The Learning Leader Show With Ryan Hawk - 273: Chip Conley - How To Be Wise Beyond Your Years

Starting point is 00:00:00 But I didn't optimize in terms of in from a financial perspective and it was primarily because I optimized from a personal perspective. I said you know I need to get out of this. Yeah when you are a leader and I love the fact that that's really the the the subject we're talking about when you're a leader you are the emotional thermostat of those you lead and so how you set your own setting on the climate of the room in terms of your own it influences so many people and And having gone through the dot-com bust as the largest hotel you were in the Bay Area, and I was early in the 2000s, and then just four or five years later, going through the Great Recession, I could see that I was a gladiator the first time as a leader,

Starting point is 00:00:42 and I helped up the game of everybody. But I felt a bit like a prisoner during the Great Recession, and so I realized that, frankly, I wasn't the best leader for this company anymore that I'd started. This episode is brought to by Gusto. Gusto is making payroll benefits and HR easy for small businesses. Modern technology does the heavy lifting, so it's easy to get things right. PCMag and fit small business have called Gusto the best payroll for small businesses. Gusto saves you time.

Starting point is 00:01:14 72% of customers spend less than five minutes to run payroll. Don't believe it, just Google them. People love Gusto. How often do you actually love your payroll provider? Most small businesses don't have an HR expert, but you don't need one to use Gusto with great software and great service. You can focus on your business, not payroll and paperwork. And to help support the Learning Leader Show, Gusto is offering our listeners an exclusive limited time deal. Sign up today and you'll get three months free once you run your first payroll.

Starting point is 00:01:49 Just go to gusto.com slash leader. That's G-U-S-T-O-com slash leader. Welcome to the Learning Leaders Show. I am Ryan Hawk. Thanks so much for being here. It is Mindful Monday. Text learners to 44222 in order to join thousands of other fellow learning leaders from all over the world. Text learners to 44222.

Starting point is 00:02:19 Now, on to tonight's featured leader. It's with Rebel Hospitality Entrepreneur and New York Times bestselling author Chip Conley. He's disrupted his favorite industry twice. At age 26, he first. founded Joie de Vieve hospitality, transforming an inner-city motel into the second largest boutique hotel brand in America. He sold it after running it as CEO for 24 years, and soon the young founders of Airbnb asked him to help transform their promising startup into the world's leading hospitality brand. Chip served as Airbnb's head of global hospitality and strategy

Starting point is 00:02:54 for four years, and today acts as the company's strategic advisor for hospitality and leadership. His most recent book is titled, Wisdom at Work, the Making of a Modern Elder, a few of the topics we got into. The number one quality that defines wisdom in the workplace. And then Chip tells the cool story of starting a mastermind group with his best friend, Seth Godin, when they were both first year students, MBA students at Stanford. And then what it means to be catalyptically curious. I love that phrase and how to create this mindset at your place of work. There is so much wisdom in this conversation. I loved it.

Starting point is 00:03:36 Ladies and gentlemen, it's Chip Conley. All right, Chip Conley, thank you so much for joining me here on The Learning Leader Show. Ryan, it's a pleasure and an honor. I've been an admirer of your work from afar. Your books and certainly your story, which we're going to get into, is fascinating. And I'm really curious for you to tell it for my. listeners who have not heard it yet, but I do have a question to get us going. I am fascinated by leaders who sustain excellence over an extended period of time, specifically understanding why.

Starting point is 00:04:15 And you have spent a great part of your life, both sustaining excellence as a leader yourself, as well as around others who have done the same. I'm curious from your perspective, what are the commonalities among leaders who sustain excellence? Well, it's a great question. And I would say that the number one factor that I've seen both in myself and others is that they have an operating system, an OS, that's quite unique that defines how they operate no matter what the context is. And let me explain that without being abstract.

Starting point is 00:04:55 Act. So I learned about 20 years ago, 15 to 20 years ago, about how to apply a psychology theory, Maslow's hierarchy of needs to organizations. I wrote a book about it called Peek, How Great Companies Get Their Mojo from Maslow. Long story short, is that process of coming up with a unique operating system that worked for me around leadership. In this case, it was creating a hierarchy of needs for employees and customers and investors, allowed me to, in essence, no matter what context I'm in, have a way of thinking about people, what's their hierarchy of needs, how can I serve them at the base of the pyramid, their survival needs, their success needs, and their transformation information needs. Now, I am both a practitioner as a CEO and a senior leader in companies,

Starting point is 00:05:53 but I'm also an author. A lot of people aren't that, so they may not have their own operating system. But what they may have instead is an absolutely finely tuned sense of what their greatest strengths are and how they leverage those strengths and support themselves with their weaknesses or areas that are not as strong with people in positions that help to address those issues. So I say at the end of the day, it's really about self-awareness. Self-awareness. One of the things that you wrote in your book, Wisdom at Work, which is fantastic. I'm really appreciative of your team sending me an early copy that I've, in my experience

Starting point is 00:06:33 that I've found from senior leaders that they do this really well. And I'll quote your book. One quality that defines wisdom in the workplace is, quote, the capacity for holistic or systems thinking that allows one to get to the gist of something by synthesizing a wide variety of information quickly. I'd love for you to expand on that aspect of being defining wisdom in the workplace. Yeah, you know, it's interesting. That was true in the context of the fact that the book is about how people get older

Starting point is 00:07:06 and maybe they get better. And in some ways, the way the working world, especially, here in Silicon Valley can be is frankly after the age of 35 you start feeling old. And there are certain parts of your brain that actually do start getting a little bit more problematic. Your quick recall, your memory. Those are some things that actually as you get older, get worse. But one of the areas where your brain gets better over time is what they call four-wheel drive or all-wheel drive thinking, which means that you can actually synthesize left and right brain more quickly and more effectively, such that it allows you to

Starting point is 00:07:47 look at something and get the gist of it or see the pattern recognition in it. And I think pattern recognition is a great way of defining wisdom. And so the longer you are on the planet, up to a point at about age 65 or 70, your mind actually gets better at being able to systemically or holistically see something rather than get too caught up in the trees. So you see the forest. And that kind of thinking is to me why the Airbnb young Airbnb founders asked me almost twice their age to come in five and a half years ago to help look at the system of a global company growing that quickly and on its path to trying to become a hospitality company and a hospitality brand.

Starting point is 00:08:36 So I want to get to the Airbnb story in a second, but I also want to circle back to the gist of your first answer in response to sustaining excellence. Essentially, it's people who have high levels of self-awareness have the greatest chance to sustain excellence over time and certainly agree. I'm curious for those who have a growth-oriented mindset, how does one develop self-overage?

Starting point is 00:09:03 awareness. It's a great question. There are many ways to do it. And so let's be careful of me prescribing it and saying this is the only path. I think self-awareness is a combination of understanding yourself and being able to have internal antenna. So I think we all have internal and external antenna. Some of us are better at one as opposed to the other. If you're better at external antenna, you're really good at reading people. You're really good at reading a room. You're exceptionally good at being maybe a mediator and somebody who can understand and sympathize with others. It's a great quality. But what we're really talking about here is the internal antenna.

Starting point is 00:09:45 The internal antenna means you understand your intuition, your ability to even tap into your intuition. You know how you're feeling. You can even articulate the emotions that you're feeling at any moment in a way that is relatively precise. You're not just saying, I feel okay. Well, okay is fine. The problem is there's a lack of precision there. And I actually think being able to understand moment to moment of what's happening for you allows you to tap into some of those instincts, that intuition, the intuition in many cases

Starting point is 00:10:23 is tapping into some level of your gut brain. We have a brain in our head. We also have a brain in our gut. And that gut instinct and wisdom is where a lot of, is where a lot of, that sort of wisdom comes from. So being able to be self-aware is a combination of understanding yourself and then being vulnerable enough to get feedback from others about how you come across. And so I think that the combination of being able to read yourself as well as to understand

Starting point is 00:10:55 how other people see you and what's the best way for you to articulate yourself in such a way that people, it lands with people. I think those are some of the qualities of self-awareness. And I think some of the practices you can do to get better at it is journaling, meditating, going to counseling therapy, or be in some kind of environment where you have the ability to process emotions and converse in a vulnerable way with others. For some people, that might be YPO or EO or, you know, Vistage or some kind of peer forum that is, not purely based upon the transactional nature of their business, but more focused on the personal leadership side of what they're doing on a day-to-day basis.

Starting point is 00:11:42 It's interesting you bring that up. Part of my work is I have what we call a learning leader circle, essentially a paid mastermind group that I facilitate and run. And there's an application process for people to be a part of it. And I've learned as the facilitator, I know we're going to talk about this, especially with the work that you've done with an Airbnb. I've learned as much from facilitating and leading that circle, leading that group far more than I ever expected. I expected to facilitate, to bring up topics, to create dialogue.

Starting point is 00:12:17 What I was pleasantly surprised that has happened, and I'm sure they're all listening now. I love them all very much. We've become friends is the fact that the group, each as individuals, as they're out seeking their own knowledge, in their own wisdom, they have so much to bring to the table. And especially if you get the right people of givers who want to share and help others, it really can have a multiplying effect when you get a quality group of people together. It's one of the most gratifying things I get to be a part of now and we meet every other week. And I think that's a really underrated aspect of anyone developing awareness,

Starting point is 00:12:54 is to find a way, whatever tribe that is for you, find a way to be a part of, to be a part of a group where people are willing to be honest, people are givers, people are trying to help lift others up, it really can have a multiplying effect on your life. Yeah. So we're aligned on this. I was in YPO for many years and I've worked a lot with other groups as well. And I think it's especially for men. I think this is true for everybody, but I think it's particularly an acute need for men in

Starting point is 00:13:25 the sense that women are socialized, girls are socialized in an early age to share their feelings and to connect with other girls and then women in a way where you have sort of an emotional what I call emotional insurance. As we go closer to midlife and people get to midlife, it gets to be a mash up of emotions and quite often people's 40s, it can be their most difficult decade. Women have the support safety net of relationships they've built often with other women over the course of that time, whereas men are not as good at this. We're not taught this as boys, and we don't necessarily elevate our game of vulnerability and candor with our best friends. And so guys sometimes end up in their 40s, you know, frankly full of quiet desperation, as Henry David Thoreau said

Starting point is 00:14:19 long ago. So I think these kinds of peer forums are particularly valuable for men because of the fact that it gives the support space for for for for men to actually start becoming a little more self-aware absolutely so chip i don't always get into the story of uh the featured leader my guest here uh which is the role that you're playing today however i think your story is too good to not tell uh starting at the age of 26 I'd love for you to share founding your business and really how the career arc of yourself that you created as you were building your business. And then we'll get to the second part of it as well. Okay. So I went to Stanford undergrad and was lucky enough to be accepted straight into business school.

Starting point is 00:15:15 So Joe went into Stanford Business School at age 21. This is a long time ago. This is in 1982. And Seth Godin was my best friend, and we were the two youngest guys in our youngest people in our business school class. I focused on real estate. I got my real estate license at age 19, worked for my uncle's real estate development and brokerage company. And that's what I focused on in business school. And then for the first few years out of business school.

Starting point is 00:15:41 But it was at age 26. I said, you know what? I want to do something a little bit more creative with my real estate background. and the boutique hotel movement in the United States was just getting off the ground. This was 1986, 1987. I, at that age, quit my job, started a boutique hotel company called Jua de V, which is a very impractical name for a company, but it means joy of life in French. And I love the fact that our mission, creating joy for our employees and our customers,

Starting point is 00:16:11 was also the name of the company. I bought a motel in the tenderloin of San Francisco, a really tough neighborhood. It was a pay-by-the-hour motel and turned it into a place called the Phoenix, which for almost 32 years now has been sort of the rock and roll hotel of San Francisco. And over the course of the next 24 years as CEO and founder of that company, we created 52 boutique hotels. We became the second largest boutique hotel year in the U.S., but almost exclusively in California. And I ended up selling the company in 2010 and still own a bunch of hotel real estate. but had grown the company from one person to 3,500 people, and I was done with it. To be honest, that's a whole other subject.

Starting point is 00:16:56 But I'd really got into a place where, you know, we can have one of three relationships with our work. It's either a job or a career or a calling. And for 22 of the 24 years, maybe 21 of the 24 years I was doing that, it was a calling. And one day, it's like the on-off switch just happened. And I had some self-awareness, to use the phrase we talked about earlier. to see it coming, but it came so quickly that I realized this calling had devolved into a job. And when that happens, and you've been totally in the trenches on it and working 60 or 70 hours a week,

Starting point is 00:17:35 and all of a sudden it feels like you're in handcuffs because it's so dominant in your life, but you don't love it like you used to. It's a really challenging place. And so I was lucky enough to sell the company at the bottom of the, the great recession and move on. Did the, I don't, I haven't seen any of the numbers disclosed. So maybe that's for a reason. Did, did, did you make enough money to not ever have to do anything again at that time?

Starting point is 00:18:01 Yeah. I mean, I did, I did well enough. The combination of the fact I didn't sell any of my real estate and that's where, frankly, the greatest value was at net worth meant that I didn't have to, I didn't have to work either. I sold the company probably for one third of what I could have sold it for, maybe four years later, five years later in a more robust economy. But, you know, I sold it enough for, yes, I didn't, necessarily have to work again, that's for sure. But I didn't optimize in terms of, from a financial perspective. And it was primarily because I optimized from a personal perspective. I said, you know,

Starting point is 00:18:35 I need to get out of this. When you are a leader, and I love the fact that that's really the subject we're talking about, when you're a leader, you are the emotional thermostat of those you lead. And so how you set your own setting on the climate of the room in terms of your own, it influences so many people. And having gone through the dot-com bust as the largest hotel you're in the Bay Area, and that was early in the 2000s. And then just four or five years later, going through the Great Recession, I could see that I was a gladiator the first time as a leader, and I helped up the game of everybody. But I felt a bit like a prisoner during the Great Recession. And so I realized that, frankly, I wasn't the best leader for this company anymore that I'd started.

Starting point is 00:19:20 Wow. That I think having that awareness, especially after having immense success for many years, a couple decades, has to be quite rare. Yeah. Well, here's the thing. It's part of what I've been talking about in the new book, Wisdom at Work, and it's part of what I'm doing with people at this modern elder academy. We've created on a beachfront in Mexico. People get very attached to their identity. They don't realize how attached, how affixed this name tag is to your chest that says you are the founder and CEO of X company.

Starting point is 00:20:00 Or you are the chairman of the board of this nonprofit board. Or you are the father of these twins. we have a lot of identities in our lives, and some of them actually are so attached to us that instead of being like a name tag, you can take off, they are stuck to you. And for me, founder and CEO of a company that became very successful and was in many ways

Starting point is 00:20:27 a role model for corporate culture and leadership, and I'd written books about it, and all of a sudden I realized I can't do this anymore, and having to strip that identity away is not easy at all. And it deserves a book unto itself because the process of realizing your identity needs to shift is one of the transition points that I think people in midlife struggle with because they get so used to that identity. And that's when midlife crisis happens. So before I, as I was doing my deep dive, there's a blog post from some. September 9th, 2007, I assume you've read this, called Random Acts of Initiative,

Starting point is 00:21:17 the author of this blog post, none other than your friend, Seth Godin. And he said, as a young first year student at the Stanford MBA program, Seth writes, most of the other 300 students had wasted a few years working at a bank. But Chip Conley picked out four other, meaning you said you came straight from undergrad, And you picked out four other student strangers to him and to each other and invited them to a weekly brainstorming session. You explained to us that once a week we'd meet for four hours and brainstorm business plans. Entrepreneurial Ventures a year later, we had compiled more than 500 great ideas. And I think Seth talks about the extraordinary thing about you is this initiative, setting up the group is how rare it is.

Starting point is 00:22:02 And successful people have this in common. It's not a giant breakthrough. It's the willingness to take little chances. Wow. Well, yeah, I hadn't heard it. I hadn't read that or heard it for 10 or 11 years. So, yeah, I think we have hunches. You know, again, that those internal antenna give you ability to not just have intuition, but hunches.

Starting point is 00:22:29 A hunch is an element of a guess, but there's something in it that feels like it's more than guess. And I guess for me, I have these hunches all the time. And quite often I don't have the chance to act on them. But when you create some space in your life and when I sold my company, I created some space. It gave me the ability to actually listen to the hunches a little bit more and then start taking some actions. And in the case that Seth's talking about, my hunch in business school was I felt a bit like an aberration there. I was, I was, was 21 years old. And so there were a bunch of other people who were similarly young.

Starting point is 00:23:12 I think there are only two of us who came straight from undergrad. And I think both Seth and me. But we ended up having five of us, all men, unfortunately. It would have been nice to have a woman or two in the group. But we basically had five youngest people in the class. You know, I said, let's meet on a regular basis. Because we in some ways were, there are a lot of people in our class who sort of looked at us as the idiots. because we were so young.

Starting point is 00:23:38 And so by actually putting ourselves together, it gave us a sense of solidarity. It just seems so ahead of your time. So the next part of the story, you sell your business, you have enough money where you don't have to do anything, go surfing or do whatever you want. And instead, you, I think it was a phone call, get a phone call from someone who's,

Starting point is 00:24:03 I'd say, pretty famous right now asking for your help. Yeah, so to be quite honest, I was as a hotelier, I had the opportunity twice to sort of disrupt my favorite industry, the hospitality industry, once I did it as one of the first boutique hotel years in the U.S. And then more recently, five and a half years ago, was when Brian Chesky, co-founder and CEO of Airbnb, called me and said he wanted to get together and understand my perspective on hospitality innovation. And to be honest with you, in early 2013, I didn't have an Uber or Lyft app on my phone. I'd never used Airbnb. I thought Airbnb was a subsidiary of couch surfing. I really didn't understand the model. So it was funny how I was the pioneer long ago as a 26-year-old creating boutique hotels, you know, competing with the Marriots and Hilton's of the world.

Starting point is 00:24:57 And then, you know, all of a sudden, I'm at age 52 when he called me. I'm the establishment. And so I didn't understand the Airbnb or home sharing phenomena. But when I met with Brian, what I saw quickly is something you and I talked about, which is the growth mindset. Carol Dweck's work from Stanford, the idea that Brian had an extreme growth mindset, meaning he was instead of focusing on trying to prove himself, which is often the fixed mindset, he was focused on trying to improve himself.

Starting point is 00:25:29 And what's so true of leaders is leaders quite often rub off on the company, meaning there's an element of the company is the personality of the leader writ large. And so what I was imagining is that this company was a growth mindset company. And so even though I didn't understand much about it five and a half years ago, I said to Brian, I'll be your mentor and I will help you take your little tech company and turn it in a little. into a hospitality global brand. And as it turns out, I was his mentor, but I became, frankly, he became my mentor as well. We had a bit of what I call an EQ for DQ relationship. I provided him a little bit of EQ, emotional intelligence, which is something you build up

Starting point is 00:26:16 over the years. And he taught me a lot of DQ, digital intelligence. And I actually think that's one of the implicit trade agreements we can have across generations in the workplace. But I, yes, I was there for four years as the head of global. global hospitality and strategy oversaw seven or eight different departments in the company. And then a year and a half ago moved to just being a strategic advisory to the founders, primarily because it just didn't want to work so hard because it was definitely going back into the,

Starting point is 00:26:46 you know, rocket ship moment of 60 and 70 hour a week, weeks. Because what a phenomenal company. You know, so that's what I learned. There's a lot more to unpack there, I'm sure. though. I'll let you ask another question. One of the phrases that you've used that I really like is, I think, a reason for your success and what you had to be there because you were, I think you called a mentor, which is at once both a mentor and an intern, and you reference the Robert De Niro movie, which is actually

Starting point is 00:27:22 really good. When they called the intern, where he went as a more experienced older, guy to intern for Anne Hathaway's company in that movie. And I found that phrase, mentor, to be interesting. Explain how that was the role that you played at Airbnb. Yeah. So it's funny, the Robert De Niro juxtaposition is a really good one. He joined Anne Hathaway at her company as her intern.

Starting point is 00:27:55 I joined Brian Chesky as his mentor. So it was the exact opposite. But over time, what happened with Robert De Niro is he went from being the intern to the mentor to her. And I went from being the mentor to the intern. And I guess that means I went backwards. Actually, what happened was this is the second day at work, I decided I wanted to go spend a lot of time in the engineering and technical fields. I had zero background in technology. I was a 52-year-old guy in a tech company for the first time.

Starting point is 00:28:27 I had no knowledge of the lingo. I didn't know what it meant to ship product. And so as I started spending more time there, I realized that there was a whole collection of things I didn't know. And so I thought I was supposed to be there to be the know-it-all, the mentor. And of course, my approach to, you know, hopefully is not a know-at-all attitude. But what I realized quickly is I needed to evolve my identity and become an absolute, like, you know, a voracious appetite learner.

Starting point is 00:28:59 And so I became the beginner's mind in the company. And what that meant is quite often people knew if you're sitting in a room with Chip in a meeting, Chip will likely ask a lot of why and what if questions, whereas most senior leaders are more focused on the optimization questions of how or what. And so why and what if questions are like what four-year-olds asked? And so at times I sounded a bit like a naive four-year-old. But what was interesting is that sometimes when you ask these bigger questions, you help to point out blind spots that the company hadn't seen.

Starting point is 00:29:37 Because if you're constantly in the optimization mode of what and how do we do it better, as opposed to why are we doing this? Or what if we tried that? those kinds of bigger questions led to a lot of catalyically curious thinking in the company that I believe helped us quite a bit at a time in early 2013 when we had a lot of growth, but our market for who we were serving was almost exclusively budget-oriented urban millennials as our customer. And we had not necessarily bridged the gap to all of the other demographic groups

Starting point is 00:30:14 or other kinds of ways we can become the largest global hospitality brand today. I love that phrase catalytically curious. Did you guys come up with that? I haven't heard that before. I came up with that. Someone called me that. Well, I guess I didn't come up with it. Someone came up with it and labeled me that.

Starting point is 00:30:31 So someone called me, Chip, you are the modern elder at Airbnb. And I said, what is that? I said, elder, oh, my God. And it was true. Of course, I was 52 at that time. I'm 57 now. And the average age when I first started was 26 there, so I was twice the age. So I was clearly an elder in that world.

Starting point is 00:30:50 But the word elder sounded terrible because it sounded like elderly. And over time, I started to embrace it and realized that elder is very different than elderly. And the modern elder is someone who is as much a student as they are a sage. And so in the context of being a student, I was catalytically curious, which meant that my curiosity and my questions helped catalyze other people. to be inquisitive as well. And that's a really important quality, especially in an environment that's full of young people, really smart young people who are all-know-it-alls

Starting point is 00:31:23 and who, frankly, sometimes in meetings, like to show how much they know. And I got to a place where I was showing how much I didn't know. But weirdly, the process of asking good questions, it's like any kind of, you know, almost like Socrates back in Greece. it was the idea that a great question leads you into a direction of like, wow, what are our options? It creates more options for people.

Starting point is 00:31:51 And so I think it was very successful in the company and I think led to the company being just a little bit more curious, you know, as an organization. It's so contagious. It is. You know, it's really important, again, knowing that as a leader, your actions are going to be emulated and the higher you are in an organization, the more. of catalyst for that emulation. And so for me, I was lucky enough. I had over 100 people in the company asked me to start mentoring them

Starting point is 00:32:21 because what they wanted was more of what they saw from me. And it doesn't mean I was like walking on water or anything like that. I wasn't. But what they could see was that Chip was somebody who interned publicly and mentored privately. And what that means is when I was sitting in a meeting and Brian or something,

Starting point is 00:32:40 somebody else would say something or they would exhibit a behavior that I thought was actually counterproductive for them. Instead of bringing them up in the meeting, which of course, no one wants their father, like speaking in the meeting and saying, you know, Brian, that was a stupid comment or you were dismissive to so-and-so. So my mentoring of people tended to be something I did privately. And what it did is it created a nice trust that people felt like I was there to support them, but not to make them look bad.

Starting point is 00:33:09 But similarly, I interned publicly, meaning that people knew that I was very open to being the dumbest person in the room and asking some really, at times felt like very rudimentary questions. But sometimes those questions were so fundamental to the fact that we had just made a bunch of assumptions that got us to where we were, that we hadn't peeled certain things back to say, why don't we do it this other way instead? Or have we thought about doing that? And so, yeah, I mean, it's important, you know, with it. Yeah, go ahead. Well, I was just going to say the willingness to have that approach I found in my experience only comes from people who have a deep level of security in oneself. And unfortunately, a lot of times we see the opposite, the insecure leader who has all

Starting point is 00:34:03 the answers. And I would say, mentor. publicly and mentoring would be a nice way of phrasing it as you've probably seen before. And yet you have done the opposite. And so I think is it, did you have, did it take time to build up such belief and security in yourself? And maybe your success along the way for decades has helped develop that or how, the reason I ask this chip is because I'm thinking of the 34 year old mid-level manager in a multi-

Starting point is 00:34:38 billion dollar company. This is, I'm describing myself at one point in my life, who wants to be the Chip Conley of their meeting room when they're meeting with the CEO or they're meeting with other peers, other leaders in the business. How can somebody take what you're teaching now and implement that into your game? Because I feel like the execution and implementation is so important. I want people to learn from this show. I want them to take great notes and learn. But I also, and more importantly, I want them to execute on what they're learning and be able to implement it into their day-to-day lives so they can get better. And I'm curious for that person listening, that specific person, how what you have done,

Starting point is 00:35:20 what you would say to them. It's all about ego, to be honest with you. I think that younger in life, we have a lot of hubris. We have a lot of confidence that we want to actually show the confidence because we feel like if we show the confidence, people will respect us as leaders. And yet I think that hubris turns into humility as you get a little older because you see no one's perfect, including yourself, and there's all kinds of things you don't know. So the process of accelerating you from the hubris to the humility and moving from trying to

Starting point is 00:36:00 prove yourself to trying to improve yourself, again, fixed to growth mindset, those kinds of steps will accelerate yourself so that you could be a 34-year-old, wise old soul in a young man or young woman's body that those kinds of people I like to surround myself with. And I think that, you know, wisdom, there's a sense that wisdom is something you get when you get older, but not really. I mean, And if you don't cultivate it and harvest it properly, just because you're older doesn't mean you're wiser. You know, older and elder are two different words. An elder is something you have to cultivate. And I actually think you can be an elder, frankly, just five years older than the people around you.

Starting point is 00:36:47 But I think what is so essential around all of this is to move out of the ego and out of the sense of trying to prove yourself into the place of how are you, how are you, how are you? you creating the best organization possible beyond your own selfish needs? And I assume that all of this wisdom you had in your mind was the reason behind writing wisdom at work, the making of a modern elder. Is that accurate? Or what was the point that you said, you know what, I need to document this so that I can help others? Well, this is my fifth book. So I've, I agree. I, I agree. When I was 12 years old, I said to my parents, I want to be a writer when I grow up. My parents, my dad said to me, but writers are poor or psychotic and most are both. And so I didn't know what psychotic meant at age 12, but it didn't sound very good.

Starting point is 00:37:41 So I went out and I became an entrepreneur. But lo and behold, in my late 30s, I started writing my first book called The Rebel Rules, Daring to Be yourself in Business. And Richard Branson wrote the Forward. And I have now with my fifth book, Wisdom at Work, I have done. just continued in the course of my career to feel like the best way for me to make sense of what I've learned along the way is to write about it or speak about it. And so that's what I've done. And partly because I want to share it with others, partly because I want to frankly figure it out myself. And in the case of this particular book, Wisdom at Work, The Making

Starting point is 00:38:20 I'm a Modern Elder, it was the fact that I saw this intergenerational collaboration at Airbnb, be not just between me and the three founders who are, you know, two generations younger than me, they're millennials, I'm a boomer, but it was in a variety of other places in the organization as well where there was a generational potluck happening here where boomers and Gen Xers and millennials and now, frankly, Gen Zs are actually coming together and bringing their, what they've got, you know, their best potluck dish to the table. And we have five generations in the workplace today, and yet there's a lot of age segregation. And so I think that the future for organizations is to look at how you harness that collaboration

Starting point is 00:39:07 across generations. And that's really why I decided I wanted to write the book. And I believe it's, I read that the reason that Brian originally reached out to you was because he read Peek, how great companies get their mojo from Maslow, a book that you authored, that that was the initial reason why he called you. Yeah. So a great example. Yeah.

Starting point is 00:39:30 Why you document your beliefs, right? Exactly. In this case, that came back to serve me quite well because as a thought leader around that subject. And Brian was very focused on human potential and how we live up to our self-actualization and peak experiences at the peak of Maslow's pyramid. So, yes, I, you know, that, but I'm not just. to be clear, to be a great leader does not mean you have to be a great author. To be a great

Starting point is 00:39:58 leader does not mean you have to go stand on the TED stage like I've had the honor to do. To be a great leader is to serve an organization and those that you serve. And the number one question that I think great leaders ask their people is how can I support you to do the best work of your life here at fill in the blank. The fill out the blank is whatever core organization you're in. And whether it was at Jue de Ville, my boutique hotel company that I ran for 24 years, or during the last five and a half years at Airbnb, when I've had direct reports, when I asked that question, how can I support you to do the best work of your life here at Airbnb? There are two pieces to it that I think are fundamental.

Starting point is 00:40:41 The first piece is when you know your boss has your back and your boss is interested in seeing you do the best work of your life, that level of support gives you the sense of, you, you want to actually live up to that expectation. Great. That's the first part. That's the obvious part of the question. The less obvious part, which I love even more, is when I'm asking this question,

Starting point is 00:41:05 how can I support you to do the best work of your life here at Airbnb? It's actually putting my direct report in the role of telling me how to create the conditions for them to grow as a leader and as somebody in the organization, which means they cannot be the victim. It means they cannot be the martyr or the person who's just going to complain that the company or their boss is in their way or is an impediment. So it does require you as the leader to actually listen and then take action when you can. But it absolutely puts in your direct report's responsibility and lap the obligation to ask themselves,

Starting point is 00:41:48 what are the things that are in the way of them being the most successful they could be here? And so I would just offer that to your community, Ryan, that it's a really simple question, but it's a real profound one as well. And I have found that those people who worked for me who couldn't answer it very well didn't really know how we could create the conditions for them to succeed, whether it was having them go to some workshops or conferences to learn things or it was to make sure that the quality of the IT tools they had were better or make sure that they have a meeting with me once a week for an hour to talk about, you know, what could improve. If someone can't articulate what they need in terms of conditions to do their best work, then I have some concerns about their ability to do great work. The part of that that I think was really critical is the listening aspect of it.

Starting point is 00:42:45 I've, everyone listening has probably worked for a leader who may have said something like that. But the critical difference is somebody like you, Chip, who actually then helps them take action or takes action based on what they listen and what they've heard, as opposed to doing it as a check the box exercise. And maybe I'm speaking from a negative experience personally, but I feel like that this has happened from time to time because maybe somebody reads it. But then again, the execution and the listening and the implementation of that doesn't happen.

Starting point is 00:43:17 And that's how an organization can fall apart and morale can sync as if you say it, but then you don't follow it up. So I do, I love that advice. I think it's great. I just want to stress, again, maybe from experience that that second part is equally important that you listen and you actually do it. Absolutely. Yeah, if you build an expectation, it's like, you know, work climate surveys or employee satisfaction surveys, you ask for all this feedback for your employees. They give it to you and then nothing happens. And, you know, so you've built an expectation and then, you know, my last book was called emotional equations and I have 18 different equations about different emotions. Disappointment equals expectations and minus reality. So if you build up an expectation, whether it's within your employee ranks or it's, you know, within your customers or at your investors, you build an up expectation,

Starting point is 00:44:10 and the reality doesn't live up to it, you've created a disappointment equation. One of the other parts of your role at Airbnb was, I believe, they asked you to set up a learning and development program. Is that accurate? Yep, it is. How, I get a sense then that this initial role

Starting point is 00:44:30 to essentially mentor the leaders of the business seem to turn into a lot more than just that. Because I think that alone could be more than a full-time job. Well, it was supposed to be, you know, I said to Brian, I'll give you eight hours a week. Let's do this a part-time thing. And he, we arm wrestled and he won. And so it's 15 hours a week is what I agreed to. But within about three weeks, it was 15 hours a day.

Starting point is 00:44:54 And within five weeks, I was now that head of strategy, originally just head of global hospitality. But now I was at a strategy. And then a week later, I was ahead. not just the head, but in charge of building a learning and development organization within the company. And then a few other things, head of business development, business travel, et cetera, et cetera. The key with learning and development was to realize that, gosh, we had a lot of 28-year-olds

Starting point is 00:45:18 leading 24-year-olds. You know, that was the company, if the average age was 26, do the math. That's what was going on. So you had a lot of people in leadership or management positions who'd never really gotten any training. And I'd say the biggest area that was necessary was understanding humans. It was actually how to build emotional intelligence. And whether it's helping someone to understand how to design an alliance with somebody that they're at odds with,

Starting point is 00:45:47 and the answer there is start by actually looking at where there is alignment and start to look at what beyond the personalities, look at what it is that do both parties agree what the intent is of what you're trying to do? have two different approaches, because if you can get to something that says, yes, we both have the same intent of what we're trying to get to, and we have two different approaches, at least you can start with that. If that's not the case, and often it's not the case, then let's go back to square one and say, we need to determine what our ultimate goal is here and make sure there's alignment there.

Starting point is 00:46:20 And sometimes that requires going to the person above them. If there's two people who have a boss that can actually then step in and say, you know, this is the direction we want to go, that can help solve some things too. But, you know, taking a step back, it was really more than anything, helping people learn how to build relationship skills and wisdom around people and humans. So, you know, it's that simple. One of the common emails I get is similar to that, that building alliance question. And the email goes like this.

Starting point is 00:46:56 Ryan, I am a learner. I have a growth mindset. I love development. I love improvement and getting better. However, I feel like I'm surrounded by a team and or a boss who doesn't really care about that. They kind of punch the clock, do their work, do a fine job, and then they go home, but they don't, I bring up books or I bring up things.

Starting point is 00:47:19 I'm listening to where I'm reading and they don't really care. How do I, how do I, how do I, like, what, how do I handle a situation like that where I'm excited, I'm energized, yet the people around me don't seem to be. How would you respond if somebody came to you asking that question? Well, of course, people have come to me with that, including both at Jouadaviv and at Airbnb. The first thing is to figure out, you know, we're all like plants or like flowers. The question is, how do we grow? How do we flourish in a growing environment?

Starting point is 00:47:54 and sometimes you have to actually look at the soil and the sun. And if you're in a, if you're a sunflower and you're living in a, you know, the Arctic Circle and it's tundra and there's not much soil that can actually grow anything and, you know, there's not a whole lot of sun, et cetera, then you actually have to repot yourself. You actually literally have to get out of there, whether it's going to a different division in the company or leaving the company altogether. There are times when you can start to influence what's around you. And I think I would say the most important ingredient there is to have a boss that you think

Starting point is 00:48:30 has the capacity to get there. The boss may actually not be there yet, but just because they're not there yet doesn't mean they can't be influenced or persuaded. And what I've seen happen, and this really speaks back to Peak again, Peak became a big-time popular book in a lot of companies from Tony, Tony Shea at Zappalo. and a bunch of other people, sort of ultimately, it was somebody, I think, in Zappos, who works for Tony, who read the book. Now, Tony has a growth mindset, et cetera, so it helped.

Starting point is 00:49:00 But at the time that Tony was given the book, he was so in the weeds doing his running the company that he'd lost track of some of the sort of bigger questions about creating the culture. And so in many cases, I think being a junior person to a boss and then giving them a book or giving them an article or giving them just some resources that they don't have time to go out to find themselves and helping them start move a little bit in the direction toward your point of view is possible. If that's not possible, my recommendation is either you have an insurrection and you figure out how to get a different boss there or you probably have to look for a different place to work, whether it's within the company or outside.

Starting point is 00:49:47 Chip, all the wisdom you share with me is fantastic. I really appreciate it. Is there anything I may have missed from wisdom at work that you want to make, do you want to get in here before we take off? I think, you know, the wisdom at work, making a modern elder, you can find it at my, at Chip Conley.com. And you can also find out a little bit about our modern elder academy down in Mexico as well. Talk to me more about that. What's that like? So the premise of this was, you know, as society,

Starting point is 00:50:25 and we have historically provided some level of right of passage and rituals and celebrations to help people through the periods of life that have most transitions in them. So that's like in puberty, a very transitional moment for kids, you have kinseneras and bar mitzvahs and bat mitzvatsvahs. And so you create some society in that when you get married, you have weddings, when you have a baby, you have baby showers. When you die, you have a funeral. The thing that's been interesting is because in the year 1900, longevity in the U.S. was 47 years. So midlife was 23 or 24 years old, and frankly, it wasn't too far off from when people got married or had their first child.

Starting point is 00:51:07 So there really went midlife rituals. Well, today, with, you know, the average age of longevity is about 82 in the U.S., and it'll soon enough be up to 90 in the next 20 to 30 years, there's a huge marathon that's midlife. And it used to be 45 to 65. I believe now it's 35 to 75. And yet we have a zero in the way of rituals or celebrations or ways for people to transition in ways that are healthy. And so I decided to create the world's first midlife wisdom school

Starting point is 00:51:39 called the Modern Elder Academy. I had a home down on the Baja coast, an hour north of Cabo San Lucas in Mexico, where I surf and enjoy my life. And I bought a bunch of land and homes nearby me and have created this campus. And at modernelderacademy.org, people can go and apply to be in workshops with me and a bunch of other well-known people to learn how to cultivate the second half of their life and understand their mastery, how to mind their mastery and their wisdom. and apply it in new ways, both in their existing working world and life or in transitions into new ones, new kinds of working lives. Love it, man.

Starting point is 00:52:24 It's awesome. And your story is as well. And I really appreciate the depth that you're willing to go to, to share it here on my show. So thank you so much for being here, Chip. I would highly recommend wisdom at work, the making of a modern elder, regardless of your age. This is not for people who are on the verge of retirement. I will say that when I first got it, I thought that might be what it was about, but it's not.

Starting point is 00:52:49 It's really truly for anybody who's looking to grow and prove, get better. But it's really well done. And your story's just fascinating, man. So thank you for sharing it. Thank you, Brian. Thanks for all you're doing to create more great leaders out there. Absolutely. And I'd love to continue our dialogue as we both for us, man.

Starting point is 00:53:09 Great. Perfect. All right. Thanks, Chip. Thank you. All right. What a great talk with Chip Conley. I really enjoyed it. I especially love that phrase being catalyically curious and found the story of Brian Chesky reaching out to him.

Starting point is 00:53:25 Fascinating. It's why it's a good idea to document our beliefs sometimes in the form of a book. You never know the doors it may open like it did for Chip. I hope you enjoyed this episode as much as I did. If you did, I'd love it if you would write a review. subscribe and rate the show in iTunes Apple Podcasts. That's write a review, rate the show, hopefully five stars in iTunes Apple Podcasts

Starting point is 00:53:50 that really helps spread the message to those all over the world. Thank you so much for giving me the opportunity to do what I love on a daily basis, which is have these fascinating conversations with truly interesting people like Chip. I really enjoyed it. I love this one. See you next week. Can't wait. This episode is brought to. you buy Gusto. Gusto is making payroll benefits in HR easy for small businesses. Modern technology does the heavy lifting so it's easy to get things right. PC MAG and fit small business have called

Starting point is 00:54:22 Gusto the best payroll for small businesses. Gusto saves you time. 72% of customers spend less than five minutes to run payroll. Don't believe it, just Google them. People love Gusto. How often do you actually love your payroll provider. Most small businesses don't have an HR expert, but you don't need one to use Gusto with great software and great service. You can focus on your business, not payroll and paperwork. And to help support the Learning Leader Show, Gusto is offering our listeners an exclusive limited time deal.

Starting point is 00:54:58 Sign up today and you'll get three months free once you run your first payroll. Just go to gusto.com slash leader. That's G-U-S-T-O.com slash leader.

The Learning Leader Show With Ryan Hawk - 273: Chip Conley - How To Be Wise Beyond Your Years

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.