The Tim Ferriss Show Transcripts: Chip Conley

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Please enjoy this transcript of my interview with rebel boutique hotelier and New York Times best-selling author Chip Conley (@chipconley), who, at age 52, after selling the company he founded and ran as CEO for 24 years, received a call from the young founders of Airbnb, asking him to help grow their disruptive start-up into a global hospitality giant. He became their head of global hospitality and strategy.

Chip’s latest book, Wisdom @ Work: The Making of a Modern Elder, inspired him to build the world’s first midlife wisdom school. Located in Baja California Sur, the Modern Elder Academy provides the place and the tools to start reframing a lifetime of experience for what comes next.

Transcripts may contain a few typos—with some episodes lasting 2+ hours, it’s difficult to catch some minor errors. Enjoy!

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, Castbox, or on your favorite podcast platform.

Watch the interview on YouTube.

#374: Chip Conley — Building Empires, Tackling Cancer, and Surfing the Liminal
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Tim Ferriss: My friend Chip!

Chip Conley: Yes, Tim!

Tim Ferriss: Welcome to the Tim Ferriss show.

Chip Conley: I’m so happy to be here!

Tim Ferriss: We’ve known each other a long time.

Chip Conley: Yes.

Tim Ferriss: And it’s so nice to see you again. And I’m thrilled that we were able to coordinate uniforms with our respective tailors. We will be busking in downtown Austin later today, for change, where you are a new citizen.

Chip Conley: Yeah, I love it.

Tim Ferriss: Or will be very shortly. Yeah, it’s a beautiful town.

Chip Conley: Yeah, it really is.

Tim Ferriss: And I thought we would start, and this may seem somber, but since this is something we’re just catching up with maybe an hour ago over lunch, can you talk about your current medical state of affairs, if you wouldn’t mind? Because I think it’s a wedge that leads us into discussions that can be pretty far-ranging.

Chip Conley: Sure.

Tim Ferriss: If you wouldn’t mind.

Chip Conley: No problem at all.

On the second day of a book tour five months ago, the day before I was at a TED speakers dinner, so the day before giving a TED talk, I found out I have intermediate stage prostate cancer. And it came as a complete surprise. My urologist had said, after doing a biopsy, “Probably a 20 percent chance you’ve got a problem here.” But as it turns out, I had a problem.

And so, since then, I’ve had a few different tests and the good news is I’m right on the cusp of serious versus not serious. So far, we’ve just looked at the alternative health approach, but I’m all about Western medicine when I need to bring the cavalry across the plantation to sort of say, “Yes, I’m young enough. I’m 58, probably going to live another 30 to 40 years, probably will have my prostate taken out in the next couple of years.”

Tim Ferriss: What does feel like to you, to realize or to say? For people that may not know, what does that mean? Is a prostate like an appendix? You don’t really need it?

Chip Conley: Well, it does have certain functions which we can get graphic and get into, if you want to.

But let me say, first of all the big C. The cancer word is like, “What? I have cancer.” The good news is that prostate cancer, as cancers go, is actually a relatively tame cancer. But that was hard.

And then, prostate. The prostate. Women don’t have a prostate. Men do. And it has a little bit to do with sexual functioning. Actually it’s more to do with the secretion that happens in semen. So if you have your prostate taken out, you’re no longer going to ejaculate. It does mean you still could potentially have an orgasm. But you just will have a dry orgasm.

This is really crazy to be talking about this in the first five minutes. Feel like salacious — this is like the mirror, inside the French cover, Naked Nanny, or something like that.

Tim Ferriss: We’re skipping the foreplay.

Chip Conley: This is how we keep you on the podcast for an hour and a half.

All I can say is cancer can be a teacher.

Tim Ferriss: Yep.

Chip Conley: And for me, it’s been a reminder of the vulnerability that we can have. As well as what level of control you do have over your body. And so the fact that I’ve been focusing on making myself healthier, and so far, until a couple of days ago, the tests results had looked really good.

Now there’s a test result and a PSA score that shows that it’s spiked a little bit, so we’ll have to see with an ultrasound this next week.

But I think more than anything it just forces us to ask ourselves, or forces me to ask myself, “What am I here on this earth to accomplish, and to experience?” And it creates a certain level of urgency in life. I had a flatline experience, where I went to the other side, 10 and a half years ago, and that did the same thing for me.

Tim Ferriss: That was in St. Louis.

Chip Conley: That was in St. Louis, thank you for the memory on that one. Yeah, so it was in St. Louis, and I had been going through a difficult time. I had a broken ankle from a bachelor party with Gavin Newsom, and I cut up my leg, which had a bacterial infection in it, because Gavin had his bachelor party at AT&T 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.

So I’ve had a couple of experiences of just being a wake-up call, which is an interesting term for a hotelier, to have a wake-up call and sort of say, “You know what? You are still alive. But are you living your life the way you want to live your life?”

Tim Ferriss: And the reason I thought this could be as good a place as any to start, is that in all my interaction with you, from the very beginning, which goes back at least 10 years, probably more, I’ve been struck by how aware you strive to be, of your thinking. And how many times you have changed chapters very deliberately. And so I thought this could be a segue into conversations about some of those chapter changes and how you thought through them. And also just impactful periods in your life.

Chip Conley: Yeah.

Tim Ferriss: And I thought, maybe if you’re willing to, I think it was a quote, I could be getting this wrong, so feel free to fact check, but the Shakespeare quote —

Chip Conley: Oh, yeah.

Tim Ferriss: — that you shared when we were having lunch, which I think —

Chip Conley: It’s beautiful.

Tim Ferriss: — it’s appropriate here.

Chip Conley: “The meaning of life is to find your gift. And the purpose of life is to give it away.”

Now it’s actually sometimes being called Shakespeare, it’s sometimes called Picasso. Picasso has a great quote too, that relates to Modern Elder, which is: “Computers are useless; they only give you answers.” We’ll come back to that one.

But yeah, the idea of finding your gift, the meaning of life is to find your gift. The purpose of life is to give it away. And I think that’s been very much embedded in my heart and my soul and my mind, over my 35, 37 years of being in the business world.

Tim Ferriss: And for people who aren’t familiar with Chip, what is the introduction, the context you’d like to give, or if it’s easier, how would someone introduce you at a speaking engagement?

Chip Conley: Well, the way they introduce me at the speaking engagements often is: “This is the guy who’s disrupted his favorite industry twice!” And that industry happens to be hospitality. I was one of the first boutique hoteliers, along with Ian Schrager and Bill Kimpton. I started a company called Joie de Vivre. Joie de Vivre is based in San Francisco. Created 52 boutique hotels. Second-largest boutique hotelier in the U.S.

And then, after 24 years of running that, soon after I had my flatline experience, which was a wake-up call to say I didn’t want to be running that company anymore, I was asked six years ago by the three young founders of Airbnb to come join them and take their little tech startup and turn it into a global hospitality brand.

So I have been a disruptor twice. And yeah, I’ve also written five books. And I most recently have created the world’s first midlife wisdom school called The Modern Elder Academy.

Tim Ferriss: And we’re going to talk about all of this.

Chip Conley: Yeah.

Tim Ferriss: So many places to go. I thought we would start with one or your more glamorous periods. Could you tell us how you got into commercial real estate?

Chip Conley: I grew up in California. So everybody in California has sort of the real estate bug. And I went to work for my uncle the summer, and almost most of my junior year, at Stanford. He was a commercial real estate developer in Silicon Valley. This was 1980. It was full of orange groves. Silicon Valley was nothing like it is today.

And I just saw everybody making money and having a good time in commercial real estate. What I was fascinated by was the creative side of it. How do you design environments? And ultimately I went to Stanford Business School straight out of undergrad, and focused on real estate there. And then went to work for a real estate developer in San Francisco for a couple of years. And then I —

Tim Ferriss: And that was after Stanford —

Chip Conley: That was after Stanford Business School. And then, that’s when I said, “You know what? The part of real estate that’s really interesting is hotels.”

Tim Ferriss: What did you think you were going to do as an undergrad? Did you know real estate was the answer? Let’s say freshman-sophomore year. What did you envision adult Chip doing in the world?

Chip Conley: I thought I was going to be a philosopher. You and I could have hung out together.

Tim Ferriss: Well, yeah, well you are kind of a philosopher.

Chip Conley: Do a little Seneca, Marcus Aurelius debate.

Tim Ferriss: Before it was cool.

Chip Conley: Yeah, exactly. No, yeah, I took a class called God, Self, and The Body or something like that, freshman year. I just loved it. So I thought philosophy but everybody said, “What are you going to do with a philosophy major?”

So I thought I might go into politics, like helping in a governmental role. And I did a summer in DC as an intern, and didn’t love it. And so business became sort of the next thing.

And I guess I have been sort of a philosopher in business. Certainly that’s probably the reason I like writing books about it. But no, I had no idea I was going to get into commercial real estate. And then on my 26th birthday I finished a business plan to create this boutique hotel company called Joie de Vivre, which is a really impractical name for a company, especially in the U.S., because it’s hard to pronounce. Hard to spell. Most people don’t know what it means. It means “Joy of life.” But very few companies in the world have a mission statement that’s also the name of the company.

And that’s what really resonated with me. And yeah, bought a broken-down motel, pay-by-the-hour motel in the Tenderloin, called it The Phoenix and it became a rock and roll hotel and a big sensation and that’s how I got started.

Tim Ferriss: If we back up a little bit and revisit Stanford Business School. In the course of preparing for this, read about brainstorming sessions that you did. I think they were a few hours in length.

Chip Conley: Yeah.

Tim Ferriss: I hesitate to say four hours, because of course I’m the four-hour guy, but I think that in the article it was four hours.

Chip Conley: Yes.

Tim Ferriss: And there were some other characters involved.

Chip Conley: You’ve done your research.

Tim Ferriss: Whose names may be recognizable? I think Seth Godin was also one.

Chip Conley: Seth and I, we both wrote our first books together, when we were in our second year of business school. Yeah, this group was five guys. We were the five youngest guys in the class. Two of us went straight into business school. The other three had one year off.

And we were sort of not well-liked, generally, within the business school class, because we were just the innocent, naïve dumbshits.

Tim Ferriss: Fresh off the boat.

Chip Conley: Yeah. So we sort of created our own little club. And we were brainstorming business ideas. And —

Tim Ferriss: What there a format to it? Did you guys meet on a regular basis?

Chip Conley: We met on a regular basis and it was really the best way to describe it, each one of us would bring an idea to the table, and then we’d critique it. And Seth is a good critic.

Tim Ferriss: Yeah, he’s a very good critic.

Chip Conley: And so that was partly how I got to know Seth and ultimately Seth and I didn’t love business school, and so our second year of business school, we said, “Why don’t we write a book, get credits for writing the book, use that experience to go out and interview a bunch of famous people who will talk to us because we’re business school students, but once we graduate they won’t talk to us, because they’ll think we’re looking for a job?”

Tim Ferriss: Use that Stanford while you can.

Chip Conley: And we did. And we created a book called Business Rules of Thumb, and it came out a long, long time ago.

And yeah, Seth at that point had caught the bug. He knew he was going to write books. I hadn’t caught the bug. It wasn’t until about, gosh, 16, 18 years later that I wrote what I consider my first book. I don’t actually count that book as one of my five books, unfortunately. I don’t think Seth counts it as well.

Tim Ferriss: If people are listening, and they like the idea of forming a group like this —

Chip Conley: Yes.

Tim Ferriss: Because I think that at least in the piece that I’ve taken a look at, the consensus of some of the people in the group was that you learned more through those sessions than you did through the coursework.

Chip Conley: Yeah.

Tim Ferriss: So if people out there are listening and they think they want to create their own group, whether they call it a mastermind or a brainstorming group or whatever it might be, where they have the opportunity to put people, say, in the hot seat and —

Chip Conley: Yeah.

Tim Ferriss: — and have their ideas critiqued and to offer the same, do you have any guidelines or recommendations on how to do that well? Or what the necessary ingredients are?

Chip Conley: Well, I think the most important thing is to have clarity about what the purpose is. That’s sort of true in life and true with any business, but it’s actually true with a group. And so the fact that we knew this was a brainstorm around business ideas, mostly entrepreneurial ideas, was absolutely clear.

If you don’t have that clear, then people are using it for different purposes. And it’s fine to have different purposes, as long as people know each other’s agenda. So I think that’s key.

I think another thing that’s key is while it can be intellectual jousting, and so it can be hardcore, there has to be at least an underlying respect. If the purpose of it is to just skewer each other, people start to shut down. Or stop showing up. So that’s critical.

And at the end of the time, we always had a good time. I think that was a big piece of it as well.

Tim Ferriss: How long did they last?

Chip Conley: They could — we did it for the two years —

Tim Ferriss: And what was the purpose? What was the —

Chip Conley: 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. Some of us went to work for very entrepreneurial ventures. But I think what we really wanted to do was incubate some interesting ideas, such that in that second year of business school we might determine if we were going to actually create a business plan.

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

Tim Ferriss: The bookstore is dedicated to you.

Chip Conley: The bookstore is dedicated to me, thank you. It is because I gave some money — that’s the only reason, not because I’m a great author, or anything like that.

The bottom line is I said, “Why isn’t there an Esalen in the city?” And that was an idea that percolated. Ultimately it led me to buying a no-tell motel in the Tenderloin of San Francisco, which is not exactly a bad idea. But I think it was —

Tim Ferriss: What year was this, roughly?

Chip Conley: ’84 was when we graduated, so when I think probably came up with that idea. And it was ’86 that I came up with the idea of Joie de Vivre and buying this motel in the Tenderloin.

So sometimes you’re planting a seed. What’s great about life is your brain, your soul, your spirit, your ability to channel something deeper than you from far off in the cosmos, these are things that actually sometimes take time. And so planting seeds early is wise.

Tim Ferriss: This is part of the reason I wanted to ask you what you thought you might be or what grabbed you as an undergrad? Maybe I’m forcing a narrative but I don’t think so. Because I’ve seen this before, in that you have philosophy, it grabs you. It has great appeal but you don’t know what to do with it at the time, so you bookmark it.

Chip Conley: Right.

Tim Ferriss: And don’t expect to ever come back to it.

Chip Conley: Yeah.

Tim Ferriss: 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.

Chip Conley: Exactly. The question is timing.

Tim Ferriss: Yeah.

Chip Conley: And what form it will take.

Yeah, I think for me, the thing that was really interesting is that writing that book with Seth, the second year, incubated 16 or 18 years later in my first official book, which was called The Rebel Rules: Daring to be Yourself in Business. And Richard Branson wrote the foreword.

And I think that for me, the thing that became clear to me was, and has been a practice my whole business career, is making a weekly inventory of what I learned that week, has been essential. And I think that every Friday afternoon, I started doing it when I was in my mid-20s. And I would almost do a half hour to an hour, usually on Friday afternoon, sometimes over the weekend, and said, “Here are some of my key lessons of the week.”

And I created a wisdom book, and it’s called The Wisdom Book, and that wisdom book was the collection of lessons that I was learning along the way. And it wasn’t that I went to The Wisdom Book all that often to look at it. I did do it. In dark times, I would go there. But generally it was just the act of putting it down that was planting a seed in my consciousness to take notice.

Tim Ferriss: When did you stop doing that? Or did you stop doing it?

Chip Conley: I still do it.

Tim Ferriss: You still do it?

Chip Conley: I still do it.

Tim Ferriss: If I may —

Chip Conley: Yeah. And today’s Saturday.

Tim Ferriss: Today’s Saturday, so what —

Chip Conley: So Friday on the flight to Austin, which — I missed the flight. I had to fly to Houston and then take a Lyft from Houston here. I did my list.

And this list was a really interesting list because this was a weird week. Now obviously this is going to be out in the public in a few weeks, but this week was the week that a New York Times article came out about our new Modern Elder Academy.

And as people have said, “It’s a great article.” But it’s not really very accurate. And to my mind, a great article is very accurate, so I don’t love this article. And it’s forced me to reacquaint myself with one of Viktor Frankl’s famous three lines from Man’s Search For Meaning. And so that went into my lessons this week, which was: Between stimulus and response there is a space. In that space is the power to choose your response. And in your response lies your growth and your freedom.

And I had to really watch, look at those three sentences over and over, because I was just getting more and more indignant and almost feeling betrayed by the journalist because she didn’t give a factual story.

So long story short is this week my list of lessons were very much about emotional regulation, which is really something that we learn as we get older. There’s a lot of things that, as we get older, 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.

Tim Ferriss: How long is, say, the total set of bullets for this week? Is it a page? Is it two pages?

Chip Conley: It depends on the week. The bloodier the week, the more bullet points there are. The average week is about five.

Tim Ferriss: Five bullets?

Chip Conley: Five bullets of — oh.

Tim Ferriss: Oh, look at that.

Chip Conley: On Fridays — oh, wow.

Tim Ferriss: Five-Bullet Fridays!

Chip Conley: Wow, that’s interesting! But your bullets and my bullets are different. My bullets are really actually lessons. Yours are —

Tim Ferriss: You’re not like, “Here’s my favorite spatula I find this week” and your lessons learned? No.

Chip Conley: No, no. Nothing like that. No. They’re actually deep and sometimes painful.

This week there were probably 12 bullets. And some of them are tactical, things like —

Tim Ferriss: Are you willing to share any of them?

Chip Conley: Yeah. Like one of them was I said to my PR person, “I got this article on my own. I know the journalist. I wouldn’t say we’re friends, but we know each other moderately well. And I think she’d probably prefer just the one-on-one.” And she did.

But I didn’t necessarily have someone there to sort of say, “Hey, yeah, Chip said these things. And why are those not in the article? And you put something else in there that he didn’t say?” And so I think part of it for me was, “Okay, yes, it’s normal to have someone there as a PR specialist, especially for an article as important as, say, The New York Times would be.”

That’s another example. I gave the Frankl’s example. Another one is: When things are troubled, it’s the most important time for whoever, the higher you are in an organization, to be calm. Because our mirror neurons mean that our emotions are contagious. And everybody tends to look at the most senior person to see how they’re reacting to something.

And so, when something goes askew, people look to the leadership to see: Are they sweating?

Tim Ferriss: Yeah.

Chip Conley: I’m not saying that we shouldn’t be authentic and transparent. But you can be both vulnerable and a visionary at the same time.

Tim Ferriss: You can also be very serious and calm at the same time.

Chip Conley: Yeah, for sure.

Tim Ferriss: If need be, yeah.

Chip Conley: So I think that I’ve tried to be that way and not get so wrapped up in a reaction. Frankl’s quote is really about reaction. Response versus react. And the longer we’re on this earth, often the better we get at being responsive as opposed to reactive.

Tim Ferriss: What other practices or books or resources, anything at all, have helped you in developing your — what was the phrase you used? Not emotional resilience, regulation.

Chip Conley: I think I’ve been lucky enough — I’m awful at yoga. People say, “Oh, you got the yoga body, you sort of seem like you’re a yoga guy.” And it’s like, “No, I’m really tight. I have a hard time with that.” But I’m really good at meditation.

I took to it 35 years ago, and I’ve integrated it into my life ever since then. And I would say a morning practice of just meditating, as well as sometimes an afternoon practice, or a practice when I’m most stirred up is to just close my eyes, give myself 10 minutes to just absolutely get into a mantra of just breathing. That actually is a way of regulating myself.

Clearly exercise, and just getting it out of your system. And getting out of your brain. So much of emotional regulation is learning to get out of your brain. So I’ve done that too.

But I will get back to the yoga for a second, I think there’s two ways that I look at life, and that’s to be in attainment mode, trying to attain something. And in an attunement mode.

And what I’ve found is that my natural tendency is very attain-oriented. And when I’m in the attain mode, I often have to atone afterwards because I have sharp elbows and I’m just going for what I want.

Tim Ferriss: Attain and attune. Or atone.

Chip Conley: Well, it’s attain, yeah, leads to atonement. Attune leads to at one. So for me, that’s being something for about a year now. I’ve been able to see myself, and so ask myself, “Am I stirred up because I’m in the attain mode?” Attain is perfectly fine. And yet, yoga is not an attain sport. Surfing, which I, at age 56, 57, I’m 58 now, I started learning to surf. This is not an attain sport. The key is to attune yourself to the wave.

And so recognizing when you’re supposed to be in the attain mode, and when you’re supposed to be in the attune mode is something that I think I’ve learned over time.

Tim Ferriss: Is your meditation practice mostly focusing on the breath and letting arise whatever arises without trying to modify it, or what does your internal practice look like when you sit for those 10 minutes?

Chip Conley: I have a lot. I’ve done TM and that’s a 20-minute practice. And that’s sort of my core —

Tim Ferriss: The mantra based?

Chip Conley: — that I go to that I do. Yeah, mantra based. Try to do it morning and afternoon. Minimum, I do it the morning.

I do a lot of other ones as well. There’s a loving-kindness meditation that I sometimes I will do, which started frankly when I’m most stirred up about someone in particular, I can sort of go that direction.

I love Vipassana, but that’s more of an extended silent meditation practice. 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 — kayaking with him and 12 of us, from island to island amongst whales with a silent kayaking meditation retreat for a week. Didn’t talk for a week. That was beautiful.

But the simplest thing to do, I think of two things: It’s 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.

Tim Ferriss: Hold on a sec! What windows?

Chip Conley: Louvered, like glass-louvered windows, so you sort of open them and they turn.

Tim Ferriss: Okay, right.

Chip Conley: Actually, the reason I like them because we have them at The Phoenix Hotel.

Tim Ferriss: I was going to say, they’re sort of like the — they make me think of really old Volkswagen —

Chip Conley: Yeah.

Tim Ferriss: — camper buses that have that type of rotational window.

Chip Conley: Exactly. So you have a rotational window —

Tim Ferriss: It’s like the vents in an air-conditioning duct in a car.

Chip Conley: Exactly. Imagine that on your forehead.

Tim Ferriss: Okay.

Chip Conley: And so what I do is I breathe through my forehead and then I breathe out my forehead. And this is how I turn down the heat on my brain. I mean, truly, this is like my, the Chip Conley approach to —

Tim Ferriss: Yeah, whatever works, works.

Chip Conley: Yeah. So that’s — but yes, the core thing I tend to do is the TM.

Tim Ferriss: The TM. For people who are interested in the second you mentioned, which is loving-kindness meditation, also known or called Metta, M-E-T-T-A. There are some fantastic guided meditations that you can listen to out there. Like Jack Kornfield has some fantastic versions of that. There’s also a really fascinating guy named Chade-Meng Tan, who wrote a book called Joy On Demand that gets into this.

Chip Conley: And Search Inside Yourself too.

Tim Ferriss: And Search Inside Yourself, which became the most popular employee class at Google at one point, I remember it had a waiting list of like six to 12 months or something like that. So let’s go back to something you mentioned. Your first book, the first book you count. How old were you when you wrote that, roughly? Do you remember?

Chip Conley: I was 38 when I wrote it and, yeah. So I had been running my company for a dozen years, Joie de Vivre and —

Tim Ferriss: How did you get Richard Branson to write the foreword?

Chip Conley: Great question. So Gavin Newsom at that point, he was the mayor of San Francisco and he was my first mentee. I mentored him, and menteed. So we went together to see him give a talk at the Virgin Records store in San Francisco.

Tim Ferriss: I remember that.

Chip Conley: Which used to exist.

Tim Ferriss: I remember that.

Chip Conley: So it was actually around the launch of that record store. It’s hard to imagine.

Tim Ferriss: Right on Market Street.

Chip Conley: Yeah. I remember, like a record store, really? Wasn’t that long ago, though. So we went there and we were there with the head of protocol for the city. Actually, this was before Gavin was mayor. He was just on the board of supervisors in San Francisco and we, I don’t know, he just took a liking to both of us. So he said, “Can we hang out?”

Tim Ferriss: How did you meet him in person?

Chip Conley: We were literally in line to actually have him sign our book. And it was me and Gavin. And so when we came up, he just ended up spending a bunch of time with us and we waited a little bit later and he talked with us, just the two of us. And we went out and had a meal.

Tim Ferriss: I’m going to keep chipping away at this, no pun intended. So you walk up. You’re good with words. Gavin’s also good with words. So you guys walk up, there’s a long line of people, what do you say or ask that gets the attention of someone or what is the presence that you put forth that gets the attention of someone like Richard Branson, who in that environment is, he’s the king?

Chip Conley: 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 —

Tim Ferriss: I knew there was something.

Chip Conley: — 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?” So that led to the conversation that led to a longer conversation.

Tim Ferriss: Amazing. Now, did you propose hanging out after the signing or did he? Did Gavin?

Chip Conley: Well, it was the next day.

Tim Ferriss: It was the next day.

Chip Conley: We just had lunch the next day. And the truth is that his company, Virgin, it was just in the early stages, I think, of thinking about doing Virgin America, the airline. And I was at that point, the largest hotelier in San Francisco in terms of the number of hotels we had. So there was some benefit to him as well.

Tim Ferriss: Yeah. How did you make the jump from him being impressed that you knew his parents names to meeting the next day?

Chip Conley: He had an assistant there and his assistant actually did know me and knew Gavin, so she was like, wise enough to know these are two — and so he said, “Can you go talk to April over there?” And so we went over and talked to April and April said, “You know what? He’s got some time to schedule it tomorrow.” And so, yeah.

Tim Ferriss: Amazing. And then flash forward and you get a foreword from Richard Branson.

Chip Conley: Ultimately he said, “I’ll write it, but you’re going to write the first draft,” and then he edited it and it went in it.

Tim Ferriss: All right. So we’re going to get, continue this, this forward and backwards chronology, if I can even call it such. Who’s Brenda Lee? And this may go somewhere, it may not go anywhere, but —

Chip Conley: Brenda Lee is this four foot, 10 inch, although she’s five foot, six with her beehive hairstyle, Nashville gal, famous country western singer. And out of the blue, 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.

Tim Ferriss: Paint a picture of the Tenderloin at this point.

Chip Conley: Well, it’s the same as it is now.

Tim Ferriss: Yeah, hasn’t changed that much.

Chip Conley: There’s a lot of drugs on the street and it’s a relatively poor neighborhood, pretty desolate, but it’s right in the middle of the city. And it’s right near Union Square and the hotel district. So we were the gateway to the Tenderloin, but we were on the opposite side of the Tenderloin from where the nicer part of the Tenderloin and Union Square was. So she’s driving through there and they’re looking for a place to stay and she wanted a motel and we were a motel. She comes in, she had no idea that our aspiration was to be a rock and roll hotel. And so she comes in and we had, weirdly enough, a guy named Arlo Guthrie staying at the hotel at the same time —

Tim Ferriss: My mom listened to Arlo Guthrie when I grew up, I know Arlo Guthrie very well. Amazing, yeah.

Chip Conley: So Arlo Guthrie’s in the hotel because The Great American Music Hall is two blocks away. Brenda Lee comes in with her bus and we have bus parking. So one of the beautiful things about The Phoenix is it had free bus parking, which a band’s going to appreciate. And she checks in and all of a sudden we’d become a rock and roll hotel. We had Arlo Guthrie and Brenda Lee and that led to Nirvana, Pearl Jam, David Bowie, Red Hot Chili Peppers, everybody you can imagine staying there over the years.

Tim Ferriss: Well now, 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 this story.

Chip Conley: No, there’s more to the story.

Tim Ferriss: Okay, so you have manifested or chanced upon this luck of having these two guests at the same time.

Chip Conley: Yeah.

Tim Ferriss: How does that then get converted into a reputation? Do they just recommend to other people? Do you seize upon that, “Hey, can we take some photos?” How does it happen?

Chip Conley: So there were some logic; my business scope brain was saying, “Okay, well, who is the person who books all of the hotel rooms for bands coming through town?” And I’d gotten to know Bill Graham, who was a music impresario, a concert promoter, and he had said, “Well, it’s usually whoever’s booking the concert, they’re doing it.” So we tried to market to them. Then we tried to market to the venues, like Slim’s or The Great American Music Hall or The Fillmore, that made sense. And then we find out, oh, there’s these travel agents who specialize in entertainment travel. So let’s go to market to them. To be honest with you, none of those worked all that well. They worked okay. The number one thing that worked, this is so funny, was the person who typically made the decision of where the band was going to stay was the tour manager.

So the tour manager was usually a guy, almost always a guy, about three to five years older than the band. His job was to make sure there was no overdoses and no groupies. And because a groupie might mean the guy doesn’t show up at the show, and of course an overdose could do that as well. And by the time he got to San Francisco, he was so stressed out because usually the tour started on the East Coast and by the time you get to San Francisco — so here’s what we did. We had one room of our 44 rooms that was a massage treatment room. Now back in the old days when it was a pay-by-the hour place, you can imagine what happened in there. But we cleaned it up and made it into a legitimate massage studio. And so we offered to tour managers, when you bring your band here, if you give us 10 room nights, five rooms times two nights, you get a free massage for yourself. And so back in the day when we started doing that, now remember this is pre-cell phones, pre-internet, pre- frankly, laptop computers.

People had satellite phones, but mainly what they were doing was going on the house phone and the tour manager is calling his friends and then sometimes writing a letter and sending it out to them in old school U.S. 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’d hopefully do. They deliver on your expectations. They deliver in your desires. But the thing they get right, is this thing at the peak of the pyramid. I wrote a book called Peak: How Great Companies Get Their Mojo From Maslow. It’s meeting the unrecognized needs of whomever your customer is. And in my case, figuring out that the customer was not all those other people. It’s actually the tour manager and what’s his unrecognized need? It’s basically to like, chill, and to relax, and they get a free massage.

Tim Ferriss: That’s incredible. Because it also acts as a contrast, in my mind, to a maxim that is often used, but I think often inaccurate, which is, granted you had this motel/hotel, but you need money to make money.

Chip Conley: Yeah.

Tim Ferriss: But if you look at what you did in that particular case, I mean you identified who your actual customer was. It was like the unspoken customer.

Chip Conley: Yeah.

Tim Ferriss: And then —

Chip Conley: No one told me, no one ever said that it was the tour manager.

Tim Ferriss: Yeah. And then the unspoken need. And the cost to offer that service is just a rounding error.

Chip Conley: 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.

Tim Ferriss: Yeah.

Chip Conley: 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 have been to, The Hotel Vitale, which is on the waterfront in San Francisco —

Tim Ferriss: I wrote a bunch of — two of my books there.

Chip Conley: Oh, thank you. Well, so long as you’re sure The Hotel Vitale — The Phoenix is in, like, the worst neighborhood in San Francisco, and The Vitale is sort of like the best neighborhood. It’s right on the Bay, on the Embarcadero, right across from the ferry building and the farmers market. So the unrecognized need for the customer, we wanted there. So The Vitale, means vitality in Latin or Italian. And we wanted to create a hotel that was sort of, what we called for the person who is post-W and pre- Four Seasons. David Brooks, we call him The Bourgeois Bohemian. So The Bobo.

Tim Ferriss: The hospitality tweeners.

Chip Conley: Yes. That hospitality tweener who sort of was looking for that. And so our point of view was, we said this is a person who reads Real Simple and Dwell. So it’s actually probably more female oriented and it’s a female business traveler. And if there are five adjectives to define those two magazines: modern, urbane, fresh, natural, and nurturing, that describes this person. And so we ended up creating on the top floor of the Hotel Vitale when we launched, 15 years ago, a yoga studio on the penthouse level that had free yoga classes every morning. Now my investors looked at me like, and they’re all guys, looked at me like, “What are you doing?” Now today, this might make sense. 20 years ago when we were concepting this, they’re saying like, “There is no financial district hotel in the world that has a yoga studio on the penthouse level; why would we ever do that?” And I said, “Well, because we’re going to be the first ones doing it.”

And so then they said, “Well, look at all of the customer satisfaction forms you’ve gotten from people in financial district hotels. And 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?”

Tim Ferriss: Yeah.

Chip Conley: 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 want. So long story short is the yoga studio had a line out the door and within a month, we were in New York Times, L.A. Times. Wall Street Journal had stories about this new sort of hotel that’s oriented toward business travelers who want to stay healthy. And The Hotel Vitale ended up becoming the most successful upscale hotel in San Francisco.

Tim Ferriss: It’s reminiscent to me of, and this could be apocryphal, I don’t know if this is a real anecdote. It’s kind of like every quote, it’s attributed to Abraham Lincoln or Oscar Wilde on the internet. But —

Chip Conley: Did you know they had a thing, the two of them?

Tim Ferriss: No!

Chip Conley: I’m kidding.

Tim Ferriss: A quote-off! Henry Ford. I think if I had asked people what they wanted, they would’ve said a faster horse.

Chip Conley: Yeah, that’s Henry Ford. I always attribute it to, we can’t ask him because —

Tim Ferriss: And to look under the hood on that decision a little bit. So the first is, and this is something that I’m constantly, maybe constantly is too strong a word, but I always consider when I’m looking at launches or books or television shows or documentaries, whatever it is, is being first. I think doing something the first time can be really undervalued. Being second, different story, right? Being first, can be very, very newsworthy in and of itself. Also, what would you have done if it hadn’t worked?

Chip Conley: We would’ve turned it into a suite.

Tim Ferriss: Right?

Chip Conley: So the key there, and 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 that in fact, after we sold the hotel, a bunch of years later, that’s what they did. But I said, “Give me that time,” because this was not going to be insurmountable if it didn’t work out. But it turned out to be, it turned it to package and position the brand of the hotel really well and be something that people valued. I think the point on that is to sort of say, “Okay, so how do you try things and do something small enough that could have a big impact, that is easily solvable if it doesn’t work?”

Tim Ferriss: Right. Which is also something that can be tied into Richard Branson, right? Because people think of Richard Branson as this throw-caution-to-the-wind maverick who risks it all despite the odds and he’s been on the podcast. But you’ve spent time with him, and if you look at, I believe it was Virgin Atlantic where he took so many in-between steps to cap the downside on something that could be unmitigated, a complete disaster, right? Airlines.

Chip Conley: Yeah, airlines.

Tim Ferriss: It’s like magazines, restaurants. You can really lose your shirt.

Chip Conley: Yeah.

Tim Ferriss: And among other things, tested with, I want to say, like a posterboard 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 the eight or 10 seats that it would take. Did that successfully, and then negotiated with, I want to say it was Boeing at the time, in order to be able to give them back the plane if it didn’t work. So behind the scenes he’s actually making very calculated bets.

Chip Conley: He’s a shrewd guy.

Tim Ferriss: Super shrewd.

Chip Conley: Yeah. And I think one of the things I learned from my dad a long time ago is build the business plan as if it’s not going to succeed. I mean, imagine it’s succeeding and you’re going to attract people for that — investors, employees — but what’s plan B, and how do you have a solution for plan B? And so that’s why I don’t build bowling alleys. You know bowling alleys, in terms of the shape of them, you can see it in the past — churches. But churches have become sort of popular for all kinds of uses, post-church era. But yeah, I think it’s really critical to sort of understand what is plan B, C, and D.

Tim Ferriss: So let’s talk about another chapter shift. And I’m going to take this opportunity to pull up a screenshot of a text exchange that I had with a mutual friend of ours, with Liz.

Chip Conley: Oh, yes.

Tim Ferriss: So could you explain it for people who don’t know who Liz is, just for a second?

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

Tim Ferriss: Why did you do that?

Chip Conley: She wasn’t here for that long, but she was here for, I don’t — I can’t remember. But weeks at a time. I did it partly because I loved Liz. She was an attorney who should never have been an attorney who’s completely amazing as a designer. So she’s one of those hoteliers who designs around hotels, which I love. Like a restaurateur where the chef is the restaurateur. So I think it’s really beautiful. And so I just loved her passion and her joie de vivre, frankly. She took such a joy in what she was doing and I wanted her to succeed. And so I’m a big believer in karmic capitalism, which means sort of what goes around comes around. And so me giving to Liz was going to pay back to me in some way over time. And frankly it’s been me doing that with a lot of different people and then having it come back reputationally. You know, your reputation is one of the few things in your life that’s portable.

And frankly it rivals FedEx before you arrive somewhere because that’s what happens with a reputation. People know you before you arrive. And I think that whether it’s Liz or a variety of other people who I have tried to help in business, it’s just helped my reputation in terms of how people see me. And instead of people standing on the sidelines sort of like jeering, they’re cheering. When The New York Times article came out this weekend, I didn’t love it. I had such a support network of people who just said, “You know what? We’re going to write letters to the editor, because it’s not a bad article, Chip, but you know what? It’s not accurate.” And they wanted to help. And I think, I once had a restaurateur, co-founded a restaurant with someone and no one really liked her. She was actually very shrewd, really tough negotiator. But when she launched a restaurant, if she got a bad review, people were sort of silently happy.

And I’m not that way. And I am not saying that to say I’m the most likable person in the world, but I will absolutely say that I do a lot of things to make that karmic capitalism work for me in the world. And as such, Liz was just an example of that. And part of the reason she hates me is because now she feels the obligation to pass it on, pay it forward to someone else, because she gets hit up all the time because she’s just an amazing hotelier.

Tim Ferriss: She’s really incredible. And she’s done —

Chip Conley: Company’s called Bunkhouse.

Tim Ferriss: Bunkhouse. And she has a number of just incredible, not just incredible properties, but incredibly different properties.

Chip Conley: Yeah, they’re soulful. At the end of one of her pools, the Saint Cecilia Pool here in Austin, it just says, in neon, “soul.” And there’s something soulful to her places. And so I want to bet on people like that.

Tim Ferriss: Yeah, there are a lot of parallels that I can see, looking at the two of you side-by-side in some ways. And it just struck me that I did a number of staycations at Hotel Vitale to work on books. Because I think I had read that Maya Angelou had done that, and I thought, “That’s a great idea.” Because at home I have all the usual distractions and ways to procrastinate. Let me treat this.

Chip Conley: Moby would do that when he’s —

Tim Ferriss: Moby?

Chip Conley: Moby would do that. He’d go to a hotel room and just shut himself off for a week and to actually figure out music.

Tim Ferriss: No kidding. So I have friends here, I won’t mention their names, but they’re well-known filmmakers because they told me this just in a private conversation, who use Hotel Saint Cecilia for their sort of staycation, creative work as well. So I’m going to jump to this text from Liz as 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 gave me quite a few, but one of them was, “He — meaning you — began building Joie de Vivre as a young man. It was the work of the first half of his life, a big sprawling family. What made him decide to sell it when he did?”

Chip Conley: Great question. One thing to aspiring entrepreneurs and people who are younger than me, just know that when you, one of the natural tendencies is we hook our sense of self-esteem and self-worth to our businesses. I remember in the early days of The Phoenix, I had one hotel before I had 52. And that one hotel, when people would come to me and say, “How are you doing, Chip?” I said, “Well, The Phoenix is doing fine!” And finally somebody called me on it. It was like I didn’t say how I’m doing. So my sense of worth and esteem had a lot to do with basically the rollercoaster of my business. Well, fortunately over time I realized that didn’t have to be the case, and it was that flatline experience I had 22 years into running my company that helped me to see that. “Is this what I want to do the rest of my life? Actually it’s not.” And I thought it was going to be, but it wasn’t.

And more than anything, I just realized that I started the company for creativity and freedom. Those were the things I said to myself on one Friday afternoon, when I said, “What did I learn this week about why I’m starting this business?” And 22 years later I said, “Do I have any creativity and freedom in this business anymore? No. I’m running a company with 3,500 people.” It was hard, though. It is very hard to sell a business that — for, ultimately when I sold it, it was 24 years — that has been your identity for most of your adult life. But it was actually harder for other people than for me. And that’s a fascinating piece of it. Is I realized my identity had moved on. I was ready for what’s next, which was to become the world’s leading expert on festivals. And I didn’t really want to be doing it anymore, but I had to deal with other people’s challenge in me changing my identity.

And there’s lots of ways people change their identity. You can get divorced, you can change your career completely, you can literally change your gender. But in my case, it was just changing the actual fact that I was the founder and CEO of what was the largest boutique hotel company, second largest in the U.S., but the largest hotel company, frankly, in the San Francisco Bay area. And for some people who liked having their friend have that role and got a lot of free hotel rooms out of it from me or restaurant reservations or massages in my spas, they didn’t like it. But at the end of the day, it was the right decision.

Tim Ferriss: So that, as you just said, sounds like a difficult decision or a maybe emotionally intense decision to work through. And I mean, I remember when this was kind of happening and you mentioned just in passing here, “I decided what I want to do next, which was 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?

Chip Conley: Yeah, no, that’s a great question. I made the decision I had — this was going to kill me if I kept doing it. And so I knew I needed to move on. I didn’t know what — and frankly then you get into the freaky, it was in the great recession, the freaky thought of like, “How am I going to sell this company in the bottom of the recession?” So I hadn’t yet found the new thing I was moving toward. I knew what I was moving away from. But moving 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.

Tim Ferriss: Yeah.

Chip Conley: Because they actually didn’t move toward something, they just moved away from something. And they’re just of sort of almost, just wasting their time.

Tim Ferriss: Yeah, they’re just in a void. They stepped into a void.

Chip Conley: They stepped into a void. And so the fact that I got to a place where ultimately I said, “You know what? I’m fascinated with festivals. I’m on the board of Burning Man and there’s no great website for all the world’s best festivals. Maybe I’ll just go around and become the world’s most interesting person and go around to festivals all over the world. And I did that, 36 festivals in 20 countries in one year. And that helped me —

Tim Ferriss: You have a great blog post on tim.blog about some of your experiences at these festivals.

Chip Conley: That’s true, I do. That’s right, exactly, yeah. So I loved, loved that process and it did help me move towards the 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 I just said, “Listen, this is my new identity.” At that point, that was my fourth book and I was like, “Okay, yeah. I write, I speak, I go to festivals, I live a good life, stop giving me shit for the fact that I’m no longer a boutique hotelier.”

Tim Ferriss: You mentioned the Emotional Equations; I remember this. And could you explain despair equals suffering minus meaning?

Chip Conley: Yeah. When I had that flatline experience and to just give — I was in St. Louis, giving a talk. I basically probably had an allergic reaction to an antibiotic for my septic leg and my broken ankle. And I went to the other side nine times over the course of 20 minutes.

Tim Ferriss: Where were you when this happened?

Chip Conley: I was in —

Tim Ferriss: Did you make it to the hospital before you flatlined?

Chip Conley: No, no. So I was giving a speech on crutches, which is what — first sign that Chip should have been staying in bed and not been on this book tour trip was like, yeah, why was I on crutches on stage giving a speech? So I didn’t, fortunately, I did not fall over at the speaker as I was standing up, at the mic. But I sat down signing books and that’s when I just slumped in my chair and then they put me, I probably didn’t have a flatline experience there. I just went unconscious for three minutes.

Fortunately, the paramedics showed up a couple minutes later. Really quickly. And they put me on a gurney, and they had to put heart monitors on me, and that’s the first time of nine times that I went flatline. And they had to get the paddles out. The first time, they didn’t have to use them. About five seconds later, my heart came again.

But over the course of the next 90 minutes, in the ambulance, in the E.R., et cetera. And I kept saying: “Okay, this is what I saw on the other side.” And whoever was there would take a note of it. And turns out it was the same thing over and over again.

But long story short was —

Tim Ferriss: Well, hold on, let’s not do long story short. We can’t do long story short on near-death experiences. What did you see on the other side?

Chip Conley: There is, by the way, a festival of — a pilgrimage of — the near-death experience in Spain. Spain has the weirdest festivals in the world.

What I saw was this. And the fact that it happened over and over again, means it’s pretty remarkable and worthy to just talk about it.

So I don’t love the mountains. I love the beach. Mountains are okay. I do like it. I love being in nature. So it’s interesting this is a mountain setting. So it’s a mountain setting, a chalet with a huge sunroof, skylight, and light is pouring in the skylight, beautiful light. And it’s pouring in in such a way that there’s actually this viscous oil, a very heavy oil on the ground, on the most beautiful, wood-grained floor you’ve ever seen.

And because of the way the light’s coming in, and it’s hitting the floor, this oil that’s sort of slightly moving, or it’s going down these stairs, these beautiful wood stairs, It’s casting this beautiful kaleidoscope of colors on the wall.

And so what I see is light. I see colors, and I see this weird, frangipani-scented oil going down these stairs. And that’s what I kept seeing. And I never saw anybody else, didn’t see anybody on the other side. What I saw myself as observing, almost floating above this. I felt incredibly peaceful, and everything was moving very, very, very slow-motion.

And I kept coming back to that. And I’ve never actually sat down with a dream analysis or anyone, to sort of say, “What does it mean?” The fact it’s stairs, going downstairs, means I’m maybe going to Hell. But actually, it was up in a mountain chalet, way up toward Heaven. 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.

So. Yeah. I was in the —

Tim Ferriss: What did you make of that?

And I’m not saying — there is no — if you had a Freudian dream analyst here, and they said, “You know what that means? Let me tell you.” I’d be like, “Bullshit. Come on. You can give us your opinion, but…” What did you…

Chip Conley: What do I take from it?

Tim Ferriss: Yeah. Just subjectively, yeah.

Chip Conley: I take from it how I want to honor and experience beauty in my whole life. The gods of efficiency, which tends to be my religion, these gods of efficiency have a tendency to force me, or have its way with me, in terms of just getting very clipped in how I do things. Because I have to get all these things done.

And being clipped and doing things, doesn’t allow for the time to sort of have the immediacy of seeing, in that moment, that beautiful thing.

So I think what it’s helped me to see is: How do I create beautiful moments in my life, and how do I take time to do fasting, three or four days fasting in a row, and things like that that allow me to just be in the moment? That’s one thing.

Number two is the calmness I felt. So no fear of: “Okay, I’m dying, and it’s just going to be terrible.” There was that. But I think the thing that was most interesting was just the fact that the oil was moving so slowly. It’s like there’s a ketchup commercial, anticipation, a long time ago. Maybe Heinz 57 ketchup. And 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. So that’s what I take from it, which is a positive overall perspective.

That night, after having all those experiences, I’m by myself in a room at the hospital in St. Louis, and weirdly enough, in my backpack, that I’d brought with me on this trip, was Man’s Search For Meaning, Viktor Frankl’s book. And the reason it was there is because I’d gone through a few reality rough months, and one of my closest friends, who was my insurance agent, whose name is Chip, had committed suicide four months earlier.

And so I was trying to make sense of my life. And here I had this book. And as I’m reading this book — I had a hard time sleeping that night — I’m reading this book, and I was just distilling if I were to take the meaning of that book, Man’s Search For Meaning, and turn it into an equation, it would be despair equals suffering minus meaning.

And the way I thought of it is: Suffering is sort of a constant, if you’re a Buddhist, and I slightly am. You believe that suffering is always ever-present. It’s the first Noble Truth of Buddhism. And yet suffering and meaning are sort of inversely proportional to each other. So if you do the math of like: “Okay, despair equals suffering minus meaning. Eight equals 10 minus two.” If you take two, and turn it to four, then eight becomes six.

And so despair goes down when meaning goes up. And this is when I realized that that practice I’ve had since being a 23-year-old, of writing what my lessons were for the week, was a practice that actually was giving me meaning. And that equation, which I came up with that night, I ended up teaching it to all of our leaders in the company, as we went into the Great Recession.

And, ultimately, I said, “Darn it.” I went to Bhutan to study the gross national happiness index because I wanted to see what was the happiness equation in life. And I ended up giving a TED talk about that. And then I ended up deciding to write this book, which was a series of 18 equations that sort of help you make sense of your emotions, whether it’s happiness, or disappointment, or wisdom.

Tim Ferriss: Are there any other equations that you find yourself referring to, or thinking of, more often [crosstalk]?

Chip Conley: Yeah, I’d say a couple. The anxiety one’s very relevant in the business world, and that’s anxiety equals uncertainty times powerlessness. So it’s not a plus, it’s a times. So the uncertainty and the powerlessness together are combustible.

So what I help people to see, if they’re in that space, is: What is it that you can try to find some certainty about, and what ways can you actually create some influence, and some sense of power?

And by doing that, you actually help people get to a place where they have a little bit less anxiety.

Tim Ferriss: Makes it very tangible, right. I mean —

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

And those both, though, are negative. The happiness one, that I learned in Bhutan, was happiness equals wanting what you have, divided by having what you want. Wanting what you have speaks to gratitude. Having what you want is the process of gratification.

So it’s not to say — it says gratitude is better than gratification. Well, that’s fine if you’re a Buddhist, that’s fine if you don’t want to go out and attain, attain, attain. I want to go attain, and I want to go gratify, but gratification doesn’t necessarily bring happiness. It may bring success. And for a lot of people who think that success will bring happiness, they go on the hedonic treadmill and end up realizing, just when they get the thing that they thought they wanted, there’s some new shiny object that becomes the new thing.

Tim Ferriss: The rabbit leading the greyhound around the track just sped up a little bit.

Chip Conley: We know that one. Tim. Okay. We occasionally go there.

Tim Ferriss: Well, you know, it’s you, me, Liz, and a few million people who might be listening to this.

And speaking of Liz. So this ties in very, very nicely. Both you and Liz are very thoughtful. And make a point of trying to be aware of your own thought processes, reasons for doing things, the drivers behind the superficial answers that we’re all inclined to give, that are fast and easy and expedient.

So one of her questions was: “I notice that Chip has made a few life changes. Selling Joie de Vivre, Airbnb, now doing what you’re doing. For what looks like 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 (like me, I suspect), just can’t help themselves. How do we learn to just be still? Should we? Is that the goal?”

Chip Conley: Wow.

Tim Ferriss: How do you begin to think about that?

Chip Conley: I want to wring her fuckin’ neck. No, I’m kidding!

Tim Ferriss: But this is, I think —

Chip Conley: No!

Tim Ferriss: — something that a lot of people —

Chip Conley: No.

Tim Ferriss: — who have become good at —

Chip Conley: Absolutely.

Tim Ferriss: — achieving struggle with.

Chip Conley: Oh, totally.

You know, Peter Guber, I got to interview him onstage, he’s one of the — actually, you know Peter Guber!

Tim Ferriss: He’s a fascinating guy.

Chip Conley: We actually have both been in his box at the Warriors games.

I interviewed him onstage, and this guy’s 20 years older than me, and he’s been successful in so many different ways.

And I was interviewing onstage at the Airbnb Open, which is our big host open that I was in charge of. We had 20,000 people in L.A. at this one.

And so I’m onstage 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 —

Tim Ferriss: He’s very driven.

Chip Conley: — to succeed at the next thing.

So what I took from that, and what I take from Liz’s question, is: I think the real question here is not whether you’re going to just be still. I love being still. The fact that I’m a meditator, the fact that I have chosen to live in Baja, California an hour north of Cabo San Lucas, on the beach, learning how to surf, and having a very simple life there, means there’s been a lot of conscious choice of how I’m curating my life. Not living in San Francisco any more.

And, yeah, I have these ideas that I feel like I want to go out and try in the world. But the question is: How am I executing on them, and what is my intent — or what’s the sort of silent intent — for why I’m doing it?

And I think for so many of the things I’ve done in the past, certainly Joie de Vivre, was at times an exercise in seeing how big Chip’s ego could get.

Now I say that not to beat myself up, but I do say that from the perspective of: I was this guy who was getting a lot of my sense of self-worth from the fact that this hotel company was successful. And so my ego was on display.

And then I joined Airbnb, because the founders asked me to, and all of a sudden, I’m not — you know, I was the tiny version of Richard Branson in my company, but now instead of being the sage on the stage, I’m on the guide on the side. And I’m helping these three co-founders take their little tech company, and turn it into a global hospitality brand.

And I realized in that process that I’m still driven, I’m still totally in it, although I actually was learning how to not do the 70-hour-a-week kinda thing. Not four-hours-a-week, or whatever. You’ve been able to —

Tim Ferriss: Whatever. Whatever that book was.

Chip Conley: What I was realizing was that, actually, I’m not doing this for ego purposes. I actually feel like I’m doing this more for legacy purposes. I’m doing this to actually help them, and I believe in their mission. The Airbnb mission to belong anywhere, help people belong anywhere, and turn strangers into friends.

All of that was good. And now this Modern Elder Academy that I’m doing in Baja that she’s reciting there, you know, the reality is yeah, it is me being driven again, but I’ve put guard posts on it. I’m doing it in Baja. I’m doing one location, I’m not doing multiple locations. And —

Tim Ferriss: So you feel comfortable with that commitment?

Chip Conley: Yeah, no, I am. Actually, and frankly, the cancer — you know, for those who didn’t hear earlier on the thing, I’ve got cancer. The cancer sort of was another educator of saying: “Yeah, I think midlife wisdom schools are a thing for the future, in a huge way.”

I think the idea of lifelong learning, and how do we go to a retreat that helps us to repurpose ourselves, reframe our mindset, to have a growth mindset about our aspirational aging ahead of us? I think all that’s important. No one’s done that yet. There’s been all kinds of retreat centers, but not a place as a curriculum for people in midlife.

Tim Ferriss: When you say midlife, let’s put an age range on that.

Chip Conley: Well, midlife —

Tim Ferriss: Or it doesn’t have to be age, but how does someone know if they’re in midlife, as —

Chip Conley: They’re in crisis.

Tim Ferriss: — as it applies!

Chip Conley: Yeah, no, midlife has historically been defined as either 40-60, or 45-65.

The truth is that the phrase “midlife crisis” was coined in 1965, and the reason it didn’t exist before then was because longevity in the U.S. was 47 years old in the year 1900, and it became 77 by the year 2000. We added 30 years of longevity in one century.

So what happened is this new era of life sort of emerged.

Tim Ferriss: Right, it’s not yet fade to black. It’s like: “No, you have another half the movie to go!”

Chip Conley: Well, you do, and the thing that happens in midlife, and how you know you’re in midlife — whatever the age — 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. Invisible name tags that define who you are in the world. And you actually, frankly, are sort of feeling overwhelmed by all of that accumulation.

There’s this reset that happens in midlife. And you could say, frankly, with the Millennial generation, it might happen, actually, earlier in life. It might happen at 35. Frankly, in Silicon Valley, it absolutely happens in the mid-30s. Especially if you’re an engineer, where you feel like: “Wow, I am no longer perceived as an up and comer.” And in an industry that is like the entertainment industry, or fashion.

Tim Ferriss: Yeah, or professional sports.

Chip Conley: Yeah, exactly. So I think, personally, midlife is from 35 to 75. And it used to be just 45 to 65. It’s happening younger, because of the fact that people feel irrelevant earlier. The digital intelligence that we desire in companies means that there’s a greater and greater desire to hire the new digital natives. And I think it’s going to last longer, midlife, because if we’re going to live to a hundred, which is sort of the future, as a longevity, we’re right around 80 right now. But by the time we get to the end of the century, I think we’ll be about at a hundred for longevity in the U.S.

That means, at age 75, you’re probably still working. At least by choice, or by necessity.

Tim Ferriss: You’re creating. I mean, doing something.

Chip Conley: So midlife used to be a crisis. Now it’s a marathon. And that’s ultimately what led me to saying: “You know what? We need to figure out this wisdom school. How do people go into midlife, and not think of life as being just a one-tank journey?”

You fuel up with all of your education and support, up to age 20 or 25, and then you drive this vehicle that we call our bodies for the rest of our life, and at midlife, you’re starting to run on fumes, and you need a pit stop.

And so the Modern Elder Academy is the idea of that pit stop, and I think it’s going to help to create a new category of academia, or even hospitality real estate, which is: the midlife wisdom school.

Just like Canyon Ranch 40 years ago. Mel Zuckerman, overweight accountant from L.A., wanted to go a place to get healthy, and all the places that he saw 40 years ago were mostly fat farms and mostly for women. And he ended up creating Canyon Ranch in Tucson, and it basically created a new hospitality real estate category, called the destination spa resort. Spas had existed for thousands of years, but not a category of real estate called destination spa resort.

So I think that’s what I’m trying to do. So to answer, in a long-winded way, Liz’s question: when I see something like that, and I can see that I can be a social entrepreneur that’s actually trying to fix a societal ill, which is ageism and people getting stuck in midlife, I’m going to do that. And in this case, I’m doing it as a social entrepreneur, with a social enterprise, where 60 percent of the people are on scholarship, so I’m funding a million dollars a year in scholarships. That is something I want to bet on, but I want to bet on it as a catalyst for others to do their thing. Just —

Tim Ferriss: That’s what was I going to ask. Is —

Chip Conley: So Burning Man created a great idea, and so there’s a bunch of 10 Principles festivals around the world. Esalen, great idea 1962, led to a hundred personal growth retreat centers.

Tim Ferriss: Got it. So the academy is a proof of concept.

Chip Conley: It’s proof of concept, and a catalyst for other social entrepreneurs around the world to say: “Let’s create one in the Sacred Valley of Peru, or in Kyoto, Japan, or in the Catskills of New York.”

Tim Ferriss: Do you think, when you say — ’cause I can see a bunch of workarounds to the one-location limitation. So when you say “one location,” does that mean that you will be only hands-on in one location, or do you envision some type of, for lack of a better descriptor, a franchise model, or an association, or a loosely organized affiliate collection of dozens or hundreds of properties that Chip is somehow involved with?

Chip Conley: I love your enterprising mind, and I have thought of all of those!

Tim Ferriss: Well, yeah. Well, I just want to know, when you say —

Chip Conley: No, I —

Tim Ferriss: “I’m limiting it to one location,” is there a footnote to that?

Chip Conley: Thank God for cancer.

Tim Ferriss: Yeah.

Chip Conley: Honestly. The path that you’re talking about, I was in contract negotiations on a second location, and in discussions on a third location. When I found out about my cancer, on the second day of the book tour, right before the TED talk, and six weeks before the Modern Elder Academy was opening to the public after a six-month beta period, so at that moment, I said, “No.” And I keep saying no.

The thing I will do is create sort of the startup kit. “Here’s how you can create one.” Not a Modern Elder Academy — we may only have one location in the world — but a midlife wisdom school. You call it what you want it to be, here’s how we can do it. It could be a consulting opportunity, but I don’t really care about the money on it. I’m lucky enough. Thank God for the Airbnb, last six years of being there, because I don’t have to worry about money, that’s for sure.

I just like the idea that a legacy I can look to in my life is to create a way for people to aspire to aging. Aging is not something that we aspire to, and yet there are a lot of real unexpected pleasures of aging.

The U-curve of happiness is — do you know that? Do you know it?

Tim Ferriss: No.

Chip Conley: Oh God, let’s talk about this.

The U-curve of happiness is so fascinating. It’s so at odds with the societal narrative.

Tim Ferriss: I think I can see where this is going.

Chip Conley: So the U-curve of happiness has been proven in every country but Russia. Russia, people get happiest after they die. It’s a statistical error, clearly, but there’s something to that.

Every other country in the world that has been studied, what they show is the following: From about age 25 to about age 45, between 45 and 50 depending on the country, is a slow decline in happiness. Because of that accumulation, because of that collection of things that we start to do that prepare us for midlife.

And then, between 45 and 50, there’s this — what Brené Brown would call the unraveling. Another Texan. She’s in Houston.

Tim Ferriss: Yeah, oh yeah. She might even be here —

Chip Conley: She might be here.

Tim Ferriss: — in Austin now —

Chip Conley: She is, that’s right, she’s —

Tim Ferriss: — because her daughter’s here.

Chip Conley: Yeah, exactly.

So the great unraveling that happens in midlife, where people actually start to discard things, and they move from the accumulating mode to the editing mode.

So that editing mode, the idea that people are moving into that mode, leads people to get to a place where they get happier with each successive decade. So people are happier in their 50s than their 40s. They’re actually happier in their 60s than their 50s. And they’re happier in their 70s than their 60s.

Men start to flatten out in their happiness, in the second half of their 70s. Women, it starts happening in their early 80s.

So in essence, what it’s saying, because women live longer than men, is there a point at which, five to 10 years before you die, you actually start to maybe get a little bit less happy. Because there can be acute health issues going on.

But that’s fascinating. The fact that we actually get happier as we get older, that is not what you see on the TV.

Tim Ferriss: Yeah, no.

Chip Conley: 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 is not as quick as it used to be. But a thing a lot of people don’t know about the aging brain is it gets more adept at doing left-brain/right-brain tango. Which means, basically, the brain shrinks a little bit as it ages. You’re able to, as you get older, move from the linear left-brain, to the creative right-brain much more easily, more adeptly.

And what does that lead to, in terms of a positive? It leads to being able to think more synthetically, holistically, get the gist of something.

So if you want somebody on your team to actually sort of hear it all and then distill it down to the wisdom of what they just heard, an older person can do that better than a younger person. A younger person’s much better at doing focused.

So why is that relevant? Well, let’s talk about Airbnb for a moment. At Airbnb, when I joined six years ago — I love the founders, and they were doing an amazing job, and the company would’ve been successful without me — but when I joined six years ago, and it was maybe 1/20th of the company’s size today, we had 30 strategic initiatives in the year 2013 when I started, and nobody in the company, including the founders, could actually recite all of them.

So later that year, we did an offsite retreat in New York, and I said to the leadership team, of which I was now a part, I was Brian’s mentor, but I was also reporting to him as the head of global hospitality and strategy.

I said, “We gotta get down to four. So for 2014, we are only going to have four strategic initiatives.” And so we spent three days arm-wrestling over that one. 23 different potential initiatives that we were going to do.

And it was that kind of distilling down. I think the —

Tim Ferriss: How did you do that? Because I think a lot of people listening, maybe even one person sitting here talking, i.e. myself, struggle with long lists of prospective or current projects, right?

Chip Conley: Yeah, for sure.

Tim Ferriss: So here you have a fast-growing — very, very fast. I mean, understatement. Growing startup. And they have a list of — how many? 20-something? Who knows?

Chip Conley: Yeah, 23 initiatives that the 12 members of the leadership team thought should be our potential four for next year.

Tim Ferriss: So how do you facilitate a process by which you get that down to four?

Chip Conley: Well, it’s the intellectual joust of —

Tim Ferriss: Because you’re also kinda the new guy on the job, right?

Chip Conley: 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. I was 21 to 23 years older than all three founders.

But I think what they appreciated was there was an element of — I think a modern elder versus a traditional elder — the difference is the modern elder is as curious as they are wise. And it’s that curiosity that opens up possibility, and the wisdom is what distills down the essence of what’s important. And it’s that essence of what’s important that, I think, we got to in those three days in New York, where we sort of said: “Okay, so what is it that we want to be when we grow up? We want to be a place where people can belong anywhere.” We had not said that out to the public yet, but that was the direction we were going in terms of our internal mantra of the two words that defined us.

We also looked at: Could we take the idea of the Airbnb sharing economy to office space, or conference facilities, or anything that had excess supply? There are a lot of natural sharing economy businesses that could be created, but we also had to ask ourself: “What’s the dream of what we want this to look like five years from now, or maybe even 10 years from now?” Because Brian really wanted us to look very far into the future. And maybe that dream could help become an editing function.

So for me, that reminded me of something I did back in the Joie de Vivre era when I was running my boutique hotel company. When we were trying to figure out what’s our differentiator versus Marriott or even Kimpton, another boutique hotel company, we actually imagined the idea that we could ask the question: “What business are we in?” because the number one Harvard Business Review reprint of all time came from an article from 1960 called Marketing Myopia by Theodore Levitt. And then management theorist and author Peter Drucker took that idea one step further. He said the most important question any business leader could ever ask themself is “What business are we in?”

Well, back in my Joie de Vivre era, we took that idea of what business are we in, and we turned it into a little bit of a game. The idea was we would be asking executives or senior leaders to ask themselves that question in the following manner. So one person would sit facing the other. The person asking the question would say, “What business are we in?” And the second person, the person answering, would say, “Okay, we’re in the boutique hotel business.” The first person would say, “Thank you. What business are we in?” And this time, the second person, the person answering, could not answer the same way twice, and if you do that five times, it really almost is like an archaeological dig to figure out the essence of your company. What’s your soulful differentiator as an organization?

This is how we found out that we were in the identity refreshment business at Joie de Vivre. And it was this same idea that we applied to Airbnb. When it came to an offsite retreat, we did relatively soon after I joined the company, we sat our executives in pods of two so they couldn’t hear each other. Any company could do this. And we had them go through this exercise of asking the question five times, “What business are you in?” You can’t answer the same way twice. And the beauty of this is it ultimately got us to a place over the course of that day where we came to the conclusion that belonging anywhere was really the mantra, the definition of what differentiated us versus the Marriotts of the world. And it was that idea of belonging anywhere that helped us to then imagine how we could edit all the possibilities of the things we could go into.

Similarly, any executive or any person could actually ask this question in a slightly different way for themselves. The question would be: “What mastery do you offer?” or “What mastery can you offer?” So have a friend of yours ask that question of you five times, and you’ll be sort of surprised at, by the fifth time you get asked that question, and you’ve had to come up with four other answers before that, what kind of revelation you may have in this archaeological dig that helps you to mine your own personal mastery.

Tim Ferriss: And to go back to the Academy, whether that’s a book on the reading list or an exercise or a practice that attendees have found particularly valuable, is there anything that comes to mind that people at home might try or think on?

Chip Conley: Well I think the basic premise of the Academy is that in midlife, you need to sort of reframe your mindset for what’s moving forward. There’s a famous Carl Jung quote about [how] you can’t live the afternoon of your life the same way you did the morning. Speaking to that, we have an exercise around evolution — evolving — because the first lesson in my book Wisdom @ Work: The Making of a Modern Elder is to evolve, and it’s the hardest one.

Tim Ferriss: Evolve is the first step.

Chip Conley: Evolve is the first step, the second step is to learn, the third is to collaborate, and the fourth is to counsel. We can come back to that if you want in a moment. But evolve. Wow, what does that mean? It really means learning to edit what is no longer serving you. We do a lot of different exercises around the idea of liminality, which is being in between two things.

Tim Ferriss: For people who might recognize liminal, subliminal.

Chip Conley: Yes, exactly.

Tim Ferriss: Subliminal messages.

Chip Conley: Liminal is sort of right there and it’s sort of in between two things, it’s the transition that frankly, a caterpillar to a butterfly, the cocoon is the liminal state. People don’t like to be in a liminal state. When you’re a kid, you’re used to it because everything’s in between.

Tim Ferriss: Everything’s in between.

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

Now if you were to do this on your own, no one’s going to write those for you. You have to write these yourself. But the process of what you can do is you actually write down anything from, you know, “My body is falling apart,” or “I’m never going to meet the love of my life.”

Tim Ferriss: So they’re in part beliefs that are no longer serving you?

Chip Conley: That’s right. “Millennials rule the world.” Yeah, there’s a variety of different things we have there. Then people a lot of times use their own name tags. What we do is the crescendo of this experience that afternoon is people slap up to six different name tags on their chest. We go around with them —

Tim Ferriss: The name tags that are already filled out?

Chip Conley: As well as the ones they filled out themselves.

Tim Ferriss: I see, and if they have one that they can’t find, then they fill out the empty tag.

Chip Conley: That’s right, exactly. So then you go around the room — and you can do this with like four friends — and you go around the room and look at each other’s name tags, and then you ultimately have a conversation, one on one or in a small group, about why these aren’t serving you anymore and how you’re going to be willing to get liminal and try transitioning into something new.

As a result of that, we end the afternoon with a little fire pit. We don’t walk on any coals or anything like that. We just have people write down what’s the thing that they’re ready to evolve out of that’s no longer serving them. It could be — so many examples of things are like, “You know what, my sense of my success in my career will no longer be my sense of success in life.” That’s an example of something saying, “Okay, I’m going to put that in the fire and let it burn.”

That’s an example of a specific kind of exercise we do. We do a lot of mindfulness exercises as well in terms of helping people to calm their nervous system.

Tim Ferriss: Can I pause for one second?

Chip Conley: Yeah.

Tim Ferriss: So the up to six tags on the chest. Do you participate in this exercise?

Chip Conley: I do.

Tim Ferriss: Would you be willing to share some that you’re burned?

Chip Conley: Well, one of the ones —

Tim Ferriss: Or written.

Chip Conley: But yeah, I mean since you’ve heard my health diagnosis, I said like, “I’ve recently been given a scary health diagnosis and I feel a little lost.” So that would be an example of a name tag. Another name tag would be, “I think I might never meet the soulmate that I met six years ago and no longer in that relationship; I am in a relationship but it’s turned into a different kind of relationship.” Another one could be — another one that I’ve written and then ultimately burned is, “It’s time to take down the scaffolding of my ego.” What does that mean? It means like, over the course of my teen years and growing up, you build an ego. We sort of create this container. 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.

What I mean by taking down the scaffolding of the ego is really sort of saying, “Behind that is something that’s really amazing. It’s the soul, it’s the heart, and I’m no longer going to let my ego be the thing that I lead with.” Then I come up with a list of things how that showed — what are the practices or ways of being that actually have to change in order for that to be the case?

So those are some examples just off the cuff. I wish I had a list.

Tim Ferriss: Do you have people prepare for the time at Modern Elder Academy in any way, or do they show up and that’s sort of time zero when things begin?

Chip Conley: Well, they’ve got to read the book, Wisdom @ Work: The Making of a Modern Elder, and they do two exercises. One, which is an identity cleanse, where they actually talk to their friends about what parts of their identity work and what parts of identity don’t work so well, so they actually get some feedback. This is before they arrive. Then they do a values inventory, like what are their 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.” So they ask themselves then how can they — we ask them and we work with them — because after people leave, that group of 12 to 18 people in the cohort, they literally, for some of the groups, have a weekly Zoom call every single week. They’re sort of accountability partners and people who can sort of help them say, “Okay, yeah, you said your number one value was this and now it looks like it’s not there anymore. What’s going on?” That’s part of what happens too.

Tim Ferriss: What would be example values that people might then put in order?

Chip Conley: Some of the most obvious ones are family, religious beliefs, making a difference in the local community, or trying to change the perspective on climate change. Those are some of them. There’s other ones, which is like ways of being, which are feeling free. Some people say that’s not a value, but that’s sort of a way of being.

Tim Ferriss: Yeah, could be a way of being, priority.

Chip Conley: Yeah. That’s what they are, so it’s a mixture of I would say values and ways of being. We have like a list of 60 of them and they come up with their top five and then stack rank those top five. Then over the course of the week we don’t force them to go back to it, but there’s exercises we do that allow them to, on their own, sort of look and see how those have changed.

Tim Ferriss: Would you be open to talking about family for a few minutes?

Chip Conley: Yeah.

Tim Ferriss: Okay.

Chip Conley: Let’s do it.

Tim Ferriss: Because I would love to hear your — some backstory that I don’t know and then have some questions about current day.

Chip Conley: Yes.

Tim Ferriss: You are openly gay.

Chip Conley: Yes.

Tim Ferriss: Have you been openly gay kind of from the get go, or when did that become something that was publicly — that you felt comfortable publicly disclosing?

Chip Conley: I was 22 when I came out — and dated women, girls, you know, I was very active sexually in my high school. But I knew behind the scenes, like there was something there. I grew up with a father who I love — both my parents are still living, they’re 81 — but my dad was Steven Sr., I was Steven Jr., the chip off the old block. My dad was a captain in the Marine Reserve, hardcore dude, and I was the oldest and the only boy. So I was meant to be like the mini-version of Dad.

So my process of being an Eagle Scout like my dad, All-American water polo player in high school, and then playing water polo at Stanford, student body president, all this stuff was like, I was on the path to be just — actually, my dad and I, we talked about this recently, he said, “Chip, all I wanted you to do is be a better version of me.” That was so interesting to hear that. I always knew that was the case, but I never heard him, and so at 81 years say it, I was like, “Dad, I know,” and that like, fucked with my mind.

I did everything I could to sort of just be this better version of Dad and then I was in the fraternity at Stanford and that’s where it started messing with my mind, being in a fraternity with a bunch of guys who I had some attraction to, but I wasn’t doing anything about it and I was dating a couple different women, and it was in between my first and second year of business school, I was 22 years old, living in New York, working for Morgan Stanley, investment banker by day and at night walking into my first gay bar. That’s when it was like Wizard of Oz Munchkin Land. It went from black and white to technicolor. I was like, oh wow, well, this feels a little more —

Tim Ferriss: This may be a thing.

Chip Conley: Yeah, this may be a thing. But back then, wow, I mean I came out the summer that Newsweek had the cover story about the gay cancer they called AIDS, and so it was a really, really not an easy time to come out. Certainly not an easy time to come out in terms of the world that we live in today compared to then in terms of, especially someone who’s a hardcore business guy. So when I started my company at 26, people knew I was gay and it was sort of an unusual thing to have a founder CEO. I was living in San Francisco and it was a boutique hotel company, so that made it a little easier. So ever since age 22, pretty much just been an outwardly gay man, and have had two long relationships, and now have a couple of sons with a lesbian couple.

Tim Ferriss: So I wanted to ask you about that next. So how did that come about?

Chip Conley: So the women live in Houston. Laura’s been a long time friend of mine and she asked me, her timing was perfect. She asked me three weeks before I was selling my company, Joie de Vivre, and I was like the mama and the papa of Joie de Vivre. So I didn’t have a co founder. Ran it for 24 years. Knew almost everybody in the company, 3,500 employees. I had a lot of parent energy that had gone into my company and I was wondering, “What’s going to happen when I step away from that?” And three weeks before I made it public that I was actually selling, she approached me and I had been approached before by lesbians that wanted my sperm, but I’d always said no.

So this time I said yes. So the idea was frankly, they’re going to be in Houston, I’ll be the sperm donor. I don’t have any legal rights or financial obligations, and we’ll see how it goes in terms of whether the boys — or the kids, boys or girls — will know who their dad is. So it was that sort of like, okay, I mean it was pretty transactional, although probably a little bit more like, okay, maybe it will be more than that, but let’s see as we go.

Well, the two women ended up having two boys and more than anything, I think the women, they live in the state of Texas, and so the rules around this were tough. Texas is a little bit more of a conservative state and so there was some worry that okay, well I’m the real biological dad, and so can the non-biological mom be a mom? Long story short is we got to a place where it is beautiful. They knew that my intentions were not to be the full-time dad or to even be in a co-parenting role. I was there to be the boys’ dad when I’m there, and I’m there a moderate amount, and they come down to Baja a lot. It’s been beautiful. It’s been a great way to give these boys a lot of love and, in essence, three parents instead of two.

Tim Ferriss: Number of different follow-up questions. So the first is reflecting on something you said, which is: “I’d been asked before and I said no.” So I had been asked a few years ago by a very close friend of mine if I would be a sperm donor for his sister who had just gotten out of a very long relationship, who had been kind of strung along by a guy until she was in her late 30s and I thought very, very seriously about it, and I’d never considered it before. Thought very seriously, was going to do it and then had a friend of mine who had at that time one young child, now has two, and he said, “Tim, if you do that, you are going to need and want to be involved in some fashion. I know you well enough; it’s not going to sit well with you. You’re not going to be able to go hands-free.” So I decided not to do it. Why did you change your mind? Like why did you say yes in this case and no in previous cases?

Chip Conley: Well, I think this idea that literally, I psychologically analyzed myself and I thought, “I really have had all the parent energy being the mentor and almost father figure for so many people in the company,” and that was going to change. I didn’t necessarily understand what kind of gap that would create in my life. So the timing was perfect. So I understand your point of view and yet I was in a place where there was a part of me that was thirsty for it. And because the women were so self-sufficient about how they wanted to do this, I figured, “Okay, let’s see,” and I didn’t know whether it was going to turn out as it’s turned out, which is much more integrated in the boys’ life.

Tim Ferriss: How did that come to be?

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

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

But I do think that this idea of having younger people who need your tutelage and love helps us get out of our ego. There’s no doubt it’s a zen practice to actually be with a little child, and they take all of your attention. But I think the process of how we define and create family has certainly evolved a lot in the last three or four decades.

Tim Ferriss: How are you thinking about parenting in the sense that are you going instinctive, have you read books on the subject?

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

There’s a beautiful Dan Gilbert TED Talk about the fact that we all underestimate how much change is ahead of us, frankly, at every different era of our life. So I think the idea of embracing liminality and sort of saying, “Yes, I’m moving to Austin.” “Yes” — a couple of years ago — “I’m moving to Baja” and so when you embrace it and you sort of see it as just the nature of life, it allows for it to, it allows for you to see some of the secret beauty in some of the things you might be resisting.

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

But I don’t know, more than anything I’m just curious. Peter Drucker taught me that curiosity is the elixir of life. I really believe that and I think that the thing that makes a modern elder different than a traditional elder is the traditional elder was about being revered, it was about reverence. You revered your elder. You respected your elder. It’s not about reverence anymore, it’s about relevance. Relevance requires understanding the modern day world.

Not just spouting wisdom that sometimes is timeless and age old, but it’s actually knowing how to fit that age old wisdom into the context of modern day problems. 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.

Tim Ferriss: Curious and wise and maybe also unrushed so you can watch that oil in slow motion.

Chip Conley: Yeah, watch that oil.

Tim Ferriss: Going down the stairs.

Chip Conley: Yeah, yeah. Or watch the whales. You know, nature is such a teacher. I’ve got to say, being here in Austin there’s some really beautiful nature, natural parts of Austin and I think anybody who doesn’t get romanced by nature on a regular basis is missing that lyrical sense of what life is meant to be.

Tim Ferriss: Yeah, definitely. I have just a few rapid fire questions. They don’t require rapid fire answers, but I always like to ask at least a handful of these. So the first one, outside of your own books, what book or books have you gifted the most to other people and why?

Chip Conley: Well, other than Man’s Search For Meaning, which is probably my number one gift, recently, the last couple years there’s a book called The 100-Year Life. The 100-Year Life, written by a couple Brits, and it sort of says, “Imagine the future where the average person lives to 100. How is that going to change on a personal and societal basis?” It’s a really interesting, observational book.

The Happiness Curve, which we talked about earlier. The U-curve of happiness is what we call it. The name of the book is by Jonathan Rauch, it’s called The Happiness Curve. That’s become a favorite to gift. I also love Danny Meyer the restaurateur. He’s got one of the best books on hospitality ever written, which is called Setting the Table.

Tim Ferriss: Yeah, so Danny Meyer. What’s the list? I might be getting, we certainly have Shake Shack for that.

Chip Conley: Union Square Hospitality Company.

Tim Ferriss: Union Square Hospitality.

Chip Conley: He’s got everything from Gramercy.

Tim Ferriss: Gramercy, that’s what I was looking for. A friend of mine used to work on the line there actually. Gramercy Park. Fascinating, fascinating guy.

Chip Conley: Yeah.

Tim Ferriss: Also, some good philosophical food to chew on, right?

Chip Conley: In terms of his —

Tim Ferriss: Practical and philosophical in terms of let’s say eliminating —

Chip Conley: Well, speaking of philosophical, thank you. Marcus Aurelius Meditations, I have given that away to a number of people. Here we go. There’s a Seneca book about the short life.

Tim Ferriss: Yeah, On the Shortness of Life.

Chip Conley: On the Shortness of Life. One of the things he says in that book is he says something about the fact that it’s not so much the shortness of life, it’s how we waste it. I think there’s something to that in terms of what percentage of your life is being spent wasted? Also, a longevity thing that I’ve been thinking about lately is imagine what age you’re going to live to and the online longevity sites say I’m going to live till I’m 98, then ask yourself how much of your adult life, if you start counting at age 18, is still ahead of you?

In fact for me, at age 58, I’m at halftime if I live to 98. When you start realizing you’re only 50 percent of your way through your adult life, you take up surfing at 56 or 57. You take up Spanish, which I’m doing now because I live in Mexico part of the time. Better learn Spanish. Mi espanol es muy malo! So, yeah.

Tim Ferriss: Where you write two-thirds of the books that you are going to write in your life as Peter Drucker after 65. If you could put a word, a message, a quote, a question, anything non-commercial on a billboard metaphorically speaking, to get it in front of billions of people, is there anything that comes to mind that you might put on that billboard?

Chip Conley: Well, you mentioned Oscar Wilde earlier, I think one of my favorite quotes of all time is “Be yourself. Everyone else is taken.”

Tim Ferriss: Yeah, that’s a great one.

Chip Conley: That would be my Oscar Wilde quote I would probably slap up there. You know, I don’t know. I think the thing I probably would — yeah, I’d probably stick with that.

Tim Ferriss: “Be yourself. Everyone else is taken.” Chip, this is so much fun.

Chip Conley: Yeah.

Tim Ferriss: It’s really nice to see you again.

Chip Conley: It’s great to be here. The first of many times, not necessarily on this show, but just hanging out.

Tim Ferriss: Oh yeah. Oh yeah. We’re neighbors at this point and people can say hello on Twitter @ChipConley, Facebook, ChipConleyAuthor, LinkedIn, ChipConleySF, and we’ll link to all this in the show notes so for people who are watching or listening to this, that’s tim.blog/podcast. You can find links to all of this, so just search for Chip. Also, you have ModernElderAcademy.org that people can check out. Anything else, parting comments, thoughts, suggestions, anything you’d like to mention before we wrap up?

Chip Conley: No, I think I would just finish by just saying that the more we fear aging, the more we’re playing on the playing field of the youth. There’s nothing wrong with that, but if your intent is to just stay looking young the rest of your life, you’re playing on the wrong playing field. That’s a losing battle at some point. Some of us are embarrassed to see people who are continuing 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. It’s part of the reason why we get happier as we get older.

Tim Ferriss: Yeah, and you mentioned the anxiety equals — don’t tell me. It’s anxiety equals uncertainty times hope —

Chip Conley: Powerlessness.

Tim Ferriss: Powerlessness.

Chip Conley: Yes.

Tim Ferriss: That ties into Marcus Aurelius really nicely as well because it’s in a sense it was this Stoic philosophical system certainly as practiced by Marcus Aurelius entailed a lot of separating what you can control from what you can’t and the possible from the inevitable. Certainly it’s hard to think of someone offhand who thought of death and mortality more than Marcus Aurelius, but learn to befriend it in a way and not to fight something that sort of left to become this amorphous source of anxiety can really be paralyzing when as you’re doing right now, learning to embrace it and live in liminal.

Chip Conley: Yup. Embrace the elder, there you go. Own the word. I’m trying to bring back the word.

Tim Ferriss: Elder.

Chip Conley: And separate from elderly, which is to me, that’s the last 10 years of your life.

Tim Ferriss: Well, for now, modern elder. Chip, thank you so much for the time.

Chip Conley: Thank you, Tim. Great to be here.

Tim Ferriss: Really fun. And to everyone listening and to anybody watching, thank you for joining us and until next time, be well, be safe, experiment often, and learn to live in liminal. Pick up surfing or Spanish or something else that you’ve been putting off because it’s not too late. Thanks, everybody.

 

Posted on: June 24, 2019.

Please check out Tribe of Mentors, my newest book, which shares short, tactical life advice from 100+ world-class performers. Many of the world's most famous entrepreneurs, athletes, investors, poker players, and artists are part of the book. The tips and strategies in Tribe of Mentors have already changed my life, and I hope the same for you. Click here for a sample chapter and full details. Roughly 90% of the guests have never appeared on my podcast.

Who was interviewed? Here's a very partial list: tech icons (founders of Facebook, Twitter, LinkedIn, Craigslist, Pinterest, Spotify, Salesforce, Dropbox, and more), Jimmy Fallon, Arianna Huffington, Brandon Stanton (Humans of New York), Lord Rabbi Jonathan Sacks, Ayaan Hirsi Ali, Ben Stiller, Maurice Ashley (first African-American Grandmaster of chess), Brené Brown (researcher and bestselling author), Rick Rubin (legendary music producer), Temple Grandin (animal behavior expert and autism activist), Franklin Leonard (The Black List), Dara Torres (12-time Olympic medalist in swimming), David Lynch (director), Kelly Slater (surfing legend), Bozoma Saint John (Beats/Apple/Uber), Lewis Cantley (famed cancer researcher), Maria Sharapova, Chris Anderson (curator of TED), Terry Crews, Greg Norman (golf icon), Vitalik Buterin (creator of Ethereum), and nearly 100 more. Check it all out by clicking here.

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