Transcript
This isn't your average business podcast, and he's not your average host. This is The James Altucher Show. Today on The James Altucher Show. People always ask, what number do I need to retire? Which is almost an antiquated question because retirement's starting to become an antiquated word. Yeah. But I understand it. What does financial freedom mean? And so let's just hypothetically say, you need 10,000,000 because you'll make 4% every year after taxes conservatively, so you can live a great life with 400,000 a year. So let's just make up that number. But the flip side is, if you love what you're doing and you don't have 10,000,000 but you're making 400,000 a year, it's as if virtually you have 10,000,000. It's as if your your virtual net worth is 10,000,000 because you would be doing this anyway and you're making this income stream. And you discuss that quite a bit in the book with some fascinating stories. Yeah. You know, I had gone from being the pioneer as a boutique entrepreneur, hotel entrepreneur in my mid twenties, to being the establishment by 52. And then within the first couple weeks, I was like, oh, wow. I'm I thought I was supposed to be the mentor here. Brian Chesky, the CEO's mentor. I'm the intern. I don't understand the language. This tech lingo. And frankly, I was twice the age of the average employee. So I decided, gosh, the only way I'm gonna survive here is to be as much of a curious learner as I am the wise sage. And that's what a modern elder is. A modern elder is not like the traditional elder of the past, who is regarded with reverence. A modern elder is all about relevance. And relevance is taking that timeless wisdom, and applying it to modern day problems. But that means you have to actually be a a lifelong learner. But I was very comfortable being the the person who asked the most questions in a room, and quite often the most naive. Let's roll. Jay Jay, put up a sign at, like, 10:50. Perfect. And let's get started. But I just wanna say, not only did I really enjoy it, you know, I just got it, so I just I just read it in the past couple days. But I'm deaf like, as you suggest towards the end, I'm gonna definitely read it again because I think it is a guidebook to the modern elder, and I never thought of it that way, as a modern elder. Well, you know, when first someone first called me the modern elder at Airbnb, I was like, really? You know, elder and elderly sound a lot alike. And, but there's a big difference. And we'll talk about that. I don't I don't wanna, but you tell us when you're ready. The audio is already rolling. Okay. I'm just rolling the camera right now. Okay. And, you know, it's good to go. So once again, I am so happy to have my friend Chip Conley on the podcast. Chip was when we first met, Chip was the head of hospitality at Airbnb. Welcome to the show again, Chip. It's great to be here, James. You you've changed your digs. It's no longer your living room. It's a, you know, a real studio. Well, that was a living room at an Airbnb. Even better. Yeah. And upstairs from where I was. Right. So we were in the same building. So so my Airbnb host at that time called me and said, hey. The head of hospitality for Airbnb is at the Airbnb right below you wants to hang out. And so you came upstairs. We have a bottle of wine. That's right. We have a bottle of wine. Hospitable. I was gonna bring a bottle of wine to this, but then I figured, oh, you wouldn't wanna lug a bottle of wine around all day. It's 10 AM in the morning. No. I think I'll pass on that. Yeah. But, we did a podcast then, and and then you invited me to speak at the Airbnb open, which was so much fun. I just had a great time. And now you've you've changed your role at Airbnb. You're a strategic adviser. You wrote this great new book that just came out, Wisdom at Work, The Making of a Modern Elder. You know, I have so many questions and so many stories and things I wanna talk to you about, but define modern elder. Yeah. So, I joined Airbnb at age 52. I'd spent 26 years before that being a boutique hotel entrepreneur. The 3 young founders in early 2013 approached me and said, we're a fast growing tech startup, but no one in the world sees us as a hospitality company. We wanna democratize hospitality. Will you join us? And I was like, okay, democratize hospitality sounds pretty cool, but what's Airbnb? Because frankly, I didn't have an Uber lift out from my phone at that time. I'd never heard of the sharing economy. This is almost 6 years ago. And I was, oh, really? People stay in each other's homes? What a interesting, but sort of weird idea. And I was like, I had gone from being the pioneer as a boutique entrepreneur, hotel entrepreneur in my mid twenties, to being the establishment by 52. So I said yes. And then within the 1st couple weeks, I was like, oh, wow. I thought I was supposed to be the mentor here. Brian Chesky, the CEO's mentor. I'm the intern. I don't understand the language that was being talked in the hallways or in the conference rooms, this tech lingo that I hadn't grown up with. And frankly, there was a, I was twice the age of the average employee. So I decided, gosh, the only way I'm gonna survive here is to be as much of a curious learner as I am the wise sage. And, and that's what a modern elder is. A modern elder is not like the traditional elder of the past, who is regarded with reverence. The modern elder is all about relevance. And relevance is taking that timeless wisdom, and applying it to modern day problems. But that means you have to actually be a a lifelong learner. Well well, you know, first off, in your original boutique hotel chain, every time I went to San Francisco for the past 2 decades, San Francisco is known for its boutique hotels. I'm sure I've stayed in, like, several of your hotels because there was always something special about the boutiqueness, the the the modernity of, certain hotels in San Francisco. That doesn't happen in any other city. So congratulations on that. And and Brian Chesky obviously made the right choice just on the surface because you knew hospitality, and that's what Airbnb kind of needed to make that transition. How much do you feel when you first got there, did you feel like, I I don't necessarily agree with you that you didn't have any digital intelligence. Like, everybody just naturally had it, but I do agree that probably you needed to show them you were listening rather than just lording over them with your ideas. There's a great old saying, knowledge speaks, but wisdom listens. And, I was giving a talk, in Utah recently with the summit series folks, and there there's a I was supposed to be giving a talk on wisdom to mostly people who are 20, 25 years younger than me. I'm 58 as of October. What the hell? You're 58? Yeah. Yeah. Yeah. So I as I was going in to give my talk, there's a guy with an owl in front. Like, okay. You know, I've never met an owl, and he's got the owl on his arm. And so I got put the owl on my arm. And I said, so why is the owl the wisest animal or bird in the forest? And he says, because it has the most acute listening skills. It can hear everything. And so that really is an interesting analogy to the elder, the wise elder. The wise elder, the modern elder is somebody who's a great listener. And they're not just listening to the story. They're listening for the story. One of the things that you mentioned in the book, and I thought that was an interesting distinction. Because there's always Yeah. A good story has layers, and there's a story within the story. The I think the wiser you are, the more you're able to see what's beyond the surface. And, what happened with me at Airbnb is I was talking with all these young people, and they'd be telling me their story about why they and their manager aren't getting along, or this or that. And what I was really listening for is what's beneath the surface, maybe the theme or the thread that's sort of unified here. And then not with the intent of sort of giving them a gotcha, but more just sort of actually asking questions. I think the elder of the past was all about the answers, but damn, Google has all the answers today. So I don't even I don't need to have all the answers. I though could use if I could be the one who gives the catalytic questions that are that feel really nuanced and perfect for the person I'm giving it to, then I think I have served my role as a modern elder. What what was an example early on where you finally, felt like, oh, okay. My role as an elder is this is what's happening to me. Like, I'm I'm actually providing some value. And not like in a macro way, like, where you're helping all of Airbnb, but just in an in interpersonal way where you're helping an employee there. Well, or actually, it happened the the thing that popped in my mind first when you said that was I was in a meeting, and lots of people in meetings try to show how smart they are. And everybody's, especially in a young company, they're sort of like, who's the smartest in the room? And I realized I, had a bunch of questions, but they weren't the normal questions, Like what and how questions, which are sort of optimization questions. They're more like why and what if questions. Which are the kind of questions that a 4 year old asks. But this was specific to our Airbnb peer to peer review system. And our peer to peer review system at Airbnb is much better than say the hotel, you know, online surveys that nobody fills out. So we have a better system. But five and a half years ago when I joined, there were some flaws in it. So I asked a bunch of why and what if questions that were, you know, in the Airbnb world, some of them are blasphemous. Like, well, why do we have hosts review guests? Hotels don't do that. So I wanted to understand that. But some of the questions I asked, and ultimately on that one, I was like, yeah, I think it's a good idea. But some of the questions I asked, like, why is it that we don't think there's retribution happening? And like if a guest has a bad experience with a host, have you seen the data? It shows that on the 30th day, which is the last day that people could actually give a review, there's this huge spike up in reviews on the last day. And they're 50% negative. Whereas normally, they're like 80% positive or 90% positive. So people are waiting till the very last moment to actually put the review up because they're worried about retribution. We need to change the system. And so we bay basically, I said, let's make remake the peer to peer review system, which and was at first thinking like, wow. That's something we're not gonna touch. It's been it's it's so the community is sort of likes it the way it is, but we made 2 or 3 major and fundamental changes to it and made it better. What what did you change? Because because, again, just as as background, I lived for about 3 or 4 years only in Airbnb. Yeah. So I I became very familiar with the Airbnb system. Yeah. So so so a couple examples. One example on the one as a riffing on just what I said was, instead of having 30 days to review, but if you on the 7th day you put it up, it immediately posts. We made it such that you had 14 days to review, and yours didn't post until the other person put theirs up, or 14 days went by. So in essence, we didn't, we took away the retribution problem, because if you're the guest reviewing a host, and it's not a good review, you're actually giving that review, not so that the host can see it, and then have them write a bad review about you as well. So that was one thing. We also created private feedback. The ability for a host to give guests, or a guest to give host feedback that Airbnb doesn't see. And we also gave an opportunity for the guest and the host to give private feedback to Airbnb about the host or guest, that that didn't exist before. And then we just started actually aggregating information better. So it helped us to do a better job of determining search ranking based upon the reviews. You know, I don't know how much of this was your like, just your presence at Airbnb might have helped their overall culture of hospitality. You know, you you being there and representing hospitality probably sent the message to all the employees. Hey. This is gonna be an internal focus. And and I remember, this was probably 2015. Airbnb was very you know, I I I wouldn't there was one time I couldn't find an Airbnb, and my old Airbnb was up. And I had to move, and I had no place to go. And I remember the employees were were very concerned with finding me an Airbnb. They would call hosts. Yeah. And then one employee, his shift was over, so the next employee took over. And they found me a place to stay. Like, it was Yeah. I could rely on them for to to live to to find a place to live. And then the other thing that happened was the host I was a a a a guest. You know, I was never a host. I was always a guest. And but the host and the guest were in this kind of weird, symbiosis where we were afraid of Airbnb equally. So if I had a problem or the host had a problem, we'd work really hard Great. To figure it out. And then we'd bring in the Airbnb Yeah. Person to figure to to make the whatever adjustments they need to make, like money transfer back and forth. But we were all so afraid. Like, I always made sure I'd go with hosts who this was their business Yeah. Because they didn't want their reputation Yeah. Tarnished. And I and as someone who was a perpetual guest, I didn't want my reputation tarnished. Right. So we'd worked really hard to to figure it out. Well, lots of the programs that Airbnb has I mean, you know, I've I've been there for 5 and a half years, the last year and a half in a consulting role, but a lot of the programs we put in place, were things that we just brainchilds that, you know, I had along the way, along with my team. And then some of them are things we inherited that just needed a boost. There was a program called the super host program that existed when I arrived, but there were only 200 of them in the world, and they hadn't added any added any for about a year and a half. And they were thinking about getting rid of the program. So there are now 700,000 super hosts around the world, and we used it as a metric for success and quality, and how you could have a better assurance that that particular listing and that host was actually good at what they did. And it also became something that helped incentivize the host community to step it up a little bit. So long story short is business is often about psychology, and it's all about understanding people. And I learned along the way at Airbnb that to be a modern elder meant to intern publicly and mentor privately. And you discussed that quite a bit in the book with some fascinating stories. Yeah, whether it was Brian who didn't need me interrupting him in the middle of the meeting as the CEO, having me say, you know, here's how that you should run your meeting. No. I mean, if I was gonna give Brian feedback about a meeting, I would give that privately. But I would also give that privately to someone who is a direct report of mine or somebody, who asked for me to be their mentor, I'd make sure that the feedback was private. But I was very comfortable being the person who asked the most questions in a room, and quite often the most naive. And so yeah, maybe I didn't know a lot about digital, but I certainly knew a lot about common sense and business. And and that was the piece that I think was very helpful. What was some of the, kind of, to the side business meeting advice you would give to Brian? Like, when would you notice something in a meeting where you say, you know, maybe you could have done it this way? Well, I mean, the the most obvious examples were when people who are generally introverted but have great things to say aren't encouraged to actually say something. So you end up in meetings often with certain people dominating the meeting who are usually extroverts, usually sort of bigger thinkers who just sort of end up sort of talking for long periods of time. So one of the classic things to do was to say, how are you going to either in a one on one with that person who's too quiet, to encourage them to talk more? Or how do you actually just sort of say have an idea that and pose an idea to the group, and then actually call on that person first. So they have an opportunity to talk. But in some cases, it was actually someone who's brilliant, but needs time to process. So if it's someone who's brilliant, needs time to process, actually tell them what you're gonna go over in the meeting, 4 or 5 days before the meeting. So they've had time to process it. By the time of the meeting, they can actually articulate. Because we all think differently. And so there's some people who actually need time to synthesize their thinking before they actually express it. That's such a great idea. I haven't really thought of that. So let's say, let's say I have a meeting a week from now scheduled, and it's with a bunch of younger people, just hypothetically, or anybody, really. And I could almost it's almost like not quite giving them assignments 4 or 5 days before, but almost asking kind of a gentler way to do it is asking for advice. Like, hey, I need help with this. Maybe this is think about it, and we could discuss it in the meeting coming up. That's right. At least getting people mentally prepared for it. Some people won't need that at all because they're just sort of spontaneous. Others actually appreciate it. And, usually, the more introverted you are, the more likely it is you need that processing time. Another thing I did with Brian is, in one particular time, as we were going into the holiday season, everybody had been working their rear ends off, and the families of these senior leaders hadn't seen them much. And so I said, you got Thanksgiving coming up. It's a great opportunity to send flowers to the spouses of senior leaders in the company. Flowers or a bottle of wine or whatever. And just say thank you to the spouse and the family, not just to, you know, your executive. Because those are the people who are basically suffering through the fact that, you know, you've got us working, you know, 16 hours a day right now. It's so funny, because this is related to what you just said is related to a podcast I had yesterday and a podcast I have later this afternoon. Wow. And, in the podcast yesterday with, Jocko Willink, he he mentioned, there's opinions and facts. The spouse is a fact. So you have to work with the spouse and make sure everybody's happy in the family unit. Yeah. And then, later, talking with Mike Ovitz, well, of course, the the famous, CA agent, And you would see throughout his autobiography, if he was trying to win over Paul Newman, Paul Newman was kind of this abstract entity that he was trying to win over. But Joanne Woodward, Paul Newman's, you know, long standing wife, that was who Mike Ulrichs would really try to win over to to get Paul as a client. I mean, we don't we forget about the fact that there's a persuasion factor with a spouse or with a partner. And every every night, that person's going home. And usually, you know what? There's a we tend to kvetch a lot, you know, when we go home from work. And so the person at home has maybe a little bit of a distorted perspective. Number 1 is the person's coming home and complaining sometimes. And number 2 is the person who works for you is working really long hours, so the people at home aren't seeing much of them. So it's not surprising that sometimes when a senior leader is thinking about leaving, the spouse is saying, Yes, please leave. So I think that was, you know, just a thing I wanted to make sure Brian understood is that actually building that those are a really that's part of the constituency you need to be playing to. That's a really good point because if someone's unhappy, the spouse who doesn't have of of the full range of options in front of them to suggest is just gonna say, well, just quit and find another job. I'll I'm supportive of that. And if the spouse is working, like you say, too many hours, or if the if the leader is working too many hours, the spouse is gonna say, hey. I want more time. Like, I'm unhappy. Yeah. So you have to figure out ways you're unhappy. It reminds me, though, when when I was running my first company, I was in my late twenties and and 30. And my goal I didn't think about spouses, maybe because I didn't have one at the time. But my goal was, I wanted my employees to be able, at night, to call their parents and say, I just had the best day at work. Yes. So that was always my goal. This is why I called my boutique hotel company, joie de vivre. Very few companies in the world actually have a mission statement that's also the name of the company. But joie de vivre in French means joy of life. And so our, our mission was to create opportunities to celebrate the joy of life. 1st for our employees, second for our customers. And that was the premise. And so I think the more you I mean, one of the things that Brian knew way before I joined, that he was just so brilliant at, but I think I helped a little bit, was the culture. How do you create a culture that is, something that people actually are magnetized toward? And culture is so important. Yeah. Particularly today, you know, we have 3.2% unemployment, so people could know they can just leave a job and find something better. So culture has to be is more important than maybe ever before in the past 40 years. Well, I used to say culture eats strategy, for lunch. And and it's the idea there is cultures can be a strategic differentiator for a company. And not all you know, there's not all good or bad cultures. I mean, it depends upon the industry, the the geography, the nature of who your who your employees are. So I wanna ask you about, you know, your reinvention and, you know, the different things you've gone through, including most recently. But, tell me a little, like, what does it mean a personal board of directors that you you mentioned, I think it was Sally Krawcheck's, recommendation who herself has kind of reinvented herself very successfully and has has had so much admirable success in in industry. But what what does it mean, and how does how can I create it? Yeah. I think you having your own personal board of advisors or directors really is just saying, if you could actually have a collection of people who just knew that you counted on them as somebody for sage and direct candidate advice, you would actually, number 1, feel a little bit more solid that you have people in your camp. Number 2 is you don't feel guilty when you do out go out and ask them. And number 3, on certain occasions, you actually might bring them together on a conference call or video call and say, you know, I wanna pose an idea or thought to you as a group. You all don't even know each other, but I'd love to actually have the synthesis of all your great ideas with me in a 90 minute phone call. This is I love this idea because it's almost a a formal way of the of the, kind of personal development saying, you're the average of the 5 people around you. And which is such an it's a cliche, but it's so important, and it's so correct. And you only realize that after years of not having the right 5 people around you. But, like, it's like a formal way of doing it. Like, again, how would how would I go like, I feel like I have that in my life, but how many people make up a personal board of directors? Like, are they your best friends? Are they your just advisers? Well, I would start by saying, don't assume that you're ultimately gonna have them all together. So they they don't have to necessarily, feel you you don't have to feel like they all could get along well at a c**ktail party. I would say, make sure that you have diversity in there. And I'm not just talking about gender or, racial or age or, you know, sexual orientation. I mean, just, cognitive diversity. You want somebody in that group who is a big thinker, not process oriented. And then you need somebody else who's gonna be somewhat sort of like the COO type who is very process minded and probably can actually look at something and say, well, here's the steps you'd need to take. Having those 2 people at at minimum is helpful. Having somebody who is not from the business world or from your career world at all. Like, I love having an artist or a writer as a close friend. I have many of them, partly because they are able to see symbols and metaphors of my life better than my more sort of logically thinking business friends. And sometimes it's the metaphors in your life that are the most powerful, and they're the ones that actually help you to see, wow. I have a friend Vanda, and Vanda is a poetry fairy, which means that she basically goes to parties and she just starts spouting poetry. And, but that sounds sort of weird and fun. And yet as a close friend and sort of on my board of advisors, her ability to just a moment in a moment's notice, understand what I'm going through. And then just through memory, remember a poem from start to finish and read it to me just when I needed to hear it. That's a modern elder. That is when someone has just given you a gift. And, so sometimes I need the literal help. Sometimes I need more of the artistic figurative help. And then there's some some people who are there who are just there only for your own purpose of of just making sure that that you know someone loves you. And it's that's the person who's just gonna support you in whatever you're gonna do. But hopefully, if they're giving some tough love, they're gonna actually give you their point of view. Not for necessarily what's best for your career, but maybe what's best for you. Right. And that I I, you know, I was thinking about your your role or your your definition of yourself as a modern elder at Airbnb. And I was thinking if I was in that position, sometimes you're gonna have to legitimately say to maybe an employee at Airbnb, hey. This might not be the best path for you at Airbnb, being an employee here or or or do being a technologist, or whatever it is. Listen. Candor, you know, not I hate when someone's just sort of telling me what they think I wanna hear. Mhmm. I really appreciate when somebody's direct with me and respectful. You know, that that nice balance of direct and respectful allows me to sometimes hear it when, you know, if it was just direct alone, I might shut down. So, yeah. I had some really tough conversations. I had one woman I actually talked about in the book, Jessica. She was having a terrible relationship with her boss. She was gonna leave the company. And all of a sudden Brian said, hey, we've gotta do this first time Airbnb open. And it was like 4 or 5 months before we were gonna do the first one. We were gonna have 1500 people from 40 40 countries. And I had 4 to 5 months to plan and organize this event while I had a full time job at Airbnb. And so I needed someone. Jessica was basically on the path of leaving. And I just told her, you know, this is gonna be your last chance to sort of make a mark here. And, you're a creative spark. You love our host community. Let's actually take you off the ground. And she's like a little wounded bird who had a wing that was broken. And so I just gave her the opportunity to be sort of my right hand person on this. And she did a hell of a job. And that led to the Airbnb open going to a 2nd year in Paris. And then you were at the 3rd year with 20,000 people in LA. So from 1500 to 20,000 people, Jessica now having left, she started her own company called The Passion Project. And then now she's becoming a psychotherapist. So I have, in essence, helped her move from Stanford Business School Grad to Airbnb exec, to all of a sudden, you know, her path to becoming a psychotherapist, which is what feels natural. And we all have 3 relationships with our jobs or with our work. It's either a job, a career, or a calling. My role in life is to help people find their calling. You know, I thought about this in the context of money. So this is a I'm gonna make a a weird analogy to what you just said. People always ask, what number do I need to retire? Which is almost an antiquated question because retirement's starting to become an antiquated word. Yeah. You know, you you kinda have to keep active your your whole life. But I understand it. What does financial freedom mean? And so let's just hypothetically say you need 10,000,000 because you'll make 4% every year after taxes conservatively, so you could live a nice life with a great life with 400,000 a year. So let's just make up that number. But the flip side is, if you love what you're doing and you don't have 10,000,000 but you're making 400,000 a year, it's as if, virtually, you have 10,000,000. It's as if your your virtual net worth is 10,000,000 because you would be doing this anyway, and you're making this income stream of 400,000 a year, which is, like, if you were a public company, you'd be worth 10,000,000. Yes. So so you can look at it both ways. And and the more you love what you do, the higher your virtual net worth, giving you the freedom you want. Yeah. And so in real in some sense, helping somebody find their calling brings them closer to financial freedom even if their income doesn't change. Yeah. You know, the thing it does, it puts them in the the flow zone such that they can, you know, tap into that river that, Mihaly Csikszentmihalyi wrote about in Flow, his book, famous book. And You're the first person I've ever heard to say his name right. He calls himself Mike. You had to practice that. Here's no well, he and his wife invited me to their Montana cabin for 3 or 4 days a few years ago when I was writing another book called Emotional Equations. And I was writing a chapter in flow, and he said, come on up. We'll spend 3 or 4 days together. And we'll just muse. We'll just go for hikes. I mean, it was amazing. So Oh my god. I wanna do that. Yeah. So long story short is getting into that flow state is frankly almost hypnotic. And you do it. You do it when you're on stage. You do it when you're doing a podcast. You get into that place where all of a sudden it feels like the the heavens and and the cosmic consciousness is just flowing through you. And you say things that are not necessarily planned, but it just came through you. And that well, it's not saying. It's also doing things. There's an element of when you're lined up with that. And I I I, you know, that sounds awfully new age and very Californian. No. But also but the science of flow is acknowledged now. It's huge. And it and the thing that a lot of people don't know about this is that, actually, to get into the right flow zone, you have to actually have a com a combination of being at ease, but also being a little stressed. So flow does not happen when you're actually just sort of mailing it in, doing the thing you know really well. Flow happens actually when you're sort of pushing yourself at that sort of level of stress zone, so that you're in between stress and boredom. And so a lot of people don't know that. And they they think, okay. Well, flow zone is just like doing what sort of, like, natural no. What's natural natural alone is gonna actually get you to a place where you won't you will not push yourself. Yeah. It it's it's so interesting because I can think of of 2 examples. Like, a a classic example would be computer programming. Many computer programmers who are great and there's a big difference between great and good computer programmers. But a great computer programmer will slip into flow not because they're so good at computer programming, but because there's a problem that they can't quite solve yet. So 9 hours later, they look up from their screen and, you know, they have the best code in the world and they've solved it. But it's but they were they're like, what? 9 hours just happened? You know, and similar thing for, like, like a great chess player, say. But where I've experienced it recently is like you like, I did an hour of stand up comedy last week, at at at this very club that we're we're sitting in. And suddenly, it's like, you're right. I had already had a lot of experience and been practicing and preparing so much, but then there's still that stress. Like, oh my gosh, an hour. What if I forget things? What if I run out of material? And just in the that combination of I've worked so hard, and I know this, but that stress of, like, there's an audience paying to see me. Things just come out, like, the right things at the right moment Yeah. If you're in that state of flow. And it it really does happen, and it's it's a huge dopamine or oxy something happens to the brain. It's like a wonderful feeling. It it is. And, it it's you know, there's lots of example people go running and they have an endorphin high. There's there's lots of physical effects that can happen in our life that sort of tell you you're on the right path. And, I think getting clear internally you're on the right path is probably one of the most important things for us to figure out in life. Weirdly enough, we don't do a whole lot in in people's upbringing to help people get there. Yeah. Thank you. And so Yeah. We just feed them facts, which they're gonna forget. That's right. And sort of says, here's the standardized tests you have to do well on. And long story short is I love people. And so my experience at Airbnb, in the land of the young, in the land of the algorithms, it was algorithm and people wisdom. And so it was my people wisdom matched with their algorithm that I think allowed the company to go from relatively small startup to what today, what is arguably the most successful hospitality brand in the world. Absolutely. So I have I have one quick question, then I wanna get to your personal reinventions and and how you've found your path and so on, you know, which is an odd thing to say because you're still finding your path, and you're like you say, you're 58 years old. But, oh, I'll tell you I'll tell you one joke, though. Yes. Yes. So because I recently turned 50, and I thought to myself, I don't know. My brain still feels like as young as when I'm 15. Like, I don't feel like I'm 50. And then I realized, you know what? That's total bulls**t. Like, when I was 15 here's the big difference. When I was 15, I would sneak out of home to go to parties. And now that I'm 50, I sneak out of parties to go home. And it's really true. That's kind of like a big difference, and there's a lot of layers underneath that. But there's a huge difference between 5th. 50 is the new 50. I no longer allow people to say, oh, you don't seem 50. Yeah. I'm 50 Yeah. And proud. But, when you you were working with, you know, Brian Chesky, Joe Gebbia, the, you know, the founders of of Airbnb. And between 2013 and now, they've personally seen their own fortunes rise. I mean, they're Yeah. They're multibillionaires. When you started working for them, they knew that they that there was success coming, but hadn't yet happened. How did you see yourself as an elder guiding them? You know, people always say money doesn't necessarily make you a better person. It magnifies what's already inside you, which needs a lot of guidance as you get there. How did you see yourself also as as a an elder, a mentor, guiding them as they dealt with the success so they can keep on being the leaders that they are? Well, so I I think you spend the first half of your life accumulating, and we spend the second half of our life editing. And so one of the things that I think, is striking about an elder is their ability to have precision about what's important and to be able sorta it's not it's not a mathematical or an arithmetic equation. It's a division equation. Meaning, knowledge, you can knowledge can be plus plus plus plus. Wisdom is a division equation, so you get down to what's the essence and what's most important. So I think one of the things I really Maybe maybe explain that a little bit. Yeah. So it means, being wise is be able to see a lot of things and then be able to see the theme or the thread, or the thing that actually is most important. And to help actually put the blinders on when you need to do that. Let let me use an example to explain. So when I joined Airbnb, we had 30 strategic initiatives in 2013. I was like, who can ever remember all of that? So I asked Brian, you know, are we, are you wedded to these? And he says, no. I said, okay, so let's have 4 next year. Let's have only 4. And let's go to New York from San Francisco. We'll take our dozen senior leaders. I'll lead a 4 day retreat, 3 or 4 day to retreat there to actually figure out what our strategic initiatives are for the year. And let's have all 12 people on the on the team bring their favorites. And we ended up having 23 of them. And let's then make a conscious decision that we're gonna actually edit it down to just the ones that are most important. So I think one of the things that I was able to do, and again, let's start by saying that the the 3 founders are brilliant and have growth mindset. You know? So they're always interested in learning. But Which is key. And but and growth mindset refers to, I Carol Dweck. Carol Dweck's mindset. Exactly. And, Excellent book. A book I gave to Brian, and and Brian sort of looked at it and say, yeah. This is the way we wanna be as a company. But the problem for for a company that's growing that quickly and also in the sharing economy is we were getting business proposals to have us go into sharing of all kinds of things. Because the sharing economy has gone in all kinds of different directions. And my, you know, my counsel to Brian and Brian was on the same page was, let's just stay in travel. Let let there's an opportunity for us to grow into a super brand of travel. And, like, just let's focus on that. And I think so to answer your question, part of the idea of helping them for the company was to actually help them to make sure let's edit what we do so that we're focused on what we can do well. That means, frankly, we are a distributor, not a manufacturer. And just if you think about it, just take a step back. It's like Airbnb is a is a an incredibly popular website that distributes something. We don't actually go out and build things. Now we've been asked to do everything from building hotels, to designing all kinds of interesting things. And because Joe and and Brian are both designers from Rhode Island School of Design, they like the idea of that. But if we can come back to what we do well, we're a distribution company, and we're a brand that people like because it stands for something, which is to belong anywhere. So long story short is I think the idea of an an elder or modern elder is that they are able to help you see the essence of what's important. And then based upon that, make decisions using that editing function. I mean, Steve Jobs was famous for saying, you know, one of his best qualities was the ability to say no. And that's a really important quality for young people who have lots of options. And so so saying no but I also feel like, you know, a lot of people in that accumulation stage, they're focused on growth, growth, growth, you know, increasing knowledge to increase growth, to wipe out competitors, to accumulate. I'm not saying this in a bad way. That's just a a natural progression, particularly for for people who are as successful as the founders of Airbnb. At some point, there I feel like an elder comes in, or you learn from experience. What are your core values beyond accumulation? And I feel correct me if I'm wrong. Doubt. You know, I mean, we were a disruptor. So it's and so we were lumped in with, with Uber a lot. And so there are lots of opportunities for us to do strategic partnerships with Uber, which we didn't do. And, there are lots of opportunities for us to be compared with Uber. And we do our best we do our best not to sort of say anything good or bad about Uber. But what we really wanted to make sure that we could have the founders understand is if we're gonna be a disruptor in the hospitality business, we better be hospitable. And so what that meant was let's be a friendly disruptor. Let's actually have a brand that actually stands for something. Let's actually be more proactive about how we give back and we do social good out there. Let's do things. One of the things I said to Brian is, let's invite the CEOs of Hilton and Marriott and Starwood here with their senior executives, and let's do a day and a half for each one of them, each of those companies, teaching them about data science and millennial travel habits. And, what is home sharing? And we did that. You mentioned it in the book, and I was wondering And it's crazy. The idea. No, well, you know what? Here's the part that was interesting. It's like, we're gonna be the villain, so we're the disruptor. But it's harder for them to hate us if we've actually been generous in in our process. And we haven't. You know, Arnie Sorensen, CEO of Marriott is on the back of the cover of that book, endorsing the book. Now that's sort of surprising that Marriott the Marriott CEO is endorsing a book about Airbnb. But yes, have we over time, there's a great Gandhi quote that's in the book. I said it the 1st day I started on the job. Gandhi supposedly said about the British back in the 1930s, first they ignore you, then they ridicule you, then they fight you, and then you win. And that is the path of the cycle for all of these people we were disrupting, landlords, hoteliers, corporate travel managers, convention meeting planners, destination marketing organizations that market cities. In each of those cases, there's initially like, oh, I've never even heard of them or let's just ignore them. And then there's the ridicule and then the fight, and then the win. The fight we've had with the hotel industry, because we have absolutely become more of a competitor. Although I don't think we're in a death match because I think the, the value proposition of hotels and home sharing is moderately different. Our average length of stay I do agree with that. I've realized that. Our average length of stay, you were a guest. Our average length of stay is more than twice as long as a hotel. And that's because we work well for a longer stay, not as well for a shorter stay. And hotels exactly the opposite. They work well for the efficiency of a short stay, not so well if you're gonna spend 3 weeks or 4 weeks in a hotel room, a little box of a room. So, long story short is I think the idea of reaching out to those that we are gonna disrupt in a proactive way and friendly way before they get to the point of actually ridiculing and fighting us is not a bad idea. And it's it's interesting to point out that that's outside the comfort zone of everybody involved. And I think that's always important to do. Yeah. I think the fact that it was contrarian is why I liked it so much. Mhmm. I like being a rebel. But I but at the end of the day, it worked. It absolutely worked. In that, it actually, I think, meant that we had a a line of communication with these companies with these hotel companies. And some of those hotel companies, while we've never announced it and I can't talk about the specifics of it, we came so, so close to some partnerships with those huge hotel brands that would have been off the charts, But they they at the end of the day, they got scared. They, not us, Airbnb, the hotel brands did. In part because they also have an agenda where they're they have to officially lobby against you. And so it's hard for them to do deals with you while they're lobbying legislation state by state. They are franchisee franchisors. So they actually have owners of hotels. They don't own many of their own hotels. Right. So they have owners of hotels who've basically paid them a lot of money, and they don't necessarily want the owner of the hotel doesn't necessarily want, them, you know, collaborating with us. But long the the I think the the whole point of that is just to say, business can be cutthroat. And, you know, but when you're a disruptor, you actually have, almost like the noblesse oblige of actually figuring out how do you take some of the sting out of it. And in my persec from my perspective, it was actually, let's help educate them. Because the more they are educated, frankly, the more they may actually see that we are not as directly competitive as they thought we would be. So so but I wanna know also, like, as you saw the rising fortunes of of Brian, Joe, Hates, the other founder, how did you see them change? You know, were you able to give them personal advice? Like, how do they you know, they're probably I don't I'm just imagining they're buying huge houses and Ferraris. No. They're taking none of that. They're like they're so they're so, you know, modest in terms of their spending habits, you know, for how much they're worth. So that I think and I think I I had some effect on that, but I think a lot of other people did too. I think where I could I was really helpful is helping them to see that, humility. You know, the thing that's unfortunate about Silicon Valley Tech Entrepreneurs is the hubris they needed to go actually raise that money from the venture capitalists was fine in that venue, but then you don't operate your company, nor do you operate me media wise out there in the world with that level of hubris. So I think part of the process of moving from young entrepreneur, which I was at age 26, starting a hotel company, to 52 at age 52 joining Airbnb was going from hubris to humility. Because what happens along the way is you get your your knee skinned a few times. You break your toe. You know, you you you have some failures. How do you learn humility? I think you I think you learn humility because you actually realize you don't know it all. And I think the the challenge with young entrepreneurs who are very successful, straight out of the gates, is they believe it's exclusive because exclusively because of their Midas golden touch. And that's not true. There are a lot of maybe intelligence and a few other things, but that doesn't mean they're perfect. And the process of learning you're not perfect is one of the most important, and tangible skills that a young entrepreneur needs to learn. See, I wish when I had my initial success around the age of 30, I wish I had had a toddler Yeah. Yeah. Telling me that because then I would have avoided 20 years of pain. But, I wanna really ask you about your reinventions. I'm hoping we could push this a few minutes longer than we initially had planned. So so, you know, around the financial crisis, you have been running the this great set of boutique hotels for so long. This was your your domain. You knew it. You experienced the suicides of 6 friends, I guess because the combination of the financial crisis kind of up was an upheaval to many of their dreams, and they didn't know how to reinvent themselves. Well and, also, we you know, we get attached to our identities. And if you are a successful entrepreneur, founder of a company, CEO of a company, and it's going bankrupt, you're going emotionally bankrupt. And it's Yeah. It doesn't have to be that way. And it's not that way for everybody. But for many people, it is. And we get very attached to our name tag that we wear on our chest. And combined with the age, like, did you think, oh my gosh, at 52, I'm selling these boutique hotels, maybe not necessarily as high as I would like, but I I can't take it anymore? Yeah. What at 52, did you feel like, oh my Bill Clinton was president at 42. What am I gonna do now at 52? Yeah. I was Barack Obama was president, and he's younger than me. There's a great quote from the intern, from Robert Gennaro. He says, musicians don't retire. They quit when there's no more music left inside of them. So at 52, I knew there was music inside of me. How'd you know? I knew it because I knew it. I felt the energy. I felt the energy that I was curious still. I still had this curiosity about I actually was Frank, I'll be honest, I was burned out, the hotel industry. I was bummed out because more and more institutional money was coming into real estate that sort of saw the hospitality business as a small h, big b, hospitality business. Whereas historically, the hospitality business had been a big H, small B, and had been like people get into hospitality because they like to make people feel good. But when you're judged on your quarterly earnings by a public REIT that owns your hotel, you make short term decisions. And sometimes those short term decisions are not great for your employees or your customers, but they make more money. And that was a frustrating thing. So I knew I still had a lot of curiosity and creativity toward hospitality, but I felt like the whole, industry had changed to become so institutional. So it was interesting when Brian came to me on our first meeting and said, how would you like to democratize hospitality? And I said, wow. That sounds pretty good. It could use that. And, you know, now more recently, you you you've transitioned from, you know, a full time at Airbnb to being a strategic adviser. Like, what led to that? What's your you know, you're reinventing again at at age 58. You're just as young as ever. Yeah. What's Well, what what's, what's up with this is I I 70 hours a week was not gonna last forever. I loved it, and I still love the team, and I'm still very involved. But I wanted to get some time back in my life. It gave me the time to go down to Baja, California, a sewer, like an hour North of Cabo San Lucas, which is where I live half the time. And to start writing the book and learning how to surf. At age 56, 57, I started learning how to surf, which was great. But more than anything, what I started to do is interview a lot of people who are in midlife. One of the things that's interesting about midlife is, until, like, in the year 2 year in the year 1900, longevity in the US was 47. But by the year 2000, it was 77. So we added 3 decades of life to the average person in 1 century. By 1965, we had something called midlife crisis, which is coined by a psychologist. But it's 53 years later from 1965, and we've done nothing to actually solve the crisis. And midlife is now not just 20 years long, from 45 to 65. I would argue it's 40 years long. It's a marathon that goes from 35 to 75. Because many people in many industries, especially in technology, start feeling a little bit irrelevant in their mid thirties. And a lot of people who are gonna do a 100 are gonna work till their mid seventies. So I'm sitting on the beach, or I'm not sitting on the beach, I'm sitting on my deck above the beach, writing my book, interviewing people, hearing a lot of anxiety and bewilderment from these people who are having a midlife crisis. And I said, why is it that in every other time of transition in our lives, whether it's puberty or it's going from adolescence to adulthood, or it's getting married, or it's having a baby, or it's dying, we have rights of passage and rituals and celebrations. But we have nothing in midlife. We have nothing that brings people together. And so that's what led me to say, I am a boutique hotelier at heart, but I also am sort of a personal growth person. And I've been on the board of the Esalen Institute at Big Sur for 8 years. I've been a teacher there for 12 years. What if I created a the first midlife wisdom school in the world where people mind their mastery? We'll call it the modern elder academy. I'll buy all of the land and homes nearby me. So I've got 3 acres on the beach, and we'll try it on a beta basis for the first half of twenty eighteen 153 people going through either week long or 2 week long programs. We did all of that. It was such a transcendent transformational experience for people that were open to the public now, starting this fall in November, we're sold out for the first 4 workshops. And it's a social enterprise, so 50% of the people are on scholarship because I loved seeing the social worker walk down to the beach and go walking on the beach to have a heart to heart with the investment banker because they had something to teach each other. And, potentially, like, in nowadays, they could even switch jobs. They might be able to. Because and I think people, like, I go through this. Like, if you're above 50, can you truly be great at something again? Like, when you're 20, you have the time and energy and passion to be great at something, whatever it is. But at 50, there's there's doubt that creeps in. Like, am I gonna really wait till 70 to be great at this thing I love? But what I realize is you could bring in you could borrow from the 10000 hours you use getting great at something else Yeah. To to get good. You don't need 10000 hours anymore to get good at the next thing. Well, you may have actually you may have built a skill or mined your the mining of your mastery allows you to see something you didn't know. Mhmm. The mining of your mastery. Mike Riley, good friend of mine, went to college with him. His father was the head of the president of the PGA, professional golfers association. He's Mike actually was a golfer at Stanford, graduated at age 22, 23, went to work for 20 years with IMG, big sports management company. He became an agent for famous golfers. He, in essence, was helping golfers in their forties figure out, what do you do once you're just gonna stop golfing? You're gonna license your name, it's on clothes, you're gonna design golf courses, you're gonna give lectures, write books, whatever. He got fired at age 43 because, the founders of his company, who is his mentor, died. It got sold to a private equity firm. And Mike was one of the more, you know, higher paid people there. Because he was, you know, managing the live the careers of many golfers. It took him a decade to finally figure out what his mastery was. He thought his mastery was golf. And so if a year after, you know, being laid off and losing his job, he went to sports management school to go become a masters in sports management and to teach. But he realized he didn't love sports. He just he thought he just loved golf. And yet the only place he could go do the job he had was at IMG, and they're working about hiring back. He finally realized what he was great at was helping people in midlife golfers, figure out their options of what's next for them. And he ended up becoming now the CEO of UC Berkeley Executive Education. And executive education is basically people in their 30s 40s 50s remaking themselves. And so the mastery that you thought you had, in his case, he thought, I just know everything about golf or maybe everything about sports management. No. Actually, what he knew was midlife career counseling. Yeah. He he meta he meta skilled the micro skill he had mastered. So a lot of us don't see that. And so and in midlife, what are the where do you go to learn that? So that that's the that's the point. And if we're gonna have to reinvent ourselves over and over again as the as the future gets more and more like, change is happening faster and faster. So you're gonna actually have to evolve career wise more quickly than we have in the past. You know, I I wrote a book called Reinvent Yourself. Like, reinvention has been such an important part of my life, which is why I mean, your book again, I'll say, wiz titles, Wisdom at Work, The Making of Modern Elder. I've read it once. I've skimmed it a second time. I'm definitely gonna reread it fully a second time, as you suggest, and probably a third time because I think it's it's so valuable, not just for for elders, but for people beginning their path in life to to to hear your experience and see that there's many possible directions and and possible ways that wisdom could embrace knowledge even at an early age. But one of the most valuable things I found in the book was the appendix, which which relies on you reading the whole book. But No. It doesn't. You could go straight to the appendix. The appendix was great. I've never saw seen an appendix like this. It's like you basically just list your your favorite things, and they're all so valuable. Like, you know, your favorite books. I've I've read many of them. Some of them in podcast guests already. Your favorite films. I love The Intern. Jiro Dreams of Sushi or Hero Dreams of Sushi is one of my my favorite documentaries. The best exotic Marigold Hotel, The Curious Case of Benjamin Button. But the first quote you have in one of your favorite quotes, this James Baldwin is probably my favorite author of all time, and he I'll just say the beginning of his quote. Any real change implies the breakup of the world as one has always known it, the loss of all that gave one identity, the end of safety. And at such a moment, unable to see and not daring to imagine what the future will now bring forth, one clings to what one knew or thought one knew to what one possessed or dreamed that one possessed. And it just go and it goes on. And it's, you know, such a beautiful quote that we all like, he was such an incredible artist, but he too left the country. He dealt with his sexuality, his race. He had to deal with so many changes and reinventions in his life and and the wisdom that came with it. But anyway, Chip, great book, Wisdom at Work, The Making of a Modern Elder. I'd love to help in in your your, you know, wisdom. Maybe you can be guest faculty. I mean, like, you you know, for a place where people are reinventing themselves, you are you would be an amazing faculty member. Come on down. It's it's just We'll teach you to surf. I I I I wanna learn to surf, and it's been such an amazing ride for me whenever I've begun the next reinvention. For instance, now I don't live in Airbnbs. I live in an apartment. For the first time in my life, I had to move into an apartment at the age of 50, and, it's it's it's it's always a ride. It doesn't stop. Yeah. You know, I think if if there's one thing to be learned from all of this is to be continue to be curious because, you know, that curiosity is a woman recently said to me, she said, I don't care the age of the person I'm interviewing. She's an executive recruiter. Because if they've got curiosity and engagement, the wrinkles fade away. And it's true. Your energy has a lot to do with how people read you. And so the fact that I can be as much of an intern as I am a mentor, in an environment where I was twice the age of everybody, I think people sort of forgot that I was the age of their parents. You know, you should, you should find internships for 50 year olds. We do. Like like, We had the we had the senior interns at Airbnb, 73 63 years old. They spent the last 5 years on the road on Air Airbnbs, and they did a 10 week internship as the senior interns at Airbnb a year ago. I bet that was an amazing experience. And we we interviewed recently, Joe Moglia, who was, the CEO of Ameritrade. Really built it up to be, the multibillion dollar company it is. And he left CEO being CEO of Ameritrade to be an intern coach intern to the coach at the University of Nebraska. Oh, wow. And now he's the coach of the Coastal Carolinas. I don't know football at all, but he basically, like, at the age of 70 or in his sixties, became an intern. I love that. And then another thing that happened recently is, Jesse Itzler, who's written some excellent books, and he's married to Sara Blakely, the founder of Spanx. He said to me, oh, you should come down to Atlanta. Be an intern for Sara for a week. And, I think it's a great It's I mean, it it speaks very much to this reinventing. I mean, the you can't reinvent yourself unless you actually stick your toe in the water. And one of the ways to to understand whether you like it or not is to actually go intern. So so, final thing. One one more minute. I I always like to give you suggestions. Last time, I gave you my 10 ideas for Airbnb. I have I have 2 ideas Yes. For Airbnb. One is a lot of people look at Airbnb as entrepreneurs and question, okay. How can this be a road to entrepreneurship for me? So, I almost think Airbnb should create, like, an entrepreneur university Mhmm. For people who wanna Mhmm. Be part of the ecosystem. Yeah. Like Yep. You know, you know, Airbnb really is a a platform. Some people have extra extra inventory of empty rooms, and some people want access to those empty rooms. And Airbnb is the trusted platform in the middle. But how can entrepreneurs make use of that trusted app platform by you know, and and understanding the laws and regulations around that and and so on? So that's idea number 1. Idea number 2, in media, media is such an important way now for for companies to brand themselves as opposed to sort of mass branding that reaches nobody. Any website that has a lot of traffic could could potentially be also a media empire or at least a media creator. Yeah. There could be shows, you know, hey. I'm gonna look at 3 Airbnbs, luxury, middle, you know Mhmm. The the lowest saving money, everything. And every show, I go or somebody goes around and stays in all 3. Yeah. Yeah. Yeah. And that's like a fun show. And you have the traffic. That show would get advertisers and and millions of viewers a week, and and you could even pay to it for it to be over the set top box. You are a psychic. Alright. These things are these both of these things you're saying are in a different form, in the process of happening. So yes. As what happened last time. Yeah. No, Airbnb, the challenge with Airbnb is the editing process of like, what can we do and what can't we do? I understand. Yeah. But the second idea you just said is an idea that Brian really likes a lot. Because, you know, Uber has is doing a Spike Lee series, like, on the app. It's just it's any any site now. You don't have to be a TV channel. Any site can create content Studio. To have the audience. It's an Airbnb studio. So, again, Chip Conley, wisdom at work, the making of Modern Elder. You've certainly been a Modern Elder to me whether you know it or not, and it's been a pleasure these past few years getting to know you. And I'm so happy you came on the podcast again. Thank you so much. Thank you, and I can't wait to see you on stage. Excellent. Good. Alright. Great. Thank you guys. That was so much fun. Thank you.
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