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

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

I was mentoring Brian, but he was also my boss. I was 52. The average age was 26. I had to be both wise and curious and often the dumbest person in the room.

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

Brian assumed everybody else was going to work at the same pace and duration. His point of view was like, hey, we're having a meeting in the office tonight at 10 o'. Clock. You know, be there.

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

Isn't the product the homes and the apartments? Jot 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.

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

When you have older brains connecting the dots, younger team members being really fast and focused, it's brilliant. And people won't notice your wrinkles as much as they'll notice your energy.

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

So if you think about the caterpillar to butterfly journey, midlife is the chrysalis. Midlife is not crisis. I'm happier today at 64 than I was at 47 when I was going through my flatline experience.

Well, let's back up a little bit. This near death experience today. My guest is Chip Connolly. Chip is one of the most extraordinary and interesting people that you will ever meet. He was a founding member of the board of Birmingham. He was on the board of the Esalent 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 U.S. 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 subscriber of my newsletter, you get a year free of a bunch of incredible products including replit, lovable, bolt, N8N, linear, superhuman, descript, Whisper Flow, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, Chepier, Dmobin, and more. Check it out at lenny'snewsletter.com and click bundle. With that I bring you Chip Connolly this episode is brought to you by Great Question. The all in one UX research platform loved by teams at Brexit, 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. 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.comlenny 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 SoC2, 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.comLenny that's V A N T A.comLenny. Chip, thank you so much for being here and welcome to the podcast.

Oh my God, Lenny. I sort of feel Like, I'm your father who's so proud of his son. My son has done so well, and I, I like to talk about, tell my friends about you.

Wow. I am honored. I'm happy that I'm making you proud, Chip. And I feel, 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 to 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, and the three parts are your early career, building joie de vie, 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'm going 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 something, 30 somethings, reporting to Brian Cheske, who is, I don't know, in his 30s. What was that like?

So, yeah, I, I wasn't planning on doing this. I, I got a call 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? This was 13 years ago. This was, I think it was the end of 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 the innovation and hospitality and, 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, I want you to come in for and work 15 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, 15 hours a week is great. And then within three weeks, it was 15 hours a day. And Brian, and I was saying to Brian, you know, you're actually not paying me anything. He gave me 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. This is you. You. It seems like the company needs me a little more than you said. And. And he said, yeah, I gotcha. I just wanted you to get in here and see, like, what you could do. And long story short is I ended up going full time. And it was hard at first, 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 Brian on leadership, but he was also my boss. I was the head of global hospitality and strategy. So which meant. Meant initially I was in charge of all the hosts in the world. Over time, that was 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 is, was just that initially when people were talking about product, and Jobot 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 Jobot said, no, product. 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. It required me to have a certain amount of humility as well as to be reporting to a guy 21 years younger than me.

Brian, 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 got to make the product better. We got to 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 and helping us communicate differently to hosts who also don't understand.

Well, there's an interesting thing also, Lenny, and you know this. The difference in age between our hosts and our guests was probably about 10 years maybe. And over time, it actually got higher because we started actually reaching out more aggressively to, you know boomers and Gen Xers to be hosts. And so you had, I remember at 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, 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 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 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 guys and women in their twenties who are the engineers and designers and product managers. And I always liked working with you. I want just compliment Lenny for a minute 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 going to mention their names. And there are 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. You know, that's, that's the try to. The kind of environment I tried to embody there.

Absolutely. There's a couple of threads there I want to follow. One is just working for Brian. A lot of people talk about founder mode and the power founder mode. It's so great. That's how we do it.

And guess who, like, you know, popular with that recently? That was Brian.

Exactly. So it's great to be in fatter mode. It's not, 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, he was in his 30s. You're in your 50s. 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. It's like, I was wonderful. I learned so much. Just like, what was that experience? Like, what did you learn from working for someone like Brian?

Well, let's start with the fact that I would never have gone to work for Airbnb if I didn't believe in Brian. Because, quite frankly, when Brian approached me and we started talking about, I was like, I wasn't sure I liked the 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 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 apartment getting trashed by a guest, and so Brian decided he was going to go to find, you know, George Tenet, the former head of the CIA. And so, like, Brian would go to experts 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 say, I want to learn more about this. 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 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 is like, hey, we're having a meeting in the office tonight at 10 o'. Clock. You know, be there. It's 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 ended up going full time, and it was Hard at first, 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 Brian on leadership, but he was also my boss. I was the head of global hospitality and strategy. So which meant initially I was in charge of all the hosts in the world. Over time that, like, you know, that meant a lot more things too. I was involved in mo many parts of the business, definitely not the technical parts. But I think the hardest thing for me that was different than a lot of the other product managers. There's other product managers. I'm not going to mention their names. And 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. Is was just that initially when people were talking about product and Joe Bot said, you know, I'm the chief product officer and I'm like, well, isn't the product. Isn't the product the homes and the apartments? And Jobot said, no product in the tech industry is something different. And so 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. You know, that's, that's the try to. The kind of environment I tried to. To embody there.

Absolutely. There's a couple of threads there I want to follow. One is just working for Brian. A lot of people talk about founder mode and the power founder mode. It's so great. That's how we do it.

And guess who, like, you know, popular with that recently? That was Brian.

Exactly. So it's great to be in fetter mode. It's nuts.

I had to be both wise and curious and often the dumbest person in the room. And that was. It required me to have a certain amount of humility as well as to be reporting to a guy 21 years younger than me.

Brian, that actually the point you're making there about what is the product 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, he was in his 30s, you're in your 50s. 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. It's like, I was wonderful. I learned so much. Just like, what was that experience like? What did you learn from working for someone like Brian?

Well, let's start with the fact that 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 business 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 is like, hey, we're having a meeting model all that well as a hotelier. So I had to believe in something beyond the business model because I wasn't sure that this amount, the business model would work. Although soon after joining, I saw the numbers, I was like, wow.

This day I asked Laura Hughes, formerly Laura Modi, what to talk to you about, who we got to work together. She's the CEO of Boss is working pretty well.

But I believed in Brian because the thing that Brian showed up with initial thing in the, in the office tonight at 10 o', clock, you know, be there. No, I don't, I don't think so. But so, so I think the, the, the fact that Brian assumed everybody else was, was as one dimensional in their focus as him was at times a problem, especially for a guy like me who was, I was at a stage in my career where, like, I have a lot of interests. Um, so that was one number two is, was just a curiosity and an appetite for learning. And, you know, I remember back in 2011 when the, you know, the big debacle happened with the apartment getting trashed by a guest. And so Brian decided he was going to go to find. Brian admires and admired back then, you know, George Tenet, the former head of the CIA. And so like 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. Brian would go to experts and say to the expert, I don't know what the hell I'm doing than anybody else. And so there was this, you know, one of the challenges for a CEO sometimes and I, this was my experience in my 24 years of running Joie de Viv, my boutique hotel company is, it feels sort of see some copy.

Now you work closely with her at Airbnb and she said this is the thing that stuck with her most about working with you is coming in and everyone's talking about we got to make the product better, we got to 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 and helping us communicate differently to hosts who also don't understand.

Well, there's an interesting thing also, Lenny, and you know this. The difference in age between our hosts and our guests was probably about 10 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 at one point, and again, let's get into product talk here. I remember at one point there was a conversation that was going on about taking Airbnb. So it was mobile only. I mean, 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 I was like, oh, wouldn't it be interesting if everything was mobile and it's something and then point out the things that are wrong makes you feel good. And, 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 want to learn more about this. So it's sort of a growth mindset. When 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 mo. What was hard with Brian is I'd say three things. Number one, if you don't have emotional intelligence, you can, 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? And so there were times where I was a voice for older one is Brian assumed everybody else was going to work at the same time pace and duration, you know, and he still has this issue. I mean 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 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 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. 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 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 o'.

Clock.

You know, be there. Really? No, I don't, I don't. So they knew they would work all night long because they probably wouldn't sleep in anticipation for this. So that. 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 that was another issue. For I'd say I did the other thing that you know, that. 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 of 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 that adding a zero to something in terms of expectations or Steve Jobs so much that there was a sense that as users in this Case hosts. That was helpful to, you know, a guy who came from the product world, from the Rhode island school of design. He knew better. Thinking you're going to 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 than anybody else. And so there was this, you know, one of the challenges for a CEO sometimes. So there was a sense that Brian had. That he had to maybe create ridiculous goals. And I. This is my experience in my 24 years of running Joie de vivre, my boutique hotel company is it feels guys and women in their twenties who are the engineers and designers and product managers. And I always liked working with you. I want to just compliment Lenny for a minute.

How sweet is that?

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 going to 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 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 people off or, or demotiv. 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. 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, 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. You know, that's, that's the. Try to. The kind of environment I tried to. To embody there.

Absolutely. There's a couple of threads there I want to follow. One is just working for Brian.

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 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.

A lot of people talk about founder mode and the power of founder mode. It's so great. That's how we do.

And guess, guess who. So they knew they would work all night long because they probably wouldn't sleep in anticipation for this. So that was another issue for. I'd say, I think the other thing that, you know, 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're going to set a deadline that is unreasonable. Like, you know.

Exactly.

That was Brian.

Exactly. So it's great to be in fatter mode. It's not.

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 a generational leader 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.

Not as great to be working for someone in founder mode, often a very challenging place to be. 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, he was in his 30s. You're in your 50s. 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. It's like, I was wonderful. I learned so much. Just like, what was that experience like? What did you learn from working for someone like Brian?

Well, let's start with the fact that 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 apartment getting trashed by a guest, and. And so Brian decided he was going to go to find, you know, George Tenet, the former head of the CIA. And so, like, Brian would go to experts 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. 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.

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 got to do what I tell you. It's founder mode we're getting. 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 in founder mode?

So 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 both. What's the intention of this iteration that we're doing on the product? Like what defines success and what do I want to 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, 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.

That's a, that's an important tip for anyone working with anyone. Even so I love, I love just that that works especially well here. 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.

Yeah. And don't. I think the other thing is PowerPoint or whatever, whatever tool you're using. I mean, like, just be careful about being over humility to say, I want to learn more about this. 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 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 is like, hey, we're having a meeting in the office tonight at 10 o'. Clock. You know, be there. It's 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. Was as one dimensional in their focus as him was the reliant upon it. It just. It's. Especially when you have a combustible founder who may take you off path at times of problem. Especially for a guy like me who was. I was in 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 such that your deck in its current order makes no sense at all. Steve Jobs so much that there was a sense that as a guy who came from the product world, so that I always wanted to really limit the deck as much as possible because I didn't know 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 sometime where the meeting was going to 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, this was my experience in my 24 years of running Joie de Vivre, my boutique hotel company is.

It feels so this whole story of you joining Airbnb in your 50s is a really good example 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 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 into.

Other elements of your career.

I wrote a book called Wisdom at the Making of a Modern Elder after my Airbnb experience and I did a lot of research. I was like, wow, so why off or demotivate people? And in Brian's case, I didn't have to deal with that. Do we have less intergenerational collaboration in the workplace, especially in Silicon Valley, than 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 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 real too much because he didn't understand. When I was starting, it was really, I was in charge of the hosts around the world, really fast and focused and being able to think linearly how to get things done. Brain shrinks a little bit and you have crystallized intelligence and in crystallized intelligence. 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. 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 the night before, not just because they were actually working all night long to get prepared, but also they knew they would work all night long because they probably wouldn't sleep in anticipation for this. So that 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 an as noticeable quite frankly in some other diversities. So that was another issue for I. I'd say, I think the other thing that you know, that. And in each of these cases I think Brian's getting better. So just like Steve Jobs got better over time when he. So I found that over and over was really helpful. Part of my job sometimes was to find the blind spot, you know, again, if you are very focused, you know, one of the things I said 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 to Brian early on was, you know, I've seen the business plan. Now I know the goals of how big we want to be in three years. This was very early in my tenure. I said, but what we really have done, everything we're trying to do, is to, like, have no regulations and pay no occupancy tax. Now, hotels pay a bed tax, occupancy tax. 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 who know this, this is thinking you're going to set a deadline that is unreasonable, is necessary, because if you don't do that, there's an almost 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 going to be three years from now, I promise you, we're going to be regulated. I promise you, we're going to be paying occupancy taxes. So let's take some proactive steps toward building a strategy for how we're going to be regulated. And 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 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, 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 meeting some. There was a guy named John Q. Smith, you know, an engineer who you. I think you probably remember him at Airbnb. So this is a guy who looked younger than he was and was 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. 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, was a little bit nervous about, like, telling people his age. But the thing that was great about John is, over time, times when I saw how he was operating because he was not necessarily going to be the best coder at Airbnb. There was a whole new guy 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 going to be the best coder at Airbnb. There was a whole new collection of coders coming in every month, but he became a great manager who. 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, else 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.

For people in this position. A lot of people work for founders, especially now that founder and the beautiful.

Thing about moving from the, 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. I call this invisible productivity. It's productivity in which you make everybody else around you better 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, 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 is it a thing every founder is just like, I'm the founder, you got to do what I tell you. It's founder mode. We're getting. 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.

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 into me and she just said, chip, you are my confidant. 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 into me and she just said, chip, you are my confidant. And Lisa has a French accent and, you know, fluent in French. And she said, so she said confidant in just the right way. And. 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, someone has the secrets. And. And she said to me, no, in my.

In my part, sticks to be effective with founders in founder mode.

So if I, knowing what I know now, I would say, friends, 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.

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 that's because a lot of people that are hiring are probably thinking, no, no, I'm not biased. I'm going to hire the best person. If there's 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 the problem is this? What do you see?

Yeah, 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, it 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 thousand 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 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 any. 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, what defines success and what do I want to 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, 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 in a world in which that smartest new people, especially when it comes to technical skills and engineering, are coming in with a whole new, you know, set of skills that an older person doesn't have. The. The older person is both expensive and may be perceived as slow. So in the era of AI, it's a whole new ball game. 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, that's.

An important tip for anyone working with anyone, even so, I love just that that works, especially intelligence.

A little more pattern recognition, a little bit more wisdom can be a value to a company. And so it's still the. The jury's still out. There was a New York Times article that just came out about the question of is AI going to 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 that 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 well here.

And then just going back to the credibility piece, 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.

Yeah. And don't. I think the other thing is 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 going to go. And I wanted. The deck's helpful at the start, at the very start. Like, I think it went down to 40% or 50% time. And my stock, my, you know, options were dropped to that level. My salaries dropped to that level because I didn't want to 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 art, to just sort of set principles, set goals.

But, yeah, so this whole story of you joining Airbnb in your 50s is a really good example 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.

I wrote a book called Wisdom at Work. The Making of a Modern Elder After Means. That's really important. Airbnb. One of the biggest challenges that Airbnb has always been 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. So, long story short is I just think that, 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 going to get their money's worth in that.

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.

My Airbnb experience, and I did a lot of research, I was like, wow.

So why 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?

I think this. This idea of being a mentor and a mentor and an intern. There's just the voracious appetite for curiosity. When I talk to someone 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 are. You have like, physical, you know, energy in how you do your job. And when people are like that, they are sort of timeless. They are. They're age fluid. As 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 a 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. We 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 energies 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 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, 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 unity 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. You know, one of the things I said to Brian early on was, you know, I've seen the business plan now. I know 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 60 and 70 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 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 were, 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 younger than you, and you're going to probably do pretty well.

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, the.

Goals of how big we want to be in three years. This was very early in my tenure. I said, but what we really have done, everything we're trying to do, is to, like, have no regulations and pay no occupancy tax. Now hotels pay a bed tax, occupancy tax. 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.

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Have our guests pay taxes. Long story short is I said to Brian, if we're as big as we're going to be three years from now, I promise you we're going to be regulated. I promise you we're going to be paying occupancy taxes. So let's take some proactive steps toward building a strategy for how we're going to 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.

We have the team plan for startups that's C O D a IO Lenny to get started for free and get six months of the team plan. Coda IO Lenny ever since I was.

There and there's a few other markets in the. In the world where it was like that.

So 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 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.

Age of life. Curiosity is something to cultivate. I want to go to the flip side of companies looking to hire. Feels like there's this untapped supply of awesome people that companies with ageism and tech aren't finding and hiring. So, 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.

There was a guy named John Q. Smith, you know, an engineer who you, I think you probably remember him, they hire.

That might help them find these people.

I think we're moving into. There's a. There's a book that David Epstein wrote called Range. And the whole premise of Range is that we are moving out of the era of the specialist 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 at. At Airbnb? So this is a guy who looked younger than he was and was. He was a little bit nervous about, like, telling people his age. But the thing that was great about John is, over time, he was not necessarily going to 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. Because I actually think that's going to 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 are 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 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. 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, 2013, 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? 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 are. 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 that's a huge value in a younger company. When you have some older people who have not been invested with the responsibility of managing those younger people, because 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.

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.

Yeah. I mean. Yes. And it all comes back to the 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. Ooh, 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.

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

It is remarkable. I mean, you know, since the time I've known you, how fast it has become dominant in our lives. But, yeah, I think one of the last thing 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. 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, and she was 25 and had no background in HR at all. And one day she came into me and she just said, chip, you are my confidant, and I'm not in that position. The thing I would say is, you're right. So I. But Lisa has a French accent and, you know, fluent in French. And she said. So she said confidant in just the right way. And. 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, someone who has the secrets. And. And she said to me, no, in my. In my part of France, a confidant is somebody who gives you confidence. And it was like, oh, well, maybe that's what a mentor can be. Is a confidant, someone who gives you confidence and helps by asking questions, helps you as the younger mentee, find your roadmap to success.

So you're sharing a lot of really good examples of the value of older folks being within tech companies. So let me just ask you this. How. How real is ageism in tech and it. And that's because a lot of people that are hiring are probably thinking, no.

No, no, I could have been plucked and brought in, and partly as. As Brian's boy, people would have, like, rejected me because I'm not biased.

I'm going to hire the best person. If there's someone in their 50s, I'll hire them, no problem. Doesn't feel like it actually works out that way.

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.

I think I'm not biased. I'm going to hire the best person. If there's someone in their 50s, I'll hire them, no problem. Doesn't feel like it actually works out that way.

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 problem than it was a dozen years ago. Because I think a dozen years ago is almost a blind spot. Key is, how do you get the foot in the door? And at the end of the day, group called wisdom at Airbnb, it was the second and third order of degrees of separation in terms of networking are still essential, but the most 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 important thing is to be able to articulate what you have placed in 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 10 weeks that Airbnb accomplished in a new way that a recruiter says, wow. And so I really tell people 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 Cheryl Steve. 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 Amberg or someone else asked her who said, like, what's the biggest problem you're dealing with here and how can I help you set of skills that an older person doesn't have? The older person is both expensive and maybe perceived as slow. 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 your like things you've learned. Give me in a paragraph. So in the era of AI, it's a whole new ball game. 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 emotional, a thorny problem, youth intelligence, a little more pattern recognition, a little bit more wisdom can be a value to a company. And so it's still the faced 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. There's a New York Times article that Just came out about the question of is AI going to wipe out? And the older you are, the more you can actually have a resume like that. Older people's jobs or younger people's jobs? And I think the answer is both. And then you can use that as the conversation piece when you're doing interview interviews. So. But the question is, how much? How bad is it for both of them? And I think that 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.

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

Yes.

Speaking of throwing problems and also why Brian decided to reach out to you.

Like, I think it went to down to 40% or 50% time and my stock.

I want to go back to the beginning of your career.

Yes. So you're good at this, by the way. You're good at this.

I was thinking ahead, okay, so you're in business school. You left business school. You just said you're like, maybe I should start a hotel. 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 joie de vi. Beloved.

I, you know, options were dropped to that level. My salaries dropped to that level because I didn't want to 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, how do I get shit done around here? 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 I just think that, you know, older people might look at this.

I loved every single experience I've had as a. When you sold it, I was like, that is so sad. Talk about just that, that story, their.

Workload, and say, I'm willing to take a 20% or a 40% pay cut to go to.

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

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 want to do something more creative, 80% or 60% time. And the company is going to get their money's worth in that.

That's a really interesting point that if you're older and you're maybe less connected to the most cutting edge.

Bill Graham famous concert promoter said to me, you know, because I got into know him, what San Francisco really needs.

Is a rock and ways of building and, 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 hotel. So I decided to start looking to. To find a broke.

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 broken down motel hotel. That I could turn into a rock and roll hotel. And I found something in the Tenderloin and. And turn it into the Phoenix, which.

Became a famous rock academy which we'll talk about. Who continue to thrive and continue to have a really healthy career in tech. What do they do differently? What do they do? What, what do they have in common that other folks you think should work on and focus on?

Well, hotel that I have owned for 39 years now. So long story short is that I think this, 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 as they'll notice your energy. And that was how I started joie de vivre in the company. And we grew to 52 hotels around California became the second largest, as you said, 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 40s. I hated it. Energy has two parts to it. Energy is. They notice that you are not just sort of resting on your laurels. You are. You have like physical, you know, energy in how you do your job. And when people are like that, they are sort of timeless. They are, they're age fluid as I say we talk about gender fluidity. Well, this could be age fluidity. They, they don't, they're not defined by their age. But the other part of energies 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 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 so my energy, both the positive energy part and then also the fact that, yeah, 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. 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 were, but I wasn't aware of them. So I just think show up with that passionate engagement, that curiosity, that energy, that you don't want to do it anymore. I was, you know, the Great Recession came along and it was just kicking my ass. And I really went through a bit of a, what I 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. I 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 gift and a bonus. And 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.

Well, let's back up a little bit. This near death experience. Share more there. What happened there?

Yeah, I was so. I write books. I've written seven or eight books. And I had written a book called Peak Ability to Be Both the Learner and the Teacher. With respect for people younger than you and you're going to probably do pretty well.

That is really great advice. Today's episode is brought to you by Coda. I personally use Coda every single day.

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