0:14
My friendship, welcome to the Tim Ferriss Show. I'm so happy TO BE HERE.
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0:21
SO, we've known each other a long time.
0:23
And it's so nice to see you again, and I'm thrilled that we were able to coordinate uniforms Yes.
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with our respective tailors.
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We will be busking downtown Austin later today for change, where you are a new citizen. Yeah.
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We're moving here shortly.
0:37
Yeah, it's a beautiful town. Yeah, it really is.
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And you know, I thought we would start, and this may seem somber, but since this is something we're just catching up with uh maybe an hour ago over lunch.
0:50
Uh can you talk about your current medical state of affairs, if you wouldn't mind, because I think I think it's a wedge that leads us into discussions that can be pretty far-ranging. Sure. If you wouldn't mind.
1:07
Uh no, no problem at all.
1:07
Um on the second day of a book tour 5 months ago, the day before I was at a TED Speakers Dinner, so the day before giving a TED Talk, I found out I I have intermediate stage prostate cancer.
1:20
And it came as a complete surprise.
1:20
My urologist had said, after doing a biopsy, probably a 20% chance you've got a problem here.
1:29
But as it turns out, I had a problem.
1:31
And so since then, I've had a few different tests, and the good news is I'm right on the cusp of serious versus sort of not not serious.
1:41
And so so far, we've just looked at the alternative health approach.
1:44
But I'm all about Western medicine.
1:46
When I need to bring the the cavalry across the plantation to to sort of say yes, you know, I'll probably I'm young enough, I'm 58, probably going to live another 30 to 40 years.
1:57
Probably will have my prostate taken out in the next couple years.
2:02
What is What does that feel like to you to realize or to say?
2:07
Like and what is that for people who may not know, like what does that mean?
2:08
I mean, is prostate like an appendix?
2:09
You don't really need it?
2:12
Well, you There does have certain functions which we can get graphic and get into if you want to.
2:16
Um but let me say the first of all the big C, you know, the the cancer word is like what what what?
2:21
I have cancer and that The good news is prostate cancer as cancers go is actually a relatively tame cancer. But that was hard.
2:32
And then prostate, you know, the prostate women don't have a prostate, men do.
2:35
And it's uh part of It's It has a little bit to do with sexual functioning.
2:40
Actually, it's more to do with actually the secretion that happens in semen.
2:45
So, if you have your prostate taken out, you're no longer going to ejaculate.
2:47
Um it does mean you still could potentially have an orgasm.
2:53
Uh but you um you just will have a dry orgasm.
2:56
This is really crazy to be talking about this in the first 5 minutes.
3:02
Feel like This is like this is like the mirror, you know, it's like the Friends cover, you know, naked nanny or something like We're skipping the foreplay.
3:10
This is how we, you know, keep you uh on the the podcast for an hour and a half.
3:14
Um so, all I can say is um cancer can be a teacher. Yeah.
3:21
And for me it's been a uh a reminder of the vulnerability that we can have uh as well as what level of control you do have over your body.
3:29
And so, the fact that I've been sort of focusing on making myself healthier and so far until a couple days ago this the test results have looked really good.
3:40
Now there's a test result that's PSA score that shows that it's spiked a little bit, so we'll have to sort of see with an ultrasound this next week.
3:45
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's creates a certain level of urgency in life.
3:59
I had a flatline experience where I went to the other side 10 and a half years ago and that did the same thing for me. So That was in St. Louis. That was in St. Louis.
4:07
Thank you for the memory on that one. Yes, it was in St.
4:10
Louis and I had was had been going through a difficult time and had a broken ankle from a bachelor party with Gavin Newsom and I had a cut on my leg with 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.
4:34
And so so I've had a couple experiences of just being a wake-up call which is an interesting term for a hotelier and have a wake-up call and so I say, you know what?
4:45
You are still alive but are you living your life the way you want to live your life?
4:51
And the reason I I thought this could be as good a place as any to start is that in all my interaction with you from the very beginning which goes back at least 10 years probably more.
5:03
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 segway into conversations about some of those chapter changes and how you thought through them and also just impactful
5:26
periods in your life 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 was it that you shared when we were having lunch which I think It's beautiful. It's appropriate here. The meaning of It's appropriate here.
5:39
The meaning of life is to find your gift and the purpose of life is to give it it Now it's been actually sometimes called Shakespeare, sometimes called Picasso.
5:49
Picasso has a great quote, too, that relates to modern elder, which is "Computers are useless.
5:53
They only give you answers."
5:55
We'll come back to that one.
5:55
But, but yeah, the idea of finding your gift.
6:00
Meaning of life is to find your gift, the purpose of life is to give it away.
6:05
And that I think I've 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.
6:18
And for people who who aren't familiar with with Chip, uh, what is what is the introduction, the context you'd like to give, or if it's easier, how would someone introduce you at a speaking engagement?
6:29
Well, the way they introduce me at speaking engagements often is, "This is the guy who's disrupted his favorite industry twice."
6:36
And that hap- That industry happens to be hospitality.
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I was one of the first boutique hoteliers, along with Ian Schrager and Bill Kimpton.
6:40
I I started a company called Joie de Vivre.
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Joie de Vivre is based in San Francisco, created 52 boutique hotels, second largest boutique hotelier in the US.
6:50
And then, after 24 years of running that, soon after I had my flatline experience, which was a a wake-up call to say I didn't want to be running that company anymore, I was asked, uh, 6 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.
7:08
So, I have been a disruptor twice, and, um, yeah, so I that's my I've also written five books, and I most recently have created this the world's first midlife wisdom school called the Modern Elder Academy.
7:25
And we're going to talk about all of this.
7:27
Yeah, so many places to go.
7:27
I thought we would start with one of your more glamorous periods.
7:30
Could you, uh, tell us how you got into commercial real estate?
7:34
You know, I I grew up in California, so everybody in California has sort of like the real estate bug, and, um, I went to work for my summer my my uncle the summer and then uh almost most of my junior year at Stanford.
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Uh he was a commercial real estate developer in in Silicon Valley. This was 1980.
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It was full of orange groves.
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Silicon Valley was nothing like it is today.
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And I just saw everybody making money and sort of having a good time in commercial real estate.
8:00
What I was fascinated by was the creative side of it.
8:03
How do you How do you design environments?
8:05
And um ultimately I went to Stanford Business School straight out of undergrad and focused on real estate there and then went to work for a real estate developer um in San Francisco for a couple years.
8:17
That was after Stanford Business after Stanford Business School and then that's when I said, "You know what?
8:20
The thing the part of real estate that's really interesting is hotels."
8:24
What did you think you were going to do as an undergrad?
8:26
Did you know real estate was the answer?
8:27
Let's say the freshman sophomore year.
8:29
What what did what what what did you envision adultship doing in the world?
8:34
I thought I was going to be a philosopher.
8:36
You and I could have hung out together.
8:37
Well, yeah, but you are you are kind of Do a little Seneca you know, Marcus Aurelius debate.
8:42
Um you know, Before it was cool. Yeah, exactly.
8:46
No, I yeah, I took a class called gods god self in the body or something like that in freshman year. I just loved it.
8:53
I So I thought for a lot but you know, everybody said like, "What are you going to do with a philosophy major?"
8:55
Um So I thought I might go into politics like helping in a in a governmental role.
9:03
Um and I went I did a summer in DC as an intern and didn't love it.
9:06
And so uh business became sort of the next thing.
9:11
Uh and I guess I have been sort of a philosopher in business.
9:12
I certainly that's part of the reason I like writing books about it.
9:15
Um but I no, I had no idea I was going to get into commercial real estate.
9:19
And and then at 26 at 20 at my 26th birthday I finished a business plan to create this boutique hotel company called Joie de Vivre, which is a really impractical name for a company especially in the US because it's hard to pronounce, hard to spell, most people don't know what it means. It means joy of life.
9:33
But very few companies in the world have a mission statement that's also the name of the company. Mm.
9:39
And that's what really resonated with me.
9:42
And yeah, bought a broken down motel, pay by the hour motel in the Tenderloin, called it called it the Phoenix, and it became a rock and roll hotel and a big sensation.
9:50
And that's how I got started.
9:53
So, if we back up a little bit and revisit Stanford Business School.
9:56
In in the course of preparing for this, read about brainstorming sessions that you did.
10:04
I think they were a few hours in length. Yeah.
10:08
I hesitate to say four hours because of course I'm the four hour guy, but I think that in the in the article it was four hours. Yes.
10:15
Uh, and there were some there were some other characters involved.
10:18
You've done your research.
10:19
Whose names maybe recognizable.
10:19
I think Seth Godin was also one.
10:23
Seth and I wrote our first we both wrote our first books together that when we were in our second year of business school.
10:28
Yeah, this group of us five guys all we're the five youngest guys in the class.
10:33
Two of us went straight into business school, the other three had had one year off.
10:36
And we were sort of not well liked generally within the business school class because we were just the innocent naive, you know, dumb shits.
10:43
Yeah, so so we sort of created our own little club.
10:45
And we were brainstorming business ideas.
10:48
And um Was there a Was there a format to it?
10:52
Did you guys meet on a regular basis?
10:54
met on a regular basis and it was really the best way to describe it it was each one of us would bring an idea to the table and then we'd critique it.
11:00
And Seth is a you know, a good critic. Critic. Very good critic.
11:06
And uh, so that was partly how we how we I got to know Seth and ultimately Seth and I didn't love business school and so our second year 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."
11:28
Use that Stanford while you can.
11:29
And we did and we created a book called Business Rules of thumb and it came out long long long time ago.
11:33
And um yeah, Seth at that point had caught the bug.
11:38
He knew he was going to write books.
11:39
I did I hadn't caught the bug.
11:39
It wasn't until about gosh, 16, 18 years later that I I wrote my what I consider my first book.
11:47
I don't actually count that book as one of my five books, unfortunately.
11:50
I don't think Seth counts it as as as well.
11:53
It's super if if people are listening and they like the idea of forming a group like this. Yes.
12:00
Uh because I I think that at least in the piece that I'd taken a look at the the consensus of some of the people in the group was that you learned more through those sessions than you did through the course work. Yeah.
12:14
So if if people out there listening and they think they want to create their own group whether they call it a mastermind or a brainstorming group or whatever it might be where they have the opportunity to put people say in the hot seat and and uh to have their ideas critiqued and to offer the same.
12:29
Do you have any guidelines or recommendations on how to do that well or what the necessary ingredients are?
12:35
Well, I think the most important thing is to have clarity about what the purpose is.
12:38
It like that's sort of true in life and true with any business, but it's actually true with a group.
12:42
And so the fact that we knew this was a brainstorm around business ideas, mostly entrepreneurial ideas, was absolutely clear.
12:49
Um if you don't have that clear, then people are using it for different purposes.
12:53
And it's fine to have different purposes as long as people know each other's agenda. So I think that's key.
12:59
I think another thing that's key is is while it can be like intellectual jousting and so it can be hardcore, it there has to be at least an underlying respect.
13:08
If the purpose of it is to just, you know, skewer each other, um you know, people start to shut down or start stop showing up. Yeah.
13:16
And so that's that's critical.
13:16
And at the end of the time we also had a good time.
13:19
I think that was a big piece of it as well.
13:22
How how long did they last?
13:24
They could I mean, well we did it for the two years that we were doing the business school.
13:26
What was What was The big The big purpose really was I think all five of us wanted to graduate and become entrepreneurs straight out of business school.
13:36
I don't think any of the five of us did that.
13:38
Um some of us went to work for very entrepreneurial ventures.
13:43
Um but I think what we really wanted to do was incubate some interesting ideas such that in that second year of business school we might determine if we were going to actually create a business plan.
13:52
I think it probably it did incubate an idea.
13:54
I had an idea in one of those sessions where I talked about creating sort of an urban retreat resort um where people would go and uh go to workshops and classes and and it would be a place where you could sort of get away from the city but in the city. Mhm.
14:11
Uh 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.
14:18
It was sort of like take that place bookstore's dedicated to you.
14:20
The bookstore's dedicated to me. Thank you.
14:22
I It is um because I gave some money.
14:25
It's the only reason, not because I'm a great author or anything like that.
14:26
But you know, so the bottom line is I said why not Why isn't there an Esalen in the city?
14:32
And that was an idea that percolated.
14:34
Ultimately it it led me to buying a no-tell motel in the Tenderloin of San Francisco, which is not exactly um that idea.
14:42
But I think it was was this roughly?
14:45
So '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 inner in the Tenderloin.
14:52
So sometimes you you know, you're planting a seed.
14:56
I mean, what's great about uh life is you know, your brain, your soul, your spirit, your ability to channel something deeper than you from far off in the in the cosmos.
15:05
These are things that actually sometimes take time. Yeah.
15:10
And so planting seeds early is is wise.
15:13
Well, I this is part of the reason I wanted to ask you what you thought you might be or what grabbed you as an undergrad because if I'm maybe I'm forcing a narrative, but I don't think so because I've I've seen this before in that you have philosophy, it grabs you, it has great appeal, but you don't know what to do with it at the time, so you bookmark it. Right.
15:34
Don't expect to ever come back to it. Yeah.
15:36
And then you plan on X, but you can't do it right away.
15:39
And it seems to me, at least for myself, I try to do this.
15:42
If something really excites me, I assume that there's probably a place for it or a role for it.
15:47
It just might have to incubate for a while. Exactly. The question is timing. Yeah.
15:52
And how what form it'll take.
15:52
So, yeah, I think for me the the thing that was really interesting is that writing that book with Seth the second year um incubated 16 or 18 years later in in my first official book, which was called um The Rebel Rules Daring to Be Yourself in Business.
16:08
And Richard Branson wrote the forward.
16:10
And I think that for me that thing that became clear to me was and and and has been a practice my whole business career is making a weekly inventory of what I learned that week has been essential.
16:24
And I think that every Friday afternoon, I started doing it when I was in my mid-20s.
16:28
And I would almost do a half hour to an hour, usually on Friday afternoon, sometimes over the weekend, and said, "Here are the some of my key lessons of the week."
16:38
And I created a wisdom book, and it was called The Wisdom Book, and that wisdom book was the collection of lessons that I was learning along the way.
16:47
And I I it wasn't like I went to the wisdom book all that often to look at it.
16:51
I did do it in in dark times I would go there.
16:55
But generally, it was just the act of putting it down that was planting a seed in my consciousness to take notice. Mhm.
17:03
When did you stop doing that?
17:03
Or did you stop doing that? it. You still do it. do it. So, if if I may Yeah. uh And today's Saturday.
17:11
Today's Saturday, so So, Friday on the flight to Austin, which I lost the flight, missed the flight, I went had to flight to Houston and then take a a lift from Houston here. Um I took I did my list.
17:19
And this list was a really interesting list because this was a weird week.
17:24
Now obviously this is going to be a um on on uh out in the public in a few weeks.
17:31
But this week was the week that a New York Times article came out about my our new Modern Elder Academy and it as people have said people say it's a great article but it's not really very accurate.
17:44
And to my mind a great article is very accurate.
17:46
So I don't love this article and I've it's forced me to reacquaint myself with one of Victor Frankl's famous three-liner three lines from Man's Search for Meaning.
17:58
And so that went into my lessons this week which was uh between stimulus and response there is a space.
18:05
In that space is your power to choose your response.
18:07
And in your response lies your growth and your freedom.
18:12
And I had to really watch that I would look at those three sentences over and over because I was just getting more and more indignant and almost feeling betrayed by the journalist because you know she just didn't she didn't she wasn't she didn't give a factual story.
18:27
So long story short is I I this week my list of lessons were very much about emotional regulation and which is really something that we learn as we get older. Yeah.
18:36
Um you know there's a lot of things that as we get older we are very aware of the things that actually get worse with time but we're actually not as aware of the things that get better with time.
18:47
How long is say the total set of bullets for this week? Is it a page? Is it two pages? It depends on the week.
18:56
Um the the bloodier the week the more the more bullet points there are.
19:01
Um the average week is about five. Five bullets? Five bullets of Oh. Oh look at that.
19:07
On Fridays Oh wow that's interesting.
19:08
Well that but my your bullets and my bullets are different.
19:11
Um my bullets are really actually lessons.
19:15
Yours are like here's my here's the my favorite spatula I found this week and your lessons learned. No. like that. No.
19:20
Um they're actually Yeah, they're they're they're deep and sometimes painful.
19:24
Um this week there were probably 12 bullets and and some of you know, some of them were like tactical Yeah, are you are you willing to share any of them?
19:33
Yeah, like one of them was you know, I I said to my PR person I got this article on my own, you know, I know the off the the journalist um we're not I wouldn't say we're friends, but we know each other moderately well.
19:48
And I think she'd probably prefer just the one-on-one and and she did.
19:53
But I didn't necessarily have someone there to sort of say, "Hey, yeah, Chip said these things and um why are those not in the article and you put something else in there that he didn't say?"
20:02
And so it it I think part of it for me was, "Okay, you know, yes, it's it's normal to have someone there as a PR specialist especially for an article as important as say the New York Times would be.
20:16
Um that's another example.
20:16
The I gave the Frank Luntz example.
20:18
You know, another one is when things are troubled it's the most important time for what the higher you are in an organization to be calm.
20:32
Because um our mirror neurons mean that our emotions are contagious.
20:38
And so and everybody tends to look at the most senior person to see how they're reacting to something.
20:43
And so when something goes askew uh people look to the leadership to see, you know, are they are they sweating? Yeah.
20:51
And I'm not saying that we shouldn't be authentic and transparent and um but you can be both uh vulnerable and a visionary at the same time.
21:00
You can also be very serious and calm at the same time. Yeah, for sure. If need be, yeah.
21:03
So I think that I've I've tried to to be that way and not, you know, get like so wrapped up in a reaction.
21:11
You know, Frankl's quote is really about reaction. Response versus react.
21:16
And the the longer we're on this earth, often the better we get at being responsive as opposed to reactive.
21:22
What What other practices or books or resources, anything at all, has helped you in developing your What was the phrase you used?
21:32
Not emotional resilience regulation.
21:36
Yeah, um I think uh I've been lucky enough I'm not I'm like awful at at yoga.
21:42
Um people say, "Oh, you got the yoga body.
21:43
You sort of seem like you're like a yoga guy."
21:45
And I think, "I'm I'm really tight.
21:47
I have a hard time with that."
21:48
And but I'm really good at meditation.
21:50
And I I took to it 35 years ago, um and I've integrated into my life ever since then.
21:58
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.
22:11
And uh you know, that actually is a way of, you know, regulating myself.
22:16
Clearly, exercise, you know, and just getting it out of your system, and getting out of your brain.
22:22
I mean, so much of emotional regulation is learning to get out of your brain.
22:25
And And so that's I've done that, too.
22:28
But I will say back to the yoga for a second.
22:31
I think there's two ways that I look at life, um and that's to be in a in attainment mode, trying to attain something, and in an attunement mode.
22:41
And what I've found is that I'm My natural tendency is very attain-oriented. Yeah.
22:46
And when I'm in the attain mode, I often have to atone afterwards, because um I have sharp elbows, and I'm just going for what I want.
22:55
Attain and attune or atone.
22:58
Well, it's attain Yeah, leads to atonement. Attune leads to atone.
23:02
And there's So for me that's been something for about a year now.
23:04
I've been able to sort of see myself.
23:06
And so ask myself am I stirred up because I'm in the attain mode?
23:12
Attain is perfectly fine.
23:15
Yet yoga is not an attain sport.
23:18
Surfing, which I at age 57, 56, 57, and 58 now, I started learning to surf.
23:24
Um this is not an attain sport. Yeah.
23:27
The key is to attune yourself to the wave. Yeah.
23:29
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. Mhm.
23:38
And is your meditation practice mostly focusing on the breath and letting arise whatever arises without trying to modify it or what is your pri- What is your internal practice look like when you sit for those 10 minutes?
23:50
I have a lot You know, I so the So I've done TM and that that's a 20-minute practice and that's the that's sort of my core go-to that I do. Yeah, but mantra-based.
23:58
Try to do it morning and afternoon.
23:58
At minimum I do it the morning.
24:03
The I do a lot of other ones as well.
24:05
There's a loving kindness meditation that I, you know, sometimes will do which is sort of when I'm frankly when I'm most stirred up about someone in particular, I could sort of go that that that direction.
24:14
I love Vipassanā, but that's more of a an extended silent meditation practice.
24:21
Um and I like right now, 2 years ago I was in Loreto Bay in Baja kayaking with a guy named Mark Coleman who wrote a book called Awaken the Wild, beautiful book.
24:31
Um 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.
24:43
Um so I think but but at the simplest thing to do, I I think of two things.
24:48
It's just it's breathing. Learning how to breathe.
24:49
The thing that I do that's that Chip Conley little trademark is I think of louvred windows in my forehead. Hold on a sec. What windows?
24:58
Louvered, like you know you know like sort of glass louvered windows so that you sort of open them and they just sort of like they turn. Okay.
25:05
So, actually the reason I like them is we have them at the Phoenix Hotel my first company.
25:08
sort of like the they make me think of really old Volkswagen Yeah.
25:12
uh camper buses that have that type of rotational window. Exactly.
25:16
So, you have a rotational window.
25:18
in an air conditioning duct in a car. Exactly.
25:20
Imagine that on your forehead. Okay.
25:23
And so, what I do is I breathe through my forehead.
25:28
And then I breathe out my forehead.
25:28
And this is how I turn down the heat on my brain.
25:34
I mean truly this is like my the Chip Conley approach to works, right?
25:38
Yeah, so that's you know, but I yes I this the the core thing I tend to do is the the TM. The TM.
25:44
And uh for people who are interested in in the second you mentioned, which is loving kindness meditation, also known or called meta meta m e t t a, uh there are some fantastic guided meditations that you can listen to out there.
25:55
Like Jack Kornfield has some fantastic versions of that.
26:00
There's also a really fascinating guy named Chade-Meng Tan who wrote a book called Joy on Demand that that gets into this.
26:07
And Search Inside Yourself, too.
26:09
And Search Inside Yourself.
26:09
Uh which became the most popular employee class at Google at one point or on a waiting list of like 6 to 12 months or something like that.
26:18
So, let's let's go back to something you mentioned.
26:20
Uh your first book, the first book you count.
26:25
How old were you when you wrote that roughly? Do you remember?
26:28
38 uh when I wrote it and um yeah, and I had so I'd been running my company for a dozen years.
26:34
Uh Joie de Vivre and How did you get Richard Branson to write the forward? Great question.
26:42
You know, um so uh Gavin Newsom, at that point he was the mayor of San Francisco and I he was my first mentee.
26:49
I was I mentored him and mentee'd.
26:50
So, So we went together to see him and give a talk at the Virgin record store in San Francisco. that. used to exist.
26:58
So it was actually around the launch of that record store.
27:00
You know, it's hard to imagine Right on Market Street.
27:03
Yeah, I remember like a record store, really?
27:04
Um, wasn't that long ago though.
27:06
But um, so we went there and we were there with like the head of protocol for the city.
27:12
And actually this was before Gavin was mayor.
27:14
He was just on the board of supervisors in San Francisco. And we I don't know.
27:17
He just took a liking to both of us.
27:20
And so he said, you know, can we hang out?
27:24
How did you meet him in person?
27:26
We were literally in line to actually have him sign our book. And it was me and Gavin.
27:29
And so when we came up he just ended up spending a bunch of time with us.
27:32
And he we waited a little bit later and he talked with us just the two of us.
27:37
And we went out and had a meal.
27:37
You know, I'm going to keep chipping away at this, no pun intended.
27:40
So you walk up, you're good with words.
27:43
Gavin's also good with words.
27:44
So you guys walk up, there's a long line of people.
27:49
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 I can't I can't remember the names right now, but I learned his parents' names.
28:07
His mother and his father.
28:07
And so I went in the front there was something.
28:10
I went in the front line and I said, so what influence did so-and-so and so-and-so have on who you are today?
28:18
And he looked at me like, how do you know that?
28:22
And then so that led to the conversation that led to a longer conversation. Amazing.
28:27
Now did you propose hanging out after the signing or did he? Did Gavin? day.
28:32
So and we just had lunch the next day.
28:34
And 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.
28:47
So it was there was some there's some benefit to him as well.
28:50
How did you make the jump from him being impressed that you knew his parents' names to meeting the next day?
28:56
Um you know actually he had he had an assistant there.
28:58
And so and his assistant actually did know me and knew Gavin.
29:02
So she was like wise enough to know these are two and she said so he said can you go talk to April over there?
29:09
And so we went over and talked to April and April said you know what he's got some time to schedule tomorrow and so Amazing.
29:18
And then flash forward and you have a forward from Richard Branson.
29:20
So yeah and he so ultimately ultimately he said you know I'll write it but you're going to write the first first draft and you know and and then he he edited it and it went in it.
29:30
All right so we're going to get continue this this forward and backwards chronology if if I can even call it such. Uh who is Brenda Lee?
29:40
And this may go somewhere it may not go anywhere but Brenda Lee is this 4-ft 10-in although she's 5-ft 6-in with her beehive hairstyle Nashville gal famous country western singer and out of the blue her bus her pink bus was driving through the Tenderloin in San Francisco looking for a place to stay and this is about a month after we opened my first hotel the Phoenix.
30:08
Paint a picture of the Tenderloin at this point.
30:11
Well it's the same as it is now.
30:13
hasn't changed that much.
30:14
a lot of 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.
30:20
It's right and it's right near Union Square and the and the hotel district.
30:23
So we were sort of we were the gateway to the Tenderloin but we were on the opposite side of the Tenderloin from where the the nicer part of the Tenderloin and Union Square was.
30:31
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.
30:36
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.
30:49
to Arlo Guthrie when I grew up.
30:51
god, so this land is your land, this is is that Um, amazing, yeah.
30:55
So Arlo Guthrie's in the hotel because the Great American Music Hall is two blocks away.
31:00
Brenda Lee comes in with her bus and we have bus parking.
31:02
So one of the beautiful things about the Phoenix is it had free bus parking which a band's going to appreciate.
31:06
And she checks in and all of the sudden we'd become a rock and roll hotel.
31:10
We had Arlo Guthrie and Brenda Lee and that led to, you know, Nirvana, Pearl Jam, you know, David Bowie, Red Hot Chili Peppers, you know, Okay.
31:21
everybody you can imagine staying there over the years.
31:24
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.
31:26
I know there's more to the story.
31:29
No, there's more to the story.
31:30
No, no, no, so how how did Okay, so they you you have manifested or chanced upon this luck of having these two guests at the same time. Yeah.
31:41
How do you how does that then get converted into a reputation?
31:42
Do they just recommend to other people? Do you seize upon that?
31:47
Hey, can we take some photos?
31:48
How does it how does it happen?
31:50
so my my business school brain was saying, okay, well, who's the person who books all of the hotel rooms for bands coming through town?
31:56
And and I'd gotten to know Bill Graham who's a music impresario, a concert promoter and he had said, well, it's usually the concert, you know, whoever's booking the concert, they're doing it.
32:06
So I tried to we tried to market to them.
32:07
Then we tried to market to the venues like Slim's or the Great American Music Hall or the Fillmore.
32:13
That made sense and then we found out, oh, there's these travel agents who specialize in entertainment travel.
32:15
So let's go to market to them.
32:17
To be honest with you, none of those worked all that well. They worked okay.
32:22
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 the tour manager.
32:31
So the tour manager was usually a guy, almost always a guy, about three to five years older than the band.
32:35
His job was to make sure there was no overdoses and no groupies.
32:39
And because a groupie might mean the guy like doesn't show up at the show, and of course an overdose could do that as well.
32:45
And he was by the time he got to San Francisco, he was so stressed out because usually the tour started on the East Coast, and by the time he got to San Francisco So, here's what we did.
32:55
We had one room of our 44 rooms that was um a massage treatment room.
32:58
Now, back in the old days when it was a pay-by-the-hour place, you can imagine what happened in there.
33:02
But, we cleaned it up and we made it into a legitimate massage studio.
33:06
And so, we offered to tour managers, um 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.
33:18
And so, back in the day when we started doing that Now, remember, this is pre-cell phones, pre-internet, uh pre-frankly laptop computers.
33:26
People had satellite phones.
33:31
But, mainly what they were doing was going on the house phone and the tour manager's calling his friends, and then sometimes writing a letter and sending it out to them in old-school US mail, and saying, "There's this place in San Francisco that actually gives you a free massage."
33:44
And that's when I realized that really great entrepreneurs don't deliver on your expectations. Well, they hopefully do.
33:53
They deliver on your expectations, they deliver on your desires, but the thing they get right is this thing at the peak of the pyramid.
33:58
I wrote a book called Peak: How Great Companies Get Their Mojo from Maslow.
34:03
It's meeting the unrecognized needs of whomever your customer is.
34:06
And in my case, figuring out that the customer was not all those other people, it's actually the tour manager.
34:12
And what's his unrecognized need?
34:13
It's basically to like chill and to relax and then get a free massage. That's incredible.
34:22
And because it it it also acts as a contrast in my mind to um a maxim that is often often used, but I think often inaccurate which is you granted you had a you had this motel/hotel but you need money to make money.
34:39
But if you look at what you did in that particular case, I mean you identified who your actual customer was.
34:46
It's like the the the unspoken customer. Yeah. Right.
34:51
And then no one told me no one ever said that it was the terminal. Yeah.
34:54
And then the un- the unspoken need and the I mean the cost to offer that service is just it a rounding error.
35:04
I love I you know it's a great it's a great entrepreneurial story to sort of suggest that sometimes it's not the thing that's most obvious and it's not the thing that's the most expensive. Yeah.
35:12
Um but this idea of the unrecognized need, how do you mind read your customer well enough to know what it is that they would love?
35:18
We have a hotel later that we created which you and I have been to the Hotel Vitale. Sure.
35:22
I wrote a bunch of two of my books there. Oh, thank you. Yeah.
35:28
Um well, so long story short Hotel Vitale like the Phoenix is in like the worst in San Francisco and the Vitale sort of like the best neighborhood is right on the bay on the on the Embarcadero right across from the ferry building and the and the um the farmers market.
35:41
So the unrecognized need for the customer we wanted there.
35:44
So the Vitale means vitality in Latin or in Italian.
35:49
And we wanted to create a hotel that was sort of what we called for the person who was post W and pre four seasons.
35:52
We called you know David Brooks would call them the bourgeois bohemian so the bobo.
36:00
The the the hospitality tweeners.
36:02
Yes, the hospitality tweener who who who sort of was looking for that.
36:03
And so our point of view was we said it this is a person who's who reads real simple and dwell.
36:10
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.
36:22
And so we ended up creating on the top floor of the Hotel Vitale when we launched, uh 15 years ago, a yoga studio on the penthouse level that had free yoga classes every morning.
36:32
Then my my investors looked at me like, and they're all guys, looked at me like, "What are you doing?"
36:37
Now, today this might make sense.
36:39
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 on the on the on the penthouse level.
36:49
Like, why would we ever do that?"
36:49
And I said, "Well, because we're going to be the first ones doing it."
36:52
And so then they said, "Well, look at all of the customer satisfaction forms you've gotten from people in financial district hotels.
36:59
And have they asked for a yoga studio?"
37:02
And the answer was, "No, 10,000 of them. We looked at 10,000.
37:04
Not one person ever said, 'Why don't you have a yoga studio in your hotel?'" Yeah.
37:08
But if you're good, and if you really understand your customer, it goes beyond the expectations, beyond the desires, beyond focus groups.
37:14
It's the thing you know that they want next that they don't even know they don't want.
37:18
They don't even know they want.
37:20
So long story short is the yoga studio had a line out the door, and within a a month, we had we were in, you know, New York Times, LA Times, uh Wall Street Journal had stories about this new sort of hotel that's oriented toward business travelers who want to stay healthy.
37:34
And the Hotel Vitale ended up becoming the most successful upscale hotel in San Francisco.
37:40
It's it's uh it's reminiscent to me of uh and this could be apocryphal.
37:44
I don't know if this is a real anecdote.
37:45
It's kind of like every quote is attributed to Abraham Lincoln or Oscar Wilde on the internet, but Did you know they had a thing, the two of them? No. I'm kidding. A quote-off.
37:59
Uh Henry Ford, I think uh you know, if if I had asked people what they wanted, they would have said a faster horse. That's Henry Ford. Yeah.
38:05
At least attributed to him.
38:05
Uh we can't ask him if he did it.
38:07
and uh to to to look under the under the hood on that decision a little bit.
38:12
So the the first is, and this is something that I'm constantly maybe constantly is too strong a word, but I I always consider when I'm looking at launches or books or television shows or documentaries, whatever it is, is being first.
38:27
I think the like the doing something the first time is really can be really undervalued.
38:33
Like the the being second, different story, right?
38:39
Being first is can can be very very newsworthy in and of itself.
38:45
Also, what would you have done if it if it hadn't worked?
38:50
We would have We would have turned it into a suite. Right?
38:52
I mean So, the key the key there and it's that you just said it exactly right, which is my point to my investors was give me 6 months. Let me try this.
38:59
We can ratchet and make it into a suite.
39:03
And that in fact after we sold the hotel eventually later, that's what they did.
39:10
Um but I said give me that time because this was not going to be insurmountable if it didn't work out.
39:14
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.
39:23
And but I think the the point on that is to sort of say, "Okay, so how do you try things and and do something small enough but that could have a big impact that is easily solvable if it doesn't work?" Right.
39:37
And which is also uh something that can be tied into Richard Branson, right?
39:41
Because people think of Richard Branson as this throw caution to the wind maverick who risks it all despite the odds.
39:49
And he's been on the podcast, but uh you've spent time with him.
39:54
And if you look at I believe it was Virgin Atlantic Mhm.
39:59
where uh he he did he took so many in-between steps to cap the downside on something that could be unmitigated, a complete disaster, right? Airlines.
40:13
It's like magazines, restaurants.
40:14
Like you can really lose your And uh among other things, you know, tested with I thought I want to say like a poster board in an airport when a flight was canceled, something like Virgin Airlines and it was a chartered flight that he was going to book if he got enough people to sign up for Uh-huh.
40:31
you know, 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 uh in order to be able to give them back the plane Hm. if it didn't work. Right?
40:44
So, behind the scenes, uh he's actually making very, very calculated bets. He's a shrewd guy. Yeah. Super shrewd.
40:53
Yeah, and I think um you know, that one of the things I learned from my dad a long time ago is uh build the business plan as if it's not going to succeed.
41:00
I mean, imagine it succeeding and you're going to attract people for that investors, employees, but what's plan B, you know, and and how do you how do you have a solution for plan B?
41:11
And so, that's why I don't build bowling alleys.
41:16
You know, bowling alleys sort of like in terms of the shape of them is you know, you could you could have said in the past churches, but churches have become sort of popular for all kinds of uses post-church era.
41:24
Um but yeah, I think it's really critical to sort of understand what is plan B, C, and D.
41:30
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 Oh, yes.
41:41
So, could you explain for to for people who don't know who who Liz is?
41:45
So, Liz Lambert hates me because she even said on your podcast she hates me because I I did for her what now I hope and expect she does for other people, uh which is she reached out to me almost 20 years ago.
41:57
I had become a successful entrepreneur hotelier a boutique hotelier, and she was creating this funky little motel here in uh in Austin called the Hotel San Jose.
42:11
And similar to my Phoenix.
42:11
Um 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.
42:19
And so I came here and and gave her some suggestions.
42:21
And then I actually sent my general manager from the Phoenix, Monica Bernstein, down here to Austin basically to help her get launched. Why Why did you do that?
42:30
I was She wasn't here for that long, but she was here for I don't you know, I can't remember, but like weeks at the time.
42:35
I did it partly because I loved Liz.
42:38
You know, I love you know, she's an attorney who should never have been an attorney who's completely amazing as a designer.
42:44
So she's one of those hoteliers who designs her own hotels, which I love.
42:49
That's sort of like, you know, that like a restaurateur where the chef is the restaurateur.
42:51
So I think it's really beautiful.
42:53
And um so I just loved her passion and her sense of the you know, her joie de vivre, frankly.
43:01
Her the the she had took it such a joy in what she was doing.
43:02
And I I wanted her to succeed.
43:04
And so um you know, I I'm a big believer in karmic capitalism, which means sort of what goes around comes around.
43:13
And so uh me giving to Liz was going to pay back to me some in some way over time.
43:19
And and frankly it's been me doing that with a lot of different people and then having it come back reputationally.
43:23
You know, your reputation is one of the few things in your life that's portable.
43:28
Um and frankly it it arrives FedEx before you arrive somewhere because that's what happens with the reputation.
43:33
People know you before you arrive.
43:33
And I think that whether it's Liz or a variety of other people who I have tried to help in business um it's just helped my reputation in terms of how people see me.
43:44
And instead of people standing on the sidelines sort of like jeering, they're they're cheering.
43:50
They they want, you know, when when the New York Times article came out this weekend I didn't love it, I had a such a support network of people who just said, "You know what?
43:58
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.
44:02
And I think, you know, I once had a restaurateur um um, co-founded a restaurant with someone and no one really liked her.
44:08
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.
44:18
And I don't I'm not that way and I'm not saying that to say I'm the most likable person in the world, but I will absolutely say that I do a lot of things to make that karmic capitalism work for me in the world.
44:28
And, um, as such, uh, Liz was just an example of that.
44:32
And, uh, and the part reason she hates me is because now she feels the obligation to pass it on, pay it forward to someone else because she gets, you know, hit up all the time because she's she's just an amazing, uh, hotelier.
44:45
She's really incredible and, uh, she's done a lot of great things.
44:48
Bunkhouse and she has, uh, a number of just incredible, not just incredible properties, but incredibly different properties. they're soulful.
44:57
You know, at the end of one of her pools, you know, the Saint Cecilia pool here in in Austin, it just says, you know, the neon soul and there's something soulful to her places.
45:07
Uh, and so I I want to bet on people like that. Yeah.
45:10
Yeah, there there are a lot of parallels that I can see, uh, looking at the two of you side by side in some ways.
45:16
And I just just struck me that I did a number of staycations at, uh, Hotel San Vitale to work on books cuz I think I had read that Maya Angelou had had done that and I thought that's a great idea because at home I have all the usual dis- distractions and ways to procrastinate.
45:32
Let me treat this Moby would do that when he's Moby Moby would do that.
45:37
He'd go to a hotel room and just shut shut himself off for a week and to actually figure out, um, music. No kidding.
45:43
So, I have I have friends here, uh, I'll I'll I'll won't mention their names, but they're well-known filmmakers cuz they told me this just in a private conversation who use Hotel Saint Cecilia for Yeah.
45:54
their sort of staycation creative work as well.
45:56
So, so I'm going to jump to this text from Liz.
45:59
She had a number of questions.
46:01
I asked her, are there any particular questions or topics that you think could be interesting or fun to explore?
46:07
So one of them, she she gave me quite a few, but one of them was he, meaning you, should begin building his life at Viva as a young man.
46:12
It was the work of the first half of his life, a big sprawling family.
46:15
What made him decide to sell it when he did? Mhm. So great question.
46:20
You know, one thing, you know, to you aspiring entrepreneurs and uh people who are younger than me, just know that when you one of the natural tendencies is we hook our sense of self-esteem and self-worth to our businesses.
46:35
I remember in the early days of the Phoenix, I had I had one hotel before I had 52, and that one hotel when people people come to me and say, how are you doing, Chip?
46:42
I said, well, the Phoenix is doing fine.
46:45
And finally somebody called me on it.
46:46
It's like, you know, it's like I didn't say how I'm doing.
46:47
So my sense of worth and esteem had a lot to do with basically the roller coaster of my business.
46:57
Well, fortunately over time I realized that didn't have to be the case.
47:00
And it was that flatline experience I had uh 22 years into running my company that helped me to see that uh is this what I want to do the rest of my life?
47:11
Actually, it's not, and I thought it was going to be, but it wasn't.
47:13
And more than anything, I just realized that I started the company for creativity and freedom.
47:18
That's those are the things I said to myself um on one Friday afternoon when I said, you know, what did I learn this week about why I'm starting this business?
47:24
And 22 years later, I said, do I have any creativity and freedom in this business anymore?
47:29
No, I'm like running a company with 3,500 people.
47:32
So that's what led me to It was hard though.
47:33
It was very hard to sell a business that for a, you know, ultimately when I sold it it was 24 years, that has been your identity for most of your adult life.
47:42
But it was actually harder for other people than for me.
47:45
And that's the fascinating piece of it is I realized my identity had moved on.
47:51
I was ready for what's next, which was to become the world's leading expert on festivals.
47:56
And I didn't really want to be doing it anymore.
47:59
But I had to deal with other people's challenge in me changing my identity.
48:04
And there's lots of ways people change their identity.
48:06
You can get divorced, you can, you know, change your career completely, you can literally change your gender.
48:13
But in my case it was just changing the actual fact that I was the founder and CEO of what was the largest boutique hotel company, second largest in the in the US, but the largest hotel company, frankly, in the San Francisco Bay Area.
48:26
And for some people who liked having a 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.
48:34
And but at the end of the day it was the right decision.
48:39
So that as you just said it sounds like a difficult decision, or a maybe emotionally intense decision to work through.
48:50
And I mean, I remember when this was kind of happening, and and you mentioned just in passing here, you know, I I decided what I want to to do next should become the worldwide expert on festivals.
49:07
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?
49:18
Yeah, no, it's a great question.
49:18
I I made the decision I had this was going to kill me if I kept doing it.
49:24
And so I knew I needed to move on.
49:24
I didn't know where And And frankly, then you get into the freaky It was the in the Great Recession, the freaky thought of like, how am I going to sell this company in the bottom of the recession?
49:34
So what I hadn't yet found the new thing I was moving toward.
49:35
I knew what I was moving away from, but moving toward something is really important, because otherwise when you do leave it, you actually It's like when people retire, and they end up on a golf course depressed. Yeah.
49:49
Because they actually didn't move toward something, they just moved away from something, and they just sort of sort of like almost you know, just uh wasting their time. they're just in a void.
49:58
They stepped into a void. into a void.
50:00
And so, I the fact that I got to a place where ultimately I said, "You know what?
50:03
I'm fascinated with festivals.
50:04
I'm on the board of Burning Man."
50:05
And there's no great website for all the world's best festivals.
50:07
Maybe I'll just go around and become the world's most interesting person and go around to festivals all over the world.
50:15
And I did that, 36 festivals in 20 countries in 1 year.
50:16
And um that helped me a great blog post on tim.
50:20
blog about some of your experiences at these festivals. do. I That's right.
50:24
Exactly Yeah, so I loved loved that process, and it did help me move towards next.
50:30
Plus, I wrote another book.
50:31
I wrote a book called Emotional Equations. It did well.
50:32
It became a a New York Times bestseller, and it was another thing that just said, "Listen, like this is my new identity.
50:39
I'm You know, I 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."
50:44
You know, stop, you know, giving me for the fact that I'm no longer a boutique hotelier.
50:53
So, you you mentioned the Emotional Equations. So, I I remember this.
50:54
And could you explain Despair equals Suffering minus Meaning? Yeah.
50:59
When I had that flatline experience, and and to just give I was in St. Louis giving a talk.
51:05
Um I basically probably had an allergic reaction to an antibiotic for my septic leg and my broken ankle.
51:12
And I went to the other side nine times over the course of 90 minutes. you when this happened?
51:17
in I was in Did you make it to the hospital before you flatlined? No.
51:20
So, I was I So, I was I was giving a speech on crutches, which is what First 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?"
51:31
So, I didn't Fortunately, I did not fall over uh at the speaker.
51:35
I was standing up at the at the mic.
51:38
But I sat down signing books, and that's when I slumped in my chair.
51:43
And then they put me I probably didn't have a flatline experience there.
51:46
I just went unconscious for 3 minutes.
51:49
Fortunately, the paramedics showed up a couple minutes later and really quickly and they put me on a gurney and they had put heart monitors on me and that's the first time of nine times that I went flatline and they had to get the paddles out.
52:01
The first time uh they didn't have to use them.
52:04
Uh about 5 seconds later my my heart came again.
52:06
But over the course of the next 90 minutes uh in the ambulance, in the ER, etc.
52:11
And I kept saying, "Okay, this is what I saw on the other side."
52:14
And they whoever was there would take a note of it and turns out it was the same thing over and over again.
52:18
But I long story short Well, hold on.
52:20
Let's not do long story short.
52:22
You can't do long story short on near death experiences.
52:24
What did you see on the other side?
52:27
There is a by the way a festival of the the near a pilgrimage of the near death experience in in Spain.
52:31
Spain has the weirdest festivals in the world.
52:33
Um what I saw was this and it in fact it happened over and again over again means it's pretty remarkable and worthy to just talk about it.
52:43
So, I don't love the mountains. I love the beach. Mountains are okay. I do like it. I love being in nature.
52:50
So, it's interesting this is a mountain setting.
52:51
So, it's a mountain setting, a chalet with a huge um sunroof for uh skylight and light uh is pouring in the skylight, beautiful light um and it's pouring in in such a way that there's actually this viscous oil, very heavy oil on the ground on the most beautiful wood grained uh floor you've ever seen.
53:16
And it's because the of the way the light's coming in and it's hitting the floor, this oil that's sort of slightly moving or it's like going down these stairs, these beautiful wood stairs.
53:26
It's casting this beautiful kaleidoscope of colors uh on the wall.
53:29
And so, what I see is light, I see colors and I see this weird this frangipani scented oil going down these stairs.
53:43
And that's what I kept saying.
53:43
And I never saw anybody else, didn't see anybody on the other side.
53:46
I What I saw myself as observing almost floating above this.
53:50
I felt incredibly peaceful and everything was moving very, very, very slow motion.
53:57
So, um and I you know, I kept coming back to that.
54:01
And I don't really I've never actually sat down with with like a dream analysis or anyone to sort of say what does it mean?
54:06
The fact that it's it's stairs going downstairs means I may be going to hell.
54:08
Um but actually it was up I was up at the mountain chalet way up toward heaven. I don't I don't know.
54:12
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.
54:24
So, yeah, that So, the I was in the you make of that?
54:28
Like I mean and I'm not saying it there there is no whether if you had a Freudian Freudian dream analyst here and they said, "You know what that means? Let me tell you." I'd be like, "Bullshit. Come on."
54:37
Like you can give us your opinion, but It's How would you What would What What did you What do I take from it? Yeah.
54:44
What I What I take from it subjectively?
54:46
take I take from it that I um how I want to honor and experience beauty in my whole life, you know, I do um the gods of efficiency, which I tend to tends to be my religion.
54:58
Um These gods of efficiency have a tendency to force me or or have its way with me in terms of just getting uh very clipped in how I do things because I have to like get all these things done.
55:11
And you know, being clipped in doing things doesn't allow for the time to sort of, you know, have the immediacy of seeing in that moment that beautiful thing.
55:19
So, I think what it's helped me to see is like how do I create beautiful moments in my life?
55:22
Um and how do I take time, you know, to do, you know, fasting day three to three or four days fasting in a row and things like that that allow me to just be in the moment. That's one thing.
55:35
Number two is uh the calmness I felt.
55:38
So, no no fear of like, okay, you know, I'm dying and it's just going to be terrible. There was that.
55:42
But, I think the thing that was most interesting was just the fact that the oil was moving so slowly.
55:47
It's like there's a there's a ketchup commercial anticipation a long time ago, maybe Heinz 57 Ketchup.
55:53
It was like it took so much work to get that damn ketchup out of the bottle. That's how it felt.
55:58
And so, what it felt for me was like I'm slowly moving to my death, but it's a long time from now. Mhm.
56:05
And so, that's what I take from it, which is a positive, you know, overall perspective.
56:08
That night, after having all those experiences, I'm by myself in a in a in a room at the hospital in St. Louis.
56:18
And weirdly enough, in my backpack um that I'd brought with me on this trip was Man's Search for Meaning, Victor Frankl's book.
56:25
And the reason it was there is because I'd gone through a few really rough months.
56:29
And one of my closest friends, who was my insurance agent whose name is Chip, had committed suicide 4 months earlier.
56:37
Um and so, I was trying to make sense of my life.
56:41
And so, here I had this book.
56:41
And as I'm reading this book, I had a hard time sleeping that night. I'm reading this book.
56:46
And I was just distilling, if I were to take the the meaning of that book, Man's Search for Meaning, and turn it into a an equation, it would be despair equals suffering minus meaning.
56:57
And the way I thought of it is suffering is sort of a constant, if you're a Buddhist, and I sort slightly am.
56:59
Um uh if you're you believe that suffering is always ever present.
57:05
It's the first noble truth of Buddhism.
57:09
And yet, meaning or suffering and meaning are actually inter uh they're sort of inversely proportional to each other.
57:15
So, if you do the math of like, okay, suffering uh despair equals suffering minus meaning, 8 equals 10 minus 2.
57:19
If you take 2 and turn it to 4, then 8 becomes 6. Right.
57:27
And so, despair goes down when meaning goes up.
57:29
And this is when I realized that that practice I've had since, you know, being a 23-year-old of writing my what my lessons were for the week was a practice that actually was giving me meaning.
57:42
And that's that equation, which I came up with that night, what I ended up teaching it to all of our leaders in the company as we went into the Great Recession.
57:49
Um, and ultimately I said, "Darn, I went to to Bhutan to study the Gross National Happiness Index because I wanted to see what was the happiness, you know, equation in life?"
57:58
And I ended up giving a TED Talk about that.
58:00
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 um, happiness or or disappointment um, or wisdom.
58:16
Are there any other equations that you find yourself referring to or thinking of more often?
58:24
Yeah, I'd say a couple of I and the anxiety one's very relevant in the business world and that's anxiety equals uncertainty times powerlessness.
58:32
So, it's not a plus, it's it's a times.
58:34
So, the uncertainty and the powerlessness together are combustible.
58:38
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?
58:45
And what is it where you can what how what ways can you actually create some influence and some sense of power?
58:52
And by doing that, you actually help people get to a place where they have a little bit less anxiety.
58:57
Makes it very tangible, right? I mean, it tangible.
58:58
Or disappointment equals expectations minus reality.
58:59
That's a classic one for any business.
59:01
Like, "Okay, what's your customer expectation?
59:06
And then what is it that you're giving as reality?"
59:07
And if the disappointment is more predominant than the reality, then, you know, they're going to there's going to be I'm sorry, if the expectations are high and reality is low, disappointment is what it will come from that.
59:18
So, um, and those both are negative.
59:20
The happiness one that I learned in in Bhutan was happiness equals wanting what you have divided by having what you want.
59:28
Wanting what you have speaks to gratitude.
59:34
Uh having what you want is the process and of gratification.
59:39
So, it's not to say this is not the So, so it says gratitude is better than gratification.
59:43
Well, that's fine if you're a Buddhist.
59:45
That's fine if you don't want to go out and attain attain attain.
59:48
I want to go out and attain and I want to go gratify.
59:50
But but gratification doesn't necessarily bring happiness. It may bring success.
59:54
And for a lot of people who think that success will bring happiness, you know, they go on the hedonic treadmill and end up realizing just when they get the thing that they thought they wanted, there's some new shiny object that becomes the new thing.
1:00:06
The rabbit leading the greyhound around the track just sped up a little bit. that one. Damn. Okay.
1:00:12
We occasionally occasionally we go there.
1:00:16
Well, you know, it's it's you, me, Liz, and a few million people who might be listening to this.
1:00:21
And speaking of Liz, so this ties in very very nicely. Yeah.
1:00:26
Uh so, both you and Liz are very thoughtful and make a point of trying to be aware of your own thought processes, reasons for doing things, the drivers sort of behind the superficial answers that we're all inclined to give that are fast and easy and expedient.
1:00:46
So, so one of her questions uh was, "I noticed that Chip has made a few life changes, selling Joie de Vivre, uh Airbnb, um and now doing what you're doing.
1:01:01
For what looks from the outside like a conscious choice to simplify his life, slow down a bit.
1:01:04
But does he always jump into something else big and sprawling?
1:01:06
I know a lot of people, in parentheses like me I suspect, just can't help themselves.
1:01:12
How do we learn to just be still? Should we? Is that the goal?" Wow. How do you uh Yeah.
1:01:20
How do you how do you begin to think about that?
1:01:23
Um I want to ring her neck. Now I'm kidding.
1:01:28
Um But this is I think something that a lot of people who have become good at achieving struggle with. Oh, totally.
1:01:36
Um you know, I Peter Guber I I got to interview him on stage.
1:01:41
He's one of the Actually, you know Peter Guber?
1:01:44
Yeah, we We actually have both been in his box at the Warriors games.
1:01:48
Um I interviewed him on stage and this guy's 20 years older than me and he's been successful in so many different ways and I was interviewing him on stage at the Airbnb Open, which is our big host open that I was in charge of at 20,000 people in LA at this one.
1:02:01
And so I'm on stage with this guy and listening to him and thinking, "Oh my god, that could be me someday."
1:02:06
And he's an amazing guy, but he's constantly so driven to succeed to succeed at the next thing.
1:02:13
And um so what I took from that and what I take from Liz's question is I think the the real question here is not whether you're going to just be still. I love being still.
1:02:27
I The fact I'm a meditator, the fact that I have chosen to live in Baja California, an hour north of of Cabo San Lucas on the beach learning how to surf and having a very simple life there it means there's been a lot of conscious choice of how I'm curating my life, not living in San Francisco anymore.
1:02:47
And um yeah, I I have these ideas that I feel like I want to go out and try in the world.
1:02:54
But the question is how am I executing on them and what is my intent or what's the sort of the silent intent for why I'm doing it.
1:03:03
And I think for so many of the things I've done in the past, certainly Shvo Vie was at times an exercise in seeing how big Chip's ego could get.
1:03:10
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.
1:03:23
And so my ego was on display.
1:03:25
And um then I joined Airbnb because the the founders asked me to and all of a sudden I'm not you know I was the tiny version of Richard Branson in my company, but now I'm like instead of being the sage on the stage, I'm the guide on the side.
1:03:42
And I'm helping these three uh co-founders take their little tech company and turn it into a global hospitality brand.
1:03:48
And I realized in that process that I'm still driven, I'm still totally in it, although I actually was learning how to not do the 70-hour a week kind of thing.
1:04:00
Not 4 hours a week or whatever.
1:04:00
You you've been able to perfect Whatever that book was. Uh yeah.
1:04:05
So I uh what I was realizing is that actually I'm not doing this for ego purposes.
1:04:09
I actually feel like I'm doing this more for legacy purposes.
1:04:11
I'm doing this to actually help them and I believe in their mission.
1:04:16
The Airbnb mission to belong anywhere, help people belong anywhere.
1:04:20
And turn strangers into friends. All of that was good.
1:04:23
And now this modern Elder Academy that I'm doing in Baja that she's reciting there You know, the reality is yeah, it's it is me being driven again, but I've put guard posts on it.
1:04:32
I'm doing it in Baja, I'm doing one location, I'm not doing multiple locations.
1:04:37
So you you feel comfortable with that commitment.
1:04:40
I feel com- Yeah, no, I am.
1:04:40
Actually and frankly the cancer, you know, for those who you didn't hear earlier on the I've got cancer.
1:04:45
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."
1:04:52
I think the idea of lifelong learning and how do we go to a retreat that helps us to repurpose ourselves, reframe our mindset, to have a growth mindset about you know, our aspirational aging ahead of us.
1:05:07
I think all that's important. No one's done that yet.
1:05:08
There's all There's been all kinds of retreat centers, but not a place that has a curriculum for people in midlife.
1:05:13
When you say midlife, let's put an age range on that.
1:05:16
Well, midlife Or it doesn't have to be age, but how would you How does someone know if they're in midlife as as as They're in crisis. Is it a plot? No.
1:05:26
No, you know, midlife has historically been defined as either 40 to 60 or 45 to 65.
1:05:30
Um the truth is the the the phrase midlife crisis was coined in 1965.
1:05:35
And the reason that didn't exist before then was because longevity in the US was 47 years old in the year 1900, and it became 77 by the year 2000.
1:05:46
We we get We added 30 years of longevity in one one century.
1:05:51
So, what happened is this new era of life sort of got you emerged.
1:05:56
Right, it's not it's not yet fade to black.
1:05:58
It's like, no, you have another Yeah. half the movie to go. Well, you do.
1:06:01
And the the thing that happens in midlife and what how do you know you're in midlife, whatever the age is, is you feel the weight of the accumulation of what you have acquired in your life.
1:06:12
And I don't mean just the physical things.
1:06:13
I mean the friends, the responsibilities, the identities, like the you know, sort of invisible name tags that define who you are in the world.
1:06:22
Um and you actually frankly are sort of feeling overwhelmed by all of that accumulation.
1:06:31
There's this reset that happens in midlife.
1:06:32
And and you could say frankly with the millennial generation, it might happen actually earlier in life. It might happen at 35.
1:06:39
Frankly in Silicon Valley, it absolutely happens in the mid-30s.
1:06:43
When especially if you're an engineer, um where you feel like, wow, I am no longer, you know, I'm no longer perceived as, you know, an up-and-comer.
1:06:52
And in a in an industry that, you know, is like the entertainment industry or fashion. professional sports. Or yeah, exactly.
1:06:57
So, you So, I think personally midlife is from 35 to 75.
1:07:02
And part of the reason I think and I think it used to be just 45 to 65, it's it's happening younger because of the fact that people feel irrelevant earlier in you know the digital intelligence that we desire in companies mean that there's a greater and greater desire to hire the new digital natives.
1:07:19
And 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 the future you know as a longevity we're we're at in the right around 80 right now but by the by the time we get to the end of the century I I think we'll be about a at a hundred for longevity in the US.
1:07:37
That means at age 75 you're probably still working. Yeah.
1:07:40
And at at least you know by choice or by necessity.
1:07:42
You're creating I mean doing something.
1:07:44
So I think that that period of time so midlife used to be a crisis now it's a marathon and that's ultimately what led me to saying you know what we need to figure out this wisdom school.
1:07:51
How do people uh go into midlife and not think of it life as being just a one tank journey like you fuel up with all of your you know education and support up to age 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 you're starting to run on fumes and you need a you need a pit stop.
1:08:13
and you need a you need a pit stop. And so um the Modern Elder Academy is the idea of that pit stop and I think it's going to help to create a new category of academia or even hospitality real estate which is the midlife wisdom school just like Canyon Ranch 40 years ago Mel
1:08:30
Zuckerman overweight accountant from LA wanted to go to a place to get healthy and all the places that he saw 40 years ago were mostly like fat farms and mostly for women and he ended up creating Canyon Ranch in Tucson and it really sort of it basically created a new hospitality real estate category called the destination spa resort. Spas had
1:08:48
Spas had existed for thousands of years but not a category of real estate called destination spa resort.
1:08:55
So I think that's what I'm trying to do so to to answer in the long-winded way uh question when I see something like that and I can see that I can be a social entrepreneur that's actually trying to uh fix a societal ill, which is ageism and people getting stuck in midlife, I'm going to do that.
1:09:15
And in this case, I'm doing it, you know, as a social entrepreneur with a social enterprise where 60% of the people are on scholarship.
1:09:22
So, I'm funding a million dollars a year in in scholarships.
1:09:24
That that is something I want to bet on, but I want to bet on it as a catalyst for others to do their thing.
1:09:32
That's what I was going to ask. Yeah.
1:09:33
So, like Burning Man created a bunch Burning Man created a great idea, and so there's a bunch of 10 principles festivals around the world.
1:09:38
Esalen, great idea 1962, led to, you know, 100 personal growth retreat centers. Got it.
1:09:45
So, the academy is a proof of concept.
1:09:47
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."
1:09:57
I do you think, when you say I can see a bunch of workarounds to the one location limitation.
1:10:02
So, when you say one location, does that mean that you will be only hands-on in one location or do you envision some type of, for lack of a better descriptor, like a franchise model or an association or a loosely uh organized affiliate uh collection of dozens or hundreds of properties that Chip is somehow involved with?
1:10:28
your enterprising mind and I have thought of all of those and I Well, I just want to know when you say like I'm limiting it to one location, does that Is there a Is there a footnote to that? Thank God for cancer. Yeah.
1:10:39
Honestly, I um the path that you're talking about, I was in con- 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, you know, the TED Talk and 6 weeks before the Modern Elder Academy was opening to the public after a 6-month beta period.
1:10:58
So, at that moment, I said, "No."
1:11:04
I said, "And I keep saying, no."
1:11:04
The thing I will do is create sort of he- like the um the startup kit.
1:11:12
Here's how you can create one.
1:11:13
Not a Modern Elder Academy.
1:11:16
We may only have one location in the world, but a midlife wisdom school.
1:11:17
You call it what you want it to be Here's Here's how we can do it.
1:11:22
You know, I don't want to make you know, could be a consulting opportunity, but I don't really care about the money on it.
1:11:28
I'm lucky enough, thank God for the Airbnb the last 6 years of being there, because I don't have to worry about money, that's for sure.
1:11:35
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.
1:11:46
You know, aging is not something that we aspire to.
1:11:48
And And yet, there are a lot of real ple- unexpected pleasures of aging.
1:11:55
The U-curve of happiness is Do you know that? Do you know that?
1:11:57
Oh God, let's talk about this.
1:11:58
So, U-curve of happiness is so fascinating.
1:12:02
It's so at odds with the societal narrative.
1:12:05
I can see where this is going.
1:12:06
So, the U-curve of happiness has been proven in every country but Russia.
1:12:11
Russia Russia, people get happiest after they die.
1:12:15
That's a It's a statistical error, clearly, but there's something to that.
1:12:18
Um Every other country in the world that has been studied, the what they show is the following: from about age 25 to about age 45, uh, 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.
1:12:39
And then, between 45 and 50, there's this what Brené Brown would call the unraveling. Uh, another Texan. She's in Houston. Yeah. Oh, yeah.
1:12:48
She might even be here in Austin now because her her daughter's here. Yeah, exactly.
1:12:52
So, um the great unraveling that happens in midlife where people actually start to discard things and they move from the accumulating mode to the editing mode.
1:13:03
So, that editing mode, the idea that people are moving into that mode is leads people to get to a place where they get happier with each successive decade.
1:13:13
So, people are happier than in their 50s than in their 40s.
1:13:15
They're actually happier in their 60s than their 50s.
1:13:19
And they're happier in their 70s till than their 60s.
1:13:22
Men start to flatten out in their happiness in the second half of their 70s.
1:13:25
Women, it starts happening in their early 80s.
1:13:27
So, in essence, what it's saying because women women's live longer than men is there's a point at which 5 to 10 years before you die, you actually start to maybe get a little bit less happy because there tend there can be, you know, acute uh health issues going on. But, that's fascinating.
1:13:44
The fact that we actually get happier as we get older, that is not what you see on the TV. Yeah, no.
1:13:51
Um and so, I think the idea that or the aging brain, we know the aging brain we have less recall. What's your name again? Oh, that's right, Tim.
1:14:01
The aging brain doesn't have recall or is not as quick as it used to be.
1:14:04
But, what a lot of people don't know about the aging brain is it gets more adept at doing left brain right brain tango, which means basically the brain shrinks a little bit as it ages.
1:14:16
It actually gets it's able to you're able to as you get older move from the linear left brain to the creative right brain much more easily, more adeptly.
1:14:27
And what does that lead to in terms of a positive?
1:14:29
Uh it leads to being able to think more synthetically, holistically, get the gist of something.
1:14:34
So, if you want somebody on your team to actually sort of like hear it all and then distill it down to the wisdom of like what you they just heard, an older person can do that better than a younger person.
1:14:45
A younger person is but much better at doing focused.
1:14:47
So, why is that relevant?
1:14:49
Well, in the you know, let's talk about Airbnb for a moment.
1:14:53
At Airbnb, when I joined 6 years ago, we had I loved the founders and they were doing an amazing job and the company would have been successful without me.
1:15:00
But, when I joined 6 years ago and it was, you know, maybe 1/20th of the company the size today, we had 30 initiative strategic initiatives in the year 2013 when I started.
1:15:11
And nobody in the company, including the founders, could actually recite all of them.
1:15:14
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.
1:15:25
I said, "We got to get down to four."
1:15:30
So, for 2014, we're only going to have four strategic initiatives.
1:15:32
And so, we spent 3 days arm wrestling over that one 23 different potential initiatives that we were going to do.
1:15:38
And it was that kind of distilling down, I think the How did you do that?
1:15:45
Because I think a lot of people listening, maybe even one person sitting here talking, i. e.
1:15:48
myself, uh struggle with long lists of prospective or current projects. Yeah, for sure. Right?
1:15:57
So, here you have a fast-growing, very, very fast, I mean, understatement, growing startup. Yeah.
1:16:02
And you have a list of how many? 20-something? Who knows?
1:16:04
Yeah, 20 23 that we 23 initiatives that the 12 members of the strategic of the leadership team thought should be Okay.
1:16:13
our our potential four for next year.
1:16:15
So, how do you facilitate a process by which you get that down to four?
1:16:20
Well, it's the intellectual jousting.
1:16:21
Because you're also kind of the new guy on the job, right?
1:16:23
guy on the job and I was the old guy on the job.
1:16:25
I was twice the age of the average person in the company.
1:16:29
Um you know, 20 years older than I was 21 to 23 years older than all three founders.
1:16:34
Um but I think what they appreciated was there was an element of I think a modern elder versus a traditional elder is the difference is the modern elder is as curious as they are wise.
1:16:43
And it's that curiosity that opens up possibility, and the wisdom is what distills down the essence of what's important.
1:16:49
And it's that essence of what's important that I think we got to in that those three days in New York, where we sort of said, "Okay, so what is it we want to be when we grow up?
1:16:59
We want to be a place where people can belong anywhere."
1:17:01
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.
1:17:08
We also looked at that, "Could we take the idea of the Airbnb sharing economy to office space or conference facilities or anything that had excess supply?"
1:17:20
Uh there are a lot of natural sharing economy uh businesses that could be created.
1:17:25
Um but we also had to ask ourselves, "What's the dream of what we want this to look like 5 years from now?"
1:17:31
Or maybe even 10 years from now, because Brian really wanted us to look very far into the future.
1:17:37
And maybe that dream could help become an editing function.
1:17:43
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.
1:17:50
When we were trying to figure out, "What's our differentiator versus Marriott or even Kimpton, another boutique hotel company?"
1:17:58
We actually imagined the idea that um we could ask the question, "What business are we in?"
1:18:05
Because the number one Harvard Business School Harvard Business Review uh reprint of all time uh came from uh an article from 1960 called Marketing Myopia by Theodore Levitt.
1:18:17
And then management theorist uh and author Peter Drucker took that idea one step further.
1:18:23
He said the most important question any business leader could ever ask themselves is, "What business are we in?"
1:18:30
Well, back in the my Joie de Vivre era, we took that idea of what business are we in, and we turn it into a little bit of a game.
1:18:36
The idea was uh we would be asking executives or senior leaders to ask themselves that question um in the following manner.
1:18:47
So, one person would sit facing the other.
1:18:49
The person asking the question would say, "What business are we in?"
1:18:52
And the the second person, the person answering would say, "Okay, we're in the boutique hotel business."
1:18:57
The first person would say, "Thank you.
1:18:59
What business are we in?"
1:19:01
And this time this the per- second person, the person answering could not answer the same way twice.
1:19:06
And if you do that five times, it really almost is like an archaeological dig to figure out the essence of your company.
1:19:13
What's your soulful differentiator as an organization?
1:19:17
Um this is how we found out that we were in the identity refreshment business at Joie de Vivre.
1:19:21
And it was this same idea uh that uh we applied to Airbnb uh when it came to uh an offsite retreat we did relatively soon after I joined the company.
1:19:33
We sat our executives in pods of two um so they couldn't hear each other.
1:19:37
Any company could do this.
1:19:41
And we had them go through this exercise of asking the question five times, "What business are you in?"
1:19:46
You can't answer the same way twice.
1:19:49
And the beauty of this is we ultimately got us to a place over the course of that day where we came to the conclusion that belonging anywhere was really the mantra, the definition of what differentiated us versus the Marriotts of the world.
1:20:02
And it was that idea of belonging anywhere that helped us to then imagine how could we edit all of the possibilities of the things we could go into.
1:20:13
Um similarly, any executive or any frankly any person could actually ask this question in a slightly different way for themselves.
1:20:22
The question would be, "What mastery do you offer or what mastery can you offer?"
1:20:27
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 that 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.
1:20:45
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?
1:20:55
Well, I think, you know, the basic premise of the academy is that in midlife if you need to sort of reframe your mindset for what's moving forward.
1:21:03
There's a famous Carl Jung quote about you can't live the afternoon of your life same way you did the morning.
1:21:09
And so speaking to that, we have an exercise around evolution, evolving, because the first lesson in my book Wisdom at Work, Making of a Modern Elder, is to evolve.
1:21:17
And it's the hardest one.
1:21:20
It's Evolve is the first step.
1:21:22
Evolve is the first step.
1:21:22
The second step is to learn.
1:21:23
The third is to collaborate, and the fourth is to counsel.
1:21:27
And we can come back to that if you want in a moment, but evolve.
1:21:31
Wow, what does that mean?
1:21:31
It really means learning to edit what is no longer serving you.
1:21:38
So we do a lot of different exercises around the idea of liminality, which is being in between two things. Right.
1:21:45
So for people who might recognize liminal, subliminal. Right? Subliminal messages.
1:21:51
So a liminal is sort of right there, and it's sort of in between two things.
1:21:54
It's the transition that frankly a caterpillar to a butterfly, the cocoon, is the liminal state.
1:22:00
People don't like to be in a liminal state.
1:22:02
When you're a kid, you're used to it because everything's in between.
1:22:05
You know, going from crawling to walking, you know, going from prepuberty to an adolescent and and teenager.
1:22:14
But when you're an adult, you don't like to be liminal.
1:22:15
And yet we have all these transitions in midlife that actually make us feel liminal.
1:22:21
So we do this exercise where there's a whole um, counterful of name tags, empty name tags.
1:22:29
40 of them actually are empty.
1:22:31
120 we've written different kinds of mindsets, ways of perspective, or ways of identifying yourself that aren't serving you anymore.
1:22:40
Now, if you were to do this on your own, you no one's going to write those for you.
1:22:43
You'll have to write these yourself.
1:22:45
But the process of this was the process of what you can do is you actually write down anything from, you know, my body is falling apart, or I'm I'm uh never going to meet the, you know, love of my life.
1:22:58
So, the they're in part beliefs that are no longer serving you. That's right.
1:23:01
Millennials rule the world.
1:23:03
Uh yeah, there's a variety of different things we have there.
1:23:04
And then people a lot of times use their own uh name tags.
1:23:08
And what we do is the the crescendo of this experience this af- that afternoon is people slap like up to six different name tags on their chest. We go around the room.
1:23:21
The name tags that are already filled out.
1:23:22
As well as the ones they filled out themselves.
1:23:24
So, if they have one that they can't find, then they fill out the empty tag. Exactly.
1:23:27
And so, then you go around the room, and you can do this with with like four friends, and you go around the room silently 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.
1:23:46
And so, as a result of that, um, we end the afternoon with a little fire pit.
1:23:52
We don't walk on, you know, any coals or anything like that.
1:23:56
We just have people write down what's the thing that they're ready to evolve out of that's no longer serving them.
1:24:02
And it could be some of the examples of things are like, you know what?
1:24:06
My sense of my success in in my career will no longer be my sense of success in life.
1:24:15
Um, that's an example of something I'm saying, "Okay, I'm I'm going to put that in the fire and then let it burn."
1:24:21
So, that's an example of a specific kind of exercise we do.
1:24:26
Um we do a lot of mindfulness exercises as well in terms of helping people to calm their nervous system.
1:24:30
Can I pause for 1 second? Yeah.
1:24:31
So, the up to six tags on the chest, do you participate in this exercise with I do.
1:24:37
Would you be willing to share some that you've burned?
1:24:41
Well, one of the ones I Yeah, I mean I since you've heard my health diagnosis, I say like I've recently been given a a scary health diagnosis and I feel a little lost.
1:24:51
So, that would be an example of a name tag.
1:24:53
Another name tag would be um Yeah, I you know, I I think I might never meet the soulmate that I met 6 years ago and no longer in that relationship.
1:25:04
I am in the relationship, but it's it's it's turned into a different kind of relationship.
1:25:07
Um another one could be um or another one that I've written and and then ultimately burned is um it's time to take down the scaffolding of my ego. So, what does that mean?
1:25:20
It means like over the course of my teen years and growing up you build an ego.
1:25:24
We sort of create this container.
1:25:26
And our ego can be a very healthy thing.
1:25:28
It can actually create the separation.
1:25:30
It's the thing that actually helps us to know who we are.
1:25:34
But it is a bit of a scaffolding.
1:25:38
And like what I mean by taking down the scaffolding of the ego is really sort of saying behind that is something that's really amazing. It's a soul. It's a heart.
1:25:47
It's and I'm no longer going to let my ego sort of be the thing that I lead with.
1:25:55
Uh and how and then I you know, come up with a list of things how that show how what are the practices or ways of being that actually uh have to change in order for that to be the case.
1:26:06
So, those are some examples just off the cuff.
1:26:08
I'd I wish I had a list, right now.
1:26:11
Do you have uh 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?
1:26:23
They've got to read the book Wisdom at Work the Making of of Modern Elder and they do two exercises, one which is an identity cleanse where they actually talk to their friends about what parts what parts of their identity work and what parts of their identity don't work so well.
1:26:35
So they actually get some feedback and then and this is before they arrive and then they do a values inventory of like what are the values that are most important and stack ranking them so they try to get clear going into it what are the values.
1:26:46
Now later in the week they often go back to that list and say, "My God, now that I've had some time to think about this, my values list is a little different.
1:26:56
Um and so they ask themselves then how can they how or how we ask them and we we work with them cuz it 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.
1:27:11
So they're sort of accountability partners and and people who can sort of help them say, "Okay, yeah, you said your values, you know, your number one value was this and you know, now it looks like it's not there anymore. What's going on?"
1:27:24
Um so that's part of what happens, too.
1:27:27
What's what would be example values that people might then put in order?
1:27:33
Um an example could I mean some of the most obvious ones are family, religious beliefs, making a difference in the local community or or you know, trying to change the perspective on climate change.
1:27:46
So these are those are some of them.
1:27:50
There's other ones which are just like ways of being which are being feeling free.
1:27:56
So that that's not Some people would say that's not a value, but that's sort of a way of being.
1:28:01
Yeah, could be a way of being priority. Yeah.
1:28:02
So this is that's what they are.
1:28:04
So it's a mixture of I would say values and ways of being and we have like a list of 60 of them and then they come up with their top five and then stack rank those top five and and then over the course of the week we we don't force them to go back to it but there's some exercises we do that allow them to on their own sort of look at see and see how those have changed.
1:28:23
Would you be open to talking about family for a few minutes? Yeah. Okay.
1:28:25
So I would I would love to hear your uh some back story that I don't know and then uh have some questions about uh current current day. Yes.
1:28:34
Uh so you are openly gay? Yes.
1:28:37
When have you been openly gay of kind of from the get-go or when when did that So I was uh become something that was sort of publicly that you felt comfortable publicly discussing? 22 when I came out.
1:28:46
So I was I was and dated women, girls, you know, I I was very actively sexually in my high school um and so but I knew behind the scenes like there was something there.
1:28:59
Uh I grew up with a father who who I love.
1:29:01
He's He Both my parents are still living. They're 81.
1:29:07
But my dad was Steven Senior.
1:29:07
I was Steven Junior, the chip off the old block.
1:29:10
And my dad was a captain in the Marine Reserve.
1:29:13
Hardcore, you know, dude and I was the oldest and the only boy and so I was meant to be like the the mini version of dad.
1:29:23
So the my process of being Eagle Scout like my dad, All-American water polo player at you know, in high school and then playing water polo at Stanford, um student body president, all this stuff was like I was on the path to be just Actually, my dad and I we talked about this recently.
1:29:40
He said, "Chip, all I wanted you to do is be a better version of me."
1:29:43
And that was so interesting to hear that.
1:29:45
I always knew that was the case but I never heard him and so he's 81 years saying he's like, "Dad, I know."
1:29:50
And that like with my mind.
1:29:53
Um so I did everything I could to sort of just be this better version of dad.
1:29:59
And then in I was in a fraternity in at Stanford and that's where it started like messing with my mind being in a fraternity with a bunch of guys who um I had some attraction 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.
1:30:15
I was 22 years old living in New York working for Morgan Stanley, you know, investment banker by day and at night walking into my first gay bar and that's when it was like, you know, like Wizard of Oz Munchkin Land, you know, it went from black and white to Technicolor.
1:30:30
I was like, oh, wow, well, this feels a little This this may be a thing.
1:30:36
Yeah, this may be a thing and and so um but you know, back then, wow, I mean, I came out the summer that Newsweek had, you know, the the cover story about, you know, the gay the gay cancer they called AIDS and so it was a really, really not a easy time to come out.
1:30:52
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 like, you know, hardcore business guy and so when I started my company at 26, you know, people knew I was gay and that's sort of an unusual thing to have sort of a founder CEO of Gallo.
1:31:11
I was I was living in San Francisco in a boutique hotel company so that like that made it a little easier.
1:31:17
And yeah, so I've ever since age 22 pretty much just you know, been you know, an out outwardly gay man and have had two two long relationships and now have a couple of sons with a lesbian couple.
1:31:33
So I wanted to ask you about that now.
1:31:35
So how did how did that come about?
1:31:37
So the women live in Houston.
1:31:38
Laura has been a long time friend of mine and she asked me it was her timing was perfect.
1:31:45
She asked me three weeks before I was selling my company, Shuddle Eve and I was like the mama and the papa of Shuddle Eve.
1:31:52
So I didn't have a co-founder ran it for 24 years knew almost everybody in the company, 3,500 employees.
1:31:59
I had a lot of parent energy that had gone into my company.
1:32:03
And I was wondering like, wow, what's going to happen when I like step away from that?
1:32:09
Uh and 3 weeks before uh I we made it public that I was actually selling, um she approached me.
1:32:15
And I'd been approached before by lesbians who wanted my sperm.
1:32:20
Um that uh you know, but I'd always said no.
1:32:22
And so this time I said yes, and I and so uh the idea was frankly um they're going to be in Houston, I'll be the sperm donor, I don't have any legal rights, financial obligations, and we'll see how it goes in terms of whether the the boys or the kids, boys or girls, will know who their dad is.
1:32:41
So it was that that sort of like, okay, I mean, it's pretty transactional, although, you know, probably a little bit more like, okay, maybe it'll be more than that, but let's see it as we go.
1:32:52
Well, they ended up the two women ended up having two boys.
1:32:56
And um more than anything, I think they the the women who you know, they live in the state of Texas, and so the rules around this sort were tough.
1:33:04
It's it's Texas is a little bit more of a conservative state.
1:33:08
Um and so there was some worry that, okay, well, I'm the I'm the real biological dad, and so can the non-biological mom be a mom?
1:33:14
And long story short is we got to a place where it was beautiful.
1:33:18
They They're They knew that my intentions were not to to like be the full-time dad or to even be in a co-parenting role.
1:33:26
I was there to be the boys' dad when I'm there, and I'm there, you know, a moderate amount, and they come down to Baja a lot. And it's been beautiful.
1:33:35
It's just And you know, it's been a great way to give these boys a lot of love and in essence three parents instead of two.
1:33:42
Number of different follow-up questions.
1:33:44
So the the first is a is reflecting on something you said, which is I'd been asked before and I said no.
1:33:50
So I I had been asked a few years ago by 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.
1:34:06
And I thought very very seriously about it.
1:34:09
And I'd never considered it before, thought very seriously, was going to do it, and then had a friend of mine who has had at that time one young child, now has two, and he said, "Tim, if you do that, you are going to need and want to be involved in some fashion.
1:34:29
Like it's not I know you well enough.
1:34:30
It's not going to sit well with you.
1:34:32
Like you're not going to be able to go hands-free."
1:34:35
And so I decided not to do it.
1:34:37
Uh why did you change your mind?
1:34:38
Like why did why did you say yes in this case and no in previous cases?
1:34:43
this idea that literally I had my I I psychologically analyzed myself and I thought I really have had a lot of parent energy being the mentor and, you know, almost father figure for so many people in the company.
1:34:58
And that was going to change.
1:34:58
Uh and I didn't necessarily understand what kind of gap that would create in my life.
1:35:05
So, the timing was perfect.
1:35:05
So, I understand what your your point of view, and yet I was in a place where there was a part of me that was thirsty for it. Yeah.
1:35:13
Um and because the the women were so self-sufficient about how they wanted to do this, I figured, "Okay, it you know, let's see it."
1:35:21
And I didn't I didn't know whether it was going to turn out as it's turned out, which is I'm much more integrated in the boys' life. How did that come to be?
1:35:30
I think it was partly because they ended up having two boys, and I I think, you know, and the and if they'd had the two girls uh two girls, let's say, I'm not sure if it would have been different.
1:35:36
I mean, I think my thinking is it might have been different.
1:35:40
I think the fact that they're boys, like they want their dad, and they want to go pal around with dad on the beach and things like that, you know, I think there that had some influence, maybe, although we've never talked about that.
1:35:51
Um but more than anything I just, you know, you just start loving, you know, these these kids.
1:35:56
I Now, I had had a foster son.
1:36:00
When I was 28, I became a foster parent to a 13-year-old from the Tenderloin, that that district where my my first hotel is, um, whose whose father's black, mom's white, and, you know, basically and he ended up homeless because his parents were, um, just not very responsible.
1:36:15
And so I had had an experience of being a parent, but it was a really unusual experience.
1:36:22
It was me and my partner, my Israeli partner, who, um, I was with at that time and is one of my best friends now.
1:36:28
And here's this kid who's, uh, darker skinned, moving who's straight at age 13, moving in with two white gay men.
1:36:36
And it's like it was perfect for a sitcom.
1:36:38
It taught me a little bit about parenting in the early days, um, very different experience though.
1:36:43
Uh, so I but I do think that this idea of having younger people who need your tutelage and love, um, helps us get out of our ego.
1:36:53
It is absolutely, you know, there's no day doubt that, you know, it's a Zen practice to actually be with a little child, um, and they take all of your attention. Mhm.
1:37:05
So, but I I I, you know, I think it's been certainly the process of how we define and create family has certainly evolved a lot, uh, in the last three or four decades.
1:37:16
How are you thinking about parenting in the sense that are you are you going instinctive or you have you been have you read books on the subject?
1:37:24
You know, I've I There's a lot There's some blogs that I've seen in the past and I I at the end of the day at the instinctive to me is best, but I but that, you know, you know, between stimulus and response is important because it's really easy to be reactive with a kid who's just acting out and Sure.
1:37:39
Um, it's a little more complicated in my case because I'm not with the boys every day, uh, whereas the the the moms are and so I also don't want to pull rank and sort of do anything that's that suggests their approach to parenting is not my approach.
1:37:54
So, I'm pretty much instinctively trying to work with with with their approach as well.
1:37:59
You know, there's a beautiful Dan Gilbert TED Talk about the fact that we all underestimate how much change is ahead of us at every at frankly at every different era of our life.
1:38:09
Um So, I think I have the idea of embracing liminality and sort of saying, yes, I'm moving to Austin.
1:38:17
Yes, a couple years ago, I'm moving to Baja.
1:38:21
Uh and so when you embrace it and you sort of see it as just the nature of life, it allows for it to allows you for you to see some of the secret beauty in some of the things you're you're you might be resisting.
1:38:35
So, I would say I'm still liminal.
1:38:37
I would say that chapter-wise I I do think my process of moving from being in the trenches helping to run Airbnb for 4 years and then 2 years now as a strategic advisor, huge change in terms of my day-to-day living when I was day-to-day there versus just sort of advising Brian and the founders on on things now.
1:38:56
So, I'd say that was a a healthy change. Um but I don't know.
1:39:03
More than anything, I'm just curious.
1:39:05
I I Peter Drucker taught me that curiosity is the elixir of life and I really believe that and I think that the the thing that makes a modern elder different than a traditional elder is a traditional elder was about being revered. It was about reverence.
1:39:20
You revered your elder you respected your elder.
1:39:24
It's not about reverence anymore. It's about relevance.
1:39:26
And relevance requires um understanding the modern-day world.
1:39:32
Um not just spouting wisdom that sometimes is timeless and age-old, but it's actually knowing how to fit that age-old wisdom into the context of modern-day problems.
1:39:43
And so I think if I can spend the rest of my life being both curious and wise, almost simultaneously, that is the potent alchemy that will make me hopefully a very happy person, but also someone who can actually influence other people in positive ways as well.
1:40:01
Yeah, curious and wise and maybe also un-rushed so you can watch that oil in slow motion. oil. Going down the stairs.
1:40:09
Yeah, yeah, or watch the whales.
1:40:09
You know, nature is such a teacher.
1:40:12
I got to say, I mean, being here in Austin, there's some really beautiful natural parts of Austin and I think anybody who doesn't get romanced by nature on a regular basis is missing that lyrical sense of what life is meant to be. Yeah. Definitely.
1:40:31
So I've just a few rapid-fire questions.
1:40:34
They don't require rapid-fire answers, but I always like to ask at least a handful of these.
1:40:39
So the the the first one, outside of your own books, Mhm.
1:40:43
uh what book or books have you gifted the most to other people and why?
1:40:49
Well, other than Man's Search for Meaning, which is probably my number one gift, uh recently, the last couple years, um there's a book called The 100-Year Life.
1:40:59
100-Year Life, written by a couple Brits and it it sort of says, "Imagine the future where the average person lives to 100.
1:41:07
How is that going to change on a personal and societal basis?"
1:41:09
So really interesting observational book.
1:41:12
Um The Happiness Curve, which we talked about earlier.
1:41:16
Um it's a book the the U curve of happiness is what we call it, but the name of the book is by Jonathan Rauch, is called The Happiness Curve.
1:41:22
That's become a favorite uh to gift.
1:41:24
Um I also love Danny Meyer, the restaurateur. Yeah.
1:41:30
Um and he's got and he's got one of the best books on hospitality ever written, which is called um Setting the Table.
1:41:37
Graham, yeah, so it's so Danny Meyer What's what's the list?
1:41:40
I might be getting as we will certainly have Shake Shack for that.
1:41:45
Yeah, Union Square Hospitality Company.
1:41:47
So he's got everything from Gramercy uh Gramercy, that's what I was looking for cuz a friend of mine used to work on the line there actually, Gramercy Park.
1:41:55
Uh fascinating, fascinating guy. Yeah.
1:41:57
Uh also uh some good uh sort of philosophical food to chew on, right?
1:42:03
I mean In terms of his practical and philosophical in terms of let's say eliminating uh of philosophical, thank you.
1:42:07
Marcus Aurelius' Meditations.
1:42:09
I have given that away to to a number of people. There we go.
1:42:14
Maybe Seneca, there's a Seneca book about um about the short life.
1:42:18
Yeah, on the shortness of life.
1:42:19
On the shortness of life.
1:42:19
Um You know one of the things he says in that book is he says uh he says something about the fact that it's not so much the shortness of life, it's how we waste it. Yeah.
1:42:31
And I think there's something to that in terms of like what um what percentage of your life is being spent wasted.
1:42:35
Also, I love a longevity thing that I've been thinking about lately is like imagine what age you're going to live to.
1:42:42
And uh on the online longevity sites say I'm going to live till I'm 98.
1:42:46
And then ask yourself how much of your adult life, if you start counting at age 18, is still ahead of you.
1:42:53
Uh in fact, for me at age 58, I'm at half time if I live to 98.
1:42:59
And when you start realizing you're only 50% of your way to your adult life, you take up surfing at 56 or 57.
1:43:04
You take up Spanish, which I'm doing now because I live in Mexico part of the time. Better learn Spanish. Me espanyol es muy malo. Um So uh Yeah.
1:43:16
Or you write two-thirds of the books that you are going to write in your life as Peter Drucker after 65. Yeah.
1:43:23
Uh if you could put a a word, a message, a quote, a question, anything non-commercial on a billboard, metaphorically speaking, to get it in front of, you know, billions of people.
1:43:35
Is there anything that comes to mind that you might put on that billboard?
1:43:37
Well, you mentioned Oscar Wilde earlier.
1:43:39
I think one of my favorite quotes of all time is be yourself, everyone else's taken.
1:43:44
Yeah, that's a great one.
1:43:45
So, that would be my Oscar Wilde quote I I would probably slap up there.
1:43:47
Um you know, I don't know.
1:43:50
I think the the thing I probably would Yeah, I'd probably stick with that.
1:43:56
Be yourself, everyone else's taken. Yeah.
1:43:59
Chip, this is so much fun. Yeah.
1:44:01
It's really nice to see you again. great to be here.
1:44:03
And to be the first of many times, not necessarily on this show, but just hanging out.
1:44:07
Oh, yeah, we're we're neighbors. Yeah. At this point.
1:44:08
And people can say hello on Twitter at Chip Conley, Facebook Chip Conley author, LinkedIn Chip Conley SF, and we'll link to all this in the show notes.
1:44:17
So, for people who are watching or listening to this at tim.
1:44:22
blog/podcast, you can find links to all of this.
1:44:24
If you just search for Chip.
1:44:25
Also, you have modernelderacademy. org. Mhm.
1:44:30
That people can check out.
1:44:30
Anything else, parting comments, thoughts, suggestions, anything you'd like to mention before we wrap up?
1:44:39
I think I would just finish by just saying that um the more we fear aging, uh the more we're playing on the playing field of the youth.
1:44:48
And there's nothing wrong with that.
1:44:49
Um but if you um if if your intent is to just stay looking young the rest of your life, you're playing on the wrong playing field.
1:44:57
It's a losing battle at some point.
1:45:02
And what some of us are embarrassed to see people who are continuing to play on that playing field.
1:45:04
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.
1:45:16
And it it's part of the reason why we get happier as we get older. Yeah.
1:45:22
And you mentioned the anxiety equals Let me get this right.
1:45:25
Don't stop Don't Don't Don't tell me.
1:45:27
It's anxiety equals uncertainty times hope. Powerlessness. Powerlessness. Yes.
1:45:34
And uh that ties into Marcus Aurelius really nicely as well because it's uh in a in a sense you know this Stoic philosophical system certainly as practiced by Marcus Aurelius entailed a lot of separating what you can control from what you can't. Yeah.
1:45:48
And the possible from the inevitable.
1:45:52
And uh certainly it's it's hard to think of someone offhand who thought of death and mortality more than Marcus Aurelius.
1:46:00
But but learn to befriend it in a way. Yeah.
1:46:02
And not to to fight something uh that sort of left to become this amorphous source of anxiety can really be paralyzing when as you're doing right now learning to embrace it. And live in the liminal. Embrace the elder. There you go. Own the word.
1:46:22
I'm trying to like bring back bring bring back the word. Elder.
1:46:26
And and separate from elderly which is to me that's the last 10 years of your life.
1:46:32
Well for now modern elder.
1:46:32
Uh Chip thank you so much for the time. Thank you Tim. It's great to be here.
1:46:37
Really fun and to everyone listening and anybody watching thank you for joining us and until next time be well be safe experiment often and uh learn to live in the liminal.
1:46:50
Pick up surfing or Spanish or something else that you've been putting off because it's not too late. Thanks everybody.