Chip Conley: Why midlife is a chrysalis, not a crisis

1. 0:00 – 4:30

   Introduction to Chip Conley

   1. LRLenny Rachitsky0:00

      Let's paint a picture of just what it was like to join Airbnb in your 50s.

   2. CCChip Conley0:04

      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.

   3. LRLenny Rachitsky0:14

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

   4. CCChip Conley0:17

      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 o'clock. You know, be there."

   5. LRLenny Rachitsky0:28

      Everyone's talking about, "We got to make the product better. We got to optimize this button and improve conversion."

   6. CCChip Conley0:32

      "Isn't the product the homes and the apartments?" Joe Bhatt 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."

   7. LRLenny Rachitsky0:41

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

   8. CCChip Conley0:45

      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.

   9. LRLenny Rachitsky0:55

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

   10. CCChip Conley0:58

       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.

   11. LRLenny Rachitsky1:09

       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 will ever meet. He was a founding member of the board of Burning Man. He was on the board of the Esalen 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, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, ChatPR, DeMob and more. Check it out at lennysnewsletter.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 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. 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/lenny 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 risks. 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 V-A-N-T-A dot com slash Lenny.

2. 4:30 – 11:44

   Chip’s journey with Airbnb

   1. LRLenny Rachitsky4:32

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

   2. CCChip Conley4:38

      Oh my god, Lenny. I- I sort of feel like I'm your father-

   3. LRLenny Rachitsky4:41

      (laughs)

   4. CCChip Conley4:41

      ... who's so proud of his son. Has done-

   5. LRLenny Rachitsky4:43

      Aw.

   6. CCChip Conley4:43

      ... just, my son has done so well, and I, I like to talk about, tell my friends about you. (laughs)

   7. LRLenny Rachitsky4:49

      Wow. Uh, I am honored. Uh, I'm happy that I'm making you proud, Chip, and I feel, I feel the same in reverse. Uh, we got to work together for many years at Airbnb. 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. 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 Joie de Viv, your time at Airbnb where we got to work together, and then talking through what you're working on now at 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. Let's paint a picture of just what it was like for you to join Airbnb in your 50s. Uh, surrounded by a bunch of 20-something, 30-somethings, reporting to Brian Chesky, who is, I don't know, in his 30s. What was that like?

   8. CCChip Conley5:41

      So yeah, I- I 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, "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?"

   9. LRLenny Rachitsky5:59

      (laughs)

   10. CCChip Conley6:00

       This was, uh, 13 years ago.

   11. LRLenny Rachitsky6:02

       Love it.

   12. CCChip Conley6:02

       This was, I think it was the end of 2012. And then Bryan called me and said, "Listen, uh, we really want you to come in." And so I came in and gave a talk about innovation in hospitality, and, and I think, I, I didn't realize it was sort of a, a, a dress rehearsal for Bryan to sort of see whether the younger crowd there, um, I was 52, the average age was 26, would, you know, feel good about, you know, uh, an old geezer like me with a bricks and mortar boutique hotel background, uh, talking about the industry that Airbnb was disrupting. Um, and as it turns out, people liked me, and, um, (laughs) so, uh, Bryan said, "I want you to come in for, and work 15 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, 15 hours a week is great." And then, uh, within three weeks it was 15 hours a day, and, (laughs) and Bryan w- a- and I was saying to Bryan, you know, "You're actually not paying me anything." (laughs) Um, y- they gave me s- s- uh, a little bit of stock that would, would vest in six months, and I said, like, "I don't know that this deal's working for me. Um, this is y- you n- it seems like the company needs me a little more than you said." And, and he said, "Yeah, I gotcha. (laughs) Uh, 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, I didn't have any background. I was 52. I'd never worked in a tech company before. I was mentoring Bryan on leadership, but he was also my boss. I was the, um, head of global hospitality and strategy. Uh, so which meant s- meant initially I was in charge of all the hosts in the world. Over time, that w- like, you know, that meant a lot more things too. I, I was involved in m- 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 bought ... said, you know, "I'm the chief product officer," and I'm like, "Well, isn't the product (laughs) , isn't the product the homes and the apartments?" And Joe bought, 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, as well as to be reporting to a guy 21 years younger than me, Bryan.

   13. LRLenny Rachitsky8:36

       That actually, the point you're making there about what is the product, I, I asked, uh, Laura Hughes, formerly Laura Modie, what to talk to you about, who we got to work together, she's the CEO of Bobby now, uh, you worked 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 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 different experience and also older, a- and helping us communicate differently to hosts who also don't understand.

   14. CCChip Conley9:15

       Well, there's an interesting thing also, Lenny, and you, you know this, is the difference in age between our hosts and our guests was probably about 10 years, maybe, and over time it actually got higher, um, because we started actually reaching out more, uh, aggressively to, you know, Boomers and G- and Gen Xers to be hosts. And so you had, I remember at one point, um, and again, let's get into product talk here, I remember at one point th- there was a conversation that was going on about taking Airbnb so it was mobile only, um, I mean, b- partly 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 non-mobile and then went mobile, and then it was like, "Oh, wouldn't it be interesting if everything was mobile?" And at some point (laughs) , I just said, "Listen, uh, 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, uh, users, i- in this case hosts, um, that was helpful to, you know, gu- guys and women in their 20s who were the engineers and designers and product managers, and, um, I always liked working with you. I wanna just compliment Lenny-

   15. LRLenny Rachitsky10:37

       Oh.

   16. CCChip Conley10:37

       ... um, for a minute-

   17. LRLenny Rachitsky10:38

       How sweet is that?

   18. CCChip Conley10:39

       ... because, 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 they're, 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. 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 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 y- you felt that way, Lenny. I, you know, that's, that's the tri- the kind of environment I tried to, to

3. 11:44 – 18:27

   Insights on working with Brian Chesky

   1. CCChip Conley11:44

      embody there.

   2. LRLenny Rachitsky11:45

      Absolutely. There's a couple of threads there I wanna follow. One is just working for Bryan. A lot of people talk about founder mode, and the power of founder mode, it's so great, that's how we-

   3. CCChip Conley11:55

      Oh, and, and g- and guess, guess who, like, you know-

   4. LRLenny Rachitsky11:57

      Exactly.

   5. CCChip Conley11:57

      ... populated that recently?

   6. LRLenny Rachitsky11:58

      Exactly.

   7. CCChip Conley11:58

      It was Bryan.

   8. LRLenny Rachitsky11:59

      (laughs) 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.

   9. CCChip Conley12:07

      Yes.

   10. LRLenny Rachitsky12:08

       You, you reported to Brian. Uh, also you were just your own boss, basically your entire career. You never really had to report to someone before. Also, he was in his 30s, you're in your 50s. What was it like working for Brian? Uh, you know, like, the more real you can be, the better. 'Cause a lot of people I always talk about here is like, "Oh, it was wonderful. I learned so much." Just like, what was that experience like? What did you learn from working for someone like Brian?

   11. CCChip Conley12:30

       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 amo- the business model would work, although soon after joining, I saw the numbers and 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, um, the- the apartment getting, uh, trashed by a guest, and- and so Brian decided he was gonna go to find, you know, George Tenet, 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." 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 e- to say, "I wanna learn more about this." So, it's sort of a growth mindset. What was hard with Brian is, I'd say three things. Um, 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- the beautiful thing about Brian is he's been very honest in the last couple of 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." (laughs) I was like, "Really? No, I don't- I don't think so." But, so I- so I think the- the- the fact that Brian assumed everybody else wa- was as one-dimensional in their focus as him was, at times, a problem. Especially for a guy like me who was, I was in a stage of my career where like, I have a lot of interests. Um, 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, uh, 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 24 years of running Joie de Vivre, my boutique hotel company, is it feels good when you feel needed. Um, and to come into a room and sort of see something and then point out the things that are wrong makes you feel good. A- and if you don't have emotional intelligence, you can h- that process can really piss people off or- or demotive- 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, uh, 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- 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 that they knew they would work all night long (laughs) 'cause they probably wouldn't sleep in anticipation for this. So, that's a- that was another issue for, I- I'd say. Um, I'd say 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 that 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, uh, you know, a lot of stress. And so, at the end of the day, I think Brian is an, uh, you know, a generational leader for, uh, as a Millennial, um, 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, uh, 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, uh, to

4. 18:27 – 21:08

   Tactics to be effective when working with founders in founder mode

   1. CCChip Conley18:27

      leading people.

   2. LRLenny Rachitsky18:28

      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, uh, tactics to be effective with founders in founder mode?

   3. CCChip Conley18:53

      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, uh, a- as you present and Bryan's in the room. So Bryan, 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, um, both what's the intention of this iteration we're doing on the product, like what 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 Bryan or the founder, whomever it is, is beating you up on something, 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, um, yeah, so... So sit- try to set alignment on the front end.

   4. LRLenny Rachitsky20:06

      That's a, that's a important tip for anyone working with anyone even. So I love, I love just that that works es- especially well here. And then just going back to the credibility piece, uh, which 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."

   5. CCChip Conley20:27

      Yeah, and don't... And, and 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 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. Um,

5. 21:08 – 27:03

   The value of intergenerational collaboration

   1. CCChip Conley21:08

      but yeah.

   2. LRLenny Rachitsky21:09

      So, this whole story of you joining Airbnb in your 50s is a really good example of, of, uh, cro- 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.

   3. CCChip Conley21:28

      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 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, uh, 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, in crystallized 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. 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 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 Modie, um, Laura Hughes Modie, 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, 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, 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, uh, you know what, one of the things I said to Bryan early on, um, was, you know, "I, 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 at 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 Bryan...... 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 p- be paying o- occupancy taxes. So let's take some proactive steps toward 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, 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. 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- 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, John Q. Smith, uh, you know, an engineer who you... I think you probably remember him. Uh-

   4. LRLenny Rachitsky25:08

      Oh, yeah.

   5. CCChip Conley25:09

      ... uh, uh, at- at Airbnb. So this is a guy who looked younger than he was, and, uh, was... he was a little bit nervous about pe- like, telling people his age. But the thing w- 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 ev- every, you know, month. But he became a great manager, 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 may be better technically than he or she is, but they know how to elevate talent. Uh, 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 be the kinda person who wasn't solving all the problems, but I was trying to elevate. There's a woman named Lisa Dubost who is a- at- at Airbnb, and she one day ca- I... the HR depo- per- part- department was reporting to me at one point, and she was running HR, and 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 Lis- Lisa has a French accent and s- you know, fluent in French, and she sa- 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."

   6. LRLenny Rachitsky26:39

      (laughs)

   7. CCChip Conley26:39

      Like, a confidant's someone who has the secrets. And- and she said to me, "No, in my p- 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

6. 27:03 – 31:18

   Addressing ageism in tech

   1. CCChip Conley27:03

      to success."

   2. LRLenny Rachitsky27:04

      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- how real is ageism in tech? A- 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, and if they're someone in their 50s, I'll hire them, no problem." Doesn't feel like it actually works out that way often. Just how real of a problem is this? What do you see?

   3. CCChip Conley27:27

      Yeah. It, you know, it's clearly a problem. Um, I'd say it's maybe a little bit less of a problem m- than it was a dozen years ago, because I think a dozen years ago, it was almost a blind spot. Uh, 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, which is good because it means that there's a... there's a voice and, uh, a way to congregate with a bunch of people who are older. Uh, ultimately, we had these senior... we had these senior nomads come in and be, like, the voice of the customer for 10 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 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 f- you know, uh, set of skills that an older person doesn't have, 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 ballgame, and the question, I think, will be, if what AI cannot do is the human wisdom piece, artificial intelligence and- and human wisdom might be the balance beams here, is it possible that older managers who have a little more e- emotional intelligence, a little bi- more pattern recognition, a little bit more wisdom, um, h- uh, can be a value to a company? And so it's still... uh, the- the- the jury's still out. There was a New York Times article that just came out about the question of, is AI gonna wi- wipe out older people's jobs or younger people's jobs? And I think the answer is both (laughs) , um, 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, what, 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, uh, down to 40% or 50% time, and my stock, uh, my, you know, options were do- dropped to that level, my salary was 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. Um, Airbnb, one of the biggest challenges at Airbnb has always been, how do I get shit done around here? Um, and...Process knowledge allows you to understand, how do you, 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. So, long story short is, um, I just think that, uh, you know, 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."

   4. LRLenny Rachitsky30:49

      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.

   5. CCChip Conley31:03

      Yeah.

   6. LRLenny Rachitsky31:04

      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. When you look at people you've worked with and had at your academy, which we'll talk about, who

7. 31:18 – 35:01

   Advice for thriving as an older individual in tech

   1. LRLenny Rachitsky31:18

      continue to thrive and continue to have a really healthy career in tech, what do they do differently? What did they do? What, what do they have in common that other folks you think should work on and focus on?

   2. CCChip Conley31:28

      I think this key- this idea of being a mentor, and a mentor and an intern, I think 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 th- 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 l- resting on your laurels. You are, you have, uh, like physical, you know, energy in how you do your job. And when people are like that, they are sort of timeless. They are, uh, they're age fluid, as I say. Um, (laughs) we talk about gender fluidity. Well, there could be age fluidity. They, they don't, they're not defined by their age. But the other part of energy that, that's important is po- being positive. You know, that 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 10 or 20 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 I, and, um, so my energy, both the positive energy part and then also the fact that, yeah, I, I could work 60 and 70 hours a week, 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 times on stage. (laughs) 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." 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 th- younger than you, and you're gonna probably do pretty well.

   3. LRLenny Rachitsky33:44

      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.

8. 35:01 – 42:37

   Advice for hiring managers

   1. LRLenny Rachitsky35:02

      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 t- way to describe. So, uh, at every stage of life, curiosity is, uh, something 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 companies with ageism in tech, uh, 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?

   2. CCChip Conley35:40

      I think we're moving into, there's a, there's a book that David Epstein wrote called Range. And the whole premise of Range is that we're moving out of the era of the specialist and into the era of the generalist. 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 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...... uh, is, yeah, 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? 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? Um, one of the things I- I- I loved at Airbnb, the- there were 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. So, there's 97% 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 2013, 2014. And so, there are people in (laughs) who knew iPhone or Google Suites back then. I'd 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?" Um, or, "How do you give a great employee review?" You know, 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 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 were an, uh, 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 a huge value in a younger company when you have some older people who have not been vested with the responsibility of managing those younger people, because they maybe 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 unexpected value that I was able to offer to Airbnb and to Brian specifically, because there are a ton (laughs) of people in Airbnb who were not even in my departments who would come to me and say, "I'm having a problem."

   3. LRLenny Rachitsky38:47

      (laughs)

   4. CCChip Conley38:47

      "H- how do I solve this? Can we spend lunch together?" And, you know, I almost always said yes.

   5. LRLenny Rachitsky38:53

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

   6. CCChip Conley39:01

      Yeah, I mean, i- i- yes and it all comes back to curiosity. If I was just the older elder dispensing wisdom, people would've 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 was a, I- I- I- 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 per- partly because I lost track of my age.

   7. LRLenny Rachitsky39:38

      Uh, that's such a good, it's such good advice on the front end, uh, to be successful as a person kind of getting older in tech is curiosity, positive energy, the way you talk- talked about it, uh, passionate, passionate, uh, engagement. Is that the term?

   8. CCChip Conley39:52

      Mm-hmm. Yep.

   9. LRLenny Rachitsky39:53

      And then on the other side is, uh, hire a generalist. This actually comes up a lot in- in the AI conversations, just exactly as you said, the power of generalists. It 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... I'm so bad at just getting, thinking about the details. And AI solves all that for me." It's like, "Here, here's what I'm gonna do. I'll do this for, move my house to here or here." And it's like, "Here's what you need to do. Step one, two, three, four, five."

   10. CCChip Conley40:18

       It is remarkable. I mean, you know, uh, it, since the time I've known you, how fast it has become dominant in our lives. Uh, but yeah, I think, uh, one of the last thing I'd say is look, I'm privileged.

   11. LRLenny Rachitsky40:32

       Yeah.

   12. CCChip Conley40:32

       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, but I could have been plucked and brought in and partly as- as Brian's boy, people would've like rejected me because if I didn't show up the right way, it wouldn't have worked well. Uh, and there are lots of people who Brian brought into the company (laughs) who didn't work well. So I think, I think the key is how do you get the foot in the door? And at the end of the day, um, you know, there's second and third order of, you know s- uh, degrees of separation, um, in terms of networking is, are still essential, but the most important thing is to be able to articulate h- what you have accomplished in a new way that a recruiter says, "Wow." And so, I, I really tell people like, "I w- I would love to see a resume." First of all, the question that, uh, I think it wa- it was... Who was it? Someone asked it. I don't remember if it was Sheryl Stanberg or someone else asked her, who said 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, what I love to see is not so much what roles you've had, what bullet points do you have of your s- like things you've learned. Give me in a paragraph a h- a- 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? 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 inter- your interviews.... so.

   13. LRLenny Rachitsky42:34

       I love that we're, I love that we're getting into interview advice and resume advice.

9. 42:37 – 44:12

   Chip’s early career and founding Joie de Vivre

   1. LRLenny Rachitsky42:37

   2. CCChip Conley42:37

      Yes.

   3. LRLenny Rachitsky42:38

      Um, speaking of thorny problems, and also, uh, why Brian decided to reach out to you, I wanna go back to the beginning of your career.

   4. CCChip Conley42:45

      Yes.

   5. LRLenny Rachitsky42:45

      So, running a business-

   6. CCChip Conley42:47

      Randy, you're g- you're good at this, by the way. You're good at this.

   7. LRLenny Rachitsky42:49

      (laughs) I was thinking ahead. Okay, so you were in business school, you left business school. You just thought, you were like, "Maybe I should start a hotel," uh, 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. You ended up building the second-largest boutique hotel chain in the world, the Joie de Vivre, uh, beloved, uh, I, I, I loved every single experience I've had at Joie de Vivre. When you sold it, I was like, "That is so sad." Talk about just that, that story.

   8. CCChip Conley43:18

      Yeah.

   9. LRLenny Rachitsky43:18

      Uh, I know this could go on for hours, but what's the-

   10. CCChip Conley43:21

       Yeah, I'll be, I'll be brief.

   11. LRLenny Rachitsky43:22

       Yeah, perfect.

   12. CCChip Conley43:23

       26 years old, couple of 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, eh, because I'd 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, uh, and, uh, and turned it into the Phoenix, which became a famous rock and roll hotel that I have owned for 39 years now. Um, so long story short is, that was how I started Joie de Vivre, the company, and we grew to 52 hotels around California, became the second-largest, uh, as you said, in the, in the world, uh, in terms of the number of hotels, boutique hotels that

10. 44:12 – 47:51

    A life-changing near-death experience

    1. CCChip Conley44:12

       we operated. And I loved it till I hated it. In my late 40s, I hated it. (laughs) 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, uh, what I, I now call a midlife chrysalis, uh, a b- a midlife crisis, um, where I just wanted to change everything. And, um, I got through it. Uh, I had an NDE, I had a, 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, uh, you know, I decided to sell my company at the bottom of the Great Recession. So, that's, so that was really how I had created this space in my life to be able to join Airbnb.

    2. LRLenny Rachitsky44:58

       Well, let's back up a little bit. This near-death experience, uh, share more there, what happened there?

    3. CCChip Conley45:04

       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. Uh, I broke my ankle at a bachelor party, uh, playing baseball. And, um, I ended up with a cut on my leg, and, um, the cut on my leg w- had fertilizer in it and went septic. And so, I was on a very strong antibiotic, and I died. I went flatline from the all- allergic reaction to the antibiotic. And so, I saw, you know, I, it happened nine times over 90 minutes, and 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, they thought it was a s- I thought they thought it was a heart attack. They thought a bunch of stuff, stroke, et cetera. No, 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-

    4. LRLenny Rachitsky46:09

       You did?

    5. CCChip Conley46:10

       ... to go into it.

    6. LRLenny Rachitsky46:10

       What?

    7. CCChip Conley46:11

       I did. You wanna hear this? Yeah, no. I saw-

    8. LRLenny Rachitsky46:12

       Yeah. (laughs)

    9. CCChip Conley46:12

       ... this beautiful stuff.

    10. LRLenny Rachitsky46:13

        Let's do it.

    11. CCChip Conley46:14

        Um, the, the bes- 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 Vitali. Um, in that hotel, there were these slippers in every guest room. One slipper said, "Slow," the other slipper said, "Down." Um, and so I was wearing these slippers in my flatline thing, uh, s- uh, 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 s- 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 li- limit it to that, and just say, and then the birds would s- 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 r- right as I would get to the window, all of a sudden I'd come back to life.

    12. LRLenny Rachitsky47:20

        Holy shit. Uh, I love that this was, uh, like there was a message inside of this experience. I don't know how many people experience that. Clearly this led to a big life change. And it's interesting, a lot of the times you need something like that. Like, you've been doing this for how many years at that point, running Joie de Vivre?

    13. CCChip Conley47:38

        Uh, at that point I'd been running Joie de Vivre for 22 years. And-

    14. LRLenny Rachitsky47:40

        22 years.

    15. CCChip Conley47:41

        Yeah.

    16. LRLenny Rachitsky47:41

        And it's interesting that you need something like that a lot of times. Otherwise, it's just momentum just keeps carrying you forward.

    17. CCChip Conley47:46

        Yep. Within two years, I'd sold it, and you know, uh, I had ch- the chance to move on.

11. 47:51 – 52:20

    The importance of company culture

    1. CCChip Conley47:51

    2. LRLenny Rachitsky47:51

       So with building Joie de Vivre, 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. 'Cause a lot of people talk about culture, warm, fuzzy stuff, but you think about it very tangibly.

    3. CCChip Conley48:15

       Culture is what happens around here when the boss is not around. (laughs) Um, and, and the more distributed a company, the more culture's important because the boss is around in a traditional bricks-and-mortar workplace where everybody shows up at 8:00 and leaves at 6:00, and we all see each other.But, uh, at- in my company, Joie de Vivre, 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- 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, 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 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 out at Airbnb all- over and over again. Uh, in- in fact, Airbnb saw it, I think, when- with Amazon people. Um, Apple people have resonated pretty well at- at- at, uh, Airbnb. Amazon people less so. And those are two different cultures, Amazon and Air- and Apple. And the- therefore, understanding a culture before you even actually take the job 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, there's language about culture fit. I like to say culture add. Because culture fit to me means- uh, could actually be quite negative toward somebody who is 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 person in a wheelchair. So, you have to fit in. But a culture add suggests that actually having some diversity on the team is helpful because it actually adds to the culture. But it still ha- 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 pul- you know, employee pulse reports and things like that.

    4. LRLenny Rachitsky51:24

       You talk about having to understand a culture is such a key part of having success at a company. Do you have any advice for just how to understand that culture for someone interviewing? I don't know. Like, you know, you came in, you worked part time, it's easier to experience it all. Any tips there for, like, "Okay, this is for me, that's not for me"?

    5. CCChip Conley51:39

       When you're interviewing, you're al- 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, 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, in terms of something that's just endemic or just, like, baked in across the organization? And is it ever gonna get fixed? And how could I come in and maybe help that?"

12. 52:20 – 57:09

    The Peak Model

    1. CCChip Conley52:20

       Uh, which, frankly, at a very junior level, you're not gonna be able to help it, uh, e- except for in very minor ways. If you're a senior person, you might be able to help it. Um, so those are- those 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? Um, and if I'm not, is that because there's not alignment? Is that because different departments 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. 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, and 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 may be m- you may lose people.

    2. LRLenny Rachitsky53:23

       When I reflect back on one of the- on- on the impact you had at Airbnb, one of the funny, uh, things I think about is, uh, triangles showing up a lot on decks.

    3. CCChip Conley53:34

       (laughs)

    4. LRLenny Rachitsky53:34

       Uh, and specifically, uh, rooted in Maslow's hierarchy, just like everything's this Maslow hierarchy metaphor.

    5. CCChip Conley53:41

       True.

    6. LRLenny Rachitsky53:41

       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 be successful at a company that's kind of rooted in your Peak book, uh, 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.

    7. CCChip Conley54:00

       So, you know, Maslow's hierarchy basically five levels. Later in life, he had a s- seven and an eight level model, but, you know, uh, at the base is f- you know, physical, uh, you know, the kind of physical water, food, air, 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- you know, the Peak, uh, my book. Um, the employ model 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 90% of the pyramid.So just because it's at the base doesn't mean it's not dominant part of the pyramid. But the differentiation often is in recognition and meaning. In nonprofits, usually the, the money piece of it's rather thin, and the recognitions there and meaning's huge. So, uh, so understanding how do you create an organization, and I, and I gave a TED Talk in 2010 about this topic as well, um, how do you create a, 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, i- 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 Mildenhall was joining is, we really tried to s- 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, we came up with the idea that we were in the belong anywhere business. Eh, Airbnb was not in home sharing. We were in belonging anywhere. So once you have that, 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 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, you know, this model, the idea of hierarchies is, I think, very helpful. Um, and, uh, yeah, my book Peak is, has been around for 18 years, but I still am asked to give 20 or 30 speeches a year on it.

    8. LRLenny Rachitsky56:30

       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, 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 $100 million offer? And seems to be happening in a lot of cases, which shows you the power of meaning.

    9. CCChip Conley56:55

       Yeah. I mean, y- 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.

13. 57:09 – 1:00:30

    The Modern Elder Academy (MEA)

    1. CCChip Conley57:09

    2. LRLenny Rachitsky57:10

       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 in the c- called the Modern Elder Academy. Talk about what is the Modern Elder Academy.

    3. CCChip Conley57:28

       Yeah. What is going on with that Modern Elder Academy?

    4. LRLenny Rachitsky57:30

       (laughs)

    5. CCChip Conley57:30

       The Modern Elder Academy, so there was a couple 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. 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 it MEA, because elder is 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, y- you know, your 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. Let's say between, I, I define midlife as 35 to 75, guys, so like, this is th- 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. 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 D- 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, 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, 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 n- the natural next thing for me to do. I, 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 Esalen Institute in Big Sur for 10 years. I love wellness. I've owned the Kabuki Springs & Spa for 28 years, 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, uh, Harvard, Yale, Stanford, and UC Berkeley professors helping us, h- a great, greater curriculum around midlife. Um, and so that's how MEA came about.

    6. LRLenny Rachitsky1:00:14

       Uh, to your point, I forget who said it, but 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.

    7. CCChip Conley1:00:22

       Yeah.

    8. LRLenny Rachitsky1:00:23

       Uh, also, I'm learning more things about you. I didn't know you were involved with the Kabuki spa. I think Esalen I knew, just keep, keep getting more interesting.

14. 1:00:30 – 1:06:43

    The upside of aging

    1. LRLenny Rachitsky1:00:30

    2. CCChip Conley1:00:30

       (laughs) Thank you.

    3. LRLenny Rachitsky1:00:32

       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?

    4. CCChip Conley1:00:43

       Yeah. I- 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 15 to 20 years.If you sort of take, buy into the ageism of American society, or Hallmark cards when you get a, a c- a card at age 40, 50 or beyond. There's a belief that life gets worse as you get older. And, um, and if you can survive your mid-life crisis all you'd have to look forward to is disease, decrepitude and death. 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 Mid-Life. 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, it summarizes the MEA curriculum. 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 t- 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, 10 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. But when I moved to Baja part-time in Mexico at age 56, 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, "10 years from now what will I regret if I don't learn it or do it now?" And I said, "Well, 10 years from now I might still be living in Baja." Like, "I should learn the s- 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 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 You Curve of Happiness. And it's been around for 20 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 20 or a 22-year-old, really unhappy. 24-year-old, really unhappy. But historically w- the way it was is you were happy from 18 to 23 or 24. And then around 23 to 24 you start to see a long slow decline in life satisfaction that actually, uh, bottoms out between 45 and 50. I'm sorry to tell you that, Lenny, since you're 44. Um, but your mileage may vary. Uh-

    5. LRLenny Rachitsky1:03:17

       (laughs) So you're saying I'm the least happy I'll ever be. Like, that's only upside, that's great.

    6. CCChip Conley1:03:21

       Yeah. Well, here's the part that's weird, is that when, before this re- research was done, and it's global research across all demographics. What they found was, uh, starting around age 50 or 52, you get happier. So that you're happier in your 50s than your 40s. 60s, 50s. 70s happier than 60s. And women in their 80s happier than 70s. So, wow. And it's partly because we are in, around 45 to 50 doing this thing called the, um, the mid-life unraveling. What Brene Brown calls the mid-life unraveling. You're unraveling your expectations, your, uh, what you define as success, uh, your definition of y- what a beautiful body looks like. And you get some, uh, l- you're liberated into freedom in your 50s and beyond. And, uh, I, I can say that, yeah, I'm happier today at 64 than I was at 47 when I was going through my flat line experience and not wanting to run my company anymore.

    7. LRLenny Rachitsky1:04:19

       You used this term earlier, the mid-life chrysalis? Was that what it was?

    8. CCChip Conley1:04:22

       Or chrysalis. Chrysalis, yeah.

    9. LRLenny Rachitsky1:04:23

       Chrysalis. What is that? Is that kind of along the same lines?

    10. CCChip Conley1:04:27

        So if you think about the caterpillar to butterfly journey, mid-life is the chrysalis. It's that cocoon-

    11. LRLenny Rachitsky1:04:32

        Mm-hmm. Mm-hmm.

    12. CCChip Conley1:04:33

        ... 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, you, there's a metamorphosis that happens. And so, uh, I, I like to use the language, in, in fact I have a podcast called The Mid-Life Chrysalis, um, because I wanna help, you know, change the dialogue around mid-life so that the number one word attached to mid-life 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.

    13. LRLenny Rachitsky1:05:09

        That is actually very empowering. I am sort of going through that. Not necessarily in this intense way yet. But that might be coming. (laughs) 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."

    14. CCChip Conley1:05:23

        Emotional intelligence grows with age. Um, 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. Uh, what else gets better with age? You learn how to edit. You ca- you, you have no more Fs 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. Uh, you're, um, I mean, the list is long. And, and so there are a lot of things that ... Yeah, actually another one that I lo- love is c- you're not compartmentalized. When you're younger you're compartmentalized. As you go, 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 are, like, they are just who they are.

    15. LRLenny Rachitsky1:06:25

        There's a quote I found from you along these lines. "The societal narrative on aging is just don't do it."

    16. CCChip Conley1:06:31

        (laughs) Yeah. There, the, 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 our aging and growing.

15. 1:06:43 – 1:08:05

    Who MEA is for

    1. CCChip Conley1:06:43

    2. LRLenny Rachitsky1:06:43

       Hm. Coming back to MEA, just for folks that are, like, interested, curious about this. Who's this for would you say? Who should seriously look into this program?

    3. CCChip Conley1:06:52

       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, 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. 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. An- and the two campuses are just gorgeous. Uh, they've... It's been called The Four Seasons meets Blue Zones meets the Esalen Institute, which I like. Um, and, uh, we do have... 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.

    4. LRLenny Rachitsky1:07:54

       Those three. Yeah, that's the tagline. That's your tagline, right there (laughs) . Esalen meets Blue Zones meets... Wha- what was the first one?

    5. CCChip Conley1:08:00

       The Four Seasons.

    6. LRLenny Rachitsky1:08:01

       The Four Seasons (laughs) .

    7. CCChip Conley1:08:02

       Yeah.

    8. LRLenny Rachitsky1:08:03

       Nailed it.

16. 1:08:05 – 1:10:20

    AI in daily life

    1. LRLenny Rachitsky1:08:05

       Okay. I'm gonna zoom out and take us to a recurring segment on this podcast. I wanna see if this goes anywhere. Uh, AI Corner. And with AI Corner, I 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've found useful.

    2. CCChip Conley1:08:23

       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 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 d- write really well in the morning. If it's any other time of the day, I do not like writing, creatively. Um, so if I have a deadline for tomorrow, and it's five o'clock in the af- afternoon, it's like, "Okay, ChatGPT, I'm on my way to you." And then I tend to use ChatGPT the most, because I don't know. I mean, I like Claude as well, but, um, yeah.

    3. LRLenny Rachitsky1:09:03

       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 draft blog post"?

    4. CCChip Conley1:09:12

       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 sort of s- weird sense of humor, uh, so it's able to ape me pretty well. So, I'll just say, "I need a 250-word post on..." Um, like today, the... You know, today's post was a post that ChatGPT helped me with it. I said, "I believe that there's a, a, a reframe 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." Um, what if, in fact, my job is just to be this vehicle for my soul to c- go to the next lifetime, and my... So, my job is to be this 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... N- not all my blog posts are so new age and, and, uh, like that. I w- I w- I write a lot on leadership. But that was one that, you know, within, you know, 30 seconds, I had a 250-word, you know, blog post that I then adapted, and there you go.

    5. LRLenny Rachitsky1:10:19

       Amazing.

17. 1:10:20 – 1:19:00

    Lightning round and final thoughts

    1. LRLenny Rachitsky1:10:21

       Chip, we've covered a lot of ground. We've gone through your entire life (laughs) . May be 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?

    2. CCChip Conley1:10:31

       Yes. Let's do it.

    3. LRLenny Rachitsky1:10:32

       First question, what are two or three books that you find yourself recommending most to other people?

    4. CCChip Conley1:10:37

       My favorite book of all time, Man's Search for Meaning, Viktor Frankl, uh, in a concentration camp in World, uh, War II. When someone's going through a hard time in their life, I say read that book. You'll realize it's not so bad-

    5. LRLenny Rachitsky1:10:49

       (laughs)

    6. CCChip Conley1:10:49

       ... what you're going through.

    7. LRLenny Rachitsky1:10:50

       Yeah.

    8. CCChip Conley1:10:50

       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 o- o- of me. Um, so that's one. Um, I... You know, I love, uh, any book by Liz Gilbert, um, 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. Um, uh, 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? Um, 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 to come through you.

    9. LRLenny Rachitsky1:11:44

       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 that are really interesting to me. This is... You wrote about these in a book.

    10. CCChip Conley1:11:53

        Yeah.

    11. LRLenny Rachitsky1:11:54

        You have a bunch of these equations about living a happier life. So, the one you shared is despair equals suffering minus meaning.

    12. CCChip Conley1:12:00

        Yes.

    13. LRLenny Rachitsky1:12:01

        And so, the implication there is if you want less despair, increase the meaning-

    14. CCChip Conley1:12:05

        That's right. So, suffering-

    15. LRLenny Rachitsky1:12:06

        ... or reduce the suffering.

    16. CCChip Conley1:12:06

        Suffering... The sort of Buddhist philosophy num- The first noble truth of Buddhism is that suffering's ever-present. And so, if suffering's a constant and you have two variables, uh, using some algebra, I guess, um-

    17. LRLenny Rachitsky1:12:19

        (laughs)

    18. CCChip Conley1:12:19

        ... you know that, uh, if- if you have more meaning, you have less suffering. And so, that's that one.

    19. LRLenny Rachitsky1:12:25

        The other one that I love is anxiety equals uncertainty times-

    20. CCChip Conley1:12:29

        Ooh.

    21. LRLenny Rachitsky1:12:29

        ... powerlessness. Maybe talk about that one briefly.

    22. CCChip Conley1:12:32

        98% 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, 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? 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, uh, a- an equation-... it actually makes it more tangible, and you often are less anxious as a result.

    23. LRLenny Rachitsky1:13:11

        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. That's what-

    24. CCChip Conley1:13:18

        Yes.

    25. LRLenny Rachitsky1:13:19

        ... I'm hearing. Okay, excellent. Very, very good nugget of advice. Okay, let's keep going with the lightning round, come back from our tangent. Do you have a favorite recent movie or TV show you really enjoyed?

    26. CCChip Conley1:13:29

        I mean, Ted Lasso is, I'm, uh, 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, i- at our Santa Fe campus. Um, and I would say that the film that I'm most excited about that is coming out, um, 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, uh, in a gen- degenerative, uh, 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.

    27. LRLenny Rachitsky1:14:08

        Amazing. Very deep cut. Do you have a favorite product that y- you recently discovered that you really love?

    28. CCChip Conley1:14:17

        Yes. Hair growing material. (laughs) No. Um, you know, v- uh, Vuori shorts, I, I, you know-

    29. LRLenny Rachitsky1:14:24

        Hmm.

    30. CCChip Conley1:14:24

        ... I sound like Scott Galloway because he ta- he advertises this, but Vuori shorts are like... I just love them. You know, they're-

Episode duration: 1:19:36