Chip Conley on Reigniting Your Passion - Mind Training for Salespeople and Sales Leaders

New York Times bestselling author Chip Conley is the boutique hotel entrepreneur who helped Airbnb’s founders turn their fast-growing tech start-up into a global hospitality brand. Chip is the founder of the Modern Elder Academy, where a new roadmap for midlife is offered at a beautiful oceanfront campus in Mexico. MEA will be opening up their first U.S. MEA Regenerative Community outside of Santa Fe, New Mexico in 2023.

New York Times bestselling author Chip Conley is the hospitality maverick who helped Airbnb’s founders turn their fast-growing tech start-up into a global hospitality brand. In Wisdom@Work: The Making of a Modern Elder he shares his unexpected journey at midlife — from CEO to intern — learning about technology as Airbnb’s Head of Global Hospitality and Strategy, while also mentoring CEO Brian Chesky. Chip is the founder of the Modern Elder Academy, where a new roadmap for midlife is offered at a beautiful oceanfront campus in Baja California Sur, Mexico. He serves on the board of Encore.org and the advisory board for the Stanford Center for Longevity. www.ChipConley.com

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[Podcast Transcript Using Artificial Intelligence]

Umar Hameed 0:01
Are you ready to become awesomer? Hello everyone. My name is Umar Hameed, I’m your host on the no limit selling podcast where industry leaders share their tips, strategies and advice on how you can become better, stronger, faster. Just before we get started, I’ve got a question for you. Do you have a negative voice inside your head? We all do, right? I’m gonna help you remove that voice and under 30 days guaranteed not only remove it, but transform it. So instead of the voice that sabotages you, there’s one that propels you to much higher levels of performance and success. There’s a link in the show notes. Click on it to find out more. All right, let’s get started.

Umar Hameed 0:41
Today, I’m privileged to have Chip Conley with me. He’s an advisor to Airbnb, and also the author of Wisdom at Work: The Making of a Modern Elder by Chip Conley. Is that a picture of you on the book?

Chip Conley 0:54
There’s a philosopher, I’m not quite that old. Socrates, maybe, but I guess maybe on the back cover.

Umar Hameed 1:02
There you go. Chip. Thanks so much for coming on the program. One of the things that really intrigued me about your story was, you know, being brought into a high tech company to you know, talk about service and that human connection. Tell me how that transpired.

Chip Conley 1:17
Sure, I spent most of my career starting a company called Jawad Aviv hospitality, which is, this became the second largest boutique hotel here in the United States. I sold it at the bottom of the Great Recession, and I wasn’t sure what was next. And here was this little tech company, a startup here in San Francisco. That was disrupting the hotel industry. And they, the three founders, were all millennials, and I’m a boomer and they approached me and said, We want to democratize hospitality, could you help us with that? And so I joined them. But the journey was fascinating was I thought I was supposed to be the wise one with you know, dispensing, you know, knowledge of all this stuff I learned in the hotel business. But the truth is, home sharing, what Airbnb is doing is so different, that a lot of the knowledge I had wasn’t valuable. So I also realized at age 52, at that time, that I’d never been in a tech company before. So I didn’t understand the lingo. So I believe a modern elder is as much a an intern as they are a mentor, because I had to learn a lot of things when I came here. And I really believe strongly that the five generations in the workplace, intergenerational collaboration, and so learning from each other is all about the future.

Umar Hameed 2:35
So it sounds like that movie with Anne Hathaway, the intern, and you have to be Robert De Niro.

Chip Conley 2:43
So the difference between the Robert De Niro and Hathaway movies, Robert De Niro, came in as Anne Hathaway’s intern at age 70. I came in as Brian Chesky, the CEO, who was 21 years younger than me, I came in as his mentor. But Robert De Niro became the mentor to her and I became the intern to Brian, because I realized I needed to learn the tech industry. So I think we’re all mentors and interns,

Umar Hameed 3:13
if we’re doing it right, absolutely. So tell me about your book, what made you write it? And what are the key takeaways.

Chip Conley 3:20
So the the thing that was hard for me in my first six months that at Airbnb was feeling like I was older, so I’m supposed to know it all. And, and then being surrounded by a bunch of brilliant no at all is when it comes to technology. So I needed to evolve my sense of self, my sense of identity, I was no longer the CEO of the company running a company, and I needed to actually be become a learner. So as I started to realize that this is an alternative way of being in my 50s, I started to feel more and more comfortable that I could be both the student and the sage at the same time. And that allowed me to ask a lot of very catalytically curious questions. Most people in an exec executive rank in a company ask how and why, how and what questions which are optimisation questions. And I was asking a lot of why and what if questions, because I actually had such a naive, almost beginner’s mind approach to this, that it allowed me to ask, sometimes quite dumb questions. But some of those dumb questions actually pointed out some of our blind spots as a company. So I guess, being catalytically curious, means sometimes your questions aren’t just about, you know, learning an answer, but it’s actually posing almost an existential question to the organization.

Chip Conley 4:48
So chip, let me ask you like one of those moments like what was the moment where you realize I’m not in Kansas anymore, I may not have the goods to be like was one of those defining moments for you?

Chip Conley 5:00
Yeah, it was my third day on the job. And I decided I wanted to sit in a meeting of engineers, since I’d never worked in a tech company. And so I’m sitting in the meeting for you. What’s that?

Umar Hameed 5:12
I said, you find you, you went into an engineering meeting,

Chip Conley 5:15
I did get a resume. And they were all half my age and thereby doesn’t have them. And the guy running the meeting was 25 years old, turned to me at one point, not even really necessarily knowing who I was. And he asked me a question. He said, If you shipped a feature, and no one used it, did it really ship. And of course, that’s like, the, you know, the tree in the forest. If it fell, did did it really no one hurt, it didn’t really fall. I took philosophy in college, but did not take any comp, sigh. So I didn’t know what the hell he was talking about. Because I’d never I didn’t know the lingo of what it meant to ship a feature. And so I just, I looked at him, and I said, I have no idea what you’re talking about. And I just sort of, like slid down my seat, and realized, Oh, my God, I’m just going to be the idiot at this place. So I, what, what I what got, I got comfort in and I talked spend some time talking to Brian, the CEO about I said, You know, I feel like I’m not supposed to be here. And he said, Listen, you have a lot to offer. The key is just mentor privately and intern publicly. And that’s what I did is I interned brilliant, yeah, asked a lot of questions. And I didn’t mind the fact that I might be the dumbest person in the room, because occasionally my questions really pointed something out, that was quite important for us to understand. And then when I had to mentor someone, I did all of it privately. Because the last thing you want is someone the age of your father or mother, you know, telling you in the middle of a meeting that you did something wrong. So that was really very valuable to me.

Umar Hameed 6:54
So the question I have for you is this is that, when was the turning point where people in the organization really saw the value of what you do? When was the turning point in the organization, when people woman’s a turning point in the organization for you, when people started realizing, hey, chips, adding a ton of value to us? Like before, it was like unclear, but this thing really helped us improve what we do.

Chip Conley 7:20
I think the point was, when I started asking questions around the review system, I mean, first of all, I you know, I gave some talks, and we had at that point, 300 people in the company, not no one of them had any hospitality or travel background. And of course, we were in the travel industry. So I there was no doubt from the start people appreciated the fact that I could teach them something. But I think when it when people started to see the value of me, from a technological perspective, is when I started asking some interesting questions about why and what if we did think things differently with our review system? What I felt really deeply down to my toes is that the review system was our cleansing mechanism for getting better at what we do. And right. But so and the truth is, it has been that and it’s part of the reason why we our hosts have gotten better at what they do over time. And guest satisfaction continues to get better as well. And so when I was asking these questions about how we did our review system, because no hotels had ever done it the way that Airbnb was doing, it, exposed a bunch of things that we could do to improve the system. And people say, yes, we’ve been talking about that for a long time. But nobody really had sort of put it all in the way you’ve described it. And we were bored with that. And it had a huge impact. So I think from that point forward, people said, Let chip ask those occasional naive questions, and sometimes some of them are going to actually be a homerun.

Umar Hameed 8:50
What’s amazing, and this is that old adage that, you know, a smart guy knows the answer is the wise guy knows the right questions to ask. There’s a great and sometimes being that new kid on the block, you ask those amazing questions that no one else would have bothered to ask they get great results

Chip Conley 9:04
There another beautiful thing, knowledge speaks and wisdom listens. And, you know, recently I was in Utah at the Summit Series event, they’re at their powder mountain and I was they had a dead an owl than an eagle owl, you know, up there on the mountain that they were just showing,

Umar Hameed 9:23
Right.

Chip Conley 9:23
and asked the guy who actually knew owls is a wire owl is considered wise. And he says of all of the animals in the forest. They’re the best listeners. So if you really want to understand what does it mean to be wise, it’s about listening, as opposed to, or it’s about having great questions, as opposed to just having all the answers.

Umar Hameed 9:47
You know, what’samazing is that in our culture here, also wise, and on the Asian continent, Pakistan, India, that’s a derogatory thing to call someone because they’re an idiot. So it’s like, same bird. two interpretation,

Chip Conley 10:01
Wow, interesting!

Umar Hameed 10:02
So in your book, I was looking at the four lessons and the first one was evolve. Tell me about that.

Chip Conley 10:08
Well, I think, you know, if you’re in midlife and eight let’s first of all define midlife, midlife used to be considered 45 to 65. And today, I would consider it 35 to 75. Because technology means that there are a handful of people in their mid 30s are starting to feel old, about that time, and I say goes till 75. Because if we’re all going to live longer, a lot of people are going to work into their 70s. So the question that comes up, as someone says, I really want to be relevant again, is the first thing that you need to do is to historically edit, edit, or evolve your existing debt identity. For me, I was the CEO of a company, but I was joining Airbnb to be the mentor for Brian the CEO. But also I was reporting to him. So it’s a whole different habitat for me to understand. And so if I was clinging to my knowledge of the past, or my title of the past, or of just my sense of identity, it wouldn’t have worked nearly as well. So I think the key is, you know, and there’s a great sort of Zen parable about, you can’t pour more water or tea into the cup, unless you pour something out. And so the bottom line is, you need to pour some things out. And that’s a hard thing for people to do in midlife. But it actually is somewhat liberating as well. So that was the first step to evolve.

Umar Hameed 11:35
So one of the things that, you know, I believe in, which kind of ties in a little bit, is that we actively need to make sure we’re relevant to our constituents. And it sounds like what you’re talking about evolution is not just evolving, but evolving to serve your constituents at a higher level. That’s correct.

Chip Conley 11:53
I mean, you know, if you’re, if you continue to operate the way you always have, and your constituents are changing, you’re assuming that what mattered in the past matters in the future. And that’s just generally a bad assumption. Chip, did

Umar Hameed 12:10
you ever see that movie? It was called, it was about the mermaid with Tom Hanks.

Chip Conley 12:16
Oh, my gosh, yes, Splash A long time ago.

Umar Hameed 12:19
There was this one scene that I really loved in that movie, it was when Tom Hanks and John Candy a little kids, John Candy dropped some change underneath a set of steps coming down from the upper level. So you can look up girl skirts, and he’s like an eight year old boy,

Chip Conley 12:33
Yeah.

Umar Hameed 12:34
And then you see him as an adult, and he’s in a church, he’s a 300 pound man, dropping change down on the floor, doing the same thing, when it’s quite obvious. And it was like, once I learned something, I stick with it. And I guess in this day and age, we can’t do that. It’s all about evolving and accelerating and getting,

Chip Conley 12:50
You know, there there can be some, there’s timeless wisdom that you take with you later into life. And some of that is valuable, no matter where you are, what habitat you’re in, most of that relates to emotional intelligence, but specialized, specialized knowledge, accumulated knowledge, my gosh, that that can that can, you know, become like have an expiration date on it, because it’s like spoiled milk. So the key is to figure out of what you know, and I’ve learned, what is that which is timeless? And what is that what you need to evolve out of and move on from?

Umar Hameed 13:26
Brilliant. So the second lesson is to learn, and that’s one of my highest values. So tell me about lesson number two, Learn.

Chip Conley 13:33
It’s interesting. Usually, when you think of an older person, it’s like they’re an advisor. And in fact, that’s my title. Now, I was the head of global hospitality and strategy for four years. And then I moved into a consulting role. So I could be part time as an advisor. But you’ll notice that these first two lessons are nothing about advisory, they’re actually about changing yourself. So instead of you being the one dispensing knowledge, the first one’s about evolving, the second one is saying, Listen, you got to learn there, you know, if you’re going to evolve out of your historical identity and unit then have created the space for yourself to learn something new. And you know, curiosity is the elixir of life. People who stay curious, tend to live longer. That’s both empirically known, but it’s also you see it, you see it. And so definitely idea of learning is something that really became catalytic for me, the more I wanted to learn about tech and about design and about the idea of home sharing, it allowed me to ask a lot of really important questions. And so I just say that for the person who’s trying to, to repurpose themselves, first you have to, you know, make sure your cup is empty, and then start filling it with something new. And that’s the Learn part.

Umar Hameed 14:54
Brilliant. lesson three was collaborate. So talk to me about collaboration.

Chip Conley 14:58
The thing that’s interesting is The most neglected fact in business, but especially in the tech business, is that we’re all human. And therefore, the nature of a tech company, while it’s full of brilliant engineers, and people creating technology products, it’s also full of teams full of humans. One of the qualities of someone who gets as they get older into midlife and beyond, is that you’ve created some pattern recognition around humans. And you’ve actually built some emotional intelligence. So while the first two lessons are sort of things that require you as a modern elder, to re, you know, to really work hard to sort of remake yourself, lessons three, and four, really speak to something that you actually have that’s quite valuable to all those around you. And the collaboration skills and the emotional intelligence that you can offer to those you work with, can actually help a team get better. And this is part of the reason why I suggest that having an age diverse workforce and ages, diverse teams create some invisible productivity. Because older people in a workplace help younger people get better at what they’re doing, often through better collaboration.

Umar Hameed 16:11
So can you give me an example of one of those, that you will part of?

Chip Conley 16:14
Sure. I was, I mean, one of the things that was, so sometimes I would lead a group, but sometimes I was just in a team, and I was just in a meeting, and I would not be leading a meeting. And there was one particular team I was on, I was 20 years older than anybody else in the team. And what I saw in the meetings was that everybody was one upping each other. So it was everybody was sort of being the no at all. And, and in some ways, there’s a competition. And so I pulled a couple of the key leaders of that team aside, separately, one on one with both of them. And I just said in the next meeting, here’s something I have learned in my, you know, history, is there something called appreciative inquiry. Let’s see if you could add, instead of like, trying to be the one who answers all the answers everything, why don’t you actually ask a few questions that actually help the group to have a conversation? And why don’t you look at some of the people who are actually communicating a lot. There’s a couple of introverts in the group who are really smart, but they almost never talk. So why don’t you actually have them, be the go to them and just let them know in advance that you’re going to be asking them to talk about something. So in essence, let’s create the psychological safety, which is something that Google has shown is the most important quality in any kind of team, let’s create the psychological safety for people to feel like they can contribute, especially the introverts. And what happened as a result of that is the dynamic in the meeting changed, instead of having the same two or three or four people who dominated the meeting, and we’re basically fighting each other for who is smartest, we created much more of a conversation. And it was, it was a miraculous change. So that’s, that’s an example of having some emotional intelligence and building that skill over time and then applying it in a place where these young people had never really been taught those kind of collaboration skills.

Umar Hameed 18:08
That’s brilliant. And that’s why I really like examples that really crystallize what you’re trying to communicate.

Chip Conley 18:15
Thank you.

Umar Hameed 18:16
Right now you’re advising the founders of Airbnb, what does that look like?

Chip Conley 18:22
Well, it’s broad. The funny thing is I was brought in originally because of being a hospitality executive. But I think what Brian and the founders appreciate about me is my strategic point of view and thinking more broadly about where the company should go. So sometimes it’s related to, you know, how do we roll out new businesses that we’re going to go into? Sometimes it’s related to the culture of the company, sometimes it’s related to how do we build better relationships, the Airbnb as a disrupter. There are certain people who are scared of us, or don’t like us. And so how do we actually build more diplomatic relationships with those kinds of people? So I think the best thing I can say is that to be in a position where I, you know, this company is exactly 10 years old now. And now it’s the largest hospitality company in the world. And I started here five and a half years ago, and we didn’t even consider ourselves a hospitality company. So it’s been quite an experience to see how technology leads to disruption. Innovation doesn’t lead to disruption. Innovation is you can do innovation without having technology. The technology takes an idea and makes it global overnight.

Umar Hameed 19:38
Totally brilliant. So chip, what’s your biggest hope for this book?

Chip Conley 19:42
I think my biggest hope for this book is twofold. One is to across all generations, because we have five generations in the workplace now is to create a new kind of intergenerational collaboration that we’ve never seen before. So that’s one thing and realize it’s like a potluck and we can all agree share with each other what we know best. But I think the other thing I’m looking for is to help people in midlife to repurpose themselves and to actually help organizations see the value of wisdom, wisdom being a combination of confidence and doubt with with the ability to use pattern recognition over time to actually help create great insight. And I think that, you know, that ability for people in midlife to feel like they have something still to offer is pretty important. Just because we’re all living longer,

Umar Hameed 20:35
Before we part company, you’ve been doing the book tour, you’ve been talking about it for a while, what’s the best story of someone coming up to you saying, you know, hey, this book helped me in this way.

Chip Conley 20:45
Well, the book, the books, actually not out till September 18. So I know when it’s been more my articles that people have said that about so far. But I have been on the book tour just talking about it in advance of the book. I think the number one thing I’ve heard because I we created a modern elder Academy down in Mexico, three acres on the beach, where people come and learn how to repurpose themselves. What I’ve learned from that experience, and from the articles is that people think somehow at age 45, or 50, they’re on the decline. And there’s no, they don’t have any ingenuity left, or anything to offer. And yet, if you’re going to live till age 100, and a lot of us will, if you do the math at age 50, if you start counting at age 18 is your adult life when you start having more choice, you’re only 32 years of the way through your adult life. And you still have 50 years of adult life left. So I think what I’ve really seen is people the stories I’ve seen of people in their 50s and their 60s, and sometimes even in their 70s to actually re imagine how they can be relevant, whether it’s taking coaching and counseling skills and making that into a career, or whether it’s frankly becoming an entrepreneur in their 60s, there’s a beautiful TED talk by a guy named Paul Tanner, who at age 66 started his own company, and it became very successful. So I think it’s just it gives you some hope that yes, our physical peak is in our 20s. And maybe our salary peak in many cultures is in our mid 40s, early 50s. But our human peak or emotional peak or our peak at when we can actually be most valuable to other people could be our 60s or 70s even after that.

Umar Hameed 22:29
Brilliant chip. Thanks so much for sitting down with me. I really enjoyed the conversation I did tomorrow. Thank you.

Umar Hameed 22:41
If you enjoyed this episode, please go to iTunes and leave a five-star rating. And if you’re looking for more tools, go to my website at nolimitsselling.com. I’ve got a free mind training course there, that’s going to teach you some insights from the world of neuro-linguistic programming and that is the fastest way to get better results.

About the Author Umar Hameed

I am a performance coach who uses Applied Neuroscience to help individuals and teams break through their barriers so they become awesomer! Take a look at my Motivational Speaker Kit

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