Chip Conley, Modern Elder Academy

Stacy Shoemaker Rauen: I’m here with Chip Conley. Chip, thanks so much for joining us today. How are you?

Chip Conley: Stacy, it’s great to be with you. I wish I could be with you in person but no. These are not those times.

SSR: These are not these times. So, first of all, how are you dealing with this new normal and where are you hiding out amid this pandemic that we’re going through?

CC: I think it’s the new abnormal. That’s what I think. I’m in Southern Baja, California, which is part of Mexico. I’m down here because I live here most of the year at our Modern Elder Academy campus. I will say the one good thing about being shelter-in-place in paradise is you’re sheltering in paradise and it’s a pretty remote place on the beach with farmland, and so we have lots of great food and not a whole lot of people. That’s not a bad thing so I feel lucky about that.

SSR: No. I am very jealous being over here in the New York area and trying to hide for most people.

CC: Yeah. Stacy, stay safe. Stay safe.

SSR: Yeah. Thank you. What keeps you positive during this time? Is it where you are? Is that helping?

CC: I mean we all need to know what is it that actually helps to create some level of moderation in our world because sometimes it’s a crazy emotionally contagious world. So, the contagion is not just a virus, it’s our emotions. So, for me, writing and meditating are two of the things that I like to do, and exercising. So, the writing, I tend to do early in the morning. I have a blog called Wisdom Well. It’s a daily blog that goes out to people, and it’s on the Modern Elder Academy website, and so writings part of it.

Meditating just helps me to get out of my own head. Weirdly enough to be mindful is to sort of be mindless and to just sort of take the brain and down a notch in terms of how active it is. Then, the exercise whether it’s running on the beach or swimming in my lap pool, that does it as well. But I will say that I am stressed at times. Well, I sold Joie de Vivre 10 years ago, the management company and the brand. I still own a bunch of hotels as an investor, and so there are 12 different hospitality businesses that I’m involved in and 8 of the 12 are closed right now. So, that means there’s a lot of stuff we’re having to deal with, whether it’s the mortgages or most importantly the employees.

SSR: Yeah. I mean how are you communicating with your teams right now or what have you told them to try to stay positive? I know furloughing and laying off employees is not easy. I do not envy you. So, what have you been communicating to them? How have you been communicating to them? I feel like in times like these almost over communication can sometimes be helpful.

CC: I agree. There’s an emotional equation I wrote about in one of my books called anxiety equals uncertainty times powerlessness. So, if you know that the two primary ingredients of anxiety relate to what you don’t know and what you can’t control, you try to provide people more certainty because uncertainty is one of the ingredients here. So, over communicating about things and being open and honest about the things that are really daunting is, I think, not a bad thing because people have a tendency to take their ideas about something and make it worse, especially in these times. So, that’s one piece is lots of communication and transparency.

Then, there’s the element of powerlessness. How do you help people feel powerful and having some influence in a time where you feel so out of control? That really gets down to what are some minor goals we can have in the short-term that we can try to attain? Then, having almost a weekly report of here’s the things we’ve accomplished this week. It really helps people to feel a sense, not just of purpose, but a sense that they’re actually having an impact.

I think there’s a term in psychology, which is learned helplessness, and learned helplessness is often the first step toward someone going into their own emotional depression, and so helping people to feel a sense of learned helpfulness and even if everything’s shut down in your business, it’s like, how do I help my community? How can I give back? How can I write a personal handwritten note to my long-lost sister who I haven’t really talked to in three years because we had a bad falling out at a holiday party? This is not my personal story but that’s just the kind of thing that a person could do during this time.

SSR: I think that is also very true and so very relevant in dealing with these teams now that are having to either wait on being employed or are working remotely and are very isolated, all in very different situations which is what has been the most interesting thing when leading a team is making sure everyone is okay in their unique situation because not everyone has the same setup at home.

CC: Right. Exactly.

SSR: We’re going to get into your very illustrious hospitality career, but do you have any thoughts on how this pandemic is going to forever change the hospitality industry?

CC: Well, let’s start by saying that an experience like this does test, will severely test hospitality businesses that didn’t really have their act together. I don’t mean that in terms of being prepared for a pandemic but I mean really the customer or employee value proposition wasn’t really well-executed or well-articulated. So, if you have a business that was struggling before, it’s going to actually come out of this struggling more. I like to think of hotels, now, hotels are only one kind of hospitality but this is very true for hotels. Think of a hotel and a hotel market like in San Francisco, which is where a lot of my hotels were and still are, some of ones I own. Think about a ladder and there’s a big bucket at the top of the ladder and when water is coming in like the economy is strong, the water comes into that bucket at the top rung of the ladder.

Then, it actually overflows to the next rung where there’s another bucket, and then it overflows to a third bucket. So, think of this as the primary hotels are on the top tier of the ladder. Secondary hotels are next, and then tertiary hotels are third. What does that mean? Primary, secondary, tertiary. It sort of means that within your competitive set or within your market of when you primarily compete with, if you’re a primary hotel when the spigot turns off or gets turned down a lot.

Right now it’s turned off. Let’s just sort of say that. But things will start to improve, but it’s going to improve for the hotels and the businesses that had already built up a strong emotional bank account with their employees and their customers, who actually come back and people come back as customers, even the word customer means accustomed. You are accustomed to spending money and time with those business that you really respect, admire, and appreciate the way they treat you. So, that’s really simple stuff but the point here is to say I think severe downturns and recessions have a tendency to help you see whether you’re a primary a secondary or tertiary hotel, and if you’re a tertiary hotel, you’re going to get smacked around pretty big-time and your recovery is going to take a lot longer. Now, that’s sort of just generally but I would say for the industry overall there are certain kinds of properties and businesses that are going to recover more quickly.

They’re going to be a lot when it comes to the restaurant part of the hospitality business, oh god. I mean I feel more sorry for the restaurant business right now than I do the hotel business and that is because in many cases they don’t know in their real estate, they have leases, so there’s only, they amortize that the cost of being in business over a shorter period of time, whereas if you own the real estate, the real estate may take five years to have a comeback so the values are the same as they were in 2019, it may take till 2025 to do that but at least you own the real estate so you can play the long game, restaurants can’t. Restaurants come and go more quickly and the margins in restaurants are tougher and frankly the quality control is so much about the people and you furlough people and they sort of scatter or you make people redundant by actually having to lay them off completely.

Well, it’s hard to bring the team back together. So, I would just say that the restaurant business is going to be decimated. Especially social distancing in restaurants means like, ‘Okay. I could have half as many patrons in my dining room.’ Well, that model doesn’t work. So, anybody who’s saying that that’s how restaurants can reopen, don’t understand the economics of restaurants.

Hotels will recover a little bit better than restaurants because they’ve got deeper pockets usually and they own their real estate often but the bigger question is which kind of hotels are going to recover quickly. The ones that are going to take the longest are convention hotels. Let’s just be blunt. When Mark Zuckerberg last week says, ‘We’re not going to do any Facebook events with more than 50 people until June of 2021.’ He’s pretty much setting a standard out there for the convention industry, which is like, ‘Wow. We go dormant for maybe a year and a half.’ That’s going to be a very difficult business. When it comes to smaller hotels I think they’ll make some recovery and the question is whether it’s leisure travel or business travel that’ll lead to recovery. I think it’ll be leisure travel. I think it’ll be leisure travel because people will do staycations, they’ll do family reunions, they’ll have mom’s 70th birthday party that they’re still going to have anyways at the hotel that they’ve spent their life going to every summer.

So, I do think that’s going to recover but let’s also recognize that when sometimes people say, “What’s going to recover?” We’re not factoring in, if we’re in a depression, which I think we will be. I think it’s more than a recession. If we’re in a depression, people don’t spend money on hospitality/travel products as nearly as much as they do for food and even clothing. So, I do think for that reason it’s going to take a while for the industry to recover.

SSR: Obviously, it all had to come to a halt but I’ve talked to some people at AHLA and AAHOA and going to these larger corporations and saying, ‘Will you bring business travel back?’ I agree with you. I think leisure will come first and business will come second but we need to help stimulate that business travel because that is what a lot of the mid-tier, middle-of-nowhere hotels rely on.

CC: On one hand, all of that destruction sounds trouble. The other side of it for at least on a personal level is it is helping me to see what sort of truly essential and important in my own life and whether it’s the connection with family and friends or it’s my writing, the pause helps us to witness ourselves a little bit and sort of look at do I want to operate the way I was operating pre-shutdown?

That’s a privileged question to ask for some people. For some people it’s like, ‘Of course, I want to operate because I want to put food on the table because I’m not going to be able to keep my family fed if I don’t go back to that existence.’ I get that. I’m not trying to sound sort of Pollyanna here. But I think actually looking at how this pause helps us to realize, my god, you could die tomorrow and is this the way you want to live the rest of your life if you’re going to die that soon? When I say that that dying, I’m not talking about the pandemic.

I’m just talking about things that are out of our control that we just don’t know. That is what led me to selling Joie de Vivre 10 years ago is I had a flatline experience at age 47 due to an allergic reaction to an antibiotic I was on and I went flatline. I saw the other side. They had to resuscitate me and I was in the emergency room and I see you for a day and that at age 47 woke me up to saying, ‘Is this what I want to do the rest of my life?’ I thought it was. I’ve been doing it for 22 years as CEO of that company at that point, and I thought I was going to do it the rest of my life. I was like, ‘Nope.’ I realized I don’t want to do this the rest of my life and it was very hard to shift out of the thing that was frankly, almost the only thing that I knew. I started Joie de Vivre when I was 26, 25 actually really, and so I was able to do that because I saw what it felt like to know that the rest of my life, I don’t want the rest of my life to be just like it’s been. It’s been a great life up to that point but I was ready to say, ‘I want to try something new.’ Opening that door really opened me up to the fact that the Airbnb founders approached me and the rest is history for that, seven years of working with them now.

SSR: This is all so amazing. So, let’s go back first for those that don’t know, let’s go back to Joie de Vivre. So, growing up, first, where did you grow up? Second question on that is was design or hospitality part of your childhood or anything that you knew from a young age or something that you kind of fell into?

CC: So, I grew up in Southern California. I was born almost in the shadow of Disneyland. So, theme parks and Walt Disney had a huge impact on me in terms of some day when I was young I would draw on a piece of paper what my ideal theme park would be. So, while boutique hotels are not a theme park, there’s some element to sort of the Fantasyland in the sense of what you’re trying to create in terms of a habitat that feels like it’s a perfect habitat for your guests.

I grew up with a middle class family and didn’t have a lot of history staying in nice hotels. I did know that every time we would go with our wood-clad Ford station wagon on the road to motels with our AAA guide, I would rate the motels along the way. So, I would write a little review on the experience of each place that we’d stayed in. How weird? What 14 year old or 13 year old is doing that? I think it was even before that. It was like maybe when I was 10 when I was doing that. What was interesting to me about, around travel was the idea, I was cultural curious. I had a cultural curiosity for people who are different than me. I went to high school in the inner city in LA, Snoop Dog’s high school so I was called the curious white boy because I was a white guy in a predominantly non-white school, and that was really interesting to me because it actually made me intrigued by cultures that are different than me.

Then, I went to Stanford and Stanford Business School and while I was there, I focused on real estate, commercial real estate and that’s what I did out of business school but what happened to me was I realized I don’t want to be a just a commercial real estate developer, I want to do something that’s a little more creative. I want to do something that feels like it’s serving someone a little bit more. So, that’s when at age 25 I just sort of woke up and saw, ‘Well, here’s what Ian Schrager and Bill Kimpton are doing.’ They had just started their companies as boutique hoteliers and the US movement of boutique hotels was just getting off the ground and that’s when I decided to create my company, Joie de Vivre. I called it Joie de Vivre because it means joy of life in French and I like the idea that our mission statement was also the name of the company.

SSR: Love that. What I remember when I first started at HD 20 years ago, what I loved about your hotels too is that they were based on the concept around who would read this magazine, and as a journalist, I was like, ‘This is ingenious.’

CC: The premise was this the first, we created 52 boutique hotels. That’s a lot. Fifty-two boutique hotels over my 24 years there and each one had its own name and a brand and identity and maybe even sort of a niche audience that was going after. The reason I figured out the magazine thing was the first hotel is this funky motel in the Tenderloin called the Phoenix and its market it was going after was musicians and artists and creative types who were on a budget and wanted a fun place to stay, sort of like cheap-chic.

So, as we were trying to concept the hotel, everybody had a different idea, and so I said for the next meeting, weekly, let’s try to unify around something. Come to the meeting with a magazine that you think defines the hotel. It was just going to be a way to help people align around something, and interestingly enough, of the seven people who came to the meeting, five of the seven came with Rolling Stone magazine. So, what we decided to say, ‘Okay. What are the five adjectives that define Rolling Stone magazine?’ We said, ‘Funky, irreverent, adventurous, cool, and young at heart.’ Those five adjectives became the touchstone for the personality, the design, the services that we were going to create, even the staff we tried to hire, we hired staff that were funky and irreverent. That was my taste of understanding what ultimately identity refreshment is and it’s like you are where you sleep because those five adjectives define the psychographic of our ideal customers for that hotel.

What we saw over time is that people would choose the Joie de Vivre Hotel to stay in, not just because of location or even exactly just interior design, it was more like how did it make the interior of you feel? What were the adjectives that this place felt like and how did those rub off on you such that you got what we called an identity refreshment? That’s part of the reason our hotels were so diverse. I mean one other thing I was proud of is we didn’t have, other than that approach, we didn’t have a specific design. Ian Schrager had a design. Philippe Starck’s design really sort of defined a lot of what he did, and Bill Kimpton loved Cheryl Rowley and sort of the whimsical Monaco looked or the Palomar look and there’s a whimsy to a lot of the hotels that Kimpton had back then.

But when you looked at our hotels, each one had its own soul and identity. It wasn’t the best from a branding perspective because of the fact it was hard to characterize what Joie de Vivre Hotel was other than it had a huge amount of personality and it was a reflective of the neighborhood and customer it was seeking out. But since all of our hotels were in California, it’s almost like the brand was California, and so we had a personality and a hotel for every kind of California experience.

SSR: I think you were ahead of your time, right? It’s what everyone tries to do now over the last 10 years or so. I mean having an idea like that and I know you’re in real estate but how did you go from wanting to do it to actually pulling it off? I mean I guess it was maybe easier back then to open a hotel than now. I don’t know if that’s true or not but how did you get from I have this idea to opening the door?

CC: It was interesting because I was not from a family of money. So, I couldn’t say, ‘Hey, mom and dad, give me some money.’ I said like, ‘I got to do something really cheap, really very frugal.’ I went looking for a hotel in a bad neighborhood in San Francisco and the Tenderloin is right next to Union Square in San Francisco so there were hotels and motels there and I found a motel that was in bankruptcy and was on a 40-year land lease. So, they didn’t own the land. So, therefore I could buy it. I literally bought the motel with 44 rooms for $800,000. You can’t even get a condo in San Francisco for $800,000 today. So, I bought it for $800,000, renovated it for $200,000 total, and then had $100,000 left for working capital. So, I raised $1.1 million from people I went to college with, graduate school with, people who I grew up with, and they were betting on me. I mean they were certainly not betting on the location of where I chose or my history and prowess as a boutique hotelier.

So, I had to have them really believe in me and luckily the first one became a hit and a success, and so that allowed us to keep going. But the first one took three and a half years before I went to the second one and the third one. It was not an overnight success and it wasn’t until year seven that we really did our first sort of upscale boutique hotel because the first three were all sort of dodgy locations, not high-priced. They were lucky if they were a 3-Star hotel.

Then, we then we got into some higher-end stuff and that’s when Kimpton start noticing us and that’s when some others started noticing us as well because they said, ‘Oh, okay. Well, he doesn’t just do funky motels, the Joie de Vivre Group, they’re doing some high-end stuff.’ Ultimately, we competed with Kimpton to try to build a hotel on San Francisco’s Embarcadero, on the waterfront, which ultimately became our Hotel Vitale and we won the competition to build on the city land and that was a big deal because, at that point, we had been around a little bit longer but I think, at that point. When we started competing with them, oh, I think we had been around, gosh, about 12 years as a company. Then, to beat Kimpton in our own backyard to do a four and a half star hotel on the waterfront was not like my origins of buying a motel. There was a pay by the hour motel in the Tenderloin.

SSR: Do you say that was probably one of your proudest projects or the project that was most memorable to you because of that or is there another one? I know it’s hard to pick your favorite projects over 50.

CC: The Vitale was a gamechanger in the sense that it showed that we really could do a large, it was 200-room, large enough boutique hotel that was really upscale and have it be very successful. When we took over the Ventana Inn in Big Sur charging $600, $800 a night per room was a gamechanger for us as well because it said we could be in the luxury market.

The other ones that actually sort of make me proud. I’m really proud of Costanoa, which is way ahead of its time. So, Costanoa was a boutique campground on Highway 1 on the Pacific Coast Highway of California in between Santa Cruz and Half Moon Bay. So, it was about an hour south of San Francisco. We started seven years before the word glamping had even been coined. So, the idea of glamping was not even in the lexicon yet and it didn’t succeed.

I liked to say that was a noble experiment and the dotcom bust had a lot to do with it. It opened and was successful weekdays and weekends and then when the dotcom bust came along, all of our weekday traffic which was dotcom companies doing retreats just went away, and we couldn’t survive on just weekend business of families and people coming and doing sort of a weekend getaway of comfy camping in tents, sort of like glamping tents but real small ones.

But ultimately, that place taught me a lot about the fact that everybody wanted to do yoga and this was, again, 20 years ago before people knew, 22 years ago, before people really knew that yoga was a big thing or was going to be a big thing, and so when we opened the Vitale a few years later, we put a yoga studio up on the penthouse level and had offered free yoga classes every morning and people were like, ‘What are you talking about? This is not a spa hotel. It’s a financial district business hotel.’ You know what? Business people are doing yoga, and as it turns out it was something that people really liked.So, sometimes you’ll take a project that was an experiment and maybe a failure and take some of the lessons and apply it somewhere else.

 SSR: That’s so smart. Were there any kind of crazy, first-time hotelier type stories of those first 10, 12 years that stay with you?

CC: Well, I’ll tell you. I think sometimes the best ideas are just crazy but they’re really simple, and so let me go back to the Phoenix. So, the Phoenix was going after the rock ‘n’ roll hotels, go after musicians and bands, and so we thought, ‘What’s the best way to have them even know that we exist?’ So, we went to the main concert venues in San Francisco and promoted ourselves to them. Then, we went to entertainment travel agents and promoted ourselves to them, and then we went to management companies that managed bands, and we went to them. All of that was okay but we didn’t see an avalanche of business, and then we came to ask the question: ‘Who is it that really decides where a band is going to stay when they’re on the road, especially if they’re driving on a tour in a big, one of those big buses, one of those band tour buses?’

As it turns out at, the decision maker was none of the people that we originally targeted. It was actually the tour manager, almost always a guy who is usually about five years older the band and his job is to make sure that they didn’t actually overdose or have a groupie cart them off from the tour. So, those guys were typically very stressed by the time they got to San Francisco because the tours usually started on the East Coast and moved west. So, what was interesting is we had a room in the hotel or the motel that was a massage treatment room and we started offering those tour managers a free massage when they arrived at the Phoenix as long as they gave us 10 roomnights, which it could be 5 rooms times 2 nights or any size, most sized bands giving us that many roomnights.

So, all of a sudden, the tour managers loved us and they started talking with each other and that example is just a great little example. All it cost us for that marketing was to just give a free massage. We had massage staff there and give a free massage to the tour manager and that led to the Phoenix having everybody from David Bowie to Linda Ronstadt to you name it and their bands come through and stay in a funky motel in a bad neighborhood when many of them could have stayed at the Four Seasons or any other one of the hotels that were more upscale in town.

SSR: So smart and so simple as you said and knowing your client, right? Knowing who’s coming there. So, when you started, was this a long-term plan or just hope it works type of plan? I know hindsight is always 20/20 but did you have an overall business idea of what you wanted to do or were you just hoping to get one done and see how it went?

CC: I had written a business plan of how we would open 10 hotels in the first 10 years. So, I got on Stanford Business School so always feel like a Type A MBA, but to be honest with you, about six months into it, I threw that business plan away. I said, ‘There’s no way I can open 10 hotels in 10 years because I’ve just got my hands full with this first one.’ I just said, ‘You know what? I want to make sure this first one is successful, and then I wanted to figure out if I want to do a second one.’

So, took three and a half years to get to the second. Second and third would happen almost overnight together, but then it took another three and a half years to get to the fourth one. So, year seven, we had four, but here’s the part that’s interesting. We went from four hotels to 13 hotels over the next three years. So, by my 10th year of being in business, we had 13 hotels. But it didn’t happen sort of one a year, which was the way I initially thought it would. I was curious about the idea that the hospitality business had become all about predictability. Back in the 1980s, the hotel chains predominated Marriott, Hilton, Holiday Inn, etc., what they really were defining was predictability. So they’re really focused on the hard goods, the standards were all about physical standards. There was very little in the way of sort of experience standards or service standards.

There was a service manual for sure, but it was very robotic. The Holiday Inn in Denver was supposed to look like the one in Dallas, as if you go from one city to another and you want to wake up in the morning and forget about what city you’re in. No, you actually want, even if you’re on business travel, you want to feel of a sense that you’re living like a local a little bit. That’s why ultimately when I went from boutique hotels to Airbnb, I just imported my live like a local point of view over to Airbnb because that’s what they were in the business of doing is helping people feel like they’re living like a local.

SSR: So, that’s a perfect transition. So, you are at 50-plus and you had this life experience that you mentioned before, and so what did you learn from that experience that made you want to sell your company and then ultimately end up at Airbnb?

CC: You can either have a job, a career or a calling in your work. I think of it in the form of a pyramid or a triangle, and generally speaking most people have a job, some people have a career, and a small number people have a calling. My job was a calling for a long time, and then it became a job, and when it was became a job is like the anesthetic wore off and I no longer enjoyed it.

So, what I needed to do is sort of figure out what was I going to do next if I were to leave this? So, I wasn’t sure. I figured, ‘Okay. I’ll make some space in my life and I’ll see what emerges.’ I didn’t really know much about Airbnb to be honest with you. I didn’t know much about home sharing. So, I’ve been a pioneer in boutique hotels but now at age 52, I was the establishment. I didn’t understand this home sharing thing or Airbnb, and so when I got a call from Brian Chesky saying, ‘I’d like you to be my mentor, and I’d like to have you give a speech at Airbnb about hospitality innovation.’ I said, ‘Sure” and did it, and I was really curious by the how young people were. I mean the average age in the company was 26, I was 52, do the math.

I was intrigued, but I didn’t realize that Brian was inviting me there to audition in essence, and he wanted me to be more than just his mentor. He wanted me to basically help the three founders with the process of running the company. I wasn’t going to be doing that alone. There was a small team of senior leaders that I was going to do that with. But there was nobody who had an entrepreneurship background, a travel, or hospitality background, nobody who had created a non-tech company, and so that led me to having a pivotal role in the years 2013 to 2017 when the company was really in its heyday of the early stages of growth.

Then, in 2017, I stepped away from a day-to-day role to just for the last almost three and a half years be in a strategic advisor role. But it was a hard thing, because let’s just be honest, I was Darth Vader.  Initially, I wasn’t Darth Vader. I was more like, ‘Chip, you’re just so weird.’ Like the hoteliers that I knew were all like, ‘Why would anybody want to go work with that company? That company’s going to be a big failure.’ So, people laughed at me.

SSR: Well also Ian Schrager said that Airbnb would be the death to the hospitality industry. So, it was almost like at the same one of the biggest competitors to what you just built your career on at that time.

CC: There’s a famous Gandhi quote about India’s relationship with Britain before India went independent. Gandhi said, ‘First they ignore you, then they ridicule you, then they fight you, then you win.’ So, ignoring was the first piece. Literally, it was five months after I joined Airbnb that there was the first article writing about the fact I joined the company partly because we tried to keep it under wraps, partly because nobody really knew who Airbnb was.

So, it started with ignore, ridicule, fight.Then, the ridicule, it came initially, like, ‘Who would ever want to stay in someone’s home? Where are the service standards?’ Part of my job was to try to help take Airbnb mainstream. Airbnb started as budget travel generally for Millennials in urban centers and what I said is, like, ‘We got to go beyond that. We got to be outside the urban centers. We got to be global.’ Because, frankly, at that point, a HomeAway and VRBO was doing this in the second home market for years, and so let’s go into their market. Let’s go beyond budget travel. Let’s go out and try to mainstream this. That’s when the ridicule moved to fighting in about 2015. So, I’ve been there a couple years at that point, 2014, 2015 is when the fighting really started. Yeah. Ian’s words were part of that, others were.

What was interesting is that people like Arne Sorenson at Marriott and Chris Nassetta at Hilton, and the team at Hyatt, I was having great conversations with them. They were particularly intrigued by what we were doing. Publicly they were generally speaking the global hotel giants were at least respectful, not necessarily the hotel associations or lobbyists, but Arne said a lot of positive things about us, and I think partly because they were starting to get to a place where it was if we can’t beat them let’s join them. Let’s figure out how we could be in this business as well.

I did become Darth Vader for a while there because I would go and speak at hotel conferences and people were like, ‘What the hell are you doing?’ Generally speaking, at the end of the day, people were pretty respectful, partly because in some ways I was a voice in the company who’s saying to the young founders who were 21 and 23 years younger than me. If you’re going to be a hospitality company, you got to have some rules and restrictions. You have to work and create regulations in the markets around. You got to pay hotel taxes. You got to do a bunch of stuff because otherwise we’re just this, we’re a disruptor that doesn’t respect the industry we’ve disrupted.

I do think that that allowed us as a sharing economy company to ultimately have a better brand than say Uber did. Because people said, ‘Yeah. I hate Airbnb but I do feel like they’re trying to both expand the travel universe because 40 percent of the people who are traveling on Airbnb would not have made the trip or not paid for the trip. They stayed with friends or family or not made the trip.’ So, we were expanding the travel universe a little bit and we were trying to be good citizens in terms of how we operated. It didn’t mean that there weren’t still people who hated Airbnb because Airbnb became almost cancerous in some people’s mind because of the fact that whether it was affordable housing and people shifting monthly rentals into nightly rentals and neighborhoods not liking that as well or it was just having so much new supply on the market.

This is also another reason why the regulations were necessary because regulations helped to not just legitimize Airbnb, but it helped to make sure that each municipality can determine what makes sense, what makes sense in an affordable housing market or a market that has no affordable housing like San Francisco is going to be different than maybe a market that is a combination vacation rental market like San Diego. Because San Diego a lot of retired people live off the people who are going to live in their cottage in the back and pay a nightly rate.

SSR: I think that’s a really good point. I think a lot of people were angry at first because you guys were, or Airbnb was almost getting away with things that they weren’t allowed to do in the hospitality industry. So, when you level that playing field I think that’s when people started taking you guys more seriously and want to join you versus fight you, which congrats for being that voice of reason.

Switching over from straight hospitality to this hybrid Airbnb model, what were some of the greatest lessons learned there? What did you take away from that experience? I know you’re still consulting with them but you’re not there fulltime like you were. What were some of your greatest takeaways?

CC: I think one of the nice things, again, from the design perspective was two of the three founders came from design school from the Rhode Island School of Design. They were not hotel designers. They’re not hospitality designers. They were frankly more web designers, and they were into design thinking. So, it was a kind of design that I was not as familiar with. I was much more familiar with hospitality and hotel design. But I think the idea of how do you design an experience became really interesting and what’s the customer journey that we’re actually trying to work on here with someone who, the skill, the service is going to be delivered by someone who’s not even our employee?

So, it was a fascinating process for me to say, ‘What’s the process of helping our host community globally?’ I was in charge of all the hosts globally to actually deliver remarkable experiences and how do we train people who are not your employees? That was really fascinating and it had a lot to do with looking at internal motivations. How do you motivate people? So, that was a big lesson. It’s like how do you take psychology and apply it here because there are no rules that I had about how we could get Airbnb. Airbnb has a guest satisfaction rating based upon the primary benchmark that hospitality uses, which is called NPS, Net Promoter Score. Everybody’s NPS score is substantially higher than the hotel industry, which if you told me that when I joined seven years ago I was like, ‘No way. No way.’

When you see the articles about things that go wrong in an Airbnb, absolutely. They do go wrong sometimes, but the thing that’s interesting about Airbnb is it took the idea. So, think about Airbnb is to boutique hotels what boutique hotels were to chain hotels. So, what boutique hotels taught the chain hotels is experience is important and you want to try to select the right boutique hotel that fits your personality, otherwise, you may be in the wrong habitat, and there are a growing number of people who are experience-driven and are willing to accept more variability or standard deviation in terms of their experience.

I used to say at Joie de Vivre, ‘you may have your best or your worst experience of your life in a Joie de Vivre hotel. We’re going to make sure that the most of you feel it’s your best.’ But for some people if you check into the rock ‘n’ roll hotel and you’re not a rock and roller, you may not like that hotel. So, take that idea to Airbnb which is like, ‘Wow. It’s exactly the same.’ Some Airbnbs, the standard deviation is higher but the reason that the guest satisfaction is so high is because on average, we have a level of dependability, not consistency, but dependability that you actually got what you thought you were going to get.

Now, does that happen all the time? No. But the scores are pretty prevalent, and frankly, Airbnb’s growth speaks to it as well. The brand got to a place where people saw that the most important thing that we had to educate our hosts about and if you didn’t do this well, we dinged you big time and maybe even took you off the platform, which we did to tens of thousands of hosts, is accuracy was essential. We needed to make sure that the reviews, since we’re a peer-to-peer review system with over 70 percent of hosts and guests reviewing each other, whereas the average in the hotel industry is 5 percent. Our review system created the cleansing mechanism for us to understand quality and using that data, we could determine which of the listings we wanted to feature versus not feature or not have on the platform. So, it’s a combination of data and psychology.

SSR: That’s really interesting and there might be some lessons learned there. I know hotels are rated all the time, but there might be some lessons learned there for hotels moving forward because I think cleanliness as in wellness is going to be such a bigger factor moving forward after all this.

CC: Agreed.

SSR: So, you made your mark in hotels, you came into Airbnb and helped evolve that company to have more of a hospitality mentality, why then did you decide to pivot one more time? Some people never pivot once, you are now pivoting three times, which is remarkable or maybe this is your fourth if you count real estate. So, why a time for another pivot? Then, talk to us about Modern Elder, which you mentioned in the beginning and how that came about.

CC: Well, the idea for it came about because of Airbnb. I was called the modern elder, who is as curious as he is wise. That’s what they called me. ‘Chip’s the modern elder. He’s as curious as he is wise.’

SSR: Does that make you feel better?

CC: Yeah. I felt like it made me a modern elderly so I didn’t like it so much. But an elder and elderly are two different things. Elderly is the last 5 or 10 years of your life. Elder is a relative term and if I’m 52 surrounded by 26 year olds, I was an elder, that’s for sure. So, that led me to writing this book Wisdom at Work, The Making of a Modern Elder, while I was writing the book I was in Baja where I have a home on the beach. I went for a run one day and I said, ‘Why is there no school for people in midlife to reimagine how you want to live your life and how you want to maybe even repurpose your career? How do we actually create a world where if we’re going to live longer but power in a digital society is moving younger and the world is changing faster, how do we create an environment or maybe even a school where people can go and repurpose themselves and feel relevant again?’ Because a lot of people in their midlife feel irrelevant.

So, we decided to beta-test it for the first six months of 2018, and built the campus and open to the public, went really well. Open to the public November 2018 and we’re now in our second academic year. Although we’ve closed because of that pandemic. Hopefully, we’ll reopen in mid-October. That’s our current thinking. We’ve had 800 people from 24 countries go through it. Really high customer satisfaction. The thing that’s really interesting is it’s a transformative experience. People come for a week then they leave a week later feeling pretty transformed by the experience, which is not something that you can easily do.

One of the fastest growing trends in the travel industry today is transformational travel. Transformational travel speaks to this idea that the travel experience can actually transform you, and whether that’s doing volunteerism or learning about something or going to a place that feels deeply spiritual like Machu Picchu. Excuse me. The idea of transformational travel, using travel as a means to transform yourself is not new. What we did though is new in the sense that it’s the first midlife wisdom school in the world. I think it’s going to be a long-term trend. I’ve been on the board of the Esalen Institute for 10 years and it was the first personal growth retreat center that opened in 1962 in Big Sur, California. I saw that place within a dozen years after it opened, there were a hundred personal growth retreat centers across the U.S. in places like Omega and Kripalu and lots of famous places that on the East Coast.

So, long story short is this is a social enterprise. So, over 60 percent of the people are on some form of scholarship we give them. So, we really want the cohorts which are 18 to 20 people to feel like you get to know each other and it’s a real diverse group of people. It’s a physical therapist, an elementary school teacher, a tech CEO who retired and maybe a lawyer who just doesn’t want to do that anymore. The kind of connection we help people foster creates a support group for the rest of their life.

SSR: Is it always to have them figure out their next career or is it sometimes just letting them be okay with their current career?

CC: It’s both. Sometimes it’s not even career oriented at all. So, we say that we’re in the business of helping people navigate midlife transitions. So, the transition could be a career one or it might be a divorce or it might be empty nest, it might be your parents passing away, it could be a health diagnosis, it could be wanting to completely change where you’re going to live the rest of your life, and so people are in the midst of change. Now, the change for someone in a career level could be, I want to change just how I’m seen in the company and how I make a difference in the company. So, I want to sort of be wiser. I want to learn how to cultivate and harvest my wisdom. That’s fine. People come and they come back to the workplace feeling completely energized and hearing from people in their workplace like, ‘Wow. What did you do?’

But for a lot of people, it’s actually, I really need to change what I’m doing or I need to figure out what I’m going to do. People are going to work longer, that’s just reality, and it’s partly because of choice and necessity both. Our average age is 53. If you’re 53 years old and you feel like you’re going to work another 20 to 25 years and it’s been a long time since you went back and did any kind of lifelong learning beyond your own specific knowledge area, you want to open yourself up to new things and that’s really what we do. I really do think midlife schools that help people to reimagine how they repurpose themselves are going to become a pretty big time thing in the next 20 years.

SSR: Yeah, especially as every generation seems to work a little bit longer and live a little bit longer. It makes complete sense. With all these people having different moments in their lives, you don’t have to give away all your secrets to success but how do you formulate that week? Is that different talks? Is that different experience? What does a week kind of look like? Is it a series of lectures? Is it a series of experiences? I’m guessing it’s a mixture.

CC: It’s very experiential. There’s a 160-page workbook that we go through but it’s very much how do we curate great conversations. So, just like you create amazing experiences at conferences and meetings, Stacy, and your team does. Well, similarly, we are very focused on how do you create an experience that is memorable? The memorable stuff is not a PowerPoint presentation. So, there’s no PowerPoints and sometimes we’re actually literally in nature and learning in nature. The classroom is at the end of the beach with a pile of rocks. We actually start learning that there’s a lot of beautiful metaphor of how rock balancing is almost a way to understand what it means to mentor a human, someone younger than you. We call that mentoring stone.

It’s very much creating conversations with people and some of the key learning lessons relate to Carol Dweck’s work, a psychologist from Stanford called mindset. How you move from a fixed to a growth mindset? That’s a very fundamental part of our week. We do something called appreciative inquiry. How do you become an amazing questioner, a great listener, and then asking great questions? So, you don’t have to be the person who knows it all. You become the person who just ask the best catalytic questions.

So, some of this stuff is really deeply emotionally moving and creates vulnerability because one of the things that’s true of a lot of people in midlife is they’re stuck and it’s time for them to evolve and it’s something out of their life, and so part of the week is about the great midlife edit. What is it that you are ready to let go of? Whether it’s a mindset or a responsibility or just a way of being that isn’t serving you anymore so you can make some space for something new.

SSR: Was it hard to find the teachers and collaborators to do this with or was that fairly seamless?

CC: No. It was definitely a collection of collaborators, some professors from Berkeley, Stanford, UCLA, some really well-known leadership coaches and life coaches. So, it was a combination effort and we were fortunate because we had 13 weeks of beta tests, we were able to test a lot of stuff, and by the time we finished the beta period, we had a pretty, pretty solid curriculum.

It’s been really gratifying to have a lot of well-known leaders in the longevity, aging space, and in career transition space come to the program and say, ‘You guys knocked it out of the park. This is exactly what the world needs.’ Because in the past, you had like a one tank journey. You fueled up with all your education in high school, college, and maybe graduate school, and then you drove this vehicle, your body and your life for the rest of your life and you wonder why people were in their 50s sort of running on fumes. Well, we need a midlife pit stop because life is not just one tank journey. You need to fill-up along the way. This is probably the reason some people go to conferences, probably the reason why conferences are valuable because they actually do, they’re a little mini fill-up. Ours is a little bit more of a maxi fill-up in the sense that you come for a week and you’re full a week later. The alum program is on-going so you continue to actually learn as an alum through the programs that we offer.

SSR: That’s so cool. I’m guessing in small groups that come for a week at a time?

CC: It’s 18 to 20 people.

SSR: I feel like this is super relevant right now, especially since, unfortunately, I think a lot of people will have to make a pivot, right? Where they have to make a change after COVID, not everyone will go back to the same job that they’re going to, that they were in or we’ll take this time like you said to really think about is this what they want to do. Is there any piece of advice that you would offer them right now for those that are going through it or might be furloughed or might realize that there’s more out there than what they’ve been doing?

CC: When you have a fixed mindset, you have a tendency to focus on winning because you want to prove yourself, and the challenge with that as you get older is there’s certain things in life you actually get not as good at as you get older, and so what happens is if you’re only focusing on winning to prove yourself, you actually start to narrow your scope of what you do and your life gets a little bit boring, and maybe your career does too.

If you have a growth mindset, instead of trying to prove yourself, you’re trying to improve yourself. Instead of success being winning at something, success is defined by learning. So, if you’re learning and improving yourself, what you do is you start opening up your sandbox so that you have more options in life. That’s the key. The key is to know that when people are able to be open to being what we call liminal, to be liminal is to be in an awkward transitional space, and somehow we think in adulthood, we’re not supposed to be in a liminal space or in transition and we are. So, part of the reason that we’ve seen a huge growth in midlife suicides in the last 20 years, 50 percent growth, is because people actually feel irrelevant and feel lost as to how to not look stupid in midlife starting something new. When, in fact, all of us look stupid at some point in our week, and we welcome that. So, helping people get to a place where you try something new and realize which of the things you’re actually sort of good at but didn’t know you were good at.

SSR: it just shows that there is this great need to have these new tools because the world is shifting every day, it’s just changing and you’ve just been on every right wave, Chip, and just done some amazing things along the way. So, it’s just a pleasure to hear your perspective?

CC: Well, I’ve tried, and I’ve tried things that haven’t succeeded too. I think the Costanoa is an example of something that didn’t succeed as a boutique campground. I created a website based upon the 300 best festivals in the world called Fest300, it didn’t succeed. So, I think the key is knowing what’s your batting average, and how do you get up to the plate and try things that are hard at first. I’m learning Spanish right now and I’m learning how to surf, and I’m 59 years old. When you’re 59 years old, you usually don’t learn those things but I know that they will serve me, especially the Spanish as I get older living in Mexico much of the time.

SSR: Cince this is, the podcast is called What I’ve Learned and you’ve shared so much but would you say that’s your greatest lesson learned is to know your batting average or to just give things a different try, look at things from a new perspective? What would you say from all this, from hospitality, to Airbnb, to Modern Elder? What do you think has been your greatest lesson learned?

CC: I think my greatest lesson learned has been, I started at age 26 creating a wisdom book and it was just a little like journal of what I learned that week, and I would fill it, not every weekend, basically, between Friday and Sunday, I try to fill it with three or four bullet points from that week. I didn’t always do it. But when I was in difficult times I would do it every weekend.

I got to say that over the course of a lifetime, that’s 33 years ago, filling seven different books of wisdom and learning I had from the week has made me a wiser person all the way because I’ve been able to metabolize the lessons, sometimes the painful lessons, and sort of keep it fresh in my mind and sometimes I’ll go back to a wisdom book from the past and say, ‘God. This reminds me of the Great Recession. I want to go back and see what were some of my lessons in 2008 and 2009.’ That sounds like, ‘Oh my god. Nobody does that.’  I did it, starting at age 26 because I was so fucking clueless that I felt like I just had to actually make a list of the things I did have a clue about but I was learning along the way.

SSR: No, and you’re so smart because you’ve been through a lot, right? You started your first hotel in the late 80s when there’s a crash then, you went through the dotcom, there’s been 9/11, there’s been, now COVID. Going back and looking at those books, I mean have there been things that you think you can use from them to get you through right now?

CC: First of all, that’s part of the reason why I’m writing this blog post and doing videos about my lessons from past downturns. So, every Monday for five Mondays in a row, I did four of them. I’m doing my next one this coming Monday. I’ve said here five lessons I’ve learned around customers, around employees and culture, around navigating finances, etc. Because I wanted to go out and share some of my learning along the way. That’s really what the MEA is all about as well because it’s about sharing wisdom is not taught, it’s shared.

SSR: I feel like even now more than ever people are more open to sharing what they’ve learned to help people get through this. So, thank you for constantly sharing. You’ve been an inspiration to me my entire career and for many in this industry. So, I can’t thank you enough for taking the time today to sit down with us.

CC: Thank you, Stacy, keep doing the great things you’re doing and let’s make sure the world knows that conferences and meetings are coming back.

SSR: Yes. Let’s make them know that because Lord knows we need them.