So let’s start with the beginning. Tell me about your early years and where you come from.

Early years. I was born in Youngstown, Ohio, which is this sleepy little steel town right on the border of Pennsylvania. My parents, who’ve been split since I was two, both got job offers at the same time in Florida and took it as kind of providence, and so the whole family moved down there. So my mom still lives in Orlando, and my dad lives in Tampa. Went to high school in Orlando, and then college in Florida. And eventually I to New York for grad school. Worked there a little bit. Bounced around the country a little bit. A few different places. And then wound up here in October.

How’d you get into design and/or tech?

It’s interesting. So for undergrad, I studied politics. I didn’t think I was going into design at all and then started working in non-profits. This was right at the onset of the recession. So non-profits didn’t have the money to hire me to do anything, and they also didn’t have money to contract things like design. I had taught myself a little bit of Photoshop, and those were my first clients, where I was trying to build something to try and find ways to freelance and make money. I got into design from a perspective of wanting to do more social good projects, through more graphic design projects.

“I knew San Francisco, culturally, was on a short list of places I always wanted to live someday, but I didn’t ever have it as a target. I felt like it was a little bit of a whirlpool, where eventually, all designers who work in tech, find their way to San Francisco, and some stay, and some get spit right back out and keep going.”

It wasn’t until I went back to school for grad school, to actually formally study design, that I realized I was actually also very interested in technology. I was particularly interested in the way that games were now doing these more interesting, immersive narratives, and how they were really reaching, when they were done right, doing these really amazing things that were on a level of novels, that were even beyond film, because you spend so much time in the game, versus a two-hour film. That interest in mediums and technology then started me doing more design work in that realm.

I knew San Francisco, culturally, was on a short list of places I always wanted to live someday, but I didn’t ever have it as a target. I felt like it was a little bit of a whirlpool, where eventually, all designers who work in tech, find their way to San Francisco, and some stay, and some get spit right back out and keep going. I knew a few friends in New York who felt that way, or were from San Francisco and were still trying to escape it as long as they could, paddling away. I didn’t really know what to expect.

“As a designer in New York, the design community is very much about—it’s still very much analog. Publishing is still the main realm of design there and fashion, and you find different kinds of specialties. But most of them are still clinging to the analog world. There’s actually not a lot of tech designers or people who are super-enthusiastic about it. Most of the people are still trying to make an Etsy shop or revive some kind of ancient typeface, and that’s fine. That’s really cool, but it wasn’t my thing by the time I was done with school.”

As a designer in New York, the design community is very much about—it’s still very much analog. Publishing is still the main realm of design there and fashion, and you find different kinds of specialties. But most of them are still clinging to the analog world. There’s actually not a lot of tech designers or people who are super-enthusiastic about it. Most of the people are still trying to make an Etsy shop or revive some kind of ancient typeface, and that’s fine. That’s really cool, but it wasn’t my thing by the time I was done with school. And so a part of me was always thought New York was the center of the world for design. And I think I started to realize as I embraced the idea of moving out here that Silicon Valley might be the center of the universe for design and tech and that I might find more like-minded designers coming out here where I would be in the majority for once of most people like the technology side of things. And now the hipster typefaces are now on the fringes of the design world over here. And I think it’s more or less met that expectation. I think I’ve been more thrown by the West Coast cultural values more so than anything about Silicon Valley itself, I guess.

It’s definitely different from New York.

Yeah, very different. Although, I’ve heard that it’s not as different as it used to be. I was having this conversation with a friend not that long ago, and we were talking about how with the influx of New Yorkers it’s starting to kind of Manhattan-ize a little bit of San Francisco. And you can see it in certain neighborhoods where there’s still this kind of more hippy vibe of laidbackness. I lived in Austin for a while, and so my only comparison is to say that it’s just more of an Austin-y kind of neighborhood of more laid back people. So I feel like that has been the more surprising attention getting thing for me. More so than even any kind of preoccupation with my job, or the other people I work with, or anything.

Yeah it’s definitely changed a lot since it’s become more of a melting pot from other cities. Like people dress well now.

[laughter] That’s pretty cool. That’s a positive, I guess.

Yes. Definite positive, and there’s actually places to eat after 9pm now.

Yeah. So it’s funny that I’m finding in myself that I’m building connections faster with people who are from New York. And I feel weird about it because I set an expectation of moving out here, and kind of embracing a different world for a little bit, and I feel myself, and I don’t know if it’s as I get older I’m less open to these kinds of new experiences, new places, and so I’m just being a little lazy, and gravitating towards people that remind me of places I’ve been before.

I get it.

I also feel weird because I feel like I am the cliche. I am the designer from New York coming to work at Airbnb, and that becomes this emblem of what problems ail the Mission and other neighborhoods. So I feel like whenever I hear people talking about Silicon Valley and San Francisco, I just kind of shut up and listen. I don’t feel qualified to comment yet on it.

“I also feel weird because I feel like I am the cliche. I am the designer from New York coming to work at Airbnb, and that becomes this emblem of what problems ail the Mission and other neighborhoods. So I feel like whenever I hear people talking about Silicon Valley and San Francisco, I just kind of shut up and listen. I don’t feel qualified to comment yet on it.”

It’s a weird time.

Yeah.

Let’s go deeper on that in a minute. What is really exciting to you about your work? What are things you’re super proud of, what are things that really activate you right now?

I try to read a lot of philosophy actually, and I think I’m learning that that’s not usual for a lot of designers. A lot of designers are very interested in the aesthetics of things, and I’m really interested specifically in how the aesthetics influence behavior change. So the visuals are actually more of a means to an end for me. In that realm you find all kinds of really interesting philosophical questions. It’s a shame that it goes over so many people’s heads, because I wish they were reading more of the stuff I’m stumbling across.

“I try to read a lot of philosophy actually, and I think I’m learning that that’s not usual for a lot of designers. A lot of designers are very interested in the aesthetics of things, and I’m really interested specifically in how the aesthetics influence behavior change. So the visuals are actually more of a means to an end for me.”

Some things I’m interested about that make me so interested in this topic are things like Sherry Turkle, she was an MIT roboticist. She wrote this relatively cynical view of the way machinery is actually changing human behavior in cognitively lazy ways, which is interesting, again because she’s an MIT roboticist. For her to have a cynical view on tech makes you turn your head and listen to what she has to say. And then I like going into other stuff, like Umberto Eco talks about hyper-realities and these layers of reality on top of the real thing and all the moral quandaries in this. When you work in tech you are, in many cases, building a virtual version of things that– you’re not blind, you look around when you’re side and everyone’s on their phones and you’re building that – as Baudrillard would have called it – like the kind of map on top of the real world. You’re building that virtual on top of the real. So I think those, because of moral problems which I’m not always feeling like I’m on the right side of sometimes, also keep it interesting in a kind of “hard questions to answer kind of way” that make me kind of get up every morning and keep doing it.

Yeah, it makes sense to me that you’re feeling this way—as someone who’s lived in New York City, we have a heavy specialization culture here compared to there. In my experience, knowing about other disciplines were considered detractors from your specialty.

Interesting.

Being a generalist of any kind was frowned upon for a while. And so going to New York which is so not a one industry town, and how it was wildly different in that way. In New York, it was more like “Oh, what do you do? Okay, what else do you do, what other projects do you work on, what else are you into?” And I notice how that mentality affects the two cities tech cultures differently.

I can see that totally being a factor too, just like their density, right? Because there’s so many design tech workers here, they started to have to specialize to keep steady work, or to find their niche, or whatever. And in New York, again being on the fringes a designer in tech, you couldn’t always count on tons of design tech work, so you were probably pulling other skill sets to kind of stay afloat during all that. I could see that being a factor. New York in general though, I think just from the way it’s built, down to its demographic makeup, is just this collision of all kinds of crazy ideas, that– maybe you’re right, maybe it’s like a cultural thing that forces everyone to be a little bit more of a generalist there.

“The latest project I worked on, been working on it for about four months, and for the first three months I didn’t design a single thing. It was a lot of me leading up to the idea of the project, me working with content strategists, me working with researchers, me sorting through data sciences, tons and tons of previous experiments they’d run. There’s just a lot of immersion in all of the different things around the thing before I actually set pen to paper to make something. I don’t know if that’s typical of other designers yet; it doesn’t seem to be. I feel like other people are rushed into making something and they don’t fight back, and so they do that. Whereas I’m a little bit more opinionated about how I want to do it, and I’ll usually fight for that time before something actually gets made.”

Yeah. How do you think that background impacts the way you create your work here?

I’m slower [laughter]. Because I take in time to weave and detour and walk away from my desk for a while, and think about it, or read something and let it see how it kind of shapes my opinion of something. I’ve only been here since October, so I’m still kind of getting that sense of how it’s going to shape what I do. I think I’m more likely to write an essay on why I’m taking a design approach than I am to quickly and quietly say what I’m presenting today. It can only really compare to how I’ve seen other designers in my office talk about their work. For example, the latest project I worked on, been working on it for about four months, and for the first three months I didn’t design a single thing. It was a lot of me leading up to the idea of the project, me working with content strategists, me working with researchers, me sorting through data sciences, tons and tons of previous experiments they’d run. There’s just a lot of immersion in all of the different things around the thing before I actually set pen to paper to make something. I don’t know if that’s typical of other designers yet; it doesn’t seem to be. I feel like other people are rushed into making something and they don’t fight back, and so they do that. Whereas I’m a little bit more opinionated about how I want to do it, and I’ll usually fight for that time before something actually gets made.

Which makes sense when you are designing for a complex problem involving a lot of people.

And this is a relatively simple environment. I worked at IBM before which has massive systems at scale; it’s impossible to really ever feel like you’ve solved a problem. The job that I just most recently was working was in mobile advertising, so we’re talking about a moment, just a microinteraction to design. So I’ve seen all sides of that from a fraction of someone’s attention to tons and tons of people involved in the system. And so this doesn’t even feel as if it’s particularly hard in either one of those directions. When I get my way I get to spend lots of time thinking about something before I move on it, but you don’t always get the luxury.

“I’ve moved quite a bit for different jobs. And the last year or so that’s started to catch up to me where I wonder how that’s affecting my relationships.”

What have been some of your biggest struggles and roadblocks over the course of your career?

Struggles and roadblocks. It’s been some interesting ones. I’ve moved quite a bit for different jobs. And the last year or so that’s started to catch up to me where I wonder how that’s affecting my relationships. All my friends here even, who have lived here for ten years, and they have such deep roots with so many people and even when you move you stay in contact with some people, but even as close as you might feel when you live in the same city once you disconnect a little bit over time that all decays. And I realize that I don’t have a lot friends beyond the last two or three years just because, after you move around a couple of times you lose touch. So I feel like my job is kind of impacted. That’s been a challenge of the job. If you’re chasing the next best thing that’s always being offered to you, as exciting and as fun as it is to get better at what you do, and be doing more and more of what you love, you’re making all kinds of small sacrifices along the way that add up over time.

“If you’re chasing the next best thing that’s always being offered to you, as exciting and as fun as it is to get better at what you do, and be doing more and more of what you love, you’re making all kinds of small sacrifices along the way that add up over time.”

There’ve been weird ones too like; when I moved to Austin for IBM, it was before the Supreme Court had passed the gay rights legislation last year. So that was a weird one because I was living in New York where I could marry or date or hold hands out in public and never really think twice about it, and I got used to it after a couple years living there and then getting a job offer in Texas was the first time I was like, “Oh, I have to actually give this up.” I didn’t think it would  be as big of a deal until I got there. It really kind of messed with me for a while. Eventually, that was what I went to IBM with and said, “You moved me away from the state where I could be me and now I’m like a half citizen here. Especially in Austin at the time the governor was comparing homosexuality to alcoholism. And that’s two years ago, this is not like an exceptional amount of time. It was eventually why they let me move back to New York from Austin. So there’s been little things like that for my jobs and careers and stuff like that for a while not all the states were equal and you couldn’t just move to wherever the opportunities were. You had other things to consider. Luckily that didn’t last too long for me.

“I was living in New York where I could marry or date or hold hands out in public and never really think twice about it, and I got used to it after a couple years living there and then getting a job offer in Texas was the first time I was like, “Oh, I have to actually give this up.” I didn’t think it would  be as big of a deal until I got there. It really kind of messed with me for a while.

Yeah I’m from North Carolina and with their recent politics I can’t help but be like, “You guys are fucking yourself talent-wise.”

It really was a thing. IBM had set up this office in Austin because it was so much cheaper. Texas has done all these great business incentives to move these kinds of big companies to startup centers like that there. It was a weird place to try and recruit a designer because even though Austin’s great it’s still Texas. So it’s not exactly near any design mecca’s to draw people in. I remember that was something that cost them. I wasn’t the only person there was other people I know too that would struggle. People they were trying to recruit were like “Why would I move there if I can’t be who I am? What’s the point?” That was kind of eye opening. For a while there things were kind of half and half. So I’m glad that it didn’t last very long.

“Regarding tech, it’s interesting because statistically gay men are paid less than average, but gay women are paid more. It comes down to body language. If they’re more effeminate, they’re paid more like women and when lesbian women act more masculine they’re paid more like men which is kind of still a sad commentary on why that’s even a thing that we pay differently.”

Now being in San Francisco, what’s your experience been as a gay designer?

I’m a cliche now. [Laughter] I feel like you get into any kind of Lyft-sharing experience and you talk to the other passenger and they’re like, “I work at Facebook,” and you’re like “I work at Airbnb.” It’s almost nauseating sometimes how many people are working in similar spaces. It’s funny because if you remember it’s kind of what I asked for. I wanted to be around like minded designers. The gay culture in general is funny here in San Francisco. It’s different in a lot of ways. Regarding tech, it’s interesting because statistically gay men are paid less than average, but gay women are paid more. It comes down to body language. If they’re more effeminate, they’re paid more like women and when lesbian women act more masculine they’re paid more like men which is kind of still a sad commentary on why that’s even a thing that we pay differently. So I feel like also that gay people in general, because of the stigmas they’ve grown up with and depending on their homelife as they came out and all those different factors, like it’s a more, I don’t know—I feel like you see fewer gay men aggressively pursuing a career, becoming super successful. Like you find much more of a mixed bag, I feel like. And so, as a gay design tech worker, I feel like I’m kind of in a different bubble from other people. I don’t know. I suppose it’s no different than like any other kind of straight relationship or groups or something like that. But it is kind of its own little bubble, and again, this is more of a San Francisco thing, that like tech workers aren’t always super welcome depending on the party, depending on the group of people, and so you can sometimes feel a little weird. And in an environment where being gay should be like the unifying thing that keeps everyone in the group feeling close to one another, that can actually be kind of an undertone of a kind of rift in the room sometimes which is weird. That was not a thing in New York. There was no industry that was hated or like despised. And New York has some slimy industries like Wall Street and stuff there and there was still nothing like Airbnb that could divide gays. It’s more political here and that often trumps sexual orientation.

“Tech workers aren’t always super welcome depending on the party, depending on the group of people, and so you can sometimes feel a little weird. And in an environment where being gay should be like the unifying thing that keeps everyone in the group feeling close to one another, that can actually be kind of an undertone of a kind of rift in the room sometimes which is weird. That was not a thing in New York. There was no industry that was hated or like despised. And New York has some slimy industries like Wall Street and stuff there and there was still nothing like Airbnb that could divide gays. It’s more political here and that often trumps sexual orientation.”

On that note, what is it like straddling those two worlds? Tech and the queer community?

It’s weird. Like when you’d posted your call for subjects for this project, and there was one question about something like you were interested in things like minority backgrounds, or stories, or something like that. And that’s always such a funny thing, because I remember coming out and someone saying something to me about being a minority, or something like that. It was bizarre because I came out—I was 21 I think—and for 21 years I was a white male. I was the most privileged demographic in human history. I never thought I was being discriminated against for anything except for unfair advantage [chuckles]. And so then to suddenly come out, I was suddenly in a different group that was very marginalized. But I feel like I get it easy, because even there I’m not especially effeminate where that might be something that- it’s rare that someone from across the room is like, “Oh, you’re gay” and then I have to work with that. I can kind of go incognito if I want to, or need to, or something like that. So it’s not out of my control to control those kinds of stigmas sometimes. I still don’t fully identify as a minority. I feel my advantages still far outweigh any kind of setbacks and I think I was fortunate enough to live in a time where all of these things were rolling back. I mean, we forget, but 2007 and 2008 had huge bands happening across the country, and all of that reversed 180 degrees in a few years. I happen to have had my career rise at a time where all that was very quickly becoming normal. And so I don’t think that actually hurt me as bad as it certainly would have hurt other people even 10 years ago. Now we have Tim Cook head of Apple. So the stigmas I have to deal with are fading fast.

“I remember coming out and someone saying something to me about being a minority, or something like that. It was bizarre because I came out—I was 21 I think—and for 21 years I was a white male. I was the most privileged demographic in human history. I never thought I was being discriminated against for anything except for unfair advantage [chuckles]. And so then to suddenly come out, I was suddenly in a different group that was very marginalized. But I feel like I get it easy, because even there I’m not especially effeminate where that might be something that- it’s rare that someone from across the room is like, “Oh, you’re gay” and then I have to work with that. I can kind of go incognito if I want to, or need to, or something like that.”

Yeah, still need to get him for this project.

[laughter]

Kind of random, but you’re a colorblind designer. How does that work?

Yeah, it’s funny, some jobs I tell right off the bat, and some I don’t. I told Airbnb right off the bat, because the last one I tried to keep it a secret. It was almost as a game to see how long I could go before it was obvious. And I made it through the whole time I was there, and I never told anyone. In fact, I teach at General Assembly, I teach Visual Design and there’s actually a whole class that’s going to be next week on color theory, and I’ve taught that every single time without ever telling the class that I’m colorblind. So you can get by. I think some people misunderstand colorblindness. I see probably see like, 70-80% the same thing that everyone else does, so it’s not as dramatic. So it’s really only a couple of shades that as long as I avoid trying to call out that green button, or that blue text, when it’s actually purple or actually red or something like that, I can get by just fine. But there’s actually a host of like digital tools nowadays that make having to verbalize a color or something kind of unnecessary.

“I teach Visual Design and there’s actually a whole class that’s going to be next week on color theory, and I’ve taught that every single time without ever telling the class that I’m colorblind.”

You can just talk in hex code or something.

Exactly, with a lot of designers, it’s like a hex code that you are just copying and pasting anyway or even a Pantone that you are just memorizing the number of. And I even can take the hex code and if I just Google like “What color is this…”, there’s a website but I can’t remember the name of it that always pops up top, and I go in there and I can paste the hex code in it and it actually describes the color too. And so it will give me description and it will say this is the shade of yellow. And so if I am working within a palette that I know I’m going to be using a lot, I can almost always sense their balance to one another without having to see the exact, exact shade. But if I’m ever on the fence because it’s some kind of weird in-between color, I can always look it up that way and save myself.

There’s only one bad time that I actually worked with Milton Glazer in New York, which is an amazing opportunity. But he did a famous, very iconic Bob Dylan poster with, you know, the silhouette of Bob Dylan, all these really colorful wacky hair. And he had it in his archive the original one and he was talking about how they needed to re-evaluate the colors for some kind of new print job they were going to do to reprint it. He asked me. He said, “Can you go down to the cellar, get the poster out, and I need you to kind of match pantone colors so that we can reprint this.” and I immediately started to panic and have anxiety, because that is the absolute worst—that is the number one thing as a designer that I still could never do is take a color wheel and match exact shades, especially for such an iconic reprint of such a big work and, thank God, before I had to answer this, one of his other assistants said, “Oh, no, I did that last week.” And she had the notes and I slumped back into my seat. That would have been bad I would have had to admit that to him. I don’t know how he would have reacted.

Oh, man. I think back on how many meetings I sat in in tech deciding—spending so much time over the difference—like the tiniest difference between shades of salmon.

Totally, yeah.

Salmon.

I would have a harder time in like a branding agency where you’re coming up with brand new color pallets, but because I’ve usually worked in like in-house teams where you have a brand and you have colors to work with—and even at Airbnb we have a graphic design department where they specialize in visual design—and so I’m happy to let them take the reins on stuff like that because obviously that’s not my specialty. I can do a lot of good things, but that’s not one of the things I try to do.

But there’s been a lot of famous designers, believe it or not. Like, Tibor Kalman was another designer that was actually color blind. He actually founded Colors magazines and did lots of branding projects, and I’ve heard funny stories of him doing client presentations where he would just kind of be like, “And your green…” and then look to one of his assistants and they would just kind of point to the right one and he would move his finger. All these systems, they worked out before they could cheat with computers like I can. If you’re passionate about something you want to do then you find a way to work around it even if you have a little setback like that.

Let’s talk about your mentors. You’ve worked for some really great people—how have they shaped you and your career?

Yeah, sometimes I’ve had a mentor where they’re amazing and I’ve learned what to do, and sometimes they’ve been an example of what I don’t want to do, in pretty major ways. I think positives have definitely been all of them have encouraged me to teach, early in my career, and so I sought out a position with General Assembly last year in New York and started teaching their visual design class, which is perfect because I do it on Mondays and Wednesdays —it’s just two hours. I’ve done it a couple of times now where I know the curriculum pretty well. And it’s great for a lot of things. It’s humbling to go back to the beginnings of design and explain some of those things to people for the first time, and realize how much you’ve learned and how far you’ve come. So I really enjoy that and I think it’s also great to feel like you are helping people get excited about something you get excited about. Even just this week, because I’ve been rehearsing some basic principles with students, they were fresh in my mind and I was solving problems at work using some of the same basics. It’s easy to forget about them when you’re not rehearsing them on flash cards every day.  

“Sometimes I’ve had a mentor where they’re amazing and I’ve learned what to do, and sometimes they’ve been an example of what I don’t want to do, in pretty major ways.”

I think, I’ve also—people like Milton Glaser, Stefan Sagmeister, these kinds of icons of design, at least in the New York scene, less so here for some reason, I think because they’re graphic design. They’re great but they’re also kind of monoliths. They’re like examples that you can’t really follow because they’ve either had these insane success stories of how one design they made just blew up or they came from wealthy backgrounds where they can afford to just float on their family’s wealth while they launch their own studio for years and years and finally work their way up. Or they’re kind of dicks to everyone but that just worked for them because they had the right connections to make it happen. So there’s just been a lot of interesting examples. Milton’s a funny one because he’s 84 and still doing amazing work, still sharp as a tack. Working there was like working next to a philosopher where you could ask his lunch order and he would just say the most profound thing you’ve ever heard, right? But by the same token was totally dismissive of technology and kind of a cranky old man at times about where design was headed and a little bit cynical. And so, meeting your idols is always that dangerous, you know, the cliche of “never meet your idols”. It can be dangerous because they’ll inspire you in so many ways and in many ways be different from you. And sometimes that can challenge—maybe in a good way, maybe it challenges you in a good way because you hold onto the things that even that person, that amazing person that you always looked up to was unable to really change about you.

What do you think your biggest motivators are?

I like fixing things, and I guess that’s like the most basic way to talk about it. Like, it’s a problem solving act when you design things, and so I’ve worked in a lot of strange, disparate industries—like Victoria’s Secret where you’re around supermodels to IBM where you’re not around supermodels and it’s like engineers in dad jeans on these weird antiquated campuses on these weird softwares, to like mobile advertising which is a terrible industry but has so many interesting psychological problems to try and play around with. And I think the connecting thread between all of them were that they all just had some kind of interesting problem to solve. Even Victoria’s Secret, which is a brand that can easily be mistaken as being about supermodels and lingerie and angel wings and stuff like that, actually had a very sophisticated e-commerce platform and they were solving really interesting problems around like how do they in real time adapt this system to show people the exact products they’re interested in, and just the coordination between all these different teams was actually really fascinating.

“But something that’s bothered me recently is I’ve realized that even though I’ve always enjoyed solving a problem, that high kind of fades after a certain amount of time, and then I get kind of bored with the problem. And I’ve realized that it needs to be something more than that, that there’s been a handful of times where I was actually really passionate about the topic and I was really interested in the problem. There’s only been a handful of times where those both existed for the same project, usually it’s just the problem I’m interested in solving.”

But something that’s bothered me recently is I’ve realized that even though I’ve always enjoyed solving a problem, that high kind of fades after a certain amount of time, and then I get kind of bored with the problem. And I’ve realized that it needs to be something more than that, that there’s been a handful of times where I was actually really passionate about the topic and I was really interested in the problem. There’s only been a handful of times where those both existed for the same project, usually it’s just the problem I’m interested in solving. One time was my thesis project, which was an education platform that was trying to harness a lot of these game mechanics and find a really creative way to build a better online learning experience. I was really passionate about that topic in education and I was really excited about the problem I was solving. I tried to start that business out of school and realized that going 6 figures into debt of grad school loans and living in an expensive city like New York and not coming from a wealthy family to back my venture, was actually a really difficult time to try and start it. I still have that idea kind of logged away and maybe when my stock at some startup goes big, I can try and invest in that. But the only other time is now here at Airbnb where I feel like I’m really passionate about communities, I’m really passionate about people traveling and I feel like it’s a brand that’s really tried to open itself up to being a champion of those kinds of ideas, and so I think I’m excited now that I feel like I’ve finally perfected that balancing that passion about what a topic is and interest in the problem that’s solving too.

How do your friends and family from home feel about how far you’ve come and the work that you’re doing? Are they like, “it’s a website. Do people work on that?”

[laughter] Yeah, none of my family knew what Airbnb was, which blew my mind because I expected it from my parents a little bit, but even my siblings who are my age had actually never heard of it, which surprised me. Yeah, it’s interesting. I think I’m the only person in my family to have gone straight into college and I’m the only person to have a graduate degree at all. And I think compared to my parents, I’m far more career-oriented than they were. They got married when my mom was—they went to my mom’s senior prom and I think he proposed that night and they got married months afterwards or something like that. So they went headlong into—they’re from Ohio, so like in the Midwest, I think that was more a thing—and they went headlong into family building right off the bat and that was their focus. And they didn’t really finish school. My dad eventually went back and finished. So it’s just funny because I feel a little bit like the black sheep in the family because their priority isn’t career things. They just don’t make as big of a deal about things that I tend to be really excited about when it comes to my career. I think my dad is a little bit more vocal about my career accomplishments. He’s definitely very proud. I think my mom’s side is very conservative and religious and I think they’re still [laughter] freaking out about the gay thing.

“I feel a little bit like the black sheep in the family because their priority isn’t career things. They just don’t make as big of a deal about things that I tend to be really excited about when it comes to my career.”

Outside of family, where do you find your support networks?

Close friends. I think I have a best friend that, he and I, we got randomly assigned as roommates in college. And were totally different people. We were just like opposites, really. Like, he was kind of this loud, crass hippy kind of guy. He was Buddhist at the time and exploring philosophy and I come from this very conservative family, so I was much more straight laced American Eagle wearing kind of guy. And then we totally brought each other to the middle ground, and both were very smart and challenged each other in conversations in college, and pushed each other .We have such a good friendship. It’s not a competitive thing, but it’s competitive enough that we push each other. And I have a couple of friends who are like that, and I feel like that’s where I find the most support – is having like-minded friends who just– not in an ego-driven way but just in like a genuinely ambitious passionate about certain ideas and pursue it. I think I’m naturally attracted to those kinds of people as friends and I think it just becomes a cycle where I seek them out and then they just push that certain behavior in me, and it just keeps going.

Yeah. Do you have any of those people here?

Not yet. No, I do. I have one. I have a good friend Kelly who I met when I worked at IBM, who happened to move out here. And so I have one close friend like that here. Mostly I’m getting to a point where—and I still keep in close contact, so my best friend I still talk to every day, either via text or online throughout the day. So I keep close to those kinds of friends no matter what city I’m in. I think I’m also getting to a point where, just because I’ve kind of reached enough momentum that I know where I’m going, and I’ve found that Airbnb as a company in general has actually been a pretty good support network, more so than any place before. There’s the sitting down with me asking me about professional goals, asking about life goals that have nothing to do with the company, but are things like, “Do you want to write a book someday? Let’s talk about how we could make that happen.” That benefits them in some ways, but it’s clear that’s not the main reason they do that. But it does make me feel so much happier working there, knowing that there’s so many other positives that are going to happen here. So I feel like in many ways my job more than ever before has become more of a support network too.

That’s really cool actually. It’s a kind of counselling.

Yeah, and I feel like I’ve definitely had jobs where they’re like, “Where do you see yourself with the company? Let’s work on…” And that’s fine—

As long as you work here.

Yeah, exactly. There’s a genuine visioning here about like, “Let’s talk about your career and what you want to be someday.” Which is really great to have those kinds of partners working around you, helping you find ways to get better, which you do. in a genuine way.

What do you think about the state of tech in 2016? What is exciting to you, what is frustrating to you?

I’m terrified it’s a bubble [laughter]. I talk about this a lot with my friends that, especially if you graduated into the recession, where after years of getting the best GPA you could, and all of the internships that you could have got, and the most practical major, and giving up all these cool other extracurriculars you thought you were interested in, you walked out into a job market that just had nothing for you. And I spent probably at least eight months without a job, which isn’t even as bad as other people, but was terrifying, and was, as someone who really always tried to be ambitious about the things they were doing with their lives, that was a really dark period. And so it haunts you.

“I’m terrified it’s a bubble [laughter]. I talk about this a lot with my friends that, especially if you graduated into the recession, where after years of getting the best GPA you could, and all of the internships that you could have got, and the most practical major, and giving up all these cool other extracurriculars you thought you were interested in, you walked out into a job market that just had nothing for you. And I spent probably at least eight months without a job, which isn’t even as bad as other people, but was terrifying, and was, as someone who really always tried to be ambitious about the things they were doing with their lives, that was a really dark period. And so it haunts you.”

Even after things started to get better, even after I started to get a footing in the workplace, I think I still carry this terrible ghost around that as great as this is, it feels a little like the 1920s of like—especially working in tech, in Silicon Valley, where there’s such excess, you can’t help but even in the best of days, when you’re getting spoiled rotten with some kind of amazing outdoor activity, or some kind of perk, be thinking like, “Man, this is too good to be true. This might not be around forever.” Which is such a negative terrible opinion so I worry that tech has this little bit of naivete right now where it’s enjoying so much success that it’s not thinking—it’s not worried that this might not last forever, or how it might be doing things differently to think about scalability long term as an industry. So, those are the things that I worry about.

“In Silicon Valley, where there’s such excess, you can’t help but even in the best of days, when you’re getting spoiled rotten with some kind of amazing outdoor activity, or some kind of perk, be thinking like, “Man, this is too good to be true. This might not be around forever.” Which is such a negative terrible opinion so I worry that tech has this little bit of naivete right now where it’s enjoying so much success that it’s not thinking—it’s not worried that this might not last forever, or how it might be doing things differently to think about scalability long term as an industry.”

That said, it’s also a time where there is still money flowing, there are still VCs funding great ideas, and I think it’s exciting to see—feel like you’re in the midst of something that’s on a scale like the industrial revolution, and you’re in the heart of it, and you’re meeting the people that are likely to be remembered as being great figures at this particular period. So yeah, there’s also this kind of historical aspect of like, “This is cool, I feel like I’m in the middle of this as it’s happening.” I’m in meetings where I’m suggesting ideas that impact a product that will come to shape a certain aspect of this new economy. Yeah, so there are days where you can marvel too that you’re getting to participate.

“It’s also a time where there is still money flowing, there are still VCs funding great ideas, and I think it’s exciting to see—feel like you’re in the midst of something that’s on a scale like the industrial revolution, and you’re in the heart of it, and you’re meeting the people that are likely to be remembered as being great figures at this particular period.”

I also feel like I should talk about the shame. Coworkers of mine living in The Mission have told me they hide the company logos on their bags during their walks home. They’re proud of where they work and what they’re building, but they have to live a different life going home or going out in parts of San Francisco. I, personally, have had dates preach at me on how the tech scene is ‘ruining everything about San Francisco’ while I silently pick at my food. Not long ago, there was a sign posted in The Mission that read, “If you work for any of the following companies: Google, Airbnb, Facebook, Uber, Twitter… [the list went on]. Then GET THE FUCK OUT OF OUR NEIGHBORHOOD.”

This is a confusing sentiment to me.

“I also feel like I should talk about the shame. Coworkers of mine living in The Mission have told me they hide the company logos on their bags during their walks home. They’re proud of where they work and what they’re building, but they have to live a different life going home or going out in parts of San Francisco. I, personally, have had dates preach at me on how the tech scene is ‘ruining everything about San Francisco’ while I silently pick at my food.”

I come from the Rust Belt. I’ve seen what happens when an industry “gets the fuck out.” It ain’t pretty. Communities disband. Generations of people suffer from unemployment, poor education, depression. Stigmas of failure soak into you. And eventually, bulldozers tearing down whole neighborhoods you remember. I understand the need to grow San Francisco responsibly and with respect to the character of neighborhoods. But this disdain for tech, instead of a desire to use it (and its taxes) for good, is baffling to me.

What would you—within the context of designing to solve problems—like to see more of in this space, in terms of design?

I hear a lot of people talk about how they don’t want to see people make more music apps or more food apps or something like that, and they want to see people like solve real problems. I don’t disagree with it, I just don’t find that I’ve encountered as many people as they have apparently who are building those kinds of apps.

“I think there’s a naivety of people saying, “I want to save the world with design.” I think I’ve seen a lot of people make posters and t-shirts and say that they’re saving the world with design.”

I think there’s a naivety of people saying, “I want to save the world with design.” I think I’ve seen a lot of people make posters and t-shirts and say that they’re saving the world with design. Milton Glaser said something that always stuck with me. He said, “You have to be really smart to be a designer.” I feel like that doesn’t ever get evaluated, not in design schools and maybe not even enough in hiring processes for some jobs. No one’s concerned about a designer’s intellectual interest or their intellectual stamina for hard problems and I feel like as an industry, it would be great that if design and designers were forced to have more of those deeper thoughts. You’ll do a portfolio review or you’ll do a quick problem-solving session where you try and design for someone in an interview, but rarely are you asked a deep question or a hard problem or even a logic problem. I’m just throwing out examples because maybe those are all silly ways to evaluate true intelligence, but some equivalent that really just gets to the heart of, “Is this person good at thinking deeply about the problem they’re solving?” It’s not just designers that have that problem, but designers when they can combine solid thinking with all of the other amazing skill sets they have they really form a power more than others expect of them. So I wish we were doing a little more thinking I guess.

Yeah. I feel you. On that note, what would you like to see taught more to young designers that you see in the industry? It might be the same answer.

A little bit. It’s hard to teach thinking.

These are great questions. I feel like my mentors would have really profound insights. I think I’m still kind of grasping at straws to try to solve them.

So I teach all the time to designers, and I try to find ways to make them care about what past designers have said. I feel like, especially places where I teach, like General Assembly, which is a very career focused, very tangible like, ”How does this relate to my job?” kind of questions you get from students. I worry sometimes that we’re losing like the academic side of things or we’re losing something like spiritual side of design education. Like the Eames have these amazing design perspectives. I’ve been relying on them pretty heavy actually in the last few classes more so than other design figures. Because they were so great at talking about other things that I think designers should be paying more attention to. About innovating on your designs, about having this attitude of serious play, an interest in how design plays a role in education, etc. Because so much of what we do in terms of communication are also education. I wish there was more attention paid to our old heroes and a greater appreciation amongst digital designers for some of those legacies because there’s still so many lessons to learn from them. It’s not just about what the latest shortcut in Sketch is or how to work best in agile development flows. There should be an appreciation for our longer history and the way that that context is still very relevant, how all those patterns still repeat even in the kinds of mediums we work today.

Yeah. This is a very nourishing conversation for me.

I have problems going to even—I’ve stopped actually, I’ve stopped going altogether to design talks. There’s so many of them, and I feel weird about it because even though Airbnb and lots of companies offer a design education budget where you can go pick a talk that you want to go listen to or a conference. I’m just fatigued with them. I don’t like the forced awkward social interactions of going to this place, like, “You have the same job as me. We must have reasons to talk,” or I don’t know. Hearing people talk about a topic and I’m like, “You don’t know any more about this than I do. We are all still figuring this out.” And I feel like the best things I’ve ever heard are things like UX book clubs, where you go deep dive on a topic. There are more branching connections. Maybe I really am a generalist. And then there’s a discussion about it where you’re learning from other people, but there’s a core topic to focus on. Whenever it’s these open-ended talks, I’m just either bored or just starting to get frustrated with them. But I think maybe that’s part of it. Again, it’s still so specialized. It’s a very specific aspect of design. And I would much rather someone start with, “How’s a banana like Napoleonic battle plan?” And then have some really interesting connection between those seemingly disparate things.

So, how is a banana like a Napoleonic battle plan? Jk. What are you working on right now, either for work or for yourself? What’s 2016 goals?

I actually have a lot more travel goals. Like life experience goals. The west coast is all new to me. So this weekend’s my first trip to Seattle, and I’m going to do a road trip with my friend. And I’ve never been in LA, and I went to Las Vegas once but I was sick the whole time, so I didn’t really go. And I want to see Portland. There’s a lot of travel that I’m going to do over here that’s kind of preoccupying me, but—

You’re going to love exploring the west coast.

It’s so much more scenic than the east coast. Like, I love the east coast but it’s also like home to me. I’ve seen it a thousand times with driving up and down it all the time, so this is all brand new and it’s really exciting.

The first time I ever drove up and down Highway One, I was just like, “Now that I know it exists I can’t not live here.” And I moved here like two months later. And California still feels a little out of grasp as far as permanence, but it’s very much like now that I know it’s here I can’t not be in it.

Yeah. I can totally see that happening to me. I just did like a little taste of it up in Marin County with The Redwoods and stuff like that and was blown away. Just totally way bigger, better than I thought it was even in pictures. So, yeah, I’m sure as I continue to explore I’m going to find myself conflicted. I don’t think I’ll go back to the east coast as easily as I always thought I would some day.

Well, that was my next question. Where do you see yourself in five or ten years? Do you think you’re going to go back?

This was the question that made me move here, actually. So I was talking with a friend. She does a podcast, actually, on LGBT people in tech.

Cool.

I should point you to it.

I would like to meet her.

She’s great. So she was doing this interview series—we went to graduate school together, so she was kind of doing friends first, and so she did me as her first test subject through this—and she asked that question, and at the time she asked it I was like, “That’s kind of a cliche question.” And then I thought more about it, and I told her, “I don’t know. I guess in five years I see myself hopefully—I can really answer more specifically—it’s hard to answer about what I’ll be working on.” Because at the time when I was asked this over the summer I was working on mobile ads, which is—I think that did not exist five years ago. And now I work for Airbnb on aspects of the sharing economy that didn’t exist five years ago. When you work in this industry you just know that,”I have no idea what I’m going to be working on in five years. Maybe it’ll be self-driving cars or something.” But I did have some ideas about where I saw myself going personally, and it was about finally meeting someone and settling down and all that sort of thing. And after I had that talk with her, I realized, “Shit, if I’m going to settle down in the next five years, then the next five years are kind of—not my last time to do anything single, but I should certainly think a little bit about what would be really hard to do after I settle down, and probably moving across the country is one of them.” And so I Iooked back at the shortlist of cities I wanted to live in, and I was like, “I should probably—” I really love New York and I’m really comfortable here and I actually didn’t see myself leaving any sometime soon, but maybe I should hold off on settling down because I should still stay open to it. Not but two weeks later, Airbnb’s recruiter called me up and was like, “Hey, are you interested in a job?” I was like, “I’m not.” But I feel like after that conversation I should keep doors open if something on the West Coast is calling. Sure enough, everything unfolded and six weeks later after that conversation with my friend, I was packing up and moving across the country.

Wow.

That’s a scary question to me now because [chuckles] my whole life turns on a dime when I try to answer that one. But yeah, I don’t think it’s changed much since the summer. My answer is more or less the same but now I’m over here. I think it’s been good keeping my mind open of if I would like to settle down a little bit in five years then I really need to keep prodding myself to not get lazy in terms of keep my mental plasticity fresh, and keep trying to solve new problems, and keep trying to stay open to new cultures, and embrace the West Coast and it’s hippie weird shit, and learn about it and get to know people who are into it. Because if I rest too easy and just surround myself with the same New Yorkers, I feel like I’m missing the point of these next few years where it’s easier to do all these open things as a single person.

I will say after almost seven years here, I feel right in the middle. I’m definitely East Coast in a lot of ways. I definitely have the New York hard ass-ness to me. I’m part redneck, so there are things about the south that I definitely appreciate. But I feel like I’m half west coast now, and it’s really—like you can either view that as you don’t fit in anywhere or it’s just kind of lovely to just kind of know what the best parts are and just soak them in. It’s fun being a hybrid that works her ass off but also sleeps a lot, and is easygoing but also super alpha. It’s fun to kind of glean the positives from all of the places that you’ve lived and just end up being a mutt.

Maybe you feel the same way I do, but when people ask where I’m from I find I change my answer depending on where I know they’re from. So if someone’s from like Indiana then I’ll say I’m from Ohio, which is really where I was born.

I was born in Indiana.

But if someone’s from the south then I’m more likely to say, “Oh, yeah, well, I went to high school in Florida,” which I did spend roughly half my life in Florida so it’s technically true. But other times ask, from San Francisco, “Where are you from”, and I say, “Oh, I just moved here from New York.” Being from all these different places, I find that I kind of like do this chameleon thing where I play to my strengths, basically, of all the best possible places I’ve lived.

Yeah. That makes sense to me completely. This is such an extreme example, but I had to photograph George W. this year, and in my mind I was like, “If he knows I’m from San Francisco this is going to go horribly.” So he was like, “Where are you from?” and I was like, “North Carolina,” with my old southern accent.

There you go. I would totally do that. I would be totally like, “Oh, I lived in Austin for a while. I loved Texas.”

Yeah, like, “How can I be as Southern as possible so that you will cooperate with me?”

[laughter]

Let’s see. I actually think I already asked you this, but let’s just dig in again. What advice would you have for folks just getting started in the industry? What do you wish you had known in the beginning?

I think I walked into it with a lot of—I actually had some really negative influences when I first started designing, I remember. People who made me feel really inferior because I didn’t know about design, and I didn’t have a formal background in design so I didn’t know all these design heroes, who I later got to meet and work with—talk about a rags to riches kind of thing—but a lot of people made me feel bad about that. A lot of people were very pretentious in the design world. I knew the tools; I knew how to use Photoshop, I knew how to do some of the stuff, I had an intuition about how to make some things, but I didn’t know a lot of the principles. So there was a lot I had to learn. I know a lot people who, unfortunately, didn’t encourage me, but just made me feel like there’s just too much for you to learn for you to try and get into this on your own.

“I actually had some really negative influences when I first started designing, I remember. People who made me feel really inferior because I didn’t know about design, and I didn’t have a formal background in design so I didn’t know all these design heroes, who I later got to meet and work with—talk about a rags to riches kind of thing—but a lot of people made me feel bad about that.”

So, I would say to someone who is interested in design to try it anyway, and go for it. In fact, I think there is an innocence before you actually learn all your principles about design, that is something you should just kind of enjoy while you have it. There’s just kind of a freedom of playing. I don’t know, maybe that’s not true. Maybe the principles actually free you to experiment better. But, sometimes I worry I play it too safe now that I know more of the rules, quote unquote. There’s just that nice moment where you’re starting to get interested in design that people should really hold onto and embrace.

“I think there is an innocence before you actually learn all your principles about design, that is something you should just kind of enjoy while you have it. There’s just kind of a freedom of playing.”

It takes a long time. I think people should know that, too. I’ve been doing design for about ten years now, and I think some people don’t realize how long it takes to get where you want to be. My step-brother, for example, did acting in college. And now he’s kind of reached this point—where I feel a lot of actors do—where he’s been doing it, trying to do it for a few years. And he’s kind of like, “Alright, this isn’t going to happen. I need to look at something else.” So, he’s looked at design a few times. Some of his friends have looked at design. But I think there’s this kind of assumption like, “Oh yeah, I’ll learn Photoshop. You’ll give me some tips, and then I’ll be like working at Conde Nast next year,” or something like that. I have to remind him that it took like five—no, how long ago was that? Maybe six or seven years ago, I couldn’t even get a Tampa ad agency to hire me as an entry-level designer. It took a long time of building up a career—of some dumb luck, of building up a portfolio—before I finally got into bigger positions that really started to let me influence bigger and bigger projects, and have a lot of fun with it, in the way that I like to have fun with it. So, I would encourage people who are getting started to be patient, to understand that just because you can easily access a copy of Sketch or Photoshop doesn’t mean that you’re going to be an overnight success. If there’s ever anyone in your life who’s telling you that you shouldn’t bother doing that, that you should just keep pushing through it. Because hopefully there’s– eventually some better influences around you who will help out. And if you don’t have any of them, then you should go to General Assembly and I will help you [laughter].

“Maybe six or seven years ago, I couldn’t even get a Tampa ad agency to hire me as an entry-level designer. It took a long time of building up a career—of some dumb luck, of building up a portfolio—before I finally got into bigger positions that really started to let me influence bigger and bigger projects, and have a lot of fun with it, in the way that I like to have fun with it.”