#33: Chip Conley, Founder at Modern Elder Academy — Using regret as fuel; how and why founders ne...

Welcome, and I'm thrilled to have the legendary Chip Conley on the podcast today. Chip is the founder and CEO of Joie de Vivre Hotels, a boutique hotel company which he ran for 22 years before he sold it. He's also the author of 5 books. The most recent one was Wisdom at Work. And Chip was an executive at Airbnb and what he calls a menturn, an intern and a mentor to Brian Chesky, the founder of Airbnb. A few years ago, Chip had an aha moment and opened up Modern Elder Academy, MEA, a midlife wisdom school. MEA is based in Baja, but they're now opening up a new campus in Santa Fe, New Mexico. We had an incredible conversation. Chip talks about his near-death experience and how that shifted his identity profoundly, and also why it's so important for founders to learn to shift their own identities as they and their companies change and how to do that. We talked about how Chip ended up being a mentor and an intern to Brian Chesky, what struggles he had when he first started at Airbnb, and what he learned from Brian, from Gavin Newcomb, and from the other people that he's mentored over the years. We discussed how entrepreneurs can use regret as the raw material for the future and to fuel you, how to manage people older than you, and his favorite interview question. This is an incredible interview and you're gonna learn so much. So please enjoy my wonderful conversation with Chip Conley. Chip, welcome to the show. It's so great to have you.

Alisa, I'm honored to be with you.

I'm so excited. And you know, I have a, I'm gonna give a little bit of a, of an opener here because, um, this is my podcast. It's called From Startup to Grownup and it comes from my book, which is called From Startup to Grownup. And you are part of that genesis story because I went to, I was fortunate enough, we, we met, uh, a couple couple years ago, and I wrote about you for Forbes, and you mentioned this Modern Elder Academy, and I thought, well, I'm gonna go to that. And I brought my boyfriend, so the two of us went in January 2020. That's like this fateful— before everything happened. And we— through that week, I have to really tell you, I got over a lot of my internal identity issues, and I was able— from that was like the genesis of my ability to write my book. And so I really want to say thank you, and thanks to your process at Modern Elder Academy. I don't consider myself elderly, but nonetheless, there I was at Modern Elder Academy. And part of it was we did—

it's the Modern Elder Academy. But yes, exactly.

And we're definitely going to talk about it, but this core, core, core, um, exercise you do, I'd love you to talk about, which is called the identity cleanse. That really helped me in kind of getting out of my own way to write my book. Chip, could you talk about the identity cleanse and why that's so important?

Yeah. So, let's start by just talking about what is an identity. An identity is a way of seeing oneself and a way of the world seeing us that could be sort of an archetype. There's an archetype element to it, but it often has something to do with the roles we've had. So, over the course of our life, we pick up identities. I'm a student. I'm a progressive politically. I am a mother, et cetera. And so, there are these identities we pick up. What's interesting around midlife is that we have picked up so many damn identities and not necessarily discarded any that by the time we get to our 40s or maybe our 50s and definitely maybe our 60s if we haven't cleansed, we're awash in identities and many of them are like affixed, like a Band-Aid to our skin and we're scared to pull it off. So, part of what we try to help people do at MEA, and let me give you another little story, is that I was a founder and CEO of a boutique hotel company called Joie de Vivre for 24 years. It was my identity at age 26. It was how I I basically saw myself in the world, how I prided myself in the world, how I was admired in the world. And then I sold the company and I was a bit like, oh, well, where did that identity go? And I felt a bit rudderless. So, what we try to do at MEA is to help people to see that their identities can evolve over time and that it might be time to cleanse yourself of certain identities. So, one of the exercises we do before people actually arrive is we actually ask people to go to some of their friends. Ask them, what are your strengths? What are your weaknesses? And what are the identities that we seem to inhabit really well? And what are some of the identities that maybe don't suit us very well? It's like having a bad suit or shoes that are just a size or two too small or too big. And that homework people do in advance, then they arrive and we start to do that within the first 24 hours. A deep dive into what are the identities we're ready to let go of? What are the mindsets that aren't serving us anymore? Am I the caretaker? Am I always the caretaker? I'm always caretaking everybody else but never myself. Or I am the CEO of this company, and then all of a sudden, I'm not. So, we help people to understand that, number one, they are more than the collection of their identities. There's more to them than just the identity. Number 2 is you can actually— you have choices of what identities you can pick up in the future, especially if you start to actually let go of some of your identities. And number 3 is, at the end of the day, you're not the only one going through this. There are a lot of other people in the midst of an identity cleanse and maybe a wardrobe change, so to speak, as well.

Yeah, I love everything you just said. I mean, I especially love the idea of that, getting that input from others, because they're an input into your identity. You have your own experience on the inside, and then other people kind of show you who you are in their eyes. I know for me, something you didn't sort of hit on is also this identity you hold about whether or not you have it in you. So for me, it was like, uh-oh, I don't have it in me to write a book. And that's what I had to kind of let go of in that very powerful exercise. But something else you said is so important is that all the founders that I deal with, all the entrepreneurs I've ever coached, they they go through their own journey of identity, like having to let go of the early-day founder and CEO when you were just 10 people in a room together to take on the CEO of a 1,000-person company or 5,000-person company. And then to your point, when you sell the company or when you, you know, some event happens with the company, on the one hand, that's great, but on the other hand, it leaves you without your identity. So, I'd love you to talk a little more about how you think that relates to founders and how you personally experienced that.

Well, let's start with how I experienced it. The good news for me, so when it came to Joie de Vivre, the company I'd started and was CEO for a long time, 22 years into it, I had a flatline experience. I had a bacterial infection, a septic leg, broken ankle, and was put on an antibiotic and I was allergic to the antibiotic. And so, after giving a speech, I went flatline, I went unconscious, and then I actually died and the paramedics had to bring me back to life. So, I had the great fortune of that divine intervention where I could actually see like, oh, at 47 years old, I might have died. And it helped me to get comfortable with the question of, am I living my life today the way I want to live my life the rest of my life? And I think the answer I came to was like, no, actually, I want to change something. I really don't want to run this company anymore. I knew it, but I didn't think I had any choices. I felt like I was in a jail cell, that this is the only thing, the confining identity of Chip, the founder and CEO of Joie de Vivre. It felt incredibly beautiful for a long time, and then it felt really confining. So, I had 2 years to prepare for the fact that I was going to sell the company mentally because I didn't tell all of my employees, "Oh, I'm going to go sell the company now." It was more like, okay, I told a small collection of people, everybody had to be confidential about it. And I had some time to prepare for it, which was great because we'd need that. Because generally speaking, especially if you're in a situation where you are so focused on satisfying your investors' needs, satisfying your employees' needs, you don't have any time to sort of sort through, okay, what's this going to mean for me? And if I— What are my habits that I do every day associated with this job that I don't need to do anymore? And how lost am I going to feel? So, as I move from my story, which was actually a good story because by the time it was announced that I was selling or we were selling the company, I had moved on. I truly had. Now, then I had to deal with the issue of like, oh my God, everybody's definition of me was based upon that. And that was hard. But how did you handle that?

How did you handle that, Chip? That side is hard.

Well, I mean, first of all, it's like so many things. As you know, I'm gay. And so, if you come out— I came out at age 22 in 1983 at a time when it was like, wow, not exactly a great thing to come out as a Stanford MBA around this topic. It was very taboo. But as is true for that, if you're comfortable in your own skin and you're coming out, coming out with whatever, then people actually see that I feel energetically whole and seemingly confident about what's going on, then they get a little bit less worried. So, when it came to people saying, "Oh, my God, you sold a company," and they could see that there was a relief, a tranquility, and also an excitement for what's next, yes, some people had a hard time with it, especially those in the company who knew, okay, there's a new owner here. And I had to deal with that and I had to be very responsible about that. But for people outside of that who sort of said, "Oh, man, you were the guy I would go to get my free suite every honeymoon," I'm sorry, "every anniversary for me and my spouse," like, okay, well, if all I've been is that transaction, then I thought we were friends, maybe. So, I did have a conversation once with someone like that because I was like, he was really bummed because I got him free massages. I got him the best corner table at a great restaurant that was one of our restaurants. It's like, hey, dude, I am not just your concierge in life. I'm a friend of yours. And I had to say to him, if that's what I've meant to you, then that's disappointing and maybe we need to move on. And he said, you know what? You're right. I don't want to move on. I love you. But I guess I was going immediately to my own selfish needs around what you've served in my life, but you've served a lot more. And we had a really great conversation as a result of that. So, yeah, I mean, the process of learning how to evolve your identity is such a powerful and important one that we actually learn in adolescence. So you think about it, when we go through adolescence, we're going through a lot of identity transitions, bodily hormonal transitions. And yet we sort of think that when we become adults that we don't go through transitions. But, of course, we do. And adolescence is a made-up modern word. It didn't exist in 1903. It's a 1904 word. And it now defines an era of life when people are in between childhood and adulthood, your teen years. Well, there's also a new word called middle-essence. Middle-essence is that time in midlife when you are in between the core of adulthood and the early stages of elderhood, not being elderly, but You could be an elder for 30 years where, generally speaking, you're older than the people around you. And yet, we somehow feel like if people are in midlife going through transitions, they're getting the game of life wrong. We get divorced. We have menopause. We have menopause, but you do. Men have andropause. Our parents pass away. We have empty nest syndrome. We change careers. We change where we live. We get divorced. I mean, there's so much. Richness in how life is liminal and it's constantly changing. And yet somehow we try to confine it to say, oh, okay, well, I expect Chip for you to be that identity the rest of your life. It's like, wow, that's a jail sentence.

Yeah, yeah, it really is a jail sentence. I'm just thinking, because Sviband, I had him on the podcast, like my third guest, and he sold his company Contactually to Compass. And one thing he said was he had kind of gotten the hint from other founders that when you sell your company, you're gonna be shockingly left with this void. And so we kind of tried to mentally and emotionally prepare. Do you spe— have specific advice for founders about that particular transition? And, and, and maybe even, by the way, before the transition even of selling, but like, let's say you're an entrepreneur for 10 years or you're, you're the CEO and a founder for 10 years, 15 years. What advice do you have for founders as they go through those tradi— uh, transitions?

First of all, come on down to MEA. That's exactly part of what some people come for. But there's also a great book by Bo Burlingham called Finish Big. Bo is the one who wrote Small Giants, great book, sort of a classic. And Finish Big is a book about what's the mental state, emotional things you need to think about in the process of selling your company and moving to what's next. So, I think one of the most important things is also good advice for people who retire. And a lot of people who are selling their business are not retiring, but I'm going to use that same language, people tend to retire from, not retire to. And it's like, "I'm selling, but what am I moving toward?" And so, if I'm selling my company or if I'm leaving a role I've been in for 20 years, often, we get so wrapped up in that that we don't actually imagine what we're moving toward. As you know, we have Anatomy of Transition. Point of view at MEA, which is there are 3 stages to any transition. There's the ending of something, there's the messy middle, and then there's the beginning of something new. And once you can actually sort of use that frame, and this frame comes from William Bridges and a lot of great people, Bruce Feiler, whose book Life Is in the Transitions is a great book. So, once you understand those 3 stages, there's the ending of something. And ending means you ideally ritualize it in some way. You sort of like say, okay, like, how do I sort of say I'm going to go on that big vacation or I'm going to go to MEA or I'm going to go, I don't know, I'm going to go do a Vipassana silent meditation retreat for 10 days. And there's something that ritualizes the end of something. And then there's the messy middle and the messy middle, as we know, you and I have friends and family members and people like that. The messy middle can be a really dark and gooey time. Think of the cocoon or the chrysalis. Of the caterpillar to butterfly journey, it could be dark and gooey in that time. And what we really need during that time is we need social support, emotional support. We need to actually be open to trying new things and being bad at something, being a beginner at something new. And like, "Okay, I'm going to test this out, see if I like it and if I'm good at it." And so, for someone selling a company, that's a hard one because if you've been the boss, if you've been sort of like your ego has been pumped up by being in charge and in control and now, you're deciding you're going to go learn how to surf at age 50 and you're really bad at it, for some people, they have a fixed mindset. I only like to play games that I can win. And that's what a fixed mindset is. And if you can move to a growth mindset and be open to playing games that you can learn and you don't define success as winning, you define success as learning and exploring, and that is a really important piece of that second phase. And then, the third phase is you literally get to the place where a new beginning is happening. The butterfly is coming out of the chrysalis and you're really embarking on that new thing that you're really excited about. And for me, selling my company was hard. My sister, who had worked with me for 25 years, was still in the company when I sold. She stayed for years afterwards. A lot of senior people left or stayed and then they ultimately left. It was hard on that level. But I also knew that I didn't want to die and I didn't want to die in that job. And so, the fact that Airbnb came along, I had a messy middle that lasted about 2 years and then Airbnb came along.

Can you talk about that?

Yeah. I wrote a blog post recently called Talented People Need Empty Space. And I really do believe that. I think when you are talented and you're motivated, I promise you, that something will emerge. It might not emerge on your timeline. It might take a little longer, but something will emerge. And my experience of that was that I sold my company, Joie de Vivre. I still owned a piece of it. I was executive chair for 16 months afterward. So, I was still actively involved on some level. And then I moved on. I sold the rest of my shares. I was no longer chair. And I was like, okay, During that point, I wrote a book. I spent some time on that. That was my new beginning. So, my new beginning was, "Okay, I love writing books. I love giving speeches." At that point, I'd already written 3 books. I wrote my 4th book during that time. And I was fascinated by festivals. I went out and studied festivals and I created a website called Fest 300, the 300 best festivals in the world. And I went to 36 festivals in 16 countries in 1 year. So, I was active still and passionate, but I really wasn't sure what it was that I was supposed to actually do. How was I supposed to use what I've learned? And it was around that time that I got a call from Brian Chesky, who is the co-founder and CEO of Airbnb. This is 10 years ago, so Airbnb was not a household word. I'd barely heard of them, and I was a hotelier based in the city that Airbnb was based in, San Francisco. He said, I want you to come in and be my mentor. I want you to help us become a hospitality company that's global, et cetera, et cetera, et cetera. And then so at first I was like, okay, I'll do this a little bit on the side. And that was the original intention. And within 3 weeks I was like, oh my God, this is not an on the side kind of thing. This company is growing very quickly and there's not a lot of people in the company with any— there's nobody in the company with any hospitality travel industry background. And there's very few people in the company who actually have ever been an entrepreneur or led a company that's intending to grow to the size that Airbnb ultimately grew to. So, long story short is I strapped myself to the rocket ship and away I went. And it's so liberating when you can move on to the next thing because instead of being full of regret and I should have done this, like I sold my company at the bottom of the Great Recession. It wasn't like I was selling at the top of the market. I was selling at the bottom of the market. So, it was not beautiful timing. And 3 or 4 years after I sold, we were the second-largest boutique hotel company. Kimpton was the largest, and they sold for 30 times more than we sold for. And I was like, "Okay." Yeah, exactly. If I'd waited 4 years, maybe I could have sold for, I don't know, 10 times what I sold for. But I wasn't focused on that because I moved on to the next thing. And that helped because actually, if you're the entrepreneur who's caught up in a regret cycle, oh, man, then you are focused on the past unless you use the regrets as raw material for the future, as wisdom. And that's what I think. Regret is not a bad thing as long as it actually makes you wiser.

Yes. And also, right. And also, it helps steer you kind of back on your right path. I think it's very helpful to use that regret to the extent that you have it. But as you were saying, so Brian Chesky called you and you were gonna be like, "Sure, I'll do a little thing." And suddenly you were working full-time, probably more than full-time.

70 hours a week.

70 hours a week. And I wanna hear about kind of the insight that came out of there that led to your building Modern Elder Academy. But I also, so I wanna ask you kind of two questions, talk about Airbnb in two ways. One thing that I read is that in addition to mentoring Brian, you also kind of— one of the questions everyone was asking you is, how do we build this company that can still scale and still have soul? So, I'm curious about that, how you sort of scale culture and still scale soul because— I know MEA is expanding and I'm curious how you're thinking about that. And then, also maybe talk about how the insight from Airbnb brought you to Modern Elder Academy.

So, let's start by saying that within a month or two after I joined, Brian and Joe Gebbia, one of the other co-founders, separately pulled me aside and said, "Chip, we hired you for your knowledge, but what we really got was your wisdom." It's like, "Oh, okay. That's interesting. I never really thought about that, the difference between knowledge and wisdom." And then, they said, "Chip, you're our modern elder." And I was like, "I don't want to be your modern elder." And then, they said, "Well, a modern elder is someone who's as curious as they are wise. It's like, oh, okay.

Wait, Chip, how did they know that? Like, were they reading that in a book? Like, what do you know?

No, no, no. But yeah, and they didn't— I mean, I just said it succinctly. It was over the course of a conversation. This came up. It was not— I mean, the modern elder thing came out, but like, a modern elder is as curious as they are wise. That succinctly describes what they were saying. They never said one sentence like that. But what they said is, here's what we see. And here are the qualities. And I think by the end of the conversation, I was like, "Okay, Modern Elder is the perfect alchemy of curiosity and wisdom." But it wasn't quite as poetic as that at the start of that conversation. But I think what they really wanted me to see was they knew that I was struggling because in the first couple of months, I was like, "Wow, I'm 52 years old. I'm at twice the age of the average employee here. I've never worked in a tech company before. I'm surrounded by millennials. I don't understand the tech lingo nor the millennial lingo sometimes." And I was feeling a lack of confidence at times. And Brian even said to me, "Why are you so reluctant? Why are you reluctant to be all in here?" I was like, "Dude, I was supposed to be 8 hours a week. It's 70 hours a week now. I'm all in, but I'm reluctant about the fact that I'm just a mentor here." I mean, I'm more than a mentor. I was the head of global hospitality and strategy and in charge of a bunch of things. But part of the role is you want me just to be the mentor. I'm the intern as well. And that's what ultimately led me to coining the term menturn. I'm a mentor and an intern at the same time because my relationships over the course of 7.5 years in the company, I was both a mentor and an intern. And my relationships with people I was mentoring was often a mutual mentorship. I was learning from them. They were learning from me. So, all of that got me very interested in intergenerational collaboration. 40% of Americans today have a younger boss. By the year 2025, the US Department of Labor says the average American will have a younger boss. So, that's amazing. The majority of Americans will have a younger boss. That doesn't happen in historic times. Historically, power rested with older people higher up on the org chart. That's all changed.. And yet, we live in an era where 75% of millennials would like to have a mentor, but only 2% actually have one, a formal one. So, there's lots of opportunities here. That's what led me to starting to write my book, Wisdom at Work: The Making of a Modern Elder. And while I was writing that book down in Baja at my beach home, I had a Baja aha. I had an epiphany. And the epiphany was, why is it that we don't have midlife wisdom schools, places where people can go to reimagine their life, whether it's their romantic or relationship life, their spiritual life, their career life, how they see themselves in the world, what their sense of purpose is. And so, the MEA, the Modern Elder Academy, came out of that. And that was almost 5 years ago. We have 3,000 alums from 40 countries and 26 regional chapters around the world.

Incredible. And also, it's such an interesting concept because also you really had to adapt during the pandemic. So there's a lot to say about that. And I appreciate that you had this Baja aha and you sort of said, "Ta-da, we're going to build this Wisdom Academy." When I encountered MEA and the Wisdom Academy, you said, "Well, we like being in Baja. It's hard to get to. It's kind of out of the way." And I honestly, and I know you're an entrepreneur, but I didn't have the sense that you're like, and we're gonna have campuses all over the place. Like, was your original vision to also be kind of global, have multiple campuses, or were you thinking about keeping it in Baja? Like, how, how has that grown?

Well, let's, you know, and I want to get back to your last question, which I, I spaced on, which is the scale, you know, how do we scale Soul? Um, so let me explain it in Airbnb words and then in MEA words. So one of the things that I really saw early on is that the nature of the people working at Airbnb, there was a lot of soul, a lot of passion, a lot of sense of purpose. And yet, we were scattered. We had 30 different strategic initiatives. And we were obviously growing across the globe. If we were just a localized business, it'd be easier to do, but it was not. And we were obviously disrupting, having to change laws, et cetera. So, it was complicated. So, what are the kinds of things that we did to try to scale soul? I mean, one is we created a program whereby any new employees had to go through an interviewing process in which they were not just interviewing with the people they were going to work with in that department, but that we had two core values people, we had like 40 or 50 people who had been trained in Airbnb core values. They're existing employees who both are trained in it but also are really great role models for the core values.. And these values interviews were really important because a values interview could veto a potential candidate. So, you know, you might have an engineer who's coming in and everybody in the engineering department is excited about him, but then he meets the two core values interviewers and they're like, "No, this person doesn't fit the core values." So that was a way that allowed us to make sure that our process of bringing in new people— and we were doubling, more than doubling in size of number of employees every year. So, your culture changes quickly when you have that many people joining, and especially if they're spread out in 22 offices around the world. So, long story short is that was one way we scaled the soul. Another way we did is we actually created something called One Airbnb. And every year, we would bring all of the employees from all over the world to San Francisco headquarters for 4 days of just an immersion. It's like a festival. And it was fascinating. It was very expensive to do. And so, we were really investing in both culture and soul by doing that. But it also helped people to feel that deep sense of like, I am connected to this organization. And of course, this is pre-COVID. It was actually a long time ago when all this was happening. It was 2013, 2013 through '17 was like my core time that I was with the company. And then I just moved to the strategic advisor role. So those kinds of things are things that we're trying to do at MEA. How are we being really thoughtful about the people we bring into the organization so they're not just a great fit because their skill set fits what we need, but they actually are a cultural fit and a cultural add. Meaning if you just have a culture fit, then you're basically hiring the same people. Culture add is somebody who comes in and is able to also add some diverse voice to the mix, which is important. Yeah. Also, MEI is growing quickly, yet we have made a conscious choice to say we're going to have 2 regional hubs. And then in those hubs, we'll have residential regenerative communities. We'll have, in the case of Santa Fe, we'll have two campuses such that we'll have Santa Fe, New Mexico, and then in Baja California, Southern Baja. And so instead of having dots on the map, because there's so many people who want us to be in the Catskills or Hudson Valley or Napa or Ojai or Asheville, North Carolina, or Austin, Texas. And our conscious choice is to say, you can grow quickly. But if you do it in a singular region or in two regions, in our case, then you have a lot more sense of the touch and feel of the place. And, you know, I'm not on a plane going to four different campuses, but I might literally— we might have four campuses, but they're in two regions. And there might be a beach campus and a farm campus, a ranch, and then a town campus. Four different flavors, but only in 2 regions. So that's another way to scale stuff.

I love that, sort of keeping it more just manageable just geographically. But I want to double-click on what you're talking about in terms of the culture interview. I love that. I had Alexi Robichaud on my podcast, and he's the founder and CEO of BetterUp. He had this idea of balloons where you have— it's the same kind of thing where you have people who want to interview just for culture. So I'm curious, can you think about an interview that somebody would do at MEA, which would be like checking for culture fit, but then also what you just said, which is so beautiful, checking for culture add, or what were the words you used? Sort of the culture expansion.

Culture add. Yeah.

Yeah.

OK. I might suggest two questions here. Number one is my favorite interview question of all time and one that I crafted years and years and years ago. And I think it's really appropriate. It was appropriate at all three of the businesses that I've been involved in. Especially MEA, is what's the number one way you're misperceived in the workplace? And I love this question for the following reason. First of all, it's a hard question. It's not one that you normally hear in an interview. So, I love unscripted questions because I think the interview process can be so damn boring because it's like, "Okay, here's the questions and here's the answers." So, most people have never heard that question. What's the number one way you're misperceived in the workplace? So, the fact that it's a new question is a good thing. Secondly, the fact that it is requiring a certain amount of self-awareness is a good thing. Thirdly, the fact that it actually requires a certain level of other awareness, how people perceive you is very important. You have to know yourself and then you have to know how people perceive you. And then number 4, it is like a welcome mat for an interesting conversation, anecdotal about like, okay, so how does this show up in the workplace? So, I love the question because it actually is a question that in the case of the businesses I've been involved in, I really feel very strongly that self-awareness is probably one of the most important ingredients of a great leader. I also like the fact that sometimes it leads to weird mishaps. Where people say things like, and it opens up a whole new can of worms. I'll never forget one interview where a guy said, "I think that everybody just thinks I'm an asshole, but I'm actually a pretty nice guy." I was like, "Oh, wow. Thank you. You went there. Let's talk about that. Why do they think you're an asshole? How does that show up? And how do you know you're a good guy? And do you want to be perceived more as a good guy in the workplace? And if that's the case, What steps are you taking? It's like, oh man, he just got into a therapy session. But that's exactly what an interview should be. And an interview should be, you know, because if you're just interviewing them based upon like how they show up and look pretty, look good, you know, like you're not— that's not the reality of how you're going to work together. Now, in terms of the culture ad question, I like it, especially if I'm talking to someone from a diverse community, you know, who doesn't fit the predominant demographic in our company is like, I like to ask them questions like, what do you see is missing in this company right now, both in our strategy or our culture or our leadership team? And why do you think that's missing? Wow. That's a hard question for someone to answer because like, oh, I'm now going to call you out, Chip, and say, I think your company's missing this. And I'm going to tell you why I think you are missing that. It's like, wow. Again, on that question, I don't expect someone to be perfect in their answer. And it can be awkward because they don't want to piss me off. But I really appreciate candor and someone who can candidly give me their perspective and I can learn something from them. There's a new insight that comes out. That's wisdom.

Yeah, I love that. Chip, I really have to ask you now, how would you say that you're most consistently misunderstood in the workplace?

Misperceived. I think I'm misperceived. So, the way I'm misperceived, and this is true, this is an easy answer for me, partly because I've asked this question a lot, so I know it, but it's just true. It's been true everywhere I've worked. My name is Chip. I am sort of an easygoing California kind of dude. My first company was called Joie de Vivre, all about joy of life. I have a little bit of a spiritual New Age sensibility to me. So the way people could perceive me is like, Chip is just a kickback dude. He's such a nice guy. He's intense, maybe, but he's smart. But what they are really missing is the level of intensity I have. I am a full-on intense, pretty driven person with very high standards for myself. Having said that, What that means is someone thinks coming into the company, "Oh, Chip's a nice guy." I think that's generally true, but I think what they think is Chip's a nice guy and he's pretty lax. He's pretty easygoing. And I'm not that lax and I'm not that easygoing. I am not someone who gets reactive all that often, but I do sometimes. But I am exacting. I mean, I really like to drill down and say, "Okay, so what went wrong here? What's going on? What can we do differently?" And instead, I don't like to focus just on the negative, but I like to look at what can we learn here? What's the key lesson? And one of my pet peeves is people who make the same mistakes over and over again and don't learn the lessons. I think it's really important because if someone actually is operating that way in one part of their life, they're probably operating that way in other parts of their life. So I would say that the summary on this is What people ultimately experience is working with Chip is an intense experience. It is more engaged than I've ever been in my work. At times, I feel intimidated, not because Chip is intimidating me with questions, but because his expectations of what he expects out of me are so high. So that's, you know, that's— I would say that's pretty accurate.

Yeah, I can see that. I, and I can definitely see that. And also, I especially appreciate that you're— you do have this kind of vibe, and you know, you're, you're soft-ish spoken, right? You're not reactive and you're not going to raise your voice to every— to anyone. And at the same time, I can see that you have exacting standards. And I would just say that from my experience, Modern Elder Academy, MEA, reflects that for sure. You know, another thing about you, Chip, is that you have built a very strong personal brand. In fact, the first time I ever heard from you, I heard about you, was many years ago when suddenly this newsletter got lopped into my inbox. I had no idea who Chip Conley was and why, but like there you were writing a newsletter to people. I don't know, spam. Spam. Yeah, my first experience with you was spam, totally. But so, but it will all work out 'cause I was kind of interested. I was like, wait, Baja? I've never heard of, but where's Baja, right? Have you heard this whole like story? Story of someone named Chip Conley, but I didn't really know who that was. My point being that you have really developed a strong personal brand. And I'm just curious, what's your intention in doing that and how has it served you?

Well, you know, a company has a brand and a person has a reputation and a person can have a brand as well. In the world we live in of knowledge work, your ability to be a thought leader, to be able to articulate a perspective is increasingly important. And this is not just for authors or academics. I actually deeply believe that one of the most important things any kind of leader can do is to articulate a leadership perspective of what it means to be a leader. And, in fact, for 30 days back in the Joie de Vivre era, when I sort of felt like we as leaders in the company were not walking our talk, I struck down the use of the word leader or manager for a month. And, we used role model. So, if we're doing a leadership retreat, we're doing a role model retreat. If we were doing a manager training, we were doing a role model training. And so, for a month, we did that. And it was fascinating how it shifted people realizing that we are role models as leaders. So, I guess I would just say that, for me, the articulation of how the world works, for me, that has been in the form of Maslow's hierarchy of needs. Applied to business. I wrote about this in my book Peak: How Great Companies Get Their Mojo from Maslow. The idea that there is a hierarchy of needs for our employees, our customers, and investors helped me to be able then to say, if that is true and those are the principles that define my leadership and I want my team to sort of understand those, how do I— how is part of my process, part of my legacy sharing those principles in a role model kind of way, such that people who've worked with me understand my point of view. And the point of view is not just the point of view, but the actions that then follow from that. And that's what a reputation is. Reputation or brand isn't just the articulation of the point of view. It is the embodiment of that point of view, that way of being. In such a way that you are a role model. And I am an author. I mean, I have written a bunch of books and I've spoken on the TED stage twice. And so, there's a part of me that feels like, "Okay, yeah, I better be careful in crafting my brand, personal brand," because there is, I don't want to say a lot riding on it,. But some of my ability to be influential in the world is a function of that. Mm-hmm.

So, yeah, that's really well said. How, how would you suggest, you know, a new founder think about that now? So you have a 26-year-old founder, a 30-year-old founder who's just starting out in their entrepreneurial journey, maybe hasn't thought about personal brand at all. What advice do you have for that person?

I would, I would, I would focus So, we live in an era where it feels like the first thing you do is you get your bullhorn and you start saying, this is what I believe. And I actually don't think that's what you do first. Back in the old days, so to speak, you come up, you get clear on what it is that you believe, and then you actually test it out a little bit and you refine it. The diamond only gets better because of how it's refined over time. You don't throw that you don't sort of just test it in social media. Also, be careful. I wrote a blog post. So, my blog is WisdomWell. It's a daily blog. I wrote a WisdomWell post recently that says, "Are you a paint-by-numbers leader?" And the whole premise was like, no one's going to buy a masterpiece by an artist where it was all paint-by-numbers. I mean, it might look good or okay, but it doesn't feel authentic and it's still a commodity. And similarly, leaders who lead by slogans, other people's slogans, you can't be an open-door leader with a closed-door mind. And so, just because you have a slogan doesn't necessarily mean your behaviors are embodying that slogan. And it doesn't necessarily mean that that slogan, which is a cliché, is really the best definition of how you show up as a leader. So, I would start, if I was a young leader, I would start instead of getting all worked up about who's doing your social media and all that, I would really refine that point of view and whatever form it takes. I like to write things. So, I would almost try to articulate it in a page, a one-pager that says this is my leadership philosophy, and then vet it with people. And ask people, "Does this make sense? Do I live this?" Etc. And then refine it over time. I ended up going out and speaking about my point of view and then ultimately writing books about it and giving speeches about it. But you don't have to go that far, but start with the raw material. Because if you start with trying to package something that is not nearly ready for primetime, you actually over time could do damage to your brand or reputation because you're not talking about something authentically that you're living.

Yeah, I love that. I think that's great advice. By the way, everyone should sign up for Chip's Wisdom Well. It's a daily blog. I look forward to it every day. And I read that one and it was in the context of you working with one of your entrepreneurs whom you mentor.

A mentee, yeah.

Yeah, a mentee. And I'd love to know, just sort of broadly speaking, I know that you now mentor other entrepreneurs. I'm curious, what are the kinds of things you find yourself teaching them, so-called, the most? And what are you learning from that experience of mentorship now?

I think one of my favorite exercises I do with a mentee, especially a senior leader, is I I ask them, what are the 5 adjectives that they most want people in the company to use to describe them? So in essence, what's their brand reputation? What are the 5 adjectives? Okay, let's look at those. All right, these are the 5. Now, let's go out to a handful of people, both direct reports, senior leaders, but also other people in the company. Maybe it's 20, 30 people. Let's do a survey. This is not the only question on the survey, but this will, you know, let's make it a brief survey. It's like it takes 5 minutes to do. But one of the questions is, what are the 5 adjectives that best describe you in the workplace? And let's see what comes back. And then let's match these up and see, is there a match? It's a very revealing exercise. I mean, even knows this is coming. I, you know, rarely do you have any of the of the 5 that you want on there. Sometimes you'll have 1 or 2 that are close. But then you go to the next step, and that's the really interesting one. The next step is, OK, Chip, you want to be an encouraging leader. You want one of the 5 adjectives to be that you're an encouraging leader. You encourage courage. Because even within the word encourage is the idea of courage, which the heart— that comes from the word heart in French. So, what are the habits that I'm going to start putting into my life that would actually make me an encouraging leader? So, for example, one of my habits that I, when I was doing this exercise myself 30 years ago, was, oh, okay, I'm going to come up with 2 pieces of recognition privately that I will give each day, one to one person, one to another person. Something that's quite specific and unexpected to just help a person see that I'm noticing because we have a tendency to catch people doing something wrong. What about catching somebody doing something right? And my perspective was I want to do that as a habit. And if I start doing it as a habit and I get it right, I will keep doing it without having it be a checklist item. So, for a year or two, it was a checklist item. If I didn't do any on Monday, I had to do 4 on Tuesday because it's 2 a day. I gave myself the weekends off. So, it was, in essence, a minimum of 10 a week. So, long story short is that kind of— in my mentor relationships with leaders today, I really help them to do that deep dive to say, how can we link up your aspirational brand identity with what people are actually experiencing. The other question that I help leaders start to ask their direct reports is, "How can I support you to do the best work of your life here at Airbnb?" for example. And it's a great question. And it's one that I think every leader should learn to ask. Why? Number 1 is two-thirds of American workers think that their boss wants them to fail.

Really?

You think I want you to fail? Like, my life is not easier by you failing. That's what a boss should say. But the truth is a lot of people feel like the odds are against them, the system's stacked against them, they're a victim. So, the fact that you start the question with how can I support you is a great starting point. Then the next part of the question is to do the best work of your life. How can I support you to do the best work of your life? Wow, you want me to stretch that Yes, I do. I want to be here and I want to be your permissionary to do the best, give you the permission to do the best work of your life. And that's, I think, a really important thing to say because actually, especially if it's in tandem with how do I support you? But the big aha in this question is how can I support you the best work of your life here at Airbnb? Or whatever company name, is you have now, as the leader, as the boss, given agency to your employee, to your direct report, to actually come up with a list. And for a lot of employees, a lot of direct reports, this is unfamiliar territory. Because what's familiar is like, "Oh, this company sucks. My boss doesn't care." Blah, blah, blah, blah, blah. And so now I have in my lap the responsibility of a week from now coming back to my boss and saying, "What do I need? What kind of support do I need to do the best work of my life here?" And it leads to what can be a really fruitful conversation. It also sometimes leads to like, "Okay, this isn't going to work out because you couldn't come up with your list," or you came up with a list of 22 things and There's only one thing on this list that is even remotely possible that we could do. Now, sometimes people come up with things on the list like, "Oh, my God, there are some great things on this list. They're sort of against HR policy, but let's actually go and talk to HR about some of these things because there's some good stuff here." Or someone comes up with, as one person did with me, they came up with a list and the first thing on their list was, "I want to actually take a 1-year sabbatical a month from now." Okay, I hear you. Okay, how can I support you? That's really like you want to win your sabbatical. What if we weren't able to do that now? What if we could actually work toward that so a year from now, we actually could try to do that? And maybe it's not a year, maybe it's 6 months. So, there's sometimes the opportunity to have the conversation. And if it's someone who I really believe in and I really like and I want to be supportive, like, okay, This is in your head. You thought, as the director, Port, the only way I can get a sabbatical is if I quit. And so, you were in your head thinking a month from now, I may quit because I actually need a sabbatical. And what I'm saying to you is, no, let's look at how we can work toward that, et cetera, et cetera, et cetera. So, it's important to have these meaningful conversations. With our bosses, because most of the boss— most of the relationship and communication we have between boss and employee is transactional. And what we could use is a little bit more transformational leadership.

I love it. I— when you just said— you just summed it up by saying it's important that we have these meaningful conversations. No question. Real talk, real talk, real talk. Because everything you just said is about real talk and about having the real conversation underlying the sort of transactional or superficial. And to your point, it takes away the ability to just complain. You suddenly have to take responsibility for your life as a direct report in the workplace. I think it's so powerful. Chip, what have you learned from your mentees?

Wow, I mean, so many. I mean, I, you know, with Brian, I'll just start with Brian. Brian was my mentee, and I, you know, but we mentored each other. We had what I called an EQ for DQ trade alliance. I offered him emotional intelligence in the form of leadership, understanding oneself, et cetera. He offered me DQ, EQ and DQ, DQ being digital intelligence. And he offered me understanding not only how to operate my iPhone more holistically, but how to develop a website with great UX and UI, how to actually deal with Silicon Valley investors or venture capitalists. Because I, as a hotelier, I never had venture capital money because venture capital money wants a return way too quickly for the hotel industry. So I learned that from him. So that's one example. I've had Gavin Newsom, who's now the governor of California, Before he was even the mayor of San Francisco, I was his mentor. He was a hospitality, budding hospitality entrepreneur. I'm still his mentor now as the governor of California. That's interesting.

What have you learned from him?

Yeah. What I've learned from Gavin along the way is I would say how in certain instances, you have to be willing to take a stand and do so in a very public way. He did that with gay marriage in 2003, 2004. Actually, 2004. It was actually Valentine's Day. He was really newly the mayor of San Francisco. He'd just been elected. And he announced gay marriage was legal in San Francisco. Now, I mean, it was fraught with all kinds of other things. It was way, way, way early. But he was by far the earliest politician to endorse and take steps towards gay marriage. And more recently, and I don't want to get too political, but more recently he's been taking some very active steps, very aggressive. And what some people will sometimes see as ambitious, because, and to be fair, he's a politician and yeah, he is somebody who's looking out for himself, but don't we need more leaders who are sticking out a stand on something and willing to stake their political reputation on it. Yeah, I think we need more of that because we have got way too many people who are just not doing that. Other mentees I've learned from, Marian Goodell, the CEO of Burning Man. I was on the board of Burning Man a long time. I learned from her that loyalty, you just like how important loyalty is. I mean, I think at times I've been willing to accept things that a lot of leaders might not because I was like, "Oh, I'm going to give them the benefit of the doubt." She doesn't give a lot of benefit of the doubt. She really asked more importantly, "I want to assume best intentions in the person." And that's what she does. But when she gets a hint that the person doesn't have best intentions, she cuts bait quickly. And she does it, you know, I mean, not always in the easiest way, but I think she's very, very— she's very instinctual. The truth is, if you're a leader and someone who works with you has lost— you've lost their faith or you've lost faith in them, you know, maybe you want to actually have them stick around. But the truth is, why have them stick around if you've lost faith in them? It just actually makes it ugly. It makes for what could be a very ugly situation. So she's, she's one of those people who's really able to like pull the bandaid off pretty quickly.

Hmm. That's amazing. I think it's so helpful to your point about multi-generational relationships where there, it's clear. And I think it's so important to acknowledge the mentoring goes back and forth and the learning goes back and forth. I think it's so important, you know, on the topic of age, a lot of the founders I work with, they just, just like you said earlier, the notion of people, most people having bosses who are younger than them. Well, the founders I work with, they often have direct reports, executives who are not just older than them, but are seasoned executives. When you get to a certain stage in a startup, you're hiring seasoned executives. They're 20 years older than you. And they say to me all the time, it's, it's sort of a question, how do I manage people who are so much older than me? But it's more, they acknowledge like, I'm uncomfortable managing, you know, Max because I don't really know what to say to Max because both he's 20 years older than I am, so much more experienced, super smooth, and also I've never done marketing before or whatever it is. What, what advice do you have for founders who are in those shoes?

Yeah, let's, I'll give my advice on both sides because I think also Max needs to know how, how to, how to operate in an environment where, you know, your boss may be younger than you. For the young founder or the young leader with older reports, I mean, on both sides, it's about respect. So, let's start with that. How do we show respect? But not respect just for the sake of making things look good, but like really truly understanding that this person has some wisdom in them. So, for the younger CEO, one of the things I would say is if you have an older leader, older employee, who seems to have some institutional wisdom but is having a hard time getting it out, make sure— one of the things I said once to someone who was a lot older than me, "Hey, don't mistake your war stories with wisdom." And what I meant by that was sometimes older people are like, "Oh, this is the way the world works," or, "Let me tell you about this story or that story." And I don't have time for that. Distilled-down wisdom is distilled. Metabolized experience that leads to distilled compassion. And so, how do you help an older person distill down their knowledge? If I went to Airbnb and I was just spouting out, "Oh, well, it takes an average maid in an 8-hour shift can clean 16 rooms," that's hospitality knowledge, but that was not worth anything at the Airbnb hospitality company. So, understanding how do you take your knowledge and make it relevant in a new context. So, I would say, so sometimes you actually have to help that person, that older person articulate. Like, a question I would say to an older worker is like, "Hey, a week from now, I would love to have you come back and tell me, What are the 5 pieces of institutional wisdom or advice you would give to a new leader in this company? And they can be specific to you. They can be specific to the company. But something that actually is like has your fingerprints all over it. Now, similarly, for Max, the older person who's reporting to the younger CEO, do not dismiss this person, the younger CEO. Just because they don't have as much experience. They may have an openness to new ideas and a way of seeing the world that is really wholly different than you, especially if, as in Brian's case, Brian was a disruptor of the hospitality business and I am a dinosaur in the hospitality business. I may not be able to see it the way Brian does. So, think of yourself as Margaret Mead amongst the millennials. Be culturally curious. Be culturally curious. Be intellectually curious. Ask questions. Most importantly, ask questions. Use appreciative inquiry, which is a method of asking questions that will allow you to understand a little bit more what this young person is talking about.

I love it. That is so wise. I think that's so helpful, you know, in actually every aspect. Everyone could take that wisdom, to be honest with you, right? Not just older people, younger people. And another thing that my— the CEOs I work with, the entrepreneurs I work with, they struggle with, especially as they get— again, as the company gets bigger, they get a little more well-known, they get, you know, the stakes get higher, they begin to really have trouble to get people to tell them the truth. Because like, oh, you're 8 people around, everyone's kind of telling you the truth. You're a bozo, you're a knucklehead, don't do that. But when you're suddenly 1,000 people— not suddenly, but when you're 1,000 people and you're the CEO and people come with their own baggage about the boss and the CEO, it's— they just don't always get the truth. How do you advise? Have you experienced that? I think first of all, and second of all, how do you advise founders to make sure they're getting the truth from people?

It's a great question. I think there's a few different ways to do it. And so, I don't think there's a singular way to do it. So, let me start by saying that. I don't have a prescription that I think is generic across all people. Let me start by saying that there's two extremes. I don't think either of them work all that well. There's the extreme of, "Let's do a town hall meeting and let anybody ask questions." Well, in certain cultures, that isn't going to get you much because people are going to be really cautious. Or in some cultures, it's going to be the opposite. Just like the only people who come up to the microphone are the people who are just pissed off about something. So I really think the performative nature of doing it in a town hall kind of format doesn't work so well. Similarly, I think anonymous surveys that are just anonymous surveys or even like Social media is the ultimate form of anonymous survey almost. I don't think that's the best either because it's people ragging on things. So, what are some other alternatives? Well, I'll tell you something that we did at Joie de Vivre that I think worked really well, and I learned it from Southwest Airlines. So, Herb Kelleher, for 37 years, the CEO of Southwest, was a mentor of mine, like a mentor pen pal of mine. And I learned this from So, we created cultural ambassadors. And these were people in the organization. In our case, it was— we have hotels, restaurants, and spas. So, we had a cultural ambassador for each of our businesses. And they come together and once a month, they have a conversation about how their particular property is enhancing its culture, how they're building a culture of recognition, and how the cultural ambassadors and the line-level staff are in charge of philanthropy for the company. So those were the 3 key things they did. But the other thing that they would do, we used the cultural ambassadors for on occasion, was if we really wanted some truth-telling. So in essence, what it would be is we would say to the cultural ambassadors, "We would love some feedback about the leadership team." Now, you can do surveys on this stuff, and sometimes the surveys can be helpful. But generally, you know, let's have a cultural ambassador conversation around, the leadership team or the strategy of the business? What are some questions are the mainstream employees want to hear? And what's some feedback that we need to hear? So by actually having it filtered through the cultural ambassadors who were line-level employees but trained in what it meant to be a cultural ambassador, I think we were able to have a conversation with our senior leadership team and our cultural ambassadors in such a way that we can actually come up with some good solutions. So that's more of a leadership one. On a personal level, I just, I love sitting down with one-on-one with my leaders and, and I don't spring it on them. I just ask them, you know, come back to me a week from now when we next meet. What can I do to be a better leader? It's that simple. I want you to tell me something that might be hard for me to hear. And I want to be able to listen. So you will have 5 to 10 minutes to talk, and I'm not going to interrupt you during that 5 to 10 minutes. You know, I'll take notes. And then I want to really explore it and look at how you can help me be better. How can you support me to be a better leader? Here at MEA or at Airbnb? So it sort of puts that original question of how can I support you to do your best work in your life? How can I— how can you support me to be the best kind of leader here at— in this company is not a bad question to ask your direct reports.

That is a great question. I love that. And also listening to what they have to say and not interrupting. It is so powerful. Have you asked that of your folks at MEA and have you adjusted your style over the the past, you know, I guess 5 years as you've written?

Yeah, I mean, I've only done it once, and I did it with— gosh, I need to do it again because the last time I did it was about a year ago and we've had a lot of new hires since then. Yeah, and I got great— it was during our summer break and I had some time and I really wanted to develop some leadership ethos at MEA that might have been different than what I had than doing it at Airbnb. And I would say the number one piece of feedback that I got that was deeply appreciated was— well, there are two. One that I've always gotten for a long time, which is, "Help us create boundaries. We are a boundaryless organization and you're a boundaryless leader. You will do emails. We're doing this conversation right now on a Saturday." So, I mean, How do we create an organization that has boundaries? And so, that led to a really, really interesting thing. Actually, I want to talk about that one for a second. So, that led us to doing something that's really interesting. We created a set of boundaries. What we did is in January, we gave everybody who's a senior leader, 15 or 16 people, the ability to talk with their boss about what boundaries they'd like to adhere to in 2022. The conversation went on as long as the boss was like, "Yeah, those boundaries sound good. You want to take your Sundays off and have an out-of-office message? Totally fine. You want to not have— you're on the East Coast. You don't want to do any meetings after 3 o'clock? Fine." So, having that conversation and then having all of us come together and talk about what our boundaries were and then having our administrative team compile it into a Google Doc such that it influences when we're going to do leadership retreats, when we're going to have meetings, et cetera, standing meetings. And then, actually rewarding everybody 5% at year-end based on their self-determined perspective on whether they actually met their boundaries. And we would do a quarterly leadership conversation about are people green, yellow, or red relative to their boundaries. Wow. Phenomenally changed how we're operating. So I would say that's one piece of feedback that was really— I was able to take and run with. I think the other one was when I am stretched for time and someone comes to me, like, I am at my absolute worst as a leader when I have a short meeting, someone has not prepped me properly to know that there's an important thing they wanted to talk about and they bring it up 5 to 10 minutes before the end of the meeting. It's like, I hate that. I don't know why I hate it so much, but I just— because I feel like there's a necessity to actually somehow resolve it in the 5 to 10 minutes. And if this is that important, why didn't you tell me in advance? If this is that important, why didn't we just dedicate the whole meeting to this? The feedback I got was, I need to When that happens, I need to just say, "Oh, that's a great idea. Let's find the time to talk about this later." It's that simple. And I've tried to adhere to that since then. But it was a great piece of feedback that this particular person had seen on multiple occasions that I had sort of lost my temper. You know, again, relatively speaking, for me to lose my temper is not like what it is for other people sometimes. But I would just get pissed that they, this person who was bringing it up at that point, and I felt obligated to try to resolve it in 5 to 10 minutes. I don't have to resolve it in 5 to 10 minutes. If it's an urgent thing that needs to be resolved, any, you know, then we'll figure that out. But usually it doesn't have to be resolved immediately.

Right. But it makes you feel pressure and then you get irritable and it's helpful just to see that about yourself. Yeah. Thanks, Chip, for sharing that so honestly. Just a few more questions. What do you wish you had known earlier on your journey?

Well, I wish that I had realized in my 20s that my sense of self-worth is not defined by the success of my company. It's a hard one in my 60s to still say that, but it is easier to say it now than it was back then. My first hotel was called the Phoenix. It's a rock and roll hotel in San Francisco. In San Francisco. And so people would say, Chip, how are you doing? Oh, the Phoenix is doing well. That's how I would respond. It's like, no, Chip asked how you are doing. And I responded by talking about my only hotel at that time. So I think there was an element for me that my sense of self-esteem was way too connected to the ups and downs of the business. And that was unhealthy for me. I was not a good role model for others. And I think over time, what I learned to do was to both have a holistic and enriched enough life that no one part of my life was going to sink any other part. And also realize that I need to take a break sometimes, at least take a moment to just laugh at things a little bit and not take it all so seriously.

I love it. Thank you, Chip. Very wise. And what advice do you have for other founders as they embark on their journey to grow into leaders?

I mean, I think a piece of advice I'd give that's sort of an unusual one because I've already given a lot of advice on this podcast is be careful of the investors that you bring into the fold. You get the investors you deserve and hopefully you deserve really great ones. But sometimes in the frenzy of trying to capitalize something, you end up with investors that are a real misfit. And in my book, Peak: How Great Companies Get Their Mojo from Maslow, I have an investor pyramid. And the way I look at the investor world is there's 3 levels of investors. Most of them are at the bottom. They're transactional investors. It's all about how much money are we making, how soon. It's all based on internal rate of return. And nothing wrong with those investors as long as your business model is well suited for that. Is there an alignment there? The second part of that investor pyramid is the relationship investor. Warren Buffett is the relationship investor. He deeply invests in individuals. He tells the CEOs of the companies that he invests in, I want you to operate as if you're going to be here 100 years from now. And so, there's an element. And for me, we had 52 boutique hotels and someone could be a partner of us in one hotel and we're going to sell that hotel. But the partner or the investor says to me, "We're selling that hotel, but there's more chapters to write in this book." The book of our relationship is not a singular chapter of that hotel. If it was that, they would be a transactional investor. And then the third level is a legacy investor or a mission-aligned investor. And those people are great because they're like, "Okay, it's not about the short term. It's about the long term." They're as passionate as you are about the purpose and they have a pride of ownership. The risk in them sometimes is that they package themselves as a legacy investor, but at the end of the day, when things go bad, they become a transactional investor pretty quickly. And that's okay. I think a great legacy investor better be looking at the bottom line. And the reason the hierarchy of needs is interesting is because you have to have the foundational needs right in order to address those higher needs. But I would just say I have learned the hard way that sometimes I've had a legacy project that required a long perspective in terms of how— because we were disrupting something, it wasn't going to happen overnight. And then I had a hedge fund as the investor, like, well, That didn't make sense because hedge funds were really short-term-minded in terms of how they wanted to make their money typically. And so, long story short is I think it's an important thing because if you don't get that piece right, the customer and the employee relationship will suffer, not just because of dissension and problems, but for an investor's transactionally-minded, the thing that's most important to them is like, let's keep our labor costs low, So, pay less and let's keep our operating costs low and let's jack up our prices. So, the relationship you're going to have with your employees and customers in that kind of environment can be pretty toxic, but then the net income can look really good. Mm-hmm.

Very wise and I think very practical. So, thank you very much. And Chip, I want to thank you for being on this podcast with me. I want to thank you very much your friendship over the years and for your mentorship of me over the years and how much I've grown in the context of being part of your beautiful community, Modern Elder Academy. And I really want to encourage everyone listening to check out MEA. It is a very wonderful place, just beautiful and wonderful. And also the activities going on, the time for reflection, the incredible spontaneity or serendipity that you experience there with that beautiful community is just very nourishing and will be a net add to your life no matter what age you are or whatever transition you're in. So thank you, Chip, for all you've done.

Well, thank you. We actually sometimes have groups of private groups that come down and go through the program together. We've been doing that with YPO and with Inc. magazine and etc. And so it's, uh, it's encouraging to know we can— that we have that. We also have MEA Online. You can check it out at modernelderacademy.com. And you can just look at the program section and you can see the workshops there, uh, sabbatical sessions this summer, as well as our different online courses.

Amazing. Thank you, Chip, so much. I really appreciate it.

Yes, Alisa, I love you.

Love you. Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.