The Tim Ferriss Show - #374: Chip Conley — Building Empires, Tackling Cancer, and Surfing the Liminal

Episode Date: June 20, 2019

"The question would be: 'What mastery can you offer?' So have a friend of yours ask that question of you five times, and you'll be sort of surprised at, by the fifth time you get asked that question, and you've had to come up with four other answers before that, what kind of revelation you may have in this archaeological dig." — Chip ConleyAt age 52, after selling the company he founded and ran as CEO for 24 years, rebel boutique hotelier Chip Conley (@chipconley) was looking for a new chapter in life. Then he received a call from the young founders of Airbnb, asking him to help grow their disruptive start-up into a global hospitality giant. He became their head of global hospitality and strategy.Chip is a leading authority at the intersection of psychology and business. He is a New York Times bestselling author, and his latest, Wisdom @ Work: The Making of a Modern Elder, inspired him to build the world's first midlife wisdom school. Located in Baja California Sur, the Modern Elder Academy provides the place and the tools to start reframing a lifetime of experience for what comes next.Click here for the show notes for this episode.***If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!For show notes and past guests, please visit tim.blog/podcast.Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissFacebook: facebook.com/timferriss YouTube: youtube.com/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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that you'd dig it a lot and you can, of course, easily subscribe any time. So easy peasy. Again, that's tim.blog forward slash Friday. And thanks for checking it out, if the spirit moves you. Welcome to another episode of The Tim Ferriss Show, you sexy little kittens, you clever makers, and everyone in between. My guest this episode is Chip Connolly. So who is Chip? Chip and I have known each other for a very long time. At age 52, after selling the company he founded and ran as CEO for 24 years, Rebel Boutique Hotelier, that's Chip, Chip Conley was looking for a new chapter in his life. Then he received a call from the young founders of Airbnb, you may have heard of it,

asking him to help grow their disruptive startup into a global giant. He became their head of global hospitality and strategy. Chip is a leading authority at the intersection of psychology and business. He has some fantastic stories. He has a lot of battle scars and a lot of life lessons to share when we dig into a lot of all of that in this episode. He is a New York Times bestselling author and his latest, Wisdom at Work, subtitled The Making of a Modern Elder, inspired him to build the world's first midlife wisdom school. Located in Baja, California, Sur, the Modern Elder Academy provides the place and the tools to start reframing a lifetime of experience for what comes next. You can learn more about that at modernelderacademy.com, and you can learn all about Chip

and say hi to him on social media at Chip Conley on Twitter, Chip Conley author on Facebook, and Chip Conley SF on LinkedIn. So without further ado, please enjoy my wide-ranging conversation with Chip Conley. My friend Chip, welcome to the Tim Ferriss Show. I'm so happy to be here! So we've known each other a long time. And it's so nice to see you again. And I'm thrilled that we were able to coordinate uniforms with our respective tailors.

We will be busking downtown Austin later today for change. Where you are a new citizen. Yeah, I love it. Yeah, it's a beautiful town. Yeah, I love it. Yeah, it's a beautiful town. Yeah, it really is. And I thought we would start, and this may seem somber, but since this is something we were just catching up with

maybe an hour ago over lunch, can you talk about your current medical state of affairs, if you wouldn't mind? Because I think it's a wedge that leads us into discussions that can be pretty far ranging. Sure. If you wouldn't mind. No, no problem at all. On the second day of a book tour five months ago, the day before, I was at a TED speakers dinner, it's the day before giving a TED talk, I found out I have intermediate stage prostate cancer. And it came as a complete surprise. My urologist had said, after doing a

biopsy, probably a 20% chance you've got a problem here. But as it turns out, I had a problem. And so since then, I've had a few different tests. And the good news is i'm right on the cusp of serious versus sort of not not serious and so so far we've just looked at the alternative health approach but i'm all about western medicine when i need to bring the cavalry across the plantation to to sort of say yes you know probably i'm young enough i'm 58 probably gonna live another 30 to 40 years probably will have my prostate taken out in the next couple years. What does that feel like to you to realize or to say?

And what does that, for people who may not know, what does that mean? I mean, is prostate like an appendix, you don't really need it? Well, it does have certain functions, which we can get graphic and get into if you want to. But let me say, first of all, the big C, the cancer word is like, what? I have cancer. And the good news is prostate cancer, as cancers go, is actually a relatively tame cancer. But that was hard. And then prostate,

you know, the prostate, women don't have a prostate, men do. And it's part of, it has a little bit to do with sexual functioning. Actually, it's more to do with actually the secretion that happens in semen. So if you have your prostate taken out, you're no longer going to ejaculate. It does mean you still could potentially have an orgasm, but you just will have a dry orgasm. This is really crazy to be talking about this in the first five minutes. This is like the mirror in the front cover, naked nanny or something like that.

We're skipping the foreplay. This is how we keep you on the podcast for an hour and a half. So all I can say is cancer can be a teacher. And for me, it's been a reminder of the vulnerability that we can have, as well as what level of control you do have over your body. And so the fact that I've been sort of focusing on making myself healthier, and so far until a couple days ago, the test results had looked really good. Now there's a test result, a PSA score

that shows that it's spiked a little bit. So we'll have to sort of see with an ultrasound this next week. But I think more than anything, it just forces us to ask ourselves, or forces me to ask myself, what am I here on this earth to accomplish and to experience? And it creates a certain

level of urgency in life. I had a flatline experience where I went to the other side 10 and a half years ago, and that did the same thing for me. So- That was in St. Louis. That was in St. Louis. Thank you for the memory on that one. Yes, it was in St. Louis. And I had been going through a difficult time and had a broken ankle from a bachelor party with Gavin Newsom. And I had a cut on my leg, which had a bacterial infection in it because Gavin had his bachelor party at 18D Ballpark

where the San Francisco Giants play. And I hit a triple out to the outfield and slid into third base and broke my ankle, but got fertilizer in my leg on the cut. I didn't know. And so I've had a couple experiences of just being a wake-up call, which is an interesting term for a hotelier, to have a wake-up call and sort of say, you know what?

You are still alive, but are you living your life the way you want to live your life? And the reason I thought this could be as good a place as any to start is that in all my interaction with you from the very beginning, which goes back at least 10 years, probably more, I've been struck by how aware you strive to be of your thinking and how many times you have changed chapters very deliberately. And so I thought this could be a segue into conversations about some of those chapter changes and how you thought through them, and also just impactful periods in your life. Yeah. And I thought maybe if you're willing to, I think it was a quote,

I could be getting this wrong, so feel free to fact check, but the Shakespeare quote, that you shared when we were having lunch, which I think- It's beautiful. It's appropriate here. The meaning of life is to find your gift, and the purpose of life is to give it away. Now, it's been actually sometimes been called Shakespeare, sometimes called Picasso. Picasso has a great quote, too, that relates to modern elder, which is, computers are useless, they only give you answers.

We'll come back to that one. But yeah, the idea of finding your gift, the meaning of life is to find your gift, the purpose of life is to give it away. And I think that's been very much embedded in my heart and the soul and my mind over my 35, 37 years of being in the business world. And for people who aren't familiar with Chip, what is the introduction, the context you'd like to give? Or if it's easier, how would someone introduce you at a speaking engagement? Well, the way they introduce me at the speaking engagements often is,

this is the guy who's disrupted his favorite industry twice. And that industry happens to be hospitality. I was one of the first boutique hoteliers along with Ian Schrager and Bill Kempton. I started a company called Joie de Vivre. Joie de Vivre was based in San Francisco, created 52 boutique hotels, second largest boutique hotelier in the US. And then after 24 years of running that, soon after I had my Flatline experience, which was a wake-up call to say, I didn't want to be running that company anymore. I was asked six years ago by the three young founders of Airbnb to come join

them and take their little tech startup and turn it into a global hospitality brand. So I have been a disruptor twice. And yeah, so I've also written five books. And I most recently have created the world's first midlife wisdom school called the Modern Elder Academy. And we're going to talk about all of this. Yeah. So many places to go. I thought we would start with one of your more glamorous periods. Tell us how you got into commercial real estate.

You know, I grew up in California. Everybody in California has sort of like the real estate? You know, I grew up in California. Everybody in California has sort of like the real estate bug. And I went to work for my uncle the summer and then almost most of my junior year at Stanford. He was a commercial real estate developer in Silicon Valley. This was 1980. It was full of orange groves. Silicon Valley was nothing like it is today. And I just saw everybody making money and sort of having a good time in commercial real estate. What I was fascinated by was the creative side of it. How do you design environments? And ultimately, I went to Stanford Business School straight out

of undergrad and focused on real estate there. And then went to work for a real estate developer in San Francisco for a couple of years. That was after Stanford Business School. That was after Stanford Business School. And then that's when I said, you know what? The part of real estate that's really interesting is hotels. What did you think you were going to do as an undergrad? Did you know real estate was the answer? Let's say freshman, sophomore year. What did you envision adult chip doing?

I thought I was going to be a philosopher. You and I could have hung out together. Yeah, well, you are kind of. Do a little Seneca, Marcus Aurelius debate. Before it was cool. Yeah, exactly. No, I took a class called God, Self, and the Body or something like that in freshman year.

I just loved it. So I thought, but, you know, everybody said, like, what are you going to do with a philosophy major? So I thought I might go into politics, like helping in a governmental role. And I did a summer in DC as an intern and didn't love it. And so business became sort of the next thing. And I guess I have been sort of a philosopher in business. Certainly, that's part of the reason I like writing books about it.

But no, I had no idea I was going to get into commercial real estate. And then at 26, on my 26th birthday, I finished a business plan to create this boutique hotel company called Joie de Vivre, which is a really impractical name for a company, especially in the US, because it's hard to pronounce, hard to spell. Most people don't know what it means. It means joy of life. But very few companies in the world have a mission statement that's also the name of the company. And that's what really resonated with me. And yeah, bought a broken down motel, pay-by-the-air motel in the Tenderloin, called it the Phoenix, and it became a rock and

roll hotel and a big sensation. And that's how I got started. So if we back up a little bit and revisit Stanford Business School, in the course of preparing for this, read about brainstorming sessions that you did. I think they were a few hours in length. I hesitate to say four hours because, of course, I'm the four-hour guy. But I think that in the article, it was four hours. Yes. And there were some other characters involved. You've done your research. Whose names may be recognizable. I think Seth Godin was four hours. Yes. And there were some other characters involved. You've done your research.

Whose names may be recognizable. I think Seth Godin was also one. Seth and I wrote our first, we both wrote our first books together when we were in our second year of business school. Yeah, this group was five guys. We were the five youngest guys in the class. Two of us went straight into business school.

The other three had had one year off. And we were sort of not well-liked, generally, within the business school class because we were just the innocent, naive, you know, dumb shits. Fresh off the boat. Yeah, so we sort of created our own little club. And we were brainstorming business ideas. Was there

a format to it? Did you guys meet on a regular basis? We met on a regular basis, and it was really the best way to describe it. It was each one of us would bring an idea to the table and then we'd critique it. And Seth is a good critic. Yeah, he's a very good critic. And so that was partly how I got to know Seth. And ultimately, Seth and I didn't love business school. And so our second year of business school, we said, why don't we write a book, get credits for writing the book, use that experience to go out and interview a bunch of famous people who will talk to us because we're business school students.

But once we graduate, they won't talk to us because they'll think we're looking for a job. Use that Stanford while you can. And we did. And we created a book called Business Rules of Thumb. And it came out a long, long, long time ago. And yeah, Seth at that point had caught the bug. He knew he was going to write books. I hadn't caught the bug. It wasn't until about, gosh, 16, 18 years later that I wrote what I consider my first book. I don't actually count that book as one of my five books,

unfortunately. I don't think Seth counts it as well. If people are listening and they like the idea of forming a group like this, because I think that, at least in the piece that I'd taken a look at, the consensus of some of the people in the group was that you learned more through those sessions than you did through the coursework. So if people out there are listening and they think they want to create their own group whether they call it a mastermind or a brainstorming group or whatever it might be where they have the opportunity to put people

say in the hot seat and to have their ideas critiqued and to offer the same do you have any guidelines or recommendations on how to do that well or what the necessary ingredients are? Well I think the most important thing is to have clarity about what the purpose is like that's sort of true in life and true with any business, but it's actually true

with a group. And so the fact that we knew this was a brainstorm around business ideas, mostly entrepreneurial ideas, was absolutely clear. If you don't have that clear, then people are using it for different purposes. And it's fine to have different purposes as long as people know each other's agenda. So I think that's key. I think another thing that's key is while it can be intellectual jousting, and so it can be hardcore, there has to be at least an underlying respect. If the purpose of it is to just skewer each other, people start to shut down or stop showing up. And so that's critical. And at the end of the day, we also had a good time. I think that was a big piece of it as well.

How long did they last? They could, I mean, well, we did it for the two years that we were in business school. What was the purpose? The purpose really was, I think all five of us wanted to graduate and become entrepreneurs straight out of business school. I don't think any of the five of us did that. Some of us went to work for very entrepreneurial ventures. But I think what we really wanted to do was incubate some interesting ideas such that in that second year of business school, we might determine if we were going to actually create a business plan. I think probably

it did incubate an idea. I had an idea in one of those sessions where I talked about creating sort of an urban retreat resort where people would go and go to workshops and classes and, and it would be a place where you could sort of get away from the city, but in the city there's a place called the Esalen Institute in Big Sur. And I've been on the board for basically a decade and I've been teaching there for a long time. It was like,

the bookstore is dedicated to you. The bookstore is dedicated to me. Thank you. in Big Sur, and I've been on the board for basically a decade, and I've been teaching there for a long time. It was like, take that place. The bookstore is dedicated to you. The bookstore is dedicated to me. Thank you. It is, because I gave some money. It's the only reason, not because I'm a great author or anything like that. So the bottom line is, I said, why isn't there an Esalen in the city? And that was an idea that percolated. Ultimately, it led me to buying a motel in the Tenderloin of San Francisco,

which is not exactly that idea. But I think it was- What year was this, roughly? So, 84 was when we graduated. So, I think probably came up with that idea. And it was 86 that I came up with the idea of Joie de Vivre and buying this motel in the Tenderloin. So, sometimes you're planting a seed. I mean, what's great about life is your brain, your soul, your spirit, your ability to channel something deeper than you from far off in the cosmos. These are things that actually sometimes take time. And so planting seeds early is wise. This is part of the reason I wanted to ask you what you thought you might be or what

grabbed you as an undergrad. Because if I'm, maybe I'm forcing a narrative, but I don't think so. Because I've seen this before in that you have philosophy. It grabs you. It has great appeal, but you don't know what to do with it at the time. So you bookmark it. Don't expect to ever come back to it. And then you plan on X, but you can't do it right away.

And it seems to me me at least for myself I try to do this if something really excites me I assume that there's probably a place for it or a role for it it just might have to incubate for a while exactly the question is timing and what form it will take so I think for me

the thing that was really interesting is that writing that book with Seth, the second year, incubated 16 or 18 years later in my first official book, which was called The Rebel Rules, Daring to Be Yourself in Business. And Richard Branson wrote the foreword. clear to me was, and has been a practice my whole business career, is making a weekly inventory of what I learned that week has been essential. And I think that every Friday afternoon, I started doing it when I was in my mid-20s. And I would almost do a half hour to an hour, usually on Friday afternoon, sometimes over the weekend, and said, here are some of my key lessons of the week. And I created a wisdom book, and it was called The Wisdom Book. And that wisdom book was the collection of lessons that I was learning along the way. And it wasn't like I went to the

wisdom book all that often to look at it. I did do it. In dark times, I would go there. But generally, it was just the act of putting it down that was planting a seed in my consciousness to take notice. When did you stop doing that? Or did you stop doing that? I still do it. You still do it? I still do it. So, if I may. Yeah. And today's Saturday.

Today's Saturday. So, Friday on the flight to Austin, which I lost the flight, missed the flight. I had to fly to Houston and then take a lift from Houston here. I did my list. And this list was a really interesting list because this was a weird week. Now, obviously, this is going to be out in the public in a few weeks. But this week was the week that a New York Times article came out about our new Modern Elder Academy. And as people have said, people say, it's a great article, but it's not really very accurate. And to my mind, a great article is very accurate. So I don't love this article. And it's forced me to reacquaint myself with one of Victor Frankl's famous three-liner, three lines from Man's Search for Meaning. And so, that went into my lessons

this week, which was 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. And I had to really watch that. I would look at those three sentences over and over because I was just getting more and more indignant and almost feeling betrayed by the journalist because she didn't give a factual story. So long story short is this week my list of lessons were very much about emotional regulation, which is really something that we learn as we get older. There's a lot of things that as we get older. There's a lot of things that as we get older, we are very aware of the things that actually get worse with time, but we're actually not as aware of the things that get better with time.

How long is, say, the total set of bullets for this week? Is it a page? Is it two pages? It depends on the week. The bloodier the week, the more bullet points there are. The average week is about five. Five bullets. Five bullets of... Oh, look at that. On Fridays. Five bullet Fridays.

Oh, wow. That's interesting. But your bullets and my bullets are different. My bullets are really actually lessons. Yours are... You're not like, here's my favorite spatula I found this week and your lessons learned now? No, nothing like that, no. They're actually, yeah, they're deep and sometimes painful. This week, there were probably 12 bullets

and some of them were like tactical. Are you willing to share any of them? Yeah, like one of them was, I said to my PR person, I got this article on my own. You know, I know the journalist. I wouldn't say we're friends, but we know each other moderately well. And I think she'd probably prefer just the one-on-one.

And she did. But I didn't necessarily have someone there to sort of say, hey, yeah, Chip said these things. And why are those not in the article? And you put something else in there that he didn't say. And so I think part of it for me was, okay, yes, it's normal to have someone there as a PR specialist, especially for an article as important as, say, the New York Times would be. That's another example. I gave the Franklin example. Another one is when things are troubled, it's the most important time for the higher you are in an organization to be calm because our mirror neurons mean that our emotions are contagious. And everybody tends to look at the most senior person

to see how they're reacting to something. And so when something goes askew, people look to the leadership to see, are they sweating? And I'm not saying that we shouldn't be authentic and transparent, but you can be both vulnerable and a visionary at the same time you can also be very serious and calm at the same time yeah for sure if need be so i think that i've i've tried to to be that way and not you know get like so wrapped up in a reaction you know

frankl's quote is really about reaction yeah response versus react and the the longer we're on this earth, often the better we get at being responsive as opposed to reactive. What other practices or books or resources, anything at all, has helped you in developing your, what was the phrase you used? Not emotional resilience, regulation. Yeah. I think I've been lucky enough. I'm awful at yoga. People say, oh, you got the yoga body. You sort of seem like you're like a yoga guy. And I'm like, I'm really tight. I have a hard time with that. But I'm really good at meditation. And I took to it 35 years ago. And I've integrated it into my life ever since then. And I would say a morning practice of just

meditating as well as sometimes an afternoon practice or a practice when I'm most stirred up is to just close my eyes, give myself 10 minutes to just absolutely get into a mantra of just breathing. And that actually is a way of regulating myself. Clearly exercise and just getting it out of your system and getting out of your brain. I mean, so much of emotional regulation is learning to get out of your brain. And so I've done that too. But I will say back to the yoga for a second.

I think there's two ways that I look at life. And that's to be in an attainment mode, trying to attain something, and in an attunement mode. And what I've found is that my natural tendency is very attain-oriented. And when I'm in the attain mode, I often have to atone afterwards because I have sharp elbows and I'm just going for what I want. Attain and attune or atone. Well, it's attain, yeah, it leads to atonement. Attune leads to at one.

So for me, that's been something for about a year now. I've been able to sort of see myself. And so ask myself, am I stirred up because I'm in the attain mode? Attain is perfectly fine. Yet yoga is not an attain sport. Surfing, which at age 57, 56, 57, I'm 58 now, I started learning to surf. This is not an attained sport. The key is to attune yourself

to the wave. And so recognizing when you're supposed to be in the attained mode and when you're supposed to be in the attuned mode is something that i think i've learned over time and is your meditation practice mostly focusing on the breath and letting arise whatever arises without trying to modify it or what is your what is your internal practice like when you sit for those 10 minutes i have a lot you know so the 20 so i've done tm and that's a 20 minute practice and that's the that's sort of my core the mantra that that I do. Yeah, but mantra-based, try to do it morning and afternoon. At minimum, I do it the morning. I do a lot of other ones as well. There's a loving-kindness meditation

that I sometimes will do, which frankly, when I'm most stirred up about someone in particular, I can sort of go that direction. I love Vipassana, but that's more of an extended silent meditation practice. And like right now, two years ago, I was in Loretto Bay in Baja kayaking with a guy named Mark Coleman, who wrote a book called Awake in the Wild, beautiful book, kayaking with him and

12 of us from island to island amongst whales with a silent kayaking meditation retreat for a week. Didn't talk for a week. That was beautiful. So I think, but the simplest thing to do, I think of two things. It's just, it's breathing, learning how to breathe. The thing that I do that's the Chip Conley little trademark is I think of louvered windows in my forehead. Hold on a sec. What windows? Louvered, like, you know, like sort of glass louvered windows in my forehead. Hold on a sec. What windows? Louvered, like, you know, like sort of glass louvered windows. So you sort of open them

and they just sort of like, they turn. And so actually the reason I like them is we have them at the Phoenix Hotel. I was going to say, they're sort of like the, they make me think of really old Volkswagen camper buses that have that type of rotational window. Exactly.

So you have a rotational window. It's like the vents in an air conditioning duct in a car. Exactly. Imagine that on your forehead. Okay. And so what I do is I breathe through my forehead and then I breathe out my forehead. And this is how I turn down the heat on my brain.

I mean, truly, this is like my, the Chip Conley approach. Whatever works, works. Yeah. So that's, you know, but yes, the core thing I tend to do is the TM. The TM. And for people who are interested in the second you mentioned, which is loving kindness meditation, also known or called METTA, M-E-T-T-A, there are some fantastic guided meditations that

you can listen to out there. Like Jack Kornfield has some fantastic versions of that. There's also a really fascinating guy named Chade Meng Tan, who wrote a book called Joy on Demand that gets into this. And Search Inside Yourself, too. And Search Inside Yourself, which became the most popular employee class at Google at one point. And we're on a waiting list of like six to 12 months or something like that.

So let's go back to something you mentioned. Your first book, the first book you count, how old were you when you wrote that, roughly? I was 38 when I wrote it. And yeah, so I'd been running my company for a dozen years, Joie de Vivre. How did you get Richard Branson to write the foreword? Great question. You know, so Gavin Newsom, at that point he was the mayor of San Francisco

and he was my first mentee. I mentored him at Menteed. So we went together to see him and give a talk at the Virgin record store in San Francisco. I remember that. It used to exist. So it was actually around the launch of that record store. It's hard to imagine. Right on Market Street.

Yeah, I remember like a record store. Really? It wasn't that long ago though. So we went there and we were there with the head of protocol for the city. Actually, this was before Gavin was mayor. He was just on the board of supervisors in San Francisco. And we, I don't know, he just took a liking to both of us. And so he said, can we hang out?

How did you meet him in person? We were literally in line to actually have him sign our book. And it was me and Gavin. And so when we came up, he just ended up spending a bunch of time with us. And we waited a little bit later and he talked with us, just the two of us. And we went out and had a meal. I'm going to keep chipping away at this, no pun intended. So you walk up. You're good with words. Gavin's also good with words.

So you guys walk up. There's a long line of people. What do you say or ask that gets the attention of someone, or what is the presence that you put forth that gets the attention of someone like Richard Branson, who in that what is the presence that you put forth that gets the attention of someone like Richard Branson, who in that environment is, he's the king. I can't remember the names right now, but I learned his parents' names, his mother and his father. And so I went in the front line.

I knew there was something. I went in the front line and I said, so what influence did so-and-so and so-and-so have on who you are today? And he looked at me like, how do you know that? So that led to the conversation that led to a longer conversation. Amazing. Now, did you propose hanging out after the signing or did he? Well, it was the next day. And we just had lunch the next day. And the truth is that his company, it was just in the early stages, I think, of thinking about doing Virgin America, the airline. And I was at that point, the largest hotelier in

San Francisco in terms of the number of hotels we had. So there was some benefit to him as well. How did you make the jump from him being impressed that you knew his parents' names to meeting the next day? You know, actually, he had an assistant there. And his assistant actually did know me and knew Gavin. So she was wise enough to know. And she said,

can you go talk to April over there? And so we went over and talked to April. And April said, you know what? He's got some time to schedule tomorrow. Amazing. And then flash forward, and you have a forward from Richard Branson. So yeah, ultimately he said,

I'll write it, but you're going to write the first draft. And then he edited it, and it went in it. All right, so we're going to yet continue this forward and backwards chronology, if I can even call it such. Who's Brenda Lee?

And this may go somewhere, it may not go anywhere. Brenda Lee is this 4'10", although she's 5'6", with her beehive hairstyle, Nashville gal, famous country-western singer. And out of the blue, her bus, her pink bus was driving through the Tenderloin in San Francisco looking for a place to stay. And this was about a month after we opened my first hotel, the Phoenix. Paint a picture of the Tenderloin at this point. Well, it's the same as it is now. It hasn't changed that much. There's a lot of drugs on the street and it's a relatively

poor neighborhood, pretty desolate, but it's right in the middle of the city. And it's right near Union Square and the hotel district. So we were the gateway to the Tenderloin, but we were on the opposite side of the Tenderloin from where the nicer part of the Tenderloin and Union Square was. So she's driving through there and they're looking for a place to stay and she wanted a motel and we were a motel. She comes in, she had no idea that our aspiration was to be a rock and roll hotel and so she comes in and we had weirdly enough a guy named arlo guthrie staying at the hotel at the same time listened to arlo guthrie when i grew up so i know this land this is that amazing yeah so arlo guthrie's in the hotel because the Great American Music Hall is two blocks away.

Brenda Lee comes in with her bus and we have bus parking. So one of the beautiful things about the Phoenix is it had free bus parking, which a band's going to appreciate. And she checks in and all of a sudden

we'd become a rock and roll hotel. We had Arlo Guthrie and Brenda Lee and that led to Nirvana, Pearl Jam, David Bowie, Red Hot Chili Peppers, everybody you can imagine staying there over the years. The way you tell the story, it's like they show up and then all of a sudden we're a rock and roll hotel. I know there's more to the story. There's more to the story. No, no, no.

So how did... Okay, so you have manifested or chanced upon this luck of having these two guests at the same time. How does that then get converted into a reputation? Do they just recommend to other people? Do you seize upon that? Hey, can we take some photos? How does it happen? There was some logic.

So my business school brain was saying, OK, well, who's the person who books all of the hotel rooms for bands coming through town? And I'd gotten to know Bill Graham, who's a music impresario, a concert promoter. And he had said, well, it's usually the concert, whoever's booking the concert, they're doing it. So we tried to market to them. Then we tried to market to the venues,

like Slim's or the Great American Music Hall or the Fillmore. That made sense. And then we found out, oh, there's these travel agents who specialize in entertainment travel. So let's go to market to them. To be honest with you, none of those worked all that well. They worked okay.

The number one thing that worked, this is so funny, was the person who typically made the decision of where the band was going to stay was the tour manager. So the tour manager was usually a guy, almost always a guy, about three to five years older than the band. His job was to make sure there was no overdoses and no groupies. And because a groupie might mean the guy doesn't show up at the show. And of course, an overdose could do that as well. And by the time he got to San Francisco, he was so stressed out because usually the tour started on the East Coast. And by the time he got to San Francisco, so here's what we did. We had one room of our 44 rooms

that was a massage treatment room. Now, back in the old days when it was a pay-by-the-hour place, you can imagine what happened in there. But we cleaned it up, and we made it into a legitimate massage studio. And so we offered to tour managers, when you bring your band here, if you give us 10 room nights, five rooms times two nights, you get a free massage for yourself. And so back in

the day when we started doing that, now remember, this is pre-cell phones, pre-internet, pre-frankly laptop computers. People had satellite phones, but mainly what they were doing was going on the house phone and the tour manager's calling his friends and then sometimes writing a letter and sending it out to them in old school US mail and saying, there's this place in San Francisco that actually gives you a free massage. And that's when I realized that really great entrepreneurs don't deliver on your expectations. Well, they hopefully do. They deliver on your expectations. They deliver on your desires. But the thing they get right is this thing at the peak of the pyramid. I wrote a book called Peak, How Great Companies Get Their Mojo from Maslow.

It's meeting the unrecognized needs of whomever your customer is. And in my case, figuring out that the customer was not all those other people. It's actually the tour manager. And what's his unrecognized need? It's basically to chill and to relax and then get a free massage. That's incredible. And because it also acts as a contrast in my mind to a maxim that is often used, but I think often inaccurate, which is you, granted you had this motel slash hotel, but you need money to make money.

But if you look at what you did in that particular case, I mean, you identified who your actual customer was. It was like the unspoken customer. No one told me. No one ever said that was the term. Yeah. And then the unspoken need and the cost to offer that service is just a rounding error. I love, you know, it's a great entrepreneurial story

to sort of suggest that sometimes it's not the thing that's most obvious and it's not the thing that's the most expensive. But this idea of the unrecognized need, how do you mind read your customer well enough to know what it is that they would love? We have a hotel later that we created, which you and I've been to, the Hotel Vitale, which is on the waterfront in San Francisco.

I wrote a bunch of two of my books there. Oh, thank you. Well, so long story short, the Hotel Vitale, like the Phoenix is in the worst neighborhood in San Francisco. And the Vitale is sort of like the best neighborhood. It's right on the bay, on the Embarcadero, right across from the ferry building and the farmer's market. So the unrecognized need for the customer we wanted there. So the Vitali means vitality in Latin or in Italian. And we wanted to create a hotel that was sort of what we called for the person who was post W and pre Four Seasons. David Brooks would call him the bourgeois bohemian, so the bobo. The hospitality tweeners. Yes, the hospitality tweener who sort of was looking for that. And so our point of view was,

we said this is a person who reads real simple and dwell. So it's actually probably more female oriented, and it's a female business traveler. And if there are five adjectives to define those two magazines, modern, urbane, fresh, natural, and nurturing, that describes this person. And so we ended up creating on the top floor of the Hotel Vitali when we launched 15 years ago, a yoga studio on the penthouse level that had free yoga classes every morning. Now, my investors looked at me like, and they're all guys, looked at me like, what are you doing? Now, today, this might make sense. 20 years ago, when we were concepting this, they're saying like, there is no financial district hotel in the world that has a yoga studio on the penthouse level.

Like, why would we ever do that? And I said, well, because we're going to be the first ones doing it. And so then they said, well, look at all of the customer satisfaction forms you've gotten from people in financial district hotels. And they asked for a yoga studio? And the answer was no, 10,000 of them. We looked through 10,000. Not one person ever said, why don't you have a yoga studio in your hotel? But if you're good, and if you really understand your customer, it goes beyond the expectations, beyond the desires, beyond focus groups. It's the thing you know that they want next that they don't even know they don't want. They don't even know they want.

So long story short is the yoga studio had to line out the door. And within a month, we were in New York Times, LA Times, Wall Street Journal had stories about this new sort of hotel that's oriented toward business travelers who want to stay healthy. And the Hotel Vitale ended up becoming

the most successful upscale hotel in San Francisco. It's reminiscent to me of, and this could be apocryphal, I don't know if this is a real anecdote. It's kind of like every quote is attributed to Abraham Lincoln or Oscar Wilde on the internet. Did you know they had a thing, the two of them?

I'm kidding. A quote off. Henry Ford Ford I think If I had asked people what they wanted They would have said a faster horse That's Henry Ford I at least attribute it to We can't ask him

And to look under the hood On that decision a little bit So the first is And this is something that I'm Constantly Maybe constantly is too strong a word, but I always consider when I'm looking at launches or books or television shows or documentaries, whatever it is, is being first. I think the doing something the first time can be really

undervalued. Being second, different story, right? Being first can be very, very newsworthy in and of itself. Also, what would you have done if it hadn't worked? We would have turned it into a suite, right? So the key there, and you just said it exactly right, which is my point to my investors was, give me six months. me try this we can ratchet and make it into a suite and that in fact after we sold the hotel a bunch of years later that's what they did um but i said give me that time because this was not going to be insurmountable if it didn't work out but it turned out to be it

turned to package and position the brand of the hotel really well and be something that people valued. But I think the point on that is to sort of say, okay, so how do you try things and do something small enough, but that could have a big impact that is easily solvable if it doesn't work. Right. Which is also something that can be tied into Richard Branson, right? Because people think of Richard Branson as this throw caution to the wind maverick who risks it all despite the odds. And he's been on the podcast, but you've spent time with him. And if you look at, I believe it was Virgin Atlantic, where he took so many in-between steps to cap the downside on something that could be unmitigated,

a complete disaster, right? Airlines. It's like magazines, restaurants. You can really lose your shirt. And among other things you know tested with i want to say like a poster board in an airport when a flight was canceled something like virgin airlines and it was a chartered flight that he was going to book if he got enough people to sign up for you know the eight or ten seats that it would take did that

successfully and then negotiated with i want to to say it was Boeing at the time, in order to be able to give them back the plane if it didn't work. So behind the scenes, he's actually making very, very calculated bets. He's a shrewd guy. Super shrewd. Yeah, and I think one of the things I learned from my dad a long time ago is build the business plan as if it's not going to succeed. I mean, imagine it succeeding and you're going to attract people

for that, investors, employees, but what's plan B, you know, and how do you have a solution for plan B? And so that's why I don't build bowling alleys. You know, bowling alleys sort of like, in terms of the shape of them, you can set in the past churches, but churches have become sort of popular for all kinds of uses post-church era. But yeah, I think it's really critical to sort of understand what is plan B, C, and D. So let's talk about another chapter shift. And I'm going to take this opportunity to pull up a screenshot of a text exchange that I had with an unusual friend of ours with Liz. So could you explain for people who don't know who Liz is just for a second?

So Liz Lambert hates me. She even said on your podcast, she hates me because I did for her what now I hope and expect she does for other people, which is she reached out to me almost 20 years ago. I had become a successful entrepreneur hotelier, boutique hotelier, and she was creating this funky little motel here in Austin called the Hotel San Jose, and similar to my Phoenix. And she liked what we did with the Phoenix, although she was going to do something that was a little more upscale. And she wanted my help. And so I came here and gave her some suggestions. And then I actually sent my general manager from the Phoenix, Monica Bernstein, down here to Austin basically to help her get launched.

Why did you do that? She wasn't here for that long, but she was here for, I don't, you know, I can't remember, but like weeks at a time. I did it partly because I loved Liz. You know, I love, you know, she's an attorney who should never have been an attorney who's completely amazing as a designer. So she's one of those hoteliers who designs her own hotels, which I love. That's sort of like, you know, like a restaurant tour where the chef is the restaurateur.

So I think that's really beautiful. And so I just loved her passion and her sense of the, you know, her joie de vivre, frankly, the, she had, took it such a joy in what she was doing and I wanted her to succeed. And so, you know, I am a big believer in karmic capitalism, which means sort of what goes around comes around. And so me giving to Liz was going to pay back to me in some way over time. And frankly, it's been me doing that with a lot of different people and then having it come back reputationally. Your reputation is one of the few things in your life that's portable. And frankly, it arrives FedEx before you arrive somewhere because that's what happens with

the reputation. People know you before you arrive. And I think that whether it's Liz or a variety of other people who I have tried to help in business, it's just helped my reputation in terms of how people see me. And instead of people standing on the sidelines, sort of like jeering, they're cheering. They want, you know, when the New York Times article came out this weekend, I didn't love it. I had such a support network of people who just said, you know what, we're going to write letters to the editor because it's not a bad article, Chip, but you know what,

it's not accurate. And they wanted to help. And I think, you know, I once had a restaurateur, co-founded a restaurant with someone and no one really liked her. She was actually very shrewd, really tough negotiator. But when she launched a restaurant, if she got a bad review, people were sort of silently happy. And I'm not that way. And I'm not saying that to say I'm the most likable person in the world, but I will absolutely say that I do a lot of things to make that karmic capitalism work for me in the world. And as such, Liz was just an example of that. And the reason she hates me is because now she feels the obligation to pass it on, pay it forward to someone else because she gets hit up all the time because she's just an amazing hotelier.

She's really incredible. The company's called Bunkhouse. Bunkhouse. And she has a number of just incredible, not just incredible properties, but incredibly different properties. They're soulful. You know, at the end of one of her pools, you know, the St. Cecilia pool here in Austin, it just has, you know, neon soul. And there's something soulful to her places.

And so I want to bet on people like that. Yeah, there are a lot of parallels that I can see looking at the two of you, side by side in some ways. And it just struck me that I did a number of staycations at Hotel Vitale to work on books.

Because I think I had read that Maya Angelou had done that. And I thought, that's a great idea. Because at home, I have all the usual distractions and ways to procrastinate. Let me treat this. Moby would do that when he's... Moby. Moby would do that.

He'd go to a hotel room and just shut himself off for a week to actually figure out music. No kidding. So I have friends here. I won't mention their names, but they're well-known filmmakers because they told me this just in a private conversation

who use Hotel St. Cecilia for their sort of staycation creative work as well. So I'm going to jump to this text from Liz she had a number of questions i asked her are there any particular questions or topics that you think could be interesting or fun to explore so one of them she she gave me quite a few but one of them was he meaning you began building joie de vivre as a young man it was the work of the first half of his life a a big sprawling family. What made him decide to sell it when he did? So great question. You know, one thing, you know, to you aspiring entrepreneurs and people who are younger than

me, just know that when you, one of the natural tendencies is we hook our sense of self-esteem and self-worth to our businesses. I remember in the early days of the Phoenix, I had one hotel before I had 52. And that one hotel, when people come up to me and say, how are you doing, Chip? I said, well, the Phoenix is doing fine. And finally, somebody called me on it. It's like, I didn't say how I'm doing. So my sense of worth and esteem had a lot to do with basically the roller coaster of my business. Well, fortunately over time, I realized that didn't have to be the case.

And it was that flatline experience I had 22 years into running my company that helped me to see that, is this what I want to do the rest of my life? Actually, it's not. And I thought it was going to be, but it wasn't. And more than anything, I just realized that I started the company for creativity and freedom.

Those are the things I said to myself on one Friday afternoon when I said, what did I learn this week about why I'm starting this business? And 22 years later, I said, do I have any creativity and freedom in this business anymore? No, I'm running a company with 3,500 people. So that's what led me. It was hard, though. It was very hard to sell a business that for, ultimately, when I sold it, it was 24 years, that has been your identity for most of your adult life. But it was actually harder for other people than for me.

And that's the fascinating piece of it is I realized my identity had moved on. I was ready for what's next, which was to become the world's leading expert on festivals. And I didn't really want to be doing it anymore. But I had to deal with other people's challenge in me changing my identity. And there's lots of ways people change their identity. You can get divorced. You can change your career completely. You can literally change your gender. But in my case, it was just changing the actual fact that I was the founder and CEO of what was the largest boutique hotel company, second largest in the US, but the largest hotel company, frankly, in the San Francisco Bay Area. And for some people who liked having their friend have that role and got a lot of free hotel rooms out of it from me or restaurant reservations or massages in my spas, they didn't like it.

But at the end of the day, it was the right decision. So that, as you just said, sounds like a difficult decision or a maybe emotionally intense decision to work through. And I mean, I remember when this was kind of happening. And you mentioned just in passing here, I decided what I wanted to do next, which is become the worldwide expert on festivals. Did you need to find that before you were comfortable on some level with making the decision to move on? Or did you make the decision to move on,

pull the trigger and then find that next thing? Yeah, no, that's a great question. I made the decision this was going to kill me if I kept doing it. And so I knew I needed to move on. I didn't know. And frankly, then you get into the freaky. It was in the Great Recession, the freaky thought of like, how am I going to sell this company in the bottom of the recession?

So I hadn't yet found the new thing I was moving toward. I knew what I was moving away from. But moving toward something is really important because otherwise, when you do leave it, you actually, it's like when people retire and they end up on a golf course depressed because they actually didn't move toward something. They just moved away from something

and they just are sort of like almost, you know, just wasting their time. Yeah, they're just in a void. They stepped into a void. They stepped into a void. And so the fact that I got to a place where ultimately I said, you know what, I'm fascinated with festivals. I'm on the board of Burning Man.

And there's no great website for all the world's best festivals. Maybe I'll just go around and become the world's most interesting person and go around to festivals all over the world. And I did that, 36 festivals in 20 countries in one year. And that helped me. You have a great blog post on Tim Dodd blog about some of your experiences at these festivals. I do.

That's right. Yeah, so I loved, loved that process. And it did help me move to what's next. Plus, I wrote another book. I wrote a book called Emotional Equations that did well. It became a New York Times bestseller. And it was another thing that just said, listen, this is my new identity. At that point, that was my fourth book.

And I was like, okay, yeah, I write, I speak, I go to festivals, I live a good life. You know, stop, you know, giving me shit for the fact that I'm no longer a boutique hotelier. So you mentioned the emotional equation. So I remember this. And could you explain despair equals suffering minus meaning? Yeah. When I had that flatline experience, I was in St. Louis giving a talk. I basically probably had an allergic reaction to an antibiotic for my septic leg and my broken ankle. And I went to the other side nine times over the course of 90 minutes. Where were you when this happened? Did you make it to the hospital before you flatlined? No, so I was giving a speech on crutches,

which is the first sign that Chip should have been staying in bed and not on this book tour trip. I was like, yeah, why was I on crutches on stage giving a speech? Fortunately, I did not fall over at the speaker as I was standing up at the mic, but I sat down signing books, and that's when I slumped in my chair.

I probably didn't have a flatline experience there. I just went unconscious for three minutes. Fortunately, the paramedic showed up a couple minutes later really quickly, and they put me on a gurney, and they put heart monitors on me, and that's the first time of nine times that I went flatline and they had to get the paddles out the first time. Uh, I didn't have to use them. Uh, about five seconds later,

my, my heart came again, but over the course of the next 90 minutes, uh, in the ambulance, in the ER, et cetera. And I kept saying,

okay, this is what I saw on the other side. And they, whoever was there would take a note of it. And it turns out it was the same thing over and over again. But long story short was... Well, hold on. Let's not do long story short.

You can't do long story short on near-death experiences. What did you see on the other side? There is, by the way, a festival of the near... a pilgrimage of the near-death experience

in Spain. Spain has the weirdest festivals in the world. What I saw was this and the fact that it happened over and over again means it's pretty remarkable and worthy to just talk about it. So I don't love the mountains. I love the

beach. Mountains are okay. I do like it. I love being in nature. So it's interesting, this is a mountain setting. So it's a mountain setting, a chalet with a huge sunroof for skylight and light is pouring in the skylight, beautiful light. And it's pouring in in such a way that there's actually this viscous oil, very heavy oil on the ground on the most beautiful wood-grained floor you've ever seen. And it's because of the way the light's coming in and it's hitting the floor, this oil that's sort of slightly moving, or it's like going down these stairs, these beautiful wood stairs, it's casting this beautiful kaleidoscope of colors on the wall. And so what I see is light, I see colors, and I see this weird, this frangipani-scented oil going down these stairs. And that's what I kept seeing. And I never saw anybody else. I didn't see anybody on the other

side. What I saw myself is observing almost floating above this. I felt incredibly peaceful, and everything was moving very, very, very slow motion. So, and I kept coming back to that. And I don't really, I've never actually sat down with like a dream analysis or anyone to sort of say, what does it mean? The fact that it's stairs going downstairs means I may be going to hell. But actually it was up at a mountain chalet

way up toward heaven. I don't know. All I know is, forget about heaven and hell. What I know is in that moment, I felt beauty and calmness like I'd never felt before. So, yeah. That, so the, I was in the- What did you make of that? Like, I mean, and I'm not saying it, there is no, whether, if you had a Freudian dream analyst here and they said, you know what that means? Let me tell you. I'd be like, bullshit. Come on. You can give us your opinion.

Yeah, exactly. It's common. What did you... What do I take from it? Yeah. What do I take from it? Subjectively, yeah. First of all,

I take from it that I... How I want to honor and experience beauty in my whole life. You know, the gods of efficiency, which tends to be my religion, these gods of efficiency have a tendency to force me or have its way with me in terms of just getting

very clipped in how I do things because I have to get all these things done. And being clipped and doing things doesn't allow for the time to have the immediacy of seeing in that moment that beautiful thing. So I think what it's helped me to see is like, how do I create beautiful moments in my life? And how do I take time to do fasting day, three or four days fasting in a row and things like that, that allow me to just be in the moment. That's one thing. Number two is the calmness I felt. So no fear of like, okay, you know, I'm dying and it's just going to be terrible. There was that. But I think the thing

that was most interesting was just the fact that the oil was moving so slowly. It's like, there's a ketchup commercial anticipation a long time ago, maybe Heinz 57 ketchup. It was like, it took so much work to get that damn ketchup out of the bottle. That's how it felt. And so what it felt for me was like, I'm slowly moving to my death, but it's a long time from now. And so that's what I take from it, which is a positive, you know, overall perspective. That night, after having all those experiences, I'm by myself in a room at the hospital in St. Louis. And weirdly enough, in my backpack that I'd brought with me on this trip was Man's Search for Meaning, Viktor Frankl's book. And the reason it was there is because I'd gone through a few really rough months. And one of my closest friends, who was

my insurance agent, whose name is Chip, had committed suicide four months earlier. And so I was trying to make sense of my life. And so here I had this book. And as I'm reading this book, I had a hard time sleeping that night. I'm reading this book and I was just distilling if I were to take the meaning of that book, Man's Search for Meaning, and turn it into an equation, it would be despair equals suffering minus meaning. And the way I thought of it is suffering is sort of a constant if you're a Buddhist and I slightly am if you believe that suffering is always ever present

it's the first noble truth of Buddhism and yet meaning or suffering and meaning are actually they're sort of inversely proportional to each other so if you do the math of like okay suffering

despair equals suffering minus meaning, eight equals 10 minus two. If you take two and turn it to four, then eight becomes six. And so despair goes down when meaning goes up. And this is when I realized that that practice I've had since being a 23-year-old of writing what my lessons were for the week was a practice that actually

was giving me meaning. And that equation, which I came up with that night, I ended up teaching it to all of our leaders in the company as we went into the Great Recession. And ultimately, I said, darn, I went to Bhutan to study the Gross National Happiness Index because I wanted to see what's the happiness equation in life. And I ended up giving a Ted talk about that. And then I ended up deciding to write this book, which was a series of 18 equations that sort of help you make sense of your emotions, whether it's happiness or disappointment or wisdom. Are there any other equations that you find yourself referring to or thinking of more often? Yeah, I'd say a couple. The anxiety one's

very relevant in the business world, and that's anxiety equals uncertainty times powerlessness. So it's not a plus, it's a times. So the uncertainty and the powerlessness together are combustible. So what I help people to see if they're in that space is what is it that you can try to find some certainty about? And what ways can you actually create some influence and some sense of power? And by doing that, you actually help people get to a place where they have a little bit less anxiety. Makes it very tangible, right? It makes it tangible.

Or disappointment equals expectations minus reality. That's a classic one for any business. Like, okay, what's your customer expectation? And then what is it that you're giving as reality? And if the disappointment is more predominant than the reality, then there's going to be, I'm sorry, if the expectations are high and reality is low, disappointment is what will come from that. So, and the expectations are high and reality is low, disappointment will come from that.

So both are negative. The happiness one that I learned in Bhutan was happiness equals wanting what you have divided by having what you want. Wanting what you have speaks to gratitude. Having what you want is the process of gratification. So it's not to say, this is not the, so it says gratitude is better than gratification. Well, that's fine if you're a Buddhist. That's fine if you don't want to go out and attain, attain, attain. I want to go attain, and I want to go gratify. But gratification doesn't necessarily bring happiness. It may bring success. And for a lot of people who think that success will bring happiness, you know, they go on the hedonic treadmill and end up realizing just when they get the thing

that they thought they wanted, there's some new shiny object that becomes the new thing. The rabbit leading the greyhound around the track just sped up a little bit. We know that one. Tim, okay. Occasionally we go there. Well, you know, it's you, me, Liz, and a few million people who might be listening to this. And speaking of Liz, so this ties in very, very nicely.

Yeah. So both you and Liz are very thoughtful and make a point of trying to be aware of your own thought processes, reasons for doing things, the drivers sort of behind the superficial answers that we're all inclined to give, that are fast and easy and expedient.

So one of her questions was, I noticed the chip has made a few life changes, selling Joie de Vivre, Airbnb, now doing what you're doing. For what looks from the outside like a conscious choice to simplify his life, slow down a bit, but does he always jump into something else big and sprawling? I know a lot of people, in parentheses, like me, I suspect, just can't help themselves. How do we learn to just be still? Should we? Is that the goal? Wow. How do you begin to think about that? I want to wring her fucking neck.

No, I'm kidding. But this is, I think, something that a lot of people who have become good at achieving struggle with. Oh, totally. You know, Peter Guber, I got to interview him on stage. He's one of the... Actually, you know Peter Guber.

We actually have both been in his box at the Warriors games. I interviewed him on stage, and this guy's 20 years older than me, and he's been successful in so many different ways. And I was interviewing him on stage at the Airbnb Open, which is our big host open that I was in charge of. We had 20,000 people in LA at this one. And so was interviewing him on stage at the Airbnb Open, which is our big host open that I was in charge of.

We had 20,000 people in LA at this one. And so I'm on stage with this guy and listening to him and thinking, oh my God, that could be me someday. And he's an amazing guy, but he's constantly so driven to succeed at the next thing. And so what I took from that and what I take from Liz's question is, I think the real question here is not whether you're going to just be still. I love being still. of Cabo San Lucas on the beach, learning how to surf and having a very simple life there,

it means there's been a lot of conscious choice of how I'm curating my life, not living in San Francisco anymore. And yeah, I have these ideas that I feel like I want to go out and try in the world. But the question is, how am I executing on them? And what is my intent? Or what's the sort of the silent intent for why I'm doing it? And I think for so many of the things I've done in the past, certainly Joie de Vivre was at times an exercise in seeing how big Chip's ego could get. Now, I say that not to beat myself up, but I do say that from the perspective of,

I was this guy who was getting a lot of my sense of self-worth from the fact that this hotel company was successful. And so my ego was on display. And then I joined Airbnb because the founders asked me to. And all of a sudden, I'm not, you know, I was the tiny version of Richard Branson in my company. But now I'm like, instead of being the sage on the stage, I'm the guide on the side. And I'm helping these three co-founders take their little tech company and turn it into a global hospitality brand. And I realized in that process that I'm still driven. I'm still totally in it, although I actually was learning how to not do the 70-hour-a-week kind of thing, not four hours a week or whatever. You've been able to perfect.

Whatever that book was. Yeah. So, what I was realizing is that actually I'm not doing this for ego purposes. I actually feel like I'm doing this more for legacy purposes. I'm doing this to actually help them, and I believe in their mission, the Airbnb mission to belong anywhere, help people belong anywhere and turn strangers into friends. All of that was good. And now this Modern Elder Academy that I'm doing in Baja that she's reciting there, you know, the reality is, yeah, it is me being driven again, but I've put guard posts on it. I'm doing it in Baja. I'm doing one location. I'm not doing multiple locations. And-

You feel comfortable with that commitment? I feel comfortable. Yeah, no, I am. Actually, and frankly, the cancer, you know, for those who didn't hear earlier on the thing, I've got cancer. The cancer sort of was another educator of saying, yeah, I think midlife wisdom schools are a thing for the future in a huge way. I think the idea of lifelong learning and how do we go to a retreat

that helps us to repurpose ourselves, reframe our mindset, to have a growth mindset about our aspirational aging ahead of us. I think all that's important. No one's done that yet. There's been all kinds of retreat centers, but not a place that has a curriculum for people in midlife. When you say midlife, let's put an age range on that. Or it doesn't have to be age, but how would you, how does someone know if they're in midlife as- They're in crisis. Is it a plot?

No. No, you know, midlife has historically been defined as either 40 to 60 or 45 to 65. The truth is the phrase midlife crisis was coined in 1965. And the reason it didn't exist before then was because longevity in the US was 47 years old in the year 1900, and it became 77 by the year 2000. We added 30 years of longevity in one century. So what happened is this new era of life

sort of got emerged. Right, it's not yet fade to black. It's like, no, you have another half the movie to go. Well, you do, and the thing that happens in midlife, and how you know you're in midlife, whatever the age is, is you feel the weight of the accumulation of what you have acquired in your life. And I don't mean just the physical things.

I mean the friends, the responsibilities, the identities, like the sort of invisible name tags that define who you are in the world. And you actually, frankly, are sort of feeling overwhelmed by all of that accumulation. There's this reset that happens in midlife. And you could say, frankly, with the millennial generation, it might happen actually earlier in life. It might happen at 35. Frankly, in Silicon Valley, it absolutely happens in the mid-30s, especially if you're an engineer, where you feel like, wow, I am no longer perceived as an up-and-comer. And in an industry that is like the entertainment industry or fashion. Yeah, or professional sports.

Yeah, exactly. So I think, personally, mid midlife is from 35 to 75. And part of the reason I think, and I think it used to be just 45 to 65, it's happening younger because of the fact that people feel irrelevant earlier. And the digital intelligence that we desire in companies mean that there's a greater and greater desire to hire the new digital natives. And I think it's going to last longer, midlifelife because if we're going to live to 100, which is sort of the future as a longevity, we're right around 80 right now.

But by the time we get to the end of the century, I think we'll be about at 100 for longevity in the US. That means at age 75, you're probably still working. Yeah. And at least by choice or by necessity. You're creating. I mean, doing something. So I think that that period of time.

So midlife used to be a crisis. Now it's a marathon. And that's ultimately what led me to saying, you know what? We need to figure out this wisdom school. How do people go into midlife and not think of life as being just a one tank journey. Like you fuel up with all of your education and support up to age 20 or 25, and then you drive this vehicle that we call our bodies for the rest of our life. And at midlife, you're starting to run on fumes and you need a pit stop. And so the Modern Elder Academy is the idea of that pit stop. And I think it's going to

help to create a new category of academia or even hospitality real estate, which is the Midlife Wisdom School. Just like Canyon Ranch 40 years ago, Mel Zuckerman, overweight accountant from LA, wanted to go to a place to get healthy. And all the places that he saw 40 years ago were mostly like fat farms and mostly for women. And he ended up creating Canyon Ranch in Tucson. And it really sort of, it basically created a new hospitality real estate category called the Destination Spa Resort. Spas had existed for thousands of years, but not a category of real estate called Destination Spa Resort. So I think that's what I'm trying to do. So to answer in the long-winded way Liz's question, when I see something like that and I can see that I can be a social entrepreneur that's actually trying to fix a societal ill, which is

ageism and people getting stuck in midlife, I'm going to do that. And in this case, I'm doing it as a social entrepreneur with a social enterprise where 60% of the people are on scholarship. So I'm funding a million dollars a year in scholarships. That is something I want to bet on, but I want to bet on it as a catalyst for others to do their thing. That's what I was going to ask. Yeah. So Burning Man created a great idea. And so there's a bunch of 10 principles festivals around the world. Esalen, great idea in 1962,

led to 100 personal growth retreat centers. Got it. So the Academy is a proof of concept. It's proof of concept and a catalyst for other social entrepreneurs around the world to say, let's create one in the Sacred Valley of Peru or in Kyoto, Japan, or in the Catskills of New York. Do you think when you say, because I can see a

bunch of workarounds, to the one location limitation. So when you say one location, does that mean that you will be only hands-on in one location? Or do you envision some type of, for lack of a better descriptor, like a franchise model, or an association association or a loosely organized affiliate collection of dozens or hundreds of properties that Chip is somehow involved with. I love your enterprising mind and I have thought of all of those. Well, I just want to know when you say, I'm limiting it to one location, is there a footnote to that? Thank God for cancer. Honestly, the path that you're talking about, I was in contract negotiations on a second location and in discussions on a third location when I found out about my cancer on the second day of the book tour, right before the TED

Talk and six weeks before the Modern Elder Academy was opening to the public after a six-month beta period. So at that moment, I said no. And I keep saying no. The thing I will do is create sort of like the startup kit. Here's how you can create one. Not a Modern Elder Academy. We may only have one location in the world, but a midlife wisdom school. You call it what you want it to be. Here's how we can do it. I don't want to make, it could be a consulting opportunity, but I don't really care about the money on it. I'm lucky enough. Thank God for the Airbnb last six years of being there because I don't have to worry about money. That's for sure. I just like the idea that a legacy I can look to in my life is to create

a way for people to aspire to aging. Aging is not something that we aspire to. And yet, there are a lot of real unexpected pleasures of aging. The U-curve of happiness is... Do you know that? Do you know it? No. Oh, God, let's talk about this. So, the U-curve of happiness is, do you know that? Oh, God, let's talk about this. So the U-curve of happiness is so fascinating. It's so at odds with the societal narrative. I think I can see where this is going. So the U-curve of happiness has been proven in every country but Russia.

Russia, people get happiest after they die. It's a statistical error, clearly, but there's something to that. Every other country in the world that has been studied, what they show is the following. From about age 25 to about age 45, between 45 and 50, depending on the country, is a slow decline in happiness because of that accumulation. Because of that collection of things that we start to do that prepare us for midlife.

And then between 45 and 50, there's this, what Brene Brown would call the unraveling, another Texan. She's in Houston. Oh yeah. She might even be here in Austin now because her daughter's here. Yeah, exactly. So the great unraveling that happens in midlife where people actually start to discard things and they move from the accumulating mode to the editing mode. So that editing mode, the idea that people are moving into that mode leads people to get to a place where they get happier with each successive decade. So people are happier in their 50s than their 40s. They're actually happier in their 60s than their 50s. And they're happier in their 70s than their 60s.

Men start to flatten out in their happiness in the second half of their 70s. Women, it starts happening in their early 80s. So in essence, what it's saying, because women live longer than men, is there's a point at which five to 10 years before you die, you actually start to maybe get a little bit less happy. Because there can be acute health issues going on. But that's fascinating. The fact that we actually get happier as we get older, that is not what you see on the TV. Yeah, no.

And so I think the idea that, or the aging brain, we know the aging brain, we have less recall. What's your name again? Oh, that's right, we know the aging brain, we have less recall. What's your name again? Oh, that's right, Tim. The aging brain doesn't have recall or is not as quick as it used to be. But what a lot of people don't know about the aging brain is it gets more adept at doing left brain, right brain tango, which means basically the brain shrinks a little bit as it ages. It actually gets, it's able to, you're able to, as you get older, move from the linear left brain to the creative right brain much more easily, more adeptly. And what does that lead to in terms of a positive? It leads to being able to think more synthetically,

holistically, get the gist of something. So if you want somebody on your team to actually sort of like hear it all and then distill it down to the wisdom of like what they just heard, an older person can do that better than a younger person. Younger person is much better at doing focused. So why is that relevant? Well, you know, let's talk about Airbnb for a moment. At Airbnb, when I joined six years ago, we had, I love the founders and they were doing an amazing job and the company would have been successful without me. But when I joined six years ago, I loved the founders and they were doing an amazing job and the company would have been successful without me. But when I joined six years ago, and it was maybe 120th of the company besides today, we had 30 strategic initiatives in the year 2013 when I started. And nobody in the company, including the founders, could actually

recite all of them. So later that year, we did an offsite retreat in New York. And I said to the leadership team, of which I was now a part, I was Brian's mentor, but I was also reporting to him as the head of global hospitality and strategy. I said, we've got to get down to four. So for 2014, we're only going to have four strategic initiatives. And so we spent three days armwrestling over that one, 23 different potential initiatives that we were going to do. And it was that kind of distilling down. I think that. How did you do that?

Because I think a lot of people listening, maybe even one person sitting here talking, I myself struggle with long lists of perspective or current projects. Yeah, for sure. Right. So here you have a fast growing, very, very fast. I mean, understatement. So here you have a fast-growing, very, very fast,

I mean, understatement, growing startup. And they have a list of how many? 20-something? Who knows? Yeah, 23 initiatives that the 12 members of the leadership team thought should be our potential four for next year. So how do you facilitate a process

by which you get that down to four? Well, it's the intellectual joust. Because you're also kind of the new guy on the job, right? I was the new guy on the job and I was the old guy on the job. I was twice the age of the average person in the company. You know, 20 years older than, I was 21 to 23 years older than all three founders. But I think what they appreciated was there was an element of I think a modern elder versus a traditional elder the difference is

the modern elder is as curious as they are wise and it's that curiosity that opens up possibility and the wisdom is what distills down the essence of what's important and it's that essence of what's important that I think we got to in those three days in New York where we sort of said okay, so what is it we want to be when we

grow up? We want to be a place where people can belong anywhere. We had not said that out to the public yet, but that was the direction we were going in terms of our internal mantra of the two words that defined us. We also looked at, could we take the idea of the Airbnb sharing economy to office space or conference facilities or anything that had excess supply. There are a lot of natural sharing economy businesses that could be created. But we also had to ask ourselves, what's the dream of what we want this to look like five years from now, or maybe even 10 years from now, because Brian really wanted us to look very far into the future.

And maybe that dream could help become an editing function. So for me, that reminded me of something I did back in the Joie de Vivre era when I was running my boutique hotel company. When we were trying to figure out what's our differentiator versus Marriott or even Kempton, another boutique hotel company, we actually imagined the idea that we could ask the question, what business are we in? Because the number one Harvard Business Review reprint of all time came from an article from 1960 called Marketing Myopia by Theodore Levitt. And then management theorist and author Peter Drucker took that idea one step further. He said the most important question any business leader could ever ask themselves is what business are we in? Well, back in the Mejwana Viva era, we took that idea of what business are we in and we turned it into a little bit of a game. The idea was we would be asking executives or senior leaders to ask themselves that question

in the following manner. So one person would sit facing the other. The person asking the question would say, what business are we in? And the second person, the person answering would say, okay, we're in the boutique hotel business. The first person would say, thank you. What business are we in? And this time, the second person, the person answering could not answer the same way twice. And if you do that five times, it really almost is like an archeological dig to figure out the essence of your company. What's your soulful differentiator as an organization? This is how we found out that we were in the identity refreshment business at Joie de Vivre. And it was this same idea that we applied to Airbnb when it came to an offsite retreat we did relatively soon after I joined the company.

We sat our executives in pods of two so they couldn't hear each other. Any company could do this. And we had them go through this exercise of asking the question five times, what business are you in? You can't answer the same way twice. And the beauty of this is we ultimately got us to a place over the course of that day where we came to the conclusion that belonging anywhere was really the mantra, the definition of what differentiated us versus the Marriotts of the world. And it was that idea of belonging anywhere

that helped us to then imagine how could we edit all of the possibilities of the things we could go into. Similarly, any executive or frankly, any person could actually ask this question in a slightly different way for themselves. The question would be, what mastery do you offer or what mastery can you offer? So have a friend of yours ask that question of you five times, and you'll be sort of surprised at by the fifth time you get to ask that question, and you've had to come up with four other answers before that, what kind of revelation you may have in this archaeological dig that helps you to mine your own personal mastery? And to go back to the academy, whether that's a book on the reading list or an exercise or a practice that attendees have found particularly valuable, is there anything

that comes to mind that people at home might try or think on? Well, I think the basic premise of the academy is that in midlife, you need to sort of reframe your mindset for what's moving forward. There's a famous Carl Jung quote about you can't live the afternoon of your life the same way you did the morning. And so speaking to that, we have an exercise around evolution, evolving, because the first lesson in my book, Wisdom at Work, Making of is to evolve and it's the hardest one it's evolve is the first step evolves the first step the second step is to learn the third is to collaborate and the fourth is to counsel and we can come back to that if we want in a moment but um evolve wow what does that mean it really means learning to

edit what is no longer serving you so So we do a lot of different exercises around the idea of liminality, which is being in between two things. For people who might recognize liminal, subliminal. Yes, exactly. Subliminal messages. So a liminal is sort of right there, and it's sort of in between two things.

It's the transition that, frankly, a caterpillar to a butterfly, the cocoon, is the liminal state. People don't like to be in a liminal state. When you're a kid, you're used to it because everything's in between. Everything's in between. You know, going from crawling to walking,

you know, going from pre-puberty to an adolescent and teenager. But when you're an adult, you don't like to be liminal. And yet we have all these transitions in midlife that actually make us feel liminal. So we do this exercise where there's a whole counter full of name tags, empty name tags. 40 of them are actually empty. 120, we've written different kinds of mindsets, ways of perspective, or ways of identifying

yourself that aren't serving you anymore. Now, if you were to do this on your own, no one's going to write those for you. You'll have to write these yourself. But the process of this was, the process of what you can do is, you actually write down anything from, you know, my body is falling apart, or I'm never going to meet the love of my life. So they're in part beliefs that are no longer serving you. That's right. Millennials rule the world. There's a variety of different things we have there.

And then people a lot of times use their own name tags. And what we do is the crescendo of this experience that afternoon is people slap up to six different name tags on their chest. We go around a room. The name tags that are already filled out. As well as the ones they filled out themselves. I see. And if they have one that they can't find, then they fill out the empty tag.

Exactly. And so then you go around a room. And you could do this with four friends. And you go around the room and look at each other's name tags. And then you ultimately have a conversation one-on-one or in a small group about why these aren't serving you anymore and how you're going to be willing to get liminal and try transitioning into something new. And so as a result of that, we end the afternoon with a little fire pit. We don't walk on any coals or anything like that. We just have people write down what's the thing that

they're ready to evolve out of that's no longer serving them. And it could be some of the examples of things are like, you know what? My sense of my success in my career will no longer be my sense of success in life. That's an example of something saying, okay, I'm going to put that in the fire and then let it burn. So that's an example of a specific kind of exercise we do. We do a lot of mindfulness exercises as well in terms of helping people to calm their nervous system.

Can I pause for one second? Yeah. So the up to six tags on the chest, do you participate in this exercise? I do. Would you be willing to share some that you've burned? Well, one of the ones I've... Yeah, I mean, since you've heard my health diagnosis,

I said, like, I've recently been given a scary health diagnosis, and I feel a little lost. So that would be an example of a name tag. Another name tag would be, yeah, you know, I think I might never meet the soulmate that I met six years ago and no longer in that relationship. I am in the relationship, but it's turned into a different kind of relationship. Another one could be, another one that I've written and then ultimately burned is, it's time to take down the scaffolding of my ego.

So what does that mean? It means like over the course of my teen years and growing up, you build an ego. We sort of create this container. And our ego can be a very healthy thing. It can actually create the separation. It's the thing that actually helps us to know who we are. But it is a bit of a scaffolding. And like what I mean by taking down the scaffolding of the ego

is really sort of saying behind that is something that's really amazing it's a soul it's a heart it's and i'm no longer going to let my ego sort of be the thing that i lead with uh and how and then i you know come up with a list of things, how that shows, what are the practices or ways of being that actually have to change in order for that to be the case? So those are some examples,

just off the cuff. I wish I had a list right here. Do you have people prepare for the time at Modern Elder Academy in any way? Or do they show up and that's sort of time zero when things begin? Well, they've got to read the book, Wisdom at Work, The Making of Modern Elder.

And they do two exercises. One, which is an identity cleanse, where they actually talk to their friends about what parts of their identity work and what parts of their identity don't work so well. So they actually get some feedback. And this is before they arrive. And then they do a values inventory of like, what are the values that are most important and stack ranking them. So they try to get clear

going into it. What are the values? Now, later in the week, they often go back to that list and say, my God, now that I've had some time to think about this, my values list is a little different. And so they ask themselves, then how can they, or we ask them and we work with them because after people leave that group of 12 to 18 people in the cohort, they literally, for some of the groups, have a weekly Zoom call every single week. So they're sort of accountability partners and people who can sort of help them say, okay, yeah, you said your values, you know, number one value was this and, you know, now it looks like it's not there anymore. What's going on?

So that's part of what happens too. What would be example values that people might then put in order? An example could, I mean, some of the most obvious ones are family, religious beliefs, making a difference in the local community or trying to change the perspective on climate change.

So those are some of them. There's other ones which are sort of like ways of being, which are feeling free. So some people would say that's not a value, but that's sort of a way of being. Yeah, it could be a way of being, a priority. Yeah, so that's what they are. So it's a mixture of, I would say, values and ways of being. And we have a list of 60 of them,

and they come up with their top five and then stack rank those top five. And then over the course of the week, we don't force them to go back to it, but there's some exercises we do that allow them to, on their own, sort of look and see how those have changed. Would you be open to talking about family for a few minutes? Yeah. Okay.

Let's do it. I would love to hear some backstory that I don't know and then have some questions about current day. Yes. So you are openly gay. Yes. So you are openly gay. Yes. Have you been openly gay kind of from the get-go, or when did that become something that you felt comfortable publicly disclosing? I was 22 when I came up, and dated women, girls. I was very actively sexually in my high school.

But I knew behind the scenes, there was something there. I grew up with a father who I love. Both my parents are still living there, 81. But my dad was Stephen Sr. I was Stephen Jr., the chip off the old block. And my dad was a captain in the Marine Reserve, hardcore dude. And I was the oldest and the only boy. And so I was meant to be like the, the mini version of dad. So the, my process of being Eagle Scout, like my dad, all American water polo player at, you know, in high school and then playing water polo at Stanford, um, student body president, all this stuff was like, I was on the path to be just actually my dad and I talked about this recently.

He said, Chip, all I wanted you to do is be a better version of me. And that was so interesting to hear that. I always knew that was the case, but I never heard him. That explicit. And so it's 81 years. It's like, dad, I know. And that like fucked with my mind. So I did everything I could to sort of just be this better version of dad.

And then I was in a fraternity at Stanford. And that's where it started messing with my mind, being in a fraternity with a bunch of guys who I had some attraction to. But I wasn't doing anything about it. And I was dating a couple different women. And it was in between my first and second year of business school. I was 22 years old, living in New York, working for Morgan Stanley, investment banker by day, and at night, walking into my first gay bar. And that's when it was like Wizard of Oz, Munchkinland. It went from black and white to Technicolor. I was like, oh, wow. Well, this feels a little more-

This may be a thing. Yeah, this may be a thing. But back then, wow. I mean, I came out the summer that Newsweek had the cover story about the gay cancer. They called it AIDS. And so it was a really, really not an easy time to come out. Certainly not an easy time to come out in terms of the world that we live in today compared to then in terms of, um, especially someone who's like,

you know, hardcore business guy. Um, and, uh, so when I started my company at 26, you know, people knew I was gay and that was sort of an unusual thing to have sort of a

founder, CEO, uh, of gal. I was, I was living in San Francisco and it was a boutique hotel company. So that made it a little easier. Um,

and yeah, so I've, uh, ever since age 22, pretty just uh you know been uh you know an out really gay man and have had two two long relationships and uh now have a couple of sons with a lesbian couple so i wanted to ask you about that next so how did how did that about? So the women live in Houston. Laura's been a longtime friend of mine. And she asked me, her timing was perfect. She asked me three weeks before I was selling my company,

Joie de Vivre. And I was like the mama and the papa of Joie de Vivre. So I didn't have a co-founder, ran it for 24 years, knew almost everybody in the company, 3,500 employees. I had a lot of parent energy that had gone into my company. And I was wondering like, wow, what's going to happen when I step away from that? And three weeks before we made it public that I was actually excelling, she approached me. And I'd been approached before by lesbians who wanted my sperm, but I'd always said no. And so this time I said yes. And so the idea was, frankly,

they're going to be in Houston. I'll be the sperm donor. I don't have any legal rights, financial obligations. And we'll see how it goes in terms of whether the boys or the kids, boys or girls, will know who their dad is. So it was that sort of like, okay, I mean, it's pretty transactional, although, you know, probably a little bit more like, okay, maybe it'll be more than that, but let's see it as we go. Well, they ended up, the two women ended up having two boys. And more than anything, I think the women who, you know, they live in the state of Texas. And so the rules around this were tough. Texas is a little bit more of a conservative state. And so there was some worry that, okay, well, I'm the

real biological dad. And so can the non-biological mom be a mom? And long story short is we got to a place where it was beautiful. They knew that my intentions were not to be the full-time dad or to even be in a co-parenting role. I was there to be the boy's dad when I'm there. And I'm there a moderate amount. And they come down to Baja a lot. And it's been beautiful. And it's been a great way to give these boys a lot of love and, in essence, three parents instead of two.

Number of different follow-up questions. So the first is reflecting on something you said, which is, I'd been asked before, and I'd said no. So I had been asked a few years ago by a very close friend of mine if I would be a sperm donor for his sister who had just gotten out of a very long relationship, who'd been kind of strung along by a guy until she was in her late thirties. And I thought very, very seriously about it. And I'd never considered it before, thought very seriously, was going to do it. And then had a friend of mine who has had at that time one young child, now has two. And he said, Tim, if you do that, you are going to need and want to be involved in some fashion. I know you well enough, it's not going to sit well with you. You're not going to

be able to go hands-free. And so I decided not to do it. Why did you change your mind? Why did you say yes in this case and no in previous cases? Well, I think this idea that literally I had, I psychologically analyzed myself and I thought, I really have had a lot of parent energy being the mentor and almost father figure for so many people in the company. And that was going to change. And I didn't necessarily understand what kind of gap that would create in my life. So the timing was perfect. So I understand your point of view.

And yet I was in a place where there was a part of me that was thirsty for it. And because the women were so self-sufficient about how they wanted to do this, I figured, okay, let's see it. And I didn't know whether it was going to turn out as it's turned out, which is I'm much more integrated in the boy's life. How did that come to be?

I think it was partly because they ended up having two boys. And if they'd had the two girls, let's say, I'm not sure if it would have been different. My thinking is it might have been different. I think the fact that they're boys, like they want their dad and they want to go pal around with dad on the beach and things like that. I think that had some influence maybe, although we've never talked about that. But more than anything, you just start loving these kids. Now, I had had a foster son.

When I was 28, I became a foster parent to a 13-year-old from the Tenderloin, that district where my first hotel is, whose father's black, mom's white. And basically, he ended up homeless because his parents were just not very responsible. And so I had had an experience of being a parent, but it was a really unusual experience. It was me and my partner, my Israeli partner, who I was with at that time, and is one of my best friends now. And here's this kid who's darker skinned, who's straight, at age 13, moving in with two white gay men. And it was perfect for a sitcom. It taught me a little bit about parenting in the early days. Very different experience though. But I do think that this idea

of having younger people who need your tutelage and love helps us get out of our ego. It is absolutely, there's no doubt that, you know, it's a Zen practice to actually be with a little child and they take all of your attention. So, but I, you know, I think it's been certainly the process of how we define and create family has certainly evolved a lot in the last three or four decades. How are you thinking about parenting in the sense that are you going instinctive? Have you read books on the subject?

You know, there's some blogs that I've seen in the past and at the end of the day, the instinctive to me is best. But that, you know, between stimulus and response is important because it's really easy to be reactive with a kid who's just acting out. Sure. It's a little more complicated in my case because I'm not with the boys every day, whereas the moms are. And so I also don't want to pull rank and sort of do anything that suggests their approach to parenting is not my approach. So I'm pretty much instinctively trying to work

with their approach as well. There's a beautiful Dan Gilbert Ted talk about the fact that we all underestimate how much change is ahead of us at every, frankly, at every different era of our life. So I think the idea of embracing liminality and sort of saying, yes'm moving to austin yeah yes a couple years ago i'm moving to baha uh and so when you embrace it and you sort of see it as just the nature of life it allows for it to allows you for you to see some of the secret beauty in some of the things you're you're you might be resisting so i would say I'm still liminal. I would say the chapter-wise,

I do think my process of moving from being in the trenches, helping to run Airbnb for four years, and then two years now as a strategic advisor, huge change in terms of my day-to-day living when I was day-to-day there versus just sort of advising Brian and the founders on things now. So I'd say that was a healthy change.

But I don't know. More than anything, I'm just curious. Peter Drucker taught me that curiosity is the elixir of life. And I really believe that. And I think that the thing that makes a modern elder different than a traditional elder is a traditional elder was about being revered. It was about reverence. You revered your elder.

You respected your elder. It's not about reverence anymore. It's about relevance. And relevance requires understanding the modern day world, not just spouting wisdom that sometimes is timeless and age old, but it's actually knowing how to fit that age-old wisdom into the context of modern-day problems. And so I think if I can spend the rest of my life being both curious and wise almost simultaneously,

that is the potent alchemy that will make me hopefully a very happy person, but also someone who can actually influence other people in positive ways as well. Curious and wise and maybe also unrushed so you can watch that oil in slow motion going down the stairs. Yeah, yeah. Or watch the whales. You know, nature is such a teacher. I gotta say, I mean, being here in Austin, there's some really beautiful natural parts of Austin, and I think anybody who doesn't get romanced by nature

on a regular basis is missing that lyrical sense of what life is meant to be. Yeah, definitely. So I have just a few rapid-fire questions. They don't require rapid-fire answers, but I always like to ask at least a handful of

these. So the first one, outside of your own books, what book or books have you gifted the most to other people and why? Well, other than Man's Search for Meaning, which is probably my number one gift. Recently, the last couple of years, there's a book called The Hundred Year Life The Hundred Year Life written by a couple Brits and it sort of says imagine the future where the average person lives to a hundred how is that going to change on a personal and societal

basis it's a really interesting observational book The Happiness Curve which we talked about earlier the U-curve of happiness is what we call it, but the name of the book is by Jonathan Rauch, is called The Happiness Curve. That's become a favorite to gift. I also love Danny Meyer, The Restaurateur. And he's got one of the best books on hospitality ever written, which is called Setting the Table. Yeah, so Danny Meyer. What's the list?

I might be getting, I guess we will certainly have Shake Shack for that. Union Square Hospitality Company. Union Square Hospitality. So he's got everything from Gramercy Park. Gramercy, that's what I was looking for. Because a friend of mine used to work on the line there, actually. Gramercy Park. Fascinating, fascinating guy.

Yeah. Gramercy Park. Fascinating, fascinating guy. Also, some good sort of philosophical food to chew on, right? I mean, practical and philosophical in terms of, let's say, eliminating tipping. Well, speaking of philosophical, thank you. Marcus Aurelius' Meditations. I have given that away to a number of people. There we go. And maybe Seneca. There's a Seneca book about the short life.

Yeah, on the shortness of life. On the shortness of life. You know, one of the things he says in that book is he says something about the fact that it's not so much the shortness of life, it's how we waste it. Yeah. And I think there's something to that in terms of what percentage of your life is being spent wasted. Also, a longevity thing that I've been thinking about lately is imagine what age you're going to live to. And the online longevity sites say, I'm going to live until I'm 98.

And then ask yourself how much of your adult life, if you start counting at age 18, is still ahead of you. In fact, for me, at age 58, I'm at halftime if I live to 98. And when you start realizing you're only 50% of your way through your adult life, you take up surfing at 56 or 57. You take up Spanish, which I'm doing now because I live in Mexico

part of the time. Better learn Spanish. Mi Español es muy malo. So, yeah. Or you write two-thirds of the books that you are going to write in your life as Peter Drucker after 65. Yeah.

If you could put a word, a message, a quote, a question, anything non-commercial on a billboard, metaphorically speaking, to get it in front of billions of people, is there anything that comes to mind that you might put on that billboard? Well, you mentioned Oscar Wilde earlier. I think one of my favorite quotes of all time

is, be yourself, everyone else is taken. Yeah, that's a great one. So that would be my Oscar Wilde quote. I would probably slap up there. You know, I don't know. I think the thing I probably would, yeah, I'd probably stick with that. Be yourself, everyone else is taken. Chip, this is so much fun. Yeah. It's really nice to see you again. Yeah, it'd probably stick with that Be yourself, everyone else is taken

Chip, this is so much fun It's really nice to see you again It's great to be here It's going to be the first of many times Not necessarily on this show, but just hanging out Oh yeah, we're neighbors at this point And people can say hello on Twitter At Chip Conley

Facebook, Chip Conley Author LinkedIn, Chip Conley SF And we'll link to all this in the show notes. So for people who are watching or listening to this at tim.blog forward slash podcast, you can find links to all of this. If you just search for Chip. Also, you have moderneldernacademy.org

that people can check out. Anything else, parting comments, thoughts, suggestions, anything you'd like to mention before we wrap up? I think I would just finish by just saying that the more we fear aging, the more we're playing on the playing field of the youth. And there's nothing wrong with that. But if your intent is to just stay looking young the rest of your life, you're playing on the wrong playing field. It's a losing battle at some point. And some of us are embarrassed to see people who continue to play on that playing field.

What I think people need to recognize is whether it's the depth of our emotions, the depth of our spiritual connection with ourselves and something bigger than ourselves. These are the things that actually start to grow as we age. And it's part of the reason why we get happier as we get older. Yeah. And you mentioned the anxiety equals, let me get this right. Don't stop.

Don't tell me. It's anxiety equals uncertainty times hopelessness. Powerlessness. Yes. And that ties into Marcus Aurelius really nicely as well because it's's in a sense this stoic philosophical system certainly as practiced by Marcus Aurelius

entailed a lot of separating what you can control from what you can't and the possible from the inevitable and certainly it's hard to think of someone offhand who thought of death and mortality more than Marcus Aurelius, but learn to befriend it in a way and not to fight something that sort of left to become this amorphous source of anxiety can really be paralyzing when, as you're doing right now, learning to embrace it and live in the liminal. Embrace the elder. There you go. Own the word. I'm trying to bring back the word. Elder. And separate from elderly, which is, to me, that's the last 10 years of your life.

Well, for now, modern elder. Chip, thank you so much for the time. Thank you, Tim. It's great to be here. Really fun. And to everyone listening and anybody watching, thank you for joining us. And until next time, be well, be safe, experiment often, and learn to live in the liminal. Pick up surfing or Spanish or something else that you've been putting off because it's not too late. Thanks, everybody. Hey, guys, this is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering

over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to 4hourworkweek.com. That's 4hourworkweek.com all spelled out and just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it.