Chip Conley - A Maverick Entrepreneur's Journey of Wisdom and Innovation

Full transcript: Chip Conley on London Real

3:31 This is London Real. I am Brian Rose. My guest today is Chip Conley, the American Hotelier and New York Times bestselling author who helped grow Airbnb into the world’s leading hospitality brand. In 2008, you collapsed while giving a speech technically dying nine times on the way to the hospital, which led to you drastically reshaping your life and selling the business you founded at 26 years old. A few years later, you became the head of global hospitality and strategy at Airbnb, tasked with growing the business to more than 1 million hosts in 191 countries.

4:00 Today, you promote the concept of modern elder with your latest book, Wisdom at Work, teaching people how to become indispensable employees in the second half of their working life. Chip, welcome to London Real. Thank you, Brian. You talk fast. I do. Right?

4:14 I love it. I’ve gotten good at this over the years. First of all, how’s London treating you? What’s this place like in comparison to Austin, San Francisco, Baja, Mexico? You know, I love London. In terms of an international city with the level of multiculturalism here, it’s maybe the best in the world in terms of just the variety of people.

4:37 It’s an intellectual place. You have you have deeper, interesting conversations. And I think the Brits are finally lightening up in all kinds of ways. You know, they’re actually learning how to meditate and they have Hampstead Pond where they get naked and jump in the water. I mean, like, listen, it’s actually become a fun place.

4:52 And you were here back in 81 when you were at Stanford. They had like a we had a campus outside of London and I had a one class, one class a week in London. And so back then, London was I think the pubs closed around 10 o’clock at night. It was a pasty white city. Not a lot of great ethnic restaurants like we have today.

5:11 And and frankly, it was a country in decline economically. Yeah, you could really feel it. Right. I think also just after the war and well in the 50s and 60s and 70s, like people don’t realize it was really rebuilding itself. Yeah. I mean, I get here in 97 and I remember bits of that like the pub would close and you can’t get a drink.

5:29 Yeah. Weird things you don’t experience the smoky clubs, too. I mean, I don’t I don’t think you have to smoke outside now. Right. And so it’s the back then I just remember the reeking of cigarette smoke when I would come home from the pub and I didn’t smoke.

5:42 So yeah, there’s a lot of that. Look, there’s a lot to cover here. I think before we jump into all of it, I mean, the dying nine times is a kind of an interesting part, maybe to start. And maybe you can talk to us about, you know, what happened, how that changed your life and brought you to where you are now. Yeah. How did dying teach me how to live? I was 47 years old.

6:02 I was going through a very difficult time, had had one of my best friends whose name is Chip commit suicide. And we were right. August of 2008, we were right in the early stages of the Great Recession. At that point, I’d been running my hotel company, Joie de Vivre, second largest boutique hotelier in the U.S. for 22 years.

6:24 And I broke my ankle playing baseball. I got a bacterial infection in my leg, had a septic leg. So I was on a very strong antibiotic so that I didn’t have my leg amputated. That’s the backstory before the death. I should have been at home in my bed, but I had a book that had come out a year earlier that had become a best seller.

6:44 And I was on the road giving speeches. So on crutches, on antibiotics with a leg that was slightly septic. I was in St. Louis, Missouri in the U.S. And at the end of the speech, on crutches, I sat in my chair like I am right now signing copies of the book.

7:02 And then I just went unconscious. Didn’t die yet. They put me on the ground. Three minutes later, I came to. Paramedic showed up a couple of minutes later. And it was when I was put on the gurney for the first time that my heart stopped.

7:14 And at that point, they had heart monitors. And so they had to shock me back to life. And over the course of the next 90 minutes, my heart just kept stopping. It was ultimately probably an allergic reaction to the antibiotic. But my life had been really dark at that time.

7:30 You know, there’s a lot of evidence now that the low point in many people’s lives is around 45 to 52. There’s a lot of reasons for that. How old are you? 48. Oh, shit. There we go.

7:44 So the low point. And let’s come back to this. But let me just say, for me, I was in a low point for sure. So it was curious that my my life basically came to a close. I saw the other side and I kept seeing the other side because when I would come to each time I would die, I would come to.

8:04 And there was a nurse next to me in the in the emergency room and I kept describing to her what I saw. And each time was the same thing. Long story short is that experience led me that night in my hotel room, my hospital, my hospital room to reading Man’s Search for Meaning by Viktor Frankl. I had it in my backpack, of all things. And I came to this conclusion, like, you know, meaning is, you know, the sustenance in life.

8:29 I came up with an equation, despair equals suffering minus meaning. So if you can increase the meaning, you decrease the despair. And so I decided at that point I needed to sell a company that I thought I was going to be running the rest of my life. I’d grown it from one person to thirty five hundred people. It was a terrible time to be selling the company in the early stages of the Great Recession.

8:50 But I knew I had almost like invisible handcuffs on and I knew that I didn’t want to live that way anymore. So that was, you know, the the shift that I needed to make in midlife for a lot of things to actually change in my life. What were you seeing on the other side of death? Of course. I’ve had a few NDE people in here. Yeah, yeah, yeah.

9:13 And very interesting what they say. Yeah, there’s a there’s even I’m a fascinating I’m fascinated with festivals of all kinds. And like I’m on the board of the Burning Man group, Burning Man Project. And so I’m interested that there’s actually a near death festival in Spain. I’m not going to it yet.

9:29 So on the other side of what I saw when I kept going out was I felt like I was in some Swiss chalet up in the mountains, exquisitely beautiful mountain scene, a big chalet, great, lovely wood floors, a sunroof or a skylight that actually had lots of light coming in. And there were a kaleidoscope of colors on the wall from the light coming in. And there was I was an observer of this. There was this viscous, really heavy oil, frangiopani, tropically scented, going down some beautiful wooden stairs.

10:07 And so all I noticed was the sensory experience of the smell of the tropical, the beautiful colors that I was seeing, the sense that if I were to touch this viscous oil, it would be like having massage oil all over my body. And everything was going slow mo. So it was not a bad scene. There were no other people there. The fact it was going, you know, downstairs meant like I guess it was going to hell now.

10:36 Sounds like a hotelier, Andy. Yeah, it was a little bit of exactly. There’s an aesthetic element to it that felt like, you know, if I could capture this moment of sort of the essence of aesthetic beauty, that’s what it felt like. So it didn’t feel scary. I didn’t see anybody else there.

10:54 And but each time I came to it was the same scene. So I have to say, for whatever reason, that was my experience of the other side. OK. All right. So you sell the business and took two years.

11:09 Yep. Sold it to a guy named John Pritzker, whose father started Hyatt. And now the company is part of Hyatt. And then I didn’t know what was next. For those of you who have seen the movie The Intern, Robert De Niro and Hathaway.

11:23 He has a great quote in that movie where he says, musicians don’t retire. They quit when there’s no more music left inside of them. So it took me a couple of years by the time I sold the company, I was just about 50. And I knew I wanted to share my music with someone, figuratively speaking. I just wasn’t sure who wanted to play music with me.

11:48 And you wanted to do it differently. I know. Yeah, I didn’t want to go start another boutique hotel company. I had been one of the early boutique hoteliers in the United States, along with Ian Schreger and Bill Kimpton. And so I didn’t want to go do the thing I’d done for so long.

12:02 I’d created 52 boutique hotels. But I wasn’t sure what it was that was next. I then started a company called Fest 300 that featured the 300 best festivals in the world. And so I thought maybe my job was to be the world’s leading expert on festivals, going around the world to all kinds of festivals and religious pilgrimages. I went to 36 festivals in 20 countries.

12:22 That was beautiful. But about the time I was starting that, I got a call from Brian Chesky, one of the three millennial co-founders of Airbnb. The company was a really small but fast-growing tech company. And what he said to me is we want to be a global hospitality brand and giant. And no one in the company has any hospitality or travel background, nor has anybody in the company actually ever started a business before.

12:47 You’re an entrepreneur, hospitality entrepreneur. You have a lot of leadership experience. We’d love to have you join us. You would be my in-house mentor, head of global hospitality and strategy. And I said, sure, I’ll do it 15 hours a week.

13:00 But within three weeks, I realized this was 15 hours a day. And I had to dive deep into being full-time. And I did four years of full-time work helping them steer the rocket ship. And now two and a half years of being a strategic advisor. Okay. And how early was that for Airbnb?

13:16 Because they were Y Combinator, right? They’re Y Combinator after Y Combinator. But back then, we’re about 1-20th the size or 1-25th the size of what we are today. So a tiny relative. Like 100 employees or not even?

13:28 No, they’re actually about 250 to 300 employees. So I can’t tell you how many employees we have now, because we’re in IPO period at some point in the future. But we’re dramatically larger than that now. We were a global company, and we did have some offices around the world. But we hadn’t become what was called a global network effects business yet.

13:47 At that point, we had a lot of growth to do. Okay. All right. So you get that call. Wow. What a fascinating call.

13:52 Would you come and kind of mentor us? First of all, I said, look, what’s Airbnb? Really? I said, are you a subsidiary of Couchsurfing? I didn’t know much about Airbnb.

14:03 I was this guy who had been a pioneer in the hospitality space as a boutique hotelier at age 26. But at age 50, I was now with the establishment, and I hadn’t really seen the next wave coming. Okay. Didn’t really understand home sharing. Had never heard of the sharing economy.

14:20 Did not have an Uber or Lyft app on my phone. So I was, in some ways, a bit of a laggard to the table. So I had to immediately sort of immerse myself and say, does this business plan make sense? What can I add here? And what’s the strategy?

14:38 If I’m in charge of strategy, what’s the strategy that’s going to take us to become potentially a global brand and one that people are aware of? And I decided to jump in, but I thought initially what they really needed since I was almost twice the age of the average employee there and 21 years older than Brian, who I was mentoring as the CEO but who was also my boss, I thought it was like I had the wisdom I was going to share with them or the knowledge. And what became clear the first week was like, whoa, Chip, you’ve never been in a tech company before.

15:11 I had no clue what they were talking about. And so I realized very quickly that I was as much the intern as I was the mentor. So I was sort of like a mentor and an intern at the same time because I really had to learn the tech industry and what product meant and et cetera really quickly. Okay. This is really interesting what you’re talking about because there’s a lot of people that are watching us, listening to us right now.

15:35 They’re maybe in their 40s or 50s or maybe even in their 30s and they feel like they’re too old, they don’t understand it and maybe they feel, correctly or not, that they’re being tuned out by all the young kids at work. Yeah. And I mean, you must have felt that when you walked in there and some of that’s real and maybe some of that’s not. But what did you learn? Well, let’s start by saying the faster the world changes, the more obsolescence accelerates.

16:02 And so the knowledge you got, the knowledge we learned in college by the time we were 30 might not have been as relevant. And so that’s increasingly true. And so the age at which someone starts to feel potentially irrelevant actually is declining. One of the interesting ironies of the world is we’re all living older but power is moving younger. So there’s what I call the irrelevancy gap that actually has been created that I think is 20 years long or so.

16:32 Because if you’re going to live 10 years longer and power is moving 10 years younger, in your 40s or your 50s you could actually feel like I’m going through this irrelevant scap that is painful. So what did I learn in that process that I’ve been sharing with my book in other ways? Number one is I think a modern elder, they started calling me the modern elder. They called you that? They did.

16:56 And you were okay with that? I was initially really painful because I thought elderly. So elder and elderly are two different things. Elderly is maybe the last five or ten years of your life. Generally you’re in a position where you are in need of support.

17:09 Elder is a relative term. You could be an elder at age 40 if you’re surrounded by 20 year olds. So elder really speaks to the idea of the cohort or social group or community that you’re in. And wisdom. There’s always that in it.

17:25 There’s the wisdom that may come with the age. You could have a seven year old who’s not considered an elder. That’s right. I think wisdom and age are not always correlated. So you can cultivate and harvest it and I think the people who do as they get older absolutely get wiser.

17:40 One of the benefits of being older and helping to get wiser is you have pattern recognition of being on earth longer and you’ve actually stubbed your toe or skinned your knee enough times. You’ve learned from it. And this is one of the benefits today of how do you create a workplace where especially where young tech companies want to go out and disrupt the world and they’ve got really brilliant technology and a lot of great ideas and a lot of risk taking. But they also don’t necessarily understand the industry they’re going to disrupt nor do they actually have sometimes the emotional wisdom or emotional intelligence or the leadership skills.

18:17 And so part of what I think we can do today is say, yes, brilliant young technologist and modern elder marry them together and together you’re better. But let me define what I thought of there was Uber. And like I don’t know. Travis might still have his job. Right.

18:32 They might want him back. I mean, so Uber obviously massive growth. They threw Travis out because of company culture and the way he was talking about and they’re like, the new guy and everything is going to be different. And even part of me was like, hmm, how can you change your company culture? Maybe you can never change a company culture.

18:48 And now people are saying with the latest earnings that maybe there are some culture things. Is this a place where maybe an elder might have been helpful? Yeah, I mean, I think, listen, I’ve only met Travis a couple of times and I think what Travis could have used was probably some sort of cognitive diversity on his leadership team. It was pretty much a bunch of guys almost all the same age. And they probably thought a little bit too much alike.

19:13 And so I think what is true of diversity on any team, whether it’s gender or race or sexual orientation or age, is diversity helps create a little bit of friction and a different way of thinking. So I think they could have used that. I actually don’t think Uber’s problem at this point is purely a cultural one. It may be a business model one. And that’s actually painful.

19:38 I actually think Uber is so popular with those who use it is a good sign because it means, like, okay, it’s probably a pricing issue at some point. And do you think that people are going to go back to using taxis who’ve gotten used to Uber? Maybe not. So I think there’s an ability over time for them to price. But there’s also probably a way that they’re spending money that just needs to be altered.

19:59 But that’s too much in the weeds for that. You can tell I’m an entrepreneur. I like to diagnose companies. So back to kind of elders in the company culture. So I think what is interesting is, so an elder, a modern elder, so the elder of the past was revered.

20:17 That elder doesn’t exist so much anymore, that sort of way of thinking of elders. So reverence. But I think a modern elder is about relevance. So you go from reverence to relevance. Relevance means the following.

20:30 It means that you’ve actually somehow harnessed some wisdom you have, but you actually can give context for it because you can take your timeless wisdom and apply it to modern day problems. The way you understand modern day problems is you actually are curious. You’re as curious as you are wise. The curiosity for me at Airbnb meant I had to learn a whole new industry. I had to learn tech.

20:53 I had to learn millennial travel habits around why would they want to be in home sharing as opposed to hotels, cultural habits, et cetera. In order for me to apply my wisdom, I guess, if you want to call it that, I needed to understand the context. And a lot of people who are older don’t do that. They just think, okay, my job is to dispense wisdom, but they’re not dispensing wisdom. They’re just dispensing their story.

21:16 They’re actually basically dispensing their history without actually trying to give it some context. When you actually can be curious so that you open up possibilities, often with questions, I think the best and most wise people are not full of answers. They’re full of really insightful and catalytic questions. So if you can actually be curious to open up possibility and then wise to distill down what’s essential, that combination of curiosity and wisdom in one person is exceptionally powerful.

21:47 And that’s why a modern elder can be really helpful in a workplace, generally full of younger people. And I think as power moves to those who have digital intelligence or what I call DQ, one of the things I learned from Brian back and forth, we had a sort of a mutual mentorship relationship. I learned a lot of DQ, digital intelligence from him. And I believe he learned from some EQ, some emotional intelligence from me because that is a quality that a person actually gets better at as they age.

22:18 Okay, it sounds like if you want to be this type of elder, and let’s be honest, anybody listening will be an elder one day. Yeah, if you’re lucky. If you’re lucky, right. And if you want to be relevant, and I think everyone does, and useful and still contribute, which I think people wanted, then you’re going to need to know this. It sounds like you have to be really self-aware, as in being able to check your ego at the door, being able to really think, how can I be of value?

22:41 Because the typical thing is, is you come in and say, you kids don’t get it. This isn’t how businesses are run. You’re running around like this, back in my… You need some more gray hairs. Back in my day.

22:51 I’ll be the adult supervision in the room. How dismissive do you want to be? Most older people in the context of younger people take almost the role of the parent or the preacher. And most younger people don’t want to be preached at, and they aren’t looking for that. What they are looking for is wisdom.

23:11 75% of millennials would like to have a mentor, and only 2% to 3% actually have one. So right there speaks to this gap of what people want as younger people and what we’re actually giving them. A mentor, to my mind, is best suited to be a mutual mentor. The mentor of the past was all the wisdom flowed from old to young. Then there were reverse mentors that Jack Welsh at GE said, okay, my senior executive team at GE doesn’t understand tech or computers or internet, so the younger people in GE taught that.

23:40 So that’s called reverse mentorship. The future of mentorship, and I think the future of learning and development in companies is going to be based upon how do you create mutual mentorship, often across generations. And with five generations in the workplace for the first time, we’ve got to figure out how do we create a matching technology for people who can actually teach each other things. So that means you better check your ego at the door. I’d run my own company, grown it from one to 3,500 people over the course of 24 years.

24:09 Now I’m reporting to someone 21 years younger than me. Yes, I’m mentoring them as well, but yeah, I’m a senior executive in the company who has to report to him and his two co-founders. And what I learned quickly was I was no longer the sage on the stage, I was the guide on the side. And so I needed to realize it didn’t all revolve around me. I think the primary operating system for the first half of our adulthood is often the ego.

24:37 It can serve us well in certain cases, and it also can, you know, there’s maybe a little too much of it at times, especially if you’re a senior leader, especially if you’re an entrepreneur, especially if you’ve gotten a lot of attention. So I had a certain amount of ego, that’s for sure. I joined this place and all of a sudden I realized, my God, I am not on center stage. My job is to sort of support these guys and help them be as successful as possible.

25:03 So my primary operating system had to move from, you know, basically the ego to my heart and soul. And that meant I had to frankly learn how to be less interesting and more interested, which was a way of saying, being interested means, my focus was on helping you be as successful as possible. And you said that really quickly, and you mentioned this in the book, but this is a good point just to reiterate, to be, you said a lot of times, sometimes the first half of your life, you’re focused on being interesting, like kind of, look at me, look what I can do, and then maybe the second half, it should be focused on being interested.

25:38 Yes. And it’s something people should think about. So, you know, it’s a very simple thought, which is, the way I look at our lives, I really look at life stages now, it’s been sort of the era of where I am in my life, and we’ll talk more about that in a few minutes. But our bookends of ego are adolescence to what is now called middle essence. Adolescence we’re well aware of, it’s 115 years old as an idea, weirdly.

26:08 You think adolescence, we’ve always had adolescence. Yes, we’ve always had puberty, but we didn’t have the word adolescence until 115 years ago, when a psychologist actually coined it and said, you know what, in London and in New York and these places, at puberty we sort of think that somehow these kids are now adults. So we send them into factories, we get them married, they have babies at age 16, but instead what they said, adolescence is a period of time when you’re preparing for learning how to become an adult, which is why junior high schools and high schools in the US started to actually become more popular, because there was a sense that you’re not ready to be an adult yet.

26:45 And so that’s frankly when you ramp up the ego a little bit too, because the process of actually building a healthy ego is learning how to individuate from your parents. That’s why my 13-year-old stepdaughter tells me to do one. Exactly. Around that age. Her ego is on fire, and we take that ego and we sort of have it in our life for the next 30 to 40 years as a primary operating system.

27:08 When you get to middle essence, which is a relatively new word, and it’s a word that speaks to the idea that, yes, adolescence is full of emotional and hormonal changes and a time where people are going through transition, middle essence is midlife in its pure form. You’re also going through emotional and hormonal changes, a lot of transitions, and in many ways you’re shifting from that primary operating system of the ego to the harder soul. And that is the process of learning, frankly, how to be in a place where you’re very interested in helping other people, because you’re sort of in the process of moving from being focused on success to your legacy or significance.

27:50 And so that is, I think for me, I had no idea when I joined Airbnb that it was going to become a worldwide phenomena and a huge successful company. I didn’t join at that time. I joined at a time where, yes, it had been a wine combinator. Yes, it actually had a global footprint, but was still relatively early. The hotel industry as a whole absolutely dismissed it.

28:16 There’s a great Gandhi quote back in the 1930s about the Brits, and he said about, basically, if you’re a disruptor, first they ignore you, then they ridicule you, then they fight you, and then you win. And that’s what happened in India. And that’s, in some ways, what happens with disruptors. At first, the hotel industry thought I was a nut to actually ever join this company. Then the hotel industry started getting threatened and started fighting us and ridiculing us, fighting us.

28:48 And then, frankly, now Marriott has a whole home-sharing division. Accor owns One Fine Stay, a home-sharing company. Hyatt has had investments in home-sharing companies. And I saw it with boutique hotels as well. Boutique hotels, frankly, was ridiculed until ultimately Starwood created W and IHG based here in London owns Kimpton, the largest boutique hotel company in the world.

29:12 So generally speaking, the pioneers come from outside the industry. The industry doesn’t know what to do with them. Earlier you’re given a chance to disrupt your own industry twice, which I did once as a leader, and then second time joining the next set of disruptors. Mentorship. I want to talk about that right now because everyone asks me about mentorship.

29:33 It’s something that all of the young kids want. And like you said, 75%. And the old kids too. Yeah, right. Both ways.

29:41 Well, yeah, and I have a whole story on London Real with a guest that came on the show about five years ago and it’s a man who, it’s his birthday tomorrow, he’s 74 and his name is Dan Pena. He calls himself the $50 billion man. He has a castle in Scotland. He acts like a James Bond villain. It’s a long story, but he’s a high performance coach, ex-oil man, ex-military guy, American.

29:59 And he has become my mentor really and everyone’s kind of watched our relationship grow. And it’s interesting because we actually, it isn’t the classic mentor relationship. Like I bring something to the table and I kind of teach him about new media and I have him on the show and I do this kind of things and they’re pushing me constantly. And everyone loves watching our relationship. It’s like we’re the ultimate synergy.

30:20 When you put the two of us together, everybody likes watching it because they see this like older man dynamic and he’s constantly saying, Brian, you know you can be more. You’re just scratching the surface. Yeah. You know, you’re doing, he’s constantly in my face and everyone watches this dynamic and they love it because I think they see that they need something like this in their life. He sounds like not just a mentor but a tormentor.

30:40 Yeah, he loves it. In terms of like, you know. Oh, he is. There’s all kinds of styles. Yeah, there is.

30:45 And it’s amazing but everybody wants that and everyone’s always asking me, Brian, how do I find a mentor? So there’s a need for this. And both ways there’s a need. And I’m a big part of Dan’s life as well, you know. He needs that.

30:56 He’s dedicated his life to mentoring younger people as well. So it’s this weird dynamic that almost takes us back to the tribe, to the hunter-gatherers and this weird second stage of life is almost like now it’s time to give back for the survival of your species, kind of. And to continue to learn. Right. You know, when you are in a constant, you know, there’s a growing number of people who are concerned in midlife and later about ageism.

31:19 And they should be because it’s like the last socially acceptable bias in the world. It’s real, right? It’s totally real in the workplace. Oh, and the Bay Area, it’s terrible if you’re in tech and you’re in your 40s or 50s or 60s. But the thing that an executive recruiter said to me recently that was really true that brings me to the mentor idea is she said, you know, yes, there is ageism.

31:41 And yes, LinkedIn, your profile, if they look at your, you know, when you graduate from college, they can figure out how old you are. But the thing is, what she said is once you’re actually, if you can get a foot in the door, that’s a big if, but when if and when you get the foot in the door, if you show a passionately engaged and curious, what people feel is your energy. And if they see and feel your energy, somehow your wrinkles start to disappear. And so what does that mean?

32:09 Well, I think being passionately engaged and curious in the context of a mentor relationship, whether you are the older or the younger one, means that you’re there to actually constantly learn. If you’re the mentor thinking you’re going to be teaching all the time, you’re probably not listening for clues of things that you can learn. And if you’re just constantly teaching the same thing that you’ve always known, you’re not actually renewing yourself. So Satchel Paige, famous pitcher in the major leagues in baseball, famous story, 42 years old, he was called up to the major leagues from the Negro League back in the 1940s.

32:53 The owner of the baseball team, the Cleveland Indians, actually took him down to Mobile, Alabama because Satchel Paige had no idea how old he was. So it turns out he was 42 years old and he was starting in Major League Baseball at 42, at an age where most Major League players had actually retired. He ended up playing Slides 59. Famously, he asked the question, what age would you be if you didn’t know how old you were? And so this element of knowing how old you are, yes, there’s an important element to be able to harvest and cultivate wisdom, or cultivate and harvest wisdom.

33:27 But the premise of being curious with someone younger than you and being empathetically curious, not like curious like an inquisitor, like a lawyer or a barrister. No, empathetically curious means you’re catalytic. You open up possibility with your questions. That’s important. So I would say to a younger person who’s saying, I would like to find a wiser, older person, find a wiser, older person who’s also curious because you may be able to teach them something as well.

33:58 And in the long run, the best relationships when it comes to mentorship are mutual because it actually lasts longer. And one other thought, can I say one other thought? Yeah, this is all good stuff. One other thought is the question that a mentor needs to ask themselves. I get asked, when you write a book that has mentorship built into it and Brian Chesky, moderately famous CEO, young CEO, and I have five other young CEOs I know, a mentor, which we can talk about too, I get asked a lot.

34:27 What I need to look at, and I’m not, for anybody who’s looking, and you have to find a mentor, I can’t do that right now. But what I will say is this, as a mentor, the question I like to ask myself is this, what is it that would serve this person? This mentee’s looking for something. Are they looking for a knowledge transfer? So someone who’s coming to me and saying, I want to understand the boutique hotel business.

34:49 That’s a knowledge transfer relationship. So the mentorship relationship is probably finite. The way the conversation goes is often, they’re asking me a question, I’m answering it with knowledge. That’s one kind of mentorship relationship. That kind of relationship can happen relatively briefly, and it’s an easier one for me to say yes to.

35:11 Then there’s the development awareness kind of relationship. So knowledge transfer, development awareness. My role is to help you become more aware of who you are and at what skills you have, often around emotional intelligence and leadership. That relationship is exactly the opposite. Instead of that person, the mentee asking me questions and I transfer knowledge, actually the relationship is often me asking them questions, helping them see what they have within themselves.

35:42 And my questions help actually maybe illuminate who they are. That kind of relationship is really beautiful. I mean, there’s no doubt that’s the kind of relationship I’ve had with Brian. Initially, it was a knowledge transfer. It quickly turned into development awareness.

35:58 But that’s one that you can only have so many of those, because those take a lot more time. You’re capped at five right now. I capped at six, including Brian. One of the reasons I’m in London is I have for about nine, ten months now been the mentor and a strategic advisor to a company called The Collective, which is a co-living company, poised to become the world’s largest co-living developer and operator. So co-living is basically a form of housing, but some co-working components to it.

36:29 And it’s the idea of smaller individual units and social and communal spaces that where people, it helps people to actually afford to live in a big city. What I loved about Reza Merchant, who was 29 when I first started working with him, he’s 30 now, is this was a guy who had the curiosity and wisdom in him. I knew I was going to learn something from him. So I came at it and sort of said, wow, this guy is really wise for his age. He started his company at age 21.

37:00 By age 29, he built a major company. They’ve got 20 different co-living buildings, very large buildings opening around Europe and the U.S. over the next three years. So I knew I was going to learn something from him. But initially, there was a knowledge transfer piece that I think he wanted, which is like, tell me how to lead, help us to infuse hospitality into co-living.

37:24 But quickly what became clear is some of what he really needed was not the knowledge, but it was the wisdom. And Peter Drucker, quite famously management theorist, 60 years ago in 1959, coined the term knowledge worker. And it was a great term because, frankly, back then a knowledge worker, knowledge was in these huge mainframe computers. And the idea of how do you harness technology to create effective workplaces and companies was a new thought. Today, 60 years later, I think we need to retire the idea of knowledge workers and actually start elevating the idea of wisdom workers.

38:03 Because in the era of artificial intelligence, knowledge is in my pocket. You know, Google gives me everything I need to know. But what scares is wisdom. And that’s the piece that I think we need to help people learn. How do you harvest wisdom?

38:18 Often it speaks to wisdom is about understanding intuition, the pattern recognition about yourself. You talked about self-awareness earlier, but also understanding other people, how to walk into a room and be able to read a room that you’re going to leave a meeting in within, you know, two seconds. So those are things that actually are not necessarily innate. You learn them over time. Right.

38:43 Silicon Valley has a great history of reaching out for mentors. From what I see, we got Zuckerberg reached out to Sheryl Sandberg, the original Google founders reached out to Eric Schmidt. Eric Schmidt has written a book, The Trillion Dollar Coach, about Bill, I forgot his name. Campbell. Campbell, legendary, great legendary mentor that I had heard about in little bits before the book.

39:03 He was the guy that advised Steve Jobs and advised Zuckerberg as well and was just known as everything you’re talking about. I wrote about him in chapter two of my book. Right. He’s like that elder who could, everyone said amazing things about him. He didn’t really have the CV that would think he would be this guy.

39:19 He was a college football coach at Columbia. And frankly, a losing one. Right, yeah, yeah, yeah. This football team didn’t win. But what he had and what you read when you, you know, he and I never connected.

39:34 We actually tried to connect by phone a couple times before he passed away. What you read about him is that he was a phenomenal human and he could read people well. He understood motivations and inspirations in people. He also understood when to amp up the coach, the football coach, who really needed to press someone. Sort of like, yeah, what’s the name of your…

39:57 Pain, yeah. Yeah, so like, but he also knew when to actually give someone a hug. And that I think is a really critical part. If you are Johnny OneNote, so to speak, in terms of there’s one way to actually motivate, you’re not actually looking at context or what is actually needed right now. And so I think there’s times when you actually need to show a little love, and then there’s other times when you’ve got to give tough love.

40:21 And that tough love can be painful to give and for someone to receive, but it’s exactly what they needed to hear. Yeah, no, it’s interesting and it’s just interesting how the Valley kind of seems to do that more. Maybe I’m just seeing survivorship, but you know. I think it speaks to this idea that the Valley is known for technology. Generally speaking, the people who create and imagine new technologies are younger people who are digital natives because they grew up with it.

40:48 You and I grew up with TV. How has it served your career? Not so much for me. And yet if you grew up with computers at an early age, you are a facility. Your fluency is greater.

41:00 So new technologies don’t just come from younger people. There’s all kinds of entrepreneurs who are older. But that technology fluency is strong amongst the young. So a lot of these great ideas come from that. But that doesn’t necessarily mean that Mark Zuckerberg knows how to actually run his company.

41:16 And actually it was Steve Jobs, who was actually his initial mentor. And ultimately, Sheryl Sandberg became that as his COO. Wow. As someone now, me, I’m 48, or other people that are kind of see this coming up in their life. Okay, I’m coming to this weird age.

41:33 What are some of the things that maybe we should be proactive in doing or recognize about ourself, including potential depression or the suicide rate goes up, or ways that maybe we reinvent ourself or rethink it, or put a perspective on this whole part of our lives? Well, let’s go back to talking about the new curve of happiness and why 40 from 45 to 52 is a low point generally. It’s for a few reasons. Number one is there’s the accumulation of so much. So the first half of your life is about accumulating.

42:02 You accumulate relationships romantically and otherwise. You maybe accumulate kids. You accumulate responsibilities. You accumulate jobs and a resume. You accumulate community responsibilities.

42:14 You accumulate stuff materially. So by midlife, you’ve been in the accumulation mode. And then you’re almost weighed down with so many identities and wearing so many uniforms and so many almost mindsets that you’re sort of worn out. And frankly, there’s very little space in your life. And so what happens is people are sort of like, you know, what the hell did they sign up for here?

42:40 And so while it’s been called midlife crisis, Brené Brown, a famous social psychologist, has called it the midlife unraveling. I call it the midlife edit, because I think the first half of your life is about accumulation and the second half is about editing. So if you really start to realize as you move into your 40s, here’s the good news with millennials, is millennials are better at editing earlier. So we’ve sort of grown up, I’ve grown up with the three-stage life.

43:09 You learn until you’re 20 or 25. You earn until you’re 65. You retire until you die. That model is gone, but it was the model that I grew up with. And so the good news with millennials is they sort of have like done their editing along the way.

43:23 So they may not have as much of a crisis. But for a lot of people, it’s their 40s when they actually have to ask the serious question, you know, that’s defined by the equation, disappointment equals expectations minus reality. Where are my expectations of where I was and where’s reality and where’s the disappointment? Because the 40s are where a lot of disappointment sort of rests on people’s laps. So you start to actually say, what am I needing to edit?

43:49 You did this eight years ago, saying, I don’t want to be a banker anymore. That’s not the life I want. You were ahead of the game in the sense that you did it at age 40. A lot of people take it, they have to get to their 40s. This is when divorce happens a lot.

44:02 This is when a lot of things change. People need to sort of have enough awareness along the way. It’s helpful to be aware along the way. Are you on the right path? Because if you wake up one day and feel like, damn, I’m climbing the wrong mountain to sort of use David Brooks’ second mountain analogy, then, you know, you get frustrated if you feel like I’ve wasted some time here.

44:26 So asking questions and having the self-awareness about, like, am I living my life the way I want to is really important. But a second piece is to really start to realize, what is it that I need to edit out of my life? What is no longer serving me? We have an exercise at the Modern Elder Academy, which I’ll talk about that in a little bit, where we actually have people wear name tags. Like, the very first 24 hours of there, there’s an exercise where they go to a table and there’s a bunch of mindsets and ways of thinking and identities on the table that could be anything from my best years are behind me to I don’t want to try something new to I feel invisible to I feel lonely.

45:10 And people put them on themselves. Or, you know, a good one is, I’m responsible for everybody around me. And people wear these up to six of them and then we just go around silently and stare at each other and then look at these and then stare at each other again, give each other a hug and then move on. And then over the course of that time, by the end of that afternoon, we say, which of these mindsets or identities are no longer serving you? And we have everybody on their own private piece of paper write down what it is in their life that is no longer serving them that they need to edit or evolve out of.

45:47 And that afternoon, we go to the fire pit and one at a time, privately, each person takes their piece of paper and throws it in the fire pit while at sundown, right at sunset. And it’s a ritual that helps you to understand, yes, you don’t live the afternoon of your life the way you live the morning. Carl Jung’s paraphrase there that the fact that yes, midlife and later is different. And if you want to play on the playing field of your body and your looks the rest of your life, you can and there’s beautiful YouTube videos about people at age 92, you know, running a marathon.

46:24 I love it. But if you spend the rest of your life thinking that everything is about your body and your looks, you will miss out on this great, beautiful opportunity of when the happiness starts to come up again in the second half of life. When you actually start to realize the things you leave behind may not have served you and there are new things you can focus on. And generally speaking, the playing field of your second half of your life is not your body and your looks, it’s your heart and your soul.

46:51 And once you move to that place miraculously, you feel less weighted down and ready to start to evolve into a new kind of person. And people say, I want what that guy has or that person has or that woman has. Do most people get there on the happiness or do you have to make concerted choices and edit? Or will things get edited out for you whether you like it or not? There you go.

47:16 It’s not like everybody is so self-aware and everybody goes to workshops and they go to the Modern Hilder Academy and it all gets better. No, by circumstance and often by tribulation or just awful things, people have to change their expectations. And it’s in their 40s and 50s when people often downgrade their expectations and downgrade the way they’re looking at their life and that’s how they actually cope. Unfortunately for some people, that means they just narrow their focus.

47:53 There’s Carol Dweck from Stanford. A psychologist has a theory about mindset, growth mindset versus fixed mindset. What she basically says is that you can either be in a fixed mindset which means that you’re trying to prove yourself. And so you tend to do things that you know you’re going to win or you know you’re going to succeed at because basically success is defined as winning. So that’s how many of us live because you want to actually feel like you’re competent and successful at something.

48:23 As you get older, especially if you’re playing on the same old playing field, the number of things you think you’re going to be good at and you can prove yourself at actually starts to narrow and then your life narrows. She also says there’s the growth mindset and a growth mindset is not about proving yourself, it’s about improving yourself. So the definition of success is not winning, it’s learning. And so I’m 58, I’m learning how to surf. I’m not very good at it but I’m trying.

48:52 I’m learning Spanish. I live in Mexico half the time. I better learn Spanish. One of the great questions any of us can ask ourselves and I rarely say this to people so I’m really glad I’m saying it now because I think it’s so beautiful at any age. Ask yourself 10 years from now.

49:09 For you, you’d be my age. For me, I’d be 68. What is it 10 years from now that you would regret if you didn’t learn it now? What’s something you really need to know 10 years from now that you could start learning now? This is a way to get curious about what is it that’s going to serve me in the future.

49:31 It also goes toward that growth mindset of saying I don’t want my life to get more and more narrow over time because when your life gets more and more narrow, you get less curious and you get less interesting. There’s a great line in the movie Any Given Sunday where Al Pacino says, when you get old, things get taken away from you. It just came to my mind. He says it. It’s true.

49:56 If you don’t change your mindset, things will get taken away from you and you become this one trick pony maybe then to no tricks. There’s something to be said for that in terms of if the edit was by choice but if the edit is by necessity and society sort of took it away from you, that doesn’t feel good. You actually then go into this downward spiral. We all know people who don’t fit the U curve of happiness. They’re 70 years old and they’re cranky and they’ve sort of given up.

50:24 There’s lots of people who fit that profile but if you want to look, do the Google search for U curve of happiness, read Jonathan Rauch’s book called The Happiness Curve and you’ll see like, yeah, this is across all cultures except for Russia. Russia people are happiest after they die. It’s a statistical anomaly but it’s sort of weird but like, yes, there’s a weird thing that people actually tend to get happier at the latest stage of their life, you know, right before they die.

50:50 Why is that? I don’t really. You’ve been there? I don’t know. I don’t know.

50:55 They die young too. Yeah, I haven’t been involved. I haven’t been involved. I haven’t been in Moscow. I haven’t been in Russia since 1981.

51:01 Okay, so this U curve exists across all cultures and it’s kind of like understanding it, knowing it’s going to happen to you and start being proactive in this. Think about the editing now, thinking about this growth mindset and it really is life and death. Yeah. Also think about it this way. I love this question.

51:17 So I, my dad’s 81 now. A year ago he was 80. He started learning how to scuba dive at age 60. He’s now done 2,700 dives and it’s like, so he’s done basically in the last 20 years, 2,700 dives, amazing. So a year ago my dad, I learned scuba diving two or three years ago so I could go scuba diving with my dad.

51:37 A year ago we were in Indonesia scuba diving. Early in the morning, I went on an online longevity site and threw in all of my information to see like how long am I going to live till? And it came back and said, you’re going to live till you’re 98. So I went out and saw my dad. I was 57 at the time and I said, so dad, without telling him what I’d done, I said, dad, how long are you going to live?

51:57 My dad said, ironically, Chip, I’m going to live till I’m 98. I said, wow, that’s really interesting. I just did this survey online and it says I’m going to live till 98. So I said, let’s do the math, dad. If we start counting at the age you became an adult, age 18, what percentage of your adult life is still ahead of you?

52:17 And we did the math and my dad, if we did the math that way and he lives till 98, he’s barely into the fourth quarter of his life at age 80. For me, my dad looked at me and he said, Chip, look at this. If you’re going to live till 98, you’re going to live halfway through your life. At 57, I wasn’t even at half time. Right.

52:36 When you start to do the math that way and you realize that longevity, it may be a long-term trend, probably is a long-term trend, for people who frankly are prosperous. There are actually some evidence that longevity is actually going backwards for certain kinds of demographics. But if you’re going to live longer, and you know, in my case now, I’m 58, half time of my life, hell yeah, I’m going to learn Spanish at 58 because I live in Mexico half the time. That is something 10 years from now, I will look back and say, why didn’t I learn it sooner?

53:09 Frankly, as a curious white boy, we’re going to get to this, who grew up in Southern California, I grew up learning French in LA. Why did I do that? Well, ultimately, it led me to calling my company, Joie de Vivre, so I got one thing out of it, but I should have learned Spanish as a kid. Most of us don’t learn a language after age 45 because it’s harder when you get older. And that could be my little name tag that says, I don’t learn it because it’s too hard.

53:35 Well, yeah, that’s true. Doesn’t mean you can’t try. Because trying to learn how to surf, it sucks some days, right? It does. And you’re like, this is really frustrating and the natural tendency is to go back and mentor someone because you’re good at that, right?

53:48 That’s right. Go give a speech, you’re good at that, and get those little rewards, but then you’re not in the growth mindset. When you’re in the growth mindset, you’re willing to try something new. There’s a great book called, It’s Great to Suck at Something. And so I believe that’s true because it’s this element of saying, I’m not coasting in life.

54:04 I’m trying something new. I’m open to looking like an imbecile. There’s a word that isn’t well known in the English language called liminal. To be liminal is to be actually in between two times. It’s actually to be in transition.

54:19 In biology, the liminality that we’re most familiar with is the caterpillar to butterfly journey. The liminal stage is the cocoon. I actually sort of see life the way I’ve now spent enough time researching this, reading over 200 books on longevity and aging, having all these people come through the Modern Elder Academy, which we’ll talk about. I actually believe life is a little bit like that metamorphosis of caterpillar to butterfly. We’re a caterpillar storing up, accumulating, eating leaves, making sure we get plump.

54:50 And then one day, around midlife, we start spinning our chrysalis and in that chrysalis, frankly, we go into it and that’s midlife. In midlife, it can be dark and gooey. If you open up a chrysalis for a caterpillar halfway through, it doesn’t look like a butterfly. On the other side, there’s this butterfly, this beautiful, colorful, flying creature that actually comes out of the chrysalis. And you are this butterfly who’s, frankly, seems like a different being, but the seeds of the butterfly were in the imaginal cells, imaginal discs of the caterpillar.

55:32 If we use the U-curve of happiness as a way of thinking about our lives and realizing, yes, we hit a cocoon or chrysalis around midlife, it’s a darker period, it’s a bit gooey. And then on the other side, it actually gets better. So the narrative, the societal narrative about it just gets worse with time is actually not accurate on the personal narrative on many people. And if we start to realize, in fact, our brain gets better with age, it gets worse when it comes to recall, like memory, and how quickly you can actually think of something.

56:10 But the thing that people don’t know about the brain, and it’s now been proven, is as it shrinks a little bit, the brain does, we do the left brain-right brain tango, and we actually get better at being able to synthesize things, basically get to the gist of something or in essence think holistically. When you think holistically, it means you can actually almost distill down or to use the forest and the trees metaphor, a young person can see the trees and understands it, but someone can actually, when they’re older, can buzz up to 30,000 feet and see the pattern. So we need to start helping the societal narrative around aging, not just help people understand that, yes, you can get happier, partly because you edit some things you don’t like and you get clearer on your expectations, but no, actually, some things get better.

57:03 Emotional intelligence gets better. Your ability to get the gist of something and think synthetically gets better. Crystallized intelligence increases. Your ability to actually be a better human gets better. So I say all of this only because we don’t have this narrative in society, and so generally speaking, the way we look at our lives is we hit this damn midlife crisis.

57:29 The caterpillar goes into the chrysalis and then all the caterpillar looks forward to is becoming a decrepit caterpillar, when in fact, on the other side of it, there’s actually an opportunity that is quite beautiful. Yeah, and we’ve all met those elders, and I remember I interviewed Jared Diamond, the guy that wrote Guns, Germs, and Steel, and he was in my studio five or six years ago when he was like 70-something, maybe late 70s, and man, he was on fire, and I was like, what’s next for you? I thought he was like, I’m a retiree.

57:58 He’s like, I’m working on two books, and I was just like, goddamn, that guy’s crushing it, and I was just like, wow. I was like, he’s on his game, and it was nice to see. Peter Drucker. Yeah. You know Peter?

58:09 Yeah, of course, yeah. He’s a modern management theorist. He really sort of helped to create modern management and business theory. Lived till his mid-90s. He wrote 40 books, two-thirds of them after the age of 65.

58:22 He’s the one who created Knowledge Workers, the idea of Knowledge Workers. One of the things he did every two years, late into his life, is he actually came up with a new subject that he wanted to become the world’s leading expert on, or one of the world’s leading experts. He had nothing to do with his day job, you know, of being a business professor and author. So it could be Japanese ikebana or medieval war strategies. And he’d spend a couple years just lubricating his heart, mind, and soul on that subject.

58:55 And what he found was the process of actually becoming really curious about something had so many collateral benefits to him. For me, I’ve taken that. For 10 years now, every two years, I’ve gone and said, I’m diving deep on a subject. Festivals were one of them, you know, when I did my festival journey between, is it a lot of even Airbnb and creating a festival website? I was interested by the fact that the more digital we got, the more ritual we seem to need as a society.

59:26 I was fascinated by emotions after I went through my dark period and had my flatline experience. But I was truly in a depression before that flatline experience. So how do I understand my emotions? That led me to writing a book called Emotional Equations, which luckily became a New York Times bestseller. And, you know, I’ve been fascinated by hot springs.

59:47 I love hot springs. So I spent a couple years just like studying hot springs. So now, right now, I’ve been fascinated by the subject of aging and longevity and wisdom that led me to writing this book and creating this academy. So I think the idea that at any age, you can go out and become an expert in something with no collateral damage about learning about it. It’s so much easier today to learn because of search engines and Google and all the ways we can learn.

1:00:19 We don’t have to go to a library if we don’t want to. It’s all there at our fingertips. So, you know, I would just say, you know, if you’re feeling in your life a little lost and a little bit like maybe like the walls are closing in, go find the subject. Anything. It doesn’t have to have anything to do with practicality.

1:00:41 And just say, you know what? I’m just going to spend the next month really understanding the subject and see what happens in your life. Because the thing that’s interesting about curiosity is that, you know, one of the things that they’ve proven is that when someone’s depressed, it’s really a closing down that happens. And the curiosity is the exact opposite. It is an opening up.

1:01:04 Really good advice. What happens when all of you guys get together in Silicon Valley and make me live to 150? Because that’s all you guys are talking about these days. I’m sorry I say you guys. I know you’re in Austin now.

1:01:14 But what happens now that, I mean, if that’s a reality, where now I’ve got a lot more time, is there going to be another book you’re going to write in 20 years that talks about what happens when we’re 120 to 180? Yeah, you know, I think it’ll be really interesting. You know, as Steve Jobs said, you know, late in his life, he said, you know, paraphrasing, dying creates quite an organizing principle for living. And there’s an idea that there are stages in life.

1:01:44 What’s happened, frankly, back in the last 120 years is we have added 30 years, 35 years at this point of longevity to people’s lives in a very short time. And it’s really confused people. It’s why midlife as an era is like such a new phenomenon. I think if we get to a place where we have that kind of longevity into the future, the idea of midlife wisdom schools or the idea of how do people continue to graduate into this new way of thinking about being curious is going to be really essential.

1:02:19 Because it just means that you have to constantly be open to thinking and learning in a new way. I do think that, you know, there’s an element of you can keep your body alive, but if you actually can’t, you don’t have the money to pay for the longevity we’re getting, then that’s, and you don’t feel relevant any longer, that is a problem. Yeah, people will talk a lot about longevity. I had a doctor on recently, and he uses the term health span as opposed to lifespan.

1:02:46 So, okay, you want to live to 150, but are you doing something from 100 to 150, or are you just kind of in a bed? And so that’s going to be interesting. But yeah, imagine, because we used to think, oh, you go to elementary school, junior high, college, and then good luck. But maybe we start looking at it, oh, and then when you’re 45, you go to the Elder Academy, and then maybe when you’re 65, you go to this, and it’s this whole process. So the modern Elder Academy is an outgrowth of my experience at Airbnb.

1:03:14 So at Airbnb, I, by circumstance, found myself to be the elder amongst all these younger people, but I didn’t really have much history to know, like, how do you cultivate being an elder? What I started to learn as I was interviewing people for my book, Wisdom at Work, was, gosh, people don’t know how to move into the midlife period. They’re not very good at mining their mastery for what they’ve learned along the way, or cultivating their wisdom, or then repurposing it.

1:03:48 And there’s the ability to shift your mindset around aging. So long story short is I created a beta test, and we had 13 weeks of programs, 13 cohorts of programs, at a three and a half acre campus on the beach an hour north of Cabo San Lucas in Mexico, in southern Baja. And what we found was that the idea of people, wisdom is not like physics. It’s not something you teach. It’s something you share.

1:04:21 And when you have 18 people in a room, average age 52, which is our program is about average age 52, and we are creating the conditions for people to share their wisdom and actually explore more deeply what it is they’ve actually learned, and what they want to do with it moving forward. You have a thousand years of wisdom in the room, and you create the environment where people start to imagine how they can live their life differently. And so we moved from the beta period, in which people were like, the number one thing we learned from the beta period is people wanted an alumni association, so that’s a sign that they really liked it.

1:05:04 And the groups that actually, the cohorts, had weekly Zoom calls that continued far into the future. So we opened to the public the end of last year, and we had our first academic year. And it was very successful. We’ve now had 500 people from 17 countries come to the program. We use NPS, Net Promoter Score, as our benchmark, which basically is a customer satisfaction metric, and it’s 99th percentile for education and hospitality.

1:05:32 So people are enjoying themselves. And they physically go there and spend time. They physically go there, and you’re there for a week. So it’s a Sunday to a Sunday program. And a lot of the learning is experiential with each other and using nature as a teacher as well.

1:05:47 Like, let me use an example. One example would be mentoring. So mentoring, like, what’s an element of mentoring? Well, an element of mentoring is actually having presence. You know, the absence of presence is absence.

1:06:03 The opposite of presence is absence. We’re familiar with people who are absent when they’ve got their phone in front of their face when they’re talking to you. That is very often what we see today. And so presence is a really important thing to figure out how to cultivate. So we do this exercise where we go down the beach, and there’s a bunch of rocks at one end of the beach, and we actually teach people the fine art of rock balancing.

1:06:28 So where you take a rock that’s smaller than the big rock it’s on, it may have like almost a V to it. So you can’t imagine how you would ever be able to balance this rock on the big rock below it. And the way you balance a rock, you know, if you watch a YouTube video on this, as you say, it’s very much about getting present with a rock, learning to actually adjust the rock. So you’re actually creating a little bit of a divot. You’re creating a divot in the base of the rock.

1:07:00 And even if it has a small base and it’s like vertical like this, it can stand up. And what it is about is that presence, adjusting it to a divot, hearing the click, and then taking your hands away. This is what I call mentoring stones. So the mentoring of people, presence, helping to adjust them, feeling the divot, feeling that they actually can stand up on their own and taking your hands away. So that’s a classic, I mean, not classic, because it’s something we created in terms of a metaphor that people can understand around leadership and mentorship.

1:07:39 But it’s a classic way of thinking about nature and how nature can be a teacher. So we use nature as a teacher throughout the week. We use each other as teachers. The arc of learning is based upon my book, Wisdom at Work. So there are four basic themes in the book or sort of lessons.

1:07:57 It’s to evolve, which we’ve talked a lot about today, which is like, what are you going to shed? What are you going to edit? It’s to learn. We’ve talked about that a lot today. Those first two are hard.

1:08:07 Evolving means getting rid of what we’ve been in some ways, some of what we’ve been. Learn means being a beginner’s mindset and having that growth mindset. Then it’s collaborate. One of the great advantages of being an older person is you get better at collaboration. Lots of evidence of that.

1:08:23 And then there’s council, and that’s the fourth one. So the week is that theme or that arc. Interestingly, for people, it’s like council, the idea of being an advisor, a counselor, a mentor, is what happens last. And many people I know who try to operate from that place of being an older advisor and are doing it as the priest or the parent go straight to step four. And you can try to do that, but generally speaking, if you do the first three steps first, step four is easy.

1:08:55 And I had over 100 mentees at Airbnb and still have many because if you do those first three steps, you become a magnet. Wow, that’s really fascinating. Well, we’ll compare notes on academies after this. Tell me about Burning Man. I’ve never been to the burn.

1:09:11 I know it’s coming up. You sit on the board of it. I guess you’ve been to quite a few. What is it for people that don’t know what it really is? Yeah, what it really is.

1:09:21 Somebody might not even know what it is. Yes, let’s start with what that is. So it is an event. The organization hates to call it itself a festival, but that’s how a lot of people describe it. In the Nevada desert, about two, three hours from Reno, Nevada, pretty isolated location, the bed of an old lake.

1:09:43 And it’s an art festival. It’s a festival where art is sort of at the heart of it. But it is not just an art festival. It is also sort of a utopian mindset and experience in self-reliance and community. So there are 10 principles that define Burning Man that are principles that could define someone’s life.

1:10:05 And so it’s a community experience. There are 70,000 tickets a year of people who can come. Two-thirds more people than that. So 140,000 people try to come, but can’t get a ticket. And it’s an opportunity to really experience creativity.

1:10:20 Brian Chesky, CEO of Airbnb, the first time he went was the year that I joined the company. And he said, Chip, this is what the world would be like if artists ruled the world. Now, having said that, what are the ways people see Burning Man? They see it through a lot of lenses. It’s a party in the desert.

1:10:39 It’s a bunch of tech people, Silicon Valley, going out and getting creative and taking drugs. It’s people being naked. It’s sex. It’s a lot of things. Yes, all of those things exist there.

1:10:53 But there’s a family camp with 6,000 people and families, lots of young people. So it’s not just a bunch of young people. It’s actually people of all ages. It’s not just people going out and partying. There’s a whole 12-step part of Burning Man.

1:11:11 What defines it for people who love it is it’s an alternative reality. When you’re at Burning Man and you’re a burner, so to speak, there’s the default world, which is the world we live every day. And in the Burning Man world, it’s all about the alternative reality we could create for ourselves, not because we’re taking psychedelics necessarily, but because we’re actually a participant as opposed to a spectator in our lives. And we are using our own self-reliance, but then that sense of community to actually build something from scratch.

1:11:54 The thing that’s very true of Burning Man is every year it absolutely starts from scratch. Leave no trace is sort of core to it, which means when the Burning Man village starts to be created each year, it’s starting with nothing there. And your camp that you create with your team is a theme camp often that has its own personality and identity. So it’s a lot of work. Anybody who goes to Burning Man thinking they’re just going to go for a day or two of partying and spectating isn’t really getting the experience of what it’s like to be part of a community.

1:12:30 So it’s a week of work and you should go there? It could be. I mean, listen, the first time I went, it was like for three days, and I went on an RV with a friend and we were just on our own and we didn’t build a camp. But I learned 20 years ago when I did that, 21 years ago, that okay, that was one way to have the experience, but that did not give me the sense of community that I felt since then. Okay, and there’s no money exchanged.

1:12:56 Yeah, the only money is for coffee and for your ticket to go. So there’s a de-commodification, which means like money. If there’s a currency at Burning Man, it’s probably love, and it’s a gift economy. So you end up going from camp to camp, meeting people, and they say, come on in and have dinner with us or have drinks. We’re having a conversation about tribalism and let’s come on in and we’re having a conversation.

1:13:27 So it’s very fluid in terms of how people interact with each other. Sounds fascinating. A couple things about you. What’s something for you, daily habit that’s non-negotiable, that makes you who you are? Daily habit that’s non-negotiable is I meditate every morning.

1:13:42 I try to do it twice a day if I can, but I do meditation in the morning. If I don’t have a lot of time, it’s five minutes. If I have a good amount of time, it’s 20 minutes. And every morning in the shower, I say three prayers and four mantras. The four mantras I say, actually, I’m sorry, it’s six mantras now, six mantras three times each.

1:14:03 So that’s pretty much what I do every day. Mantra like a chant? Mantra, so for me, the mantras I’ve created over time to help me embed something in my brain. Everything from I’m lovable for who I am, not what I do, because I’m an accomplishment junkie, an admiration junkie. And so I need to remind myself that it’s not about my accomplishments that make me lovable.

1:14:29 That’s one of six. I have prostate cancer, intermediate stage prostate cancer. So two of the mantras I say three times each are my tiny cancer cells are dying and my body and prostate are full of health and vitality. Do I believe that the affirmations I say every morning have an effect? I don’t know.

1:14:54 I’ve been doing this for 25 years. Those last two are something I’ve done in the last year since I had the diagnosis. Good news is in the last year at an intermediate stage prostate cancer diagnosis, which is probably the reason I have to pee right now. Yeah, I think I should let you go. Is that I’ve had no growth in the cancer.

1:15:14 And yes, I’m open to having Western medicine and having my prostate taken out or radiation. But the thing that’s been really interesting is at an intermediate stage, which is really bad at my age, but I’m doing supplements, acupuncture, and I have a shaman. We have a shaman in the modern elder economy. And I’m doing some non-traditional things and for the past year, there’s been zero growth in the cancer. Wow.

1:15:39 The prostate cancers move slowly so that’s part of it as well. Thoughts on cancer? Like when you get that diagnosis, what was that like? Well, oh man. So first of all, I didn’t know many signs.

1:15:51 I had just a normal physical that led to a blood test that led to finding out through a biopsy that I had prostate cancer. I found out the day after my book came out, so I was in New York on a book tour. It was the day before, the night before I was giving a TED talk at TED headquarters, TED salon. So the timing was just awful. It was six weeks before we were opening the Modern Elder Academy to the public.

1:16:20 We actually just signed the contract to go to a second location for the academy because we knew it was going to be successful. So it was inconvenient. That’s how busy you are. Yeah, the first thing I think I would say is like, okay, exactly. I was like, okay, cancer, what are you teaching me?

1:16:39 Just like nature. Nature is a teacher, you know, like the mentoring stones. Cancer can be a teacher and I want to graduate from the school and move on from this teacher. But if I can say that for the last year, what has cancer taught me? Number one is that I need to listen to my body more.

1:17:04 Yes, there were some signs, small signs I probably should have noticed that would have said to me, something’s going on with my prostate. But I wasn’t noticing, I was too busy. Secondly, the editing function in my life, which I tend to edit pretty easily, but then I add things because I’m so curious. The challenge with curiosity is that you add. And so I have a tendency to take on things, get passionate about them, and then not realize how much I’ve taken on.

1:17:42 And so cancer basically woke me up and said, so let’s distill this down to what’s truly essential. And that was a helpful thing for someone who does as many things as I do. Thirdly, I’ve actually really appreciated, I appreciate how much love I’ve gotten along the way and all the different people who want to tell me what I should do. Like the number of people who have a family member or someone who’s had prostate cancer is huge. And I’ve also had to say enough.

1:18:18 And then trust my intuition about like, what is the right path here? And so one thing I will say about any cancer diagnosis or any diagnosis of a serious illness that you don’t know anything about is you better create five to seven hours a week in your life for it. Meaning, for me, it was like learning about it, going to appointments, you know, having second or third opinions. And so what I really needed to do was to sort of say, what’s the diagnosis, what’s the path for me here?

1:18:55 And it’s been a combination of Eastern and Western medicine. And it’s also been a time for me to, cancer’s been a teacher for me to be less purely self-reliant and to sort of open up from a vulnerability perspective to having close people in my life support me emotionally. This was particularly true in the first two months. So book comes out, TED Talks happening, Modern Elder Academy is going on, book tours going on. And so I really, and I was starting to do some treatment, nothing radiation-wise, but some energy and herbal treatments that were actually having a physical effect on me.

1:19:42 And so, ah, man, I was really raw at a time where in some ways I really could use, could have used almost a detox away from everybody, but I was very much on display. And that was hard. And so being in a place where I could talk about that with friends and ultimately with the Modern Elder Academy, it was a very interesting, ironic time. People come to Modern Elder Academy in many ways to help themselves through a transitional, how to navigate midlife transitions.

1:20:15 And many of those midlife transitions require a certain amount of vulnerability. And here’s the founder of the place, finding out six weeks before we opened that I have intermediate stage cancer. So I was ripe for being not just the teacher there. I was also the student. Did you ever think about not telling people?

1:20:39 I had certainly people who told me don’t make this public. And, you know, I didn’t go on Facebook and broadcast it immediately. I did a few weeks into it because people started to hear it. You know, the challenge with actually keeping it private is a couple things. Number one is if you live your life relatively in a public way, which I do, the idea of actually keeping it private almost makes it feel like it’s shameful or you’re not being, you’re not in integrity.

1:21:18 To be in integrity, you know, the word integrity is interesting. It’s integrate and also means wholeness. So wholeness speaks to the idea that like your whole life is sort of being defined by this. So if I say, you know, that I’m an open book and yet I’m not talking about it, it didn’t feel like I was being in integrity. And then there’s just sort of the reality that those people who are hearing about it and they weren’t hearing about it from me, but they’re hearing about it in another way, felt like they were lesser than in my life.

1:21:53 Like I must not be close to you if you haven’t told me about this. And so I didn’t want anybody to feel that way. And of course, that’s pretty selfish on your part. You know, your cancer is bumming me out. I didn’t have anybody say it that way, but I definitely had a couple people who had hard feelings about the fact that I hadn’t shared it with them.

1:22:20 But at the end of the day, that’s their problem, not mine. And it was not, in many cases, it just had to be like, okay, there was a small group of people that I was sort of going through it with the first few weeks. But I knew as we were getting closer to the academy, I’m going to be talking about this in the academy with people I don’t even fucking know. So yes, someone I grew up with and has been in my life for 40 or 50 years. And one of the positives of Facebook, it has a lot of negatives as well, is it allows you to broadcast something hopefully from a place of not narcissism, but a place of trying to be candid.

1:23:07 And I could do that in a way where people could understand what I was going through. Okay, cool, thanks for sharing that. Why move from San Francisco to Austin? And for people that have never been to either city, what are they like and what is the feel? I mean, I’m from California, but I’m from San Diego, which is completely different than San Francisco, so why?

1:23:26 So Austin has a lot of qualities that remind me of San Francisco from when I first moved to San Francisco. I moved to the Bay Area in 1978 to go to college, Stanford, then business school at Stanford, and moved to San Francisco in 1984. San Francisco was a place people tended to move back then for lifestyle reasons. They didn’t move there for career reasons all that much. So there was an element, and San Francisco was sort of an art, there was back then, keep San Francisco weird.

1:23:55 You know, everybody always knew San Francisco weird. Like, who thought it was going to like not be weird? But there was an element that, you know, we didn’t want the Manhattanization of San Francisco. That was, you know, a whole political campaign in the 1980s in San Francisco. So San Francisco was sort of a lifestyle driven place.

1:24:12 I loved it for that, it was very artistic, probably half my friends were artists and sort of creative types, which was a great thing, having gone to Stanford Business School and hung out with a lot of type A people. With time, first with the dot-com bust and then more recently with the tech era that we’re in right now, San Francisco started becoming a little bit more uniformly a, you know, one industry town, sort of like Detroit or Houston, with, you know, music or oil. I’m not music, well, I’m music, look at me, good for me in Detroit, well, cars and oil.

1:24:46 Yeah. Or LA with entertainment. So it got a little less interesting. I think there’s that chance. Of course, it’s gotten more expensive, et cetera, et cetera.

1:24:58 I don’t want to beat up on San Francisco. San Francisco has all kinds of wonderful things about it still. But for me, what started to become clear was I like the pioneering spirit of a place. And I have been intrigued with Austin for a long time. I first went there 20 years ago, helped a woman named Liz Lambert create her hotel company, Bunk House, with her first hotel.

1:25:20 And she’s probably one of the best boutique hoteliers in the U.S. today. So I was her mentor 20 years ago. And loved doing that. And then loved Austin.

1:25:28 And over the course of time, I have four different companies that I have some relationship with. A couple of them I have an ownership in. And so I was spending more time there going to give speeches there, speaking at South by Southwest every year. Then I actually have two sons, biological sons, with a lesbian couple in nearby Houston. So Austin and Houston are close.

1:25:50 So I was like, okay, well, maybe I want to be closer to my sons who are four and seven. And so that was another reason. They know your dad. They know I’m dad. They do.

1:26:00 And they’re deeply in my life. So for all those reasons, I got to the place where I said, Austin’s the place I want to go. What’s interesting about both places is back in the day when I moved to San Francisco long ago in 1984, when I’d say 1985, 1988, 1992, I lived in San Francisco, almost anybody universally would say, oh, what a great place. That’s what people say about Austin now. And whatever your political stripes or whatever your interests, it’s a diverse place in the sense that it’s got its cultural, artistic, diversity, live music capital in the world, supposedly.

1:26:43 But it’s got a government focus because it’s the capital city of Texas. It has a major tech focus and a commercial focus. And so what I’ve found is that when I say to people, I live in Austin now, they’re like, oh, what a great place. And so I think that in many ways, Austin has some of that flavor, that frontier pioneer spirit. It’s a lot more affordable, although that’s changing pretty quickly there as well, and traffic is changing as well.

1:27:14 But the thing that’s interesting about Austin is, I think it’s adapting into its tech world in a way that’s allowing it to not be a one-industry town. And because it’s the state capital, and because it’s University of Texas is an enormous university, it has those elements as well, and because it has that live music component. Yeah, I think it’ll stay interesting for a long time. I’m going to come visit. Yeah, come visit.

1:27:44 If I were to ask all your friends, what’s Chip’s superpower? What would they say it is? What allows you to do what you do, do you think? Every five years, I throw a big birthday party, and I started doing that at age 30, and I’ll have my 60th one next year. Somewhere in the world, Bali, Burning Man, Marrakesh.

1:28:05 Great city. Marrakesh is great city. Yeah, that’s great. Someone called me at the last birthday party, which was in Baja. They called me a social alchemist.

1:28:17 I think that’s a superpower I have. Being able to know how to create the mix of people, whether it’s in a dinner party, or whether it’s a community. I’ve had enough history, whether it’s with Burning Man community or Airbnb’s community, the modern elder community, which has become sort of a movement of people in midlife, to know how to mix people together and make it combustible in a positive way. And so whether that’s in a team or in a company or in a party or festival.

1:28:52 And so I think that is understanding individuals and then how when you mix individuals in the right way, with the right conditions, you create quite a cocktail. And so I would say behind that superpower of social alchemist means I am lucky enough to have, at a relatively young adult age, had to go through some difficult, challenging times and emotionally, that actually helped me to mature quickly in terms of understanding who I am. Oscar Wilde, here in London, long ago said, be yourself, everyone else is taken.

1:29:33 I think that is a maxim I took to heart in my early 20s and has served me well. What was the best day of your life and the worst? Wow, I think the best day of my life. Yeah, actually, that’s a really hard, that’s a great question. I think the best day of my life, I’m going to say something that just first came to me, which is on my virtually my last day at Airbnb full time, four years into it, weirdly enough, the timing was we had what’s called one Airbnb, which is we brought all of the employees around the world together.

1:30:11 So for a company that when I started with them four years earlier, I had 250 people maybe in the company. At that point, I had 3,000 employees four years later. And we had a dinner on the third night, the last night of this three day sort of love fest of the company. And Brian asked me to give sort of a keynote address at the end of dinner. So everybody’s been drinking, having a good time at the end of three days.

1:30:35 And Brian gets up there and just says some beautiful words about me and gave me the opportunity to get up. And as he said it, Chip’s giving his own graduation commencement speech because he’s graduating from us. He’s no longer going to be a full time employee, he’s just going to be an advisor. And I was able to in 15 to 20 minutes speak from my heart to 3,000 people who had become my family and talk about what I’d learned along the way and what I thought they could take with them.

1:31:05 So that was a great day just because I could feel the sense that I could distill the wisdom that I’d built over the course of time and could pass it on. But also Khalil Japran in the book The Prophet said, work is love made visible. And that was the first thing I said when I got up there. I had nothing planned, I just knew I’m just going to talk. And the first thing I said is, this place has reminded me of this quote, work is love made visible.

1:31:32 And by the end of my talk, 15 to 20 minutes later, probably 80% of the people had been crying. And there was a sense of like, wow, there’s something powerful here, not just in this company, but in the relationship of this old guy who’s had an effect. So I haven’t really talked about that a lot. I actually finished my book talking about that, but I don’t really talk about it very much. So thanks for reminding me.

1:31:59 Was it time to go? Is that why you left? Yeah, I was burnt. I was starting to have the early stages of prostate cancer, but didn’t know I had it yet. Remember, I joined for 15 hours a week, and quickly it became 15 hours a day.

1:32:14 I still had a full life. I wasn’t looking for a job. So it was hard to juggle my life, and I felt like the work that I needed to do had been done. And from that point forward, I felt like my best role is not to be literally helping steer the rocket ship with them, but it’s to just be an advisor. Right, the rock was set, so you let it go.

1:32:35 Exactly. Worst day of my life, I would say when I found out my friend Chip, who was almost like my spiritual advisor and who’s my insurance agent and one of my closest friends, I was about to give a speech, weirdly enough, in St. Louis, which is four months later where I actually died. I was in St. Louis, not in St. Louis all that much, but four months earlier, five minutes before going on stage to give a very large speech, I got a call from Chip’s boss and found out he’d committed suicide.

1:33:12 And over the prior couple of months, I had been talking to Chip about how depressed I was and how I could see. I’d gone through the dot-com bust with my company. We were by far the largest independent hotel company in California, but way big in northern California, in the Bay Area, and the dot-com bust basically killed the Bay Area. And we made it through that, and we survived. And then just after getting through that, two years later, the Great Recession comes along.

1:33:42 And then early 2008, we could see it because the hotel industry basically feels the effects of a recession faster because people cut back on travel spending. So I could see that this was going to be a very punishing recession, much more so than people were predicting. And I didn’t want to be doing this anymore. I was ready to take off my name tag that said, I’m the founder and CEO of Joie de Viv, and I wasn’t feeling much joy of life. And so Chip was the person who was helping me through that time, and I had no idea that he was going through his own difficult time.

1:34:17 He had a wife and two kids, and he committed suicide. And I found out in a depressed state myself right before giving a speech on stage about Joie de Viv and about how to create self-actualization in your life. And so over the next three or four months, everything that could go wrong did go wrong in my life, leading me to that flat-line experience. And I lived through that experience. But over the course of that Great Recession, I had five friends commit suicide, three of the five entrepreneurs who had basically seen their self-worth as their net worth.

1:35:01 And they, as their companies, cratered their sense of identity, did as well. And as such, they took their lives. In many ways, that’s part of the reason I ended up, I think, at Airbnb, to learn that there’s something we have that’s of value later in life that we need to cultivate an offer to other people, younger people. It’s part of the reason why the Modern Elder Academy is something, it’s a social enterprise. 60% of the people coming are on scholarship.

1:35:39 I don’t make a dime. I built a $4 million campus. I pay no rent to myself. All because I believe society is better off if we have intergenerational collaboration and we help people in midlife realize that even when the walls are closing in on them, or even when the circumstances of their life are falling apart, there is something to be learned from it. And on the other side, you might become a butterfly.

1:36:06 You said earlier, what is this teaching me? Is that the question that you suggest people ask that when things like that happen? Yeah, when the world’s falling apart, the question I ask, and I ask it on a weekly basis at the end of every week, I have a wisdom book. I have 30 of them at this point, 30 books of the Wisdom of the Week. I write down my Wisdom of the Week, especially in the worst of times, because generally speaking, we learn more in the worst of times than we do in the best of times, and it helps me to understand how do I take that learning and use it in the future.

1:36:42 It’s powerful, very powerful. What scares you? I think in the past, my ego scared me because I didn’t really have much control over it. And this is why this whole thing, the idea of the first half of your life, the operating system is operating. Also, the hotel business is probably big for egos.

1:37:02 Oh, big for egos. I mean, the restaurant, hotel business, I had restaurant spas. Richard Branson wrote the foreword in my first book, The Rebel Rules, and people called me like the little mini version of Richard Branson in the Bay Area. So I fed my ego in what I did. So I think what scared me back then was what level of control does this thing have over me?

1:37:26 What scares me today, I think what scares me a little bit today is the toxic nature of social media and politics both separately and together, social media and politics. It’s pretty combustible. I think what scares me today is the lack of civility that we used to have. And I don’t come at this from the perspective of we all are perfect or like somehow we have to be all righteously good. But I come at this from the perspective of when in doubt, assume best intentions.

1:38:09 And I have found as a human, a human who grew up in a predominantly white neighborhood but went to junior high school and high school in the inner city where I was the curious white boy at LBC, Snoop Dogg’s high school. He was 10 years younger than me but went to Snoop Dogg’s high school. That no matter who you are and no matter who you’re surrounded by, especially if you’re the other and I was the other as the curious white boy, I was not the dominant demographic.

1:38:41 If you can actually create an environment where you can assume best intentions, especially with people who are the other, who are different than you and you can come at it from that perspective. That welcome mat of assuming best intentions in the vast majority of the cases is going to create a mirror neuron playpen where you’re getting along and you actually treat each other well. And good stuff comes out of that. Yes, you have to protect yourself and yes, there are people who will take advantage of you when you put the welcome mat out.

1:39:19 But unfortunately, we’ve created an environment where there’s no welcome mat. There’s viciousness and there’s assuming worst intentions and there’s contempt. And all of that leads to an environment where we actually show up with our worst selves as opposed to our best selves. And when you create a world where everybody’s showing up with their worst selves, you’re creating a world where you want to retreat from that world. One of the things that’s really interesting about living in a very rural part of Mexico where everybody just served happy all day long and people come to our academy and just are like, oh my God, this place is a paradise.

1:40:00 Who knew four years ago when I started going down to this place eight or nine years ago, four years ago when I started buying a place and then it was just my home and then I built the campus. Who knew the refuge of a place that allows people to be their best selves surrounded by other people who are their best selves in a community where the local community all feels very much like people who are very thoughtful and caring of each other. Who would think that that’s an unusual part of the world today?

1:40:32 And I think in places like the UK and US which are going through such divisive times, there’s such a thirst for us to get back to a place where we can have a civil discourse. It doesn’t mean we all have to agree, but it does actually mean we have to sometimes assume best intentions. Do you think the fact that probably 99% of our interactions now are online as opposed to in person just drops that civility level so far down? Yeah, anonymity, the lack of accountability of what you’ve just said, would you say that’s that person in person?

1:41:10 Yeah. Would you say that face to face? Yeah. It used to kind of be anonymity like five years ago, and now that doesn’t seem to stop anybody, but it’s the fact that they’re not in front of you, and then it’s just this digital thing, and then, yeah, the civility goes down the drain, and then it becomes the normal. But yet, if the person was in front of you, you probably wouldn’t say that, although these days, maybe after your condition to that, you would.

1:41:32 Well, I think we would. I think that’s what’s happened, is that actually it’s gotten so serious that… Like our digital selves in front of each other. That’s right, yeah. So, you know, I have lots of thoughts on how to solve for this.

1:41:45 I’m reading a book by Arthur Books right now called Love Your Enemies. He and I don’t share politics. He’s sort of center-left, he’s center-right. But he wrote a beautiful article on The Atlantic about people in midlife feeling somehow irrelevant overnight, and they’re like, oh, I can relate to what he’s talking about there. And it’s a great book, and David Brooks, also center-right guy, his book The Second Mountain, speaks to a lot of the same themes.

1:42:21 And I think that the real thought here is, when you get to a world where you sort of see yourself as right and everyone else is wrong, you’ve created boundaries that really limit our potential as a species. Because now you’ve just become the warden at the border to figure out who can come within your boundaries and who can’t. And for you and I who grew up in an environment where we were the curious white boys in inner city environments with people who were different color skin, different culturally, and realized, my God, I can learn so much from them.

1:43:07 Or use the example of Airbnb. I can be the old guy, the other, amongst the young people. You start to realize that we have a lot more in common than we think we do. Yeah. Yeah, you bring back memories, you know, for me, too.

1:43:21 So when I was in fifth grade, my mom sent me down. Actually, funny enough, at a French immersion school where French was taught the first half of the day and then English the second half, everything was taught in French. That was actually when I was in fourth grade and then in fifth grade up until tenth grade. I was bused about an hour down south into these programs called magnet schools where the science and the computer science was off the chart. Yeah, advanced placement.

1:43:44 Yeah, E.P. courses, everything. I mean, it changed my life. And yet, it was 80, 90 percent black and Hispanic. So it’s like, boom, and I came from La Jolla, Pacific Beach, where it was all white people and suburbs.

1:43:56 But for me, I was such a young age that it was just normal, and I had never really encountered racism in my neighborhood. So for me, it was just different people. I also got beat up sometimes and stuff, but I never took it, it wasn’t a race thing. It was just like, I’m the weird guy thing or just a different person. And I think I took a lot from it, a lot from it.

1:44:17 I probably don’t even know what I took from it. What the world needs more of is, what does it mean to be the other? You know, the other, what does it mean? Like, let’s define the other. The other is generally the person who’s not dominant in the environment that they’re in.

1:44:31 In many working places, that’s a woman. In many places, it’s a person of color. In some places, it could be the white person. It could be the gay or lesbian person. It could be the person is disabled, this person is older or younger.

1:44:45 So when you’re the other, here’s what happens for the other. You often get characterized as what you do as being defined by stereotypes. So we don’t define, the dominant person isn’t often defined by stereotypes because the culture is the stereotype, generally. But when you’re the other, you end up getting characterized and sort of the shorthand is, you’re the stereotype. Or if you say something, you’re representing your race, your sexual orientation, your gender, your age to everybody else based upon that, which is really unfair because you’re not being seen for an individual person.

1:45:27 But also people then are prejudging you before a word comes out of your mouth because you are the other, and this is what I understand about your kind of other. And so it’s sad. It’s an unfortunate thing. It’s a burden that people don’t recognize. And I think for straight white men, and I’m not here to beat up on straight white men, the idea of it is how do you help yourself understand what does it mean to be the other?

1:45:54 Go to a hip-hop festival with your family and understand what it means to be the other. Go to the gay and lesbian pride parade and see what that feels like to be the other. Go to a workshop on emotional awareness as a man, as a straight white man, and see what it feels like to be the other because I promise you, you will not be in the majority in a workshop like that unless it’s a men’s workshop. So those kinds of things help you to start to see, oh, what’s it like to be not in my common habitat?

1:46:33 Yeah, that’s powerful. And to realize that we’re all stronger with all these different diverse ideas and opinions, right? Just like the old guy at work can make us stronger and then the young person’s perspective can make you stronger. What would we be surprised to learn about, Chip, something you do that maybe isn’t reflected in your CV? I think, well, so what we haven’t talked about at all, and I’m open to outing myself as a segue from this discussion, is at age 22 I came out as a gay man.

1:47:01 And as someone who wanted to actually be president of the United States some day, as someone who played water polo at Stanford and was in a fraternity, as someone who wanted to be a CEO some day, as someone whose dad was a marine captain in the reserves, and I had the exact same name as my dad. I was the chip off the old block of Stephen. I was Stephen, Jr., only son, oldest child of two parents who sort of had high expectations for me. It was really hard. And so I think what I said earlier, so being the other, I had to learn out what it meant to be the other as that LGBTQ person in a generally, although in San Francisco, frankly, sometimes we’re the majority in certain groups.

1:47:47 But it helped me to get really clear on who I was at a pretty young age. So I think a lot of my self-awareness, so someone could say, oh, I’m so sorry. Back then I did have a lot of people say that to me. I’m so sorry. And this was back in 1983, partly because I came out this summer that on the cover of Newsweek magazine was the gay cancer, which was AIDS.

1:48:12 That’s what they were calling it at that time. So the idea of coming out as a gay man at 22, when frankly, there was a sense like, man, being sexual in this environment means it’s a death sentence, was a really hard thing. So what I’ll say is that my process of having to get clear on who I was and as Oscar Wilde says, be yourself, everyone else has taken, helped me at a young age understand who I was. And that process of understanding who I was has carried me through my whole life, allowed me at age 26 to become a CEO.

1:48:48 Yeah, I was a gay CEO, but I was a CEO. But I was also a CEO who understood diversity, understood empathy, understood frankly as a boutique hotelier that I had a design eye for things that may have come from my sexuality, because somehow gay men are better at aesthetics sometimes and design. So I didn’t ever feel like I had to hold back who I was, which allowed me to actually really fully live into the person that I could become. So yeah, something that actually could have been seen as an obstacle has actually proven to be in many ways a beautiful gift.

1:49:37 Yeah, you really have to get to know yourself if you’re doing that at 22, especially after the fraternity and the water polo. The world I lived in was like not ready for that. I mean, I was a fraternity at MIT, but I can only imagine in the 80s at Stanford. Oh, my gosh. Yeah.

1:49:52 So it’s not on my CV. If you go check me out on Google with gay Chip Conley, you’ll see some, you won’t see any naked pictures or anything like that, thank God. But what you’ll see is that, yeah, there’s been a lot of articles written about me and that I think it has helped me to be the other and understand it when someone naturally looks at me and says, oh, straight white guy, you know, doesn’t understand me. And I sit down with someone, I was like, you know what, you have empathy.

1:50:21 Where’d you get that from? Well, I got it from the fact being a curious white boy a long time ago. Got it from being a gay man. Got it from being the old guy at Airbnb who was different than everybody else. So I have, as much as I come across and look like, okay, I’m from the dominant culture, I’ve had a lot of opportunities to be the other.

1:50:39 Yeah, thanks for that. I’m gonna be thinking about the other now and all my interactions, just seeing how I can make sure they don’t feel like the other. What keeps you awake at night? What keeps me awake at night is when I have not lived up to my potential or I have been unfair to someone else or if someone’s been unfair to me. Fairness is really important to me.

1:51:09 So fairness is somewhat of a, you know, it’s in the eye of the beholder. So if I feel like something is unsettled because of a fairness issue, I try to actually address it pretty early because I don’t want it to fester. Whether it’s my sense that I was unfair to someone or someone was unfair to me. Yeah, so that can keep me up at night. Okay, interesting how we have this kind of innate sense of fairness on.

1:51:35 Yeah, yeah. To me, fairness and your conscience have a lot to do with each other. Yeah. And generally speaking, not sleeping at night has a lot to do with my conscience. So, yeah.

1:51:48 Well put. Chip, I always ask a few questions at the end. I’m gonna ask you if you can make a phone call to the 20-year-old Chip and give that young man some advice based on everything you know right now. What would you tell him? The following success secrets are only available inside the London Real Tribe, where you get exclusive access and insights from our high-performance guests on wealth creation, productivity, leadership, morning routines, health, and well-being.

1:52:15 To join our Tribe community, go to londonreal.tv forward slash Tribe. Now, let’s continue with the show. Yeah, it’s one of the most things I get asked about all the time and maybe it’s because of my relationship with Dan, but I think it’s so important and it’s changed my life having that mentor relationship and I haven’t had that many in my life because I never knew how to do it. It just happened. This happened serendipitously, but also I gave him something by inviting him on the show because I actually had something to give and that helped.

1:52:41 Dan always has a few rules on mentorship, which are kind of interesting, but he always says the mentee always buys the mentor, always pays for the bill. So even though he’s the $50 billion man, I always buy dinner and I just think it’s a small thing. I like that. I like that. And he also, he had three mentors in his life.

1:52:56 One of them was Costa Scratzos, which was part of the Onassis shipping lines. He was like CEO and they had a few others, but they always had a mutual interest outside of what he was being mentored in. So with Costa Scratzos, it was food and wine they both enjoyed. One of them was tennis, one of them was golf. So they’re not talking shop all the time and they can just have something.

1:53:16 Nice. So it’s good stuff. Chip, this has been amazing. So thank you so much. This stuff is really, really powerful and it’s going to make me think a lot about my own life, but just this whole concept, I mean, I think as young people, they inherently know they need that wisdom.

1:53:33 And you see the really smart ones making the valley as examples, but people that have billions, they look like they’ve got it made. They have the plan and yet they’re still smart enough to seek out these… Smart and wise. Yeah. It’s a marriage.

1:53:47 It is. And so many people need to see that and then embrace these people in the workplace. And so many older people out there need to be empowered by this to know that we need you, we need you there, as long as you’re acting like the elder, which means you’re constantly revising yourself and it’s a great way for everyone to grow in the culture and just contribute. So I love it. How do they find out about The Elder Academy?

1:54:08 Check it out. Modernelderacademy.org or .com and then also chipconlay.com. Okay. And this and many books, I’m guessing on Amazon. Wisdom at work.

1:54:17 Yes. How many books? Five? I got five books so you can find them all on Amazon or at chipconlay.com. You’re on a mission.

1:54:25 You’re a machine, Chip. Thank you. All the best with the recovery and the process with that. Thank you. And just thanks so much.

1:54:31 This was eye-opening. Yeah. I enjoyed being here. Thank you. Okay.

1:54:36 Awesome. Thank you, sir. Appreciate it.