Ep. 172: Airbnb’s Hiroki Asai on Designing Environments for Creative Teams to Thrive

May 31

Airbnb’s Global Head of Marketing, Hiroki Asai, grew up riding his BMX through the orchards of Cupertino, CA. But it was the visual language of skateboard culture that ensnared his creative imagination and grew into a passion for graphic design. Always industrious, he took night school art classes as a teenager, went on to earn a BA in Graphic Design, and then got straight to work freelancing. Not long after, he began working with Apple - eventually rising in the ranks to Vice President of Global Marketing Communications. Over his 18 years with Apple, he directly influenced the branding, packaging and marketing that we have come to know as distinctly Apple. Now, with Airbnb since early 2020 (through the tumult of the pandemic, the IPO, and a recent major reconfiguring of how Airbnb serves up wander lust and discovery,) he’s leading and supporting creative teams that are adapting and responding to the needs of a rapidly shifting global society. As a leader, he knows the most effective place for creative teams to be is right up close to the problems that need solving (aka in-house and upstream.) And to do their best work, the creative process needs protection and structure. Amen.

Hiroki Asai: I think a lot of people think that Creativity is like a lightning bolt that comes from the heavens and hits a gifted few and you have this idea and you kind of walk out with it. But the reality is, is I think, creative work and the creative process needs some kind of a structure to it.

Amy Devers: Hi everyone, I’m Amy Devers and this is Clever. Today I’m talking to Hiroki Asai, Global Head of Marketing for Airbnb. Hiroki grew up in Cupertino, CA and knew he wanted to be a graphic designer when he became obsessed with the visual language of skateboard culture. Steady in his convictions, he graduated with a Bachelor’s degree in Graphic Design from Cal Poly San Luis Obispo in 1991 and then got straight to work freelancing. In the late-90’s he began an 18 year stint with Apple - first through an agency and then in-house - as Executive Creative Director then Vice President of Global Marketing Communications…And Under his leadership, teams created the exceptional advertising, consumer touch points and creative expressions which Apple is known for today. Now as the Global Head of Marketing at Airbnb he’s been with the company through the onset of the pandemic, the IPO, and now the recent major updates to the platform, including Airbnb Categories, which radically changes the way we are able to search for travel. He steered Airbnb’s global brand campaign, Made Possible By Hosts and is actively and creatively engaged with in-house teams who are developing the products that are responding to and meeting the needs of a shifting society…And after all his creative contributions to culture… Hiroki remains, humble, focused and just grateful to be doing the work… Here’s Hiroki.

Hiroki: My name is Hiroki Asaii. I live in San Francisco, work in San Francisco. And I am the Global Head of Marketing for Airbnb.

Amy: I would love to learn how you got to be the person you are now. So I always like to take it back to the ground zero. Will you tell me about your childhood? Where you grew up what your family dynamic was like the kinds of things that fascinated you as a child?

Hrioki: Sure, sure. Sure. I grew up in in Cupertino, California, which is actually grew up about a mile from the Apple campus. Ah, so it's a it's been imbued into your very being. Yeah, it goes way back. It goes way back. I remember when I was a kid, I used to ride my, like my little BMX bike through a lot of the orchards that were around there that are all either Apple buildings or other buildings by now, but it was nice. It was nice.

Amy: So BMX bikes, what else were you into?

Hiroki: Really skateboarding? That was kind of my thing growing up, you know, there was I remember I think skateboarding is probably the thing that really got me into design, like me into graphics. To be honest, I, when I was a kid, I was just fascinated with skateboard graphics. And one of my, one of the things I used to love to do is we get a bunch of my buddies, and we go down to the local skate shop. And I remember spending hours and hours, just staring up at the wall of all the skateboards that were there, and all the different graphics and colors and finishes. And I can almost smell it today. It's like fresh urethane and surf wax smell. And you know, in the counters, a, we just had these beautiful colored wheels, and I would just be obsessed with just the imagery and the graphics and the whole subculture of it. It just drew me in.

Amy: What do you think lit you up about that? Was it the fact that it sort of associated itself with as another community or that it was just so maybe counterculture? Even it was not corporate?

Hiroki: Yeah, I think it was probably both those things. I just fell in love with the subculture, with the youth culture of it. I love the imagery of it. And this is all of course, you know, long time ago, pre internet. And so there was a lot of magazines and posters and oversized imagery and albums and music and graphics. Early to mid 80s, it was just intoxicating, all of that imagery. And I think that's where I really started to fall in love with the idea of just imagery, and what it could do and how powerful it was.

Amy: And did you start creating in that way? I mean, you were clearly skateboarding, but did you start creating your own images or drawing or thinking about how you could participate in that graphic culture?

Hiroki: Yeah, I always had a talent and a leaning towards the arts growing up. And so when I was in high school, I used to take art classes at night at the local junior college, and I would take drawing classes and design classes and photography classes, and so high school by day, Art and Design classes in the evening.

That youth culture really influenced the type of work that I was doing. And so, you know, kind of looking at it, being engaged with it. And then creating imagery also was just really satisfying.

Amy: So if you're going to high school during the day, and then taking art classes at night, does that make you a really industrious, like driven teenager? Or does that make you somebody who needed a creative outlet and wasn't getting it?Or a little of both?

Hiroki: I think a little of both, I think both but I've always been really, really, really industrious. I guess to use your word. I've always been a really, really hard worker. And so, you know, I knew early on that this is what I wanted to do. And so I wanted to be the best at it. And I wanted to take all the classes that I could I want to get as much exposure as I could.And so that's what led me to take these classes at night.

Amy: And parents were supportive of this?

Hiroki: Super supportive. Yeah, super supportive. I think just seeing me passionate about something and driven to do something and focused on something that helps, that helps. Yeah, that helps.

Amy: And if you're in school during the day and in school at night, you're not getting into trouble. So that must have helped you.

Hiroki: Yeah, exactly. Yeah, better. I'm taking photography classes at night. And God knows what so yeah, it kept me out of trouble.

Amy: So what were the other growing pains during during your teenage years, it sounds like you clicked into something, a culture and something that you wanted to pursue professionally, pretty early on, you got support from your parents, but like we all go through awkwardness when we're stretching into the adult individuals that we're becoming. So what was that like for you?

Hiroki: Part of the draw of that culture.That's skate culture, that's probably still at the draw today is there's just an element of danger to it, you know, and an element of critical mass to it, that it just feels like it's all going to explode at any moment. There's a lot of energy to it. And so, you know, I think being a teenager, that stuff is like, very exciting. You know, that imagery is very dangerous, and very exciting. And so I think it was fun to see it. It was fun to like, listen to the music and evolve with it, understand the imagery, the people, the artists, and then in turn, working on stuff and creating things that were part of that world also.

Amy: It's an it's an expansive process, isn't it? When you're the skate culture itself, like the graphics around, it dealt a lot with like momentum and speed and, you know, the physical danger that one might be imperiling themselves with in terms of, you know, skating to the extreme. But then there's also this intense camaraderie of the subculture that feels very much like a knitted together close knit network that you can kind of, be a be a part of, and people you don't even know can identify as, as friends. I guess what I'm interested in is, when you're, when you're participating in the creativity of that, and you're growing and you're expanding, you must have also felt your horizons just kind of feeling limitless. It doesn't sound like you are too angsty about it but some people are really worried about that. And it sounds to me like you're in a space where you're, you're growing. I don't wanna say completely wild, but you have all the resources you need to sort of fully flourish into your creative self.

Hiroki: I was also really driven. I mean, I was I kind of knew what I wanted to do when like sixth grade.I kinda knew that, like, graphic design was going to be my time a little unusual that way where I really, you know,

I knew what I wanted to do before high school, and I knew that graphic design kind of was my thing.

Amy: So that's what led your decision to go study graphic design at Cal Poly?

Hiroki: It did this well. I had looked into all the all the private art schools, but you know, we didn't have a lot of money back then. And so Cal Poly was great because it was a state school and I could afford the tuition and they had a pretty good design program at the time. And so yeah, I went there. Me being me and me being like super hyper focused and a little crazy, I went -

Amy: You haven't told me about the crazy part yet.

Hiroki: Yeah, I think crazy that I just a little too focused, I think.

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obsessive about the stuff, but you know, I went to design school or went to college study design, and then on summer breaks would go and do internships back home, in the Bay Area. And so I commute in the summertime and do internships during the summer and then I would go to school and do that stuff during the during the school year.

Amy: And this was this was pre computer right? So you're doing type by hand

Hiroki:This was way pre computer. So it was Yeah, hand inking with repeated graph pens and ruling pens, you know, drawing Baskerville and shooting it down on the stamp machine and yeah, waxing type and all of that stuff.

Amy: Do you ever miss that stuff?

Hiroki: I kind of do. I kind of miss you know, fiddling with exacto knives and cutting things out and trying to be really detailed at it.

Amy: There's a there's a hand eye coordination to it. There's a real tactility to it that. We don't get the same experience these days.

Hiroki: Yeah, there's something about having to draw a type and cut it up and look at it. It's your relationship to it changes. And it does. It's tactile, it feels like you're making something still, you know, has that tactile, really satisfying quality to it, which I miss.

Amy: When you came out of school, did you feel prepared? Did you feel like a professional? Were you like ready to hit the ground running? Or what were your first few steps into the professional world like?

Hiroki: I was pretty prepared. You know, I had done these internships over the summer. And I remember after my first internship that summer, I think it was even my freshman year in college. I realized like, wow, there's a lot of really good designers out in the world. And wow, there's a lot of art schools and wow, there's a lot of graduates coming to San Francisco. And I thought to myself, like wow, I really better work hard. If I want to get a job and like feed myself. And so I was pretty driven, you know, to absorb it as much as I could during the school year. And then I would do more internships in the in the summertime. But I learned pretty early on that you really had to work hard in this career. And you, you know, you really had to go for it. So I was I was pretty prepared when I came out. I started freelancing right away.

Amy: Oh, okay. Yeah, so freelancing means you were hustling for your own clients.

Hiroki: Yeah, and you know, back then it was all there was a lot of small design studios in San Francisco. I said to myself, Listen, I'm not going to be like the best designer, you know, I had enough self awareness to know that I was pretty good. But you know, I'm not the best, and I wasn't going to be the best. And so I said to myself, listen, if you're gonna succeed, you just have to really work hard.I told myself, I would be the guy that would go in, get a freelance job and do anything, and be happy to do anything.

Amy: Wow, that is hard working. I mean, do you feel like that was a good strategy? Do you feel at times that you maybe sold yourself out? Or, you know, didn't uphold boundaries got exploited?

Hiroki: Probably. We all go through that right. Yeah, we learned? Yeah, that work doesn't work. Yeah.

Amy: What would you say your strengths were, like a systems thinker. Where were your strengths and weaknesses?

Hiroki: I guess I always gravitated towards systems,especially graphic systems I really gravitated towards so I would say that was probably where my strength was atI think I just worked hard.

Amy: Hyper focus is your superpower. It sounds like.

Hiroki: Maybe, maybe, but I remember one of my first jobs. I was freelancing in the creative director wanted me to go and get his car washed, because he had to go pick up a client. And I remember him asking me and I remember answering going, absolutel. Anything else you need me to do?

Amy: Did you get a fresh banana and in Danish and leave it in there?

Hiroki: No, I should have.

Amy: So today, you're the Global Head of Marketing at Airbnb. But prior to this, you spent 18 years with Apple. And culturally speaking, those were pretty important. 18 years for the rest of us. And I'm wondering what it was like for you? What were the biggest lessons you took away from those years?

Hiroki: I think the biggest thing that I learned is just the power of what an in house creative team is capable of, could be capable of, as opposed to an agency. You know, back then, when we started the team, there weren't a lot of companies that were in sourcing, or investing in extensive creative teams in house. It was mostly outsourced to agencies. Now, I think one of the things I learned really quickly was how much more effective you could be being in house, because you're so much closer to the problem, you're so much further upstream. And if you're there, you can participate in things that you probably wouldn't have ever been able to participate in, in an agency and across other disciplines of creative and design, too. And so our group started as a graphic design group that ultimately grew into help launch the retail stores and do design work for the retail stores. And then also do you know, all of the product launches and the packaging and on and on and on, and the website and this and that, and all the videos and events. And so our remit kind of grew and grew and grew and grew and grew. And, I think the creators benefited because they got to work cross functionally across all these different disciplines. And across the entire business. I think the company benefited because it got much, much higher quality work, that was much easier to get done, and a lot more simple to work with, than a series of outside agencies. So I think I came out of that experience, realizing that an in house group if it's healthy, and structured well, and has a great creative CEO running the company, can thrive can thrive. And I think that group, and those creatives can do things that they otherwise wouldn't be able to do if there were agency.

Amy: And do you think that the product, the output is enhanced is improved? Because of that?

Hiroki: I think it is, and I think, you know, people can feel it. And I think the experience of the customer or the audience on the outside when they see all these things that are really

Amy: So considered. So intentional.

Hiroki: Yeah, really considered. I think that has tremendous benefits. I really do firmly believe that, you know, the way to do that is to be as close to the problem as possible.

Amy: As a designer that makes a lot of sense to me. And I can see the systems thinker in Hiroki really responding to that as well. You said a couple of things that I think are important, you said if the team's healthy, and if this team is structured well. So what are the characteristics of healthy and structured well, that are important?

Hiroki: Yeah, I think, healthy is these teams can really only exist in a creative culture. And we're lucky because Airbnb has an extremely creative culture. It's design driven, it's in the roots of its company. And you know, the, the founders are creatives as well. And so it's in its DNA. And so it's it's much easier for a team like ours to thrive in that kind of environment. And as far as structured, well, you know, I think a lot of people think that creativity is like a lightning bolt that comes from the heavens and hits a gifted few and you have this idea and you kind of walk out with it. But the reality is, is I think, creative work and the creative process needs some kind of a structure to it and it needs some rigor to it. And within that, I think you also need to, there's this ideation period that you really need to protect big time. Because you know, in that period, I think creators are very vulnerable. And they're tossing out ideas and questions and what ifs and asking why and testing those things and re examining them and testing them and re examining them. And that process leads to the idea of working through it. And the thing that kills that process is negativity bias. The thing that kills that process is someone saying, well, we've never done that before. That's not how we do it. That's not what works. And you have to suspend that negativity. And that bias in order to allow people to work through it to ultimately get to an answer. That's unconventional and different. And so I think you have to have a structure, environment, leadership that goes all the way up to the top that's really creatively driven, that can help to create and reinforce that, that ideation space for the process, you know, that very, very delicate period.

Amy: So there's that delicate period. And then once the idea is out of its delicate period, and starts to now need to respond to testing and be justified and, hold up against rationale and criticism. What is the structure there? I mean, you kind of hinted it at rigor, and deadlines. Were you particularly good at sort of measuring and marking out deliverables and milestones? And can you talk about that?

Hiroki: Another thing I think healthy creative team sets have to have is, like, amazing program management. And, you know, it's a lot, we have a very functional organization, the creatives, they're very much like organs of the body, you know, they're designed to do one thing, and one thing really, really well. But in order for it to function as a whole, you have to have a circulatory system that delivers information and data insights and whatever and keeps flowing to all the other organs. And that goes to a central nervous system and a brain that keeps the whole body moving.But it gives space for, you know, each of those teams to do what they're what they're best at doing.

Amy: I love hearing about healthy creative anatomy as a designer and an educator. That's what i I can only hope that, you know, all of my students can be able to creatively stretch their rank wings in a team environment like that just is what I hope for. For them. It's my highest aspiration.

Hiroki: It's a much more satisfying way to work.

Amy: Yeah.

Hiroki: My relationship with Apple started in the late 90s when it was kind of having its its second rebirth, and the work that we were doing, we didn't really know how impactful it would be or how big it would be or where it was all going. But, you know, we just, we just felt really, really lucky that we got to help in some way, you know, show the world these unbelievable products. And at the time, it was, you know, first the iMac, and then the iPod and everything that followed.

Amy: And if you've always been kind of a systems guy, then that probably actually really suited you in terms of being able to truly understand what it was that needed to be done across the whole network, and then being able to serve that.

Hiroko: Yeah, what's what's interesting is, you know, when you're a graphic designer, you tend to just think about the graphic design of the thing that you're working on. And what I learned over my years there is that, you know, people interact with brands in a whole myriad of different ways. It's not just that specific thing you're working on, they're influenced by the stories they're hearing in the press, they're influenced by the ads to see on TV, what other people are saying the packaging, the way that the store experiences, the way that the store attendant talks to you. And all those things that we all know, really, really become real when you're having to think within that context and tell a story across all that stuff. And so it becomes much larger than just graphic design or just filmmaking. And, you know, it becomes much more exciting and satisfying when you have to think across that entire scope of work.

Amy: Well, and as a consumer, I can say, I think that every aspect of the design, the graphics and the packaging, also start to tell a richer story. And make the whole experience that much more connective and exciting and soulful, when it feels like it's been designed from that kind of depth.

Hiroki: I think, you know, people are smart. And I think when they see something of quality, they know that it's a quality and that there's people that care about it. And I think that, that extends to everything, it extends to the advertising, it extends to the marketing and extends to the packaging, it extends to the website, the performance of the website.

Amy: Yeah, it's an intangible metric, but you can feel it, you can feel it. So personally speaking from from being just out of college into an executive, you had to grow into a kind of leadership role. How you doing?

Hiroki: I don't know. Ask the people I work with.

Amy: What was that like for you, though? I mean, like discovering your management style, and how you work with people and how you're able to, like, bring out the best and in your teams.

Hirokio: Yeah, it's funny, I there was I made a transition. I knew that I was a pretty good designer, but I wasn't a great designer, and I never going to be a great designer. You know, I knew my way around, I knew how to design things, but there's just a lot of really talented people out there. And so I at some point I needed I knew I had to make the transition from the doing that kind of the talking, and the transition to the talking was tough. Because your instinct is you really want to do you really want to do it. It was it was a tough transition, working with people knowing that they're really good at trying to get the most out of them trying to all right be on the same page and contribute without actually doing.

Amy: Yeah. And at the same time, the fact that you have a background in the doing means you can speak the language with a kind of alacrity. That means communication was probably imbued with a lot of empathy and understanding. And like, I know what I'm asking of you, essentially.

Hiroki: Yeah. I n a pinch, you know, in a pinch, I can get in there and edit or get in there and current for can still lighting and make stuff look better. And you know, it probably drives people nuts.

Amy: Whip out your exacto knife and you repeat a graph.

Hiroki: Yeah. Yeah. But I do have a lot more empathy, because I can understand what people are trying to do. And you know, what their processes and where the thinking came from?

Amy: So it's been a little while since Apple. You want to connect the dots for me? from Apple to Airbnb?

Hiroki: Sure. Yeah. So I left at about, you know, 2016. And, you know, I'd like to say I kind of like wandered the wilderness for for a few years. And thinking about kind of what was next what to do next?

Amy: Was that an existential wandering?

Hiroki: Yeah, it was interesting. I thought something would dawn on me that if I just left myself open, suddenly an idea would come or an inspiration would come and and some vision would arrive. But the reality is, it just didn't. And I ended up, you know, the only thing I succeeded in was just driving my wife crazy and driving my family crazy. All the time.

Amy: Yeah, the hyper focus guy with no focus, that must have been kind of a nutty time for you.

Hiroki: Yeah, it like, in hindsight, it probably wasn't the smartest thing to do. But I realized, you know, what I really missed is just working with a small group of people that I really enjoyed working with, you know, and it doesn't really matter what context that is, it just needs to be a group of people that I really enjoy working with, and working together on something and being needed. And you know, and I realized that, once you just focus on that, on just doing the work, the other stuff comes, like, what's important to you what the next step is, what's fascinating, the world will just kind of open itself up. But I guess, I learned you have to kind of re engage with the world in order for it to open up to you.

Amy: That's, that's pretty astute. And I think, I think that'll resonate with a lot of listeners, particularly in this moment, that sort of not quite post pandemic, but I think a lot of people are doing that sort of existential questioning and that reengagement with the world in order for it to open up. But I also think you said something really profound, which is that you knew you needed to be needed. And that's something that I've also really investigated within myself, and when I'm needed, then I really do feel like I can contribute in the most meaningful way. Because there's a pathway for it, there's like an avenue for it. And when I'm not needed, then it feels like I'm just trying to generate my own version of what I think might be needed. And that feels a little bit. I don't know, contrived or weird. So you like working with a small group of people that you really enjoy, and you need to be needed, and you need to engage with the world and you did all of those things by how?

Hiroki: I was doing a lot of advising and helping out with consultancy, and, you know, bopping around meeting people doing things. And then I got introduced to Airbnb through some mutual friends. I found it kind of fascinating. I found it kind of interesting. It was, it's a whole different generation of Silicon Valley than what I was used to, or what I had kind of grown up in, and it was just so different and exciting. And so it was fun. It was really a lot of fun. And then the pandemic hit, things are a little crazy. And, you know, they they really needed a lot of help. And so I helped out I dove in, and it was it was tough, and it was very, very intense, but I loved it. I loved it, and then I was lucky enough to be offered a position. And I really enjoyed the people there. So I took it.

Amy: So when you say you dove in, what does that look like creatively and professionally? Like what dove into what role? What were your How are you contributing?

Hiroki: Oh any way I could, with the amount of business that was lost and the turmoil, the pandemic, the turmoil at the world. Llike with any company, it was just going through a dramatic, dramatic change.

Amy: So does this mean like sort of looking at the world and brainstorm storming ways to adapt? Does this mean product development? Does this mean? Like actually take like a gut renovation? What does it mean for you to roll up your sleeves at Airbnb you specifically Hiroki?

Hiroki: There was just a lot of work to be done, and a lot of problems and things to be figured out. And what I did is I just approached it in the way that I was taught to approach problems, you know, as a creative. And so we looked at things from every single angle, looked at what the actual problem was that we were trying to solve, who we were solving it for, who the audience for it was. I think in times like those, you just work across a lot of different parts of the business, and a lot of different different parts of the company. I found it really exciting, I found the people really fascinating, I found that people really smart. And it felt good to be a part of something. And helping it in like this really, really, really critical time.

Amy: Well, the good news is Airbnb made it through pretty well, and is thriving. it's still critical. I mean, times are always, or seem like they're always critical. But how has your creative role shifted?

Hiroki: Well, what's interesting now is, is we're, we're doing all the creative in house, and we're building all these teams in house. And what's what's really exciting is, we're able to work off of one consistent insight that informs the PR that informs the product and ultimately informs the marketing. Okay. And I think what's really exciting now is that, you know, the world is like, just changing constantly, we're coming out of the pandemic, people are traveling, people are living very differently, people are working very differently. And therefore, people are traveling really differently. And when you think about all of those things that change, Airbnb plays a pretty big role and all of those things. And what's been really interesting is to see that insight of how people are living, how people are working, how it's changing how they travel, and being, you know, seeing how that thing gets applied, through the product teams into the product, and the features. And then in turn, how that gets applied into the press and the PR, and then ultimately, how it gets applied into marketing. And I think seeing all of that, and the connection of all of it together. Again, people are really changing and living and working is is super interesting.

Amy: It's fascinating. It's sort of macroscale sociology. It would seem to me that that very much informed these epic changes that just rolled out to the platform, specifically, I mean, I would love to talk to you about Airbnb categories, because that completely shifts the paradigm for how we search for travel, search for places to stay and it's not even just travel anymore, it might mean a temporary domicile because people are working, like you said, they're working in different ways. So what's fascinating to me is how Airbnb seemed to sort of, adapt in response to the way that society is adapting and meet it. You know, where it needs to be. And that's a really complex creative challenge that that you are taking on here with Airbnb categories, which let's just let's just break down what they are.

Hiroki: I love talking about categories because I love everybody categories. It's super interesting.

Amy: Oh, it's so exciting. I'm really excited by it.

Hiroki: Yeah, it's really exciting. And so what's interesting is there's there's life before the pandemic, and there's life after the pandemic. And before the pandemic, you pretty much had to live where you worked, right. And so that meant that you had 52 weekends a year, handful of holidays, and maybe a two week vacation where you would travel. And it was a system, if you think about it, because you had to be back in town on Sunday, in order to show up in the physical office on Monday, it seems so archaic now. For a lot of people, for everyone, that was the way we lived, and that was the way we traveled. And so in that world, you could have a pretty fixed system of search, because you know, you need a place for two days, you know, that you need drive time, you don't want to fly. And so your radius of where you can go is pretty limited. And so you know, that searching in that world is pretty fixed. But now with the pandemic, for a lot of people, things are totally different. And where a lot of us are, have flexible schedules or work totally from home. And so if you don't need to be back in a specific location on Sunday, why not just work from that place on Monday? Does the weekend have to be Saturday and Sunday? Could it be Monday and Wednesday? Could you add a day here at a day there. And so suddenly, you find yourself in a much more flexible place, right, and you find yourself open to a lot more possibilities of where you could go and when you could go. And so suddenly, that paradigm of fixed search doesn't really apply as much as it used to, right. And so what we realize is like, there's this huge world of possibilities that gets that gets opened up to people. And now they have the ability to take advantage of it. But they don't know that it's there. Because traditional search is crazy when you think about it. Because we'll say okay, Amy, where do you want to go? Right, and you have to type in someplace where you want to go, and you're probably going to think of like five or six places. But there's a lot of places you would never know to look for that exists that are available for you. Right? Especially if you're a little bit more flexible. The analogy I love to use is it's kind of like an ice cream store. Or you walk in and you don't see any of the flavors. And you have to tell the person behind this counter. What flavor you want. Right, and you're probably going to like, pick five flavors, vanilla, chocolate, whatever,

Amy: Mint chocolate chip and pistachio. That's all I can think of right now.

Hiroki: Yeah, but you would never know about salted caramel, you would never know about matcha chocolate chip or whatever they have underneath the counter because you just don't know to ask for it. Right?

Amy: Rosewater and Tobacco? Yeah.

Hiroki, Exactly. Yeah. And so the great thing about categories is it really showcases all of these unbelievable listings in these super unique location categorized in a way that really makes them unique. So, like, the design category is unbelievable. I'm sure you've, you've checked it out.

Amy: Yes, yes. I've spent hours in the design category. And I'm, you know, I feel like my prayers have been answered because as somebody who when I travel, I always seek out architecturally interesting places. That's what appeals to me. That's what's important to me. And before it was always like a needle in the haystack kind of hunt, just Googling architects names, and then trying to find out if it was actually available to rent or, but now, it's a smorgasbord of options. It's like the best buffet ever.

Hiroki: Yeah, it's amazing. It's totally amazing. And, you know, you would never know about these places you would never even know to look for them. Like unless you're searching in Ann Arbor, Michigan, you may never find some of these Frank Lloyd Wright's that we have.

Amy: And Ann Arbor is not a popular vacation destination that comes to top of mind. And you know, what else it does is? You know, I've always loved a road trip for that same reason is because you find these like, out of the way places that you didn't know existed, but now you could even plan a road trip and search the design category along your route. And wow. It's really exciting.

Hiroki: Yeah. It's incredible. If you go on the site, there's a jewels Gregory home in Lambertville, New Jersey. Now, I've never been to Lambertville New Jersey. But if I'm in the area, I'm definitely going to stop by and check out that house.

Amy: Well, you can also plug in recording studio, which as a podcaster is something that appeals to me. I wish I was a musician, but I'm not. But if there's a recording studio, I'm thinking, I can probably work from there without bringing lugging my equipment with me. And I can go spend a month in Nashville. But of course, it'd be pretty expensive with a whole recording studio in the house. But I just think it empowers discovery in a way. That wasn't an option before when you had to plug in a specific geolocation plus dates.

Hiroki: Travel is like one of the most exciting things we do. It's one of the most exciting, exciting things that we could do as humans and searching for that trip. And thinking about that trip. And planning that trip is almost just as fun as taking that trip. Right? And so why shouldn't the process of discovery be as exciting as the trip itself?

Amy: Yeah, well, I now I've got houses saved, that I'm looking forward to. Which I wasn't for, you know, for a couple of years, during the pandemic, I sort of, I think like all of us, we kind of our worlds got kind of small, and we lost a little bit of hope. And so now, even if I can't travel, right, this minute, I can go there in my mind, and I can start planning and I can start feeling those aspirations that I think are actually really important to all of our mental health at this point.

Hiroki: Yeah. And as a guest, it's, it's great, you know, because you can see all these places, and you can wish list and like, like you did, and discover new homes, and maybe even think about trips just to visit these homes or, or work from home. You know, but also for hosts. It's fantastic, because it allows their unique places to be discovered, in a way that otherwise probably would have never been discovered, you know, and it also showcases what's unique in a way that you couldn't do fix search.

Amy: And the InDesign category is something you and I can bond on because it's my favorite. And I hear it's your favorite, too. But there's so many other categories. How many categories are there?

Hiroki: Yeah so it's over 50. Wow, categories. Yeah, there's basically a category for everyone, I think.

Amy: Okay. Why is the design category one of your favorites?

Hiroki: Oh, I mean, easy. I mean, you should just check out the houses in them. They're unbelievable. I mean, talking about dreaming, there's just some unbelievable homes in there. Frank Lloyd Wright's, homes that were featured in wallpaper, Jules Gregory, Le Corbusier.

Amy: Not only can you find them now, but, I'm a designer and a design educator. So I'm also particularly attracted to the kind of educational value of attributing these houses to the architect or architecture studio that's responsible for them, because I feel like that's the human link that we all need to sort of make the house less anonymous, make the actual contribution of this kind of architectural creativity to our built world, like have a human anchor and be able to celebrate it and value it. And it's fun for me to scroll through and learn like, Oh, that was done by that studio. That's great. I didn't know I could rent that. And I'm also learning a lot about architecture and other parts of the world by being able to scroll through the different categories, even yurts and windmills is - those are architecturally significant. And now I can scroll through it and really kind of give myself a lesson and culture and design, because it's organized like this. It's very exciting.

Hiroki: Yeah, yeah. It's it's so much more of a fun and satisfying way to think and search for travel.

Amy: So, back to you, through your 18 years of Apple not really being aware until you have hindsight that you've participated and contributed to a major culture shaping era are you able to recognize now any of the signposts of that? Now, like, do you feel like you're doing something important and impactful?

Hiroki: What I'm really most proud of, are the teams that I've been able to work with, you know, and the team that we've assembled at Airbnb is, is pretty amazing. And it's just an amazing group of people. It's really, really fun to work with and super talented. I'm really proud of the fact that we're able to create such a powerful in house creative team that can do everything in house, which is really rare these days. And I think it takes a special kind of leadership at the company's special kind of culture of the company to make that happen. And I've been lucky enough to experience that once. And so experiencing it twice is pretty phenomenal.

Amy: You've painted a picture of a creative team, that's actually able to get a lot done, because you're in house. And part of it might be the actual people you're working with, you've got a great team. And part of it might be the in house, part of it. I see a parallel back to the kind of camaraderie that that first attracted you to skate culture, but I'm wondering if you can feel culture shifting from the sort of creative genesis of it like where you are?

Hiroki: Back when I started a lot of creatives, we're out of house, and we're in agencies, and I think a lot of companies are now making the shift towards building these in house creative teams. And I actually think it works better, to be honest. And but there's, you know, there's definitely a trick to it. And there's definitely a way to make it work well. And I think at Airbnb, we definitely have a design driven culture, we definitely have a creative culture. And so our teams tend to flourish and prosper there.

Amy: Okay, Hiroki, I have thoroughly enjoyed your story. And I really appreciate you sitting down to talk with me. Before I let you go, I just want to know what direction you're pointed in, like you did your existential wandering through the wilderness, you've you found a new place to be needed. And what direction does that mean your compasses pointed in?

Hiroki: It's pretty simple. I think it's just doing the work. To be honest, I think it's just making sure that we have a healthy team. That's thriving, that's excited. And it's just really doing the work, you know, and it's taking it day by day, and ultimately, just making sure that everyone's having a good time.

Amy: Having a good time. That's something I think we're all looking forward to after these harrowing couple of years. Well, thank you for your role in making it easier for us to do so. Thanks, Hiroki. It was really nice talking to you.

Hiroki: Nice talking to you today. Thanks for the time.

Amy: Thank you for listening! To see images of Hiroki’s work and read the show notes, click the link in the details of this episode on your podcast app, or go to cleverpodcast.com where you can also sign up for our newsletter, subscribe to Clever on Apple Podcasts, or wherever you get your podcasts. If you would please do us a favor and rate and review - it really does help a lot! We also love chatting with you on Twitter, Instagram and Facebook - you can find us @cleverpodcast. You can find me, @amydevers. Clever is hosted & produced by me, Amy Devers with editing by Rich Stroffolino, production assistance from Ilana Nevins and Anouchka Stephan and music by El Ten Eleven. Clever is part of the Airwave Media podcast network. Visit airwavemedia.com to discover more great shows. They curate the best of them, so you don’t have to.

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What is your earliest memory?

Making coffee from this morning

What’s the best advice that you’ve ever gotten?

Mature trees are the most valuable thing on the planet because no matter how rich you are, you can’t get one in your backyard. You can only get one over time.

How do you record your ideas?

I write down everything. I use 8.5 yellow legal notepads, post-its, scrap paper. All analog.

What’s your current favorite tool or material to work with?

Post-its.

What book is on your nightstand? (alt: What’s the best book you’ve read this past year?)

The best book I read this year is The Goldfinch, by Donna Tartt. I loved it.

Why is authenticity in design important?

Who doesn’t appreciate authenticity?

Favorite restaurant in your city?

Zuni Cafe in San Francisco

What might we find on your desk right now?

PIles of post-its and 8.5 x 11 yellow pad paper. Reading glasses. Coffee carafe. Aesop hand balm.

Who do you look up to and why?

I look up to my kids. They are young and totally free of bias. They are completely untethered in their creativity.

What’s your favorite project that you’ve done and why?

We built a mini-half pipe in the house. This was a childhood dream.

What are the last five songs you listened to?

i listened to For Whom the Bell Tolls, Metallica; Native Son, CCR; Ray of Light by Madonna; Between the Bars by Elliot Smith; Something in the way by Nirvana

Where can our listeners find you on the web and on social media?

Every nine days, they can find me on LinkedIn; and about every eleven days, they will find me on Instagram.

Clever is produced and hosted by Amy Devers with editing by Rich Stroffolino, production assistance from Ilana Nevins and Anouchka Stephan, and music by El Ten Eleven.