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Jazz Shaper: Chip Conley

Posted on 30 March 2024

Chip Conley disrupted the hospitality industry twice, first as the Founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and then as Airbnb’s Head of Global Hospitality and Strategy, leading a worldwide revolution in travel. 

Elliot Moss                      

Welcome to Jazz Shapers with me, Elliot Moss, bringing the shapers of the business world together with the musicians shaping jazz, soul and blues.  My guest today is Chip Conley, founder of Joie de Vivre, the US boutique hotel operator and co-founder of Modern Elder Academy, the midlife wisdom school.  Having launched Joie de Vivre when he was just 26 with a single hotel in a tough San Fransisco neighbourhood, Chip grew his company into the second largest operator of boutique hotels in the US.  But in his late forties, he started to dislike his job and at the same time experienced financial and deep personal loss that together brought about a sense of crisis.  After a serious allergic reaction to an antibiotic from which Chip almost died, he sought to change his life.  Two years after selling Joie de Vivre, a small tech start-up called Airbnb asked Chip to help them create a democratised hospitality world as their Head of Global Hospitality and Strategy.  But it was his unofficial title as their ‘modern elder’ that gave Chip an epiphany.  Why don’t we have places where people can repurpose and reimagine themselves while also consciously curating the second half of their life?  Chip launched Modern Elder Academy, MEA, in 2018 and they now support over 4000 alumni from 47 countries to develop a renewed sense of purpose and happiness in midlife and boy, isn’t that important. 

For transparency sake, we are not in the same place, I mean we are in the universe together, Chip, we are talking together but you are not with me in the studio.  Where are you today, Mr Chip Conley?

Chip Conley

I’m in Santa Fe, New Mexico, the land of enchantment. 

Elliot Moss

The land of enchantment.  And there is a time difference which means it’s bright and breezier, even earlier for you than it is for me.  Thank you so much for joining.

Chip Conley

Thank you.

Elliot Moss

The 26 year old Chip, why did he start his business then?  What led him to that moment?

Chip Conley

You know, I was an entrepreneur as a teenager, I tried out all kinds of different businesses and as I went into college I was still fascinated by that but I also felt like a needed to get a job so I went to Business School, got my Masters in Business and did all the things you normally would do but that entrepreneurial urge was still there and then in my mid-twenties, I started to notice that boutique hotels were making a first impression in the United States and I was a real estate developer and I thought like okay, maybe I can take that real estate development background and apply it to boutique hotels and that’s really how it happened.  And I called it Joie de Vivre, partly because I wanted to have joy in my life.

Elliot Moss

And before the real estate bit, I mean I’m just interested because its, people’s journeys always fascinate me.  The real estate thing was just happenstance or was it, again, a strategic Chip post, post MBA going “this is going to make me some money.” 

Chip Conley

Ha, ha, ha.  Well, it’s interesting, my uncle was a very successful commercial real estate developer and broker and he took me under his wing, so he mentored me, so I learned from him but quite honestly, I didn’t want to have his life.  He was doing industrial buildings mostly, it was really boring and so that’s why boutique hotels was just really opposite of industrial buildings were what attracted me and yeah, the money piece of it was never important to me, never has been in fact.  Yes, it’s helped that I’ve done well over time but money for money’s sake might mean I was a litigator, oh no, did I say that?

Elliot Moss

Of course not, perish the thought.  Can I, and then just again, when I look, you know I get the chance, the privilege to look at people’s pasts and things and I looked at photos of you with these beautifully flamboyant, you know, clothes back in the ‘80s and doing your thing.  Was it, apart from the, you know, the sense that there was an opportunity there, was it, the Joie de Vivre point, was it really that you were enjoying your life and you wanted to augment it or actually, you weren’t enjoying the real estate business and you really wanted to find it?

Chip Conley

Yeah, I would say it was not enjoying the real estate business and I was very curious about boutique hotels because I like design, I like serving people, I like being creative so all those were really good for the boutique hotel business, not so good for the industrial building business and so that led me to taking that path and the reason I called it Joie de Vivre was yes, it was for my own joy but it was also, I wanted to create a culture that created joy for our employees and for our customers as well.

Elliot Moss

And you ran that for a long time and actually for those people that are familiar…

Chip Conley

24 years.

Elliot Moss

24 years and now it’s called JdV and it was part of the Hyatt Group and at one point, if I understand correctly, 52 hotels.  Is that how many?

Chip Conley

That’s right.

Elliot Moss

That’s a lot of hotels.  So you build this business up and it gets big and I read about the tension between the creativity and the fun and the freedom that you used to enjoy and then suddenly you’re in a big machine.  So you think you called it right time-wise or do you think truthfully, if you look back, you would have gone, ‘you know what, I really should have done this a bit earlier’. 

Chip Conley

Oh I should have done it earlier.  As a company, we survived the dotcom bust and 9/11 and did really well and I should have sold after that but soon after that we went into the Great Recession and I had been a gladiator for the prior downturn and I was a victim in this downturn and so it’s no good to be the CEO of a fast-growing company when you feel victimised being in that role.  So, if I could do it over again, I would have probably sold the company five years earlier and at that point, had some space in my life but instead I went into the Great Recession sort of in a dark place and then opened fifteen hotels in 21 months right as we were going into the recession so, it was terrible timing and everything else in my life was falling apart too so, I, I think I kind of made it through that time.  It's one of those moments in one’s life, you look back and say, it probably never will be as bad as that.

Elliot Moss

And you talk a lot about wisdom and wisdom that comes with age.  If you can juxtapose the lessons you learned building a 52 hotel empire with the lessons you learned in your life and then moving forward to the next chapter which was this small rinky-dink start-up called Airbnb.

Chip Conley

Yeah.

Elliot Moss

Which are the biggest lessons for you that you’ve then leant on as you moved into that next phase, which I do want to touch on because there’s, there aren’t many people that know what the inside dealings of a, of a you know, a global behemoth like an Airbnb are. 

Chip Conley

Yeah.  So, I think I learned the lesson as the CEO and founder of Joie de Vivre that I don’t have to be the hero all the time.  And that was a hard lesson to learn because I think my ego got stroked by the fact that I could go out and solve problems and make everything good and everybody loved me as a result of that and so when I sold the company, I was sort of in a place of like “okay, who wants me to be their hero?” and what happened when the founders of Airbnb reached out to me, it was obviously a tiny company at that time, I realised pretty quickly that I had to right size my ego so the lesson or the wisdom I had there was like, the way I had lived my life and my career at Joie de Vivre was not going to be what I could do at Airbnb because I was not the CEO, yes, I was a CEO whisperer, I was the in-house mentor to the founders but I also was reporting to Brian Chesky, the CO and co-founder, who was 21 years younger than me.  So, I wasn’t going to get my name and my face in the paper very often, like I used to and I wasn’t going to be running our leadership meetings but I was going to be making sure that Brian got his name in the paper in good ways and they ran good meetings, so it really pushed me from being the egocentric CEO to the, I don’t know, sole centric mentor, coach and almost like father figures to Brian and that was a huge lesson and a big relief as well because it was fun to take off my hero’s cape. 

Elliot Moss

And alongside taking off your hero’s cape, and I get the, the ego putting it at the door as people say and then that sense of serving rather than being, as you said, the solver of everything.  In terms of the life lesson stuff and you know I alluded to it at the beginning and I don’t quite know how the timings scanned with this but losing friends, getting that sense of mortality, which happens when you lose a loved one, I lost my father not that long ago and there is an immediate sense of your own mortality in a really strange way that you, is utterly experiential in the same way having children is utterly experiential, it’s just one of those things you can’t quite describe.  What did you take from that, Chip, as much as the ‘I’m now the whisperer and I’m happy not to be the hero’, what else was going on for you?

Chip Conley

Well, you know I lost five male friends to suicide at ages 42 to 52 during the Great Recession and I had my NDE where I died nine times in 90 minutes due to an allergic reaction to an antibiotic so, I think what really was top of my, for me in my late forties and early fifties was, every moment matters and I wanted to seize the day.  But instead of seizing the day as the entrepreneur who is just going to go out and work myself to death, instead it was more like seize the day in my relationships and in my hobbies and in writing because I loved writing books.  I really created a more multidimensional life because I figured I didn’t know when I’m going to die and I don’t want to be that person who, on his death bed, regrets not going to Iceland or, you know, not, you know, going around the world to experience the world’s best festivals.  So those were the kinds of things I did. 

Elliot Moss

Stay with me for much more from my guest, it’s Chip Conley, he’ll be back in a couple of minutes with more wisdom I’m sure and we’ll be talking also about “12 Reasons Why Life Gets Better With Age, Learning to Love Midlife” and by the way, I love midlife, I think I’m much better now than I was when I was in my twenties and thirties but I’m sure, and I’m sure my friends and family would agree.  Right now though we’re going to hear a taster from the Mishcon Academy Digital Sessions, which can be found on all the major podcast platforms.  Mishcon de Reya’s Emily Knight talks to Charlotte Yonge, a fund manager at Troy Asset Management about how firms can actively encourage diversity when recruiting. 

You can enjoy all our former Business Shapers on the Jazz Shapers podcast and you can hear this very programme again if you pop ‘Jazz Shapers’ into your favourite podcast platform.  My guest today, I am super pleased to say, is Chip Conley, founder of Joie de Vivre, what a great name, the second largest boutique hotel operator in the US, as was, and co-founder of Modern Elder Academy, the midlife wisdom school.  We were talking before about your role as the CEO whisperer, you put your ego in the locker room before you came in, which sounds to me like you were very happy to do that by the looks of things.  What was it like in those years at Airbnb because you were there for a few?  Did you watch the child become the adolescent, become the adult as a business but without losing its sense of spunkiness and of disruption?

Chip Conley

Yeah, quirky, spunky disruption, while having to scale globally and be a disruptor but I, but hopefully a friendly one.  It was quite a fascinating journey.  Four years full-time, three and a half years part-time.  I think what I noticed more than anything was Brian as the CEO, who I was mentoring, really matured as a leader.  His background was that he was a designer and a creative from Rhode Island School of Design but he had no background in business at all and so my job was really to help him be a phenomenal leader and I’m proud to say that three and a half years after the company went public, it’s, he’s still the CEO and the company had to mature, you know, when I joined I was 52 and the average age in the company was 26.  They called me the ‘modern elder’ because not just I was so much older but they said I was someone who’s as curious as they are wise and I like that so I was like, oh I’ll be alchemy of curiosity and wisdom but that’s what I tried to introduce in the company, how do we get curious, how do we get wise and how instead of trying to be the smartest person in the room, how are we the most curious or the wise person in the room because generally, tech companies in Silicone Valley are full of people who want to outsmart each other and that doesn’t create a great culture.  So, I’m proud of the culture that I helped shape along with the founders and it was quite a journey for me because I also had to be an intern as much of a mentor because I had never worked in a tech company before and so I was often the dumbest person in the room but by being curious, sometimes I would ask questions that were like ‘oh wow, Chip just found a blind spot here’. 

Elliot Moss

And, you know, this is a company we’re talking about which is super successful, it’s one of the, probably the most Top 10 most famous companies that have emerged over the last few years anywhere in the world.  If there were one or two things that you could pick on that underpinned why it’s been sustainably successful, what would they be?

Chip Conley

Well, to the founders’ credit, there’s never been a company that got to the valuation of Airbnb over a $100 billion, where the three founders stayed involved.  Joe is no longer as involved but for a dozen years, you had three founders and that was hard because they had their times where they were at odds with each other because of personality types or even strategy.  So part of my job and a couple of the other senior people was to make sure the three of them saw each other’s value so I think that was one thing.  I think the fact you had a very vibrant culture and we invested in that culture was essential because one of the things that happens as you grow is you have this juxtaposition of scaling versus soul.  Scale versus soul and so the culture was where we invested in that soul and so, new people coming, I mean if you’re more than doubling the number of people every year coming into the company, there are a lot of people who don’t know the history. 

Elliot Moss

Absolutely.  And this is, you know, this is the conundrum for any business scaling and I’m sure anyone who’s going even from 10 to 20 or from a 1000 to 1500 or whatever it might be people-wise.  So, so just again, give me one, I want one little, little clue as to how you would ensure that the soul, that the culture is protected even as you really get big.

Chip Conley

Yeah, let me give you a specific one.  We did something called ‘One Airbnb every year’.  We had people in 22 countries, this is pre, before remote work, 22 offices around the world.  Once a year we brought everybody, every single employee, ultimately that was 3000 employees the last time we did it while I was there, and we had a four day festival that dedicated to helping everybody feel like they understood the company, where we were going, our strategy and feeling connected so, that’s a good example.  It was expensive to do that but it was worth it.

Elliot Moss

You talk a lot about wisdom, you talk a lot about the beauty of growing older and the wisdom that comes with it.  I assume that therefore the foundation of your thoughts around the MEA, the Modern Elder Academy, it was all about that, was about saying well how can I bring more people into the fold, how can I proselytise?  Is that right or was it something a bit less noble than that?

Chip Conley

No, it was, the point of view of like hey, I hated my late forties, I’ve loved my fifties, what the heck is going on with midlife?  Is it a crisis or is it a chrysalis?  Chrysalis being that midlife stage for a butterfly where it’s dark and gooey and solitary but it’s where the transformation happens.  And so, I think for me I really thought about my five male friends who took their own lives and thought about the fact that wow, what if there was a school or some tools or a right of passage or ritual that someone can do in midlife to understand how to reimagine and repurpose themselves and so that’s how MEA came about and, yeah, we’ve had over 4000 people from 47 countries come to our Baja campus, which is just down the beach from where you popped the question, is that right?

Elliot Moss

I did.  It’s absolutely true, I, back in, I think it must have been 2011 or 2012, I stayed in a hotel called Rancho Pescadero, which is in Baja, Baja, California, near where I’m talking to you now, I’m not jealous at all, obviously.  And I did indeed pop the question there and listen, what a spot and I look at you in your, you’re in this fabulously, it’s a very, it looks like a nice tall ceiling, classic kind of Mexican architectural kind of New Mexican architecture and I am a little bit jealous, it’s got to be said, Chip, it’s got to be said, you, you, I’m like I want to transport myself. 

Chip Conley

The fact that we have our two campuses and one is in, on a beach in Mexico and the other one is on a 2600 acre regenerative horse ranch in beautiful New Mexico, you know, I feel very lucky.  But yeah, the 4000 people came from all over the world to try to reframe their relationship with aging, navigate their transitions, cultivate their purpose and learn how to own their wisdom because a lot of times what is obvious to us, is wisdom to someone else, it’s just that you’ve gotten so used to it that you didn’t realise how valuable it is and how twenty years ago, you didn’t know that.

Elliot Moss

And how have you, how has this been received?  I guess, obviously 4000, you know, alumni would say, yeah, it’s kind of working.  But what is that people…

Chip Conley

It’s working.

Elliot Moss

What is that people get that they can’t get on their own by thinking about these things?  What are you giving them?

Chip Conley

Well, first of all, we give them a framework and some tools and practices that help them to understand how to navigate transitions and cultivate purpose.  But more importantly, we, you’re in a cohort of two dozen people, a very diverse group of people, and you’re learning from each other because wisdom is not taught, it’s shared and so, for us to curate some conversations, they’re like life-changing, that help people to see, for example, ten years from now what will I regret if I don’t learn it or do it now?  That’s one of maybe a dozen classic questions we have that help people to get clearer on how they consciously curate the second half of their life.

Elliot Moss

Stay with me for my final chat with my guest today, it’s Chip Conley.  And we’ve got some Madeleine Peyroux for you as well, that’s in just a moment, don’t go anywhere.

The delicious sound of Madeleine Peyroux with Getting Some Fun Out of Life.  Well, that’s appropriate, isn’t it.  Well done, Stu, producer, because I’ve been talking to Chip Conley about just that very thing and it’s indeed the, you’ve transitioned, Chip, from building a really creative business in the hotel space, disrupting things, helping the, one of the biggest companies in the world continue to disrupt and as you said, soul alongside the scale journey, and now here you, imparting wisdom and indeed sharing it, as you said.  You’re a writer as well now and I’m really lucky, I get to meet lots of super talented people that are successful.  Some people are really good at writing and some people are really good at doing, it’s very few that are good at doing both.  What is it that you enjoy about the writing process?

Chip Conley

You know when I sit down to write, it’s almost like we’ve put an IV to my soul, it just gives me the opportunity to reflect upon what’s going on inside of me.  So my process of writing seven books at this point has been to make sense of what I’ve learned along the way and to impart that to others so, the newest book is called ‘Learning to Love Midlife.  12 Reasons Why Life Gets Better with Age’.  What I really wanted to do with this book was to help people to see that the world is full of anti-aging messages and products and services but there aren’t a whole lot of pro-aging services or messages.  A Yale academic named Becca Levy has shown that when people shift their mindset from a negative to a positive when it comes to aging, they gain seven and a half years of additional years of life.  And so, this is a public service…

Elliot Moss

It is.

Chip Conley

…because if we can, we really can help people to see that aging has its flaws but also has its upsides, we help them to not just live longer but to live happier. 

Elliot Moss

Do you think this is your purpose because we talk a lot about purpose and people get sometimes a little bit kind of chocolate box about it and they do those nice, you know, it’s the, it’s the bumper sticker that says ‘Hi, I found my purpose’ and all that but listening to you talk and thinking about, at one point your purpose was to make hotels fun and bring a sense of community and a kind of two fingers up to the establishment and all that.

Chip Conley

Yeah.

Elliot Moss

And then it was about helping others in pursuit of growing their business and now, here you are, to me it looks like you’re in the sweet spot of exactly what it means to you. 

Chip Conley

So, it does.  I think there’s four ways to find your purpose.  Something that excites you, something that agitates you, something that makes you curious or something that’s mmm, sort of been forgotten from childhood or early adulthood.  A passion, for example.  And for me, I’m excited, deeply excited about the idea of remaking our relationship with aging, helping people to feel good about being age fluid, meaning you’re not defined by your chronological age regeneration.  So, yes, this feels like my calling but I also think that people need to get, when it comes to purpose, they need to get less worried about the big ‘p’ purpose and focus on the small ‘p’ purpose because you can have performance anxiety about the big ‘p’ purpose, meaning everybody else has one and I don’t have on.  So the most important thing to do in terms of finding one’s purpose is to find the thing that makes you purposeful, do the verb and you’ll find the noun. 

Elliot Moss

It’s been really nice talking to you, Chip.

Chip Conley

Thank you.

Elliot Moss

Apart from my huge, latent sense of wanting to be where you are rather than where I am, apart from that, I’ve parked it, I’m managing that agitation which I know won’t be part of my purpose going forward because that’s not deep enough to just want to be in Santa Fe but thank you so much for you time.  Just before I let you go off and enjoy your day and walk on the beach and enjoy the sun, what’s your song choice and why have you chosen it?

Chip Conley

Bill Withers, Lovely Day. 

Elliot Moss

And any particular reason, beyond the obvious?

Chip Conley

Because every day should be lovely. 

Elliot Moss

Bill Withers there with Lovely Day, the song choice of my Business Shaper, Chip Conley.  “You don’t have to be the hero all the time”, he said of his first business, once he’d finished it, he realised that actually, he didn’t need to do the same thing the next time.  “I had to right size my ego” and he talked about how he became the CEO whisperer in Airbnb and I really liked that expression.  “I created a more multidimensional life”, one of the big lessons he learned after spending so long running and creating his first business.  He helped each of the founders believe and understand the value in the others, I think that’s a really important thing to think about when it comes to founding a business, especially if you’re in a partnership.  And finally, that sense of you can scale with soul but you’ve got to work very hard on the soul and indeed the soul is probably what enables you to grow in a healthy and sustainable way.  Great stuff.  That’s it from me and Jazz Shapers, have a super-duper, wonderful, fabulous weekend.

We hope you enjoyed that edition of Jazz Shapers. You’ll find hundreds more guests available for you to listen to in our archive, to find out more just search Jazz Shapers in iTunes or your favourite podcast platform or head over to mishcon.com/jazzshapers.

Inspired by his experience of intergenerational mentoring as a ‘modern elder’ he Co-Founded MEA in 2018, the world's first midlife wisdom school dedicated to reframing the concept of aging.  

Chip is also A New York Times bestselling author, and his 7th book "Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age" is about rebranding midlife to help people understand the upside of this often-misunderstood life stage and he was asked to give a 2023TED talk on the "midlife chrysalis." 

Highlights

I called it Joie de Vivre, partly because I wanted to have joy in my life.

The money piece of it was never important to me, never has been in fact.

I wanted to create a culture that created joy for our employees and for our customers as well.

I didn’t want to be that person who, on his death bed, regrets not going to Iceland or, you know, not going around the world to experience the world’s best festivals.

Wisdom is not taught, it’s shared.

Every moment matters and I wanted to seize the day.

It was fun to take off my hero’s cape.

I was often the dumbest person in the room but by being curious, sometimes I would ask questions that were like ‘oh wow, Chip just found a blind spot here’.

Instead of trying to be the smartest person in the room, how are we the most curious or the wise person in the room?

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