Chip Conley (00:00)
a wall. I hit a wall on just all every part of my life

be careful about attaching your identity too much to the success or failure of your

company.

When the company died, they died, or they wanted to die. And that's not healthy,

Kevin Holmes (00:14)
Welcome to the Founders Network podcast, where you get the real story, not the highlight reel. You'll hear the decisions, the doubts, and the messy middle of building startups. Today, you're going to hear my conversation with Chip Conley. Chip started his first boutique hotel at 26 with a funky motel in the tenderloin of San Francisco called the Phoenix. And over the next 24 years, built it into a 52 hotel company. Then he had a near-death experience, sold the company, and got a call from Brian Chesky asking him to be his mentor at Airbnb.

He was 52, Brian 31, the average age in the company 26. This is a conversation about what happens after the first chapter. We get into identity, how attaching yourself too much to your company can be dangerous. Chip lost three entrepreneur friends to suicide during the Great Recession when their companies went under. We talked about emotional intelligence, how to empower your team instead of swooping in to be the hero, and the difference between being a librarian mentor and a confidant mentor. Then we got into his current chapter with Modern Elder Academy, where he's helping people in midlife

figure out what's next. What I loved about this conversation with Chip is he was so open about hitting the wall, not wanting to run his company anymore and rebuilding from there. That's what Founders Network is all about. It's founders helping founders for the long haul. Chip showing up to share his story with our community is exactly that. We do these conversations so you can see it to believe it. Chip's story is proof that the journey doesn't end when you sell. just a new chapter. If he can figure it out, so can you. So keep on building and never give up. Chip.

Thanks for doing this with us.

Kevin Holmes (01:36)
All right, so good morning, Chip. All right, so.

Chip Conley (01:38)
Good morning, Kevin. I wish

was in the hood with you in Petraeus Hill. You could do it in person. Yeah.

Kevin Holmes (01:43)
I know your old stomping grounds. I

know. Well, it sounds like you're have a much cooler day in store for you later today meeting with Rainn Wilson. Yeah.

Chip Conley (01:52)
Yeah,

Dwight on The Office. He's been on my podcast, The Midlife Chrysalis, and I am on his podcast, Soul Boom, this afternoon.

Kevin Holmes (02:00)
cool. It's a whole podcast tour. Well, welcome to the welcome to the founders network podcast. This is our second ever recording, but we've been doing these for the last, probably since COVID if not earlier. I mean, for the last 15 years of founders network, we've done a ton of webinars, even before it was cool. Go to meeting. and then it was WebEx and then we built our own using Twilio and then everybody blamed us for the latency instead of.

Chip Conley (02:02)
Yes, it is.

Kevin Holmes (02:24)
Go to meeting or WebEx and then finally Zoom fixed it. And then we just decided, you know, let's just do a conversation in Riverside and have like a little better product and a little more produced. So anyways, yeah, just to kind of catch you up. I don't know if you recall the context of our initial conversation. Okay, cool. I did read your book, The ⁓ Midlife Manifesto.

Chip Conley (02:45)
Learning, the midlife manifesto, okay, yes. That doesn't take long. Yeah.

Kevin Holmes (02:47)
Yeah. Yeah. So I had that on my nightstand. Yeah, it was, it was an easy one.

but super cool. I've read like transitions and some other books, you know, over the years I'm mid forties and I love the concept of it. And I love the whole modern Elders, story and, and what you're doing now. And so I thought like, we could have a conversation. This is founders network podcast. So it's for founders.

obviously tech founders and you've got a lot of wisdom to share. And so we want to try to get that, those messages for the founders in the conversation. And I thought we could just start with, you know, a little bit more of a introduction from you of your background and your story. And then we kind of get into some of these key ideas that we want the founders to learn about.

Chip Conley (03:27)
Sure. Yeah. I mean, my career has three chapters. The first chapter was when I was 26, couple of years out of Stanford Business School. And I started the world, one of the world's first boutique hotel companies. And it was based in San Francisco. And over the course of the next 24 years running that company, we went from one funky motel on the tender line called the Phoenix, to 52 hotels around California.

hit a wall. I hit a wall on just all every part of my life and

Didn't want to do it anymore. was the great recession. So I really couldn't run away from my business and I couldn't sell it very easily. And so I just strapped myself in and dealt with two years of really difficult times and got to the other side of it. I sold the company. Joie de Vivre is now called JDV and it's a Hyatt brand.

So I had a little bit of time between 50 and 52 to think about what was next for me. I enjoyed my entrepreneurial journey, but I also had felt at times like my sense of identity was too attached to the company, which is a very much of a familiar kind of thing from a lot of founders, especially founders in their 20s, 30s and 40s. I do think that as we get older, we realize that our life is much more than just our business card or our company identity.

And so I spent two years between 50 and 52 doing sort of a deep dive on what made me curious in life. I was the first founder, founding board member of Burning Man. Who knew Burning Man had a board? so I was, yeah, long history with Burning Man and the founders that asked me to be their first board member. I joined and, and, and so I was really curious about.

Kevin Holmes (04:47)
Yes.

It is a surprising fact.

Chip Conley (05:10)
festivals of all kinds. So I spent between 1552 going to festivals all over the world, went to 36 festivals in 16 countries, festivals of all kinds, including religious pilgrimages. mean, just really interesting stuff. I got really interested in emotional emotions because I really struggled with my emotions in my late 40s. I wrote a book called Emotional Equations that became a New York Times bestseller. And I was also curious with Hot Springs. So as I went around the world,

checking out the world's best hot springs. So I really sort of rewarded myself from 50 to 52. But at 52, I got a call from Brian Chesky, the founder, co-founder and CEO of a little tech startup I'd barely heard of. This was in late 2012. And the company was really quite small. And most people had never heard of it. And so Brian said he wanted me to be his mentor.

but also in-house, like full-time. And I couldn't do full-time initially, but I did move into full-time quickly. Ultimately, he called me his modern elder, which I was like, fuck you. I didn't like the term. was like, I'm not elderly, but I was 52 and he was 21. He was 31. The average age in the company was 26. So yeah, relatively speaking, I was an elder. And then he said to me the thing that really got to me, which is like,

He said, ship a modern elder, someone who's as curious as they are wise. And I was like, wow, that's what I want to be when I grew up. The combination, the alchemy of curiosity and wisdom. And so I spent seven and a half years there, four years full-time, three and a half years part-time, helping the company go to its IPO when it became the most valuable hospitality company in the world. And during that time, I started percolating a new book in my head, which is called Wisdom at Work, The Making of a Modern Elder.

And while I was writing that book down in Baja where I had a home on the beach, I one day went for a run on the beach and I had a Baja, an epiphany. And the epiphany was, why are there no places for people in their 40s and 50s? As it turns out, it's a broader collection of people who come to MEA now. But why isn't there not a place for people in their 40s and 50s to reimagine and repurpose themselves? I could have used it. I certainly could have used it. And ⁓

I lost five male friends to suicide between 2008 and 2010. And three of the five were entrepreneurs. And so that was during the Great Recession. So I thought, God, this is something that's needed in the world. And so I started the Modern Elder Academy, MEA. And we now have over 8,000 alumni from.

60 countries, and we have 56 regional chapters, and about a quarter of the people who come to MEA are millennials who are really interested in looking at how do you develop your own wisdom and how you develop wisdom on a leadership team. So that's my not so brief intro.

Kevin Holmes (07:44)
I mean, it's an incredible journey. And you've done a lot in this sort of second act after the hotel part of your journey of the first 20 plus years coming out of Stanford Business School. I wonder if we can talk about that a little bit and dive into it because I think that's kind of the formative experience, I guess, that sets you up for this midlife second act, right?

and diving into these topics around emotional intelligence and curiosity and wisdom. For those 20 plus years, we talked to lot of founders here who are 20 year overnight success stories, And resilience and just never giving up. And then sometimes you talk to them and they say, hey, I wish I could have just shut down at 10 years and started a new thing and done another one. Do you have any reflections on that part of your journey that like

You wish you would have known then that you know now maybe that would be relevant for a founder who's eight or 10 years in.

Chip Conley (08:36)
You know, it's really hard. know, my friend Seth Godin, who I went to business school with, and, you know, we are close friends for 40 years now, or actually 40, almost 45 years now. He taught, he had a book called The Dip. And the whole, whole premise of The Dip is when you go through a dip, whether it's a financial dip for the company, an emotional dip for yourself, how do know you're coming out of it? And,

You know, for me with, was Joie de Vivre of my boutique hotel company, we had the.com bus 9 11, which was a big dip, especially for hotels in the Bay area. And then we had a couple after we got out of that, we had a couple of good years, and then we went into the great recession. And during that first step.

I felt like a gladiator. I really did. I felt like I was learning. I had a curiosity about, what can we learn from this? I felt like a leader that people wanted to work with. I felt like a magnet. And we did really well. I ultimately wrote a book called Peak, How Great Companies Get Their Mojo From Maslow based upon that experience. And I really built a business philosophy around that.

But what I can say is that when I went into the Great Recession, I was already going through an emotional dip. I was already in a place where I didn't really want to be running this company anymore. And I had a long-term relationship ending. And I have a African-American foster son who is an adult who is going to prison wrongfully. And I was losing faith in suicide. And I was running out of cash. And had an NDE, a near-death experience, ⁓ because of allergic reaction to antibiotics. So I was like, OK, how many things like

Kevin Holmes (09:55)
Hmm.

Hmph.

Chip Conley (10:06)
I could have grit

Kevin Holmes (10:06)
Is that all?

Chip Conley (10:08)
and resilience, at some point, you know, I didn't feel like a gladiator. I felt like a gladiator during the dot-com bust, but I did not feel like a I felt like a prisoner. And so one of the things that a friend of mine who's a coach said to me, she said, Chip, why did you start Juataviv in the first place? And that was over 20 years earlier. And I was like, well, I think it was because of the creativity and the freedom. And she said, do you still have that? And I was like, no, not at all.

Kevin Holmes (10:15)
Yeah. Yeah.

Chip Conley (10:32)
And she said, is that still really important to you? I said, yeah, it is really important. It's not the only thing that's important. Back then, might've been the primary thing, but it's really important to me. And she said, well then how do we get creativity and freedom back in your life? And she asked that about a week before I had my Flatline experience. And it was like, okay.

And I was really stumped by the question. I did not know how I could get creativity and freedom back in my life because at that point I was just bailing water from a sinking ship during the Great Recession. We launched 15 hotels over 21 months between the end of 2007 and mid-2000 or summer 2009, which was not a good time to be launching a bunch of new hotels. And so...

The NDE really woke me up and just said, and I don't think everybody has to have an NDE to like make a change in your life. You can come to MEA for that with it. lot less stressful. But I think what I really got from it was this idea that, you know, if creativity and freedom was so important to me, and I think I really am a creative person, I'm an innovative person, but I now feel like I'm stuck. You know, maybe I need to bring somebody in.

Kevin Holmes (11:17)
Thanks.

Yeah

Chip Conley (11:37)
And so I did elevate my COO to president, but I didn't really have a CEO candidate. And I really just knew that, okay, I think this chapter of my life is done. even though I was so identified with, I that's like a mini version of Richard Branson. So Richard Branson, Virgin would not be the same without Richard Branson, right? So Zoradovich, the way people would say to me, like, Zoradovich would not be the same without you. So I was like, I'm so stuck, I'm attached.

Kevin Holmes (11:48)
Hmm. Hmm.

Mm-hmm.

Mm-hmm.

Mm-hmm.

Chip Conley (12:04)
And for a lot of my career, that ego attachment gave me a lot of, you know, lot of perks. But by the time I got to this age, the age of my late 40s, the perks didn't matter anymore. What really mattered was I wanted to be able to wake up in the morning and not worry about how we were making payroll that week. And so.

Kevin Holmes (12:17)
Mm-hmm.

Chip Conley (12:24)
I had to get to a place where I just realized that, okay, I can find creativity and freedom somewhere else. I just need to land this plane. And that was my job for two years, was to just to a place where I could, without bankruptcy, I could sell the company. I sold the management company and the brand to a guy named John Pritzker, whose family started Hyatt. And then ultimately he sold us.

Kevin Holmes (12:33)
Okay.

Chip Conley (12:46)
sold Joie de Vivre to Hyatt. But I was able to sell it. I kept my ownership of the real estate, which was very smart, because over the next few years, after that great recession, the real estate of the hotels that we owned went way up. So I made a lot of money on that. But I didn't make a ton of money after 24 years and three years in a row of not taking a salary. When I sold, I sold it for enough money to feel good, but not enough money to feel great. ⁓

Kevin Holmes (13:03)
Hmm.

We're going to

Chip Conley (13:14)
But thank God, you know, I kept the real estate and thank God for Airbnb because that really, you know, I made a, yeah.

Kevin Holmes (13:19)
That worked out.

it sounds like, know, there's every story is everybody has a different story, but in your case, you kind of got into it for certain reasons and it happened to be about, you know, hotels, but it was really this creativity and this freedom. And at a certain point that ended.

Chip Conley (13:36)
Yeah. I mean, the process of launching, you know, 52 boutique hotels over 24 years was exhilarating. It's a lot and I loved it. And we had a process for doing it that was, you know, got a lot of attention and we were innovating and getting a lot of attention for what we were doing. And I, and it was very, creative, but it was sort of like, you know, I like making babies. I just don't want to raise them.

Kevin Holmes (13:42)
Yeah, it's a lot. Yeah.

That's great.

Chip Conley (14:02)
And it was 52 hotels plus

23 restaurants plus six spas. mean, was not, was, was, you know, eight over 80 businesses.

Kevin Holmes (14:08)
Yeah.

I see, yeah, yeah, yeah. So each one is this creative act. And then there's the operation side. So maybe the takeaway for founders is just kind of get it like understanding what kind of founder you are. Are you the one that likes to birth new things or are you the one that likes to be the steady hand and kind of, and usually you're the former, not the latter. ⁓ Yeah.

Chip Conley (14:26)
Yeah.

That's true. And I had skills

in both. mean, thank God, thank God I had this, you know, I had some business school background so I could, I can run the company, but I, that was not where my joy was for sure. And so I probably should have run a branding agency and that's what I should do. But you know, the nice thing about actually being the CEO of a company that was creating the hotels is if I was a branding agency, I could make all these recommendations, but, you know, who knows if the clients actually.

Kevin Holmes (14:44)
Yeah, yeah.

Mm-hmm.

Chip Conley (14:56)
So I had the freedom, that, know, creativity and freedom, the freedom to do the things that I was cooking up in my brain. But I also would say another lesson from all this is be careful about attaching your identity too much to the success or failure of your company. You know, to lose three, five friends, but three of them entrepreneurs.

Kevin Holmes (15:18)
Yeah.

Chip Conley (15:18)
all three other companies went under during the Great Recession. It was almost like their sense of identity of who they were was 100 % attached to their company. When the company died, they died, or they wanted to die. And that's not healthy, obviously. And There's a Rudyard Kipling poem called If. And it's about the idea, don't.

Kevin Holmes (15:38)
Hmm.

Chip Conley (15:41)
Don't, you your worst and your best days, don't judge your life based upon those. And it's a beautiful poem that every entrepreneur or founder should read.

Kevin Holmes (15:50)
It's wonderful. Yeah. I'll have to check that out. I, I, this idea that the founders tend to attach themselves with their startup. You are your startup and, and then losing friends probably because of that, right. And the, and the hidden costs of doing a startup of this career choice, I think of it like a vocation or a calling. Once you do one startup, you want to do another. And that's the vision of FN is a lifelong support group for founders as much as it's tactical A to B it's.

emotional runway and cathartic kind of venting and having a group that understands you. So this very much is what Founders Network is about. It's very much about my experience doing a startup, experiencing burnout and having a friend pass away that really just changed the course of my life to start Founders Network. everything you're saying, it really resonates. And I think it helps you focus in on what matters.

And then, you know, what's interesting too about what you're saying is yes, you're not your startup and don't judge yourself on your worst or your best days. ⁓ and, then the other end of it too, if you're not, if you're not attached enough to it, right? Maybe this is for the millennial audience. like you, you can't, you're not going to succeed in a startup if you're, if there's not, if you're not vested in it. So what, what do you think the right kind of asterisk is on that statement of like, you know,

How much of you goes into this?

Chip Conley (17:03)
Well, I think that's a good question. ⁓ First of all, learning how to have a team supporting you is essential. I've learned that with Modern Elder Academy, with MEA. But when I was, know, the CEO and founder of Joie de Vivre I didn't really groom a successor. I sort of had one in the wings, but he was really young and he was a little brash and

Kevin Holmes (17:06)
Yeah.

Chip Conley (17:26)
and didn't really have the humility needed for the company. So when I had my NDE, I just realized, you know, I'm, I have, I've not prepared the company well in case something happens to me. today I have, so I think having a team of people is really essential. number two is, you know, whether you have a fat co-founder or. Partners, you know, leaning on them and making sure that they are.

they have their skill set that is reciprocal to yours. They're not redundant to yours. And so essential because every company is going to have some era where the operations piece is really important or the sales piece is really important or the going out and raising money or the capital piece is important.

Kevin Holmes (18:04)
Yeah.

Chip Conley (18:11)
If you think that you can do all of that exceptionally well, then you're a better person than me. You really need those experts in those areas, whether they're co-founders or whether they're just senior leaders. And you need to empower them. I love one of my favorite phrases is give people a reputation to live up to. So you hire people based upon their potential and their experience.

Kevin Holmes (18:17)
Yeah.

Chip Conley (18:36)
And what you want them to do over time is to live up to that potential. So one of my favorite questions as a founder and a CEO to ask my direct reports is how can I support you to do the best work of your life here at Joie de Vivre Airbnb or MEA? How can I support you to do the best work of your life here at whichever company? That question is a really important question because what it does is it helps the people around you.

realize you want them to do their best work. You want them to be successful. But it also puts agency in their lap to say, your job is to tell me what you need to be successful. And it allows you as the leader to sort of give some responsibility to them to have accountability and agency. And then you have to listen to them. And they may come up with 24 different ideas of what they need. And you may be able to only do 10 of them.

But at least you're having the conversation. And so I have found that question to be really helpful. It also helps people to step up. And when people know, I want you to do the best work of your life here, then sometimes people have said to me, if I'm going to do the best work of my life, you've got to give me some more responsibility. You've got to give me some more agency to make decisions. Sometimes you swoop in, Chip, and you become the hero, saving the day. ⁓

Kevin Holmes (19:31)
Thank you.

Mm-hmm.

Chip Conley (19:50)
And while they wouldn't say it, but I will, you know, my ego was stroked in the process of doing that. That was one of the things I had to teach Brian Chesky at Airbnb. know, I had seen it in myself is I love to come into a meeting. you know, for me, it was coming into a design meeting with the designers and the concepting people and naming the hotels and a new hotel and the branding. And I'd swoop in having not been part of the earlier meetings and like do things. Brian did exactly the same thing at Airbnb, but it wasn't.

Kevin Holmes (19:55)
I think.

Yeah, yeah.

Mm-hmm. Mm-hmm.

Chip Conley (20:19)
boutique hotel design, was instead, it was the UX and the UI for the Airbnb website or, or a marketing campaign we were doing. And I was laughing early on because I was like, wow, I've seen this picture before and my job. That's why I was, you know, his mentor and the wise one was to be able to take him aside, not, not interrupt him in the meeting, but take him aside and say, you know what? Here's, you open to some advice or some feedback about, about how that meeting went?

Kevin Holmes (20:30)
Yeah.

Yeah.

Chip Conley (20:45)
And, you know, I would say in some of these meetings, I would say something like, you know, you could have engineered that meeting a little differently so that your VP of marketing could have actually stepped up and had the solution, but instead you supplied the solution.

Kevin Holmes (21:01)
Hmm.

Chip Conley (21:01)
And then

you took away that agency and that sense of pride that that person had that they could have actually gotten there. You could ask some questions as a delivering answers. But if you're like Brian or me, you know, in our jobs, we are so fucking efficient, excuse me, but we're so fucking efficient of like, I got to go to the next meeting and I don't want, I don't want to wait for the punchline. I want to tell you what the punchline is.

Kevin Holmes (21:08)
Mm. Yeah.

Yeah.

All right. This is where we transition to the founder mode topic. But, you know, I think to put a cap on the first 20 plus years of your career, you know, you are not your startup and, and that also means empower others and groom others to help you with this effort as, know, as a key takeaway for you and for other, for other founders like this VP of marketing with Brian Chesky that you mentioned as well. Right. And

What it makes me think about is how we're control freaks as founders and how we can get really myopic. And that to me connects with your friends who passed away is part of that identifying with the startup is you're just too myopic and deep in and tight and focused around the startup and some practice of zooming out of letting go and stepping back from it. You had a coach that helped you with that in that transition into your

your festival years. Did you have a coach all the way through with with it was a later thing.

Chip Conley (22:20)
Now, I really didn't notice

it was my friend, Vanda, the coach really stepped in after my NDE. And it was during those last two years after that, that we were selling the, was going to figure out how to groom the company to be sold where she was really helpful.

⁓ doesn't mean she hadn't done some things. She had actually done some, some leadership retreats with us and things like that, but she hadn't been sort of an ongoing coach. I will say that I was in YPO back then. ⁓ and I, you know, they, you know, I was in a forum and in my forum, I got a lot of, a lot of help. So I think founders network is spectacular because it creates the crucible for really, you know, important deep conversations.

And sometimes those conversations are about things that are not going well. And one of the challenges with the founder world often, especially in the Bay Area, is this sense that you want to present a confident and successful theater. quietly inside, you're just quaking in your boots. You're really nervous about.

Kevin Holmes (23:13)
The success theater, yeah.

Chip Conley (23:24)
the state of things and who do you talk to about that? And in a intimate peer-to-peer network kind of format, you can have those conversations, but even better with those people than with a coach. And a coach can be helpful. I there's some great coaches out there, but a lot of times a coach has never been in your shoes. A lot of most coaches I know have never been an entrepreneur or a founder.

as such, they don't really completely understand. Now, if all they do is they do like Edward Sullivan, I love the guy, Velocity Coaching, I teach with him. In fact, we're teaching together at our Baja campus in early March. You know, he has been a founder, but he's also been around enough founders at this point. He understands the psychology of the founder. And he...

doesn't just listen to for what the person's saying, he listens for what they're not saying. And that's where it really gets interesting is your blind spots. And so who sees your blind spots, whether it's a coach, whether it's your spouse, whether it's your co-founder, whether it's your best friend, whomever it is, we as entrepreneurs need people to point out our blind spots. Now that's not easy. And it's really easy to react to that.

Kevin Holmes (24:12)
Hmm.

Chip Conley (24:31)
and learning how to take a space between stimulus and response when someone's telling you something that's not easy to hear. If you can believe that they are saying this for your best interests, then that helps. Now, if they're not, mean, if they're like, you know, ⁓ someone who's trying to take over the company from you or whatever, that's a whole different story.

Kevin Holmes (24:45)
get tripped.

Chip Conley (24:52)
I would say the majority of the time when someone's giving you that feedback, they may be giving it to you for your best for you, for what's best for you. And you may not agree with it, but be careful about the reaction. You know, take it under advisement. Say like, you know what? I hear you. Here's what I'm hearing from you.

Kevin Holmes (25:00)
So, be careful of reaction.

you Hmm.

Chip Conley (25:10)
We are you open to actually sending something to me in email because I'm hearing your words right now and I feel like I'm sort of like a pinball in a pinball machine. And I just sort of want to like read what you've just said to me. So send me something

so that I can read it and just like take it in ⁓ because I really want to I want to try to hear what you're saying. And right now I'm maybe not hearing it the way the way you want me to. Now, someone who can do that is emotional intelligence.

Kevin Holmes (25:27)
Yeah.

Mm-hmm.

Chip Conley (25:39)
And emotional intelligence is two thirds of the success of business leaders is their

EQ as opposed to their IQ or their level of experience in the job.

Kevin Holmes (25:47)
Yeah, I think the best founders have this coachability. And that was your role at Airbnb was really coaching Brian Chesky and yeah.

Chip Conley (25:53)
Yeah. That's part of my role. I mean, was also running part of

the company. I mean, was running a big part of the company. And so I had an actual operating role, which frankly was not my original plan. My original plan was I was going to mentor. Well, I was going to do the three founders and it was going be 15 hours a week. And then about three to four weeks into it, I had been sucked into 15 hours a day. And I said to Brian, like, okay, you got to start paying me. Because initially I was doing it for free.

Kevin Holmes (26:06)
Couldn't help yourself.

Ha ha ha.

Chip Conley (26:20)
And I was like, gotta start paying me and I'll clear the deck. So I can see this is a rocket ship and I need need and want to help you steer the rocket ship. And I got to do that full time. so I changed everything. And then I went on a world tour, which was really interesting where I went around the world to I think 14 different markets. This is also at the same time I was doing my festival tour. I was finishing my festival tour.

Kevin Holmes (26:36)
Interesting.

Chip Conley (26:46)
As I was starting my Airbnb tour, I'd and see the hosts. My job was to go around the world and listen to hosts. And I came back with an amazing 10 lessons that Brian and Joe and Nate were like, wow, know, the hosts would never tell us these things because we're the founders. And you didn't just tell us what the hosts were saying. You also said, here's the

Kevin Holmes (26:47)
Okay.

Mm-hmm.

Chip Conley (27:09)
Here's the plan for each one, how we're solve each one of these 10 things. And that's when Brian said like, okay, you're head of hospitality for the company. We already knew that, but like now you're the head of strategy for the company too. And it's like, okay, okay. But I'm also your mentor. ⁓ But I reported to Brian, let's be honest. I was mentoring Brian, but I was the head of global hospitality and strategy. And so I was reporting to my mentee who was 21 years younger than me. And I really needed to right size my ego.

Kevin Holmes (27:22)
Yeah.

Chip Conley (27:37)
in order to that. And my job became not getting my name in the lights, which is what I did quite often when I was at Joie de Vivre. But my job was to make sure when Brian's name was in the lights, and it was a lot, was to make sure that he lived up to the leadership reputation he was building.

Kevin Holmes (27:49)
But.

Chip Conley (27:53)
And I'm proud, you know, over five years after the IPO, Brian is still leading as a CEO, a Fortune 500 company that is still the most valuable hospitality company in the world. And he has his faults for sure. But for somebody who had zero background in business and started this just two years out of Rhode Island School of Design, I'm pleased to see he's still running the show.

Kevin Holmes (27:56)
Thank you.

Yeah, something worked there. think what, what, what did you learn about being a mentee, being a mentor? We talked about coachability and EQ. w you know, that, that's a shift. I also want to touch on your world tour and like the importance of talking to customers and how did you get them to give you information that they wouldn't give the founders? I was it just a title thing or is there a alcohol tried and true? Yeah.

Chip Conley (28:39)
Alcohol. Well, definitely Asian countries in Seoul

and Tokyo and did help Beijing as well. Long story short, I think what I learned from my experience with Brian was I was a mentor and an intern at the same time. I joined a tech company at age 52 and never worked in a tech company before, so I didn't understand the lingo.

Kevin Holmes (28:45)
but

You

Chip Conley (29:05)
I was a boomer surrounded by millennials. I really had to adapt and learn about venture capital because I'd never dealt with venture capital and as a hotelier. So it was an opportunity for me to learn. And I had to have enough humility to be open to saying, I'm the dumbest person in the room right now, and I'm here to learn. I'm going to be curious. At the same time, I was a mentor when it came to emotional intelligence and leadership and strategy.

and recruiting and culture. So it was a symbiotic relationship between me and Brian. ⁓ And as of 2027, according to the US Department of Labor, the majority of Americans will have a younger boss. The majority of Americans. So we've never seen that before. So I got to sort of see a flavor of what was coming.

Kevin Holmes (29:38)
Bye.

it

What?

Chip Conley (29:51)
So I would say that is a key lesson. I think another lesson that was that when it comes to mentorship, there's two kinds of mentors. There's the librarian and the librarian has all the know how, know who, and a librarian answers questions. I was, most of the people I mentored were that looking for that kind of mentor. And then there's the confidant, which is the more in-depth kind of mentor, which is my job is not to answer questions. My job is to ask questions.

Kevin Holmes (30:01)
Mmm. Mmm.

it.

Chip Conley (30:17)
And

my job is to give you confidence. So a confidant gives you confidence. so I realized that these are, when I was talking to someone in the company and they wanted me to be a mentor, I needed to size them up and say like, OK, is this a librarian relationship where I'm just answering questions, or is this the more in-depth kind of relationship where I'm asking the questions? And that was a great experience. When it came to the world tour and all of that, I'd say,

Kevin Holmes (30:30)
⁓ huh.

Chip Conley (30:42)
What helped was, what I think was going on was the founders wanted to hear things. They didn't necessarily want to hear the bad news. They sort of wanted to have some kind of rah rah out there in the host community that gave them the confidence that they were on the right path. And

So that could be self-selecting. if somebody was showing up at a host event in Rome to actually complain about something, what often happened and what I heard and then saw is the guys would listen, but then they'd actually bring somebody else in because it would get into the weeds pretty quickly about what was going on that was frustrating. And they wanted someone else to solve it and they didn't have time to go into the weeds. so...

Kevin Holmes (31:01)
Thank you.

Chip Conley (31:21)
What I, in the early days of being there, I had the time to go into the weeds and I had the time to really, and even though a lot of what was going on was tech related. So again, I didn't understand tech very well, I, the key thing was I listened. So the key thing was I was there to listen. Number two is I had the credibility of being a long time hospitality leader.

Kevin Holmes (31:27)
Thank you. ⁓

Chip Conley (31:42)
And many of the, there were really two, there were three primary complaints that I was hearing. One over time that got much worse was regulatory wise, but in the early days it was not so much regulation. But the two key things were tech issues, which I needed to learn and understand how are we going to solve those.

Kevin Holmes (32:00)
And

that's it for this segment. If you want to get more talking, you'll have to stop.

Chip Conley (32:01)
But the bigger one was like, you know, no one had ever taught them any hospitality as

hosts and as entrepreneurs. And so what are the moments of truth? And so from that experience, I realized how much, and we had some caution too, because as a third party platform, we could not force people to go through an education process. Otherwise we were in the direction of potentially being employees as opposed to independent, independent hosts.

Kevin Holmes (32:08)
Mm.

Hmm.

Mm-hmm.

Mm-hmm.

Chip Conley (32:28)
And so I had to, you we had a little bit of a balancing beam. But after that experience, I came back, you presented to the senior leadership team and the founders and the board, and then went on a...

Kevin Holmes (32:31)
Yeah.

Chip Conley (32:39)
another educational tour and that was the chips moment, moment, hospitality moments of truth tour. And that's where I was really teaching them hospitality. And it was, we had to make sure that we didn't force anybody to do anything. You weren't like, you know, but we had to say like the super host program, which had been on life support and which we were getting rid of. I said like, why would we only have 200 super hosts in the world and they're our best hosts. Why would we get rid of it? It's like, well, we're not, we don't have the tech to sort of like support it and

Everybody's like going in, but I said, super host is, is this is psychology. People want to be a super host when they grow up. Super host is our way of telling our guests. This is a better listing. It's our way of telling our hosts. If you do these few things, you are actually going to become a super host. And then you're going to actually have that, you're going to show up more, you know, in a search. So, I mean, so much of what I was doing was really psychology.

Kevin Holmes (33:12)
Mm-hmm.

Huh.

Yeah, that's the word

that was on my mind as you were saying that, And it might be missed in an engineering mindset. This is super fascinating, moments of truth. The moments of truth you mentioned, is that something you developed at Joie de Vivre Yeah.

Chip Conley (33:44)
Yeah, we did have moments of truth there. So

moments of truth are basically, and this could be for any business. I'll explain it for Airbnb in a second. But it's those times when a potential customer or an existing customer is most likely to judge whether they made a good decision or a bad decision as to being a customer. So for example, in the Airbnb flow,

⁓ a moment of truth for a potential customer would be seeing a listing for the first time, not Airbnb, but you know, now you're in Airbnb. We're talking about, okay, how do you deal with the host moment of truth? So the first one is, okay, but you know, what is your, what are the best practices of creating your listing and what, and especially with accuracy, accuracy is a really important piece because you know what, frankly, if you don't get the accuracy thing, right, you create problems later when the person shows up and like, Hey, this is not what

your picture. So that was that point. Then there's other moments of truth, including a moment of truth of like when something goes wrong. Back in the day, as a hotelier, one of my favorite things is to actually turn someone around from being a terrorist to a cheerleader in terms of a customer where something went really wrong. And then we turn them around because that customer

is usually more loyal and more of an evangelist to their friends than the customer for whom everything went right. ⁓ So yeah, hospitality is an amazing turning ground for understanding how do you address customers in a way where they feel heard and seen.

Kevin Holmes (35:06)
Mm-hmm. Yeah.

Chip Conley (35:17)
and cared for. And I was really proud because when I joined Airbnb, our net promoter score, NPS, which a lot of companies use, was about half of the hotel industries. And when I left Airbnb, we were about 40 % higher than the hotel industry. And that was so much of that was

helping the hosts understand how to deliver amazing hospitality and to see that as entrepreneurs, it's in their best interest to do so. And that's the key is where we have to create the incentives, the carrot and the stick.

Kevin Holmes (35:45)
Mm-hmm.

Chip Conley (35:52)
Number one is the carrot. had to have the incentives like super hosts and things like that, that in encouraged hosts to do their best. But we also had to have the stick. And that was a hard one for me when I first joined because nobody on the platform wanted to get rid of bad hosts. We spent

Kevin Holmes (36:02)
I'm not going

Chip Conley (36:08)
a lot of money and time to get hosts, get rid of bad ones. And I was like, okay, well then we got to train them. Well, we can't train them Chip because if we train them and send them to, know, remedial school, then they become employees.

Kevin Holmes (36:10)
Mm-hmm.

Look.

Chip Conley (36:21)
So there's a really interesting dance for me because quality, I would say that one of my biggest responsibilities in the days at Airbnb was quality. How do we get Airbnb to a place where people see it as potentially quality? And I always said like, okay, it's not about being the most consistent, that's holiday in. Holiday in will be consistent. We need to be dependable. And the difference between consistency and dependability,

Kevin Holmes (36:23)
Hmm.

Yeah.

Chip Conley (36:44)
is consistency suggests it's the same thing over and over again, which is boring. And that's what a chain hotel does. But dependability is you expect something, disappointment equals expectations minus reality. How do we make sure that we manage expectations properly? And how does a host do that with a listing? How does Airbnb do it? And then when reality is less than expected, how do we?

come back. And it's hard to do that in a global platform growing as quickly as Airbnb was.

Kevin Holmes (37:11)
Yeah, it's interesting. So much of entrepreneurship is just expectation management. ⁓ Yeah. And so I love these frameworks. I'm cognizant of time and I want to make sure we talk about, you know, like we did with Joie de Vivre the Airbnb era, like if you look back at it as something that's with you today, then if you would think about your earlier self as a founder for our audience.

Chip Conley (37:15)
Yeah, wow.

Kevin Holmes (37:34)
you've already shared so many good things. Is there anything else that comes up for you for like, I know that the founder mode topic made the, made the waves, you know, recently in this, this fine line that you walk as a founder of enabling, empowering, letting people, giving people expectations that they can live up to. but is there anything else that kind of comes up for you that you think is, is kind of a, instructive or yeah.

Chip Conley (37:52)
Yeah, would say last

thing I would say, which was why Brian and I got along so well, was a clear alignment around culture, especially for a culture like Airbnb, which was global. By the time I got there, had offices around the world already, and we were like a four-year-old company.

By the time I left, had offices in 22 different countries around the world. And so how you create a culture that is global and tangible. And we as a company, to Brian and Joe and Nate's credit, we invested a lot in culture.

We did something called One Airbnb every year, which we brought all people from all over the world to afford a festival, like a love fest at our Airbnb headquarters in San Francisco. you know, that was expensive to do. And so, yeah, the idea that ⁓ people understood what they were getting themselves into when they joined and the culture evolved over time and that we were investing in culture, all of that was really important.

Kevin Holmes (38:51)
Yeah, yeah, that's often overlooked and it's hard to do it remotely as well. So very cool. And then your more recent chapter with Modern Elder and you've published some books along the way and I want to make sure we go a little bit more in depth on that.

Chip Conley (39:09)
Yeah. Yeah, so I love writing books. written eight books. many of them have been at the intersection of psychology and business. More recently, they've been more sort of psychology and age-related. MEA was created based upon that idea that I had when I went for a run on the beach, which was, why is it that we don't have places where people can reimagine, repurpose themselves?

Navigate the transitions of midlife. I define midlife as 35 to 75, so it's a pretty broad definition. Cultivate purpose, learn how to own your wisdom.

and reframe your relationship with getting older and see the upside of it. Because Becca Levy at Yale has shown that when you shift your mindset on aging from a negative to a positive in midlife, you gain seven and a half years of additional longevity. So for all those reasons, MEA's got started. We have two campuses, one in Baja on the beach, right where I had my original concept come epiphany, Baja AHA. And then we have a 24

6,000 acre campus in Santa Fe, New Mexico. That's a regenerative horse ranch. And we have residential communities too. We have regenerative communities where people live around regenerative farms and things like that. So it's a big, bold idea. And I've been enjoying it. What's nice about it relative to my Joie de Vivre

Kevin Holmes (40:18)
Yeah.

Chip Conley (40:28)
and even the Airbnb area, like, it's all my own money. So I've

poured tens of millions of dollars into it. And I don't really have anybody to answer to except for myself. And I really appreciate that. dealt with partners and investors and owners of hotels we managed, and then also at Airbnb, the Airbnb ride on the investor side was pretty good.

Kevin Holmes (40:42)
Yeah.

Chip Conley (40:50)
Other than what happened with the pandemic, Airbnb, after a really big dip in business, saw that the pandemic was great because the hotel industry fell apart and people got an Airbnb for a month or two and they saw that the platform allowed them to flee urban markets and go to Airbnbs all over the world.

Kevin Holmes (41:01)
Yeah.

Mm-hmm.

Chip Conley (41:13)
and then hunker down. So yeah, I think I've learned a lot along the way. The other thing I've learned with MEA is I've moved from return on investment ROI to ripple of impact. And I think I started doing that at Airbnb. And so the premise there being is like, okay, you know, the transactional side of running a business, you're focused on, you know, the return on investment, of course. But as you get older, you move from, you know, building your resume and your LinkedIn profile.

Kevin Holmes (41:38)
Huh.

Chip Conley (41:39)
to starting to develop what people will say about you at your eulogy. And so the idea of the ripple of impact is something that became very clear to me at Airbnb. But now having a school with over 8,000 students

that have gone through our programs, it's really clear that the greatest reward as we get older is to see that ripple of impact.

because that is so much more than frankly the financial side. Now it does help that I had the return on investment, financial benefit of doing what I've done in my life. Even though frankly, if you'd asked me at age 50 when I sold my company for not a lot of money, I felt like a loser. But I didn't know that Airbnb was coming along. I didn't know that the hotels that I still owned would come back in value and I could sell them for a lot of money.

Kevin Holmes (42:19)
Hmm.

Chip Conley (42:26)
And now I've invested that, you know, in something that to me feels like it's going to last beyond my time on this earth.

Kevin Holmes (42:33)
Hmm. That's fantastic. the, there's a, this, the idea is that there's a sort of gap of like, and not a lot of thinking or focus, you know, you just get old and you die, but there's this, there's a lot of concepts in the, in the manifesto that I think are really important concepts for, um, middle, midlife founders, founders that were tends to be, uh, founders that have, you know, it's lifelong network. So we've got founders that are kind of in that, in that period of their lives.

I know that a lot of them deal with like feeling like there's ageism feeling like, you know, maybe you need to be 18 to 24 to start a company. yeah.

Chip Conley (43:12)
There's ageism on both sides though. there's

be, you know, ageism toward a younger person. So ageism, I want to be really clear. I think that ageism cuts in both directions. And, but on the older side, a famous executive recruiter once said to me, Chip, if you show up, if a person shows up with curiosity and a passionate engagement for what they do, they won't notice your wrinkles. They'll notice your energy.

Kevin Holmes (43:17)
Yeah. Yeah.

Uh-huh.

Chip Conley (43:36)
And people

are drawn to energy. And so I'm 65 years old. I still have a lot of energy and we're drawn to energy. so, especially if you're older and you're showing up with energy, you're playing against type. People think, ⁓ you know, after 45 or after 50, you're not going to be open to new ideas or be curious or, you know, be, yeah, have energy.

If you can play against type, people will be drawn to you.

Kevin Holmes (44:02)
Yeah, I love that. Energy is what, you know, people are following, regardless of age. And you talk about age fluidity and all of these concepts are, you know, I guess the question I have is for, do you have a lot of entrepreneurs that come to modern elder? it a, yeah.

Chip Conley (44:15)
Yeah,

no, that entrepreneurs are a big part of our business. And sometimes they're coming because they've sold a business and they're like, oh my God, I don't know who I am anymore. Sometimes it's because they've had a business, you know, go bad. Sometimes it's they're stressed and feeling like they need wisdom. mean, because we're a wisdom school, midlife wisdom school, the think the greatest benefit that a lot of our founders get is understanding.

Kevin Holmes (44:23)
Yeah.

Chip Conley (44:38)
And so we have these wisdom management practices and these wisdom workshops. You're specific to that. And those are really popular. But also the workshops that are focused on people who are, have sold and they just don't know who they are now. What's next? Who am I? That's a huge one.

Kevin Holmes (44:54)
Yeah, you hear that a lot. Yeah.

You at 50. It was kind of that. And you're building it for yourself at that point in your life. Yeah. And when they come to this, can expect to walk away with a practice for developing wisdom and making sense of their experience. Yeah. Yeah. OK. So how often do you do these? What would founders and founders of our community? OK.

Chip Conley (44:59)
Yes.

That's right.

Exactly.

We do 120 workshops a year. do,

we have workshops happening every single week of the year at both campuses. Plus we have two retreat centers at the Santa Fe campus. So we have even more there. And then we do a lot of private retreats and sometimes companies come to us as a leadership team and to say, Hey, we want to

We want to become a wise company as opposed to just a smart company because quite frankly, all the world's knowledge is on my phone now. And so the question is, if knowledge has become a commodity, maybe wisdom is scarce and it's even more valuable. so how do you create wisdom management practices?

Kevin Holmes (45:54)
Hmm. I love that. Well, it sounds like a fantastic thing for any founder in transition as they sell their company and really at any point where they're in the midlife. And the sooner you know this, the better, think, right? All right. I think I have like one final question for you, Chip. ⁓ You mentioned how many festivals was it? 36 festivals. All right. Which festival should everybody attend?

Chip Conley (46:08)
Exactly.

Yes.

36 festivals,

Well, other than Burning Man. I mean, I went to the Maha Kumbh Mela, which is an Indian festival on the Ganges River that's every 12 years with 100 million people when I went in 2013. That's a once in a lifetime experience. I think anybody in the US, New Orleans Jazz Fest is not just about jazz. It's about a community celebration. And I love that one.

Kevin Holmes (46:38)
Yeah.

Chip Conley (46:43)
The Telluride Film Fest is the best film festival in the world in my opinion. Yeah, there's lots more. Yes, for sure.

Kevin Holmes (46:49)
Yeah, that's great. Well, you got to have fun along the way. I that's really important part of this.

Chip, thanks so much for dropping in the Founders Network. I appreciate you. Thanks for taking the time. And we'll make sure we share what you're doing, the good work with Modern Elder, with the community. And hopefully, this will be the, we'll have many more conversations in the future. Yeah, thanks Chip.

Chip Conley (47:08)
Thank you. Thanks, Kevin.