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

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, 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're doing a manager training, we were doing a role model training. And so for a month we did that. It was fascinating how it shifted people realizing that we are role models as leaders.

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, 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 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. Choose. 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—

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, so let's start by just talking about what, 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 can't, 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 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 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 and 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 the size are too too small or too big. And that homework people do in advance, then they arrive and we start to do that on the first, within the first 24 hours, a deep dive into like, 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 two 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 three 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 like 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 go through their, their own journey of identity. Like, like, like letting, 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, you know, when 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, 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, I experienced it. The good news for me, so when, when it came to Joie de Vivre, the company I had started and was CEO for a long time, 22 years into it, I had a flatline experience. I, I had a bacterial infection. Septic leg, broken ankle, and was put on 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 was that 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. 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 that everybody had to be confidential about it and I had some time to prepare for it. Which was great because we need that. Because generally speaking, if, 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, you know, what are, 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 moved 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, you know, I had moved on. I truly had a lot of— 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. Yeah. As you know, I'm gay. And so if you come out, I came out at age 22 in 1983 at a time when I 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 this, that I feel energetically whole and seemingly confident about what's going on, and they get a little bit less worried. So when it came to people saying, oh my God, you sold the company, and they could see that I was, there was a relief, a tranquility, and also an excitement for what's next. People, yes, some people had a hard time with it, especially those in the company who knew, okay, there's a new owner here. And that, 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'd go to get my free suite, you know, every honeymoon, 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, you know, one of our restaurants. He's like, Hey dude, I'm 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. Of course we do. And, and there's this adolescence is a, you know, 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. Teenager, 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. You know, I'm just thinking, 'cause Sv Bandh, 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, the hint from other founders that when you sell your company, you're gonna be shockingly left with this void. And so he kind of tried to mentally and emotionally prepare. Do you specif— 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 know, 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 what part of what some people come for. But there's also a great book by Bo Burlingham called Finish Big. He's the one who wrote Small Giants. Great, great book, sort of a, you know, a classic. And Finish Big is a book about what's the mental state, the emotional things you need to think about in the process of selling your company and moving towards 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 sell, 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 an 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 I ideally ritualize it in some way. You sort of say, okay, 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, when you and I have friends and family members and people like that. The messy middle can get— can be a really dark and gooey time. Think of the cocoon or the chrysalis of the caterpillar to butterfly journey. You know, 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 that— and like, okay, I'm going to test this out, see if I like it, 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 the, 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 that's, 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's happening, the butterflies coming out of the crystals, and you're really embarking on that new thing that you're really excited about. And for me, you know, selling my company was hard. My sister, who had worked for, 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. Now 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, was that I sold my company, Joyvive. I still owned a piece of it. I was executive chair for 16 months afterwards, 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 the thing. 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. Went to 36 festivals in 16 countries in one year. So I was really, 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 was the co-founder and CPO 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. And he said, I want you to come in and be my mentor. I want you to help us become a hospitality company, you know, that's global, global, and 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's 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. 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 group and Kimpton was the largest, and they sold for 30 times more than we sold for. And I was like, ouch.

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. And, but I wasn't focused on that because I'd 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. So a regret's 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. Um, I think it's like 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 know, you were gonna be like, sure, I'll do a little thing. And suddenly you were working full-time, like probably more than full-time. And, and I, 70 hours a week. 70 hours a week. And, and I wanna hear about kind of the insight that came out of there that, um, that led to your building Modern Elder Academy. But like, 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 dot, dot, dot, 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 got— brought you to Modern Elder Academy.

So let's start by saying that within a month or two after I joined, Brian and, uh, Joe Gambier, 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. 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, okay.

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

Like, what do you know? No, no. 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's the qualities. And I think by the end of the conversation, it's like, okay, a modern elder is the perfect alchemy of curiosity and wisdom. And but, you know, it wasn't quite as poetic as that, you know, at the start of that conversation. But But I think what they really wanted me to say 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, you know, 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 the part of your role is you want me to just 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 and a half 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. You know, I was learning from them, they were learning from me. So all of that, you know, 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, you know, power rested with older people higher up on the org chart. That's all changed. And yet we live in an era where, you know, 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, you know, relationship life, their spiritual life, their career life, how they see themselves in the world. What their sense of purpose is. And so the, you know, 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. It's— and I also— it's such an interesting concept because also you've 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 gonna 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, 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, yeah.

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, and I wanna get back to your last question, which I, I, I spaced on, which is the space, you know, scaled, you know, how do we scale soul? So let me explain it in Airbnb words and then in, in, in MEA words. So one of the things that I really saw early on is that, that the nature of the people working at Airbnb had, 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. We were just, and we were obviously growing across globe. If we're 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 Sol? Number 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, um, people, core two. 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, um, 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, 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 have, we would bring all of the employees from all over the world to San Francisco headquarters for 4 days of just a, you know, an immersion. It's like a festival. And it was fascinating. It was very expensive to do.. And so we real, we're 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, 2014, 2013 through '17 was like my core time that I was in the company. And then I had just moved to the strategic advisor role. So those kinds of things were, are things that we're trying to do at MEA. And 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 sort of, 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, I mean, it's 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 2 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 for, 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 4 different campuses, but I might literally, we might have 4 campuses, but they're in 2 regions and there might be a beach campus and a farm campus, a ranch, and then a town campus, 4 different flavors, but only in 2, 2 regions. So that's another way to scale.

I love that sort of keeping it, you know, more just manageable, just geographically. But I wanna double-click on what you're talking about in terms of the culture interview. I love that, you know, I had Alexi Robichaud on my podcast and he He's the founder and CEO of BetterUp, and he had these, this idea of balloons where you, you know, have, I guess the same kind of thing where you have people who wanna 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, or what were the words you used? You know, sort of the culture expansion.

Culture add. Yeah.

Yeah. Okay.

I might, I might suggest two questions here. Number one is my favorite interview question of all time. And, and one that I, 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 like the interview process can be so damn boring because it's like, okay, here's the questions and here are the answers. So most people have never heard that question. What's the number one way you're misperceived in the workplace? So that, the fact 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, 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 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 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. And I'll never forget one interview where a guy said, I think that everybody just thinks I'm an asshole, but I'm actually pretty nice guy. I was like, oh wow, thank you, you went there. Um, 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? Like, what is the way? 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. An interview should be Because if you're just interviewing them based upon how they show up and look pretty, look good, that's not the reality of how you're going to work together. Now, in terms of the culture ad question, I like, especially if I'm talking to someone from a diverse community who doesn't fit the dominant 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? Well, it's a hard question for someone to answer because like, oh, you, I'm now gonna call you out, Chip, and say, I think your company's missing this. And I'm gonna 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 it's a, you know, they don't wanna 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. I, you know, my name's Chip. I am sort of an easygoing California kind of dude. You know, my first company was called Joie de Vivre, all about joy of life. I have a little bit of spiritual New Age sensibility to me. So the way people could perceive me is like Chip is just a kickback dude. Oh, he's such a nice guy. He's intense maybe, but he's, you know, 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 like really like to like drill down and say, okay, so what went wrong here? Where, what's going on? What could we do differently? And instead of, I don't like to focus just on the negative, but I like, I like to look at like, What's, what can we learn here? Like, what's the key lesson? And I want, you know, one of my pet peeves is people who make the mistakes, same mistakes over and over again and don't learn the lessons. Like, 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 like, what people ultimately experience is working with Chip is an intense experience. It's— 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-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. Um, 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 you was many years ago when suddenly this newsletter got lopped into my inbox. I had no idea who, like, who Chip Conley was and why, but like, there you were writing a newsletter to people. Yeah, yeah, my first experience with you was spam, totally.

But he's so—

but it, it will all work out because I was kind of interested. I was like, wait, Baja? I've never heard it, but where's Baja, right? Have you heard this whole like 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, uh, a company has a brand and a person has a reputation and a person can have a brand as well. I, you know, in the world we live in, in not of knowledge work, You know, 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 we could not use— so if we're doing a leadership retreat, we're doing a role model retreat. If we're 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, that, you know, we are role models as leaders. So I guess I would just say that, that for me, the articulation of how the world works for me, that, 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 that's— 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, in a role model kind of way such that people who've worked with me understand my point of view. And, 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'm, I am, and I'm an author. I mean, I have written, you know, a bunch of books and still I want to, and I've, you know, spoken on the TED stage, you know, twice. And so I'm, I, there's a part of me that feels like, okay, yeah, I'm, I, I better craft my, be careful in crafting my brand, personal brand because there is some, 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, um, 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 first. 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 the, you don't sort of just test it in social media. Also be careful. You know, I wrote a blog post. So my blog is WisdomWell. It's a daily blog. I wrote a WisdomWell post recently. It 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 painted 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, 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, you know, 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 whether 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, you know, Does this make sense? Do I live this, et cetera? 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 actually start with trying to package something that is not nearly ready for primetime, you actually over time could, could do damage to your brand or reputation because you're not talking about something authentically that you're living.

Yeah, I love— 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, um, one of your entrepreneurs whom you mentored.

Yeah.

Yeah. A mentee. And, and I'd love to know, just sort of broadly speaking, I know that you now mentor other entrepreneurs. I care, 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, of mentorship now?

You know, I, 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 want— 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, 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, then you go to the next step, and that's the really interesting one. The next step is, okay, Chip, you want to be an encouraging leader. You want one of the 5 adjectives to be, uh, that you're an encouraging leader. You, you encourage courage, uh, because, you know, even within the word encourage is, is the idea 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, 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 wasn't checked. It was like, I'm like, 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 minimum of 10 a week. So long story short is that, 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, you know, Airbnb, for example? And it's a great question, and it's one that I think every leader should learn to ask. Why? Number one 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. You know, that's what a boss should say. But the truth is a lot of people feel like it's 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 far? Yes, I do. I want you, 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 can put things in a list like, oh my God, there's 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, it was like, um, they came up with a list and the first thing on their list was, I want to actually take a one-year sabbatical a month from now. It's Okay, I hear you. Okay, how can I support you? You do that, you want a 1-year sabbatical. What if we didn't, 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, but you know, 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 direct report, the only way I could 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, you know, 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.

Mhm.

And what we can 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 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. Um, Brian was my mentee and I, you know, but we mentored each other and We had what, what I called an EQ for DQ trade alliance that I offered him emotional intelligence in the form of leadership, understanding himself, 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. You know, 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 had a— 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? 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, uh, 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, and it was way, way, way early, but he was by far the earliest politician to endorse and take steps towards gay marriage. And, um, you know, more recently— and I, I don't want to get too political— but more recently he's been taking some very active steps, very like aggressive. And, and what some people will sometimes see as ambitious, you know, like, because, you know, and, you know, to be fair, he's a politician, and yeah, he is somebody who's like, you know, looking out for himself. But there, you know, don't we need more leaders who are staking 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, you know, 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, she, she, 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 gonna give them the benefit of the doubt. She doesn't give a lot of benefit of the doubt. She, 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 big quickly and she does it, you know, I mean, not always in the easiest way, but she's, 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 that 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 advice on both sides because I think also Max needed to know 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. You know, 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, I, you know, 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, you know, sometimes older people like, oh, this is the way the world works. Let me tell you about this story or that story. And I don't have time for that. Distilled down wisdom is distilled. It's metabolized experience that leads to distilled compassion. And so, like, how do you help an older person distill down their knowledge? Like, if I went to Airbnb and I was just spouting out, well, it takes an average maid in an 8-hour shift can clean 16 rooms. It's like, I don't, you know, 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, I would say to an older, 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 is so helpful, you know, in, 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 are 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 make sure they're getting the truth from people?

That's a great question. I think there's a few different ways to do it. And so I, I don't think there's a singular way to do it. So let me, let me start by saying that I, I don't have a prescription that I think is generic across all people. Um, 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, the opposite. Every, like, just like the only people who come up to the microphone are people who are just pissed off about something. So I don't, 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, you know, 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 what it's people ragging on things. So what is, what is, what are some other alternatives? Well, I'll tell you something that we did at, at Joie de Vivre that I think worked really well. And I learned it from Southwest Airlines. So Herb Kelleher, the 30, 37 years, the CEO of Southwest was a mentor of mine, like a mentor, pen pal of mine. And I learned this from him. So we created cultural ambassadors and these were people in the organization. And in our case, it was, we have hotels, restaurants, and spas. So you 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 are the 3 key things they did. But the other thing that they would do, we used the cultural ambassadors for an 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, you can do surveys on this stuff, and, and sometimes the surveys can be helpful.. But generally, you know, let's, let's, let's have a cultural ambassador conversation around the leadership team or the strategy of the business. What are some questions are the, the, the, the mainstream employees want to hear? And what's the 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 could 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, that it 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 I can— 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 past, you know, I guess 5 years as you've—

yeah, I mean, I've only done it, I've only done it once, um, and I did it with— yeah, 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— I got— it was during our summer break and we— 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 an Emmy at Airbnb. And I, you know, 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— that I've gotten for a long time, which is, help us create boundaries. Help— you know, we are a boundaryless organization and you're a boundaryless leader. Uh, you will do emails, you'll do— we're doing that, we're doing this, uh, conversation right now on a Saturday. So I mean, like, You know, it's, uh, I, uh, how do we create a, an organization that has boundaries? And so that led to a really, really interesting thing. Actually, I wanna talk about that one for a second. So that led us to doing something that's really interesting. We created a set of boundaries. Um, what we did is in January, we, 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, you know, 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, um, 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. It is, phenomenally changed how we're operating. So I'd 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, I just— because I feel like there's a necessity to actually somehow resolve it in the 5 to 10 minutes. And like, if this is that important, why didn't you tell me in advance? If this is that important, why don'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, you know, 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 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. Um, 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 now than it was back then. People, I, my first hotel was called the Phoenix. It's a rock and roll hotel in San Francisco and And so people would say, Chip, how you doing? Oh, the Phoenix is doing well. It's like, that's how I would respond. It's like, no, Chip, I ask 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 I was way too, 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 to 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, uh, uh, podcast, is be careful of the investors that you bring into the fold, you know? Um, you get the investors you deserve and you just, 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, right? 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, and, and for me, you know, we have 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, you know, we're selling that hotel, but like 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, there 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, so 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 You better be looking at the bottom line. And, and, you know, 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, it wasn't going to happen overnight. And then I had a hedge fund and 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, 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, you know, problems, but, you know, for an investor who's transactionally minded, like 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, you know, let's jack up our prices. So, you know, the relationship you're gonna have with your employees and customers in that kind of environment can be pretty toxic. And, but then the net income can look really good.

Mm-hmm. Mm-hmm. Very wise and I think very practical. So thank you very much. And Chip, I wanna thank you for being on this podcast. Me. I want to thank you very much for 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, it is a, it's 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, 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, and so it's, uh, it's encouraging to know we can— that we have that. We also have MEA online. You check it out at modernelderacademy.com. And you just look at the program section and you can see the workshops there, 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 Podcast 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.