Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA)

0:00 Let's paint a picture of just what it was like to join Airbnb in your fifties. I was mentoring Brian, but he was also my boss. I was 52, the average age was 26. I had to be both wise and curious, and often the dumbest person in the room. So it's great to be in founder mode. It's not as great to be working for someone in founder mode. Brian assumed everybody else. Pace and duration. His point of view is like hey, we're having a meeting in the office tonight at ten o'clock. You know, be there. I just said listen, let's get some older people who are hosts in here. This whole Story is a really good example of the value of having folks that are older. When you have older brains connecting the dots, younger team members being really fast and focused, it's brilliant. And people won't notice your wrinkles as much as they'll notice your energy. The Airbnb experience led you to starting something called the modern Elder Academy. So if you think about the caterpillar to butterfly journey, midlife is the Chrysalis. Midlife is not crisis. I'm happier today at 64 than I was at 47 when I was going through my flatline experience. Well let's back up a little bit. This near death experience.

1:13 Today, my guest is Chip Connolly. Chip is one of the most extraordinary and interesting people that you'll ever meet. He was a founding member of the board of Burning Man. He's on the board of the Esselent Institute in Big Sur. At twenty six, he started a hotel chain called Jwadaviv. Which went on to become the second largest boutique hotel chain in the US. After selling it, Brian Chesky personally recruit Chip to join Airbnb to help Brian and the company transform from a fast growing startup to the world's most valuable hospitality brand.

1:41 After leaving Airbnb, where he was known as the Modern Elder, Chip started the Modern Elder Academy, now known as MEA, the world's first midlife wisdom school, with large, sprawling, beautiful campuses in Baja and Santa Fe. He's also written seven books, given a TED talk, and is just a genuinely interesting and amazing human and friend. In our conversation, we explore how to be successful in tech as you age. What he's learned working with and for Brian Chesky, including a lot of real talk. How to build a great culture at your company, his near death experience, and how it changed the trajectory of his life.

2:16 and so much more. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of a bunch of incredible products, including Replit, Lovable, Bolt, N8N, Linear, Superhuman, D Script, Whisperflow, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, JetPRD Mobbing, and more. Check it out at Lenny's Newsletter dot com and click bundle. With that. I bring you

2:41 Chip. Connolly. This episode is brought to you by Great Question, the all in one UX research platform loved by teams at Brex, Canva, Intuit, and more. One of the most common things I hear from PMs and founders that I talk to is I know I should be speaking to customers more, but I just don't have the time or the tools. That's exactly the gap Great Question fills. Great Question makes it easy for anyone on your team, not just researchers, to recruit participants, run interviews, send surveys, test prototypes, and then share it all with powerful video clips.

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4:27 That's V A N T A dot com slash Lenny. Thank you so much for being here and welcome to the podcast. Oh my god, Lenny, I I sort of feel like I'm your father who's so proud of his son. It's done you s my son has done so well and I I like to talk about

4:47 Tell my friends about you. Wow. Uh I am honored. Uh I'm happy that I'm making you proud, Chief. And I feel I feel the same in reverse. Uh, we got to work together for many years. It rb. I got to learn a ton from you. Uh, I'm really excited that more people are gonna get to learn from you from this conversation.

5:04 I'm thinking that the way that we break up this conversation is kind of break it up into three parts, which are kind of the three arcs of your career. And the three parts are your uh early career building Your time at R B where we got to work together. And then talking through what you're working on now, the modern elder academy. I actually want to start with the middle chapter. I'm gonna talk about Airbnb, where we got to work together.

5:27 Let's paint a picture of just what it was like for you to join Airbnb in your fifties. Uh Surrounded by A bunch of twenty something, thirty somethings reporting to Brian Chesky, who is I don't know, in his thirties. What was that like? So yeah, I I

5:43 wasn't planning on doing this. I I got a call uh from a woman named Natalie Tucci who worked at Airbnb and said I we uh Brian Chesky and I have been talking about Having you come in and give a talk. Are you open to that? And I was like Well What is Airbnb?

6:00 This was uh thirteen years ago. This was I think it was the end of 2012. And then Brian called me and said, Listen, I we really want you to come in. And so I came in and gave a talk about the innovation in hospitality and And I think I I didn't realize it was sort of a a a dress rehearsal for Brian to sort of see whether

6:21 the younger crowd there, um I was fifty two, the average age was twenty six. would, you know, feel good about you know, uh an old geezer like me with a bricks and mortar Boutique Hotel.

6:34 uh talking about the industry that Airbnb was disrupting. Um and as it turns out, people liked me. And um so Uh, Brian said, I want you to come in for and work fifteen hours a week. Uh, as a consultant, I want you to be my in-house mentor for both me and Joe and and Nate. And I said, Okay, you know, fifteen hours a week is great. And then uh within three weeks it was fifteen hours a day.

7:00 And Brian and I was saying to Brian, you know You're actually not paying me anything. Um you gave me s uh a little bit of stock that would would vest in six months and I said like I don't know th that this deal's working for me. Um this is you you n It seems like the company needs to be a little more than

7:18 You said and And he said, Yeah, I gotcha. I just wanted you to get in here and see like what you could do and Long story short is I ended up going full time and um It was hard at first, uh Lenny, because I didn't understand the tech lingo. I

7:38 I didn't have any background. I was fifty two. I'd never worked in a tech company before. I was mentoring Brian on leadership, but he was also my boss. I was the um head of global hospitality and strategy. Uh so which meant uh meant Initially I was in charge of all the hosts in the world. Over time that would like you know, that meant a lot more things too. I I was involved in

8:00 Mo many parts of the business. Definitely not the technical parts. But I think the hardest thing for me is was just that initially When people were talking about product. And Joe Bot said, you know, I'm the chief product officer and I'm like, Well isn't the product Isn't the product the homes and the apartments?

8:18 And Joe Bat said no product in the tech industry is something different. And so I had to be both wise and curious. And often The dumbest person in the room. And that was uh it required me to have a certain amount of humility.

8:32 As well as to be reporting to a guy twenty one years younger than me, Brian. That actually the point you're making there about what is the product, I I asked uh Laura Hughes, formerly Laura Modi, what to talk to you about. who we got to work together. She's the CO of Bobby now. Uh you work closely with her at Airbnb and she said this was the thing that stuck with her most about working with you is coming in and and everyone's talking about we gotta make the product better, we gotta

8:55 Optimize this button and improve conversion and Product, product, product, and you're just like What is Like, what is the product? I thought the product of Airbnb was the hosts and the experiences and the trips, and I think that shows the value of someone Like you coming in with

9:09 Different experience and also older. Yeah, and helping us communicate differently to hosts who also don't understand. Well, there's an interesting thing also, Lenny, and you you know this th the difference in age between our hosts and our guests was probably about ten years, maybe, and over time it actually got higher um because we started actually reaching out more uh aggressively to you know boomers and and gen Xers. To be hosts and

9:34 So you had I remember one point, um, and again let's get into product talk here. I remember one point the There was a conversation that was going on. About taking Airbnb so it was mobile only. Um I mean because

9:49 Back in the day. The two sharing economy darlings were Uber and Airbnb. And of course Uber was pretty much a mobile only app and Airbnb started as non mobile and then went mobile and then I was like, Oh, wouldn't it be interesting if everything was mobile.

10:05 And at some point I just said, Listen Let's get some older people who are host in here to see how well they will be versed in in in managing their listing. purely on mobile. And So there were times where I was a voice for

10:21 Older uh users in in this case hosts. Um That was helpful. to you know guy guys and women in their twenties

10:30 were the engineers and designers and product managers and um I always liked working with you. I want to just compliment Lenny, um for a minute. And we did a lot you know, we were we did a lot of different things together and What I appreciated was you

10:45 You had a humility to you. There was different than a lot of the other product managers. There's other product managers I'm not gonna mention their names and there some of these some of these w Product managers were very good. There were other product managers, though, who I found it sometimes hard to work with because They expected me to know as much as they did.

11:06 And You know, I guess it would be the if the opposite side of that would be um an older manager expecting a younger manager to have as much emotional intelligence because emotional intelligence On average is something we get better at as we get older. So I think the key for me to work in that environment and make it work.

11:26 was to not pretend to know things they didn't know. It was to have a sense of humor and humility. And how I operated And it was to show respect and hope that I got it in return. And I don't know if th you felt that way, Lenny. I you know, that's that's the tr the kind of environment I tried to to

11:44 Embody there. Absolutely. There's a couple of threads there. I wanna follow one is just Working For Brian.

11:51 A lot of people talk about founder mode and the power of founder mode. It's so great. That's how we do it. And guess guess who like you know populated with that recently? That was Brian. Exactly. Uh So it's great to be in founder mode. It's not not as great to be working for someone in founder mode. Often a very challenging place to be. Yes. You you report it to Brian. Uh Also, you were just your own boss basically your entire career. You never really

12:14 Have to report to someone before Also he was in his thirties, you're in your fifties. What was it like working for Brian? Uh, you know, like the more real you can be, the better, because a lot of people always talk about here is like I was wonderful, I learned so much. Just like what was that experience like? What did you learn from working for someone like Brian? Well let's start with the fact that it

12:32 I would never have gone to work for Airbnb. If I didn't believe in Brian. Because quite frankly, when Brian approached me and we started talking about I was like I wasn't sure I liked the I the business model all that well as a hotelier. So I had to believe in something beyond the business model because I wasn't sure that this amount the business model would work. Although Soon after joining I saw the numbers, I was like, Wow, this is working pretty well.

12:55 But I believed in Brian because the thing that Brian showed up with initially was just a curiosity and an appetite for learning. You know, I remember back in two thousand eleven when the you know, the big debacle happened with um the the apartment getting uh trashed by a guest and

13:14 And so Brian decided he was gonna go to find, you know, George Tennant for the The former head of the CIA. And so like Jo Brian would go to experts and and say to the expert, I don't know what the hell I'm doing.

13:27 And um He did that with me when it came to hospitality. So I appreciated that a guy who had a lot of hubris and Brian definitely has a lot of hubris could also have the humility to to say I want to learn more about this.

13:42 So it's sort of a growth mindset. What was hard with Brian is And say three things. Um number one is Brian assumed everybody else was going to work at the same

13:55 Pace. And Duration. You know and he still has this issue. I mean The beautiful thing about Brian is he's been very honest in the last couple of years on podcasts.

14:05 About His workaholism. And about the fact that the way he lives his life is not like other people. But back when I joined You know, his point of view is like, Hey, we're having a meeting in the in the office tonight at ten o'clock.

14:19 You know, be there. No, I don't I don't think so, but so I so I think the the the fact that Brian assumed everybody else W was as one dimensional in their focus as him was at times a problem. Especially for a guy like me who was I was at a stage in my career where like I have a lot of interests. Um

14:41 So that was one. Number two is Brian. Admires and admired in back then stief jobs so much That There was a sense

14:53 that as A guy who came from the product world. Uh from the Rhode Island School of Design. He knew better than anybody else. And so

15:05 There was a You know, one of the challenges for a CEO sometimes, and I ha this was my experience in my twenty four years of running You want to leave my boutique cartel company. Is it feels good when you feel needed. Um and

15:18 To come into a room and sort of see something and then point out the things that are wrong. Makes you feel good. Uh and If you don't have emotional intelligence, you can that process can really piss people off or or demotive demotivate people.

15:36 And In Brian's case, I didn't have to deal with that too much. Because he didn't understand it when I was starting, it was really I was in charge of the hosts around the world. And so quite frankly The idea of what's the psychology of the host. What's a host entrepreneur like?

15:51 I went on a world tour to twenty different cities and r went and talked to hosts. And I think I came back from that with a little bit of credibility with Brian to say like hey You know, I yes our data science team and the quality folks who are who are doing qualitative interviews, they're getting something out of this. But I actually went into the homes of these hosts. in all around the world and

16:13 And I think I I was lucky because Brian did less of that than he did with other people. But he for the for the product team, my God, I mean a a product meeting with Brian. would keep people up the night before. Uh not just because they were actually working all night long to get prepared. But also the they knew they were working all night long because they probably wouldn't sleep in anticipation for this. So that's a that was another issue for I I'd say. Um It's the other thing that you know, it that and in in each of these cases I think Brian's getting better.

16:44 So just like Steve Jobs got better over time when he left. And then he came back, he was much better when he came back. From all the people I've talked with who worked with them. I say the third thing for Brian was The sens

16:58 that adding a zero to something in terms of expectations or Thinking you you're gonna set a deadline. That is Unreasonable. Is

17:11 necessary because if you don't do that, there's an almost an underlying message. That People won't kick ass on their own. So there was a sens that Brian had that he had to Maybe create ridiculous goals.

17:28 Because even if we hit half of that goal. It was very encouraging. What he missed in that. was the fact that When you miss a goal.

17:38 And when you have someone who has power over you setting the goal or Encouraging a particular goal. You're setting people up for You know, a a lot of stress. And so

17:51 At the end of the day, I think Brian is an A you know a generational leader for uh as a millennial. Um, and I think he deserves a lot of credit and the Airbnb. Із а сусфоліз партнек. Of Brian's leadership and I would not have been there without him.

18:08 Having said that I had to hold my tongue in meetings sometimes. When I saw how he was operating. Because I wouldn't have done it that way. And I think over time, I hope I had a little bit of influence on him in terms of how to apply some emotional intelligence.

18:26 Uh to leading people. For people in this position, a lot of people work for founders, especially now that founder mo is it a thing. Every founder is just like I'm the founder. You gotta do what I tell you. It's founder mode. We're gonna this is how we win. We're in founder mode. You shared really good insight of building credibility.

18:43 That's a really good Clever. to work. Better with someone like that.

18:48 Uh Tactics to be effective with founders and founder but So he if I knowing what I know now, I would say Lenny Let's let's do a little pep talk, you and me before the meeting. I want you to start the meeting with the following

19:01 Uh as as you present and Brian's in the room. So Brian, let's talk about What we're trying to accomplish here. Let's get really clear. And you probably did this. But let's get really clear on what

19:14 Um both what's the intention of This iteration we're doing on the product. Like what Define success. And what do I wanna get accomplished in this meeting? And you start with that.

19:27 Because That actually helps to make sure there's alignment. And frankly, if there's not alignment. You might as well not have the meeting. What's it

19:36 Spend the rest of this meeting talking about alignment. That's what I would do. Because That's something you can come back to over and over again. During the rest of the meeting.

19:44 When Brian or the founder, whomever it is is beating you up on something and saying like well let me tell you why it looks like that or why we're doing that. It goes back to that, you know, the three principles or the three key goals we're we're trying to do. With this product update.

20:00 And um Yeah. So So set try to set alignment on the front end. That's a that's an important tip for anyone working with anyone even. So I love I love just that that works especially well here.

20:12 And then just going back to the credibility piece, I What you should there is you went on the World tour, not something everyone can do, but just Like Getting really close to your customers.

20:21 And using that as a hey, I actually know what I'm talking about. You actually should listen to me, even though you're the founder. Yeah, and don't I mean I think the other thing is um PowerPoint or whatever whatever tool you're using. I mean, like just be careful about being overly reliant upon it. It just It's Especially when you have

20:42 a combustible founder. Who May take you off path. Such that your deck in the current order makes no sense at all.

20:52 So that's I always wanted to really limit the deck as much as possible. Because I didn't know where the meeting was gonna go. And I wanted The deck's helpful at the start, at the very start.

21:04 To just sort of set principles, set goals. Um But yeah. So this whole story of you joining Airbnb in your fifties It is a really good example of

21:14 of uh cros intergenerational collaboration, something that you're big on, just the value of having folks that are older working at tech companies. Maybe just talk about that broadly and w then we segue into other elements of your career. I wrote a book called Wisdom at Work, The Making of a Modern Elder after my Airbnb experience. And um I did a lot of research. I was like, wow. So why do we have

21:38 less intergenerational collaboration in the workplace, especially in Silicon Valley than we could We could use And I started interviewing people, then I started talking to brain scientists, neuroscientists and Realize that a younger brain has fluid intelligence, tends to be fast and focused, really good at problem solving. Uh, very good at linearity in terms of looking at things.

21:59 As you get older, the brain shrin a little bit. And You have crystallized intelligence. And in in crystalized intelligence what's going on is Your brain you're going from left brain to right brain more adeptly. You're there's a little bit less focus, a little more holistic thinking, systemic thinking, connecting the dots.

22:17 So you can imagine that on a team. In a you know, when you have Older brains connecting the dots, thinking broadly, peripherally. Younger team members. being really fast and focused.

22:29 and being able to think linearly how to get things done. That combination can either be successful or not. When it's successful, it's brilliant. And I think Laura, you know, Laura Modi, um or Hughes Modi, who was my director of hospitality But also we worked in so many different capacities with her in the company.

22:48 I loved working with her because her brain worked different than my brain. And um That's the opportunity. is when you realize that diversity on a team, whether you know there's lots of kinds of diversity But when it comes to uh brain diversity, not just with neurodiverse people, but age diverse people.

23:07 you get a benefit, an effective benefit that is not as uh noticeable, quite frankly, in some other diversities. Uh so I found that over and over was really helpful. Part of my job sometimes was to find the blind spot. You know again if you are very focused. You know, I one of the things I said to Brian early on

23:28 Um was You know, I I've seen the business plan now. I know the goals of how big we want to be in three years. This was very early in my tenure. I said, but what we really have done everything we're trying to do is to like have no regulations And pay no occupancy tax. Now hotels pay a bed tax, occupancy tax.

23:48 We're not paying it and we're trying to do everything we can not to pay it. Uhing that You know, so for our listeners and viewers to know this This is something that a guest pays. It's not the host who pays it, the guest pays it.

23:59 It's part of the bill. If you go and stay in a hotel There's a big big tax part of the bill. But it made us more affordable by not having to pay tax have our guests pay taxes. Long story short, as I shifted, Brian. If we're as big as we're gonna be three years from now, I promise you we're gonna be regulated. I promise you we're gonna be paying occupancy taxes. So let's take some proactive steps. Towards

24:22 Building. A strategy for how we're gonna be regulated. And that's uh that has consistently been Airbnb's biggest challenge. is regulation in municipal markets all around the world. If we'd started a little earlier, maybe in New York.

24:37 Maybe in New York it wouldn't have gotten to the point where it has been toxic. In New York. The whole For the last dozen years. Um, ever since I was there.

24:47 And there's a few other markets in the in the world where it was like that. So I would just say, you know, um The value In And having some age diversity.

24:57 even when you have an older person reporting to a younger person, is it can be collaborative. There was a guy named John Q. Smith, uh, you know, an engineer who you I think you probably remember him I Uh at at Airbnb. So this is a guy who looked younger than he was, and a little was he was a little bit nervous about pe like telling people his age.

25:17 But the thing that was great about John is over time he was not necessarily gonna be the best coder. uh at Airbnb. There was a whole new collection of coders coming in every every You know, month. But he became a great manager.

25:31 And The beautiful thing about moving from the uh you know individual contributor to the the manager, the person who can actually Bring out the best in a bunch of younger people. Who maybe better technically than he or she is. But they know how to elevate talent.

25:49 I I call this invisible productivity. It's it's productivity in which you make everybody else around you better. And that's something I tried to do with my teams at Airbnb. And ultimately I had six different teams. five hospitality and five other teams reporting to me. And I did my best to just

26:06 Be the kind of person Who wasn't solving all the problems, but I was trying to There's a woman named Lisa DeBost who is a at Airbnb and She one day came I the HR department department was reporting to me at one point and she was running HR. She was twenty five and had no background in HR at all. And one day she came into me and she just said, Chip, you are my confidant.

26:26 And Lisa has a French accent and s you know, fluent in French and She said so she said confidant in just the right way. And I and I said, Oh well thank you, Lisa. But I said to her, You haven't given me any juicy details yet. Like a confidence woman who has the secrets. And and she said to me, No, in my in my part of France, A confidant is somebody Who gives you confidence.

26:49 And it was like, oh, well, maybe that's what a mentor can be. is a confidant, someone who gives you confidence and helps by asking questions Helps you as the younger mentee Find your roadmap to success. So you're sharing a lot of really good examples of

27:06 the value of older folks being within tech companies. So let me just ask you this. How How real is ageism? In tech. Yeah. And that's because

27:16 A lot of people that are hiring are probably thinking, No, no, no, I'm not biased. I'm gonna hire the best person. If there's someone in their fifties, I'll hire them, no problem. doesn't feel like it actually works out that way often. Just how real of the problem is this? What do you see? Yeah. You know, it's clearly a problem. Um I'd say it's maybe a little bit less of a problem.

27:34 Than it was a dozen years ago. Yeah, yeah. It doesn't usually go there almost a blind spot. You know, the in Airbnb we had a group called Wisdom at Airbnb. It was an employee resource group for people 40 and older. And so there are lots of these kinds of groups that didn't exist a dozen years ago in all kinds of tech companies.

27:53 Which is good because it means that there's a there's a voice and a a way to congregate with a bunch of people who are older. Ultimately we had these senior we had these senior nomads come in. And be like the voice of the customer for ten weeks at Airbnb. And it was the wisdom at Airbnb. older employee group that really actually pushed for this with Brian. But the the challenge is

28:16 In a world in which the Smartest new people Especially when it comes to technical skills and engineering. Are coming in with a whole new you know, uh set of skills that an older person doesn't have.

28:30 The the older person is both expensive uh and may be perceived as slow. So In the era of AI It's a whole new ball game.

28:41 And the question I think will be Yeah. What A I cannot do is the human wisdom piece. Artificial intelligence

28:51 And and human wisdom might be the balance beams here. Is it possible that older managers who have a little more emotional intelligence, a little more pattern recognition A little bit more wisdom. Um

29:05 uh can be a value to a company. And so it's still and the the the jury's still out there's a New York Times article that just came out. About the question of Is AI gonna wait wipe out older people's jobs or younger people's jobs? And I think the answer is both. Oh.

29:23 But the The question is How much how bad is it for both of them? And um I I think the what I would say to an older person, and when I say older, I mean like forty five or older

29:34 If you've done well financially and you're doing okay. The question you might ask yourself is Are you open as I ultimately was with Brian in my fourth year at Airbnb? I took a substantial pay cut, like I think it went to down to forty percent or fifty percent time. And my stock Uh my you know, options were d dropped to that level, my salary's dropped to that level.

29:56 Because I didn't want to work full time anymore. And There are a lot of people who can be valuable in a company. We have some institutional wisdom, some process knowledge of how to get things done. in this organization and in tech companies that's really important.

30:10 Um Airbnb one of the biggest challenges that Airbnb has always been How do I get shit done around here? Um and Process knowledge allows you to understand how do you m how do you deal with an org chart. and get things done partly because you understand

30:25 the motivations of different groups. And that is something you build over time. So long story short is um I just think that Mm. You know, older people might look at their

30:37 workload and say I'm willing to take a twenty percent or a forty percent pay cut to go to eighty percent or sixty percent time. And the company is gonna get Their money's worth. In that.

30:49 That's a really interesting point that if you're older and you're maybe less connected to the most cutting edge Ways of building and and uh coding. AI makes that a lot easier in many ways, where you start to just talk to it. You don't even need to understand what's happening underneath. Yeah.

31:04 So there's a lot of listeners who are older in tech. There's a lot of listeners who are Approaching. Midlife, let's say. Worried about what happens to their career.

31:13 When you look at people you've worked with and had at your academy, which we'll talk about. who continue to thrive and continue to have a really healthy career in tech. What do they do differently? What do they do? What what do they have in common that other folks you think should work on and focus on? I think this k this idea of being a mentor and a mentor and an intern There's just the voracious appetite for curiosity. When I talk to someone.

31:37 who's in midlife and wants to be in the tech world or already is. The thing I say is show up with curiosity and a passionate engagement for what you do. And people won't necessarily notice your wrinkles as much as they'll notice your energy. And energy has two parts to it. Uh energy is they uh notice that you are not just sort of resting on your laurels. You're you have

31:59 Like physical, you know, energy in how you Do your job. And when people are like that, they are sort of timeless. They are a they're age fluid, as I say. Um we talk about gender fluidity, well it could be age fluidity. They they don't

32:13 They're not defined by their age. But the other part of energy is that's important is p being positive. You know, that's sort of more energetic, like a little bit more California energetic. There's a sense of like when someone's got good energy You're drawn to them.

32:28 So it's about showing up with the kind of energy of someone ten or twenty years younger than you. And then showing up with positive energy. And I think one of the things that I would say I did well at I mean there's lots of things I didn't do well at Airbnb.

32:44 But In terms of what I did well is I was very approachable. And over the course of time, the number of mentees I had, the number of people who just wanted to have coffee with me or tea, the number of people Who just said, Thank you for being in that meeting. You just sort of gave it a positive

33:00 Feeling. was really important. And and um So my energy, both the positive energy part and then also the fact that yeah, I I could work sixty and seventy hours a week.

33:11 And I could travel around the world as the as The secretary of state of the company, which is what Brian called me a couple of times. On the stage. The fact that I could do that meant that no one was looking at me and saying, Let's get rid of the old fogey.

33:27 Uh well maybe some people were, but n I wasn't aware of them. So I just think show up with that passionate engagement, that curiosity that energy. the ability to be both the learner and the teacher. With respect for people that younger than you. And you're gonna probably do pretty well.

33:44 That is really great advice. Today's episode is brought to you by Koda. I personally use Coda every single day. to manage my podcast and also to manage my community. That's where I put the questions that I plan to ask every guest that's coming on the podcast. Sorry about my community resources.

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35:03 Interestingly, curiosity comes up a lot when I asked AI forward people, what are they Focusing on helping their kids learn most. Curiosity is the most common thing. way to describe so uh at every stage of life curiosity

35:15 Is uh some to cultivate. I wanna go to the flip side of companies looking to hire. Feels like there's this uh untapped supply of awesome people that company is with ageism and tech. Uh

35:28 aren't finding and hiring. So to help hiring managers and companies take advantage of this. What's something you suggest they do? How do they shift their mindset or maybe shift the way they uh they hire that might help them find these people? I think we're moving into there's a there's a book that David Epstein wrote called Range.

35:44 And the whole premise of range is that we're moving out of the era of the specialists and into the era of the generalists. And I think AI is just accelerating this. Um As we are more reliant upon AI, and AI can can be exceptional at technical skills and solutions

36:04 Really expeditiously. I think generalists, people who can think broadly, become All the more important. And I think that what I would say to someone in HR

36:17 Or recruiting. Uh is yet beyond what I already said before is is the person passionate? Are they curious? Are they a learner? Um, do they have gr good energy? But I would also say Are they a generalist when they're a problem solver?

36:33 Because I actually think that's gonna be An increasingly important part. Uh How Effective companies.

36:41 Think Broadly. So I think that's a key one. I think also this idea of how do you create

36:50 Intergenerational collaboration in the form of mutual mentorships. Um One of the things I I I loved at Airbnb that would there are a few people I did this with Where I had something to teach them and they had something to teach me. So um good example my iPhone.

37:06 So There's ninety seven percent of the utility of my iPhone that I probably don't use and don't know. how to use this was, you know, back in let's say two thousand thirteen, two thousand fourteen. And So

37:19 There are people in Who knew iPhone or Google Suites back then. I never used a Google Doc back then when I joined the Airbnb. So There were people who could teach me something technical.

37:30 And then They wanted to learn something from me. Would you be like How do you want a great meeting? Um, or how do you give a great employee review?

37:39 Yeah. There are a lot of managers who've never been a manager before. And And so how do you disperse People like me in the organization.

37:49 So that you don't you know there's usually not enough time. for these young managers to come to some training session on how to do a good You know, employee review. So you sort of have to do it out there in the field. It's like apprenticeship. You know back in the trades.

38:03 You're a you're an electrician apprentice. Not because you're watching, you know, some video on it. You're out there in the field doing it. And and that's of huge value in a younger company. When you have some Older people.

38:18 who have not been vested with the responsibility of managing those younger people. Because they may be have they may actually be reporting to someone. Younger than them. But they're there to actually be support. And um in some ways I think that was part of the

38:33 Unexpected value that I was able to offer to Airbnb and to Brian specifically because There are a ton of people in the Airbnb who were not even in my departments. Who would come to me and say I'm having a problem.

38:47 H how do I solve this? Can we spend lunch together? And You know I almost always said yes. I think the reason people did that in many ways is you just have uh a very unique aura of wisdom and and it's hard to replicate that chip.

39:01 Yeah. Y yes and It all comes back to the curiosity. If I was just the older elder Dispensing wisdom.

39:13 People would have gotten bored very quickly. And I think the fact yeah, yeah, I mean I was on the board of Burning Man. Ooh, that's cool. And so there is a I I I I show up As someone who

39:24 Feels younger than I am. I mean, I'm turning sixty five this year. So The bottom line is I think

39:32 People lost track of my age. Part partly because I lost track of my age. Uh that's such a good such good advice on the front end. uh to be successful as a person kind of getting older in tech is Curiosity positive.

39:46 energy, the way you talk talked about it, uh passionate Passionate, uh Engagement, is that the term? Yep. And then on the other side is Uh

39:55 higher generalists. This actually comes up a lot in in the AI conversations, just exactly as you said, the power of generalists reminds me I'm I'm going to this gym now and The lady there is just like I love AI so much'cause I'm just such a big picture person and I can so bad at just getting thinking about the details and AI solves all that for me. It's like here, here's what I want to do. I'll do this for move my house to here, here. And it's like here's what you need to do. Step one, two, three, four, five. It is remarkable. I mean, you know, it it since the time I've known you

40:23 How fast it has become dominant in our lives. Uh But yeah, I think I one other last thing I'd say is look I'm privileged. So for those of you who are listening or watching this. And you're saying well

40:36 You know, Chip, you were fifty two years old and they came to you. Like that doesn't happen to me. I'm not in that position. The thing I would say is you're right. So I But I could have been plucked and brought in.

40:49 And Partly as as Brian's boy People would have like rejected me. Because if I didn't show up the right way. It wouldn't have worked well.

40:59 Uh And there are lots of people who Brian brought into the company. Who didn't work well. So I think I think

41:07 The key is how do you get the foot in the door? And at the end of the day Um you know, those second and third order of you know s uh degrees of separation Um in terms of networking is are still essential.

41:22 But the most important thing is to be able to articulate What you have accomplished In a new way. That a recruiter says

41:33 Wow. And so I I really tell people like I I would love

41:40 First of all, the question that uh I think it was it was Who was someone asked it. I don't remember if it's Cheryl Stanberg or someone else asked her Is it like what's the biggest problem you're dealing with here? And how can I help you? Like that's a great that's a great line. Number two is uh

41:56 What I love to see is not so much what roles you've had, what bullet points do you have of your The things you've learned. Give me in a paragraph Okay.

42:09 I a thorny problem. You faced Um what what was the problem? And how you got how you what skills you used. to actually accomplish it and what was the result of that.

42:22 I would love to see a resume like that. And the older you are, the more you can actually have a resume like that. And then you can use that as the conversation piece. When you're doing interviews. So I love that we'll I love we're getting into interview advice and resume advice. Yes. Um speaking of throwing problems and also uh why Brian decided to reach out to you, I want to go back to the beginning of your career.

42:44 Yes. So Right. You're good at this, by the way. You're good at this. Thinking ahead. Okay, so You're in business school, you left business school, you just said you're like, Maybe I should start a hotel. Uh

42:59 Something that rarely works out. Usually probably leads to a lot of money and a lot of frustration and just like, okay, what have I done with my life? Worked out for you. Ended up building the second largest boutique hotel chain in the world, the Droad of V. Uh, beloved, uh I I I loved every single experience I've had as Gerada Vieh when you sold it. I was like, that is so sad. Talk about just that. That story. Uh I know this could go on for hours, but what's the Yeah, I'll be I'll be brief. Yeah.

43:22 Twenty six years old. couple years out of Stanford business school working for a commercial real estate developer. I was bored silly. I wanted to do something more creative. Bill Graham, famous concert promoter, said to me You know

43:34 I had because I gotten to know him. What San Francisco really needs is a rock and roll hotel. So I decided to start looking to f to find a broken down motel hotel. That I could turn into a rock and roll hotel and I found something in the tenure line. Uh, and uh and turn it into the Phoenix, which became

43:53 A famous rock and roll hotel that I have owned for thirty nine years now. Um So long story short is That was how I started You're not a Viv in the company. And we grew to fifty two hotels around California.

44:06 became the second largest, as you said, in the in the world, uh, in terms of the number of hotels, boutique hotels that we operated. And I loved it'til I hated it. In my late forties, I hated it. Didn't want to do it anymore. I was, you know, the great recession came along and it was just kicking my ass. And I really went through a bit of a what I I now call a midlife crystalis. uh but a midlife crisis Um, where I just

44:30 wanted to change everything. And um I got through it. Uh I had an M D E n had a near death experience where I had an allergic reaction to an antibiotic and I died. And from that point forward, I realized every day is a a gift and a bonus. And um

44:45 Uh You know, I decided to sell my company at the bottom of the great recession. So that's So that's really how I

44:53 created this space in my life. To be able to join Airbnb. Well let's back up a little bit, this near death experience. Uh share more there. What happened there.

45:04 Yeah, I was uh so I write books, I've written seven or eight books and I had written a book called Peak, uh how great companies get their mojo from Maslow and it was a book that Brian really liked and Part of the reason he uh he wanted to reach out to me. Um I was on a book tour. I had a broken ankle.

45:21 Uh It broke my ankle at a a bachelor party, uh playing baseball. And um I ended up with a cut on my leg and um the cut on my leg had fertilizer in it and went septic. And so I was on uh

45:36 very strong antibiotic and I Died. I went flat line from the al allergic reaction to the antibiotic. And so I saw, you know, I it happened nine times over ninety minutes. I kept Dying kept flatlining. And yeah.

45:51 ended up in the hospital for a couple three days and they finally said, Listen, it's an allergic reaction, we believe it they thought it was I thought they thought it was a heart attack. They had a bunch of stuff, stroke, et cetera. No, it was The allergic reaction. So But I you know I saw Birds. I mean I I saw all this beautiful stuff. I we don't have time to go into it. You want to hear this? Yeah, no, I saw this beautiful stuff.

46:14 The the best I I think There's a hotel in San Francisco called the Vitali that I built, um across the street from the ferry building and It's still there, but it's no longer called the Vitality. Um in that hotel there were these slippers in every guest room. one slipper said slow, the other slip it said down.

46:31 Um, and so I was wearing these slippers. In my flatline. Uh flying in in the

46:41 Forty foot tall. living room in the Alps. Surrounded by birds that were Twer tweeting and and chirping at me, and I understood bird. Talk.

46:53 I understand. I understood exactly what they were saying. And they kept telling me If you slow down, you will see beauty. And you will see ah.

47:03 And there was a bunch of other things, but let me just l limit it to that and just say and then the birds would like say it's time to go. And the birds would go out the big window. Yeah into the mountains. And I would try to follow them and right as I would get to the window. All of a sudden I'd come back to life. Holy shit.

47:22 Uh I love that this was uh like there is a message inside of this experience. I don't know how many people experienced that. Clearly this led to a big life change. And it's interesting that a lot of times you need something like that. Like you've been doing this for how many years at that point? running try to be.

47:38 Uh at that point I've been running GRV for twenty two years. And twenty two years. And it's interesting that you need something like that a lot of times. Otherwise it's just momentum just keeps carrying you forward. Yep. Within two years I'd sold it and you know, I I'd had ch the chance to move on. So with buildings water vie something you've written about a number of times is just The way you built it is a really unique approach to building a business specifically there's a huge focus on culture.

48:02 Which also came out at Airbnb. Talk about just why you see culture such an important part of how you build a business like tangibly,'cause a lot of people talk about culture, warm fuzzy stuff, but you think about it very tangibly. Culture is what happens around here when the boss is not around.

48:19 Um And and the more distributed a company The more culture's important. Because The boss is around.

48:29 in a traditional bricks and mortar workplace where everybody shows up at Eight and leaves at six. And We all see each other. But

48:39 Uh Uh In my company in Joadiv, we had fifty two hotels and twenty five restaurants and four spa and It was distributed. So I couldn't be in all those places all the time.

48:52 And same similarly with Airbnb. I mean Airbnb had offices around the world and was it was a global company. So The more distributed you are, of course, in the remote work world we live in. the more culture is important and more difficult. Because the w when you're remote

49:09 You know, there's these few cues you have about how we do things around here. And they're usually in a digital virtual format. Which is why You know, it's all the more important for you to have in person gatherings. Of a team more often.

49:25 If you are virtual. So at the end of the day, the reason the culture is important is because it actually helps It helps guide people in terms of making decisions. But it's also a magnet. For the right kind of people.

49:38 So Oracle has a different You know, a culture than Apple Which has a different culture than Facebook. And so You can choose the place you're gonna work based upon the culture. And

49:50 There are people who can be very good at what they do. But if they're in the wrong culture. They're in the wrong kind of environment and they're not willing to shift. To fit that culture. And we still hide at Airbnb all over and over again.

50:03 Uh in fact Airbnb saw it I think when with Amazon people. Um Apple people have resonated pretty well at At At uh Airbnb.

50:13 Amazon people less so. And those are two different cultures, Amazon and Air and Apple. And that therefore Understanding a culture before you even actually Take the job.

50:25 is one of the more important decisions you need to make. Is like Is this culture a culture that I can live with? Um and maybe influence. Um

50:35 There's language about culture fit. I like to say culture ad. Because culture fit to me means can actually be quite negative. toward somebody who is

50:47 The aberration. Um you have to fit in. And especially if it this is like a demographic thing, a person of color. A a gay person, a you know, a a person in a wheelchair. So you have to fit in.

50:59 But a culture ad suggests that actually having some diversity on the team is helpful because it actually adds to the culture. But it's still ha you still have to Be able to get along in that culture. So

51:12 Culture is an intangible, that's the problem with it. Is it's hard to measure. But you see its value and you understand whether it's working based upon poll employee polls reports and things like that. You talk about having to understand a culture is such a

51:27 Key part of having success at a company. Do you have any advice for just how to understand the culture for someone interviewing? I don't know. Like, you know, you came in, you work part-time, it's easier to experience at all. Any tips there for like okay, this is for me, this is not for me. When you're interviewing you're out you're also interviewing them. When you're interviewing, it's not about you having to prove yourself. It's also for them to actually prove themselves. as a company and also try to understand if there is

51:53 um some alignment in the company. And so the kind of questions I would ask As someone who's being interviewed would be What are three to five adjectives that define this culture? What's the biggest problem in this culture?

52:08 In terms of something that's just endemic or s like baked in across the organization. And is it ever gonna get fixed? And how could I come in and maybe help? That's

52:19 Uh which frankly at a very junior level you're not gonna be able to help it. Uh except for in very minor ways. If you're a senior person, you might be able to help it. Um So this are those are the kind of questions I'd want to know. And frankly

52:34 If I'm asking that same question about what are the adjectives To multiple people. Am I hearing the same thing over and over again? Um, and if I'm not, is that because there's not an alignment? Is that because different departments.

52:46 have different flavors. Um Because you can have a culture within a department that's very different. than the overall corporate culture. The corporate culture certainly has an enormous Oppressive. uh influence.

52:59 But uh You know, you can you can you can be in a culture uh a really great culture of a team. Or a department. In an overall company culture that's not good.

53:13 In the long run, that oppressive company culture. He's either gonna have to evolve Or Your department may be m you may lose people. When I reflect back on one of the on on the impact you had, it there may be one of them

53:27 Funny. Uh Things I think about is uh triangles showing up a lot on Decks. Uh and specifically uh rooted in Maslow's hierarchy, just like everything's this Maslow hierarchy metaphor.

53:40 True. Um And This one uh I don't know, specific piece of this is you have this kind of model you think about for how to help employees at a company, you're kind of root it in your peak. book uh philosophy. Maybe just talk about that. And then if there's anything else you want to expand on with this power of thinking through the Maslow hierarchy. So yeah, Maslow's hierarchy basically five levels later in life he had a s seven and an eight level model, but

54:06 You know, Uh at the base is Your physical Uh you know. The kind of physical water, food, air.

54:14 And you move up to self actualization at the top. Um So To use this model as a hierarchy of needs for employees, customers, and investors is what the peak model is about. Uh the the

54:28 you know the peak uh my book. Um Is really simple. It's money or compensation at the base. um recognition in the middle and meaning at the top. Now there are some industries and some kinds of jobs in which money is ninety percent of the pyramid.

54:45 So just because it's at the base doesn't mean it's not The dominant part of the pyramid. But The differentiation often is in recognition and meaning.

54:54 In nonprofits usually the the money piece of it's rather thin. And the recognition's there's and meaning's huge. So I so understanding how do you create an organization And I and I gave a TED talk in two thousand ten about this topic as well. Um how do you create a

55:10 How do you measure the intangibles? uh of meaning and how do you create an environment where people feel a sense of meaning. Um The customer pyramid, briefly, I'll just say that one is is Meeting expectations is the base.

55:23 Meeting desires is in the middle. And then meeting unrecognized needs. And I think one of the things that we did at Airbnb about a year after I joined and when Jonathan Meldenhall was joining is We really tried to Ask ourselves, are we in the home sharing business or are we in some kind of

55:41 Business that is Even bigger and broader than that. And ultimately we we came up with the idea that we were in the belong anywhere business. uh Airbnb was not in home sharing. We were in belonging anywhere. So the Once you have that

55:55 uh down that was sort of the unrecognized need at the top of the pyramid. Then that becomes an organizing principle for How do you teach your hosts? To create a sense of belonging. Um, how do our how does our marketing and advertising

56:09 Play up the belonging piece. Especially and the everywhere piece. Because hotels are not everywhere. But homes are. And so

56:16 I would just say that you know this model the idea of hierarchies Is I think very helpful. Um and uh Yeah, my book peak is It's been around for eighteen years, but I still have asked to give

56:28 twenty or thirty speeches a year on it. Oh man. This uh this pyramid of comp recognition meaning is really interesting, especially these days because Uh like with all this AI. uh researcher poaching.

56:40 There's all this talk of just like it will people just go work wherever the You know, they get they get the most money, or is there a mission and and meaning to the work they're doing that will keep them not taking a hundred million dollar offer and Seems to be happening in a lot of cases, which shows you the power of meeting. Yeah, I mean

56:57 If you know you're working for a toxic company, at some point your conscience kicks in. Whether it's toxic in terms of the purpose of the company toxic in terms of the leadership or the culture. Um Yeah, life is too short.

57:09 Okay, so you've had two major shifts in your career. You Started the hotel chain, you went. Then you went to Airbnb. Most recently, the Airbnb experience, I imagine led you to starting something in the c called the modern elder academy.

57:24 Talk about what is the modern elder academy. Yeah, what is going on with that modern elder academy? The modern elder academy. So there was a couple of times where I was called the modern elder at Airbnb. And I then I was told that a modern elder is someone who's as curious as they are wise. So Uh Jonathan Mildenhall, who is the chief marketing officer at at Airbnb, used to call me the modern elder as well.

57:48 And when he and he said like If you ever create a school you you know Modern e Modern Elder would be a good name. And so we talked about it and Next thing I knew I was like saying, Okay, this is called the Modern Elder Academy. We now call M E a because elder is

58:03 A fraught word on some level. It makes you sound elderly. But um What I really wanted to create was a place where people Could Come and do a workshop.

58:13 You you know, they're five day workshops Um in Baja on the beach or in Santa Fe on a big four square mile Uh horse ranch. And reimagine and repurpose yourself. And navigate transitions. We go through so many transitions in the middle of our life.

58:31 Let's say betwe I I define midlife as thirty five to seventy five guys, so like This is it it's a very It's a very long life stage. So we go through a lot of transitions. We are constantly evolving our purpose.

58:44 We're building our wisdom. You know, we have knowledge management tools out there, but where are the wisdom management tools? Where are the tools that help us to get wiser over time? And then we need to reframe our relationship with getting older. Because De Becca Levy has shown at Yale that when you shift your mindset on aging from a negative to a positive, you get seven and a half years of additional life.

59:04 Which is more life than any other biohack that's being done right now. So That's what we do. And we have seven thousand grads from sixty countries and Fifty six regional chapters around the world. So it's a bit of a movement.

59:17 And um I teach. I I teach some of the workshops and we have all kinds of famous people Who come and teach and For me, creating the world's first midlife wisdom school Just feels like the the natural next thing for me to do. I

59:32 I love hospitality, so it's a very upscale kind of experience, but we have scholarships. I love um retreat centers. I was on the board of the Esselin Institute. in big surf for ten years. I love wellness. I've owned the Kabuki Springs and Spa for Twenty eight years.

59:50 Um, which is the largest spa in San Francisco. And I love education. And my book Wisdom at Work, The Making of a Modern Elder. gave me a curriculum in which we've expanded quite a bit with

1:00:02 Uh Harvard, Yale. Stanford and U C Berkeley's helping us. H a great greater curriculum around midlife. Um and so That's how MEA came about.

1:00:14 Uh, to your point, I forget you said it I think you said Jonathan has said this was the natural next step for you. I completely agree. It's like looking back, this is the obvious thing you should be doing right now. Yeah. Also I'm learning more things about you. I don't know. You were involved with the Kabuki Spa, I think Essel and I knew just keep keep getting more interested. Thank you.

1:00:32 There's a couple threads here I want to actually follow. So this point you made about shifting your mindset to aging is a positive. Thing. makes you helps you live longer. That's such a powerful point. Can you just speak more to that? Just what does that look like? Yeah, y there's a couple there's lots of data points I'm just gonna I'll talk about two. One is this Becca Levy study, which has been going on for fifteen to twenty years. If you sort of take you buy into the ageism of American society

1:00:57 Or Hallmark cards when you get a A c a card at age forty, fifty, or beyond. There's a belief that life gets worse as you get older. And Um, and if you can survive your midlife crisis, all you d have to look forward to is disease, decrepitude, and death.

1:01:14 And the bottom line is uh You know, there's a lot of things that get better with age. I wrote a book called Learning to Love Midlife. The subtitle says it all, twelve reasons why life gets better with age. And what I really wanted to do with that book Which is Really it it summarizes the MEA curriculum.

1:01:30 I wanted to write a book that sort of helped people to see the upside of aging, the unexpected pleasures of aging. Uh, so they had a pro aging, not just an anti aging point of view. Because when you actually have a pro aging point of view and you see the the upside of aging You take better care of yourself. Both your mind and your body.

1:01:47 You actually Are willing to learn and try new things. One of my favorite MEA questions is Ten years from now, what will you regret if you don't learn it or do it now? It's a powerful question. Really important question as we get older. When you're young, you know, you've got all of you know all of your life left ahead of you.

1:02:05 But when I moved to Baja part time but in Mexico At age fifty six. Um, I had a mindset which was I'm too old to learn Spanish. I'm too old to learn to surf. But when I said it. Ten years from now, what will I regret if I don't learn it or do it now?

1:02:20 And I said, Well, ten years from now I might still be living in Baja Like I should learn this I should learn Spanish. I should learn how to surf because we're right next to a surf break. And so I did. Um so

1:02:32 What I believe is that anticipated regret is a form of wisdom. And so And it's a catalyst for taking action. So That's one data point. The other data point is something called the U curve of happiness.

1:02:45 And it's been around for twenty years and it shows the following. It has changed in the last couple of years because Young adults are ha unhappy. Like never before. So a twenty or a twenty two year old really unhappy, twenty four year old really unhappy. And historically w the way it was is you were happy From eighteen to twenty three or twenty four.

1:03:03 And then around twenty three, twenty twenty four, you start to see a long, slow decline. in life satisfaction that actually uh bottoms out between forty five and fifty. I'm sorry to tell you that, Lenny, since you're forty four. Um, but your mileage may vary. Uh so you're saying I'm the least happy I'll ever be. Like that's only upside. That's great. Yeah. Well here's the part that's weird is that Well before this re research was done. And it's global research across all demographics. What they found was uh starting around age fifty or fifty two.

1:03:35 You get happier. So that you're happier in your fifties than your forties, sixties, fifties, seventies happier than sixties, and the women in their 80s happier than seventies. So Wow. And it's partly because We are in around forty five to fifty doing this thing called the um the midlife unraveling.

1:03:52 what Brene Brown calls the midlife unraveling, you're unraveling your expectations. Your uh what you define as success. uh your definition of you what beautiful body looks like And you get some you're liberated into freedom in your fifties and beyond. And uh

1:04:10 I can say that yeah, I'm happier today at sixty four than I was at Forty seven when I was going through my flat line experience and Not wanting to run my company anymore. Used this term earlier, the midlife chrysalis, was that what it was? Or chrysalis, chrysalis. Chrysalis. What is that? Is that kind of along the same lines?

1:04:26 So if you think about the caterpillar to butterfly journey, midlife Is the chrysalis it's that cocoon in which all of the change is happening. At the time, you know, when you're going through it, it's like oh shit. My five. My life is liquefying in front of myself, but you know, on the other side of it, you there's a metamorphosis that happens.

1:04:46 And so Uh I I like to use the language and in fact I have a podcast called The Midlife Crystalists. Um because I want to help You change the dialogue. Around midlife. So that

1:04:57 The number one word attached to midlife is not crisis. Um but in fact it's maybe Chrysalis and the idea that Um, life is meant to be transformative uh during that era. That is actually very empowering. I am

1:05:11 Sort of going through that, not necessarily in this intense way yet, but that might be coming. You said there's a bunch of upsides to being getting older. It might be helpful just to share a couple of those things for folks that are like, Oh wow, I didn't realize that. Emotional intelligence grows with age. Um our wisdom can grow with age, although we know seventy year olds who are not as wise as thirty year olds. So it's a matter of what you do with your life experience. I define wisdom as Metabolized experience mindfully shared for the common good.

1:05:38 Uh what else gets better with age? You learn how to edit. You can't you you have no more Fs left to give, no more F to give? There that is absolutely true, especially for women as they age. You are more spiritually curious. Uh your um

1:05:53 I mean the list is long and and so There are a lot of things that Yeah, actually another one that I don't love is c you're not compartmentalized. Yeah when you're younger you're compartmentalized. As you go grow older, you are growing whole.

1:06:06 And that means you're alchemizing Curiosity and wisdom. Introvert, extrovert, masculine, feminine, gravitas, depth. And levity. Lightness.

1:06:16 And The people who I really admire who are eighty five years old They're so present and they're so whole. They're like they are just who they are. There's a quote I found from you along these lines, The societal narrative on aging is just don't do it.

1:06:31 Yeah. There that's I mean, we sort of say like you we we want we don't wanna age, but we do wanna live. And quite frankly, aging and living are the same thing. As are aging and growing. Mm.

1:06:44 Coming back to M E A, just for folks that are like Interested, curious about this. Who's this for, would you say? Who should seriously look into this program. MEA is really the people who tend to come to MEA are in the midst of a transition. It could be uh selling their company, leaving a job. Getting divorced, um Having kids, um

1:07:05 becoming an empty nester, taking care of parents till they're passing away. having a health diagnosis that's scary. So Average age is fifty four. And it's people of all walks of life.

1:07:17 Uh, so it's not just the tech industry, but a lot you know, it's very popular in the tech industry. Um, it's people who are looking to maybe do a reframe of their purpose. Uh and maybe even a reinvention of their career. And So yeah, and and the two campuses are just gorgeous. Uh it's been called the Four Seasons meets Blue Zones.

1:07:39 Meets the Slan Institute, which I like. Um And uh we don't we have online programs too. And so You don't have to come to either of our campuses in Mexico or on the beach or in uh New Mexico, uh, you can actually do it online.

1:07:54 Those three, yeah. That's the tagline. That's your tag a line right there. Esseline meets blue zones meets what what was the first one? The four seasons. The four seasons. Wha Yeah. Nailed it. Okay.

1:08:05 I'm gonna zoom out and take us to uh recurring segment of this podcast. I wanna see if this goes anywhere. Uh AI corner. And with AI Corner ask us just what's a way that you've Found AI useful in your

1:08:18 work or in your life, any kind of trick you've learned, any workflow, anything you found useful. Yeah, you know, I I have a daily blog, uh, it's called Wisdom Well and it's on the MEA website and Um when I'm looking for inspiration. You know? AI does it for me. And

1:08:36 Ultimately it gives me a first draft. And that's good enough for me then to say, like, okay. Because there's times when I'm like missing the inspiration. I tend to write really well in the morning. If it's any other time of the day, I do not like writing. Creatively.

1:08:50 Um, so if I have a deadline for tomorrow and it's five o'clock in the afternoon, it's like okay, chat G B T, I'm on my way to you. And I I tend to use chat G B T the most because I don't know. I mean, I like claw as well, but um Yeah. Okay, awesome. I was gonna ask which tool you use, uh and what's your workflow there? Is it you Use voice mode, do you just kinda type out here's what I'm thinking about, write me a little Drop blog post.

1:09:12 The good news is that at this point uh it knows me well enough and my and my blogs and I've actually you know it it it It knows my my S S weird sense of humor. Uh So it's able to ape me pretty well. So I'll just say I need a

1:09:27 Two hundred fifty word. post on um Like today, the you know, today's post was opposed that chat GPT helped me with it. I said, I believe that there's a a a refrain that needs to happen with the soul. We tend to say like I have a soul or I don't have a soul.

1:09:43 But what if this my soul has me? Um what if in fact my job is just to be This Vehicle. for my soul to k go to the next lifetime.

1:09:55 And my so my job is to be the steward of the soul. And I said, write me something around that. And so it was just a weird i idea. And of course my m not all my blog posts are so new age and And uh like that I write I re I read a lot on leadership. But that was one that, you know, within you know thirty seconds I had

1:10:14 A two hundred fifty word. You know, blog post that I then adapted and there you go. Amazing. Chip, we've covered a lot of ground. We've gone through your entire life. Maybe actually just the tip of the iceberg.

1:10:27 With that we reached our very exciting lightning round. I've got five questions for you. Are you ready? Yes. Let's do it. First question, what are two or three books that you find yourself recommending most to other people? My favorite book of all time, Man Search for Meaning, Victor Frankel, uh in a concentration camp in World War Two. When someone's going through a hard time in their life, I say, Read that book, you'll realize it's not so bad. What you're going through?

1:10:49 Yeah. Um but it also really speaks to this idea of despair equals suffering minus meaning. I wrote a book uh called Emotional Equations that was a New York Times bestseller. That spoke to this idea that what if you could take all of your emotions and turn them into equations? Very engineering minded.

1:11:06 Uh of me. Um so that's one. Um I You know

1:11:11 I love Uh any book by Liz Gilbert. Um Sort of the opposite. So Elizabeth Gilbert wrote Epre Love. Her her book, she's a she's on faculty at MEA, she teaches here.

1:11:23 Um Uh big magic. Is just a beautiful book about sort of like how do you Get in the flow.

1:11:31 Allow the genie. To come through you. Um her TED talk in two thousand nine was about the fact that genius Is not about being the genius yourself. It's about being the receptacle for the genie to come through you.

1:11:44 I wanna come back to this uh equation you shared. I was gonna get to it, but I didn't, so this is a good opportunity to. So there's a couple of that are really interesting to me. This is your about these in a book. You have a bunch of these equations about living a happier life. So the one you shared is despair equals suffering minus meaning. Yes. And so the implication there is if you want less despair, increase the meaning.

1:12:05 That's right. There's sort of Buddhist philosophy, number the first noble truth of Buddhism is that suffering's ever present. And so if suffering is a constant and you have two variables Uh using some algebra, I guess, um you know that uh if you have more meaning, you have less suffering. And so that's that one.

1:12:25 The other one that I love is anxiety equals uncertainty. Times. Powerlessness, maybe talk about that one briefly. Ninety eight percent of anxiety comes from two sources. One is what you don't know, and number two is what you can't control or influence. and based upon social science. And so

1:12:43 Um you can create an Anxiety balance sheet. And you know, create four columns. First column is what is it you do know about the thing that's making you anxious? The second column is what is it you don't know?

1:12:54 The third column is what is it you can control or influence? And the fourth column is what is it you can't Control and influence. And when you take free floating anxiety and put it into uh a an equation

1:13:06 It actually makes it more tangible and you often are less anxious as a result. Boom. Okay. So if you're feeling anxious right now, this is an exercise you can do and you'll feel less anxious. In like five minutes. Yeah. Okay, excellent. Very very good negative advice. Okay, let's keep going with the lightning round. Come back from our tangent.

1:13:25 Do you have a favorite recent movie or TV show you've really enjoyed? I mean Ted Lasso is I'm a like a sucker for for for that show. You know, when it comes to movies, I'm a total movie buff. I I We have an annual MEA film festival. Uh at our Santa Fe campus. Um

1:13:44 And I would say that The film that I'm most excited about the is coming out um that most people have never heard of it's called I'll push you. And it's the story of

1:13:54 Two guys One of whom. is uh in a de degenerative uh health condition and in a wheelchair And his best friend. Pushes him the five hundred miles of the Camino de Santiago.

1:14:06 And it's the relationship they build along that way. Amazing. Very deep cut. Do you have a favorite product that have you you recently discovered that you really love? Yes. Hair growing material.

1:14:19 No. Um You know, V uh Viore The shorts. I I you know, I sound like Scott Galloway because he ta he advertises this. But your shorts are like

1:14:30 I just love them. Yeah, they're just breathe and they're comfortable. I'm wearing theory uh joggers right now. Uh the one downside of Yari, not to make anyone mad, is they're not like very they're kind of plasticky. If you look at the material, so I'm trying to like hmm I don't know. Yeah.

1:14:45 But I do love there's nothing better. That's the problem. I don't anything else like this that is a All cotton, yeah. Yes. But I'm a fan. I have many Vori. I don't know if they're called joggers, just I don't know, weekend weekenders or something. Anyway, love you, Viore. Okay. Do you have a favorite life motto that you

1:15:01 Often come back to And find really useful in work or in life. I imagine you have many, but is there one that comes to mind? I mean, my favorite one right now is your painful life lessons are the raw material for your future wisdom. And The the premise of that is that Wisdom often comes through the school of hard knocks.

1:15:19 So when you're in the midst of a a really you know, challenging time. You're developing your future wisdom that's gonna be valuable to you. Okay, final question. You were on the board of Burning Man, or you still are?

1:15:32 Uh It was. I helped found the board of Burning Men. Okay, no big deal. So I don't know if you know this. I got married to Burning Man. We had a unofficial wedding there on bicycles. So it's really meaningful to us. I've been there four or five times. Uh

1:15:46 What's something about Birding Man that maybe people don't know, some insight story or a really unexpected piece of the s the journey? I imagine there's a lot, but what comes to mind? I would say the best not well known thing about Burning Man is that Burning Man own owns a place called Fly Ranch. Mm. And Fly Ranch is about ten miles from Burning Man. Now if when you go to the burn, uh the event in you know around Labor Day uh

1:16:12 You cannot go over there. It's it's it's locked off, it's thirty four hundred acres. But If you do if you look at Fly Ranch, um, Fly Ranch dot org, I think it might even be Where it's on the Burning Man site. Fire Ranch is like the opposite of Burning Man. Burning Burning Man is this alkaline desert, like there's no no living life there at all.

1:16:32 Very masculine. Fly Ranch is like Horace and and like Lo life lots of like desert grasses and hot springs and hot pools and

1:16:42 It and birds and wild horses and It's One of my favorite hot springs places in the world. Um, so just check it out and you can go there. when it's not during the event and and it's it's quite beautiful.

1:16:57 Feels like you might have inspired uh M E A in many ways. It didn't, yes. Chip, two final questions. Where can folks find you online and how can listeners be useful to you? So online M E A Wisdom.com is the website for M E A. My website's chipconley.com, C O N L E Y, and uh

1:17:16 I'm on LinkedIn. That's really from a social media perspective the thing that I do the most. I actually take my daily blogs and put them on LinkedIn. So And then what the what the your community can do, just yeah, come say hi. Come uh Check me out. And if wisdom's interesting to you, and I think wisdom should be interesting ever to everybody here.

1:17:37 Um on the MA website at the very bottom footer. You will see a bunch of free resources. One of them is called Why Successful Leaders Value Wisdom. It is a free resource. Um, and then there's also a free resource down there called the Anatomy of a Transition. Those two free resources.

1:17:54 Understanding how to build your TQ, your transitional intelligence. And understanding how to develop wisdom are two, to my mind, two of the most important modern skills that we can have. It's funny when you say you're on LinkedIn. That feels doesn't resonate with me. You can chip Conley on LinkedIn, just posting on LinkedIn. Something if I don't know why because I'm a little too burning in it? You're just yeah, exactly. It feels like that's not your vibe. But I love that you do it,'cause that's where the people are. Oh, I I put wild weird stuff up on LinkedIn and you know Thank thank God somebody's doing that. I got I for some reason I don't see it. I need to fix that.

1:18:30 Chip, this was incredible. Everything I was hoping to do. Thank you so much for being here and for sharing your wisdom. I am so proud as I go back like I'm your proud papa who just loves to see you in your element and I just wanna say make sure everybody knows the following. Lenny was So good to work with.

1:18:49 I really when whenever you were assigned to a private uh Project as a PM. I appreciate it because I just knew that we were gonna have great conversations and you're You're just an interesting dude. Well, I appreciate that, Chip. That's gonna be the beginning of this whole episode. We're just gonna put that up front. Just go game. That was awesome, Chip. Really appreciate it. Uh and thanks everyone for listening.

1:19:09 Hi everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show. at Lenny's podcast dot com.

1:19:31 See you in the next episode.

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