbnb, I was, as a boomer, absolutely the modern elder.

would love to have you share just the design of that and why that was so important to the design.

heard of him.

Gavin was starting a hospitality business.

His sister felt like he was clueless.

She knew me.

She introduced him to me because I was a hospitality guy.

And seven years as a senior.

And so next thing I knew, I'm mentoring him.

Do you feel like there are people within your organization who own it enough that this whole project continues even when the force of chip is not there? Yeah.

Use as directed.

When I was feeling a little depressed and not a lot of joie de vivre, I ended up in the local bookstore around the corner from our offices.

And I initially ended up in the business section of the bookstore looking for a, a business solution.

But given my befuddled state of mind, I ended up in the self-help section very quickly.

And that's where I got reacquainted with Abraham Maslow's Hierarchy of Needs.

I took one psychology class in college, and I learned about this guy, Abraham Maslow, as many of us are familiar with his hierarchy of needs.

But as I sat there for four hours, the full afternoon, reading Maslow, I actually recognized something that is true of most leaders.

Wayfair, every style, every home.

That's pressure.

Yeah.

So, uh, he was my baseball coach, and I was the star pitcher.

He was a Eagle Scout and a Boy Scout leader, and I became an Eagle Scout.

I went to the same high school as my dad.

I played water polo there like my dad did.

Um, I was student body president of that high school like my dad was.

And that is, I think, what I'm hearing from you and so many others, is they've abandoned their own truth-for someone else's dir- you know, directives, or even directives they create themselves that no longer serve them anymore.

Anyway

... long story short is, uh, it's been, it, it led me to becoming this modern elder, and what the hell is a modern elder? So, um, the traditional elder of the past was all about reverence.

You revered your elders, but a modern elder is about relevance, and so you better be as curious as you are wise.

So at age 52, I was joining a tech company for the first time.

I didn't understand the lingo, but I had to learn, and so what I had to do was be humble.

I had to be open to, like, saying, "I don't know what you fucking mean by saying you're gonna ship a feature.

Explain that to me." And I, and so I was the person who could come in and make the bridges and create the bridges to the travel industry, and I was Brian's mentor and helping him to look at leadership from a CEO's perspective.

All the rules.

Hi, I,

uh, let's

get

you a basket.

The key to thriving in today's knowledge industry isn't just what knowledge you know, but how wisely you can apply it.

I've spent the past decade studying the value of wisdom.

And in my recent HBR article, I show how moving beyond a focus on knowledge work and embracing wisdom work helps teams to be more productive, improves employee retention, and creates a more innovative work environment.

So what is wisdom? The difference between knowledge and wisdom is that you accumulate knowledge and you distill wisdom.

[laughs] Tell me, what are some of the simple ways to make someone feel genuinely welcome, e- even in a casual setting? A lot of people, you know, the casual hang I feel like is a [laughs] is so popular these days.

The number one rule, uh, and to use another-- to use rule again is to be a great listener.

Someone will feel more comfortable when they feel like they can be comfortable as themselves in the environment in which they're being hosted.

And so what that means is to give people the comfort to be themselves.

Now, when they-- I say be themselves, it doesn't mean there's not etiquette and rules and the proper dress code, et cetera, for the-- depending upon the event.

But it does mean a person feel-- can feel comfortable in their own skin and they don't feel like they're having to pretend to be someone else.

And most importantly, it means that they feel that, that someone is seeing them and listening to them, and that listening to them is an essential piece of this, is the, the sense that somebody gets you.

[laughs] I love it.

Maybe to provide some context to it, though, let's back up for a second and talk about, in your view, what is the role of a leader? Where can a leader add the most value? What should they be doing? And where does this notion of soulfulness come into the mix?

So.

You know, a leader's job.

One of my favorite questions to ask my direct reports at the three companies that I have helped to run, which would have been Joie de Vivre, which is a boutique hotel company that I started when I was 26 and ran for 24 years.

I became the second largest in the U.S. with 52 boutique hotels around California.

And then seven and a half years as the Modern Elder to the Airbnb founders, as the head of global hospitality and strategy, but the mentor to the founders as well.

And then as the founder and executive chair of the Modern Elder Academy.

What can I do and how can I regain that feeling of meaning?

What's the point?

Yeah.

Yeah.

So, so, so when I was, uh, you, during the Great Recession when I was in my late 40s going through a really hard time, um, I lost five male friends to suicide.

Uh, and that was for ages 42 to 52.

That was in two and a half years, and they're a- all unrelated to each other.

So for me, that was my first time of like, I was dealing with death.

You do cry?

I learned so much." Just like, what was that experience like? What did you learn from working for someone like Brian?

Well, let's start with the fact that it- I would never have gone to work for Airbnb if I didn't believe in Brian.

Because quite frankly, when Brian approached me and we started talking about it, I was like, I wasn't sure I liked the, uh, the business model all that well as a hotelier.

So I had to believe in something beyond the business model, because I wasn't sure that the s-mo- the business model would work.

Although, soon after joining, I saw the numbers, I was like, "Wow, this is working pretty well." But I believed in Brian because the thing that Brian showed up with initially was just a curiosity and an appetite for learning.

You know, I remember back in 2011 when the, you know, the big debacle happened with, um, the, the apartment getting, uh, trashed by a guest, and, and so Brian decided he was gonna go to find, you know, George Tenet, the, the f- former head of the CIA.

And so, like, Geo- Brian would go to experts and, and say to the expert, "I don't know what the hell I'm doing." And, um, he did that with me when it came to hospitality.

Maybe just talk about that broadly and w- then we segue into other elements of your career.

Yeah

... is in a, in a minute.

"And I can't have that with my friends or my family members." And you know, I, what I think is true a lot of the time is that you've not outgrown your friends, you've outgrown the conversations you're having with your friends.

So the question is, how do you open that up? And one of the things I learned at, at MEA was this guy Aaron Taylor.

He was a NFL, um, uh, Super Bowl wi- role, uh, ring win- winner.

Uh, he won the Super Bowl twice with the Green Bay Packers.

Um, and Aaron was a, you know, big husky lineman.

Are there any kind of common traits or characteristics that you can identify like, "Oh, this person's gonna get it, this person isn't"?