The Rich Roll Podcast - Chip Conley: How To Become a Modern Elder, Create A Second Wave & Regenerate Your Soul

Episode Date: May 23, 2022

What if we reimagined aging not as something to fear—but rather as something aspirational? Rich's guest for this exploration is 'Modern Elder" Chip Conley. A hotelier and hospitality maverick, Chip is the founder of America’s second-largest boutique hotel company and former Strategic Advisor and Global Head of Hospitality for Airbnb, where he was instrumental in guiding the founders of this fast-growing start-up into the global hospitality brand it is today. In addition, Chip is a New York Times bestselling author and founder of Modern Elder Academy, the first midlife wisdom school dedicated to transforming aging. Today’s episode is also viewable on YouTube: bit.ly/chipconley681 More about Chip + show notes: https://bit.ly/richroll681 To celebrate the 10th anniversary of 'Finding Ultra', Rich is giving away 50 personally inscribed copies. Enter to win by signing up for his mailing list HERE. Peace + Plants, Rich

I knew I was really unhappy, and I had thought about going to the Golden Gate Bridge myself and jumping. I really was at that place of saying, I don't know how to disengage from this identity I've created. I was giving a speech in St. Louis, and after the speech, I was sitting and signing books, and I went unconscious. I guess I was out for like four or five minutes,

and they called the paramedics, thankfully, and I was unconscious. I guess I was out for like four or five minutes and they called the paramedics thankfully. And I was on the ground and next thing I knew I was coming to, I had no idea where I was or what had happened. The paramedics put me on the gurney and that was the first time I went flatlined. They had to bring out the paddles to, you know, shock me back to life. And over the next 90 minutes, I flatlined nine times in 90 minutes. And what happened for me was I had to look at my life and say, is this the life I want? I was having, I guess, a midlife crisis, but it was ultimately the thing that helped me to say, get out of jail free chip. helped me to say, get out of jail free chip. You don't have to die. And I can start rewriting the script of how I want to live my life.

The Rich Roll Podcast. Hey, everybody. welcome to the podcast. On tap today is a fantastic discussion. It's a discussion about how to reimagine aging. To view aging not as something to be feared, but instead as something aspirational. An opportunity to share all that accrued wisdom, to channel it into a second act

and leverage it to deepen and make more meaningful your connection with life, your connection with others, and of course, your connection with self. My guest for this odyssey is my new friend, Chip Conley, a hotelier and hospitality maverick. Chip founded America's second largest boutique hotel company and subsequent to selling it, served as strategic advisor and global head of hospitality for Airbnb, where he was instrumental in guiding the founders of this then small but fast-growing startup into the global hospitality behemoth it is today. In addition, Chip is an in-demand public speaker and multiple TED talker. He's a New York Times bestselling

author. He sits on the board of Burning Man, and he's the founder of something called the Modern Elder Academy, which is the first midlife wisdom school dedicated to transforming aging. This one is pure gold and it's coming right up, but first. We're brought to you today by recovery.com. I've been in recovery for a long time. It's not hyperbolic to say that I owe everything good in my life to sobriety. And it all began with treatment and experience that I owe everything good in my life to sobriety. And it all began with treatment

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We're brought to you today by recovery.com. I've been in recovery for a long time. It's not hyperbolic to say that I owe everything good in my life to sobriety. And it all began with treatment and experience that I had that quite literally saved my life. And in the many years since, I've in turn helped many suffering addicts and their loved ones find treatment. And with that, I know all too well just how confusing and how overwhelming and how challenging it can be to find the right place and the right level of care. Especially because, unfortunately, not all treatment resources adhere to ethical practices. It's a real problem, a problem I'm now happy and proud to share has been solved by the people at

recovery.com who created an online support portal designed to guide, to support, and empower you to find the ideal level of care tailored to your personal needs. They've partnered with the best global behavioral health providers to cover the full spectrum of behavioral health disorders, including substance use disorders, depression, anxiety, eating disorders, gambling addictions, and more. Navigating their site is simple. Search by insurance coverage, location, treatment type, you name it. Plus, you can read

reviews from former patients to help you decide. Whether you're a busy exec, a parent of a struggling teen, or battling addiction yourself, I feel you. I empathize with you. I really do. And they have treatment options for you. Life in recovery is wonderful, and recovery.com is your partner in starting that journey. When you or a loved one need help, go to recovery.com and take the first step towards recovery. To find the best treatment option for. So this one is obviously oriented towards those who are approaching or find themselves amidst that mid-life stage of their professional career and their personal life. But honestly, it's also really for anyone and everyone who's just looking to weave a little bit more meaning

and fulfillment into their life, into their professional life in particular. And especially it's for those who have pursued a certain career track for some time and are now in that place of contemplating new possibilities. We discuss overcoming our fear of aging. We talk about navigating midlife transitions,

what it means to be a modern elder, the critical role elder wisdom can and should play in the workplace, and how to think about receive and give mentorship. We also talk about mindset. We talk about identity, getting clear on what is essential to being fulfilled. We discuss the difference between pursuing accumulation

versus the pursuit of attunement and the re-imagination of continuing education as well as community living. Final thing before we dig in, if you're inspired by this conversation with Chip, as I suspect you will, he's hosting a few workshops in Baja in June and early July. And he just launched this new eight-week online course

entitled Designing Your Purposeful Path to Work, which starts June 4. For links to all of this, check out the show notes on the episode page at richroll.com, or you can just go directly to modernelderacademy.com. Chip is a wonderful man. He's a beautiful spirit. This conversation is gonna leave you pondering your life

a little bit more deeply and hopefully put a smile on your face along the way. So here we go. This is me and Chip Conley. Well, it's good to see you. It's been a couple of weeks since we met down in Miami. I haven't shaved since, I'm trying to cultivate my modern elder look.

Your modern elder look. My modern elder aesthetic. You're looking wise. And I can't wait to dig into all of this with you today. And I was reflecting as I was driving in, wrapping my head around, you know, how to of this with you today. And I was reflecting as I was driving in, wrapping my head around, you know, how to approach this with you. And top of mind is a conversation that I had

just a couple of days ago. We had this guy, Mike Fremont in here, who's a hundred years old. Like he turned a hundred this year. Wow. And he set like the world record for the marathon at age 90. He holds like all kinds of age group running records.

And he kind of kicked it off by saying, I'm having the best time of my life. Like I'm the happiest now that I've ever been. You know, and he's like, he's a little hard of hearing and you know, he's a hundred years old, but like to hear him say like, oh yeah, like life is really great right now is something counterintuitive,

but also like right in the sweet spot of your lane and the things that you're passionate about. What's fascinating is there's a societal narrative on aging and then there's a personal narrative. The societal narrative is if you can survive your midlife crisis around 45 or 50, on the other side of that, you have disease and decrepitude and then you die. Right.

And the reality is the personal narrative on people's aging is very different than that. And there's something called the U curve of happiness. It's gotten a lot of social science research attention. And the idea of it is once you hit around 47.2, although your mileage may vary, with each passing decade after that, you get happier and happier.

So you're happier in your 50s than your 40s, 60s than 50s, 70s than 60s. And you start to see some leveling out and a decline in happiness around the last two or three years of your life. So if you're living to 100 and maybe who knows how long he'll live, he's probably still on the stride going up.

But what's so strange is the gap between the personal narrative, which is actually people do get happier as after age 50 and the societal narrative, which is you're all downhill after about age 40. But I would suspect that that happiness quotient would calibrate to, you know, you still finding purpose and meaning

in however you're spending your time, right? Like the way we think about aging is so unhealthy. It's like this black hole. Like, you know, there's, and I know you've talked about this. There's childhood, there's adulthood. And then what? Like what happens for 40 or 50 years?

Like, we don't really talk about it. You've dubbed it elderhood, but short of housing people in these horrible, you know, sort of assisted living situations, we haven't really created any kind of modern forward thinking kind of programming around like how to get the most out of these many decades later in life.

You know, if you're gonna live till 90, which is very likely for a lot of us, my parents are 84. Neither one of them has been a huge athlete and they're on a six week vacation right now at age 84. So if you live till 90 and you're 54, which is a little bit younger than you, you're halfway through your adult life if you start counting at age 18. And we don't think about life that way. We very much underestimate how much adult life we

have ahead of us. We also overestimate how long we're going to be an invalid. And there's something called compressed morbidity in the medical field. And it means that in essence, the time of your life when you're sort of on the verge of death is a much shorter period on average than it used to be. So you've got, you know, what Mary Catherine Bateson would call is, she calls it the midlife atrium. She says that having additional life, having additional years, because longevity in the year 1900 was 47 on average. And by the year 2000, it was 77. She says, all of those additional years are not like having extra bedrooms

in the backyard of your house, like you're old longer. No, she says, it's like having a midlife atrium. And the midlife atrium means there's light and air and additional space happening in the middle of your life. So you're in midlife longer. And yet we have very little in the way of your life. So you're in midlife longer. And yet we have very little in the way of society, resources, tools, or even thinking around what midlife is supposed to be.

Yeah, but historically we were much better at this. Any kind of indigenous culture has a reverence and a respect for their elders that we somehow forgot as we modernized. Well, we as the Western society, I mean, it still exists in indigenous societies. It still exists a little bit in Asia and Latin America, but quite frankly, everywhere in the world,

if you had a choice between going to grandpa or Google to go get your information, you go to Google. And I think that that has meant that we have lost that opportunity to tap into the wisdom of the elders. And I think that that has meant that we have lost that opportunity to tap into the wisdom of the elders. But I don't think we're gonna go back to that. I don't think we're in an era

where it's gonna be all about reverence of the elders again. I think it's about relevance. So how do we help our elders and elders, if you could be an elder at 40, if you are, Terry Crews, who you had on the show recently, he's an elder and he, if you are, Terry Crews, who you had on the show recently, I'm, you know, he's an elder and he's in his fifties, but he was an elder when he was in his forties

amongst some of the people he was hanging around. And so how do we create a relationship between the young and the old in such a way that they can learn from each other? Yeah, my wife's father, he passed away a couple of years ago at 91, but he was a civil engineer in Alaska in Anchorage and was instrumental in the construction

of a lot of the downtown buildings and institutions, including like their fabulous art museum. And he worked with a lot of the construction entities were run by Native American people who have that reverence and respect. And even though he was like losing his sight and all of these things, they kept like hiring him for all of these jobs

up until like the very end of his life. Like he was making more money and more kind of like meaningfully employed than he had been throughout his career, which speaks to relevance and him continuing to find meaning in his life. And yes, we're not going back to that, but I think this idea of relevance is so important

as exemplified through your experience with Airbnb. So maybe we can kind of step back a little bit and kind of contextualize this with your story. So my story is, you know, grew up in Southern California, went up to Northern California for college. We both went to Stanford. You swam, I played water polo. You're a water polo player.

We were a couple of years separated, but we have some common friends from that era. And we used to swim in the same pool. And I went to business school there and a couple of years out of that business school started a boutique hotel company. You went straight to Stanford Business School, right? That would rarely happen these days.

It really doesn't. I was 23 when I graduated from Stanford Business School. Very unusual. Seth Godin and I were the two youngest people in our class. I heard when you were on Tim Ferriss' podcast talking about the kind of mastermind group that you formed with him and you guys would get together and talk about business ideas and you ended up co-writing a book with Seth right in business school. I did. And we're

deep, close friends because we were both sort of weirdos in business school. So a couple of years out of business school, I started a boutique hotel company called Joie de Vivre, meaning joy of life and created 52 boutique hotels around California. And then I sold it and we can come back to that possibly. And I sold it partly because my life was falling apart. We'll come back to that. Let's go forward and say, okay, I created some space in my life. And that's when I was called by Brian Chesky, the co-founder and CEO of Airbnb. And I quite frankly, 10 years ago, didn't know what Airbnb was. I was this hotelier who was about to get disrupted by Airbnb and I didn't really know what this was.

this was. And he asked if I could be his in-house mentor and help this little tech startup become a global hospitality brand. And so I joined and quickly became known as the modern elder at Airbnb, which was not exactly the title I was looking for. Yeah. At age what? You were like 52? I was 52. Brian was 31. Average age in the company was 26. So do the math. And they called me the modern elder partly because they said, Joe Gebbia, one of the other co-founders said, Chip, you're as curious as you are wise. I was like, oh, well, I don't love the title modern elder, but if a modern elder is someone who's as curious as they are wise, and they know how to have the right alchemy of curiosity and wisdom in their life, that describes me pretty well. And I want to, sorry to interrupt, but I do want to put a finer point on how you were able to kind of cultivate that curiosity in the wake of a successful exit from your company. Maybe we can

come back to that because I think it is related to one other thing that you want to talk about. Yeah, yeah, I'll come back to that. And I'll just tell a little bit of that Airbnb story now. Is that, sure. That sounds good. Yeah, yeah. So, yes, I joined this place. I'd never been in a tech company before.

I thought they wanted me for my knowledge of the hospitality industry, but frankly, it didn't really matter how many rooms made cleans in an eight hour shift in the Airbnb host world. So, you know, within actually it was the third day on the job, I was in a meeting where Brian had said, listen, go spend a lot of time with the engineers. You've never been in a tech company before.

Start learning the lingo. And so I thought I was supposed to be the mentor, but at the end of an hour meeting with a bunch of engineers, I knew I was the intern. I was like Robert De Niro in the movie with Anne Hathaway, but he came in as the intern and he became the mentor. I actually came in as the mentor and now I'm the intern. And what I realized is that I didn't understand the language, but that didn't mean I couldn't learn it. When I say the language, I meant like in that meeting, someone turned to me, the guy running the meeting,

a 25-year-old guy turns to me and says, Chip, if you shipped a feature and no one used it, did it really ship? And I was like, I have no idea what you're talking about. Shipping a feature, I've never worked in a tech company. deal. You're talking about shipping a feature. I've never worked in a tech company. So I had to acknowledge that I was not the smartest person in the room. I might've been the most curious person in the room at times and maybe the wisest, but I had to be open to learning. And my father said to me, Chip, how could you turn your fear into curiosity? And that was a really

great reframe for me because I guess, you know, at 52, having run a company for 24 years, taking it from one person to 3,500 people, there was a part of me that in my early to mid fifties, I was thinking, oh, what if my last career, you know, step is a big mistake and I'm just a huge failure here. So I think part of what really helped was I was willing to be humble and vulnerable about what I didn't know. And often I was asking questions that helped the company to see their blind spots or see our blind spots. And I think it was that process that helped the company to see their blind spots or see our blind spots. And I think it was that process that helped me to see that, gosh, more tech companies could use a modern elder.

I just watched, we crashed. And of course, and then there's Super Pumped and then there's the Inventor with Elizabeth Holmes. I mean, thank God there's no Airbnb movie like that. This mini series, drama mini series of like, you know, these crash and burn tales. But if you look at it, none of those companies really had a modern elder.

Well, it's interesting, because you wrote a blog post about this on your Wisdom Well blog. I watched all those founder series, like I'm fascinated by them and they vary in quality, but the recurring theme is ego gets the best of these people when it spirals out of control. But in the example of Super Pumped, which is about Travis Kalanick and Uber, there actually was a modern elder in that context. They had Bill Gurley, who is the benchmark VC,

who's sort of the stand in for the modern elder, but he's butting up against an ego that is not having it. And that of course, you know, sows the seeds for the downfall of his career. And the big difference for him, and you had Bruce Dunleavy for WeWork, who I went to business school with, same class as me, but investors don't have time to be 24 hours a day in house at the company.

So, you know, Bill or Bruce will come to a meeting and say, okay, what's going on? And, but then they go back and they look at the rest of their portfolio. And, and ultimately Bill got more involved in the business, but quite frankly, he could see what happens in a meeting. And of course, you'd see some signs of serious hubris. And partly that's because Silicon Valley wants hubris. Right. It's funny, you know, there's an element of like Silicon Valley wants the confident, super pumped CEO founder, and then they want them to miraculously move from hubris to humility as a leader. It's the package.

Like if you want the guy who has the massive vision and the audacity to not only dream big, but execute on that, you're gonna get the other side of it. You are, and this is why, you know, Brian Chesky, let's talk about him for a moment. When Brian approached me and said, I want you to come in-house and full-time at Airbnb and be my mentor,

but also be the head of global hospitality and strategy and a bunch of other things, I had to look at him and say, okay, this guy, I'm 52, he's 31. I'm gonna report to him, but I'm gonna be his mentor. That's gonna be sort of odd. What's it gonna be like to report to my mentee? And I had to have a level of confidence

that he wanted to learn and that he was, he had the hubris to go out and raise money, but he had the humility to build a culture and a leadership team and to maybe even take some direction occasionally from me. And so I think that was the key. And that's rare. It is rare.

And that's why there's still the founders and it's functional. It's amazing. I mean, you have three founders at Airbnb. It's over a hundred billion dollar company now. It's by far the most valuable hospitality company in the world. And the three founders are still very actively involved.

That's never happened before. There's never been a company that has had that. And I'm proud of, I mean, I made all kinds of mistakes while I was there and the company would have done well without me. And yet I am very proud that the three of those founders are still working together as they are. Because I think the glue that needed to happen

amongst the three was partly between me and a couple other people who helped them to feel that sense of what each of them offered to the company and to each other. What's an example of some of the wisdom that you were able to impart and also the receptivity of Chesky and his team to what you had to offer? Sometimes it was as simple as,

I mean, some of it was just little mechanical things because one of the things you get better at as you get older is you've had the pattern recognition in your life to see what worked and what didn't. And so some of it was simple stuff like, Brian, you went into that meeting trying to sell the leadership team on something and you knew there were two people in that meeting on the team who are gonna probably be critics of it. What would have been great is if you had spent some one-on-one time with each of both of them before the meeting

so they could actually air some of their concerns instead of feeling like they had to actually air it amongst everybody else. Because then you could have adapted the plan a little bit. So that's a simple thing. Or another simple thing would be like at Thanksgiving, we had all been running just crazy, 70, 80, 90 hour weeks flying everywhere.

We're a global company. And the leadership team's families weren't seeing us. And so it was Thanksgiving. And I said to Brian, what if you sent just a thank you note, maybe a bottle of wine or some flowers to the spouses and family members of all the leadership team and just say this Thanksgiving, I just want to say thanks to you. Because what's happening behind the scenes, Brian is, you know, Brian was not in, he wasn't married. He didn't have kids,

but he didn't realize that others did. And, you know, behind the scenes, there was not in, he wasn't married. He didn't have kids, but he didn't realize that others did. And, you know, behind the scenes, there's this person, the spouse saying, I don't want you to work this much, you know? And what we needed to really do is respect that. So those are a couple of simple ideas, but we work, you know, I mean, Adam Newman wanted to do a major strategic partnership with Airbnb.

Adam Newman wanted to do a major strategic partnership with Airbnb. And Brian sort of had some cognitive dissonance on it. He could see some of the value of it at one time. But I said, Brian, this guy is a Messiah, right? You've seen him act that way. How are you gonna create a logical business relationship with someone who believes they're the Messiah? How are you gonna create a logical business relationship with someone who believes they're the Messiah?

So, but it was, I would say that a lot of my wisdom related to emotional intelligence. How do you develop emotional intelligence as a leader when you've had no background in being a leader? Yeah. Why do you think that Brian singled you out for this role? Like what, I mean, you have this robust history of being a mentor that started, you know,

actually quite early in your life and in your career, but why do you think he, you know, A, had the foresight to see the need for a mentor and what was it about you that he found attractive? So Brian is, got the most voracious appetite for learning that I've ever met in my life. And so he, like when Airbnb in 2011 had this, someone like totally trashed an apartment,

he decided to go to the former head of the CIA to learn about safety and security and how he could actually make the Airbnb platform safer. And so he also had been talking to a guy named John Donahoe. So John's a friend of mine. He and I were in YPO together and we were in the same forum. John's the CEO of Nike now. But back then, John was about 10 years ago,

the eBay CEO. And so Brian, knowing that eBay had some similarities to Airbnb in terms of there was a two-sided marketplace, he was working with John as a mentor part-time. And so John, I think, said to Brian, you should talk to Chip. And Brian was like, well, tell me more about Chip. And so as, I think said to Brian, you should talk to Chip. And Brian was like, well, tell me more about Chip.

And so as Brian learned more, Brian said, oh man, I wanna learn from him. But I think what Brian initially was looking for was someone who had the knowledge of the hospitality and travel industry, because when I joined the company, no one in the company had that background at all. But I think what he learned over time was he said, I hired you for your knowledge,

but what I've really gotten was your wisdom. And it's your wisdom of understanding people and leadership and strategy. So I think, one of the things we get better at as we get older is holistic thinking. Arthur Brooks talks about this in his new book from Strength to Strength. Yeah, he's coming in soon.

Oh, is he? Oh man, we're buddies. Yeah, you guys are like every time in researching like articles and stuff like that, it's like your name and his name always kind of are appearing in the same. I love, you know, he's so, like speaking of super pumped, I mean, this is a guy who's adrenalized

and I really enjoy sometimes sparring with him, you know, intellectual jousting. But in his book, From Strength to Strength, he talks about, you know, going from fluid intelligence to crystallized intelligence. Fluid intelligence is very focused, logical, you know, and it's about actually innovating within a certain linear course.

But crystallized intelligence is when you are looking at things more holistically. Because one of the things that's interesting about our brain is as we age, we actually move from being very focused in the brain to actually having four-wheel drive of the brain. We actually move much more lyrically and logically from one side, the right side to the left side.

So, which is great because what it means is that we can actually look systemically and holistically at things and connect the dots. It makes sense because you've accumulated so many experiences over the course of your life. You get to a point where you're able to synthesize all of that information. And I feel like just, you know, at 55 now,

like an ability to kind of see things a little bit more clearly than I could in younger years. I think whether it's wisdom or intuition, pattern recognition, you get to a place where the right answer just sort of pops up. And it's not because you've done some mathematical theory to get there. It's actually coming from your lived experience.

I like to think of wisdom as metabolized experience, which leads to distilled compassion. And so in both cases, the metabolizing of experience, how am I digesting my experience, leads to understanding yourself more, the world more, and then being able to have some level of compassion. Because I think wisdom without compassion is just doing something for yourself.

Right. One of the things I did early on, Rich, when I was 28 years old, so I started my boutique hotel company when I was 26. At 28, I realized I was clueless. I knew I was clueless at 26 too, because I bought a motel in San Francisco in a bad neighborhood.

It was a pay-by-the-hour motel, which if you know what that means, it means it was very popular at lunchtime. People would come and have their little affair at lunchtime and then go home or go back to the office. And so at age 28, two years into it, I realized like, I don't know if this business is gonna work. And we had the San Francisco Loma Prieta earthquake.

And I was like, oh my God, we have no business now. So I started doing something that actually I would recommend everybody do. I mean, it's just simple about metabolizing experience. Every weekend, I would sit down with a diary. Somebody had given it to me as diary. I didn't use it as a diary. I used it as a place to understand my wisdom.

And so I called it my wisdom book. And each weekend I would create like three, four, maybe eight different bullet points of what I'd learned that week. And often the learning was painful. It was things like, oh man, Linda Ronstad wanted to take over our whole hotel, but I took a day to get back to her travel agent

and they booked something else. So it's like, okay, simple lesson, which was like, okay, if a travel agent is- Move quickly. Yeah, move quickly. I mean, don't waste time. And so long story short is every weekend for over 30 years, I sat down and wrote in one of 10 wisdom books and now Google Docs with what I'd learned that week.

And the value in doing this is it actually allows you to start to metabolize your experience. You could do this for a team. You could say once a quarter, we as a leadership team are gonna do a vulnerable kind of experience where we said, what was my biggest lesson this quarter?

And then let each person speak up about what was the lesson, what did they learn from it and how they're going to use it moving forward? Because that's a way we start to metabolize experience into wisdom. Yeah, that's amazing. So that's a practice that you still to this day do, right? I still do, yeah, yeah. So let me be clear because I want to be fully honest. I do it once a month now. I don't do it every weekend anymore. But I did it every weekend for about 30 years. Wow.

It conjures in my mind sort of a hybrid between a very directed journaling exercise where you're going in, you're not just, like doing morning pages where you're vomiting out, whatever. You're very intentional about what it is that you're focused on writing about matched with a practice that, you know, I've been in recovery for a long time.

This is sort of like a daily thing to do an inventory, right, to like check yourself a little bit. Like, where am I going wrong? How did I contribute to that thing not going well, et cetera, which leads to, you know, a deeper level of self-awareness. Yeah, I wish someone had told me this. You know, it's such a simple practice, but such a profound one

in the sense of our life is meant to be examined, but not examined as if we did something wrong. Maybe we made a mistake, but the lesson from that mistake actually makes us smarter for the future or wiser for the future. And so I recommend it for most of the people that I work with and there's about six CEOs I mentor today,

just as friends. I mean, I don't do it for a living. And I tell them, it's really simple, but like so many things that are simple, it's a practice. Yeah. And you have to do it. Otherwise it won't mean anything. We should mention that the pay-by-hour hotel,

Fleabag Motel in the Tenderloin District of San Francisco became the Phoenix. I've stayed there many times. It's such an epic hotel and such a diverse dynamic neighborhood. I was in San Francisco this past weekend. I did not stay at the Phoenix. I ended up staying at the Proper Hotel,

which is on the edge of the Tenderloin. The Tenderloin has really not gotten much better since I lived in San Francisco. 35 years ago and it's actually worse than it was 35 years. It's one of the few neighborhoods in San Francisco that hasn't gentrified. Yeah, it's actually worse than it was 35 years ago. It's one of the few neighborhoods in San Francisco that hasn't gentrified. Yeah, it's a seedy neighborhood. But there's a lot, it is seedy

and there's a lot of rich history there and a lot of really interesting cultural things. I was on the board of Glide Memorial Church, Cecil Williams Church in the Tenderloin for many years and just beautiful. There's a lot of humanity there. It's sort of like going to India. Yeah, yeah, yeah, yeah, yeah.

But the Phoenix became known as like the rock and roll hotel. Like all the bands stayed there, like just legends of music over the years, which is pretty cool. Like, was that an intention going into it or did that grow out of the hip of- I was a 26 year old. I was a 26 year old who said, I wanna get into the boutique hotel business

because it seems as if it's about to take off. So Ian Schrager and Bill Kempton were the first two US boutique hoteliers. I was the one right after them. And I was like, they're successful. I wanna be successful too. And so I said, each time we would create a hotel, let's imagine a magazine that defines the hotel.

And because magazines and boutique hotels have something in common, they're niche oriented and lifestyle oriented. So that first hotel, the Phoenix was based upon Rolling Stone magazine. And we came up with five adjectives that defined Rolling Stone, funky, irreverent, adventurous, cool, and young at heart.

And everything we did in creating that first hotel had to come back to those five adjectives. And then miraculously, what we found was that the people who fell in love with the hotel were people who would use those five adjectives to describe themselves on a good day. So it was like, you are where you sleep. So that's what a boutique hotel is.

It's sort of like an identity refreshment. It's aspirational. And so every hotel, yeah, so the first hotel was all about rock and roll aspirational. And so every hotel, yeah, so the first hotel was all about rock and roll bands because at 26, like, oh yeah, I'd love to have Nirvana and Pearl Jam and Red Hot Chili Peppers staying here all at the same time on their way to becoming famous bands.

And that happened a lot. Those three bands actually toured a lot together. So that's how it started. And then all 52 of the boutique hotels were based upon different magazines. So each one had its own magazine. It did, or sometimes a mixture of two, like there's a hotel Vitali in San Francisco

close to the pandemic. So that was dwell meets real simple. So modern, urbane, fresh, natural, and nurturing. And so it was, you know, so in some ways I was like an armchair psychologist by saying, okay, what are some of the personalities out there who would like to see a hotel that's their perfect habitat? Yeah, well, creativity is central to this,

a knack for marketing, some foresight about where this industry was headed. It's hard to imagine at this point, a world without boutique hotels, like no young person is staying at a Hyatt or a Hilton. They're actually staying in Airbnb. Well, yeah, exactly. Like, yeah, right.

Actually, boutique hotels were sort of a precursor for Airbnb. Sure. Yeah, of course, like a bespoke environment, right? And just having stayed at the proper, like that chain and many others owe's legacy to this kind of legwork that you did many years ago. Yeah, and if you look at, if you go into almost any full service Hyatt

or Hilton today, they are trying to be like a boutique hotel. The bar is sort of central. The music is definitely not the music of 20 years ago. The design is very different than it used to be. So I think what the chains realized of 20 years ago, the design is very different than it used to be. So I think what the chains realized, and then ultimately they bought many of the boutique hotels.

My company is part of Hyatt. Kempton is part of Intercontinental. The irony of that. Yeah, Marriott hired Ian Schrager. Like, okay, there we go. The bottom line is the big hotel chains realized that they needed to get hip because the customer wanted more experience. They didn't just want a boring, predictable experience.

Back to this idea of creativity. It's interesting that out of business school, your initial kind of career path was commercial real estate, not exactly known for creative inspiration, right? Just buying office space and leasing it, et cetera. So how did you reconcile that creative spark that I'm sure you had some self-awareness around and maybe a latent desire to be an entrepreneur

with being in that track and then ultimately getting to the point where you were capable of manifesting it. So, you know, it's funny, between my first and second year of business school, I worked in New York for Morgan Stanley's real estate division. That's hard.

It's so hard to visualize you doing that. I know, I know, I know. But sort of classic, like you're a business school student. I mean, I was 22 between my first and second year of business school. The fact that I was wearing suspenders, smoking cigars and making deals as a Morgan Stanley real estate guy was sort of beyond me. And they loved me and gave me some great job offers

after business school. But I just knew, I think the question I had in my mind was, what do I want to be when I grow up and what's going to take me there? Because actually the amount of money they were throwing at me and the amount of prestige they were going to give me, they even knew that I wanted to be, you know, maybe back in the West coast, sometimes soon. So they're going to like bring me to New York for a year and then, you know, help run and open the office in LA, the real estate office.

I was like, you don't do this for a 22 or 23 year old. But I turned it down. I turned down all the other job offers. I took a job out of business school for $2,000 a month, $24,000 a year, which was crazy. I mean, the average salary out of business school at that point was about 85 to $90,000 a year. But I took it because it was working for a creative,

what I thought was a creative real estate development company that was basically redeveloping what was called Showplace Square, which was south of market. And I just thought, you know what, I'm gonna go work there. And the guy who ran the show and founded it said,

you could become a partner within a year. And so I went to work there, but it wasn't creative enough. I mean, I thought I chose creativity over money and even the creative real estate development thing I went to do wasn't creative enough for me. So that's when I get to know a guy named Bill Graham, Bill Graham, the concert promoter. So Bill Graham was building Shoreline Amphitheater

down in Mountain View and on the peninsula in the Bay Area. And our CEO founder wanted me to do a deal with Bill Graham. So we were going to be his partner on Shoreline Amphitheater. I was like, okay, well, good luck. I mean, Graham's got the money. He knows how to develop it. What's our part in this thing? what's our part in this thing? So ultimately there was no deal to be made, but Bill Graham pulled me aside. He said, I like you, Sonny. He says, and at this point I was 25. I like your chutzpah. I like your, you know, you're a mensch.

You know what you really need to do is you really need to create a hotel in San Francisco for the rock and roll bands. Because I have people coming to the Warfield and the Fillmore and they're coming to Great American Music Hall. And there's the only place they go is an old place called the Miyako that was in Japan town, which ultimately became the Hotel Kabuki,

which is a Joie de vivre hotel. And they said, there's no great place for them to stay. And that's when the light bulb- Wheels started to turn. Over my head and I was like, okay, maybe that's what I should do. So I went to the founder Over my head and I was like, okay, maybe that's what I should do. So I went to the founder of our firm and I said, I have a really creative idea for you.

And I told him what Bill Graham had said to me and it was like, dude, we're not gonna get in the hotel business. Like we'll lose our shirts. It's a terrible business. Yeah, that's the thing with hotels, right? Like if you wanna lose a ton of money, get into hotels. Yeah, exactly.

Same with restaurants, it's sort of, but I just said, you know what, I'm gonna go do it. And so I started this company on my 26th birthday and bought the motel on a 40 year land lease for $800,000. Can you imagine buying a 44 room property on an acre of land in San Francisco for $800,000? You can't buy a condo for $800,000 in San Francisco. A garage. Yeah, so that's what I bought.

And here we are 36 years later, and I still own the Phoenix, although we only have about two and a half, three years left on the land lease. So how did you, that story aside, like how did you transcend that kind of conventional wisdom around hotels are the way to lose money? I'm thinking about one of those, a scene in one of the Ocean's 11 movies where Brad

Pitt, like it appears that he bought the Standard Hotel on Sunset and he's like hemorrhaging all the money that he had stolen in the earlier movie and everyone's making fun of him. That's so funny. That particular property, before it was bought by Andre Blasch and made it into the standard, I had it in escrow, but it was an old Jewish convalescent home. And I'll never forget, so this is, now we're getting into some good stories. I walked through it after we were in escrow

and this older Jewish woman came up to me and pulled on my shirt sleeve and she says, are you the guy who's gonna be actually buying this and throwing us out? Oh no. And I just had this crisis of conscience. And I said, not gonna do that. So- We'll let Brad Pitt do it.

We'll let Brad Pitt do it, exactly. So what, I think what made us different and the reason we succeeded is we got clear that, you know, the reason a person chooses a boutique hotel is because there's an aspirational lifestyle piece to it. Now, Ian Schrager, who was really one of the first, he and Bill Kipton were the two first boutique hoteliers. They had different perspectives. So Schrager's perspective was it's all about being cool, hip, and maybe even narcissistic. Schrager's perspective was it's all about being cool, hip, and maybe even narcissistic. And so all of his hotels were about getting behind the velvet rope.

Sure. And Kempton's was much more sort of homespun European, more like an inn kind of experience where you have a good restaurant there and a wine hour. But they sort of kept playing the same game over and over again. And my point of view was like, geez, there's so many different kinds of personalities out there. Let's have this very schizophrenic company where we have 52 different hotels with all kinds of different personalities that we're actually serving. And so that's how- Right. But that's riskier because some of those aren't going to work. It's very risky. It's riskier and in some ways it's stupid because we were like a branding agency.

Every single time we were creating a new hotel, it was a new brand, a new market we were going after, but it was very creative. It was so much fun to create a hotel based upon Vanity Fair meets Outside Magazine, which was a place called Costanoa, a luxury campground. And so it was just, I loved it until I hated it. So can I talk about that story now?

Yeah, let's talk about that. Oy vey, oy vey, Rich. I was so, oh man. So first of all, let's go back to, I was 26. So one of the things we haven't talked about yet is, so I played water polo at Stanford. I was in a fraternity at Stanford. I was Steven Townsend Conley Jr.

My dad was Steven Senior. My dad was a Marine captain in the reserves. I went to the same high school as my dad. My dad was my baseball coach. I was the star pitcher. My dad was the scout master and an Eagle Scout. And I was an Eagle Scout as well. I went to the same high school as my dad,

played water polo and swam like my dad. Then went to Stanford University like my dad. That's heavy. Got a girlfriend. There's a lot. Got a girlfriend in freshman year of college, just like my dad did, who ultimately became my mom.

Now you're really betraying your truth. Exactly. So I was like, oh my gosh. So I was on this path. Now I did join a different fraternity than my dad did who ultimately became my mom. Now you're really betraying your truth. Exactly. So I was like, oh my gosh. So I was on this path. Now I did join a different fraternity than my dad did. And I did play water polo. You were a fight out? I was a fight out.

Yeah, that's where all the water polo players were. All the water polo players were there. But I had a secret. And the secret was something that I was way subliminal, but I was gay. And I, you know, how was I ever gonna tell my dad, the Marine captain, you know, Steven senior, not Steven junior chip off the old block that I was gay.

And so what happened was in my early twenties, when I went to work for Morgan Stanley in New York, that was the first time I ever walked into a gay bar. And I was like, oh man, I, you know, it was like in wizard of Oz when it goes from black and white to technicolor, that's sort of what it felt like. And I was like, okay, but it was like in Wizard of Oz when it goes from black and white to technicolor, that's sort of what it felt like. And I was like, okay, but it was hard.

And my process of coming out as someone who had been an all-American athlete and in a fraternity and the world I lived in, it was back then. I mean, today it's a totally different story, but back then it was pretty hard. So fast forward a couple of years later, I am now the CEO at age 26 of a boutique hotel company.

Well, first let me just backtrack a little bit. Like how did it go with Chip Senior? Chip Senior had- Chip off the old block. He really, so dad actually initially took it well and then not so well and wanted me to go to reparative therapy. And so I, can I talk? I can talk about this stuff.

Okay. So I ended up going to therapy with a guy named Bernie Zilbergeld, who wrote a book called Male Sexuality. He's no longer living. And he set me up with a surrogate because Bernie spent a bunch of time with me. And he said, listen, dude, you know,

you might be bisexual, but I'm pretty sure you're straight. And you just need to, you know to have the right woman with you. And there's this woman, Annie, and Annie is so hot. Annie is so hot. And so you're gonna have sex with Annie every two weeks. She's gonna report back to me about what actually happened. And then you're just gonna, I can tell you, I know.

Having sex like in a transactional way? Lights fucked out. And I'm I can tell you, I know. Having sex like in a transactional way? Lights fucked out and I'm gonna like, yeah, actual sex. And this is also, this is during AIDS. This is like, this is 1984, 83, 84, 85. So, you know, of course we were safe and I was having sex with her, but I was going back to Bernie and saying, you know, it doesn't feel the same as it did with Victor.

I was going back to Bernie and saying, you know, it doesn't feel the same as it did with Victor. And so long story short is dad finally got used to the idea that, you know, reparative therapy wasn't gonna work. And the reason this is relevant to my boutique hotel career is because when I started my hotel company, there was an element for me, like I needed to prove myself. I needed to go say, okay, I am going to be successful. And because I'll be successful, you will admire and like me.

And therefore it's my way of making up for the fact that I felt like I had both disappointed my dad, but also that I was not normal, or I was not as good as my fraternity brothers because I was gay and they were straight. Right, but you could have stayed at Morgan Stanley and checked all of those boxes. So there was something percolating inside of you

that you needed to find a new and different way that was more in alignment with your blueprint. Isn't that interesting? And be successful in that regard. It's very interesting, Rich, because there's an element for me, like somehow my true North knew, and again, this is stereotyping,

but as a gay man, I had a great design eye. Okay, is that inborn? I don't know what that says about gay men, but guess what? Gay men tend to have that. I'm pretty empathetic by nature. I'm pretty good at understanding other people and being open to being in service of them.

And so for all those reasons, boutique hotels made a lot of sense. And so I started this company. It grows to be the second largest boutique hotel company in the US. Along the way, my sense of identity, my sense of who I am from age 26 to let's say 47 or 48 is, dudes, I am this founder and CEO of this company that's grown to 3,500 employees. And then I had, it's like the world changed almost overnight.

It's like the world changed almost overnight. So it was early 2008. And I could see the great recession coming based upon our numbers. I had written a book. So I've written five books. And my third book I had written a few months earlier called Peak, How Great Companies Get Their Mojo from Maslow. It became a huge hit.

And I was giving speeches on it. And I was loving that. I loved writing. I love speaking. It's like all of a sudden, like the thing that had been my calling, there's a new calling and the new calling is knocking on the door. And I feel like a little bit, you know, unloyal, disloyal because the new calling was this writing, speaking thing. And then I had, so I had a foster son, African-American foster son, who was having some

trouble with the law as an adult. And I had a long-term relationship potentially ending. I was running out of cash because of the great recession. And then one of my closest friends who has the exact same name I have, his name is Chip, not the exact first name. So Chip takes his own life. name, first name. So Chip takes his own life. He dies by suicide. And so to go to the funeral of a friend of yours who has the exact same name, strange name. And I was sort of in the early stage of a dark night of my own soul was really uncanny. And then soon after that, I, so Gavin Newsom, who's the governor of California was my first mentee when I was 35 and he was 28 before he was the mayor of San Francisco,

before he was the governor of California. So I went to his bachelor party at AT&T ballpark and I hit a triple out to the warning track and I was sliding into third base at age 48, 47, 48. And I was, into third base at age 47, 48. And I broke my ankle. And then I got a septic condition in my leg. And so I was on a strong antibiotic and I was giving a speech in St. Louis.

And after the speech, I was sitting in signing books and I went flat on, I didn't go flat on, I went unconscious. Like literally at the signing table? At the signing table, I went unconscious. They put me on the ground. I guess I was out for like four or five minutes. And they called the paramedics, thankfully. And I was on the ground.

And next thing I knew I was coming to, I had no idea where I was or what had happened. The paramedics put me on the gurney and that was the first time I went flatline. So I flatlined, they had to bring out the paddles to shock me back to life. And over the next 90 minutes, I flatlined nine times in 90 minutes.

And what happened for me and how this relates to my whole history was I had this moment of, we can talk about what it's like to go to the other side. Yeah, I definitely wanna- It was a true NDE. I definitely wanna hear more about that. But what it really forced me to look at is, the hoteliers wake up call.

I had to look at my life and say, is this the life I want? I was having, I guess, a midlife crisis in some way, but I was more than anything, I was having what Brené Brown, my friend, would call a midlife unraveling. Like it was, everything was so tightly wound and it needed to unwind some.

And so- Did you have self-awareness of that at the time or were you kind of like pushing that down and just in the kind of move forward? I knew I was really unhappy. I knew I wasn't happy. I knew that when I was at Chip's funeral and his memorial service

and people were telling their Chip stories and I had thought about going to the Golden Gate Bridge myself and jumping, I really was at that place of saying, I don't know how to disengage from this identity I've created. The identity that defined me was this successful entrepreneur who's creative, who creates an amazing culture, who happens to write books and give speeches and do TED Talks. And all of this was the, it was like the Wizard of Oz, but I was-

It's a very aspirational identity that anybody would wanna have. And obviously was the manifestation of what you had dreamed about. And? So how could you be unhappy in that condition? I was unhappy because I, first of all, I didn't, it wasn't creative enough.

Let's go back to that. I had created a company that was a creativity company, but by the time we had 3,500 employees and now we're in the great recession and we've grown, opened 15 hotels in the last 21 months, like in the worst of times, like I was just trying to keep the lights on. Yeah, it's about spreadsheets and I loved writing.

And then I was also having all this other stuff happening in my personal life, my son and foster son and my relationship ending. And so what happened was I had this flatline experience. I had Man's Search for Meaning, Viktor Frankl's book in my backpack. Because that's my way of knowing how dark I was at that time

was I was carrying around Viktor Frankl's book as the reminder that I was not in a concentration camp. The concentration camp was in my own mind. Yeah. So I, while I was in the hospital for a couple of days while they're doing all these tests and ultimately they sort of said, I think we think you're allergic to augment

and the antibiotic you're on. So I was reading Victor Frankl's book about being in a concentration camp. And I came up with an equation, despair equals suffering minus meaning., despair equals suffering minus meaning. Despair equals suffering minus meaning. So if suffering is ever present, and if you're a Buddhist,

that's the first noble truth of Buddhism is suffering is ever present. Then despair and meaning are inversely proportional. So when you're going through a really crappy time, the key is to ask yourself what's the meaning and it really did take me 20 years back to when i said okay my memory my wisdom book you know what did i learn this week what so i really i got very fixated on what am i learning what am i learning and what's the meaning in this and ultimately within two years, less than two years, I'd sold the company at the bottom of the great recession. I had ended the romantic relationship I'd been in for a long time

that wasn't working. I'd gotten my foster son out of prison, out of San Quentin because a federal judge let him out and said, he's in this, he's not guilty. His constitutional rights were abridged. Wow. And I was on a path to saying, in this, he's not guilty. His constitutional rights were abridged. And I was on a path to saying, I'm ready for the magic. I mean, I'm ready to actually create space in my life and see what emerges because I've spent the last two dozen years building this identity. And I haven't, it's not a facade. I mean, I was the whole time I was living my truth,

but I was also getting to a place where I was so fixated with the identity that I wasn't actually giving space for the new creativity to come in. And so, yeah, and that it was not long after that, that Airbnb came calling. So in the midst of experiencing that level of despair and the self-awareness that you had to find

or attach some meaning to it. Walk me through the process of how you identified that. Because I think, you know, there's probably a lot of people who are experiencing some level of despair. It's been a really hard couple of years. Is the idea that there is universal meaning in all suffering,

or is it that you have to find a personal connection, like your own definition of how it could be meaningful for you? Well, let's use Frankl for a minute. So if Victor Frankl and folks were in the concentration camp, what he says in his book is that when he saw people having hope and had a sense of the other side of this.

Not false hope. The people who actually died quickly were the ones who said, by this date, we are gonna be out of here. And that was a false hope because they had no control over them being released by that date. But there was more of a focus on hope

for what the future will be and how this experience will actually create maybe a better life for them. And so that's not a bad way to look at it because what we do know is that when we're going through difficult times, it is exceptionally character building. It can be, not for everybody.

Sometimes people give up. Sometimes people do whatever they do. And where they drink, they use distractions. They use alcohol, they use drugs, they use porn, they use whatever it is to distract themselves from the learning. Is work sometimes as well. So I think the key for me was to ask myself,

how is my character? This may not be a resume builder, surviving a downturn. So how do we, to use some David Brooks thinking, how do we move from the resume values to the eulogy values? And the eulogy values are the values that people will say about you at your funeral. And they're the character qualities.

And I think it was around that age, in my late forties, that I realized I'd spent my life building a resume. And I'd built some character qualities along the way, but I was never really focused on how am I developing those character qualities. And if you want a time to develop your character qualities, use the dark time to do that.

Because it's an exceptional time and it's a time where you actually often have to break habits. Yeah, I have my own experience with that. Yeah? Yeah. Tell us. It's painful. Well, I mean, I'm not gonna bore everyone who's listening to this with that.

They're on this show because they were like, they're you. But I mean, I had a version of that reckoning at 40 and it was sort of a collision of a health scare with an existential crisis about how I was living my life. I was a corporate lawyer at the time and very unhappy, but also very much in the checking the boxes and trying to make sure that I was the dutiful son to parents with high expectations, et cetera, you know, something

that you know quite well and had to, you know, really deconstruct all of that and figure out who I wanted to be. And then spent a decade trying to figure that out. I'm still trying to figure it out. And I found, you know, a modality that I leveraged was endurance sports and all of the kind of quiet time that comes with that, that allowed me to, you know, develop a level of self-connection that I was lacking at the time and ultimately leading me, you know, kind of into a more intuition-based,

heart-centered place to be open to what was next. And, you know, Airbnb didn't call, but, you know, slowly other opportunities came. And that's kind of why I'm sitting here today. And that evolution and having it be on display for others has been incredibly cathartic to people to see your process. Especially, you're from 40 to 55.

I would say, you curve of happiness shows that 47.2 is the low point. Again, your mileage may vary, but from 40 to 55, a lot's going on. I use another emotional equation. Disappointment equals expectations minus reality. Right. So disappointment equals, so it's around 40 to 50, 55,

that you start to come face to face with the expectations that you have for yourself, the perfect spouse, that you're supposed to be president of the United States, how much wealth you're supposed to have, the second home you're supposed to have, the kids who are perfect. And in your 40s, you come face to face with the fact that none of that's actually happening.

And you also may come face to face with the fact that the success script that you were handed by your parents is not the script that you wanna write for yourself. And is not leading to the fulfillment that was implicitly promised. That's right. And so, lucky for me at 22, I came out of the closet because it forced me to actually come face to face with my success script from my parents and my lovely parents. I love my parents and they've been, after rough initial time, they've been incredibly supportive and

loving. And I love the fact that they're on a six week vacation right now at age 84. But what I can say is that being able to deconstruct the success script in such a way that you recognize that you're the screenwriter of your own life. And you need sometimes some guidance for how to write that screenplay. Partly because you may have constructed your life in a certain way. And it's not just like, oh, okay, now I'm gonna go do this other thing.

No, you actually have three kids and you get a spouse and you've got a mortgage and you're actually helping your ailing parents. At the same time, you're helping your teenagers. So you've got the spouse and you've got a mortgage and you're actually helping your ailing parents at the same time you're helping your teenagers. So you've got the sandwich generation going on. And so the process of doing that, I witnessed my father, my father who dutifully became a banker like his father

around his early 40s said, fuck this, I don't wanna do this. And he created a business when he had me at Stanford, my sister about to go to Stanford and then another sister gonna go to UC Berkeley a few years later. And he started a company at a time where it was really not opportune. So my father's been a role model for me in many ways.

And it is around our 40s and 50s. And some people's reaction to all that is go get the red Ferrari or have the affair. And I mean, often that's just another form of a distraction. Yeah. I wanna get into the mentorship piece, but before that, I'm not letting you off the hook

on that near-death experience. I wanna hear what that was like specifically. Well, since it happened nine times in 90 minutes and I had one particular nurse there by my side, four of those nine times. And each time I would come out of my NDE, I would say to her, here's what I saw. And she would say to me, that's what you said last time. And the last time was only about six minutes ago. So here's what I saw. And I've hung out with a lot of NDE folks.

There's even a, I'm fascinated by festivals because I'm a founding board member of the Burning Man nonprofit. And there's a festival in Northwestern Spain called the Pilgrimage of the Near-Death Experience. And everybody who has had a near-death experience is put in a coffin that's open. And you have a parade of coffins going down the street. And you're waving at everybody and everybody's drinking. And it sounds sort of weird and macabre. But so my experience was this. The first thing I noticed was that I was in a mountain chalet.

So like maybe, you know, let's say eight or 10,000 feet in some mountain range. It was like maybe a summer day. So there's no, I don't notice so I didn't notice any snow but there was this huge skylight in the living room the upstairs living room and the skylight was open and there was light coming in

and there was a kaleidoscope of colors that was actually being projected onto the wall I was about maybe 8 or 10 feet in the air, just sort of floating. I didn't see myself. I didn't observe myself. I just knew I was not on the ground. I was sort of observing from that place.

There were birds chirping. It was gorgeous. I mean, it was sort of quite beautiful. And then the thing that was most noticeable was on the ground was this beautiful wood floor. And on the ground, there was this frang floor. And on the ground, there was this frangipani scented, so like a tropically scented oil. It was very thick, like a viscous oil that was actually made it created a sheen on the floor. And the oil was going toward the staircase going

downstairs. But it's sort of like that Heinz 57 commercial anticipation. It's like the oil was dripping down the stairs exceptionally slowly. So what I noticed more than anything around this, there was no other people, there was no white light other than this light coming from the skylight, which was like a white light that led to the kaleidoscope of colors on the wall. What I noticed is how sensual it all was, the listening to the birds, the smelling of the frangipani, the beauty of it all.

At some point, I actually touched, my arm projected longer so I could touch the ground and touch the oil. And I think more than anything, what I felt was this sense of spaciousness and slowness. Now I had in 2005, we opened the Hotel Vitali and the Hotel Vitali had slippers in the room and one slipper said slow and the other slipper said down.

So if you had your slippers on, it said slow down. And that was one of my ideas for this hotel that was supposed to be like almost like a spa hotel in the financial district. Slow down. So I was in my own NDE that was just telling me to slow down. That is the experience I had. That's what I take from it. The other thing I take, so because again, Just the experience I had, that's what I take from it. The other thing I take, because again, the dripping of the oil was so slow. So I might be out for two minutes or three minutes when I had my NDE and I'd come back

and I felt like I'd been out for hours or days. But more than anything, what I got from it was just this deep sense of just slowing down. And when I slowed down, I realized that I'd spent my life running away from my emotions. And what I recognized was that I, because the recession had come on

and I was trying to figure out how to keep my company afloat, I was just a manic, crazy person. And I didn't wanna be that way anymore. And I'd spent my life, I'd spent since age 21 meditating, but I'd stopped meditating at that point. I was no longer meditating.

And so my exercise, I started practicing, you know, my meditation every morning and late in the day. And I just slowed my life down. And as I slowed my life down, I realized that I thought I just slowed my life down. And as I slowed my life down, I realized that I thought I loved what I was doing. And I did in some ways, my ego did. But one of the things that Carl Jung and Christian mystic Richard Rohr have talked about

is the fact that the, and Richard Rohr has come to our Modern Elder Academy as a student, as a student at 79 years old. Really? Yes, we'll talk about this. We'll talk about this when we talk about MEA. But so what I noticed was that when I slowed down, my ego started to melt.

And Richard Rohr and Carl Jung have both said that your primary operating system for the first half of your life is your ego and for the second half of your adult life, it's your soul. And yet none of us are issued operating instructions of how to move from driving automatic to driving stick shift. And it's almost like you're on a San Francisco

hilly road during a rainstorm and you're on Hyde Street trying to drive up with the cable car, the metal from the cable car tracks, meaning you're spinning your wheels. Because the process of moving from ego to soul or from automatic to stick shift, there's a complexity to it. And I had to have an NDE to recognize it and to slow down to see that I needed an operating system shift. And that's what happened. And it's a deeper, longer story than that.

And I wrote a book called Emotional Equations about it. But it was ultimately the thing that helped me to say, get out of jail free, Chip. You don't have to die. You don't have to be like your friend, Chip, who had took his own life. And I can start rewriting the script of how I want to live my life. And ultimately my experience going to Airbnb was a perfect segue for me because instead of being the sage on the stage, the hero, heroic CEO, I was the guide on the side. Right, worker among workers. I was the worker amongst workers

and I was the guy helping these three founders along with some other people. I mean, it was not just me, but I was really tightly wound with them to help them be successful. It's sort of like what a parent does with a child. Your ego doesn't have a space in that relationship. Yeah, what a beautiful insight and experience to have

to take this thing and attach meaning to it. It's such a specific experience, right? And in the many kind of flat lines that you had, that same vision recurred to you? Oh yeah, the nurse kept saying, you're so funny, you keep telling me the same thing. Right, and so, what do you make of that? I mean, you could say, well, this is your unconscious mind,

your subconscious trying to get your attention, or you can go, you know, down a more metaphysical rabbit hole with the whole thing, you being on the board of Burning Man and all of that, I'm gonna predict that you're seeing this as more of a metaphysical experience. Yeah, I mean, I saw it as this opportunity. I mean, I saw it as an opportunity for me

to have the courage to change everything. And the metaphysical side of it was very much, you know, this divine intervention and this sense like, okay, you know, you get another chance, Chip. Right, you're not ready to go, but you're ready to be reborn in a different way. Yeah, for sure.

You know, interestingly, my first hotel was called the Phoenix, the mythological bird that rises from its own ashes. So I was ready to be regenerated, which we'll talk about in a few minutes. I was ready to be regenerated, which we'll talk about in a few minutes. I was ready for regeneration, but I didn't know how to do that. And that's actually, I think a lot of people, there's a lot of people who are sort of in that place of realizing this isn't working anymore.

I don't need to have an NDE to learn that. But how do I re-script my life? How do I sculpt it in a different way? How do I break through the blocks and the habits that are in my way? Yeah, and I think tragically, all too many may have some version of that epiphany, but are feeling trapped in the circumstances of their life

due to the things that you mentioned, the mortgage, the responsibilities, et cetera. And so then they live out their remaining days in tension between those two things and unable to kind of figure out a path forward that would kind of resolve that internal conflict. Let's talk about mentorship because I, when I think of you and I look at you and in the limited amount of time that we spent together, to me, like you're this wise teacher. Like you are,

you have the teacher gene. I think you, you thrive in circumstances where, you know, whether it's on stage or one-on-one and in the modern elder academy, where you're imparting some experience-based wisdom that you've accumulated. I know you studied philosophy in college, et cetera. So this feels like very, my sense is that it feels very natural to you,

not that it isn't like sort of trained over the years, but the mentorship thing to me feels like your real self eking out, you know, earlier in life before the NDEs and all of that. I mean, the fact that at 35, you're mentoring Gavin Newsom, like when did the mentorship thing start and how has that become a thing? And like, kind of what role does that play

in terms of you being a mentor and the importance of mentorship in general? So quite specifically with Gavin, he was a hospitality entrepreneur. He had a company called Plump Jack. I remember that living in San Francisco. Exactly. It was the early 90s.

There was a wine store and there was a restaurant and then there was a hotel. Like right on Fillmore, like a Union Street area. Yeah, exactly, Cal Hollow. Long story short is his sister came to me, Hillary, and she said, you know, my brother could learn a few things from you. And I'd met her a few times and I'd met him,

but I didn't know him as well as I knew her. Would you be open to mentoring him? And of course, she hadn't asked him about this. And I said, sure. And partly she had read at that point, I think I'd written, I had written maybe, no, I hadn't written a book yet. But I'd written some columns, some business columns, and she just sort of knew who I was. So long story short is every Friday, Gavin would come down to my office in Union Square from his offices in Calhalla in San Francisco. And we'd sit down and talk. And then ultimately he had brought me into his Pump Jack organization to help mentor some of the other leaders there and lead some offsite retreats for them.

And then he ran for the board of supervisors in San Francisco. So he became on the board of supervisors, which is like the city council. And then he became mayor. And when he became mayor, that's where it amped up. Because now here's this guy who's, I don't know, at that point he was in his 30s, I think.

Pretty young, yeah. Yeah, he was in his late 30s when he became mayor, if I'm not mistaken, or early 40s. But he was a very young mayor and San Francisco was going through a really difficult time. And so now I showed up at his office every Friday. He was showing up at my office in the early days. Now I'm showing up at City Hall, room 200, and being his conciliary, I mean, I was sort of like the person he sought counsel from. And then he did the same thing.

So with his like chief of police and the fire chief and the head of human services, and we would actually do offsite retreats and I would help mentor some of them. And so that was a fascinating experience. And then he ultimately became governor and we still stay in touch pretty closely. It's a trip though.

Like you're like, what am I doing? I mean, mentoring the mayor. Well, it's weird. And it was like Chip, everybody in the office knew Chip brings Gavin's lunch and Chip's lunch in these sacks. And there's actually San Francisco Magazine once did a story about it. It was like this picture of me coming to Gavin's office

with a sack lunch. And so, I've been lucky enough to be the CEO for the Burning Man CEO, the mentor for the Burning Man CEO, Marion Goodell, Liz Lambert, one of the best known boutique hoteliers in the US and of course, Brian Chesky and others. What I love about mentorship is in a great mentorship relationship,

you as the mentor may learn as much as they will. And when I was at Airbnb, I had over a hundred mentees and over the course of seven and a half years, which is a lot. And I learned as much from them as they did from me. And Brian once said this to me, Brian Chesky once said this to me, he said, "'Chip, you teach me EQ and I teach you DQ,

EQ being emotional intelligence, DQ being digital intelligence." And I think if we could look at mentorship, we have five generations in the workplace for the very first time. And if we could realize, and here's a couple other stats, over 40% of Americans now have a boss that's younger than them. So my relationship with Brian was not as unusual as it might've been 25 years ago. So we have something to learn from each other and being able to create mutual mentorship

relationships where one person knows one thing that the other person wants to learn and vice versa, you know, it wouldn't take a lot of matchmaking technology in a large company to match employees as mentors. Because quite frankly, the beautiful thing about a mentorship relationship is it's free form, it's affordable, it doesn't cost anything. And bottom line is, Deloitte has shown in their studies that when people have a mentor in an organization, they're substantially more likely

to stay in the organization. And in an era like we're in right now with the great resignation where companies are saying, we're losing people left and right, one of the best things you could do, not just for wisdom and knowledge transfer, but also for retention is create mentorship programs within an organization.

There's great kinship between the idea of mentorship and the modern elder idea, right? Before we move off of this though, I think I'd like to hear a few thoughts on going about finding a mentor or soliciting your services as a mentor. I think there's a lot of people who think mentorship means I'm gonna email Seth Godin every single day for two years

until he finally relents and becomes my mentor. We think of these fancy names, people that we would like to have on call, but that's not really the heart of what it is. Like I'm always talking about the fact that there are mentors all around you, like find the people in your environment and figure out how you can contribute to their lives

if you're gonna solicit their input into yours. Yeah. And be careful of like leading with the M word, you know, like marriage. It's like, whoa. The M word, you know, if you pop the marriage question on the second date, it's a little too much.

I don't even know you. Yeah, exactly. So the way I would go about it on either side, mentor or mentee, but maybe let's start with the mentee side is let's say there's somebody you want to learn from. Just say, hey, could I take you out for coffee? Or could we go have tea? Or could I, like, can we just have a meal together? And if they're in your same organization, the likelihood is they're going to say yes. You know, if it's the CEO and you've been in the company a month as an intern, they may not say yes if it's a huge company.

But one of the ways to pose it is to say, hey, let's just have a little meal and I just would love to tap into your wisdom. I mean, don't be shy about saying something like that. Or even more specific, you say, I've noticed that you're really good at fill in the blank. I would like to learn from you. Can we just get together once and have a conversation? And then don't expect a bigger commitment than that, but then have the one time conversation. And if it goes really well,

and you can see that they're enjoying it as the mentor, say, in a month from now, could we maybe get together again? And they're likely to say, yes, do it again. And at that point, if that second one is great, then say, are you open to us maybe creating like a short-term mentor relationship? Maybe we get together once a month or every two weeks for an hour.

And I ask questions and you give me some homework assignments, et cetera. But at the point where you're ready to ask that, get specific about what you're looking for and be clear that you're committed to it. I mean, the worst experience for a mentor is when a mentee goes through that whole process and then doesn't take it seriously, doesn't show up for the meeting or says, okay, well, I don't have time right now or et cetera. Make the time. If you're not willing to make the time,

then don't actually make the ask. But also give it a finite period because that way the other person doesn't feel like, oh no, this is a lifelong commitment. The other thing I would just say is there's two kinds of mentorship. There's mentorship that's performance, what I would call performance-based

and then development-based. Performance-based is like finite. It's more of a mentorship relationship where you have information I want to learn. I need to ask you questions. And you'll be my mentor, but it'll be a finite relationship because I want to learn more about how to run a great meeting, how to understand the travel industry, how to, I don't know, code, do simple coding. So that's's finite relationship. It's performance driven in the sense that

over the course of a short period of time, you can determine if you've gotten better at that. So you can have a lot of mentees if they're sort of that like that. They're like, okay, yeah, you can ask me questions every once in a while. And I understand you wanna learn about this thing. The other kind of relationship

is a developmental relationship and it's a lot more comprehensive and it's more personal, professional, emotional, EQ. And that's when somebody really just wants a guide. You know, one of my mentees called me her confidant. And I said, wow, okay, give me some juicy gossip. And she said, well, no, no, a conf and she's French. She said, when I say confidant and I mean it in sort of the French way, you're the one who gives me confidence. So it wasn't a knowledge transfer. It wasn't a

knowledge transfer, which the first kind of relationship is like I'm transferring knowledge. The second kind of relationship is one that's more personal. And actually the person who's asking the questions is not the mentee. The person who's asking the questions is the mentor. And I'm asking questions about you to help you unlock who you are and help you, guide you, be your permissionary to help give you the permission to do the things I think that you

have the capability of doing. A lot of people think that that's what a mentorship relationship is, and it is. But this first kind is the more finite kind and allows you to have many relationships because it's specific to the knowledge transfer. So being able to understand what kind of relationship a person wants when it comes to mentorship is pretty important. Not to push back, but how many emails a day do you get from people asking to take you out for a cup of coffee? See, that's the thing.

It's nice to live in Baja most of the time because I'm not- I get a lot of those emails and it's just like, I can't do that. Like I'm not in a position to do that. So I think it is really about who are the people in your environment. Yeah, I mean, when it's, listen,

if someone has come from out of the blue and I don't know them at all, I mean, I do get a lot of emails from people and they, you know, they sweeten me up with all the things that they know I'll probably wanna hear. And in those kinds of cases, I'm not gonna get on a Zoom call with them, but I will answer two or three questions in an email.

I'll do that. And so for those of you who are listening to this now and you wanna send me an email with a couple of questions, feel free to do that because I had people who helped me early on. There are times when I may say, oh man, I am barraged right now. So I'm gonna have my assistant actually tell you

to write me back in a month or six months. And then maybe I can answer some questions. But most of the time I do answer questions by email pretty quickly, assuming they're really simple answers. But in terms of like someone saying, hey, can I get to do a quick Zoom call with you? It's like, I think one of the lessons we've learned

in the last two years is doing a simple Zoom call will wear you out if you do, you know, 12 of those in a row. And so for me, I also like to test somebody. You know, if I say, if someone comes to me and says, you know, they want some of my time and I'm really, really barraged with stuff right now and I can't give any time,

like come back to me in three months or six months. If they come back to me in three or six months and I can see that they've got something, I'll take it a little more seriously. Not because I didn't take them seriously the first time, but because they've shown me they have some reliability and some desire. Because they've shown me they have some reliability and some desire. And therefore I'm gonna try to reciprocate if I can.

I wanna talk about what it means to be a modern elder, defining what a modern elder is, but to kind of contextualize it, when I think of your tenure at Airbnb, coming in as a mentor, kind of emerging from that. When I think of your tenure at Airbnb, coming in as a mentor, kind of emerging from that as this modern elder and the success that that relationship engendered in terms of the company's prosperity,

it seems to me that that should be like a Harvard Business School case study. Maybe it is, I don't know. But because it was so fruitful and productive, why doesn't every company institute some version of that? Because it was so valuable. Well, the good news is the venture capital community and private equity community took notice

and it led to a lot of those companies sort of saying, how are we going to, the way venture capital and private equity works is often the person who's put in charge of the young CEO is a young partner or young associate at the venture capital and private equity firm. So they're not necessarily the person who has... It's not Bill Gurley.

It's not Bill Gurley. And it's not somebody who's really gonna have the wisdom or maybe the cojones, so to speak, to say to the person who's out of control, you're out of control. high profile, successful companies, they better have a gray hair in the midst and not just showing up once a month at a meeting, but actually creating a mentorship relationship. You're also seeing a lot more coaches being almost assigned to young CEOs such that the coach has that role.

Now, that's not a bad thing as well. Coaches can be spectacular. But often if the coach doesn't have the operating experience, they may not be able to keep up with the young CEO when they're talking about what's going on. Right, and this is pretty specific to kind of youth culture driven business, startup culture.

But in truth, like the Fortune 500, the Coca-Cola's, like these huge companies are the opposite. It's full of gray hairs. The whole C-suite is ancient. It's almost like they need a young mentor who will be taken seriously to say, here's why you're gonna be completely out of business in five years unless you listen to kind of

what my generation is looking for. Yeah, you're exactly right. Ageism works in both directions. A lot of times when we heard the word ageism, at least in my world, I think of like older people who are being discriminated against. It's the opposite as well. Young people being discriminated against

or not being given the opportunity to have a voice in organizations that could use some shaking up. So yeah, it definitely goes both ways. So, I mean, I think I would say that we're living in an era where this idea of an intergenerational potluck where we all bring to the table that which we do or know best makes a lot of sense. And there's a huge amount of research on this. So diversity often in companies doesn't think about age diversity.

We talk about race, gender, ethnicity, sexual orientation, but like, okay, age diversity is important as well. And there's a bunch of studies that have come out recently that have shown that when you create age diverse teams, you get the best of both worlds. You get that brilliance, that focus, that quick thinking, young spirit, along with the ability to metabolize or think holistically

and think beyond their own ego and actually create that psychological safety. Fascinating study Google did that showed that psychological safety was the number one ingredient of effective teams. And psychological safety is helped by having age diversity on a team. So I think we're in the early stages

of realizing that age is an important diversity metric, just like the other ones. Sure, for that to work and be productive, for that dynamic to be functional between older and younger, it does require a level of like respect and humility and the capacity to listen and take seriously what the other person is saying,

because I think both camps sort of look at each other as dum-dums, like, oh, these old people, they're checked out, they don't know what they're doing. These young people, their brains aren't even fully formed yet. Why should I listen to these people? Yeah, this is part of the reasons, I'm looking forward to doing something later this year.

I mean, I'll mention it now, but we don't even have a website up for it yet. But there's a guy named Michael Hebb who started Death Over Dinner. So it's a movement globally, over a million people have done this, where they have this Jeffersonian dinners, topics, conversations about the subject of death.

And you could have one of three or four or five different topics that you and a few friends can actually talk about over dinner. Well, I think generations over dinner. Generations over dinner is an idea whose time has come. I like that. Which means you bring a bunch of generations to like three generations, five generations,

maybe even seven generations. We have seven generations living still. Bring them to a table and have a topic about, how do you solve climate change? How do you address intergenerational collaboration in the workplace? What happens in the various life stages? And the wisdom would go in both directions. And you could sort of say,

oh, we just had a six generation dinner or we had a four generation dinner. And so it's something we're gonna be launching later this summer. We have a nonprofit called Age, the Association for Growth and Education that focuses on intergenerational collaboration. And so keep an eye out for that.

That's cool. I really like that. The generations over dinner. Yeah, I really like that idea. All right, let's talk about the Modern Elder Academy. So walk me through this epiphany and how you've created this amazing thing out of that idea. Yeah, you know, so I went down to Baja. So Southern Baja near Cabo San Lucas,

about an hour North, place called Todos Santos Pescadero area. I'm on the beach, I had a home there and I was gonna start writing my fifth book called Wisdom at Work, The Making of a Modern Elder. So as I'm writing that book, I'm going for runs on the beach. And one day I went for a run on the beach

and I had a Baja aha, I had an epiphany. As one is want to do. Yes, exactly. We are like, this is an area where there's a midwife for epiphanies. It's like something strange about this particular area that I live in. And the epiphany I had was this,

is that the word adolescence didn't exist in 1903. In 1904, it came into being because a psychologist named Stanley Hall created it and said, hey, there's a life stage that happens between puberty and 18. And it's, you're still a child, but you're on the threshold of adulthood. And you're going through emotional and physical and identity transitions. Okay. And then after 1904,

now we had public junior high schools and high schools more prevalent. You had child labor laws, you had people not getting married at age 14 and having babies when they're 15. So long story short is adolescence became a thing. Well, about 20 years ago, a new term got coined called middle essence. Middle essence is the adult corollary to adolescence. And it's when you're going through physical and hormonal and identity transitions,

often between around age 40 and 60. So the core of midlife. So I had this run and I came back. It's like, why do we not have any middle-essence school? We have adolescence. We give all this guidance and schools and tools and rites of passage and rituals for people in adolescence, but we have nothing for middle-essence.

And what if we were to create the world's first midlife wisdom school, a place where people come to cultivate and harvest their wisdom and reimagine and repurpose it. And so this was about four and a half years ago, I had the idea. We opened January, 2018, and we've had now 2,200 people from 33 countries

come do our programs, usually a week-long program in Baja, We've had now 2200 people from 33 countries come to our programs, usually a week long program in Baja, but we also have programs online as well. And the whole intent is to help people to sort of reframe their relationship with aging. And interestingly enough, the average age is 54, but 15%, 14% of the people who come are millennials. So this is not just people-

That's super interesting. Isn't it interesting that people in their 30s- And the motivation is, I just wanna be in a growth mindset and be thinking about this before it becomes a crisis. And I wanna start to mine my wisdom. And I also wanna be around people 20 years older than me to learn from their wisdom.

So yeah, and we have a great faculty. We have everybody from Paul Hawken, who's been on your show to Michael Franti, the musician, Matthew Ricard, the famous Buddhist monk, Sherry Lansing has done shows for us. John Donahoe, CEO of Nike is on our upcoming purpose online course. So lots of really interesting people who are helping people, helping all of us to reframe

that relationship with aging and look at how we might regenerate ourselves. Because the narrative we have about aging is you age, you work, then you retire. You have three stages in life. You learn till you're 20 or 25, you earn till you're 60 or 65, and then you retire till you die. And if you look at a millennial today, they're like, what the hell is that tyranny of the three-stage life?

I wanna actually work. I'm gonna learn till I'm 20 or 25, and then I'm gonna work for 10 years, and then I'm gonna take a year off. I'm gonna do a gap year. And then I'm gonna go get a master's. I'm gonna learn until I'm 20 or 25, and then I'm gonna work for 10 years and then I'm gonna take a year off. I'm gonna do a gap year. And then I'm gonna go get a master's. I'm gonna learn again. And then I'm gonna go retire.

I'm gonna work for 10 years and start a company and then retire and then go back and get a PhD. And it's more episodic. It's not like you have these three stages of life that are age defined. And so that led us, MEA becoming very popular and led us to creating regenerative communities

and these idea of, let's get rid of the idea of retirement communities. Yeah, this is the real exciting part. Rich, are you gonna live in a retirement community someday? It's the most depressing horrific aspect of our culture to just warehouse old people and hide them. It's a form of age apartheid.

Let's like take those people and put them in a place where we can't see them so they're with each other. And let's also recognize that frankly, earlier generations sort of saw it and our parents may have enjoyed it, but there's also this weird sense that, back in the old days, if you were working on the factory floor

or you were a school teacher your whole life, you got to 60 and you said, thank God I'm retiring because I can't do the factory floor work anymore or I'm just so tired of this work or being a house cleaner or whatever it was. And we have a lot more knowledge workers today. And I think we have a lot more wisdom workers.

That's a phrase that I think is gonna come into being. But the knowledge workers, they can work till their 70s or their 80s or whenever. It's not physical labor that actually defines how they get paid. And so more and more of them are of the mindset, like I don't wanna retire or I can't afford to retire. If I'm gonna live till 90 or 95, I can't retire at 62.

And also that generation is far more inclined to be pursuing work that has personal meaning to them than, you know, our legacy is that three chapter kind of approach to life. That's what our parents did. And we kind of were reared with that sensibility. And now we're in our fifties and sixties. And a lot of us are having those kind of crisis moments.

But over the course of those many decades leading up to it, there is a calcification around mindset. This is who I am. This is what I do. Here's what I can expect for my life. Here's how I see the world. This is the people that I vote for. And this is, you know,

these are the things that I talk about. So one of the critical kind of tools that you leverage at the Modern Elder Academy that I wanna hear a little bit more about is just getting really clear on what your mindset is so that you can begin the process of deconstructing it and perhaps telling yourself a new story. Yeah, well, so there's four key pillars of our curriculum.

The first one's reframing aging, helping people to see that maybe their best years are ahead of them. Can this be aspirational? It can be, and some things get better with age. I love that your listeners and your community is very much about keeping the body alive. But certain things get actually better with age.

Your emotion, your emotional intelligence grows with age. Your spiritual awareness grows with age. So there's a lot of things that actually get better with age. And yes, if you work on your body and your health and your nutrition, it might get better with age as well. You're a great example of that. So there's that, reframing aging.

Then there's mindset. So there's growth and fixed mindset. We're big fans of Carol Dweck's work at Stanford. And so a fixed mindset is when you tend to think of life as I'm here to prove myself and I define success as winning. The problem if you have that point of view as you get older is you stop playing the games you can't win. And that means your sandbox gets smaller and smaller.

And as it gets smaller, you actually get more bored because you're not trying new things. So moving from a fixed to a growth mindset means moving from proving yourself to improving yourself. And instead of focusing on winning, you focus on learning. And so you move into this way of thinking and way of being of, okay, I am just a learning machine. I'm not a machine, I'm a learning human. One of the questions we ask at MEA is, what is it that you know now or have you done now that you wish you'd known or done 10 years ago?

Think about that for a moment. And then ask yourself 10 years from now, what will you regret if you don't learn it or do it now? And this is how I started to learn how to surf at age 57. Because I live on a beach near a surf break, somewhat famous one. And I was like, ain't gonna be any easier at 67 than 57, Chip. So I got to start learning that.

I also started learning Spanish. Again, the mantra in my head, the mindset was, I'm too old for this, too old to learn the language, but harder to learn at 67 than 57. And I knew that I was going to be living in Mexico. So why not learn it? So the first is reframing aging. The second is shifting your mindset.

The third is learning about transitions. None of us were taught and got a master's in TQ, transitional intelligence, but midlife is full of transitions. Life is full of transitions. Life is liminal. You're usually in between two things. And yet we've never really been taught,

what's the anatomy of a transition and how do I architect moving through a transition, whether it's getting divorced or changing where I live or changing my career or retiring or seeing my parents to passing away or becoming an empty nester or going through menopause or men go through andropause. There's a lot of transitions in midlife. And learning how to understand the three stages of a transition is a big part of our program. And then the final piece of the curriculum is regeneration

in all its forms. We have regenerative cell therapy. I mean, stem cell work, regeneration through understanding a regenerative purpose, but also, and this is where Paul Hawking comes in, regenerative agriculture and farming. And that's what leads us to our regenerative communities. Our first one being in Baja with 26 homes around a regenerative farm. So instead of living on a fairway, wouldn't you like to live on a farm and go out into the farm

and go harvest with your neighbors and do a potluck once a week? And so now we're taking this to Santa Fe and we have three different properties in Santa Fe, two of which will be academies, one of which will be a regenerative residential community. And I do believe that we are creating something that is meant to disrupt senior living. Right, it disrupts higher education, some form of education,

and then this whole kind of area that's so ripe for disruption, senior living. But it's leveraging all this experience that you had as a hotelier. Like it's not that dissimilar, like, oh, I'm gonna disrupt the hotel industry. I understand that skillset. Now I'm gonna apply it to this other area

that desperately we need something better and healthier. I think that's really exciting. Lucky to be a disruptor twice in the hospitality industry, first as a boutique hotelier and then at Airbnb. But you don't start something to disrupt it. I mean, that's not the intent. You start something because you have an idea. It's a natural outgrowth of everything.

That's right, you have an idea and then the idea sort of takes off. And then we hear from people saying, Chip, long life learning, that's what you're doing. You're not doing lifelong learning, you're doing long life learning. And more and more colleges and universities who are in the process of being disrupted in all kinds of ways right now,

Clay Christensen, the guy who created the term disruptive innovation before he passed away five years ago said, 50% of the colleges and universities in the United States will be out of business in 10 to 15 years. So colleges and universities need to start thinking about midlife wisdom schools or these places. And to be fair, a lot of colleges have programs, but it's sort of traditional curriculum oriented. It's accumulating knowledge. It's more like I'm going- It's not experiential.

I'm a 50 year old sitting in a classroom of 20 year olds and I'm learning biology or I'm learning philosophy. But it actually isn't, I wrote a white paper called The Emergence of Long Life Learning to study with a PhD who wrote it with me. How do people learn differently at 55? What's important to them?

How do they learn differently? And that actually had a huge impact on how we have created our curriculum because we actually at MEA, wisdom is not taught, it's shared. So how do you create the crucible for a collection of 20 people over the course of a week to learn a bunch of things,

but then actually share experience and in small dyad partners one-on-one with each other, have these conversations of how it's applicable to them. And how it's gonna be applicable to you at 55 or at 45 is different than it is at 25. So yes, lifelong learning is a thing, but long life learning is a subset of it focused on how to live a life

that's as deep and meaningful as it is long, because we have gotten the quantity right. Longevity has grown a lot. The quality is the thing that I think people need to focus more on. A big piece in trying to engender your life with that level of quality is this transition that you speak about from accumulation to attunement.

So speak about that a little bit. Yeah, the first half of our life is about accumulating, accumulating knowledge and friends and obligations and romantic partners and then marriage possibly life is about accumulating, accumulating knowledge and friends and obligations and, you know, romantic partners and then marriage possibly and children. You get to age 45 or so and you say, oh my God, I've got this burden. I've got like, I've got a lot of baggage. And the second half of your life is now about editing that baggage. So you move from accumulating to editing and you move from the attainment part of your life.

And it doesn't mean you don't have attainment throughout your life, you do. But I gotta tell you, and as someone who's like a first class attainer, your attainment at some point, as your ego starts to shift, that operating system of the ego shifts to the soul, you move from attaining to attuning. What's the difference?

Attaining, when you're in the attainment mode, you will atone later because you may have sharp elbows. You're sort of like, when you're actually attaining, you're very selfishly focused. And you might be a gracious person, but you're deeply focused on the finish line. And that's the hedonic treadmill. It's when we sort of realized, man,

I keep putting finish lines there and I feel a sense of accomplishment, but I don't necessarily feel the sense of happiness. And so moving from attainment to attunement moves from atoning afterwards to feeling at one. So when you're in the attune phase, you're sort of like harmonizing. So surfing is an attunement sport.

You better attune with the wave. So many things as we get older become attunement, opportunities for attunement. And as we learn how to attune, we actually know how to create sort of that psychological safety in a team. We know how to actually create what's called environmental mastery.

This is something we get better at as we get older. It's not about the ecosystem or the dirt on the ground. Environmental mastery means you actually know how to repot yourself in the right habitats and flourish. It's a psychological quality. It's a social science research that shows that as we get older, we understand where we will flourish. It's a psychological quality. It's a social science research that shows that as we get older, we understand where we will flourish and you are better and more adept at being able to discern where that will be. And so that becomes a part of it as well. And that's

attuning with the right environment. It's part of the reason why, frankly, at age 50, we sort of get to a place where like, I have no more fucks to give. And I'm not talking about someone's romantic life. I'm actually talking about, I don't wanna be in an environment that it feels toxic to me. You might handle it in your 20s or your 30s,

maybe even your 40s, but in your 50s, your level of patience for it isn't the same. And one person's toxicity may be another person's beautiful environment. So I'm not saying all environment- Right, but there's a freedom and like kind of a liberation and a strength in that. Yeah.

If you're looking at it correctly. Yeah, I think it's this self-awareness that comes to like, I know where I flourish. I know what I like. And that's the editing function. But also, sorry to interrupt, but making sure that that is coming from a higher consciousness state

rather than an outgrowth of your fixed mindset at that time about your capabilities. Yeah. It's having that openness again, to the intuition, to the wisdom, to something that actually may emerge that is not scripted for you. And that's actually frankly why in the great resignation in the pandemic, we've seen an enormous explosion in people 45 and older going out and starting their own business. Yeah. It's huge. And a lot of young people not going back to the job.

And a lot of young people not going back to the job. And confusion, like what? Like people are confused that that's occurring. That's right. But what I find interesting on the 45 year olds and up is we tend to think of it like all the entrepreneurs, like the hot entrepreneurs are under 30, but the fastest growing set of entrepreneurs in the country today are 45 and older. Is that right? Yeah. Yeah, exactly. And so over 50% of the businesses, you know,

the new businesses started in the U S are people 50 and older. So. Yeah. I love that idea of attunement. Like in retrospect, reflecting back on my life, like so much of everything that I'm so blessed to be able to do now has been a process of trying to focus on attunement, having that kind of crisis with what I was doing, you know, relatively early, like everybody thinks of 40 as like this pivotal kind of life crisis.

And now it just feels cute. Like I'm 55, I'm like 40, you were so young. And to kind of inelegantly, but eventually fall into this vocation that I feel like meets my skillsets, allows me to continue to develop this growth mindset and is successful only to the extent to which I can be attuned with you.

Like I can't achieve this conversation for it to be valuable or successful for the person who's listening to it. That is truly a function of the extent to which I can be prepared, but yet completely present and in the allowing. So the opposite of presence is absence. And we live in an absent culture partly because

we all have an iPhone in our hand. And when you meet someone who has presence, whether it's a mentor, whether it's a teacher, whether it's a friend, whether it's a romantic partner, when they are present in the moment, you notice it. And this is a quality we get better at as we age. I mean, actually we're very present when we're young. So we're very present. You know, you notice it. And this is a quality we get better at as we age. I mean, actually, we're very present when we're young. So we're very present. You see a child, a two-year-old or a one-year-old sort of just looking at things and there's a presence there. And then we accumulate knowledge as we get older and in our childhood, and we have scripts that we're living and we're less present. And there's a point at which we become present again.

I happen to think it's around when the operating system of the soul kicks in. And when we start to become present again, things come through us. So I was most of my life, a can do it person, can do it. We had 3,500 employees at Joie de Vivre and I handed out 3,500 copies of the book, the little engine that could.

The little engine that could. You remember that childhood story? Yes. So the childhood story of this little tiny little, not a caboose, but the train at the start of the, what would you call the first train? I don't know. The engine?

The engine, thank you. Yeah, it's a little engine that could. Thank you, Rich. I know this story. It's so imprinted into my childhood. So the little engine that could was sort of brought into duty to do something that was beyond what it thought it could do

and bring all those animals, the circus or zoo animals up a mountain. So the can-do-it attitude was very much in my brain. And it was like something I wanted all of my employees to have. And we saw that in terms of guest loyalty, a guest who felt that the employees had a can-do-it attitude, that was the number one correlation with whether the guest would be loyal. Can do it, can do it, can do it. I have moved from can do it to conduit. So can do it is attainment.

Can do it is I can do it. Can do it is rugged individualism. It is the ego run riot. And it has wonderful qualities about it. But there's a point at which can do it when it can shift to conduit, what happens is you're now the channel. You are the present one who's channeling something through you.

And whether this, if Julie was here right now, she'd probably be, we'd get into a very deep spiritual conversation about this, but it is your ability to be the channel, the conduit of things through you. And when you get to that state, there's a power that you are conducting that is so much greater than anything you can do

in the conduit stage. And all of this sounds very ethereal, but you know it when you see it and you feel it. Sort of like pornography. Definition of pornography from the Supreme Court was, you know, you know it when you see it. Presence and someone's power as a conduit, you know it when you see it.

And I guess I would just say that it's that level of energy. Someone said to me, you've written a book, Chip, about wisdom at work and all these older people are going to come to you and say, how can I get a job in my 50s or my 40s or my 60s? And this executive recruiter said something that was so beautiful and it relates to this. She said, if you show up with curiosity and passionate engagement in your interview, whether it's in Zoom or in person, what people will notice is not your wrinkles, but they'll notice your energy. And when they notice your energy, they lose track of your age. And that is so true. I mean, I'm feeling it right now as I'm speaking to you, you're feeling it from me probably.

Yeah, it's really powerful. I mean, I'm feeling it right now as I'm speaking to you, you're feeling it from me probably. Yeah, it's really powerful. There's an energy. And when someone is, an energy is something that's coming through you. It's not just how much weight you're lifting, but it could be.

I mean, the conduit can come through you in all kinds of ways. But for me, it comes through me in this role as a teacher now, but also a learner. And I love being in an environment where I can look back and say, I lost five friends to suicide between 2008 and 2010. I wish there had been a great midlife wisdom school and a place where they could have done a great midlife edit such that they could still be on the planet. And that's what's coming through me.

Yeah, the conduit. There's something really beautiful about that, that also, I've just noticed when I can inhabit that space to the extent that I'm capable, that is so much more fulfilling than the striving and the accumulating. Yeah. To be this channel for somebody else's success or to be the connective tissue between two things

that then become greater than the sum of their parts. Yeah, there's a guy named Eric Erickson, developmental psychologist. And he said five words that just to me define this era of life. He said, I am what survives me. And that really means a lot because it suggests that we've moved to an era of your life where generativity is the key.

He also said in our midlife and later years, the challenge is between generativity and stagnation. But generativity is different than attainment. Generativity means you're creatively generating things, but it's for other people. Often he meant it in the term of generations for other generations. So how do we co-generate? How do we create things that are gonna survive us

that are gonna support other people and help them be a better version of themselves and maybe a better version of me, I mean, through them. So yeah, I mean, again, this is very much the mentorship language, but I think one of the things that people need to think about as they get older is their legacy and not the legacy, the ego legacy. It's not so much, how am I going to be remembered? That's important, but that has a certain ego attached. It's more, how will I have served?

And when the shift can go to, how have I served? There's something in it that speaks to what am I doing that's going to live beyond me that is gonna have an influence way beyond me sitting here. Yeah, well, I think that's a good place to kind of lead into the last thing that I wanna talk to you about, which is for that person who is contemplating all of this right now, perhaps

they're in their forties or their fifties, and they're thinking about what's next, or if there is even going to be anything next. And, you know, maybe doesn't have that level of, of self understanding or self-integration to really, you know, have the intuition to, to, you know, follow, you know, wherever they're being led by their curiosity. And perhaps they don't have the budget to go down to Baja and participate in your academy. What are some things that they could be thinking about, perhaps books they could be reading

or ways of approaching that level of self-inquiry that could help unlock some of those answers? Lots of great books out there. Wisdom at Work. Wisdom at Work being one of them. But The Hundred Year Life is a really interesting book written by two UK academics. Talking about the medical world says that children being born today,

there's a 50% chance they're gonna live to 100. So how would you curate your life differently if you knew you were gonna live to 100? So how would you curate your life differently if you knew you were gonna live to 100? So it's a great book. There's, gosh, what other books do I love? Let me just, let me, you know, when you mentioned that something comes to mind, which is another tension, the tension between,

yes, let's contemplate our lives at 100 and how we can plan for that. But how do you like sort of reconcile that with another powerful idea, which is, what if you don't have, what if you only have three months or six months or a year to live? How would that change how you're approaching

the way that you spend your time? Well, that's a very different question. So Laura Carstensen, I'm on her advisory board at the Stanford Center on Longevity. And she's done very conclusive research on this to show that the shorter period of time you have in your life, the more you take seriously each moment and makes sense.

And she looked at it with older people, but also people who had AIDS, people who had a cancer diagnosis that was incurable. And what they found was that when you have less time, you are more mindful in the moment. And that makes sense. You're less focused on the past. You're less focused on the future.

You're more focused on the moment. And what comes from that is a certain level of life satisfaction and contentment. And so that is, I would just say for anybody who's looking at their life right now and saying, I don't feel very content, my response to them would be, how much are you spending time in the moment?

How can you do that? Yes, you can meditate. Yes, you can do yoga. Go for a walk with your dog in nature. So during the pandemic, when I was living in Baja and we had no guests because we had to shut down, I would do, I put on my calendar three hours a day, three days a week, and I called it spying on the divine.

And I would go get divinely intoxicated in nature. And I don't mean I brought alcohol or psychedelics. No, I was going for a walk with my dog for three hours in different natural, beautiful places around Baja and just noticing what nature could teach me. The resilience of nature, the interdependence of nature. I was being in the moment. And our friend Dacher Keltner,

who started the Greater Good Science Center at UC Berkeley and is on our faculty I was being in the moment and our friend Dacher Keltner who started the greater good science center at UC Berkeley and is on our faculty and has a book coming out on awe next year. It talks about the various forms of how you can find awe in your life. And for so many people it's found in nature. So I'd say that is something you can do. You've got a park near you.

You've got, I mean, you don't have to spend any money on that. You don't even have to park near you. You don't have to spend any money on that. You don't even have to, you know, you don't have to buy a book for that. But there's lots of other good books. There's, you know, from strength to strength that just came out with Arthur Brooks. There's Becca Levy's book, breaking the age code. Becca Levy is the one who actually,

in many ways our program is built on her work from Yale. She was able to show that when you shift a person from a negative to a positive mindset on aging, you give them 7.5 additional years of life. What? It's actually more life than if someone stopped smoking at age 50, or if they started exercising at age 50. So the public health benefit of shifting a mindset

around aging has a greater benefit to society and people are happier. And yet we have PSAs left and right about how we should stop smoking and how we should start exercising. We have no PSAs around how to reframe aging. So there's her book, "'Breaking the Age Code,"

which just came out in the last month is a great book. You could do MEA online. I mean, it's our purpose course starts in June and that is not very expensive and it's eight week course. But there's lots of ways that for people to actually ask themselves. My blog, my daily blog's free, WisdomWell. It's really sort of the best of MA curriculum.

Get a micro dose of wisdom every morning. Yeah, and maybe adopt that weekly inventory journaling practice. Oh yes, the My Wisdom book, exactly. Yeah, beautiful man. Thank you. Really inspiring to talk to you. Yeah. I wanna come down and visit you in Baja.

Maybe we could co-lead a week. That would be great. I would love that. I would love that. I need more Chip Conley in my life. If I get anything out of this, like yes. You're helpful for me because you know, it's funny, last quick thought.

I'm not vegan, but I started a vegan restaurant. That's right, we didn't even talk about that. Like I had no idea that you were co-owner of Millennium. That's the legendary, I thought Robin Williams owned it at some point. No, no, no, no, Robin Williams went to a lot. He used to go there a lot. He went to a lot, Woody Harrelson went to a lot.

A lot of people went there. By the way, have you seen the movie, the show, Bad Vegan? Yes, that's a whole other podcast. Oh my God. I used to go to that that Pure Food all the time. I did too. So long story short is you are a reminder for me because of your show and your presence

about me taking care of my body. Because I had prostate cancer and I am back in- How are you doing? I had a surgery that I only have half a prostate now, but my PSA is below one and it was 10.8. So life is a lot better. And you're that reminder of take care of myself. All right, well, if I could be so audacious,

I will consider this the first installment in an ongoing conversation. Beautiful. I'd love to have you back. So thank you, Chip. Thank you, Rich. Appreciate you. Peace. We did it.

Yay! That's it for today. Thank you for listening. I truly hope you enjoyed the conversation. To learn more about today's guest, including links and resources related to everything discussed today, visit the episode page at richroll.com

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