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Telling the stories of startup founders and creators and their unique journey. Each episode features actionable tips, practical advice and inspirational insight.
Greg Moran (00:01.906)
Welcome back to the Founders Journey podcast. It's really excited. Peter, welcome back. Good to see you here for another fun episode.
Peter Dean (00:09.33)
Yeah, I'm really excited about this one.
Greg Moran (00:12.582)
Yeah, absolutely. And and super thrilled to have our guest, our guest here today, Chip Connolly. You've probably seen Chip or heard Chip on other podcasts or seen him in the media. He's a New York Times bestselling author and hospitality entrepreneur. His his newest book is Learning to Love Midlife, which is a fantastic book. We'll talk about that a little bit as we go. Before that, Chip founded Joie de Vivre Hospitality at
Chip Conley (00:12.76)
Yeah, absolutely.
Greg Moran (00:40.138)
26, ran it for a couple dozen years. And then he stumbled across a couple of founders who you probably have not heard of with their company, but started to really build this business with them. I don't know, maybe a half, but it was Airbnb. And they asked Chip to come in and kind of help them transform the business and help build it into what it is today. And when he was there, and we're gonna talk about this, he became known as kind of Airbnb's modern elder, which is now really what he's built his career around.
the Modern Elder Academy. So we'll talk about that a little bit. So Chip Conley, welcome to the podcast. Thrilled to have you here.
Chip Conley (01:19.428)
Thanks Greg and Peter, great to be here with you.
Greg Moran (01:23.526)
Yeah, it's and certainly I know the book just came out a couple weeks ago. Right. I know I got it. I think I ordered a preorder and I just got it.
Chip Conley (01:29.488)
came out in, yeah, mid to later January. Yeah, it's been quite a riot. It hit number one on happiness and self-help books on Amazon. So yeah, people seem to be resonating with it.
Greg Moran (01:44.646)
Yeah, well, certainly as two as two middle aged guys for me and Peter, it certainly does it certainly does resonate. We're reluctant to middle age, but I think it's probably fine. We give up the.
Chip Conley (01:49.528)
Hehehehe
Peter Dean (01:57.774)
Yeah, I feel really comfortable about it for the most part. But so can you share your perspective on middle age not being a crisis, but really a chrysalis stage, especially as it relates to leadership and entrepreneurship and people in those types of roles?
Greg Moran (02:00.098)
Where?
Chip Conley (02:00.764)
Good.
Chip Conley (02:10.859)
Yeah.
Chip Conley (02:15.212)
Yep, yep. So I'll give you my story. So, you know, as Greg mentioned, I was a boutique hotel, a hotel company CEO and ran my company for a lot of years. And in the latter two or three years of my time doing that, I just didn't want to do it anymore. With the great recession that was happening, I was burned out.
I was losing some friends to suicide. I had lost five male friends to suicide, ages 42 to 52, three of them entrepreneurs during the Great Recession. And I had an NDE, I died. And I went to the other side and came back because of an allergic reaction to an antibiotic. So long story short, I was like, oh, Jesus, like midlife sucks, midlife is a crisis. And then I got into my 50s after I sold Joie de Vivre, the company, and my 50s were great.
loved it. And it was partly because yes, Airbnb came along, but it was a bunch of other things too. And I was like, wow, in my mid 50s, I started asking myself, so what is it about midlife? I had the worst of times in my late 40s, I had the best of times in my early 50s. What's going on here? And so I started doing research on it. And
on midlife and trying to understand it more and came to the conclusion after having talked with a lot of academics and studied the U curve of happiness that shows that people get happier after age 50 with a bottoming out around 45 to 50 that wow, maybe midlife is not a crisis, it's a chrysalis. If you think about the caterpillar to butterfly journey, the midlife of the butterfly is the chrysalis and it's dark and gooey and solitary, but it's actually where the transformation happens.
So what I started to realize like, wow, maybe midlife has a purpose beyond just being a time when you stumble around and look for a red Ferrari to buy, um, or an affair to have, um, no, maybe midlife is this opportunity for you to go a little deeper, understand yourself a little bit more and on the other side of it, be happier. And. Becca Levy at Yale has shown that when people shift their mindset on aging from a negative to a positive, they gained seven and a half years of additional life, which is the biggest.
Chip Conley (04:26.052)
positive intervention you can do in life. There's nothing, changing your diet, stopping smoking, starting exercising, none of them have a greater impact than shifting your mindset on aging in terms of additional longevity. So that's what led me to ultimately creating MEA, the Modern Elder Academy, the world's first midlife wisdom school.
Greg Moran (04:47.73)
So Chip, I'm curious because you went into Airbnb at that time and you were, and you said the guys were kind of calling you the modern elder and things like that, right? And how did that happen? That's right. Well, it happens to Peter and I all the time. It's all right. You get used to it. But I'm curious how, if you reflect back on it, that influenced your approach to helping
Chip Conley (04:59.869)
They're making fun of my age.
Peter Dean (05:05.866)
Never, never happens to me.
Greg Moran (05:17.362)
lead that business and also I think, you know, helping mentor really young founders that were really doing something pretty incredible.
Chip Conley (05:19.599)
Yeah.
Chip Conley (05:26.66)
Thank God it worked. I mean, it could have been just, excuse me, a shit show. Because I've been running my own company for 24 years and I was used to being the CEO. I was used to being in charge. I was used to having my name and picture in the paper. And I now I'm joining these young Turks who are 21, 23 years younger than me. And I'm twice the age of the average person in the company. I was 52 and the average age was 26. And so...
Greg Moran (05:31.879)
I'm out.
Chip Conley (05:56.244)
And they called me the modern elder because they said, Chip, you're as curious as you are wise. And that was really interesting. So curiosity and wisdom, like how do you live your life, you know, tapping into both, especially as we get older. And the way it worked was the following. Number one is Brian Chesky, who was the co-founder and CEO, who really wanted me to be his in-house mentor. He had an appetite for learning. And, you know, instead of being the know-it-all
29 year old who said, okay, you know, Chip, you're not gonna teach me anything because, you know, you're old and you're a bricks and mortar hotel, you're in, we're a tech company trying to disrupt the hospitality industry. He instead said like, I wanna understand everything, Chip, teach me everything. And so because he sort of rolled out the red carpet for me to teach him something about hospitality, travel, entrepreneurship, leadership, emotional intelligence.
I started teaching, but I actually realized that I could be a mentor, not just a mentor. A mentor is somebody who's a mentor and intern at the same time. So I taught Brian a lot of EQ and he taught me a lot of DQ, digital intelligence. And I learned as much from him as he did from me because I was a fossil. I was 52 years old, I never worked in a tech company before, didn't understand UX, UI, or frankly working with venture capitalists.
Peter Dean (07:10.626)
Mm-hmm.
Chip Conley (07:24.48)
Even though as a hotel, you were based in the San Francisco and Silicon Valley, I didn't have venture capitalists and that's a whole different breed of investor. So long story short is I think where I was really helpful is that I got my ego out of the way, I right-sized my ego so that I didn't feel like I had to be in charge. I was no longer the sage on the stage. I was the guide on the side and I was, I was very comfortable being the CEO whisperer. My job was to help Brian.
to be the most effective CEO he could be, even though he came from a background that would not suggest he would be the CEO of what ultimately became $120 billion company. It's not worth that now, but it's still worth a lot, like maybe 80 million, 70 billion. So long story short is I had to really make a shift that I was gonna be curious and wise. I was gonna be teaching and learning. I was gonna be...
Greg Moran (08:09.618)
Yeah.
Chip Conley (08:23.028)
More than anything, my definition of success was how successful Brian could be. And I'm proud, what, three and a half years later, after going IPO, Brian is still the CEO of Airbnb. And out of the Fortune 500 CEOs, he is the only one who doesn't have a business background. He's the only one who came from the creative world, having gone to Rhode Island School of Design and frankly had no background in business at all.
Greg Moran (08:51.69)
pretty, it's pretty amazing. You know, we did a podcast, we had a guest on actually released it on Monday. And Carson Tate is her name. And she talked about this concept of radical self awareness. And it just, it just when you were talking about it, that's what kept going through my mind, right? Because both for you and for Brian, I mean, it speaks volumes about his willingness to sit there and say, teach me everything, right?
Chip Conley (09:13.881)
Yeah.
Greg Moran (09:21.938)
that I don't know what this really requires. And it speaks volumes about your willingness to say, I can be curious and wise at the same time, right? And I think it just, it really just.
Chip Conley (09:32.485)
I don't know what you're talking about sometimes. I'd say, hey, your lingo, I don't know if it's millennial lingo or it's tech lingo, but I'm not understanding it. So help. Yeah.
Peter Dean (09:41.716)
Yeah.
Greg Moran (09:43.337)
I don't know what the hell you're talking about.
Peter Dean (09:46.874)
Chip, do you think those questions helped kind of keep them like founded in something that maybe allowed them to bring something to market that was different?
Chip Conley (10:00.472)
When you join a company and everyone's trying to be the smartest person in the room, and I come to realize I need to be both the most curious person in the room and the wisest person in the room. And when I'm dumb and don't understand what's going on, I got to be curious. And when I understand what's going on and I can see the holistic picture better than a young person, because actually one of the things that gets better with age, and I wrote about this in my book, Learning to Love Midlife.
Peter Dean (10:16.579)
Mm-hmm.
Chip Conley (10:29.392)
is that as we get older, the blinders come off. And it's called crystallized intelligence. Arthur Brooks wrote about it from Strength to Strength. We are better able to think holistically. And there were so many times at Airbnb where the young people who were fast and focused and quite brilliant were missing the big picture. They were not connecting the dots. My job was to be the truth teller and help them see the blind spots. And
Peter Dean (10:41.538)
Mm-hmm.
Peter Dean (10:49.556)
Mm-hmm.
Chip Conley (10:59.092)
and be willing to, yeah, you know, sometimes be wrong. You know, one of my friends said, I felt at times like I'd be in a meeting and I'd bring something up, and I thought I was putting out a blind spot, but then as it turns out, I was wrong. And I felt like, oh man, I was like going up to the plate and, you know, or going out to the basketball court and missing a free throw, missing the rim completely. Like, oh, I'm so embarrassed. And I kept saying to my friend, like, you know what?
When it comes to basketball, I think maybe a third of the time, I am in a, I'm showing the blind spot, but two thirds of the time I'm not getting it. And I feel like the idiot is only hitting 33% of his baskets. And then my friend said like, well, no, you're playing baseball, not basketball. You're hitting three 33 at the plate. Um, and you should be proud of that because frankly, when you get to the plate, you hit home runs and I was like, Oh, it's a whole different perspective. Um, but yeah, I think I have.
Greg Moran (11:54.578)
Right.
Chip Conley (11:57.168)
I think I had a really profound impact on the trajectory of the company. But it wasn't me alone. And again, the fact that I was learning as much as I was teaching made it more interesting for me, quite frankly.
Peter Dean (12:05.998)
Mm-hmm.
Peter Dean (12:12.878)
Mm-hmm. Yeah, that's so in the corporate startup world, like there's emphasis on this relentless drive. And what you're talking about is like finding comfort in your own skin and then not solely being defined by achievements. How do like you obviously talked about yourself doing that in a way to kind of come to help them. How do people in that world do that? How do people go through a process to kind of become more?
Chip Conley (12:32.165)
Yeah.
Chip Conley (12:41.752)
Yeah, well, I mean, you have to adapt, you have to evolve. I wrote a book called Wisdom at Work, The Making of a Modern Elder, about my Airbnb experience. And I said, there's four steps to being a modern elder. First, you have to evolve, then you have to learn, then you have to collaborate, then you have to counsel. The last thing, counsel, is what you do when you're perceived as the mentor. It's like, you give advice and you give feedback and you ask good questions.
Peter Dean (12:43.661)
You know.
Peter Dean (12:49.247)
Great.
Chip Conley (13:08.428)
But you do that last. The first thing you have to do is you have to evolve. And what I had to do is I had to evolve from, again, having the big ego CEO, to shifting my definition of success. And that's not something that happens easily. Thank God I had a good friend who's a coach and she just helped me.
to see some things. And my dad once, I was hiking with my dad and I was like, kvetching about the first few months being there and felt like I was, so like my last job in my career I was gonna be failing at, which would be at Airbnb. And he said, how can you turn your fear into curiosity? And I was like, oh God, that word curiosity comes up again because that's what the founders said. They liked about me as being curious. And so I think,
So much of it is learning how to shift one's mindset And this is something with that, you know Part of the reason I started MEA is because I wanted to create a midlife wisdom school where people in their 40s 50s and 60s Could have tools and a support system that helps them to make that shift I had to do it on my own but with help from my friend who was a coach But there was no roadmap for me. I want to create roadmaps for people
Because a lot of us are going to work into our sixties, seventies, maybe eighties. And we are going to have to evolve our mindsets over and over again. Cause if we keep doing it the way we've always done it, um, it isn't going to work. Uh, you know, and, and we also don't give ourselves the opportunity to learn something new. So, so much of it is the evolution of that mindset and there's a fixed mindset. There's a growth mindset, a growth mindset. So when you're really focused, not so much on proving yourself, but improving yourself and, um, and that's what I was trying to do.
Greg Moran (14:57.85)
It's funny, you know, when I was reading the book, you talk, I think, in the, um, in part of the book around with MEA and the fact that, you know, you've got, you said forties, fifties, sixties. I mean, you, I think at one point you reference even people younger in their career, right, coming out of Silicon Valley and getting involved in MEA and
Chip Conley (15:13.908)
Oh yeah. We've had 25 year olds. I mean, we have like, yeah.
Greg Moran (15:18.626)
And, you know, talk about that a little bit because that it's kind of what you're, I think, getting to there is sort of this redefinition of what a professional life looks like, right? Where you've got 25 year olds saying, look, I'm at this midpoint of my career. I'm at this probably more of an inflection point in my career, right? Yeah. So I'm curious to talk about that a little bit.
Chip Conley (15:27.47)
Yeah.
Chip Conley (15:36.396)
Inflection point. Yeah. So, so listen, let's Tom Brady was a modern elder in the NFL at 42. And if you're a software engineer at 35, you're probably a modern elder in Silicon Valley. If you're a fashion model at 30, maybe. But yeah, people sometimes don't come because they feel like a modern elder, even though that's the name of the organization.
Peter Dean (15:37.952)
Mm-hmm.
Chip Conley (16:02.288)
Modern Elder Academy, also known as MEA, they tend to come when they're navigating transitions in their life. And you can be navigating transitions in your 20s, 30s, at any point in your life. And so one of the key pieces of curriculum we have is how do you navigate a transition? What are the three stages of a transition? What are the coping mechanisms during each of those stages? And that's valuable for anybody at any age.
But in an era of AI, artificial intelligence, a growing number of knowledge workers are feeling obsolescent. And who knew at 35 that they would be feeling obsolescent? So there's a sense that they have to figure out how to remake and reinvent themselves. And so that's why one sixth of the people who come to MEA are millennials. And the average age of people coming is 54, but...
Peter Dean (16:42.189)
Okay.
Chip Conley (16:57.592)
We have lots of people who are 42, 43 and younger.
Greg Moran (17:01.874)
Yeah, it's pretty, you know, it is, it really, I think resonates a lot with me and sort of where, you know, I am in my life and coming off of a startup that got larger and CEO of a larger company. And, and then kind of making that transition, right. That, you know, at 50, um, making that transition point into, do you kind of hang on to the CEO thing, right? And, you know, try to
Chip Conley (17:21.944)
Yep. Hehehehe.
Greg Moran (17:30.202)
make another run or do you kind of transfer that into or trans, I guess, sort of transition that into, you know, being more of that elder being more of the teacher instead of the doer. Right.
Chip Conley (17:42.892)
I think it varies. It varies because I call it same seed, different soil. Over the course of your career and your life, you are building a seed. You are building a seed full of mastery and wisdom and a gift that you have. Often we don't understand our gift. And that's one of the tragic things in life. I like to say, there's a David Viscott quote, the purpose of your life is to discover your gift. The work of life is to develop it. And the meaning of life is to give it away.
So I think that the key is to figure out what is that gift, what is that seed? And then same seed, different soil means like, okay, there's a different industry you can be in, there's a different role you can be in, but you still bring with you all that wisdom and that mastery and gift that you have. So we get often very caught up in like the functional LinkedIn titles we have.
I'm a CEO and therefore I've got to be a CEO. I'm an extra. If I go and do something else and it's not a CEO, I'm going backwards. No, I mean, that's very limiting. That means that you don't have opportunities like I did at Airbnb. Where ultimately I was reporting to my mentee. Brian was 21 years younger than me, but I reported to the guy, even though I was mentoring him. So I had to be willing to...
Greg Moran (19:00.135)
Right.
Chip Conley (19:02.764)
to do something like that. And thank God I did. It turned out very well for both the company and me. But I don't know that it's always gonna be, okay, I've been the CEO of something and now my job is to just mentor people. You may have a new business idea and you're gonna have a co-founder and the co-founder is 20 years younger than you and that's what you're doing and you're co-CEOs or you're the CEO and he or she is the COO and it's like.
I wouldn't limit myself there. I would say be opportunistic about what's coming along, but know that the way you're gonna operate in your life, in your 50s or 60s is gonna be different than it was in the 20s or 30s or 40s. And if you don't operate differently, you're not evolving. And again, that evolution piece here is essential because I don't wanna operate the way I did when I was 30 years old as a CEO of my boutique hotel company. I'm...
33 years older than that now and a lot wiser and I have a lot more I can bring to the table, but I also don't want to be so obsessed with what I, you know, being the CEO of the company at age 30 and having my full self-esteem defined by the success or failure of the company. At 63, I can live with the fact that, you know, if something doesn't work out well, then I still, I'm not going to like crumble. So you know, there's the...
This is, again, this is a lot of what I write about in learning to love midlife, the 12 reasons why life gets better with age. One thing that gets better with age is we have perspective and the world doesn't revolve around us and we know that.
Peter Dean (20:37.451)
Mm-hmm.
Peter Dean (20:42.09)
Yeah, people get stuck in that mode, because it's fed to them too, to some degree, like your CEO. And how do they shed that? How do they start shedding that personally and professionally? People come to your academy, and this is part of what they get help with. But what are some of the things that you see that they do to shed it?
Chip Conley (21:01.25)
Yep.
Chip Conley (21:06.144)
Well, learn a couple thoughts there. One is having a full dimensionality in your life. If your life is very one dimensional, you're going to hold onto that CEO role and title even more because there's not anything for you to fall back on. And so, you know, one of the first steps towards saying, okay, I need to, I need to move on from this at some point is to say like, oh, I'm going to start like doing some photography or I'm going to be a better dad.
Peter Dean (21:19.061)
Yes.
Peter Dean (21:23.504)
Mm-hmm.
Chip Conley (21:34.32)
Or I'm going to get involved in a political campaign for a friend who's running for something. Or because that full dimensionality of your life means that you can start to step away from all of your identity being defined by your business card. Secondly, learning how to become a beginner again. This is something we do at MEA. We help people learn how to surf. We help people learn how to bake bread. We learn how to help people learn how to do improv and how to write.
you know, in a journal and, and to do a yoga class. And like, when you become a beginner again, that humility around learning how to, how to be, have beginner's mind is really valuable. Um, not because it means you are going to become the best baker in the world or the best surfer, but because it gives you the ability to realize you can try new things and you know, what happens as we get older often.
is we narrow our focus and therefore we get bored. You know, we're at 55 years old and we're like, I'm bored silly. And it's like, well, when's the last time you tried something new? It's like, oh, I haven't done that, I haven't had time to. Okay, make some time, so.
Peter Dean (22:34.401)
Yeah.
Greg Moran (22:46.95)
Yeah, we're laughing. We're not laughing at you. I just did a, yeah, I just did a five day surf camp in Costa Rica. So I'm going to totally disagree with you, Chip. All of the rest of what you said makes total sense. The surfing thing, that is bullshit. Like total bullshit. Like that all I did, I actually loved it. I'm kidding. But all I did was.
Peter Dean (22:48.082)
If you're watching me laugh because Greg, Greg just told me about surfing. So.
Chip Conley (22:55.754)
Thank you. I'll be back soon. Yeah.
Chip Conley (22:59.964)
Oh my gosh.
Chip Conley (23:05.239)
Yeah.
Chip Conley (23:10.645)
You didn't enjoy it.
Peter Dean (23:14.274)
He... he did.
Greg Moran (23:16.402)
five days of the, yeah, but you talk about beginner's mindset, like five days of the most intense physical abuse I think I've taken since I played hockey. I'm just, I'm totally kidding. Well, I mean, I'm not kidding about the physical abuse, but I am kidding about the bullshit part. It was, but you're 100% right. And I think that's, I mean, that was the whole
Chip Conley (23:26.633)
Yeah, yeah, yeah. So you know what? It doesn't have to be surfing.
Peter Dean (23:27.83)
He got planted in the sandbar.
Chip Conley (23:44.514)
Mm-hmm.
Greg Moran (23:46.554)
You know, it was just something I ski and do a lot of mountain bike and do a lot of other things like that. But it was something that, you know, it is where you are. It's a rare thing. I think when you get to, you know, our ages on this call, it is a rare thing when you do something you have truly never, ever done. Right. Or you are completely at the mercy of somebody trying to teach you.
Chip Conley (24:07.833)
Yep.
Greg Moran (24:12.29)
every single basic, whether it's surfing or it's an instrument or whatever it is. And I think that was the power in it for me, right? It wasn't like, you know, my pro surfing career is really not going to happen. So, but that was the power in it, you know, to just be able to open your mind in an entirely new way. And it doesn't happen a lot. You know, I think for a lot of people, unfortunately, when you start to get up in, you know, when you get to middle age, you just, the walls keep closing in.
Chip Conley (24:23.428)
Hehehehe.
Chip Conley (24:34.008)
Yeah.
Chip Conley (24:38.636)
Well, there's a variety of things that are happening. The walls are closing in partly because we get more one-dimensional, get very focused. You know, the spinning plates phenomenon, especially in our 40s with our work and our family and all of the obligations. We've been taught that accumulating is what we're supposed to do. And it's around age 45, 50, you realize I've accumulated so much, I need to start editing.
And it's a really important piece of the process of going through midlife. Because if you're just carrying all the baggage of your life along the way, it just weighs you down. And so learning, one of the things we do at MEA is we do something called the Great Midlife Edit that helps people get rid of what's not serving them anymore, or whether it's a mindset or an archetype or an obligation or a relationship that's like, you know what, I need to sort of.
dose that down or get rid of it altogether. Very important because what you do by doing that is give space to try something new. And curiosity and a passionate engagement for life are two of the most correlated, directly correlated qualities about people who live longer, healthier, happier lives. Peter Drucker would study a new topic every two years. It had nothing to do with being a business school professor.
And in so doing, he learned that, oh my gosh, curiosity is like the fountain of youth. And so I believe that's the case, and being curious and willing to try something new is essential.
Greg Moran (26:19.657)
Yeah, totally agree.
Peter Dean (26:21.39)
That's cool. So this is something you talked about before. What are some ways seasoned leaders can kind of pollinate their wisdom on the younger generations? In the startup scene, you obviously did this and foster that culture of learning and growth.
Chip Conley (26:34.508)
Yeah.
Yeah, I think the key is to understand what you have to offer. So understand your mastery and your gift. Realize that actually the best way to deliver that is not necessarily giving advice or feedback, but it's asking great questions. So learning how to ask great questions is to me, you know, Jimi Hendrix said a long time ago, knowledge speaks and wisdom listens. And being able to become a great listener and learning how to
pose a question that's catalytic. We use something at EMEA called appreciative inquiry. You can Google it and determine if it works for you. And it's a great way of asking questions. So that's a key thing. Know what you have to offer. Learn how to ask questions. Because if you're just the guy who is saying, hey, this is how the world works, you're gonna get an okay boomer hand in your face at some point, because you're the know-it-all.
And then finally, make sure that you have mentees who have an appetite for learning, and you have maybe even a common definition of what makes success in this mentorship relationship. Because there's nothing worse than being open to being a mentor and then your mentee just blows off that meeting you're supposed to have three times in a row. And it's like, okay, well, why am I wasting my time on this? So.
you know, having someone who is really eager to learn from you and having clarity like, okay, how, you know, what's the structure of this? Maybe let's have a conversation once a week, or is it once a month? And three months from now, how will we know that it succeeded? You know, what is it that you want to learn that I can be able to deliver to you? So these are some of the questions you want to ask.
Greg Moran (28:29.47)
Yeah. You know, it's funny, I think as you and I see this a lot in kind of coaching or mentoring that I do with founders, you see this sort of loss of, I guess, joy or purpose, very often in entrepreneurs and founders as they start to get, you know, this passion that they had at 26 when they were leading their hospitality startup or, you know, whatever it is, it, as they get older, it erodes.
right? And there's almost this kind of resentment that starts to build as they get into midlife when they're still running those businesses. How do you coach somebody who may be kind of hitting that point to kind of either, I don't know if the right way to ask this is like, we find, you know, reclaim the joy or the purpose or is it something else, you know, because you do. I see it a lot in kind of old, you know, older
Chip Conley (29:04.331)
Mm-hmm.
Chip Conley (29:17.05)
Yeah.
Greg Moran (29:28.014)
older founders have been at it for a long time.
Chip Conley (29:30.42)
Yeah, I mean, there's really, I think there's two answers to this. One is when someone needs to reclaim the joy and get clear on why they started it in the first place. So for me with, you know, when you call your company, Joie de vivre, which means joy of life, it's like, daily basis. I'm like, okay, I'm not enjoying this. Something's wrong here. But, you know, what I knew is in my work.
Greg Moran (29:49.35)
I'm not sure if you're gonna be able to do that.
Peter Dean (29:55.042)
very aspirational.
Chip Conley (29:56.784)
Yeah, in my work, I realized that I started Joie de Vivre because I was looking for creativity and freedom. And by the time I had been running it for 22, 23, 24 years, I didn't feel much creativity or freedom. And it was that question I asked myself is what led me to do this in the first place? And is that still there? Or has something supplanted it? Is there something new?
I mean, I could have said like, if you'd asked me 10 years earlier, I'd say like, yeah, it was creativity and freedom, but I also wanted to create a great culture and I wanted to learn about leadership and that meant a lot to me. But by the time I got to the end of it and I didn't wanna do it anymore, I felt so lacking in creativity and freedom. And that was one of my ways to say like, I need to exit. But sometimes, you know, it's like a re-ignition of like, okay, the thing that I loved originally, how do I find that again? And sometimes you can find that.
But sometimes it means it's time for the business is at a stage where you're not the startup CEO anymore. You're the maintenance CEO and that's not interesting to you. So understanding that sometimes the qualities that you need in a CEO in the first five or seven years are very different than what you need in years seven through 15. So that's an important thing to realize as well.
Greg Moran (31:18.362)
Yeah, no, I think that's great advice.
Peter Dean (31:21.166)
That's so cool. So we have a lot of early founders. There's founders like us, there's a number of them, but there's a lot of early founders that listen to this. What would you advise to be to them as kind of an early founder that's at that stage that you just described in the early days to kind of be prepared for this transition in the years to come?
Chip Conley (31:38.537)
Mm-hmm.
Chip Conley (31:44.472)
I mean, I would just say the most important thing is like surrounding yourself with a great team, because it's really easy, especially if you're a founder, to think it all revolves around you and you're the hero and etc. But you're going to have good days and your bad days. And when you're going to have the bad days, you can't just rely on your family and your best friends. You have to rely on some people who you work with on a daily basis. To
be there for you. So building collegial candid relationships with your senior team is really important. One exercise I've been doing at all three of these companies, Joie de Vives, Airbnb and MEA is once a quarter, we sit down as a leadership team and we talk about what was our biggest lesson of the last quarter and how's it gonna serve us moving forward.
And each of us do that individually. And then we have a team lesson of the quarter that we align around, that we say this was our biggest lesson. That process is so beautiful because it allows everybody to be candid and vulnerable about what they've been learning and what didn't go as well as expected. But most importantly, to focus on how it's gonna serve them moving forward. So having a team like that is really helpful because when you're in a rut and you're maybe the rut last six months or a year,
You really need to have the rest of your team stepping up to help you. And it's easy as the CEO or the founder to feel like you can't be honest about that because you're the one who's supposed to be the superhero. But that's also what leads to a lot of psychological damage for entrepreneurs is when they feel, and sometimes suicide, because they ultimately get to a place where
they need an escape and they don't have one because they haven't set one up with their team.
Greg Moran (33:40.082)
Yeah, I think that's.
Peter Dean (33:40.802)
So do you think that Superman thing is like this feeling of just having to win or just having to be the one that saves everything, but when you see it's not really happening, that's what you're talking about, right?
Chip Conley (33:53.908)
Yeah, I mean, well, or you are doing it. You're over and over again. You're the superhero who's saving the day, but you're just burning yourself out. Your team is tired of you because, you know, you always step in right before they're about to fix something. And yeah, I mean, I understand this quality very well. This is hand in the air. I do that a lot. And...
Peter Dean (33:59.98)
Yeah.
Chip Conley (34:19.317)
you know, thankfully as you get older, you have pattern recognition and you start to say like, oh, I'm doing it again. But yeah.
Peter Dean (34:26.91)
Yeah, very cool. That's great advice.
Greg Moran (34:29.894)
Yeah, it is. I think that's a... And as we kind of wrap this up, I think that... It's so important, I think, that the last piece of what you were saying is so important for founders to realize as early as they can, right? When you're stepping in and when you're trying to be that Superman, I mean, the only thing it's going to lead you to is that burnout.
in a much shorter period, we all get burned out, right? I mean, at some stage we all get burned out, but you're just bringing that, you're making that wick so short at that point that it becomes hard, it becomes hard for them, it becomes hard for the team. And I think, and especially when you start to get into your kind of middle years and you start to itch for something more and to be in that situation nonstop is a really difficult thing. So, Jeff, it's really amazing to have you here.
Chip Conley (35:24.932)
Yep.
Yep.
Greg Moran (35:28.994)
loved the conversation. If you're listening and you haven't bought the book, it's everywhere, Amazon, I'm sure all your local bookstores, Learning to Love Midlife is the name of it. And if you don't follow Chip on social media and everywhere else, I know Chip, we were just about to go on and we saw you were like live on LinkedIn or something just a couple minutes ago. So you're all over the.
Chip Conley (35:55.756)
Yeah, LinkedIn, I'm pretty active on my LinkedIn profile. So you're welcome to look, I have a daily blog and I post it there. So yeah, you can, that's probably the best place to see me on social media. And then there's [chipconnelly.com](http://chipconnelly.com/) and the MEA website is [MEAwisdom.com](http://meawisdom.com/). And we do private groups, by the way, at MEA as well. We do public workshops, but we have lots and lots of private groups, YPO and all kinds of other organizations that do private groups at our Baja campus or our Santa Fe campus.
Greg Moran (36:26.354)
That'd be amazing. Yeah. So if you haven't, if you haven't checked out MEA, do it. If you haven't checked out Chip, do it. Super thrilled to have you here today, Chip. And appreciate you coming out. We'll see you on the next edition of the Founders Attorney podcast.
Chip Conley (36:39.181)
Yeah.
Chip Conley (36:42.744)
Beautiful. Thank you.