Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Lenny Rachitsky:Let's paint a picture of just what it was like to join Airbnb in your fifties.

Chip Conley: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.

Lenny Rachitsky:So it's great to be in founder mode. It's not as great to be working for someone in founder mode.

Chip Conley:Brian assumed everybody else was going to work at the same pace and duration. His point of view is like, hey we're having a meeting in the office tonight at 10:00, you know, be there.

Lenny Rachitsky:Everyone's talking about we gotta make the product better, we gotta optimize this button and improve conversion.

Chip Conley:Isn't the product the homes and the apartments? Joe Bot said no, product in the tech industry is something different. I just said, listen, let's get some older people who are hosts in here.

Lenny Rachitsky:This whole story is a really good example of the value of having folks that are older.

Chip Conley: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.

Lenny Rachitsky:The Airbnb experience led you to starting something called the Modern Elder Academy.

Chip Conley: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.

Lenny Rachitsky:Well, let's back up a little bit. This near death experience. Today my guest is Chip Conley. 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 was on the board of the Esselen Institute in Big Sur. At 26, he started a hotel chain called Joie de Vivre, which went on to become the second largest boutique hotel chain in the US. After selling it, Brian Chesky personally recruited Chip to join Airbnb to help Brian and the company transform from a fast growing startup to the world's most valuable hospitality brand. 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, 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, Descript, Whisperflow, Gamba, Perplexity, Warp, Granola, Magic Patterns, Raycast, Jetprd, Mobbin, and more. Check it out at Lenny'sNewsletter.com and click bundle. With that, I bring you Chip Conley. 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 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. It's everything you need to put your customers at the center of your product decisions. With a prompt as simple as, why did users choose us over competitors, Great Question not only reveals what your customers have already shared but it also makes it incredibly easy to ask them in the moment for fresh insights from the right segment. Picture this: your roadmap's clear, your team's aligned, you're shipping with confidence, and you're building exactly what your customers need. Head to GreatQuestion.com/Leni to get started. This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers, and automate compliance for SOC 2, ISO 27001, HIPAA, and more with a single platform, Vanta. Vanta's market-leading trust management platform helps you continuously monitor compliance alongside reporting and tracking risk. Plus, you can save hours by completing security questionnaires with Vanta.ai. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1,000 off Vanta when you go to Vanta.com/Lenny. That's Vanta.com/Lenny.

Lenny Rachitsky:Chip, thank you so much for being here and welcome to the podcast.

Chip Conley:Oh my God, Lenny, I sort of feel like I'm your father who's so proud of his son. He's done, he's my son has done so well and I like to talk about, tell all my friends about you.

Lenny Rachitsky:Wow, I am honored. I'm happy that I'm making you proud, Chip, and I feel the same in reverse. We got to work together for many years at Airbnb. I got to learn a ton from you. I'm really excited that more people are going get to learn from you from this conversation. 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 early career building Joie de Vivre, your time at Airbnb 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 want to talk about Airbnb where we got to work together. Let's paint a picture of just what it was like for you to join Airbnb in your 50s surrounded by a bunch of 20, 30s reporting to Brian Chesky who is, I don't know, in his 30s. What was that like?

Chip Conley:So yeah, I wasn't planning on doing this. I got a call from a woman named Natalie Tucci who worked at Airbnb and said 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? This was thirteen years ago, this was, I think it was 2012. And then Brian called me and said, listen, we really want you to come in. And so I came in and gave a talk about innovation and hospitality and I think I didn't realize it was sort of a dress rehearsal for Brian to sort of see whether the younger crowd there, I was 52, the average age was 26, would you know, feel good about, you know, an old geezer like me with a bricks and mortar boutique hotel background talking about the industry that Airbnb was disrupting? And as it turns out, people liked me. And so Brian said, want you to come in for and work fifteen hours a week as a consultant. I want you to be my in house mentor for both me and Joe and Nate. And I said, okay, you know, fifteen hours a week is great. And then within three weeks it was fifteen hours a day. And Brian and I was saying to Brian, you know, you're actually not paying me anything. They, he gave me a little bit of stock that would vest in six months. And I said, like, I don't know that this deal is working for me. This is, you seems like the company needs me a little more than you said. 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 it was hard at first, Lenny, because I didn't understand the tech lingo. I didn't have any background. I was 52. I'd never worked in a tech company before. I was mentoring Brian on leadership, but he was also my boss. I was the head of global hospitality and strategy, which 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 was involved in many parts of the business, definitely not the technical parts. But I think the hardest thing for me 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? And Joe Patt 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 required me to have a certain amount of humility as well as to be reporting to a guy twenty one years younger than me, Brian.

Lenny Rachitsky:That actually the point you're making there about what is the product I I asked Laura Hughes formerly Laura Modi what to talk to you about who we got to work together she's the CEO of Bobby now 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 everyone's talking about we gotta make the product better we gotta 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 experiences and the trips and I think that shows the value of someone like you coming in with different experience and also older and helping us communicate differently to host who also don't understand

Chip Conley:Well there's an interesting thing also Lenny and you you know this the difference in age between our hosts and our guests was probably about ten years maybe and over time it actually got higher because we started actually reaching out more aggressively to you know boomers and and gen xers to be hosts and so you had I remember one point and again let's get into product talk here I remember one point there was a conversation that was going on about taking Airbnb so it was mobile only I mean apparently because 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 nonmobile and then went mobile and then I was like oh wouldn't it be interesting if everything was mobile and at some point I just said listen let's get some older people who are hosts 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 older users in this case hosts that was helpful to you know guys and women in their twenties who are the engineers and designers and product managers and I always liked working with you I wanna just compliment Lenny oh for a minute

Lenny Rachitsky:How sweet is that

Chip Conley:And we did a lot you know we were we did a lot of different things together and what I appreciated was you you had a humility to you that 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 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 and you know I guess it would be the if the opposite side of that would be 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 was to not pretend to know things I didn't know it was to have a sense of humor and humility in how I operated and it was to show respect and hope that I got it in return and I don't know if you felt that way Lenny I you know that's that's the try the kind of environment I tried to to embody there

Lenny Rachitsky:Absolutely there's a couple of threads there I wanna follow one is just working for Brian a lot of people talk about founder mode and the power of founder mode it's so great

Chip Conley:That's how we and guess guess who'd like you know exactly with that recently that was Brian

Lenny Rachitsky:Exactly so it's great to be in founder mode it's not as great to be working for someone in founder mode often a very challenging place to be yes you reported to Brian also you were just your own boss basically your entire career you never really had to report to someone before also was in his thirties you're in your fifties what was it like working for Brian 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

Chip Conley:Well let's start with the fact that it 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 it I was like I wasn't sure I liked the 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 the business model would work although soon after joining I saw the numbers I was like wow this is working pretty well 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 2011 when the you know the big debacle happened with the the apartment getting trashed by a guest and and so Brian decided he was gonna go to find you know George Tennant the the former head of the CIA and so like Brian would go to experts and and say to the expert I don't know what the hell I'm doing and 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 wanna learn more about this so so it's sort of a growth mindset what was hard with Brian is I'd say three things number one is Brian assumed everybody else was going to work at the same 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 years on podcasts 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 was like hey we're having a meeting in the in the office tonight at 10:00 you know be there I was like really no I don't I don't think so but so so I think the the the fact that Brian assumed everybody else 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 so that was one number two is Brian admires and admired in back then Steve Jobs so much that there was a sense that as a guy who came from the product world from the Rhode Island School of Design he knew better than anybody else and so there was this you know one of the challenges for a CEO sometimes and I this is my experience in my twenty four years of running Joie de Vivre my boutique hotel company is it feels good when you feel needed and to come into a room and sort of see something and then point out the things that are wrong makes you feel good and if you don't have emotional intelligence you can that process can really piss people off or or demotivate people and in Brian's case I didn't have to deal with that too much because he didn't understand 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 I went on a world tour to 20 different cities and 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 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 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 product meeting with Brian would keep people up the night before not just because they were actually working all night long to get prepared but also that they knew they were work all night long because they probably wouldn't sleep in anticipation for this so that's that was another issue for I'd I'd say it's the other thing that you know that and and in each of these cases I think Brian's getting better 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 him I'd say the third thing for Brian was the sense that adding a zero to something in terms of expectations or thinking you you're gonna set a deadline that is unreasonable is 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 sense that Brian had that he had to maybe create ridiculous goals 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 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 lot of stress and so at the end of the day I think Brian is an a you know a generational leader for as a millennial and I think he deserves a lot of credit and Airbnb is as successful as it is partly because of Brian's leadership and I would not have been there without him 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 to leading people

Lenny Rachitsky:For people in this position a lot of people work for founders especially now that founder mode is 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 as a really good lever to work better with someone like that is there anything else you just think as tactics to be effective with founders and founder mode

Chip Conley: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 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 both what's the intention of this iteration that we're doing on the product like defines success and what do I wanna get accomplished in this meeting and you start with that 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 let's 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 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 and yeah so so try to set alignment on the front end

Lenny Rachitsky:That's a that's an important tip for anyone working with anyone even I love I love just that that works especially well here and then just going back to the credibility piece I what you shared there is you went on this world tour not something everyone can do but just like getting really close to your customers 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

Chip Conley:Yeah and don't and and I think the other thing is PowerPoint or 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 a combustible founder who may take you off path such that your deck in its current order makes no sense at all so that 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 to just sort of set principles set goals but yeah

Lenny Rachitsky:So this whole story of you joining Airbnb in your fifties is a really good example of of 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 then we segue into other elements of your career

Chip Conley:I wrote a book called Wisdom at Work, The Making of a Modern Elder after my Airbnb experience and I did a lot of research. I was like wow, so why do we have 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 realized that a younger brain has fluid intelligence, tends to be fast and focused, really good at problem solving, very good at linearity in terms of looking at things. As you get older, the brain shrinks a little bit and you have crystallized intelligence. And in crystallized intelligence, what's going on is your brain, you're going from the left brain to right brain more adeptly, there's a little bit less focus, a little more holistic thinking, systemic thinking, connecting the dots. So you can imagine that on a team, when you have older brains connecting the dots, thinking broadly, peripherally, younger team members being really fast and focused 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, Laura Hughes Modi, who was my director of hospitality but also we worked in so many different capacities with her in the company, I loved working with her because her brain worked different than my brain. And 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 brain diversity, not just with neurodiverse people but age diverse people, you get a benefit, an effective benefit that is not as noticeable quite frankly in some other diversities. 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, one of the things I said to Brian early on was, you know, I've seen the business plan now, I know the goals of how big we wanna 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, we're not paying it and we're trying to do everything we can not to pay it knowing 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, 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 is I said to 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 toward building a strategy for how we're gonna be regulated. And that's 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, 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 ever since I was there. And there's a few other markets in the world where it was like that. So I would just say, you know, the value in having some age diversity, 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, you know, an engineer who you, I think you probably remember him right at Airbnb. So this is a guy who looked younger than he was and he was a little bit nervous about telling people his age. But the thing that was great about John is over time he was not necessarily gonna be the best coder at Airbnb. There was a whole new collection of coders coming in every month, but he became a great manager. And the beautiful thing about moving from the individual contributor to the manager, the person who can actually bring out the best in a bunch of younger people who may be better technically than he or she is, but they know how to elevate talent. I call this invisible productivity. 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 be the kind of person who wasn't solving all the problems but I was trying to elevate. There's a woman named Lisa Debost who is at Airbnb and she one day the HR department was reporting to me at one point and she was running HR, she was 25 and had no background in HR at all. And one day she came in to me and she just said, Chip, you are my confidant. And Lisa, Lisa has a French accent and you know, fluent in French and she said, so she said confidant in just the right way. And I said, oh, well thank you Lisa. But I said to her, you haven't given me any juicy details yet, like a confidant is someone who has the secrets. And she said to me, no, in my part of France, a confidant is somebody who gives you confidence. 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.

Lenny Rachitsky:So you're sharing a lot of really good examples of the value of older folks being within tech companies. So let me just ask you this, how real is ageism in tech? And I ask because a lot of people that are hiring are probably thinking 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?

Chip Conley:Yeah, it, you know, it's clearly a problem. I'd say it's maybe a little bit less of a problem than it was a dozen years ago because I think a dozen years ago was almost a blind spot. You know, 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, which is good because it means that there's a voice and a way to congregate with a bunch of people who are older. Ultimately, 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 challenge is 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 set of skills that an older person doesn't have, the older person is both expensive and maybe perceived as slow. So in the era of AI, it's a whole new ballgame. And the question I think will be, if what AI cannot do is the human wisdom piece, artificial intelligence and human wisdom might be the balance beams here. Is it possible that older managers who have a little more emotional intelligence, a little bit more pattern recognition, a little bit more wisdom can be a value to a company? And so it's still the jury's still out. There's a New York Times article that just came out about the question of is AI gonna wipe out older people's jobs or younger people's jobs? And I think the answer is both. But the question is how much, how bad is it for both of them? And I think what I would say to an older person, and when I say older, I mean like 45 or older, 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 down to 40% or 50%, and my stock, my options were to that level, my salary dropped to that level because I didn't wanna work full time anymore. And there are a lot of people who can be valuable in a company who have some institutional wisdom, some process knowledge of how to get things done in this organization. And in tech companies, that's really important. Airbnb, one of the biggest challenges that Airbnb has always been is how do I get shit done around here? And process knowledge allows you to understand how do you deal with an org chart and get things done, partly because you understand the motivations of different groups. And that is something you build over time. Long story short is I just think that older people might look at their workload and say I'm willing to take a 20% or a 40% pay cut to go to 80% or 60% time and the company is gonna get their money's worth in that.

Lenny Rachitsky: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 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, 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. 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 do they have in common that other folks you think should work on and focus on?

Chip Conley:I think this idea of being a mentor and a mentee and an intern, there's just the voracious appetite for curiosity. When I talk to someone 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. Energy is they notice that you are not just sort of resting on your laurels, you have physical energy in how you do your job. And when people are like that, they are sort of timeless, they are age fluid, as I say, talk about gender fluidity, well this could be age fluidity. They don't, they're not defined by their age. But the other part of energy that's important is 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. 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, 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 feeling was really important. And so my energy, both the positive energy part and then also the fact that yeah, I could work sixty and seventy hours a week and I could travel around the world as the secretary of state of the company, which is what Brian called me a couple 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. Well maybe some people pulled the board but 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 are younger than you and you're gonna probably do pretty well.

Lenny Rachitsky:That is really great advice. Today's episode is brought to you by Coda. I personally use Coda every single day to manage my podcast and also to manage my community. It's where I put the questions that I plan to ask every guest that's coming on the podcast. It's where I put my community resources. It's how I manage my workflows. Here's how Coda can help you. Imagine starting a project at work and your vision is clear. You know exactly who's doing what and where to find the data that you need to do your part. In fact, you don't have to waste time searching for anything because everything your team needs from project trackers and OKRs to documents and spreadsheets lives in one tab, all in Coda. With Coda's collaborative all-in-one workspace, you get the flexibility of docs, the structure of spreadsheets, the power of applications, and the intelligence of AI all in one easy to organize tab. Like I mentioned earlier, I use Coda every single day and more than 50,000 teams trust Coda to keep them more aligned and focused. If you're a startup team looking to increase alignment and agility, Coda can help you move from planning to execution in record time. To try it for yourself, go to coda.io/lenny today and get six months free of the team plan for startups. That's coda.io/lenny to get started for free and get six months of the team plan. Coda.io/lenny. Interestingly, curiosity comes up a lot when I ask AI forward people what are they focusing on helping their kids learn most. Curiosity is the most common way to describe. So at every stage of life, curiosity is something to cultivate. I want to go to the flip side of companies looking to hire. It feels like there's this untapped supply of awesome people that companies with ageism and tech 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 hire that might help them find these people?

Chip Conley:I think we're moving into, there's a book that David Epstein wrote called Range and the whole premise of Range is that we are moving out of the era of the specialists and into the era of the generalists. And I think AI is just accelerating this. As we are more reliant upon AI and AI can be exceptional at technical skills and solutions 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 or recruiting is beyond what I already said before is, is the person passionate? Are they curious? Are they a learner? Do they have good energy? But I would also say are they a generalist when they're a problem solver because I actually think that's gonna be an increasingly important part of how effective companies think broadly. So I think that's a key one. I think also this idea of how do you create intergenerational collaboration in the form of mutual mentorships. One of the things I loved at Airbnb, there were a few people I did this with where I had something to teach them and they had something to teach me. So good example, my iPhone. So there's 97% of the utility of my iPhone that I probably don't use and don't know how to use. This is, you know, back in let's say 02/2013, 02/2014. And so there are people who knew iPhone or Google Suites back then. I never used a Google Doc back then when I joined Airbnb. So there were people who could teach me something technical and then they wanted to learn something from me which would be like how do you run a great meeting or how do you give a great employee review. There are a lot of managers who've never been a manager before. And so how do you disperse people like me in the organization 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, you're an electrician apprentice not because you're watching some video on it, you're out there in the field doing it. And that's a huge value in a younger company when you have some older people who have not been invested with responsibility of managing those younger people because they may didn't have, they may actually be reporting to someone younger than them, but they're there to actually be support. And in some ways, I think that was part of the unexpected value that I was able to offer to Airbnb and to Brian specifically because there are a ton of people in Airbnb who were not even in my departments who would come to me and say I'm having a problem, how do I solve this? Can we spend lunch together? And you know, I almost always said yes.

Lenny Rachitsky:I think the reason people did that in many ways is you just have a very unique aura of wisdom and it's hard to replicate that, Chip.

Chip Conley:Yeah, I mean yes, and it all comes back to curiosity. If I was just the older elder dispensing wisdom, people would have gotten bored very quickly. And I think the fact, yeah, yeah, I mean I was on the board of Burning Man. Oh, that's cool. And so there was a, I show up as someone who feels younger than I am. I mean, I'm turning 65 this year. So the bottom line is I think people lost track of my age partly because I lost track of my age.

Lenny Rachitsky:That's such a good, such good advice on the front end to be successful as a person kind of getting older in tech is curiosity, positive energy, the way you talked about it, passionate engagement, is that the term? Yep. And then on the other side is hire generalists. This actually comes up a lot in the AI conversations exactly as you said, the power of generalists. It reminds me, I'm going to this gym now and a lady there is just like I love AI so much because I'm just such a big picture person. I get so bad at just getting thinking about the details and AI solves all that for me. It's like here, here's what I wanna do, I'll do this, move my house to here, here, and it's like here's what you need to do step one, two, three, four, five.

Chip Conley:It is remarkable. I mean since the time I've known you how fast it has become dominant in our lives. But yeah, I think one of the last things I'd say is I'm privileged. So for those of you who are listening or watching this and you're saying, well, you know, Chip, you were 52 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 could have been plucked and brought in and partly 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. And there are lots of people who Brian brought into the company who didn't work well. So I think the key is how do you get the foot in the door? And at the end of the day, you know, the second and third order of degrees of separation in terms of networking is are still essential. But the most important thing is to be able to articulate what you have accomplished in a new way that a recruiter says wow. And so I really tell people like I would love to see a resume. First of all, the question that I think it was, who was someone asked it, I don't remember if it's Sheryl Sandberg 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 what I love to see is not so much what roles you've had, what bullet points do you have of yours, like things you've learned. Give me in a paragraph a thorny problem you faced, what was the problem and how you got, what skills you used to actually accomplish it and what was the result of that. 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...

Lenny Rachitsky:Love that word. I love that we're getting into interview advice and resume advice. Yes, speaking of thorny problems and also why Brian decided to reach out to you, wanna go back to the beginning of your career? Yes, so you're out of business.

Chip Conley:You're good at this by the way, you're good at this.

Lenny Rachitsky:I was thinking ahead okay so you're in business school you left business school you're like maybe I should start a hotel something that rarely works out usually probably leads to a lot of money lost 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 Girardeau Vie beloved I loved every single experience I've had at Girardeau Vie when you sold it I was like that is so sad talk about just story I know this could go on for hours but what's

Chip Conley:The yeah I'll be I'll be brief yeah 26 years old couple years out of Stanford business school working for commercial real estate developer I was bored silly I wanna do something more creative Bill Graham famous concert promoter said to me you know I because I gotten to know him what San Francisco really needs is a rock and roll hotel so I decided to start looking to to find a broken down motel hotel that I could turn into a rock and roll hotel and I found something in the Tenderloin and and turned it into the Phoenix which became a famous rock and roll hotel that I have owned for thirty nine years now so long story short is that was how I started Joiradiv and the company and we grew to 52 hotels around California became the second largest as you said in the in the world in terms of the number of hotels boutique hotels that we operated and I loved it till I hated it in my late forties I hated it didn't wanna 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 chrysalis but a midlife crisis where I just wanted to change everything and I got through it I had an NDE at at 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 you know I decided to sell my company at the bottom of the great recession so that's so that was really how I created this space in my life to be able to join Airbnb

Lenny Rachitsky:Well let's back up a little bit this near death experience share more there what happened there

Chip Conley:Yeah I was so I write books I've written seven or eight books and I had written a book called Peak How Great Companies Get Their Mojo from Maslow and it was a book that Brian really liked and part of the reason he he wanted to reach out to me I was on a book tour I had a broken ankle I broke my ankle at a bachelor party playing baseball and I ended up with a cut on my leg and the cut on my leg had fertilizer in it and went septic and so I was on a very strong antibiotic and I died I went flatlined from the 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 ended up in the hospital for a couple three days and they finally said listen it's an allergic reaction we believe they thought it was I thought they thought it a heart attack they had a bunch of stuff stroke etcetera nope it was the allergic reaction so but you know I saw birds I mean I I saw all this beautiful stuff I we don't have time to go into it what I did you wanna hear this yeah know saw all this beautiful stuff let's do it the the best I I think there's a hotel in San Francisco called the Vitale that I built across street from the Ferry Building and it's still there but it's no longer called the Vitale in that hotel there were these slippers in every guest room one slipper said slow the other slipper said down and so I was wearing these slippers in my flatline thing flying in in the air in a 40 foot tall living room in the Alps surrounded by birds that were twer tweeting and and chirping at me and I understood bird talk 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 awe and there was a bunch of other things but let me just 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 you know 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

Lenny Rachitsky:Holy shit I love that this was like there is a message inside of this experience I don't know how many people experience that clearly 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 Gerard Vie

Chip Conley:At that point I've been running Gerard Vie for twenty two years and

Lenny Rachitsky:Twenty two years and it's interesting that you need something like that a lot of times otherwise it's just momentum keeps carrying you forward

Chip Conley:Yep within two years I'd sold it and I had the chance to move on

Lenny Rachitsky:So with building Joie de 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 which also came out at Airbnb talk about just why you see culture as such an important part of how you build a business like tangibly because a lot of people talk about culture warm fuzzy stuff but you think about it very tangibly

Chip Conley:Culture is what happens around here when the boss is not around and the more distributed a company the more culture is important because the boss is around in a traditional bricks and mortar workplace where everybody shows up at eight and leaves at six and we all see each other but at in my company in Joie de Vie we had 52 hotels and 25 restaurants and four spas and it was distributed so I couldn't be in all those places all the time and same similar with Airbnb I mean 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 when you're remote 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 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 so Oracle has a different you know 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 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 saw it at Airbnb all over and over again in in fact Airbnb saw it I think when with Amazon people Apple people have resonated pretty well at at at Airbnb Amazon people less so and those are two different cultures Amazon and and Apple and therefore understanding a culture before you even actually take the job is one of the more important decisions you need to make it's like is this culture a culture that I can live with and maybe influence there's language about culture fit I like to say culture add because culture fit to me means can actually be quite negative toward somebody who is the aberration you have to fit in and especially if this is like a demographic thing a person of color a gay person a person in a wheelchair so you have to fit in 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 you still have to be able to get along in that culture so 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 pull employee pulse reports and things like that

Lenny Rachitsky:You talk about having to understand the culture is such a 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 worked part time it's easier to experience at all any tips there for like okay this is for me this is not for me

Chip Conley:When you're interviewing you're 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 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 in terms of something that's just endemic or sort of baked in across the organization and is it ever going to get fixed and how could I come in and maybe help that which frankly at a very junior level you're not gonna be able to help it except for in very minor ways if you're a senior person you might be able to help it so these are these are the kind of questions I'd wanna know and frankly 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 and if I'm not is that because there's not alignment is that because different departments have different flavors because you could have a culture within a department that's very different than the overall corporate culture the corporate culture certainly has an enormous oppressive influence but you know you can you can you can be in a culture a really great culture of a team or a department in an overall company culture that's not good in the long run that oppressive company culture is either gonna have to evolve or your department you may lose people

Lenny Rachitsky:When I reflect back on the impact you had at Airbnb one of the funny things I think about is triangles showing up a lot on decks and specifically rooted in Maslow's hierarchy just like everything's this Maslow hierarchy metaphor true and this one I don't know specific piece of this is you have this kind of model you think about for how to help employees be successful at a company it's kind of rooted in your Peak book philosophy maybe just talk about that and then if there's anything else you wanna expand on with this power of thinking through the Maslow hierarchy

Chip Conley:So you know Maslow's hierarchy basically five levels later in life he had a seven and an eight level model but you know at the base is you know physical you know the kind of physical water food air and you move up to self actualization at the top so

Chip Conley:To use this model as a hierarchy of needs for employees, customers, and investors is what the peak model is about. The peak, my book, the employee model is really simple: it's money or compensation at the base, recognition in the middle, and meaning at the top. Now, there are some industries and some kinds of jobs in which money is 90% of the pyramid, so just because it's the base doesn't mean it's not the dominant part of the pyramid. But the differentiation often is in recognition and meaning. In nonprofits, usually the money piece is rather thin and the recognition and meaning is huge. So understanding how do you create an organization, and I gave a TED talk in 2010 about this topic as well, how do you create a, how do you measure the intangibles of meaning and how do you create an environment where people feel a sense of meaning. The customer pyramid briefly, I'll just say that one is meeting expectations is the base, 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 Goldenhall was joining is we really tried to ask ourselves, are we in the home sharing business or are we in some kind of business that is even bigger and broader than that? And ultimately, we came up with the idea that we were in the belong anywhere business. Airbnb was not in home sharing, we were in belonging anywhere. So once you have that 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, how does our marketing and advertising play up the belonging piece especially, and the everywhere piece because hotels are not everywhere but homes are. And so I would just say that this model, the idea of hierarchies, is I think very helpful. And yeah, my book Peak has been out for eighteen years but I still am asked to give 20 or 30 speeches a year on it.

Lenny Rachitsky:Oh man, this pyramid of comp, recognition, meaning is really interesting especially these days because like with all this AI researcher poaching there's all this talk of just like will people just go work wherever they get the most money or is there a mission and meaning to the work they're doing that will keep them not taking a $100,000,000 offer and seems to be happening in a lot of cases which shows you the power of meaning.

Chip Conley:Yeah, I mean 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. Yeah, life is too short.

Lenny Rachitsky:Okay, so you've had two major shifts in your career. You started the hotel chain, you went to then you went to Airbnb. Most recently the Airbnb experience, I imagine, led you to starting something called the Modern Elder Academy. Talk about what is the Modern Elder Academy.

Chip Conley:Yeah, what is going on with that Modern Elder Academy? The Modern Elder Academy. So there were a couple times where I was called the Modern Elder at Airbnb and then I was told that a Modern Elder is someone who's as curious as they are wise. So Jonathan Mildenhall, who is the Chief Marketing Officer at Airbnb, used to call me the Modern Elder as well and he said if you ever create a school, you know, 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 it MEA because elder is a fraught word on some level, it makes you sound elderly. But what I really wanted to create was a place where people could come and do a workshop, you know, their five-day workshops in Baja on the beach or in Santa Fe on a big four square mile horse ranch and reimagine and repurpose yourself and navigate transitions. We go through so many transitions in the middle of our life, let's say between, I define midlife as 35 to 75 guys, so like this is a very long life stage. So we go through a lot of transitions, we are constantly evolving our purpose, 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 Becka 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 which is more life than any other biohack that's being done right now. So that's what we do and we have 7,000 grads from 60 countries and 56 regional chapters around the world. So it's a bit of a movement and I teach, 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 natural next thing for me to do. I love hospitality so it's a very upscale kind of experience but we have scholarships. I love retreat centers. I was on the board of the Esselen Institute in Big Sur for ten years. I love wellness. I've owned the Kabuki Springs and Spa for twenty-eight years which is the largest spa in San Francisco and I love education. And my book Wisdom at Work to Make You Never a Modern Elder gave me a curriculum in which we've expanded quite a bit with Harvard, Yale, Stanford and UC Berkeley professors helping us a greater curriculum around midlife. And so that's how MEA came about.

Lenny Rachitsky:To your point, forget who said it, I think you said Jonathan has said this was a 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 Esselen and I knew just keep getting more interested.

Chip Conley:Thank you.

Lenny Rachitsky:There's a couple threads here I wanna 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?

Chip Conley:Yeah, there's a couple, there's lots of data points. I'm just gonna, I'll talk about two. One is this Becka Levy study which has been going on for fifteen to twenty years. If you sort of buy into the ageism of American society or Hallmark cards when you get a card at age 40, 50 or beyond, there's a belief that life gets worse as you get older. And if you can survive your midlife crisis, all you have to look forward to is disease, decrepitude and death. And the bottom line is, 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: 12 reasons why life gets better with age. And what I really wanted to do with that book, which is really it summarizes the MBA curriculum, I wanted to write a book that sort of helped people to see the upside of aging, the unexpected pleasures of aging 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 upside of aging, you take better care of yourself both your mind and your body. 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, you know, all of your life left ahead of you. But when I moved to Baja part time in Mexico at age 56, 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 ten years from now, what will I regret if I don't learn it or do it now? 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. So 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 and it's been around for twenty years and it shows the following. It has changed in the last couple years because young adults are unhappy like never before. So a 20 year or a 22 year old really unhappy, 24 year old really unhappy. But historically the way it was is you were happy from 18 to 23 or 24 and then around 23 or 24 you start to see a long slow decline in life satisfaction that actually bottoms out between 45 and 50. I'm sorry to tell you that Lenny since you're 44 but your mileage may vary.

Lenny Rachitsky:So you're saying I'm the least happy I'll ever be? Like that's only upside, that's great.

Chip Conley:Well here's the part that's weird is that when before this research was done and it's global research across all demographics what they found was starting around age 50 or 52 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 eighties happier than seventies. So wow and it's partly because we are in around 45 to 50 doing this thing called the midlife unraveling what Brené Brown calls the midlife unraveling. You're unraveling your expectations, your what you define as success, your definition of what a beautiful body looks like and you get some you're liberated into freedom in your fifties and beyond and I can say that yeah I'm happier today at 64 than I was at 47 when I was going through my flatline experience and not wanting to run my company anymore.

Lenny Rachitsky:You used this term earlier the midlife chrysalis, was that what it was?

Chip Conley:Or chrysalis, chrysalis.

Lenny Rachitsky:Chrysalis, what is that? Is that kind of along the same lines?

Chip Conley: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 life my life is liquefying in front of myself but you know on the other side of it there's a metamorphosis that happens and so i i like to use the language in fact i have a podcast called the midlife chrysalis because i wanna help you know change the dialogue around midlife so that the number one word attached to midlife is not crisis but in fact it's maybe chrysalis and the idea that life is meant to be transformative during that era

Lenny Rachitsky:That is actually very empowering i am sort of going through that not necessarily in this intense way yet but that might be common 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

Chip Conley:Emotional intelligence grows with age our wisdom can grow with age although we know 70 year olds who are not as wise as 30 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 what else gets better with age you learn how to edit you you you have no more f's left to give no more fucks left to give there that is absolutely true especially for women as they age you are more spiritually curious you're i mean the list is long and and so there are a lot of things that actually another one that i love is you're not compartmentalized when you're younger you're compartmentalized as you grow older you are growing whole and that means you're alchemizing curiosity and wisdom introvert extrovert masculine feminine gravitas depth and levity lightness and the people who i really admire who are 85 years old they're so present and they're so whole they're like they are just who they are

Lenny Rachitsky:There's a quote i found from you along these lines the societal narrative on aging is just don't do it yeah

Chip Conley:There that's i mean we sort of say like 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

Lenny Rachitsky:Coming back to mea just for folks that are interested curious about this who is this for would you say who should seriously look into this program

Chip Conley:Mea is really the people who tend to come to mea are in the midst of a transition it could be selling their company leaving a job getting divorced having kids becoming an empty nester taking care of parents till they're passing away having a health diagnosis that's scary so average age is 54 and it's people of all walks of life so it's not just the tech industry but a lot you know it's very popular in the tech industry it's people who are looking to maybe do a reframe of their purpose and maybe even a reinvention of their career and so yeah and and the two campuses are just gorgeous they've it's been called the 4 seasons meets blue zones meets the esselin institute which i like and we do 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 new mexico you can actually do it online

Lenny Rachitsky:Those three yeah that's the tagline that's your tagline right there sln meets blue zones meets what what was the first one

Chip Conley:The four seasons

Lenny Rachitsky:The four seasons yeah nailed it okay i'm gonna zoom out and take us to a recurring segment on this podcast i wanna see if this goes anywhere ai corner and with ai corner ask guests just what's a way that you've found ai useful in your work or in your life any kind of trick you've learned any workflow anything you found useful

Chip Conley:Yeah you know i i have a daily blog it's called wisdomwell and it's on the mea website and when i'm looking for inspiration you know ai does it for me and 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 so if i have a deadline for tomorrow and it's 05:00 in the afternoon it's like okay chatgbt i'm on my way to you and i tend to use chatgbt the most because i don't know i mean i like clot as well but yeah

Lenny Rachitsky:Okay awesome i was gonna ask which tool you use 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

Chip Conley:The good news is that at this point it knows me well enough and my and my blogs and i've actually you know it it it knows my my sort of weird sense of humor so it's able to ape me pretty well so i'll just say i need a 250 word post on like today the you know today's post was a post that chat gbt helped me with it i said i believe that there's a a a refrain that needs to happen with soul we tend to say like i have a soul or i don't have a soul but what if this my soul has me what if in fact my job is just to be this vehicle for my soul to go to the next lifetime and my so my job is to be the steward of the soul and i said write me something around that and so it's just a weird idea and of course my not all my blog posts are so new age and and like that i i i write a lot on leadership but that was one that you know within you know thirty seconds i had a 250 word you know blog post that i then adapted and there you go amazing

Lenny Rachitsky:Chip we've covered a lot of ground we've gone through your entire life maybe actually just the tip of the iceberg with that we've 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

Chip Conley:My favorite book of all time man's search for meaning Viktor Frankl 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 yeah but it also really speaks to this idea of despair equals suffering minus meaning I wrote a book called emotional equations it 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 of me so that's one I you know I love any book by Liz Gilbert sort of the opposite so Elizabeth Gilbert wrote eat pray love her her book she's a she's on faculty at MEA she teaches here big magic is just a beautiful book about sort of like how do you get in the flow to allow the genie to come through you her TED talk in 2009 was about the fact that genius is not about being the genius yourself it's about being the receptacle for the genie that come through you

Lenny Rachitsky:I wanna come back to this equation you shared I was gonna get to it but I didn't so this is a good opportunity to you so there's a couple of that are really interesting to me this is you wrote about these in a book yeah 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

Chip Conley:That's right so suffering suffering this sort of Buddhist philosophy the first noble truth of Buddhism is that suffering is ever present and so if suffering is a constant and you have two variables using some algebra I guess you know that if you have more meaning you have less suffering and so that's that one

Lenny Rachitsky:The other one that I love is anxiety equals uncertainty times powerlessness maybe talk about that one briefly

Chip Conley: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 you can create an anxiety balance sheet and you know create four columns first column is what is it you do know about this thing that's making you anxious the second column is what is it you don't know the third column is what is it you can control or influence and the fourth column is what is it you can't control or influence and when you take free floating anxiety and put it into a an equation it actually makes it more tangible and you often are less anxious as a result

Lenny Rachitsky:Boom okay so if you're feeling anxious right now this is an exercise you can do and you'll feel less anxious in five minutes is what I'm saying okay excellent very very good negative advice okay let's keep going with the lightning round come back for mark tangent do you have a favorite recent movie or TV show you've really enjoyed

Chip Conley:I mean Ted Lasso is I meant like a sucker for for for that show you know when it comes to movies I'm a total movie buff I we have an annual MEA film festival at our Santa Fe campus and I would say that the film that I'm most excited about that is coming out that most people have never heard of is called I'll Push You and it's the story of two guys one of whom is in a dead degenerative health condition and in a wheelchair and his best friend pushes him the 500 miles of the Camino de Santiago and it's the relationship they build along that way

Lenny Rachitsky:Amazing very deep cut do you have a favorite product that you you recently discovered that you really love

Chip Conley:Yes hair growing material no you know Viori shorts I I you know I sound like Scott Galloway because he he advertises this but Viori shorts are like I just love them you know

Lenny Rachitsky:They're just breathe and they're comfortable I'm wearing Viori joggers right now the one downside of Viori and 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 I don't know yeah but I do love there's nothing better that's the problem I haven't done anything else like this that is all cotton yeah yes but I'm a fan I have many Viore I don't know if they're called joggers just I don't know weekenders or something anyway love you Viore okay do you have a favorite life motto that you 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

Chip Conley:I mean my favorite one right now is your painful life lessons are the raw material for your future wisdom and the premise of that is that wisdom often comes through the school of hard knocks 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

Lenny Rachitsky:Okay final question you were on the board of Burning Man or you still are

Chip Conley:I helped found the board of Burning Man yep

Lenny Rachitsky:Okay no big deal so I don't know if you know this I got married at Burning Man we had an unofficial wedding there on bicycles so it's really meaningful to us I've been there four or five times what's something about Burning Man that maybe people don't know some inside story or a really unexpected piece of this the journey I imagine there's a lot but what comes to mind

Chip Conley:I would say the best not well known thing about Burning Man is that Burning Man owns a place called Fly Ranch and Fly Ranch is about 10 miles from Burning Man. Now if when you go to the burn the event in you know around Labor Day you cannot go over there. It's locked off, it's 3,400 acres but if you do if you look at Fly Ranch flyranch.org I think it might even be or it's on the Burning Man site. Fly Ranch is like the opposite of Burning Man. Burning Man is this alkaline desert like there's no living life there at all it's very masculine. Fly Ranch is like porous and like lots of desert grasses and hot springs and hot pools and it and birds and wild horses and it's one of my favorite hot springs places in the world so just check it out and you can go there when it's not during the event and it's quite beautiful.

Lenny Rachitsky:Feels like it might have inspired MEA in many ways.

Chip Conley:It did yes Chip two.

Lenny Rachitsky:Final questions where can folks find you online and how can listeners be useful to you?

Chip Conley:So online meawisdom.com is the website for MEA. My website's chipconley.com c0nley and 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 your community can do just yeah come say hi come check me out and if wisdom is interesting to you and I think wisdom should be interesting to everybody here on the MEA 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 and there's also a free resource down there called the anatomy of a transition those two free resources 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.

Lenny Rachitsky: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.

Chip Conley:I don't know why because I'm a little too Burning In.

Lenny Rachitsky:You're just yeah exactly it feels like that's not your vibe but I love that you do it because that's where the people are.

Chip Conley:Oh I put wild weird stuff up on LinkedIn and you know thank thank God somebody's doing that.

Lenny Rachitsky:I got for some reason don't see it I need to fix that Chip this was incredible everything I was hoping it'd be thank you so much for being here and for sharing.

Chip Conley:Thank you Wendy.

Lenny Rachitsky:Your wisdom.

Chip Conley: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 I really when whenever you were assigned to a prod 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.

Lenny Rachitsky:Well appreciate that Chip that's gonna be the beginning of this whole episode we're just gonna put that up front just joking that was awesome Chip really appreciate it and thanks everyone for listening bye 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'spodcast.com see you in the next episode.