Ryan Berman talks to thought leaders from around the globe in business, sports and entertainment to uncover what it means to be courageous in today's world.
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Chip Conley - Founder of Modern Elder Academy

Chip Conley – Founder of Modern Elder Academy

10 years ago, when the founders of Airbnb asked Chip Conley to be their mentor, he had his doubts. He could not see his place at a young-blooded tech start-up where the average employee was half his age. But Chip is not one to back down from a challenge, and with the help of Airbnb co-founder Brian Chesky, he began embracing his new role as a “Modern Elder”. Chip is a self-proclaimed Zeitgeist Surfer, a rebel hospitality entrepreneur, a bestselling author, and the Founder of Modern Elder Academy, the world’s first midlife wisdom school that helps people cultivate and harvest their wisdom.

Episode Notes

In this episode of the Courageous Podcast, host Ryan Berman and Chip Conley explore what Chip is currently afraid of. They also discuss Chip’s time at Airbnb, the power of mentorship, and how the “great midlife edit” inspired Chip to launch The Modern Elder Academy.

(Intro music 0:26-0:44)

Ryan Berman  0:45

So, it was late 2019 when I learned that I was gifted the opportunity to be a keynote speaker for HSMAI, which is for those who don't know the Hospitality Sales and Marketing Association International. And, I call up my buddy Stan Bromley, and if you know the Bromley name, Bromleys are like four seasons. There's a whole tree of them. They have Mark Bromley there now. And I'm talking to Stan, I'm just trying to get some insight on this audience, and Stan’s like, “You got to talk to Chip Conley.” I’m like, “Who's Chip Conley?” He’s like, “You don't know who Chip Conley is? Go look up Chip Conley,” which is very Stan by the way it is.

Chip Conley  1:26

It is. (Laughs)

Ryan Berman  1:27

And he ends up introducing me to chip, and I got to tell you, Chip, at this moment in time, it's pre-pandemic days which feels like a decade sometimes ago. And you were gracious enough to give me a half hour, and I'm like, “Chip, what am I stepping into?” And I remember it being a quick conversation but a meaningful one. And I was actually, to be honest -- this is a courageous podcast -- I had a little fear going into that call. I remember listening to your audible of your book to be really ready to talk to Chip. You're on your journey, I'm on my journey. You're doing some amazing, amazing things with Modern Elder Academy. For those who haven't studied Chip's background, just amazing work in hospitality. And then, you get an opportunity with Airbnb. I'm cutting corners here just for the spirit of time. But let's go back because we're going to cover all that. Let's go back to before Chip Conley is Chip Conley, you’re just Chip, what was it like growing up being Chip? Where'd you grow up, and how did you happen?

Chip Conley  2:37

Well, how did I happen? I will have to ask my parents about that. They're still both living. My dad turns 85 next week and my mom's turning 85 in January.

Ryan Berman  2:45


Chip Conley  2:46

I was their first child. They were both first children and their families, so you can see that I was probably hyperactive responsible having been the firstborn of two firstborns. Both of them went to Stanford. And being Chip with being a chip off the old block. I was Stephen Towson Conley Jr. My dad was Stephen senior. And so, my dad was a Marine Captain so he's a pretty hardcore dude. And, at times, I shrunk in his presence because he was a really old school, very by-the-book kind of guy and I was more of a creative person. I was an introvert when I was young. And then, at some point around early adolescence, my parents told me like, “Chip, if you don't do a better job of making friends, we're going to send you the therapy.” I was like, “Oh, no therapy. That sounds like jail.” I had no idea what therapy was but it didn't sound good. And so, in my teen years, I learned how to become a social Alchemist, a mixologist of people. And I say that not to say that I'm not a genuine person. The introversion piece of me was still there. That's part of the reason I've written five books because I like to write and writing is a very solitary task. But long story short is my early upbringing in Southern California was as this person who went from being an introvert to an extrovert. Was very achievement-oriented. And went to junior high school and high school in the inner city. I went to Snoop Dogg's High School. He's 10 years younger than me. But bottom line is I was the curious white boy in my high school. So, I learned a lot and then I went to Stanford. Undergrad, I went to Stanford Business School. And that will take you up to about the time I started my first business.

Ryan Berman  4:30

Let's talk about the books real quick. When you write, what's the process look like? Is there a time limit? You've done this long enough to know how long it probably takes you to write a book. What's your process like, and how long does it take?

Chip Conley  4:45

Well, the process is sort of interesting. It's like a pregnancy. There may be a romance going on with an idea, but from the point when I decide I'm going to write the book, it's nine months. It's a process of about nine months. I’ve done it faster, but I’ve also done it a little slower. So, nine months is about the average. And I tend to research my books, my books are not just Chip flowing his own prose about my life. The books are really at the intersection of psychology and business. I tend to write well early in the morning. I say that my writer wakes up before my editor, meaning when I wake up at 4:30 in the morning and I'm just writing for two or three hours, there's no filter. It's just me flowing. Whereas, as the day goes on, there are more distractions, and my editor kicks in in a big way. And what does that mean? It just means that I don't just flow it out. I can edit it later in the morning. But if I'm trying to write at nighttime, or in the afternoon, not as good because I feel distracted more, plus it's more labored. These ideas come to me along the way. The last book was called ‘Wisdom at Work: The Making of a Modern Elder.’ And that became my story of what it was like to be the old guy at Airbnb 10 years ago when the founders asked me to come in and be their mentor. So, I wanted to write about it. And each of these books I've written has had a little… It's got a strong personal story, but then, it's got a foundation of intellectual and, sort of, thought leadership to it that is meant to be helpful to the reader so it's not just a memoir.

Ryan Berman  6:22

Yeah. I'm taking notes in my mind because I've only written one book. I'm nowhere near five, but I'm starting to process the next one and I'm sure you feel the same way. You can spend your time in many, many ways. So, if you're going to write a book, it better be interesting to you, you have to passion for it. So the baby is born, but then, you have to nurture for the baby, there's a lot more work to be done after the nine months of writing. I felt like mine was more like a documentary, so huge heads nodding when you talked about there's a research component, and then the writing component. Last book question, what is your favorite part about the process? And then, what is the part that just drives you mad?

Chip Conley  7:15

Well, I’ll start with the part that drives me mad, the part that drives me mad is publishers. As Seth Godin, a good friend of mine I went to business school with said to me long, long ago, he said, “Chip, if farmers treated their cows like publishers treat their authors, they would never give any milk. The farmers would never give any milk.” And, it's not the people that are the problem, the people are great in the publishing industry, but the industry is sort of broken. And it takes way too long to get a book out. They have cut back so much on what they do. You're doing your own PR. I've had New York Times bestseller, I've had Wall Street Journal bestseller, and I've had a lot of success in writing, but still, it's tough. In terms of what I like the most, I love the fleshing-out of an idea. Something that feels like a little kernel and it's like the early stages, and I feel like it's something that hasn't been done before. So, it's a topic, and a point of view on it, and maybe even a framework. My book ‘Peak: How Great Companies Get Their Mojo from Maslow,’ that's a framework.  I'm not a consultant, so I don't live in that world, but that book is a practitioner's guide that very much a consulting model that any company could use. And so, that's what I love.

Ryan Berman  8:40

I thought your writing was super thoughtful. You step into the shoes of the audience. I'm like, “Yeah, that's what you want to do.” Slow down, and in some ways, hold the hand of the audience and be practical about it. And it's funny because I do say I'm a consultant still. I like consulting. It does bother me when I'm being asked to go on a stage somewhere, and someone's written a book and they've lived their ideas in the land of theory, and you’re like, “Well, where's the practicality of that? Do they ever bring that to life?” And so, I love the way that you're thinking about, “Hey, is this really practical?” And you've done this for a long time and I mean that in the best possible way.  I'm like, “How's he going to respond to this question?” Do you see yourself as a hospitality guy that gets marketing or a marketer who understands the importance of hospitality?

Chip Conley  9:32

I would say I'm a marketer who understands hospitality, and I'm deeply connected to hospitality, but I love to zeitgeist surf, being a zeitgeist surfer. And if you’re a zeitgeist surfer, you’re sort of imagining something that hasn't been done before whether it's a certain kind of boutique hotel, or creating the first boutique campground in the United States, and things like that. The Modern Elder Academy of Midlife Wisdom School, my first boutique hotel years ago. I just love that. I love having a premise, and then, being able to go out and prove that it works. And it doesn't always work. I have had restaurant concepts that just seemed like a great idea, but either the idea was faulty or the execution was, and it didn't work. So, you learn from those as well.

Ryan Berman  10:20

Those are so terrifying, aren't they? When you're like, “I have a hunch. And I think I have enough data.” Same thing, I'm selling courage. Really? To some corporations, the last thing they want, or think they need… They're just trying to get through the weeds of their emails. “Courage, how does that play?” So, I've definitely had that feeling, like, “Am I on the right path?”

Chip Conley  10:44

Yeah. It's a hard one. My friend Seth Godin wrote a book called ‘The dip.’ And the dip was this... And I haven't read it in ages, but it was the idea that you have an idea and you and you get it out there. And it might have some initial positive or not, but there's a dip at some point. And it's in that dip that you have to understand whether this is a short-term fad, long-term trend. Whether this idea has a robust long-term future ahead of it. And it's hard because there can sometimes be pieces of evidence along the way that suggests maybe you're on the wrong path. And that's why feeling like you have a calling. If you take our relationship with work and put it into a pyramid with the job at the base of the pyramid, career in the middle, and at the top, at the peak of that pyramid is a calling. And when you feel like you're living your calling, and you're pursuing a purpose that feels noble, and you're in the middle of your Ikigai -- the idea of what do you do? What do you love doing? What do you do well? What can you get paid for? And what does the world need? -- Right in the bullseye, then that's when you have to sort of say, “I have to be patient.” Sometimes I’d be patient and persistent. It's a combination of those two.

Ryan Berman  12:04

Job, career, calling. And I think the older you get, the closer you get to calling.

Chip Conley  12:13


Ryan Berman  12:14

By the way, if you figure this out before me for; Bravo. I got into ad agency life right out of school, and it was survival mode. You're not totally sure who to trust, you trust everybody, of course. You want to please everybody. You want to prove that you belong. You don't know anything. You think you know everything, and it takes a while before it slows down. We're going to get to Airbnb here in a hot second, but I'd love to know along the way when you think about the mentors that you ran into. And, of course, mentors are funny things because when you run into them the first time, you're not like, “Ding! Mentor,” but over time, like, “Oh, wow. If I really step back, that human really helped me.” Did you have a mentor a few in business that you just turned to and loved?

Chip Conley  13:05

Let me tell you that the mentor that is most meaningful to me was a guy from Dallas named Herb Kelleher. So for 37 years, he was the CEO of Southwest Airlines and one of the co-founders. Long story short is about three years into me starting Joie de Vivre, my boutique hotel business that grew to 52 hotels around California, I was seeing that, “Oh man, the thing I need to really understand and we need to invest in as a company is culture.” And as Peter Drucker said, “Culture eats strategy for breakfast.” So I wanted to say, “Who is a business leader that I really admire that I can learn from,” and there wasn't anybody that came to mind in San Francisco. And then, I just realized Southwest Airlines is this fascinating little company that has an amazing culture. So, I called Dallas one day, this is 1991, I believe. My company was four years old at that point. And I got a hold of Herb Kelleher's assistant named Colleen Barrett. And Colleen was so nice to me. She said, “Well, Herb can’t be your mentor, I'm sorry. He's a little busy.” But she didn't say, “What if you wrote a letter to Herb? And if you really build a rapport with Herb, maybe he'll just answer your letters when you write them.” So, I wrote them, asked him a bunch of questions on culture. Three weeks later, I get a letter back from the chairman and CEO of Southwest Airlines answering my questions. And he said at the end, “I really liked the questions you asked because some of them made me think about how do I see culture.” And so, he said, “You can write me once a year.” And so, for 10 years, 10 different letters. I wish I’d saved them all.

Ryan Berman  14:46

That's a book right there.

Chip Conley  14:49

I did save them all. And then, one day, they all were thrown out because they were in a box of things that looked like it was trash. So, I lost all 10 letters. I mean, I have some notes of what I remember him saying. But, long story short is an example of like, okay, mentorship is not necessarily somebody who works with you, or someone who lives near you. Especially in the Zoom era, you can have a mentor from afar very easily. But it also was a real tale of Herb Kelleher. Funny thing about him is that that woman, Colleen Barrett who was his assistant ended up becoming president of Southwest Airlines because he deeply believed that she was better than he was at culture. So, that was the part that was funny to me is that, over the course of time, I got to observe how this man took his executive assistant and built her through the ranks to the point where she was the first woman president of an American airline.

Ryan Berman  15:42

Plus, I'm sure there was immense trust between the two of them, right?

Chip Conley  15:46

Oh, totally, so much.

Ryan Berman  15:47

And how important is that? Like, no trust, Good luck. So, man, I don't know if you’re ever going to stumble into that, but that would have been a great book, like, 10 letters just in the response back and forth. Maybe we would come back with a quip, we'll do a podcast on that, of what you remember in your notes because I can only imagine the gems. So Airbnb, just wow. It's funny, I do take great pride in being an observationist and try to be a good listener. And one of my favorite interviews for ‘Return on courage’ was with a guy named Roger Martin who was pretty high up in IP at Qualcomm. If you look at Qualcomm; 30,000 employees, campuses. Always good to have campuses, right? Plural. And he's going house on fire. House on fire moment. And he would say that there's zombies in the business. These slow-moving things that come in and they're moving so slow you don't think they would actually take down your business, and we all see them. Airbnb; clear zombie to the hospitality business. Like, “Oh, we don't have to worry about Airbnb, this concept. Let's stay focused on what we think is our competitive step.” So, take me, like, first of all, how do you land there? And then what's it like? And did you know right away that this was something?

Chip Conley  17:15

So, here's how it all happened. So, a couple of years after I'd sold my boutique hotel; Joie de Vivre. I sold the brand and the management company. I continued to own a bunch of the hotels. I got this call one day from Brian Chesky. He's the co-founder and CEO of Airbnb. And he asked me if I knew about Airbnb, and I said, “Yeah.” This is 10 years ago. And I said, “Well, I'm a hotelier in San Francisco and you guys are based here. So, of course, I know a little bit about you.” But I said, “Aren't you owned by Couchsurfing?” And that really was not a good first line. Couchsurfing was a struggling little business. It was sort of a nonprofit and sort of a for-profit, but it was struggling. And, of course, Airbnb was, at that time, a tiny business, but it was growing quickly globally. And he said, “Well, can I come over to your house and tell you more about Airbnb?” And he said, “I'll take an Uber over.” And I said, “What’s Uber?”

Ryan Berman  18:08


Chip Conley  18:09

And this is way before the sharing economy was very well known. And he came in, we hang out for three hours in my backyard in my cottage back there. And I just was really impressed by what a curious mind he had. Young entrepreneurs, at that time he was 31. Young entrepreneurs in Silicon Valley are known for their hubris, not necessarily their humility. And I could see humility in him, as well as, I could see the hubris too. But more than anything, I saw a guy who really wanted to learn, and he wanted to learn from someone like me because he didn't know anything about the hospitality or travel industry. So, I joined the company. And it was awkward because I was twice the age of the average employee in the company. And I'd never worked in a tech company before, so they were using a language that was like, “I have no idea what you're talking about.” But after a few weeks there, I had certain times that like, “I got to leave this place because I am the stupidest person in the room.” Brian pulled me aside and said, “Chip, you're our modern elder.” And I was like, “I don't know if I like that.” He said, “Well, a modern elder, Chip, is not just someone who’s old. It's not like an elderly person. Eder is a relative term. You are twice the age of the people here, so you're an elder amongst us. But what makes a modern elder different is they're as curious as they are wise.” And when he said that, I was like, “Oh, wow, that alchemy of curiosity and wisdom. That's really what I've always been.” I didn't know if I was wise, but I knew I was curious. And that's really when I said, “Okay, I'm going to embrace this.” And a lot of my hotel industry people, they had no idea, they didn't know what Airbnb was. And then, once they started to hear it… My first reaction to it was like, “It's not a very good idea. Why would anybody want to stay in someone else's home,” but I was lucky that John Donahoe was mentoring Brian before I was. John's currently the CEO of Nike. But at the time, he was the CEO of eBay. And eBay was sort of like Airbnb. It was a two-sided marketplace where people, instead of selling space like Airbnb, they were selling stuff that people had, and buyers and sellers. And so, John said, “Listen, Chip, Brian is a very curious person, he could learn a lot from you. And this company, Airbnb, will be worth more than eBay in the next four or five years.” And I was like, “That's crazy. I can't believe you're saying that.” And then, I also knew the two other non-founder board members, which is weird. And they were both hot to trot on it. So, I jumped in even though I thought the idea wasn't all that good. But I also knew my role was to help take something that was a little quirky, and weird, and Millennial-esque, and learn how to take it to the mainstream. And that's really what I did. My job was to help mainstream Airbnb. So, people at all ages, all over the world and not just millennials on a budget who wanted to travel to one of the 20 biggest cities in the world, which is what they were doing when I got there. And there are a lot of other people. They would have succeeded without me, but they wouldn't succeed in a different way and maybe not as big as they’ve become.

Ryan Berman  21:18

So, do you have like, “Oh, shit, this is something,” moment? Or when you see all these people that you value taking board seats and also like mentoring, you’re like, “Okay, they see something. I value these people”? Or was there also a moment in time that PR took it over? What do you think?

Chip Conley  21:37

Well, it was about three or four weeks in when I was only supposed to be working part-time and it was clear I was working full-time because I needed the full-time. And so, I had the ‘oh, shit’ moment around that time when I was seeing just how committed the hosts and guests, just how rapidly evangelical the hosts and guests of Airbnb were and that was fascinating. So, because I was in charge of all the hosts globally, I was in charge of a few things. My specific title was head of Global Hospitality and strategy. And then, the mentors of the founders. But I really got to know the hosts and guests quickly. And I was like, “Wow, products that have this kind of evangelism are like Apple, and Southwest Airlines, and Disney. And this is a company that if they can get it right, and mainstream the product, could have the most loyal customers in the world, in the travel industry.” And the truth is that is what happened, but it was also seeing… The thing that was hard for me was, “How do you create a hospitality business where the people delivering the hospitality are not your employees?” Yes there's customer service needs in the company, but the people providing the service were entrepreneurs, and sometimes a widow who just had a bedroom down the hall from her. And so, “How do you make that widow the best host ever?” And honestly, that was the most intellectually interesting time there. It's not about creating a bunch of standards, it's about creating motivational tools, carrots and sticks, that help people to live up to their potential as hosts. And help educate them, like, what are some little best practices that they might not have known about? But at the end of the day, we created a monster when it came to customer satisfaction. And a lot of it had to do with our review system.

Ryan Berman  23:41

I would have had wild anxiety coming from the service business. And, by the way, you look at your resume, it's not like ‘the service business.’ It's like service elevation. So you have to give yourself permission to give up control. However, when the standards are so, I go back to the Bromley conversation, four seasons, there's a standard of service, right? And so, then you go into this world where you have to give up a little bit of that control. And yet, it works because… It's so hard to go back to what do I really remember about life before Airbnb, and trying it for the first time… My bar was so low, like what's the worst that can happen? It's terrible when I check into a hotel. It wasn't that. So I wonder if like, “Okay, bar raised.” Was it like an iterative approach?

Chip Conley  24:40

It was iterative, for sure. And we had great data. Airbnb is a tech company so it's a data company. So, the data was really helpful. If you think about the hotel industry, they outsourced their review system to TripAdvisor. Not intentionally, but generally that's where people… And so, there's a disconnect. So, we were able to have an in-house review system that helps so much in terms of how do we get people better? And what are the metrics to understand a particular host, and how good they are, and where they need some help? And how do we use technology to influence their sense of that? How do we create a super host program that helps people to feel not on the host side, like, I aspire to be that and there's a bunch of benefits to it? And on the guest side, it's a way to filter to sort of, say, the paradox of choice and have all these choices. Well, one way you’re going to filter is to have a super host. And so, it was about psychology and business. And it was hard though, because I didn't know the language. They were talking languages and I had to at 52 years old suck it up and just say, “Okay I'm going to learn to be humble myself in terms of saying, ‘I don't understand what you're talking about.’” I'll never forget one month into it, I was in the meeting of engineers and I was supposed to be just the silent one in the corner observing. And finally, the 25-year-old wizard running the meeting turned to me and said, “Chip, if you shipped a feature and no one used it, did it really ship?” And I was like, “Well, that’s like a philosophical question about the tree in the forest. If you shipped a feature, I don't even know what that means. What does it mean to ship a feature?” And now I understand it really well, but at that time, I had to be the dumb person who sort of said, “I don't understand your lingo.” So, ultimately, for me, it taught me how to become a modern elder. And that's a really important thing because we live in a world where we're living longer, power in a digital society is moving younger, and the world is changing faster. And those three variables have a lot of people 45 to 65 confused.

Ryan Berman  26:47

I mean, I'm 46. So, hearing the story, I kid you not, you give me courage to stay curious and go into spaces you don't know. And I do think innovation, originality is sometimes you're in a deep category and you leap to a different category. It's like, “Wait, nobody plays by these rules here. I worked over there, what can I bring into this space?” But I adore the modern elder story because I never heard that before. And obviously, that's kind of been the genesis of what you're in now. And man, you're in it. And it's a show about Courageous podcast, and you've got the Modern Elder Academy. Can you share a little bit about what that is, and how long you've been doing it?

Chip Conley  27:27

Yep. So, I've been doing it about five years. And it came out of my time at Airbnb when I was writing the book ‘Wisdom at Work: The Making of a Modern Elder,’ and I was doing it on a beach in the beach home I had an hour north of Cabo San Lucas in Baja. And I went for a run one day, and I had a Baja ‘aha.’An epiphany. It was like, “Why is it that we don't help people in midlife understand how to reimagine and repurpose themselves in a world where they're living longer, powers moving younger, and the world's changing faster?” So, decided to create the Modern Elder Academy, also known as MEA, and the world's first midlife wisdom school that helps people to cultivate and harvest their wisdom, and helps them reframe their relationship with aging and move in a direction toward learning how to move from a fixed to a growth mindset. And I didn't know what it was going to be, there was nothing like it out there. And now, five years later, we have 3000 alumni from 40 countries and 26 regional chapters. The courage is still there. I have to have the courage too because I don't pay myself anything, which is fine. I have the money to be able to do that. But it's also because we're still in major growth mode and if I was making a big salary, that would be a drag on the business. And we're growing like gangbusters, but growth costs money, and I'm funding all this myself based upon having earned an enormous amount of stock at Airbnb. But there's times when, especially even the name; Modern Elder Academy, it’s like, “Oh, modern elderly academy, it’s for people in their 80s.” No, no, no, it's like, average age is 54. We've had people as young as 28 years and old as 88 come to the campus for workshop. But the bottom line is that anything with the word elder and playing with the idea of midlife, it’s like, midlife has a bad brand. The only thing attached to it is crisis. And elders sounds like an old thing, and like, anything related to aging… We have anti-aging creams. It's like aging is not something you want to bet on. And yet, what I saw -- because I lost five friends to suicide at age 42 to 52 during the Great Recession, all men -- was we need to help people through this midlife journey to understand how to get to the other side of midlife and have a better and better life and, and that's really what we've done. So, you got to come down.

Ryan Berman  29:58

I'm in.

Chip Conley  29:59

Ryan, you got to come to a workshop.

Ryan Berman  30:02

I couldn't be more midlife, so I'm in. And I honestly, I think part of it is just going through the -- what's the best way to articulate it? I do think it is really lonely to be the leader. By the way, leader doesn't mean of a company, you're leading a family, you're trying to figure this thing out. And there's anxiety knowing you're actually going to live longer because you need more money if you're going to live longer. And I would go as far to call it a clarity epidemic. So, I adore what you're doing, and yes, I am so into come down and be a part of it. I do wonder, like, “Hmm, is it midlife or midpoint?”

Chip Conley  30:43

Well, it's midpoint as well. So, here's my new language for it. It's not a midlife crisis, it's a midlife chrysalis because if you think about the caterpillar into butterfly journey, midlife is the chrysalis. And it's a period of time where things are dark and gooey, but it's also where the transformation occurs, the renewal occurs. On the other side of that chrysalis is the butterfly. And the u-curve of happiness -- Social Science Research is really fascinating on this. When I had my midlife crisis at age 47, I didn't have any data to look at and say, “Okay, well, yeah. I'm going through something normal. Maybe it's not a crisis, but maybe it's a low point in happiness.” And that's what the u-curve of happiness research shows, is that people between 45 and 50, I'm sorry to tell you this, Ryan, between 45 and 50 is when, on average, your mileage may vary. People hit their low point in adult satisfaction.

Ryan Berman  31:40

Oh, great.

Chip Conley  31:41

And with each decade after that, it gets better and better. So, there's a lot of reasons for that, we can unpack it if you want. But the bottom line is helping people to understand the shift that you're supposed to go through, the transformation that is meant to happen in their life. For many people, the reason actually, it's so hard is because they're holding on to a success script that they almost inherited from their family, or community, or from the culture that they grew up in. And it's around midlife where you start to realize, “You know what? I've been living this success script, and it worked for a while but it's not who I am.” And then it's like, you now need to be the screenwriter of your own success script based upon a bunch of other variables that are a function of the pattern recognition and wisdom that you have collected in your life.

Ryan Berman  32:31

This sort of nicely rolls into your definition of courage, which when we had a chance to talk a couple of weeks ago, you almost started our call with, and I was like, “Oh.” It just taught me…

Chip Conley  32:47

I don’t even remember it. What did they say?

Ryan Berman  32:50

You said, “Core and age.”

Chip Conley  32:54

Oh yeah. That piece. Yeah. So, core comes from ‘heart’ in French and in Spanish Corazon. So, there's an element of courage that comes from the idea of you putting your heart into something. And then, I also love the fact that age is the second syllable partly because that speaks to maybe something that we develop over the course of our aging, is how to actually tap into our heart to actually be more steadfast in the things we believe. And so, courage to me is this combination of heart and the wisdom from pattern recognition that helps you to say, “Yes, I'm going to fucking stick my neck out and do something that may not be on the road the most people travel.”

Ryan Berman  33:47

You think about those 1500 days you mentioned, right? From 45 to 50. It's approximately 1500 days. I wonder if there's anything too, because people suppress their heart. We suppress it. We choose to compartmentalize shit. We choose not to listen to it. And maybe your heart's like, “No, no, no.” That story you've been telling yourself, let's keep it real, I wonder if that's part of… You probably already have the stages of what's happening, right? But is it part of that where it's like you're actually telling you, “No. Where should you go? Who are you really about?” And you have to get through that 1500-day period to catapult the next two or three decades, which you said we are happier, where there's more vitality. You think that's part of it?

Chip Conley  34:39

There's so many elements to it. Carl Jung the psychologist, and Richard Rohr that famous Christian mystic who is nearby me here in Santa Fe, New Mexico. They both say that the primary operating system for the first half of your adult life is your ego, and it serves you well in certain ways. And then, at some point, it doesn't serve you so well. And it's around midlife where your primary operating system is meant to change from your ego to your soul. What does that mean? It basically means where you go a little more interior and you actually tap into meaning and purpose more. And actually, maybe a rekindling of interest in religion or spirituality tends to happen during that time. But the way I like to articulate it is that in the first half of our life, we accumulate. Just like a caterpillar is eating leaves, just bulking up. So, that's what happens in the first half of our life. We accumulate knowledge, and friends, and dating, and relationships, and then, a marriage potentially, and then children, and then responsibilities, and then bills, and then, you name it. And you get to midlife with this accumulation that is actually weighing you down. It's like the baggage of your life. And it is in midlife where you actually have to learn how to move from accumulation to editing. And it's around midlife you start to edit. And we call it the great midlife edit at the Modern Elder Academy. And it's a ritual that we do with all the people who come to our workshops. And it's really powerful because it’s like, “Wow, I feel like I've been weighed down by all this baggage.” And the exercise we do with people the first 24 hours that people are there helps them to realize what is not serving them anymore, what they need to let go off, and then what they can replace it with. And that's what happens. That is sort of like a psychological shift when you realize that you don't have to do it the way you've been doing it the rest of your life. And that there may be mindsets, and identities, and ways of thinking and being, or people in your life that you're really supposed to edit from your life. And that makes space for something else.

Ryan Berman  36:49

I guess I'm curious, why did you feel you needed to make Modern Elder Academy? I know the data is there. I get the data but you had to manifest this. Tell me more.

Chip Conley  37:04

Well, yeah. So, my personal story is that I had a bad experience in midlife and a good one. The bad one was I lost my friends to suicide between 42 and 52. But I also had my own suicide ideation around age 47. I didn't want to be running this company anymore. I'd been running it for 22 years, ultimately sold it two years later after I owned it, 24 years that I've been CEO, but I felt really stuck. And I felt stuck with my identity of what it meant to be the founder and CEO of that company, and all the great things I got from that. But it also was just confining. I had a long-term relationship, romantic relationship that was ending. I had a foster son who's African American who was going to jail, or prison wrongfully, and ultimately was let out eight months later, but that was a pain. And I was running out of cash. Long story short, is all that was going on. So, I got to the other side of it, and I had the positive side of midlife. The positive side of life was what I experienced at Airbnb. Like, “Oh, wow. Same seed, different soil.” I had all that seed of wisdom inside of me, but now, it was planted in different soil, but in soil where I could really flourish and help these young guys take their little company. And so, I believe that midlife it's a stage of life rather than a specific age. But it's a stage where you need to actually learn, like, this is this stuff's important to creating a second half of life, adult life that is worthwhile. If you're 54 years old, which is the average age that people who come to MBA, and you're going to live till 90, you have as many years of adulthood ahead of you 54 to 90, as you do behind you 54 to 18. You're halfway through your adult life at age 54. Most of us don't think that way. But it's a very personal story in terms of when I think of my friends. And one of my friends was named Chip. How weird is it to have a friend named Chip when it's my name, and he was somebody I really cared about a lot but he just had deep, deep demons. His wife and two kids found him hung himself on the family tree when they came out in the morning one day. And I just wish MEA existed so Chip had seen that he had more options available to him.

Ryan Berman  39:27

You said there's 3000 alumni, and I wonder specifically in the early days, I'm sure it's word of mouth with especially your people like your friends. But then, as you iterate and start to get the programming right, do you have the data on what percent are like, “No, you're going.” Someone else is like, “You need to go there,” versus, “I'm willing to surrender and I'm coming.” What's the percentage?

Chip Conley  39:55

(Laughs) Well, the vast majority are doing it on their own accord. People are usually… It's volitional and at their own choice. But the number one feeder for us… Number two feeder is PR, media. So, being on a podcast with you or Ritual earlier this summer, or Tim Ferriss three years ago. These media or print media, etc., is great. But the number one thing that feeds us in terms of customers and people coming, students is word of mouth from friends and family. And yeah, sometimes it’s the word of mouth, someone's seen an article in The New York Times about us and then they give it to their husband who needs it. But often, it's someone who's actually been an alum, and they go home as an evangelist, and they go and tell their friends, and their friends say, “Okay, that sounds interesting. Let me explore it a little bit.”

Ryan Berman  40:49

Man, you're the soul business.

Chip Conley  40:51

We are in the soul business. It's a really interesting way to describe it. Sometimes I say… There's a museum in San Francisco. It's famous, it’s called the Exploratorium. And it's really the exploratorium of the mind. It's like a science museum that both adults and kids love. Well, we're not the exploratorium of the mind, we’re certainly the exploratorium of the soul. And we do it with intellectual ballast so that it’s academics from Stanford, Harvard, Yale, and UC Berkeley have been our primary people who have helped shape the curriculum.

Ryan Berman  41:27

You know, about 10 minutes ago you were talking about the courage being sticking your neck out there, and going off the beaten path, when others don't. And I kind of feel like, “Yeah, you're, you're talking about yourself, and what you're doing, what you're building.” And there's this famous proverb that fear and courage are brothers. I like to say fear and courage are kin, better way to say it. And that means there's no courage without first fighting fear. And so, what's keeping you up at night right now? I'm sure you're fighting some specific fear that you're trying to shrink down.

Chip Conley  42:01

I think we're going to grow from doing about 12 - 1500 students per year to 12,000 students per year five years from now based upon the new campuses we have opening in Santa Fe, much larger campuses, based upon our MEA online programs growing in a way they've been growing. So, to basically do a 10x of our annual number of students is scary. The good news is our customer satisfaction is exceptional right now, and that's part of the reason we feel good, but our marketing engine needs to ramp up dramatically to be able to get to those kinds of numbers. And that's a little scary. What makes me confident is that the product is so damn good that we know how… We have people who've come back seven times to do a weekly workshop, and it's a different theme each time. And it's like, “Wow, that shows you something.” And so, I feel good about it but I also feel a little bit scared. And then, obviously, there's always things like recession. We're a premium product, it's not an inexpensive thing. We do have financial aid, and we're really focused on allowing people to come who can't normally afford it. And so that's good. But it's a premium product, and you go into the recession, you start… And it's also very much of a discretionary product. It's not like something a person has to do. So, overall…

Ryan Berman  43:47

I don't know, man. If you told me I should buy soul insurance, I would be in on Soul insurance. And who wouldn't want to buy soul insurance?

Chip Conley  43:58

(Laughs) I think that's the clip. We got to take that clip and put it into a marketing…

Ryan Berman  44:05

Hey, you’re the marketer who knows hospitality. I’m going to follow your lead on this one. So look, I got to think like… I’m also thinking about my dad, my dad's 80. And he's got clarity of purpose. Who am I to decide if it's the right clarity of purpose? He's a lawyer. He still works. He’s seen to many of his friends. When they retire, they're tired and they're done, and, “thanks for playing.” And so, I think he's the ‘use it or lose it’ guy. And there’s still passion to put on a suit. Gosh, he's going in to work. He's happy when he's working. And he's much softer, by the way today. So, when you talk about your dad in the military, yep.

Chip Conley  44:57

Same with my dad.

Ryan Berman  44:57

Okay. So, let's go back to that Chip who had military dad, who wasn't as soft then. And if that Chip is talking to this chip… Actually, let’s start with this Chip talking to little boy chip.

Chip Conley  45:14

Well, this Chip would quote Oscar Wilde who said, “Be yourself, everyone else is taken.” I think what I felt early in my life was that there was a path for me that my parents had sort of plotted for me, and that I just needed to be the best I could at that path. What I came to realize was that they had some great intentions for me, but my path, I needed to deviate from it a lot more. And my definition of success was going to be different than theirs. But ultimately, some of the character qualities that I actually built during that time, even though they aren't serving me to be on the same path as my parents, but the sense of achievement, orientation, and integrity, and being very relationship-focused, these are things that I think I learned on the path they wanted me to be on. Ultimately, I was on a very different path than theirs. So, I would just say to that young chip, “Dude your parents have a lot to teach you but it's your path, and your humanity that you're going to be developing here.”

Ryan Berman  46:30

I definitely felt like my parents had me on a path. And then, I also remember some Jewish kid from outside of DC. And my first real girlfriend in high school was Mormon.

Ryan Berman  46:40


Chip Conley  46:40

I was getting no action, but that wasn't important to me. I loved playing sports. And she was fun and funny. And my friends were like I'm trying to figure this out. But okay. I'm like, “That's just cool.” And I remember one conversation with my dad. And I kind of pressed, like, if I ended up part of the LDS church. He's like, “It's your life. Do what you want. It's your life.” It wasn't a throwaway, he meant it. And it confused me because I'm like, “Wait a minute, is this a trick? Is this a trap?” I thought it, it wasn't a trap. And I'm blessed -- my mom might think a little differently, by the way -- but I felt like they had given me enough to keep me going. And then, it's like, “Okay, what am I going to do on this ‘choose your own adventure’ called life?” And I do wonder if that's part of this white privilege conversation too because I've lived a privileged life to have options. All right, if little boy Chip is sitting here, or boy Chip, whatever you get to decide, and you're like, All right, buddy, what do I need to remember? Tell me something I need to hear, you need to hear,” what would it be?

Chip Conley  47:49

I think it would be good out and have fun. Just play. The good news is that I know how to play hard, and play well, and enjoy myself, but I often get so wrapped up in my calling. And I do have fun in the calling. As a CEO of this company, and any business I've been in, people have fun with me, that's for sure. You don’t start a company called Joie de Vivre, which means joy of life, if you don't like to have fun. But the bottom line is that I don't give myself enough time to just completely take the break to go do that. I meditate every day. I got the good tools and practices. This summer I took some nice vacation time and was offline, completely offline. Not checking email at all for a week at a time. A couple of two or three times, and man, did I get renewed by that. And a kid, you do too. So, often, you find joy when you break out of the habitual world you're in, and you look for awe. And kids are really good at exploring awe and wonder.

Ryan Berman  48:59

Are there videos into your program?

Chip Conley  49:05

Which videos?

Ryan Berman  49:05

Like, kids.  Like the awe, and the wonder, and the joy.

Chip Conley  49:10

We bring the videos in the program but not necessarily kids. We do have intergenerational workshops sometimes and that's fun to have kids. And we've just launched something called Generations Over Dinner, which is a totally cool thing, where you get five or six generations -- it doesn't have to be family members, but it could be -- around a dinner table. And there's a series of questions that allows people to really look at how can we learn from each other across generations? And then, sometimes it's the youngest person at the table who says one of the most curious and wise things that actually just everybody looks to and say, “Wow, that makes so much sense.”

Ryan Berman  49:45

Chip, where can people go learn a little bit more about MEA?

Chip Conley  49:49 or is my personal site. And then, on social media, you'll find this there. But the place I do most of my posting, I have a daily blog called ‘Wisdom well’ that is fun, and I love it, and allows me to write a lot. And it's all about some of the themes of MEA. You can just do a, “Chip Conley, wisdom well,” Google search, you'll find it. And you subscribe for free and you get a daily email from me. So, you can find those on LinkedIn. My LinkedIn profile is pretty full of my perspectives and wisdom. All posts.

Ryan Berman  50:28

Yeah. You and Godin are just… Like, it's not close to others. It's funny that you went to school together. I'm curious, this is a selfish question because I have a weekly dose of courage I'm trying to like, “Just let me invade your inbox once a week, try to nudge you towards courageousness, and then, get out of the way.” But do you post what you put on your email on LinkedIn too? LIke today, it wasn’t longevity, it was short-gevity.

Chip Conley  50:58

Short-gevity. Yeah. So I write the post, and then it goes out by email to the tens of thousands of subscribers we have. And then, we take the link of that post and we put it on social media. LinkedIn is the best place to find it, probably. But you can find it on Facebook, on the  MEA Facebook private group, as well as the MEA Facebook page. I actually don't post it very much to my personal Facebook page. And we also post it on Twitter.

Ryan Berman  51:30

All right. So, take us home here. When you think about just the experiment of life that you've been in, and you think about maybe three ways where you've been courageous, where it's enhanced your life, can you share for the listener who's on their own journey those insights?

Chip Conley  51:52

So, I think the first time I had to show that kind of courage we're talking about is when I was… I had a longtime girlfriend in college, we were going to get married, and it just didn't feel right. And ultimately, I came out as a gay man. And I had to tell my dad, the Marine Captain, that I'm on a different path then. And so, that was a time I had to be courageous. I had to be courageous two and a half years out of business school when I decided to create a boutique hotel company and paid myself nothing. Call it Joie de Vivre, which is a weird name. And ultimately, everybody was telling me, “You don't know what the hell you're doing.” But I had the courage to say I think I can take my commercial real estate knowledge of just a few years time, at that point, and apply it to this new phenomenon in hotels, boutique hotels. And I'd say yeah, definitely courageous right now. Creating a product in MEA that's the first midlife wisdom school, and then, these regenerative communities we've created which are like an alternative to a retirement community. So yeah. Courage or stupid, I don't know what.

Ryan Berman  53:04

I think it’s courage.

Chip Conley  53:04

Time will tell.

Ryan Berman  53:07

Well, look, I can't wait to get down to one of the locations. I think I'm leaning international between you and me.

Chip Conley  53:15

Baja’s amazing especially in the winter, dude. Nice place to come in winter.

Ryan Berman  53:20

I will gladly come sell some soul insurance with you. You just tell me where to go. And yeah. Chip, thank you so much for sharing your story and for giving us an hour. And I know we'll stay in touch. Thanks, man.

Chip Conley  53:32

Thank you, Ryan.

(Outro music 53:32-53:50)

[End Of Audio]

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