#374: Chip Conley — Building Empires, Tackling Cancer, and Surfing the Liminal

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Welcome to another episode of the Tim Ferris Show, you sexy little kittens, you clever makers, and everyone in between. My guest this episode is Chip Conley, so who is Chip? Chip and I have known each other for a very long time. At age fifty two, after selling the company he founded and ran as CEO for twenty four 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, and

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 best selling 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 uh learn all about Chip and say hi to him on social media at ChipConnley on Twitter, Chipconley Author on Facebook.

and Chipconley SF on LinkedIn. So without further ado Please enjoy my wide ranging conversation with Chip. Conley. My friend Ship.

Welcome to the Tim Ferriss Show. I'm so happy to be here! So we've known each other a long time. Yes. And it's so nice to see you again and I'm thrilled that we're able to coordinate uniforms with our respective tailors. We will be busking downtown Austin later today for change. Uh where you are a New citizen. Yeah. Or will be very surely. Yeah. It's a beautiful town. Yeah, it really is. And Uh you know, I thought we would start

And this may seem somber, but since this is something we're just catching up with Uh maybe an hour ago over lunch. I Can you talk about your current

Medical. State of affairs. If you wouldn't mind, because I th I think it's a wedge that leads us into discussions That can be pretty far ranging. Sure. If you wouldn't mind. Uh no, no problem at all. Um On the second day of a book tour.

Five months ago. before I was at a Ted speaker's dinner, so day before giving a spe TED talk, I found out I I have intermediate stage prostate cancer. And it came as a complete surprise. My urologist had said after doing a biopsy, probably a twenty percent chance you've got a problem here. But as it turns out, it's not a

I had a problem. And so Since then have had a few different tests and the good news uh 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 t the cavalry across the plantation to To sort of say yes, y you know, probably I'm young enough, I'm fifty eight. Probably gonna live another thirty to forty years. Probably will have my prostate taken out in the next

Couple years. What is uh what is that? feel like to you to realize or to say? And what is that for people who may not know, like what does that mean? I mean it's prostate like an appendix, you don't really need it. Well, you there it does have certain functions w which we can get graphic and get into if you want to. Um but let me say the first of all the big C the you know, the the cancer word is like wha w what? I have Cancer and

That the good news is prostate cancer as cancers go is actually a a rel 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 uh part of it's 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. Um It does mean you still could potentially have an orgasm.

Uh but you um you just will have a dry orgasm. This is really Crazy to be talking about this in the first five minutes. I feel like so late. This is like the mirror, you know, it's like the French cover, you know, naked nanny or something like that. We're skipping the four. This is this is how we, you know, keep you uh on the the podcast for an hour and a half. Um All I can say is um Cancer can be a teacher. Yeah.

And for me it's been a uh A reminder of the vulnerability that we can have. Uh 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 of days ago, the test results had looked really good.

Now there's a test result that's uh 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 it 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. uh in life. I had a flat line experience. where I went to the other side ten and a half years ago and that did the same thing for me. So That was in St. St. Louis. That was in St. Louis. Thank you for the memory on that one. Yes, it was in St. Louis and I had was had been going through a difficult time.

and had a broken ankle from a bachelor party with Gavin Newsom. Um and I had a cut on my leg w which had a bacterial infection in it, uh because Gavin had his bachelor party at eighteen D 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 um so

So I've had a couple of experiences of just being a wake up call, which is an interesting term for a hotel year. To have a wake up call and sort of say you know what? You are still alive. Um but are you living your life the way you want to live your life? And the reason I 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 ten years, probably more. I've been struck by how aware you strive to be of your thinking. And how many times you have uh changed chapters very deliberately.

And so I thought this could be A s a segue into conversations about some of those chapter changes and how you thought through them and also just impactful Uh periods. in your life. Yeah. And I thought maybe uh if you're willing to I think it was a quote

I could be getting this wrong, so feel feel free to fact check, but the Shakespeare quote was it that you shared when we were having lunch, which I think it's appropriate. The meaning of life Is to find your gifts. And the purpose of life is to give it away. Uh 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. Yeah.

But 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 that I think I've that's been very much embedded in my heart and a soul and my mind.

Over My Thirty five, thirty seven years of Being in the business world. And for people who who aren't familiar

With with chip. Uh what is 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 the speaking engagements often is this is the guy who's disrupted his favorite industry twice. And that happened industry happens to be hospitality. I was one of the first boutique hotel years along with Ian Schwager and Bill Kempton. I And I started a company called Joadavive. Joatavive is based in San Francisco, created fifty two boutique hotels, second largest boutique hotel year in the U.S. And then after twenty four years of running that soon after I had my flatline experience, which was a a wake up call to say I didn't want to be running that company anymore.

I was asked uh 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 um Yeah, so I that's my I've also written five books and I most recently have created this the world's first midlife wisdom school called the Modern Elder Academy. We're gonna talk about All of this. Yeah. So many places to go. I thought we would start with one of your more glamorous periods. Could you uh tell us how you got into commercial real estate.

You know, I I grew up in California. Everybody in California has sort of like a real estate bug and um I went to work for my summer my my uncle the summer And then uh almost most of my junior year at Stanford, uh, he was a commercial real estate developer in S in Silicon Valley. This was nineteen eighty. 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 how do you design environments? And um 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 um in San Francisco for a couple of years. And then it's after Stanford Business School. And then that's when I said, you know what? The th 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 f sort of freshman sophomore year. What what did what what what did you envision adult chip doing in the past? I thought I was gonna be a philosopher.

You and I could have hung out together. Do a little Seneca, you know, Marcus Aurelius uh debate. Um before it was cool. Yeah, exactly. No, I yeah, I took a class called God's God self and the body or something like that in freshman year. And I just loved it. I so I thought ph but you know, everybody said, like what are you gonna do with a philosophy major? Um So I thought I might go into politics like helping in a in a governmental role. Um, and I went I did a summer in DC as an intern and didn't love it. And so uh business became sort of the next thing. Uh and I guess I have been sort of a philosopher in business. I certainly that's probably the reason I like writing books about it.

Um But I no, I had no idea I was gonna get into commercial real estate. And and then at twenty six, twenty on my twenty sixth birthday, I finished a business plan to create this boutique hotel company called Joadavive, 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 uh Resonated with me. And um yeah.

bought a broken down motel, pay by the air motel in the tender line called it. 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 in the course of

preparing for this uh read about Brainstorming sessions. That you did. I think they were a few hours in length. Yeah. I hesitate to say four hours because of course I'm the four hour guy, but I think that in the in the article it was four hours. Yes. Uh And there were some there were some other characters involved. You've done your research. Whose names may be recognizable. I think Seth Godin was also Seth and I wrote our first we both wrote our first books together back when we were in our second year of business school. Yeah, this group of those five guys all we're 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, uh duck. Yeah, so so we sort of create our own little club uh and we were brainstorming business ideas. And um was there a 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 have bring an idea. To the table and then we critique it. And Seth is a You know, a good critic. So that was partly how we how we 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 clute students, but once we graduate, they won't talk to us because they'll think we're looking for a job. Use that stand for while you can. And we did, and we created a book called Business Rules of Thumb, and it came out long, long, long time ago. And um Yeah. Seth at that point had caught the bug. He knew he was gonna write books. I d I hadn't caught the bug. I wasn't Until about gosh sixteen, eighteen years later that I 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 i as as well. If if people are listening and They like the idea of forming

A group like this. Yeah, because I I think that at least in the piece that I'd taken a look at The the consensus of some of the people in the group was that you learned more Through

those sessions than you did through the the coursework. Yeah. So if if People out there listening and they think they want to create their own group, whether they call it a mastermind or a brainstorm group or whatever it might be, where they have the opportunity to put people, say in the hot seat and uh 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 unnecessary 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.

Um 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 Yeah. So I think that's key. I think another thing that's key is is While it can be like intellectual jousting.

And so it can be hardcore. It there has to be at least an underlying respect. If the purpose of it is to just, you know, skewer each other. Um you know, people start to shut down or start stop showing up. Yeah. And so that's that's critical. And at the end of the time, uh, we also had a good time. I think that was a big piece of it as well. How how long did they last? They could I mean, well, we did it for the two years, but what was the purpose? What was what was the big 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. Um Some of us went to work for very entrepreneurial ventures. Um, 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 gonna actually create a business plan. I think it 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. um where people would go and uh 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. Uh There's a place called the Esselin Institute in Big Sur, and I've been on the board for uh basically a decade and I've been teaching there for a long time. It was like take that place. The bookstore is dedicated to me, thank you. Uh it is um 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 So why isn't there an Eslin in the city? And that was an idea that percolated. Ultimately it led me to buying a a a no tell motel in the tenderloin of San Francisco, which is not exactly um that idea, but I think it was year was this roughly? So eighty four is when we graduated, so when I think probably came up with that idea, and it was eighty six that I came up with the idea of Joievive and buying this motel in the inner in the tender line. So sometimes you you know, you're planting a seed.

I mean what's great about uh life is you know, your brain, your soul, your spirit, your ability to channel something deeper than you from far off in the in the cosmos, these are things that actually sometimes take time. And so planting seeds early is is wise. Well th I 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 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. Right. Don't expect to ever come back to it. Yeah. And then you plan on X, but you can't do it right away. And It seems to 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. Yeah. And how what form it'll take. So Yeah, I think for me the the thing that was really interesting is that writing that book with Seth, the second year um incubated sixteen or eighteen years later in in my first official book, which is called um The Rebel Rul Rules

Yeah. And Richard Branson wrote the foreword. And I think that for me The thing that became clear to me Was And and has been a practice my whole m 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 twenties. And I would almost do a half hour to an hour, usually on Friday afternoon, sometimes over the weekend, and said, Here are the some of my key lessons of the week. And I created a wisdom book. It was called the Wisdom Book. And that wisdom book was

The collection of lessons. that I was learning along the way. And I I it wasn't like I went to the wisdom book all that often to look at it. I did do it. In d 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 it? You still do it. I still do it. So if if I may. Yeah. Uh And today's Saturday. Today's Saturday, so I'm going to go to the house. So Friday on the flight to Austin, which I lost the flight, missed the flight. I went had to fly to Houston and then Take a a lift from Houston here.

Um I took I did my list. And this list was a really interesting list because this was a weird week. Obviously this is gonna be uh um on un out in the public in a a few weeks.

But this week was the week that a New York Times article came out about my our new Modern Elder Academy. And it 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 I've it's forced me to reacquaint myself with one of Victor Frankel's famous

Three line or three lines from Man 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 that those three sentences over and over because I was just getting more and more indignant and almost feeling betrayed by the journalist because You know. She just didn't she didn't she wasn't she didn't give a factual story. So long story short is I I this week my list of lessons

were very much about emotional regulation and which is really something that we learn as we get older. Um you know 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. Um the the bloodier the week, the more the more bullet points there are. Um The average week is about five. Five bullets. Oh look at that. On Fridays. That's interesting. Well that but my your bullets and my bullets are different. Um My Bullets are really actually lessons. You're not like here's my here's the my favorite spatula I found this week and lessons learned, no? Nothing like that. No. Um They're actually yeah, they're they're they're deep and sometimes painful. Um

This week I there were probably twelve bullets and And some of you know some of them are Like tactical things. I said to my PR person I got this article on my own.

You know, I know the auth the the journalist, um Yeah, we're not 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 And she did. But I didn't necessarily have someone there to sort of say, Hey, yeah, Chip said these things and um

Why are those not in the article? And you put something else in there that he didn't say. And so it it I think part of it for me was okay, you know, yes, it's it's normal to have Someone there as a PR specialists especially for an article as important as say the New York Times would be. Um that's another example.

You know, another one is When Things are troubled. It's the most important time for who the higher you are in organ in an organization

Two Be calm. Because Um Are mere neurons.

mean that our emotions are contagious. And so and everybody tends to look at the most senior person to see how they're reacting to something. And so when something goes askew Uh people look to the leadership to see, you know, are they Are they sweating?

Yeah. And I'm not saying that we shouldn't be authentic and transparent. And um But you can be both. Uh 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 Try to

to be that way and not, you know, get like So Wrapped up in A reaction. You know, Frankel's quote is really about reaction. Yeah. Response versus react.

And the l the longer we're on this earth often the better we get at being responsive as opposed to reactive. Practices or books. or resources, anything at all has helped you in developing your What was the phrase you used, uh not emotional resilience regulation. Yeah, um I think uh I've been lucky enough. I'm not I'm like awful at at yoga.

Um I 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 I'm really tight. I have a hard time with that. And uh but I'm really good at meditation. And I t I took to it thirty five years ago. Um And I've ha integrated 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 ten minutes. to just absolutely get into a mantra of just breathing.

And uh you know, that actually is a way of, you know, regulating myself. Clearly exercise, you know, 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 and so that's I've done that too. But I will say back to the yoga for a second. Uh I think there's

two ways that I look at life um and that's to be in at in attainment mode. trying to attain something and in an attunement mode. And what I've found is that I'm My natural tendency is very attain oriented. Yeah. And When I'm in the attain mode.

I often have to atone afterwards because Um I have sharp elbows and I'm just going for what I want. Attain or atone. Well it's attain yeah leads to atonement. Atune leads to at one. And there's 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. Uh yeah.

And attained sport, surfing, which I at age fifty-seven, fifty-six, fifty-seven, I'm fifty-eight now, I started learning to surf. Um This is not an attained sport. The key is to attune yourself to the wave.

Yeah. 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. Hm. And is your meditation practice mostly Focusing on the breath and letting arise whatever arises without trying to modify it, or what is your pr what is your internal practice look like when you sit for those ten minutes? I have a lot. So I w I've done TM and that's a twenty minute practice and that's the that's sort of my core go to that I do. Yeah, but mantra based Try to it.

morning and a afternoon. Uh at minimum I do it the morning. The uh I do a lot of other ones as well. There's a loving kindness meditation that I, you know, k sometimes will do, which s sort of when I'm I frankly when I'm most stirred up about someone in particular, I could sort of go that that that direction. I love the Vapasana, but that's more of a an extended silent meditation practice. Um and I w like right now Two years ago I was in Loreto Bay in Baja

kayaking with a guy named Mark Coleman who wrote a book called Awake in the Wild. Beautiful book. From island to island amongst whales. with a silent kayaking meditation retreat for a week. Didn't talk for a week. That was beautiful. Um So I think but but the simplest thing to do, I 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. What windows? Louvered like you know 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 Match. I was gonna say they're sort of like the uh they make me think of really old Volkswagen. Yeah. uh 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 the 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. Yeah, so that's you know but I yes, I there's

the the core thing I tend to do is the the T T M and uh for people who are interested in in the second you mentioned, which is the loving kindness meditation, also known or called meta medit M E T T A uh there are some fantastic guided meditations that you can listened to out there. Like Jack Cornfield has some fantastic versions of that. There's also a really fascinating guy named Chaid Meng Tan, who who wrote a book called Joy on Demand that that gets into this. And Search Inside Yourself too. And Search Inside Yourself. Uh which became the most popular employee class at Google at one point.

So let's let's go back to something you mentioned. Um your first book. The first book you count. How old were you when you wrote that roughly? I was thirty eight. Uh when I wrote it and um Yeah, and I had so I'd been running my company for a dozen years.

Uh Gardevive. And How did you get Richard Branson to Red Force? Great question. You know, um so Uh Gavin Newsome at that point he was the mayor of San Francisco and I uh he was my first mentee. I was I mentor 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. So it was actually around the launch of that record store, you know, it's hard to imagine. Yeah, I remember like a record store, really um Wasn't that long ago though. But um so we went there and We were there with like the head of protocol for the city. And 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 You know, 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 he 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 gonna 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 w 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 of the something. I went in the front of the 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, right? And uh 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? Did G was the next day. And we just had lunch the next day. And and the truth is that his company Verge it was just in the early stages, I think, of thinking about doing Virgin America. Uh the the airline and I was at that point the largest hotel year in San Francisco in terms of the number of hotels we had So it was there was some s 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? Uh

You know what she he had an assistant there and so and h and his assistant actually did know me and knew Gavin. So she was like w wise enough to know these are two and she said so he said Uh, can you go talk to April over there? And so we went over and talked to April and um April said, You know what? He's got some time to schedule tomorrow. And so Amazon. Yeah. And then flash forward and you have a forward from Richard Branson. So yeah, he w so I I ultimately ultimately he said, you know, I'll write it, but you're gonna write the first draft and you know, and and then he he edited it and it went in it.

Continue this. This forward and backwards chronology, if if I can even call it such. Uh Who is Brenda Lee? And this may go somewhere, it may not go anywhere, but Brenda Lee is this four foot ten inch, although she's five foot six 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 in change that much. Yeah, there's a lot there's a lot of drugs on the street and um it's a relatively poor neighborhood. Um pretty desolate, uh but it's right in the middle of the city. It's right and it's right near Union Square in the in the hotel district.

So we we were sort of we were the gateway to the tenderloin, but we were on the opposite side of the tenderloin from where the y the 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. Listen to Arlo Guthrie when I grew up. Oh my gosh, I know Arlo Guthrie. So Arlo Guthrie's in the hotel. Because the great American music hall's 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 a band's gonna appreciate. And she checks in and And all of a sudden we become a rock and roll hotel. We had Arlo Gather and Grendily, and that led to

You know, Nirvana, Pearl Jam, you know, David Bowie, red hot chili peppers, you know, everybody you can imagine staying there over the air. So 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. No, there's more to the story. No no no. So how how d okay, so they you You have Manifested or chanced upon This luck of having These two guests at the same time.

How do you how does that then get converted into a reputation? Do they just recommend to other people? Do you Seze upon that. Hey, can we take some photos? How does it have to be there was some logic so my business school brain was saying, Okay, well who's the person who books all of the Hotel rooms for bands coming through town. And and br I had gotten to know Bill Graham, who's a music uh empresario, uh concert promoter, and he had said, Well it's usually the concert, you know, whoever's booking the concert, they're doing it. So I tried to we tried to market to them. Then we tried to market to the venues, like Slims 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 markets of them.

To be honest with you, none of those worked all that well. They worked okay. This is so funny. was the person who typically made the decision of where the band was gonna stay With the

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 like doesn't show up at the show. And of course an overdose could do that as well. And he was 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 um A massage treatment room. Now back in the old days when it was a pay by the airplace, 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 Um when you bring your band here, if you t give us ten 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 b pre th cell phones.

Free Internet. Uh 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.

And in my case, figuring out that the customer was not all those other people. It's actually the tour manager. And what's that unrecognized need? It's basically to like chill and to relax. And they get a free massage. That's incredible.

And y because it it it also acts as a contrast in my mind to um A maxim that is often Often used, but I think often inaccurate, which is you Granted you had a 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. The the unspoken customer. Yeah. Right. And then no one ever said that was the term out. Yeah. And then the un the unspoken need. And the I mean the cost to offer that service. Yeah.

A rounding error. 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. Yeah. Um 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 Vitali. Sure. Which is on the waterfront in San Francisco. It's a bunch of Two of my books there. Oh, thank you. Yeah. Um Well, so long as we're sure the hotel Vitality, like the Phoenix is in like the worst neighborhood in San Francisco, and the Votali's sort of like the best neighborhood is right on the bay on the on the embark it arrow, right across from the ferry building and the and the um the farmers market. So The unrecognized need for the customer we wanted there. So the Vitality 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. Yes, the hospitality tweener who who who sort of was looking for that. And so our point of view was we said this is a person who's 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 Vitale when we launched Uh fifteen years ago. A yoga studio.

uh on the Penthouse level that had free yoga classes every morning. Now my 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. Twenty 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 on the st on the on the penthouse level. Like why would we ever do that? And I said well Because we're gonna be the first ones doing it. And so then they said, Well look at all of the customer satisfaction uh forms you've gotten from people in financial district hotels. And have they asked for a yoga studio? And the answer was no, 10,000 of them. We looked at 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 a line out the door and within a a month we had we were in You know, New York Times, LA Times. Uh, Wall Street Journal had stories about this new sort of hotel. That's oriented toward business travels who want to stay healthy.

And the h Hotel Vitalia ended up becoming the most successful upscale hotel in San Francisco. It's reminiscent to me of uh and this could be apocryphal. I don't know if this is a real anecdote. It's kinda like every quote is attributed to Abraham Lincoln or Oscar Wilde on the internet, but Did you know they had a thing, the two of them? A quote off uh Henry Ford, I think uh you know if if I had asked people what they wanted, they would have said a faster. Oh it's attributed to him at this point. To

to to look under the under the hood on that decision a little bit. So the the first is and this is something that I'm Constantly Maybe constantly is too strong a word, but I 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 like the doing something the first time is really can be really undervalued. Like the the

Being second Different story, right? Being first i can can be r very, very newsworthy in and of itself. Also, uh what would you have done if it If it hadn't worked. We would've we would have turned it into a suite. Right. I mean, so the key the key there, and it's that you just said it exactly right, which is My point to my investors was give me six months. Let me try this.

We can ratchet and make it into a suite. And Yeah 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 gonna be insurmountable if it didn't work out.

But it turned out to be it turned out to package and position the brand of the hotel really well and be something that people valued. And but I think the the point on that is to sort of say okay So w how do you try things and and Do something small enough. But that could have a big impact.

That is easily solvable if it doesn't work. Right. And which is also Uh something that could 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 uh he's been on the podcast, but Uh you've spent time with them and if you look at I believe it was Virgin Atlantic where Uh he he did 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, like you can really lose your shirt. And uh among other things, you know t 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 say it was Boeing at the time. Uh in order to be able to give them back the plan. If it didn't work. So behind the scenes Uh

He's actually making very, very calculated bets. He's a shrewd guy. Super shrewd. Yeah. And I think um You know, the one of the things I learned from my dad a long time ago is uh build the business plan as if it's not gonna succeed. I mean Imagine it succeeding and you're gonna attract people for that, for investors, uh employees. But What's plan B, you know, and and how do you how do you have a solution for for plan B? And so that's why I don't build bowling alleys. Bowling alleys sort of like in terms of the shape of them is you know you could you could said in the past churches, but churches have become sort of popular for all kinds of uses. post church era. Um but yeah, I think it's really critical to sort of understand what is plan B, C and D.

So let's let's talk about another chapter shift and I'm gonna take this opportunity to pull up A screenshot of a text exchange that I had with Mutual friend of ours with Liz. Lambert. Yes. So could you explain for peop to for people who don't know who who Liz is just for a second. So Liz Lambert hates me because she even said on your podcast she hates me because sh I I did for her what now I hope and expect she does for other people. Uh

Which is she reached out to me almost twenty years ago. I w uh had become a successful entrepreneur hotel year. A boutique ou tier and she was creating this Funky little motel here in Uh in an Austin called the Hotel San Jose.

And similar to my Phoenix. Um and she liked what we did with the Phoenix, although she was gonna do something that was a little more upscale. And she wanted my help. And so I came here and 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. And why did you do that? I 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 a a a an attorney who should never have been an attorney who's

completely amazing as a designer. So she's one of those hotel years who designs her own hotels, which I love. That's sort of like you know, th like a restaurantur where the chef is the restaurantur. So I think it's really beautiful. And um so I just loved her passion and her sense of the s you know her joie de vie, frankly. H the they should have took it such a joy in what she was doing. And I I wanted her to succeed. And so Um, you know, I am a big believer in Kermic capitalism, which means sort of what goes around comes around.

And so Uh me giving to Liz was gonna pay back to me some in some way over time. And And frankly, it's been me doing that with a lot of different people and then having it come back reputationally. You know, your reputation is one of the few things in your life that's portable. Um and frankly it ri it rives FedEx before you arri 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 Um it's just helped my reputation. in terms of how people see me and uh instead of people standing on the sidelines sort of like jeering, they're they're cheering. They they want, you know, when when the New York Times article came out this week and I didn't love it, I had a such a support network of people who just said, You know what, we're gonna 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 restaurant tour, um 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 are sort of silently happy. And I don't 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 um as such, uh Liz was just an example of that.

And uh and the part reason she hates me is because now she feels the obligation to pass it on, pay it forward to someone else because she gets, you know, hit up all the time because she's a she's just an amazing uh hotelier. She's really incredible. And uh she's got Bunkhouse. Bunkhouse. And she has uh s a number of just incredible Not just incredible properties, but incredibly different properties. They're they're soulful. You know, at the end of one of her pools, you know, the St. Cecilia pool here in in Austin just has you know the neon soul. And there's something soulful to her places uh Uh, and so I I want to bet on people like that.

Yeah, there there are a lot of parallels that I can see. Uh. looking at the two of you side by side in some ways. And I just just struck me that I did a number of staycations at uh Hotel Vitale to work on books. Because I think I had read that Maya Angelo had 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. He'd go to a hotel room and just shut shut himself off for a week and to actually figure out um music. No kidding. So I have I have friends here.

Uh I'll I'll 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 so I'm gonna 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, ship began building Joie de Vive as a young man. It was the work of the first half of his life, a big sprawling family. What made him decide to sell it when he did?

Mm. So uh great question. You know the One thing, you know, to you aspiring entrepreneurs and uh 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 h hotel before I had 52. And that one hotel when people come up to me and say, How you doing, Chip? I said, Well, the Phoenix is doing fine. And finally somebody called me on it. It's like, you know, 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 I fortunately over time I realized that w didn't have to be the case. And it was that flatline experience I had uh twenty two years into running my company. That helped me to see That

Uh, is this what I want to do the rest of my life? Actually it's not. And I thought it was gonna be, but it wasn't. And more than anything, I just realized that I started the company. for creativity and freedom. That's w those are the things I r said to myself, um

on one Friday afternoon when I said, Well, what did I learn this week about why I'm starting this business? And twenty two years later, I said, Do I have any creativity and freedom in this business anymore? No, I'm like running a company with thirty five hundred people. So that's what led me to it was hard though. It was h very hard to sell a business That for a You know, Ultimately when I sold it, it was twenty four 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, you know, 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 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 spa. They didn't like it and But at the end of the day it was the right decision. So that As you just said.

It sounds like a a difficult decision, uh or a uh maybe emotionally Intense. decision to work through. And I mean I remember when this was kind of happening and uh and y you mentioned just in passing here, you know, I d I decided what I want to do 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 I I made the decision I had this was gonna kill me if I kept doing it. And so I knew I needed to move on. I didn't know where and and frankly then you get into the freaky it was the in the Great Recession, the freaky thought of like how am I gonna sell this company in the bottom of the m recession. So I w I hadn't yet found the new thing I was moving toward.

I knew what I was moving away from. But moving towards 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. Yeah. Because they actually didn't move towards something. They just moved away from something and they just sort of sort of like almost you know just

Uh wasting their time. Yeah, they're just in a void. They stepped into a void. They stepped into a void. And so I 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, thirty six festivals in twenty countries in one year. And um that helped me. You have a great blog post on TimDot blog about some of your experiences at these festivals. I do. I that's right. Exact yeah. So I Loved, loved that process and it did help me move to towards next. Plus I wrote another book. I wrote a book called Emotional Equations that did well, became a New York Times bestseller. And it was another thing that just said, listen, like this is my new identity. I'm you know, I've 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 you mentioned the emotional equation. So I I remember this. And could you explain despair equals suffering minus meaning? Yeah. When I had that flatline experience and and to just give I was in St. Louis giving a talk Um 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 the year. Where were you when this happened? I was in did you make it to the hospital before you flatlined? No. So I was I so I was I was giving a speech on crutches, which is one First first sign that Chip should have s been staying in bed and not been on this book tour trip was like, Yeah, well I was on crutches on stage giving a speech. So I didn't fortunately I did not fall over Uh at the speaker as I was standing up at the at the mic. But I sat down signing books and that's when I slumped in my chair and then they put me

I probably didn't have a flat line experience there. I just went unconscious for three minutes. Fortunately the Paramedic showed up a couple minutes later, uh really quickly and They put me on a gurney and they had put heart monitors on me, and that's the first time of nine times that I went flat line and they had to get the paddles out. The first time uh I they didn't have to use them. Uh about five seconds later my my heart came again. But over the course of the next ninety 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 I long story short was not do long story short. You can't do a long story short on near death experiences. What did you see on the other side? There isn't, by the way, a festival of the the near de a pilgrimage of the near death. experience in s in Spain. Spain has the weirdest festivals in the world. Um What I saw was this. And it the fact that it happened over and aga 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 um sunroof or uh Skylight.

And light Uh is pouring in the skylight beautiful Light. Um And

It's pouring in in such a way that there's actually this Viscuous oil, very heavy oil on the ground. on the most beautiful wood grained uh floor you've ever seen. And it's ca because the the 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 colours. Uh on the wall. And so What I see is light. I see colours and I see this weird this franjapani scented.

oil Going down these stairs. And that's what I kept seeing. And I never saw anybody else, didn't see f anybody on the other side. I what I saw myself is observing almost floating above this. I felt incredibly peaceful and everything was moving very, very, very slow motion. So um

And I you know, I kept coming back to that. And I don't really I've never actually sat down with with like a dream analysis or anyone to sort of say what does it mean? Like the fact it's it stairs going downstairs means I may be going to hell. Um but actually it was up I was up in a mountain chalet way up toward heaven. I don't I don't know. All I know is you know, forget about heaven and hell. What I know is in that moment I felt beauty. And Calmness. Like

I'd never felt before him. So Yeah. That so the W what did you make of that?

Like I mean I'm not saying it there there is no whether if you had a Freudin Freudian dream analyst here and they said, You know what that means, let me tell you, I'd be like bullshit. Come on, like you can give us your opinion. Exactly. It's how would you what would what did you What do I take from it? Yeah. Well I what I take from it. How I want to honor and experience beauty.

In my whole life. You know, I d um the gods of efficiency, which I tend to tend to be my religion. Um these gods of efficiency have a tendency to force me or or have its way with me in terms of just getting uh very clipped in how I do things because I have to like get all these things done. And you know, being clipped and doing things doesn't allow for the time to sort of Yeah, 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.

Um and how do I take time, you know, to do you know, fasting Day three to 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 Uh

the calmness I felt. So no no fear of like okay, you know, I'm I'm dying and it's just gonna be terrible. There was that. But I think the thing that was m most interesting was just the fact that the oil was moving so slowly. It's like there's a there's a catch up commercial anticipation a long time ago, maybe Heinz fifty seven catch up. 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 in a

uh in a room at the hospital in St. Louis. And weirdly enough, in my backpack Um that I'd brought with me on this chip. was Man Search for Meaning, Victor 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 is my insurance agent

Whose name is Chip had committed suicide four months earlier. Um 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 The meaning of that book, Manstrict Meaning, and turn it into a An equation

And the way I thought of it is suffering is sort of a constant if you're a Buddhist, and I sort slightly am Uh If you're y 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

inner uh they're sort of inversely proportional to each other. So if you do the math of like okay Suffering uh disparity qu suffering minus meaning eight equals ten minus two. If you take Two and turn it to four. then eight becomes six. Right. And so despair goes down when meaning goes up.

And this is when I realized that that practice I've had since you know being a twenty three year old of writing my what my lessons were for the week was a practice that actually was giving me meaning. And that's that Equation. Which I came up with that night.

Well, I ended up teaching it to all of our leaders in the company as we went into the great recession. Um And Ultimately I said. Darn it, I went to to Bhutan to study the gross national happiness index because I wanted to see what what's the happiness, you know, 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 eighteen equations that sort of help you make sense of your emotions. Whether it's um happiness or d or disappointment. Um or wisdom.

Are there any other equations that you find yourself referring to or thinking of more often than I'd say a couple of uh the anxiety ones very relevant in the business world, and that's anxiety equals uncertainty times powerlessness. So it's not a plus, it's it's a times. So the uncertainty and the powerlessness together i 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 is it where you can w what how 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? I mean, 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 is reality? And if uh the disappointment is more predominant than the reality, then you know, they're gonna there's gonna be I'm sorry, if the expectations are high And reality is low, disappointment is what can uh will come from that. So Um and those b both of them are negative. The happiness one I in that I learned in in Bhutan was uh happiness equals wanting what you have. divided by having what you want.

Wanting what you have speaks to gratitude. Uh having what you want is the process and uh of gratification. So it's not to say this is not the ex this so uh so it says gratitude's better than gratification. Well that's fine if you're a Buddhist. That's fine if you don't wanna go out and attain, attain, attain. I wanna go out attain and I wanna go gratify. But

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 tread 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 greyhounder on the track just sped up a little bit. We know that one. Okay We occasionally we go there. Well, you know, it's it's you, me, Liz, and a few million people who might

Be listening to this and speaking of this, this ties in very, very nicely. Yeah. Uh So y both you and Liz are Very thoughtful. Uh and m 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. Uh was I noticed the chip has made a few life changes, selling Joie de Vive.

uh Airbnb. Um you're 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 uh

Yeah. How do you how do you begin to Think about that. Um I want to wring her fucking neck. No, I'm not I'm kidding. Um But this is I think something that a lot of people who have become good at achieving. Struggle with.

Oh, totally. Um You know, I Peter Goober. I I got to interview him on stage. He's one of the the actually you know Peter Goober. Yeah, we've been we actually have both been in in his box um at the Warriors games. Um I interviewed him on stage and this guy's twenty 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 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 um so What I took from that and what I take from Liz's question is Is

I think the the real question here is not whether You're going to Just Be still. I love being still. I the fact I'm a meditator, the fact that I have chosen to live in Baja, California, an hour north of the

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 uh anymore.

And Um Yeah, I 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 Joadaviv. 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 um Then I joined Airbnb. Because the the founders asked me to. And all of a sudden

I'm not, you know, I I was the tiny version of Richard Branson in my company. But now I'm like instead of being the stage on the stage, I'm the guide on the side. I'm helping these three uh 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 seventy hour a a week kind of thing. Not four hours a week or whatever you've been able to perfect was. Uh yeah. So I uh 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, um you know the reality is, yeah, it's it is me being driven again. But I've put guardposts on it. I'm doing it in Baja, I'm doing one location, I'm not doing multiple locations. So you you feel comfortable with that commitment.

I feel com yeah, no, I am. Actually and frankly the cancer, you know, for those who you didn't hear earlier on the thing, I I've got cancer. The cancer sort of was another uh 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, you know, our aspirational aging ahead of us. I think all that's important. No one's done that yet. There's all 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 rate on that. Well midlife, it doesn't have to be age, but how would you How does someone know if they're in midlife is is is they're in crisis. Is it a plot? Yeah. No, you know, midlife has historically been defined as either 40 to 60 or 45 to 65. The truth is the the the phrase midlife crisis was coined in nineteen sixty five. And the reason it didn't exist before then was because longevity in the US was forty seven years old in the year

nineteen hundred and it became seventy seven by the year two thousand. We we gate we added thirty years of longevity in one one century. So what happened is this new era of life sort of Got Right. It's not it's not yet fade to black. It's like no, you have another half the movie to go. Well you do it. And the the thing that happens in midlife and w how do 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 you know sort of invisible name tags that define who you are in the world. Um And you actually, frankly, are sort of feeling overwhelmed. by all of that accumulation. There's this reset that happens in midlife.

And and you could say, frankly, with the millennial generation, it might happen actually earlier in life. It might happen. At thirty five. Frankly, in Silicon Valley, it absolutely happens in the mid thirties. When especially if you're an engineer, um, where you feel like, wow, I am no longer you know, I'm no longer perceived as you know an up and comer. And in a in an industry that, you know, is like the entertainment industry or fashion. Yeah, or professional sports. Yeah, exactly. So you so I think personally midlife is from thirty five to seventy five. And part of the reason I think and I think it used to be just forty five to sixty five, it's it's happening younger.

Because of the fact that people feel irrelevant earlier. in you know the digital intelligence that we desire in companies mean that there's a greater and greater desire to hire the new digital natives. And And I think it's gonna last longer midlife because if we're gonna live to a hundred, which is sort of the the future, uh you know, as a longevity we're we're at in the right around eighty right now. But by the by the time we get to the end of the century, I uh it I think we'll be about a at a hundred at for longevity in the US. That means at age seventy five, you're probably still working.

Yeah. And at least you know, 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 Uh go into midlife. And not think of it life as being just a one tank journey. Like you fuel up with all of your you know, education and support

Up to age twenty or twenty five, and then you drive this vehicle that we call our bodies. for the rest of our life and at midlife you're you're starting to run on fumes And you need a you need a pit stop. And so um the modern Elder Academy is the idea of that pit stop. And I think it's going to

Help to create a n a new category of Academia a or even hospitality real estate, which is the midlife wisdom school, just like Canyon Ranch forty years ago, Mel Zickerman. overweight accountant from LA. wanted to go to a place to be get healthy and all the places that he saw forty years ago.

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. Spa 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

When I see something like that and I can see that I can be a social entrepreneur that's actually trying to Um fix a societal ill, which is ageism and people getting stuck in midlife. I'm gonna do that and in this case I'm doing it You know, as a social entrepreneur with a social enterprise we're

sixty percent of the people are on scholarship. So I'm funding a million dollars a year in s in scholarships. That 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 gonna ask. Yeah. So like Burning Man created a bunch Burning Man created a great idea, and so there's a bunch of ten principles festivals around the world. Eselin. Great idea nineteen sixty two.

led to you know a hundred personal growth retreat centers. Got it. The Academy is a proof of concept. A 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. I do think when you say 'Cause I could 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 or a loosely Uh Organized a affiliate

Uh 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 like limiting it to one location, does uh is there uh is there a footnote to that? Thank God for cancer. Yeah. Honestly, I um The path that you're talking about?

Oh I was in con I was in the And in discussions on a third location. When I found out about my cancer. On the second day of the book tour, uh right before, you know, uh 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.

I said and I keep saying no The thing I will do 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 here's how we can do it. You know, I I don't want to make it

Yeah, 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. You know, aging is not something that we aspire to. And and yet there are a lot of

Real ple unexpected pleasures of aging. Is do you know that do you know oh god, let's talk about this. So your 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 Russia people get happiest after they die. It's a statistical error, clearly, but there's something to that. Um every other country in the world that has been studied

The what they show is the following from about age twenty five to about age forty five. Uh between forty five and fifty, depending on the country. З а слоне на happiness. because of that accumulation, because of that collection of things that we start to do that prepare us for midlife. And

Then between forty five and fifty, there's this what Brene Brown would call the uh unraveling. Uh another Texan. She's in Houston. Oh yeah. Uh she might even be here. She might be in Houston now because her daughter's here. Yeah, exactly. So um 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 is Leads people to get to a place. where they get happier with each successive decade.

So people are happier in their fifties their than their forties. They're actually happier in their sixties than their fifties. And they're happier in their seventies till uh than their sixties. Men start to flatten out in their happiness in the second half of their seventies. Women It starts happening in the early eighties. So in essence what it's saying, because women women live longer than men, is there's a point at which five to ten years before you die, you actually start to maybe get a little bit less happy. Because there're ten

There can be you know acute uh 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. Um 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, Tim. The aging brain doesn't have recall or uh is not as quick as it used to be. But the th a lot of people don't know about the aging brain is it gets more adept at doing left brain, right brain tango. Which w means basically the 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

Yeah. To the creative right ba brain. much more easily. More adeptly. And what does that lead to in terms of a positive? Uh it lead to being able to s 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 you they just heard. An older person can do that better than a younger person. Younger person is bet much better at doing focused. So Why is that relevant? Well, in the you know, let's talk about Airbnb for a moment. At Airbnb, when I joined six years ago, we had th 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 and it was you know, maybe one twentieth of the company decides today. We had thirty initiatives, strategic initiatives in the year two thousand thirteen when I started And nobody in the company, including the founders, could actually recite all of them.

So Later that year we did an off site retreat in New York and I said to the leadership team, w 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 gotta get down to four. So for two thousand fourteen, we're only gonna have four strategic initiatives. And so we spent three days arm wrestling over that one, twenty three different potential Initiatives that we were gonna do.

And it was that kind of distilling down. I think But How did you do that? Because I think a lot of people listening maybe even one person sitting here talking, i.e. myself. Uh Struggle with

long lists of prospective or current projects. Yeah, for sure. Right. So here you have a fast growing, very, very fast to me an understatement growing startup. Yeah. And they have a list of how many? Twenty something? Who knows? Yeah, twenty twenty three that we twenty three initiatives that the twelve members of the strategic initi uh st uh of the leadership team thought should be okay our our potential for 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. 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. Um you know, twenty years older than I was twenty one to twenty three years older than all three founders.

Um, but I think what they appreciated was there was an element of I think a modern elder versus a traditional elder. is 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 that those three days in New York where we sort of said, Okay

So what is it that we want to be when we grow up? We wanna 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.

Uh there are a lot of natural sharing economy. Uh businesses that could be created. Um, 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 ten 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 Viv era. when I was running my boutique hotel company. When we were trying to figure out what's our differentiator

Versus Marriott or even Kimpton, another boutique hotel company. We actually imagined the idea that um we could ask the question what business are we in. because the number one Harvard business school biz Harvard Business Review uh reprint of all time.

uh came from uh an article from nineteen sixty 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 We took that idea of what business are we in and we turned it into a little bit of a game. The idea was uh we would be asking

executives or l senior leaders to ask themselves that question Um So one person would sit facing the other. The person asking the question would say, What business are we in? And the 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 this the per second person, the person answering could a not answer the same way twice. And if you do that five times, it really almost is like an archaeological dig to figure out the essence of your company. What's your soulful differentiator as an organization? Um, this is how we found out that we were in the identity refreshment business at Joadavive, and it was this same idea. uh that uh we applied to airbnb.

when it came to uh an offsite retreat, we did relatively soon after I joined the company. We sat our executives in pods of two. Um So they couldn't hear each other. Any company could do this. And we a 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 uh 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 marriottes 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. Um similarly any executive or any freaking any person. could actually the 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 uh 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 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 you know, the basic premise of the Academy is that in midlife you need to sort of reframe your mindset. Uh there's a famous Carl Young quote about it. Uh, you can't live the afternoon of your life the same way you did the morning. And um so speaking to that, we have an exercise around evolution evolving, because the first lesson in my book, Wisdom at Work, The Making of a Modern Elder. is to evolve. And it's the hardest one. It's evolve is the first step. Evolve is 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. Um Evolve. Wow, what does that mean? It really means learning to Edit. What is no longer serving you.

So we do a lot of different exercises around the idea of liminality. Um which is it being in between two things. Liminal subliminal. Yes, exactly. Subliminal messages. So a liminal is sort of I'm uh right there and it's sort of in between two things. It's the transition that frankly a 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 prepuberty to an adolescent and 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 limal. So we do this exercise. Where there's a whole um Counter full of name tags, empty name tags.

Forty of them actually are empty. We've written different kinds of Mindset, ways of perspective or ways of identifying yourself that aren't serving you anymore. Now if you were to do this on your own, you no one's gonna write those for you. You'll have to write these yourself. But the process of this was

Іно май бади і фалин апарта. Or I'm I'm uh Never gonna meet. the you know love of my life. So the they're impart beliefs that are no longer serving you. That's correct. Millennials rule the world. Yeah, there's a variety of different things we have there. And then people a lot of times use their own uh name tags

And what we do is the the crescendo of this experience this after that afternoon is People slap like u up to six different name tags on their chest. We go around a room. The name tags that are already filled out. 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 with like four friends. And you go around the room sound. 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 gonna be willing to get liminal and try transitioning into something new. And so as a result of that Um, we end the afternoon with a little fire pit. We don't walk on, you know, 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 uh it could be Some of the examples of things are like, you know what? my sense of my success in

In my career Will no longer Um that's an example of something saying, Okay, I'm I'm gonna put that in the fire and then let it burn. So That's an example of a specific kind of exercise we do.

Um 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. W would you be willing to share some that you've earned? Well, one of the ones I b uh yeah, I mean I you know, it was since you've heard my health diagnosis. I say like I've recently been given a 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 um Yeah, I you know, I I think I might never meet the soulmate that I met six years ago. and no longer in that relationship. Uh I am in the relationship, but it's it's it's turned into a different kind of relationship.

Um another one could be um another one that I've uh written. And and then ultimately burned is um It's time to take down the scaffolding of my ego. So what does that mean? It means like o 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

Uh like what I mean by taking down the scaffolding of the ego is really sort of saying Behind That's 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 w how that shows how what are the practices or uh ways of being that actually

uh have to change in order for that to be the case. Mm-hmm. So those are some examples just off the cuff, I'd I wish I had a list. Do you have do you have uh people prepare for The time at Modern Elder uh Academy. Yeah in any way, or do they show up and that's sort of time zero when things begin? They've gotta read the book, Wisdom at Work to Making of Modern Elder, and they do two exercises. One which is an identity cleanse where they actually talk to their friends

What parts what parts of their identity work and what parts of their identity don't work so well. So they actually get some feedback and then 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, Oh my God Now that I've had some time to think about this, my values list is a little different. Um and so they ask themselves then how can they H we ask them and we w we work with them. Because because after people leave that group of twelve to eighteen 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 And people who can sort of help them say, Okay, yeah, you said your values, you know, number one value is this and Y you know, now it looks like it's not there anymore. What's going on? Um, so That's part of what happens too. What uh what would be example

Values. that people might then put in order. Um, a an example could I mean s some of the most obvious ones are family, uh, religious beliefs, um making a difference in the local community or the or you know, trying to change the perspective on climate change. So these are there those are some of them.

Uh the there's other ones which just are like ways of being, which are Being Feeling free. So that that's not ex I th some people would say that's not a value, but that's sort of a way of being. It could be a way being priority. Yeah. So those are this that's what they are. So it's a mixture of I would say values and ways of being. Um

And we have like a list of sixty of them and then they come up with their top five and then stack rank those top five and And then over the course of the week we we don't n force them to go back to it, but there's some exercises we do that allow them to on their own sort of look at see and see how those have changed. Would you be open to talking about family for a few minutes? Yeah. Okay. So I would I would just love to hear your Uh some backstory that I don't know and then uh have some questions about uh current current day. Yes. Uh so you are openly gay. Yes.

When w have you been openly gay kind of from the get-go, or when when did that sort of publicly that you felt comfortable publicly with you. I was twenty two when I came up, so I was I was and dated women Girls. You know, I I was very actively sexually in my high school. Um

And So But I knew behind the scenes like there was something there. Uh I grew up with a father who I who I love. He's he both my parents are still living there eighty one. But my dad was Steven Senior, I was Steven Junior, the chip off the old block

And my dad was a captain in the Marine Reserve. Hardcore, you know, 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 the stuff was like

I was on the path to be just Actually My dad and I talked about this recently. Um 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. So it's eighty one years saying I was like, Dad, I know. And that like fucked with my mind. Um so I did everything I could to sort of just be this better version of dad.

And then in I was in a fraternity in at Stanford And that's where it started like messing with my mind being in a fraternity with a bunch of guys who Um I had some attraction too, but I wasn't doing anything about it. And I was dating a couple of different women. And it was in between my first and second year of business school. I was twenty-two years old, living in New York, working for Morgan Stanley, you know, investment banker by day.

And at night. walking into my first gay bar. And that's when it was like, you know, like Wizard of Oz Munchkin Land, you know, 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. And and so um But you know, back then, wow, I mean I came out the summer that Newsweek had, you know The the pa the cover story about, you know, the gay the gay cancer, the they called AIDS. And so it was a really, really not a 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 I when I started my company at twenty six, you know, people knew I was gay and that was sort of an unusual thing to have sort of a founder, CEO. Uh I was I was living in San Francisco and as a boutique of talk company, so that like that made it a little easier. Um and yeah, so I've uh ever since age twenty two pretty much 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 uh next. So how did how did that come about? So The women live in Houston. Laura's been a longtime friend of mine. And um

She asked me it was her timing was perfect. She asked me Three weeks before I was selling my company, Shira Viv. Uh and I was like the mama and the papa of Joad Aviv. So I didn't have a co-founder, ran that for twenty four years. knew er almost everybody in the company, thirty five hundred employees. I had a lot of

that had gone into my company. And I was wondering like wow, what's gonna happen when I like step away from that? Uh And three weeks before uh I we made it. public that I was actually excelling.

Um She approached me and I'd been approached before by lesbians that wanted my sperm. Um that uh, you know, but I'd always said no. And so this time I said yes, and I And So uh the idea was, frankly, um They're gonna 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 k the boys or the kids boys or girls will know So is that that sort of like okay, I mean it 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 um more than anything, I think they the the women who You know, they live in the state of Texas and so the rules around this are were tough. It's it t Texas is a little bit more of a conservative state. Um and so there was some worry that okay, well, I'm the 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 they're they knew that I my intentions were not to to like 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, you know, a moderate amount and they come down to Baja a lot. And it's been beautiful. It's and you know, it's been a great way to give these boys a lot of love and in essence three parents instead of two. So the the first is a Is reflecting on

Something you said, which is I've been asked before And I said no. So I 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 kind been kinda strung along by a guy until she was in her late thirties.

And uh 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 uh had at that time one uh young child now is two, and he said

Tim, if you do that, you are going to need and want to be involved. in some fashion. Like it's not I know you well enough. It's not gonna sit well with you. Like you're not gonna be able to go hands free. And so I decided not to do it. Uh

Why did you change your mind? Like why did this why did you say yes in this case and no in previous cases? Well I think this idea that literally I had my I I psychologically analyzed myself and I thought I really have had a lot of parent energy. being the mentor and you know, almost father figure for so many people in the company. And that was gonna change.

Uh and I didn't n necessarily understand. what kind of gap that would create in my life. So the timing was perfect. So I understand what your your point of view and yet I was in a place where There was a part of me that was thirsty for it. Yeah. Um And because the the women were so self sufficient about how they wanted to do this

I figured okay it You know, let's see it. I didn't know whether it was gonna turn out as it's turned out, which is um much more integrated in the boys' life. How did that come to be? I think it was partly because they ended up having two boys and I I think you know and the and if they'd had the two girls two girls that say, I'm not sure if it would have been different. I might think 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. You know, uh I think there that had some influence, maybe, although we've never talked about that.

Um but more than anything I just you know, you just start loving, you know, these These kids I now I had had a foster son When I was twenty eight. I became a foster parent to a thirteen year old from the tenderline. That that district where my my first hotel is.

Um, who's whose father's black, mom's white, and you know, basically he ended up homeless because his parents were Um Just not 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 um I was with at that time and is one of my best friends now. And here's this kid who's uh darker skinned moving who's straight at age thirteen, moving in with two white gay men. And it's like it was perfect for a sitcom. It taught me a little bit about parenting. In the early days, um very different experience though. Uh So I but I do think that this idea of

having younger people who need your Tutelage and love. Um Helps us get out of our ego. It is absolutely you know, there's no d doubt that, you know, it's a Zen practice to actually be with a little child um and they take all of your attention.

Mm. So but I I I you know, I think it's been Certainly the process of how we define and create family. has certainly evolved a lot.

uh in the last three or four decades. How are you thinking about Parenting in the sense that are you are you going instinctive? Are you have you been have you read books on the subject? You know, I've I've I there's lot there's some blogs that I've seen in the past and I I at the end of the day, it the instinctive to me is best. But I but that you know be between stimulus and response is important because it's really easy to be reactive with a kid who's just acting out and um It's a little more complicated in my case because I'm not with the boys every day. Uh whereas the the the moms are. And so I also don't want to pull rank.

And sort of uh do anything that's that suggests their approach So I'm pretty much instinctively trying to work with with with their approach as well. Uh you know, there's a beautiful Dan Gilbert TED talk about the fact that we all underestimate how much change is ahead of us at every at frankly at every different era of our life. Um So I think I the idea of embracing liminality and sort of saying yes.

I'm moving to Austin. Yes, couple years ago, I'm moving to Baja. Uh and So Uh 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 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, the 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 on things now. So I'd say that was a a a healthy change. Um But I don't know. More than anything, I'm just curious. I yeah, I Peter Drucker taught me

That curiosity is the elixir of life. And I really believe that. And I think that the the thing that makes a modern elder different than a traditional elder is a traditional elder was About It's about reverence. You revered your elder you respected your elder.

It's not about reverence anymore, it's about relevance. And relevance requires um understanding m the modern day world. Um 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. Uh curious and wise and maybe also unrushed, so you can watch that oil in the oil going down the stairs. Yeah. Yeah. W or watch the whales. You know, nature is such a teacher. I 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 romance by nature on a regular basis.

is missing that lyrical sense of what life is meant to be. Yeah. Definitely. So I've just a a few rapid fire questions. They don't require rapid fire. Answers but I I always like to ask at least a handful of these. So the the the first one outside of your own books.

Uh what? book or books have you gifted the most to other people, and why? Well, other than man search of for meaning, which is probably my number one gift, uh uh recently, the last couple of years, um, there's a book called The Hundred Year Life.

It sure says Imagine the future. Where the average person lives to a hundred. How is that gonna change on a personal and societal basis? It's a really interesting observational book. Um the happiness curve, which we talked about earlier. Um it's a b uh the the U curve of happiness is what we call it, but the name of the book is by Jonathan Rausch is called the happiness curve. That's become a a favorite. Uh

to gift. Um I also love Danny Meyer, The Restaurantur. Yeah. Um and he's got and he's got one of the best books on hospitality ever written, which is called um Setting the table. Gram yeah, so so Danny Meyer What's the list? I might be getting uh yes we we'll certainly have Shake Shack for that. Yeah.

Union Square hospitality and discussed everything from Grammarcy. That's what I was looking for.'Cause a friend of mine used to work on the line there, actually. Grammar Sea Park. Uh fascinating, fascinating guy. Yeah. Uh also uh Some good uh Sort of philosophical. food to chew on, right? I mean practical and philosophical in terms of let's say eliminating philosophical thank you. Marcus Aurelius Meditations I have given that away to to a number of people. There we go. Yeah, you may be Seneca. There's a Seneca book about um

But the short life. Yeah on the shortness of life. Yeah, one of the things he says in that book is he says uh It 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 like what um what percentage of your life is being spent wasted. Also I l a longevity thing that I've been thinking about lately is like Imagine what age you're gonna live to. And uh on uh the online legivity site say I'm gonna live till I'm ninety eight. And then ask yourself how much of your adult life, if you start counting at age eighteen, is still

ahead of you. Uh in fact for me at age fifty eight I'm at halftime if I live to ninety-eight. And when you start realizing You're only fifty percent of your way through your adult life. You take up surfing at fifty six or fifty seven. You take up Spanish, which I'm doing now because I live in Mexico part of the time. Better learn Spanish.

So uh Yeah. Or are you right? Two thirds of the books that you are gonna write in your life as Peter Jucker after sixty five. Yeah. Uh if you could put a

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. So that would be my Oscar Wilde quote I I would probably th slap up there. Um You know, I don't know. I think the 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's great to be here. And it's gonna be the first of many times, not necessarily on the show, but just hanging out. Oh yeah. Oh yeah. We're we're neighbors at this point. And people can say hello on Twitter at Chipconley. Facebook Chipconly author. LinkedIn, ChipConley SF and we'll link to all this in the show notes. So for people who are watching or listening to this uh at tim.blog forward slash podcast. You can find links to all of this if you just search for chip. Also you have modern elder academy dot org. Mm-hmm.

That people can check out. Anything else? Parting comments, thoughts, suggestions, anything you'd like to mention before we've got the I think I would just finish by just saying that um The more we fear aging. uh the more we're playing on the playing field of the youth. And there's nothing wrong with that.

Um but if you Um If 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 w some of us are embarrassed to see people who are 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 it's part of the reason why we get happier as we get older. Yeah. And you mentioned the anxiety equals let me get straight. Don't stop don't don't don't tell me. It's anxiety equals uncertainty times hope. Powerlessness. And uh that ties into Marcus Aurelius really nicely as well because it's uh In a in a sense, you know, s the st 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 um Certainly it's it's hard to think of someone offhand who thought of death and mortality more than Marcus Aurelius. But but learn to befriend it in a way. Yeah. And not to to fight something. Uh 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 like bring back bring back the word. Elder. And and separate from elderly, which is to me That's the last ten years of your life.

Yeah. Well for now, modern elder. Uh Chip, thank you so much for the time. Thank you, Tim. 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 uh learn to live in the liminal. Pick up surfing or Spanish or something else that you've been putting off'cause 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? And 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 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 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 fourhourworkweek.com, that's fourhourworkweek.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.

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