I’m from Colorado. I grew up in Colorado Springs.

My mom is a doctor and a single mom. How do I describe my upbringing? Colorado Springs is famous for like “Focus on the Family” and super conservative Christians. But I wasn’t exposed to any of that, I just had my mom, her medical practice, and all her doctor friends. The problem with this question is that I got poisoned as a child, so I don’t remember anything from before probably thirteen. I have forgotten most of my life actually, I found out recently my husband and I had a wedding that I don’t remember. There are pictures and everything.

Holy shit.

So my whole childhood is basically gone. My mom remembers, you can ask her if you want [laugh]. The primary answer to that question is I don’t know, because it’s gone, all that stuff is just gone. I know I have two brothers and a sister, but I don’t have a lot of anecdotal things from childhood, or even more recently, because it’s just not in my brain anymore. My memory, if you can call it that, is stored entirely in a combination of other people and various kinds of recordings.

“I got poisoned as a child, so I don’t remember anything from before probably thirteen. I have forgotten most of my life actually, I found out recently my husband and I had a wedding that I don’t remember. There are pictures and everything.”

So, if you feel comfortable, what happened?

On my tenth birthday, my family­­ so my mom and my little brother, me and then I think two friends, I don’t know, some small group of people went to a hotel that had a pool to do ten-year-old birthday things.

And the hotel was negligent on their maintenance or something, I don’t remember. There was a lawsuit, I never read the findings, I was too young. So they were negligent and carbon monoxide and chlorine gas and some other gases leaked into the pool area, and my mom and my little brother and me and both my friends were poisoned. But my mom and I got the worst effects, we were poisoned the most. So, my mom and I went from being totally normal to having traumatic brain injuries, but by poison instead of war or football or whatever.

How did those injuries manifest in the early years, and how is it continuing to?

It has changed over the years. Gotten better and worse. I get attacks of uncontrollable shaking. My body is usually in pain. I get a ton of migraines, a fuck ton actually. My proprioception, which is like, the accurate sensation of where your body is in space, and the position you’re in is 80 percent gone which means my balance and walking have good and bad days. I am basically a grab bag of neurological issues: Alice in Wonderland Syndrome to Post-­traumatic Stress Disorder. It’s hard.

I seemed to improve slowly until I was in college, but then when my brain was under stress I got a bad relapse. So I guess my junior year in college I was all way back at the bottom. I couldn’t walk, I was having migraines everyday, I shook constantly. After that I was really bad for several years and I’ve been inching my way back out of that hole ever since.

What about your mom?

My mom, you would describe her as like a stroke victim. Even though that’s not what happened, that’s a thing people understand. She basically got a migraine for 8 years straight. She is doing much better now. Still dealing but better.

Wow. So you probably don’t remember but, as a kid, what did you want to be when you grew up­­?

My mom says I wanted to be a surgeon, which I am now like, “That is the most ridiculous thing I could have ever thought of.” But, of course that’s what I wanted to do. My mom was a doctor and her medical practice was very integrated into our lives so of course I wanted to do medicine. I think my initial “I’m going to college” was pre­-med, until I figured out about chemistry. I was like, “ugh, this is horrible.” Chemistry is the worst. Or at least that’s what I like to tell myself. That I had a choice, that I opted out instead of what really happened which is that I was forced out by my disability.

Did you have any idea at that time that you’d end up in Silicon Valley tech?

No. My BFA is in Theater, Film, and Television Production, so I thought I was going to go into Theater. But I got so sick at the end of school that all of my best laid plans were totally ruined. I was supposed to go work as an assistant stage manager in Tokyo. But I was too sick, there was no way I could take that job, or any job.

So walk me through the winding road that took you to VR.

So after college I was essentially on bed­rest for four years. I shouldn’t say bed­rest. I was home­bound for four years. Walking to the bathroom made me dizzy so I crawled kinda thing. So in that time, I started watching Art21, which is this contemporary art show made by PBS. It’s so fucking good. It’s a collection of artists talking about their work and their lives and their families and it changed my life.

I was laying there on the couch at 20 thinking that this painful bullshit was what the rest of my life was going to be like, and I decided, “Fuck it I’m gonna steal ideas from these people.” So I starting copying their work. Andrea Zittel and Ann Hamilton and Vija Celmins and Kara Walker. These women became my pantheon. Oh and Janine Antoni, Janine Antoni! She’s amazing! She’s from the Bahamas and she would place a tightrope right at the horizon and then she would walk across the tightrope on video and every time she took a step the line would just touch the horizon. So good. She also hand spun this huge rope with all these video tapes and clothes and just any material donated from her friends and family. Antoni made a rope so I made a rope. Zittel crocheted so I crocheted. Hamilton talked about social concepts in cloth so I talked about computational concepts in cloth.

I copied lots of work from Art21 because there was nothing else to do. It was just not what you want to happen right after you get out of college. Like, “I’m going to get an internship, and I’ll be out every night and­­—No. You’re going to lay in bed for four years and be bored.” That was basically the start of like, “I am an artist now.” The art was my entire life at that point, I guess it still is.

When I finally made my own work it was these brightly­-colored abstract crocheted sculptures the size of, ironically, the couch I’d been stuck on. I guess the first time I really showed anything was in 2009, with the Armory Show in New York.

“I was told my thesis work wasn’t art because I made a video game. It wasn’t even a game it was an interactive environment that addressed the contemporary way that we go about knowledge formation. They couldn’t see it. It was weird because I was interested in technology. The work that I was making before, the crochet, was about reenacting computational systems. But they had never seen that either, those works were talked about as “heroic women’s work”. It drove me crazy. The professors never could see crochet as data, as captured information in the shape of a linear thread. But I still graduated, so fuck them.”

*Just* the Armory? [laughter]

Yeah me and galleries have never been much of a thing. Then I used that work, and the credential of that show to apply to grad school. I went to the California College of the Arts over on Potrero Hill. That was the first time I was really out of the house everyday by myself in years. I was 24.

Some of it was great. I found a couple professors that were awesome.

It should come as no surprise that I did not fit in well at school. I had just spent 4 years alone with the exception of my boyfriend. I didn’t know how to human and I was learning to be disabled not just at home in a bubble of my own control but at the school, in classes, on the train etc. Once again I have very few anecdotes of grad school, what with my memory but I know it was both great and really stupid. I got really tough and focused because of school. I am a much better artist now, and I found one professor who I am friends with today who is brilliant and funny and really important to me. But because I wasn’t great at interacting with the other students, so they started calling me The Borg. They were like, “But it’s endearing because we like you,” and I’m like, “No, it’s socially separating and bullying.” But they never stopped.

I was told my thesis work wasn’t art because I made a video game. It wasn’t even a game it was an interactive environment that addressed the contemporary way that we go about knowledge formation. They couldn’t see it. It was weird because I was interested in technology. The work that I was making before, the crochet, was about reenacting computational systems. But they had never seen that either, those works were talked about as “heroic women’s work”. It drove me crazy. The professors never could see crochet as data, as captured information in the shape of a linear thread. But I still graduated, so fuck them.

So what happened after that? I got my first job. I was so proud of myself. I worked as an architectural assistant making drawings and writing their blog. I worked there until she couldn’t afford to pay me anymore. Then I started working for Axis dance company and they’re in Oakland and they’re physically integrated dance company and I worked there for almost two years, man, what I thought at the time was going to be a dream job turned out to be awful. Anyway I also wrote for KQED in there, writing about net art, the internet, and video games mostly, and I was doing a lot of both digital drawing and ink on paper which both turned into making gifs and prints and comic books. It was around that time, in 2013, I started making YouTube videos too. Again copying existing work I liked from Mike Rugnetta and PBS Idea Channel. Huh, twice now PBS has been foundational to my art.

The videos started as talking head style technology and cultural criticism pieces plastered with wild editing. It was a great way to restart with video. I had experience editing short films and features from college but the show, self-titled BlinkPopShift, also leaned hard on the writing and research skills I forged at grad school and KQED. It became a way to think across tech and culture and art and science the same way I had been exploring in my masters thesis, but now everyone, not just the limited pov’s of my professors, could see the result. Simultaneously I built a whole body of work exclusively on my phone, the Still Lives series, using a combination of photogrammetry and various gif making apps.

I became super immersed in Youtube so I went to Vidcon and met Mike Rugnetta and Vi Hart and Malia Moss who all turned out to amazing friends and collaborators. A few months later I got a call from Vi asking “Hey, do you think you could build a VR camera?” And I was like, “Yeah sure, I don’t see why not. That doesn’t seem that hard.” And I was right, I mean it took months of work and cameras melting and trial and error and math but I did it.

“A few months later I got a call from Vi asking “Hey, do you think you could build a VR camera?” And I was like, “Yeah sure, I don’t see why not. That doesn’t seem that hard.” And I was right, I mean it took months of work and cameras melting and trial and error and math but I did it.”

So you just… made a VR camera?

I mean, yeah. We, along with Andrea Hawksley, the three horsemen of eleVR, have been working on various projects in VR, AR, and mixed reality every since. Vi’d hired me to work at the then Communications Design Group, Alan Kay’s Research Lab at SAP. Working for an open lab is great because with no pressure to publish traditional papers, we can write up everything on our blog for anyone to read.

I have to say I was so happy when fully spherical, auto-stitching cameras came on the market and I didn’t have to actually build them by hand with a fucking hot glue gun anymore, which was fun but also so tedious. I focus on studying how immersion works and how aesthetic techniques communicate to viewers. Recently I’ve been building the foundation of spherical cinematography so I can use that knowledge when designing immersive web systems.

What excites you about that space?

Making hybrid reality projects where linkages are no longer limited to computers and screens. When I write or make art, I like to put stuff everywhere but computers in their current conception don’t allow for creative messes. Sure, you can barf icons all over your desktop, but that’s not a creative mess. It feels heavy and in need of “organization.” Good messes feed my creativity through serendipity and flexibility. But my physical messes don’t have search for when I know exactly which bit of red paper has to go on the collage next. That divide between the physical and the digital will close, ‘cause me and my vice grip say so.

But that also means taking seriously the considerations of what the body wants. Because like, we are not fingers with eyes and ear holes. The way we do knowledge creation has a lot to do with this flappy meat thing. We completely disregard its wants and needs and its ideas about the world for what, a touch screen? This is the most embodied form of computational media that we have? Pinch and zoom and swipe and tap? Gross. There’s so much touch you can’t get in the little rectangles we carry around everywhere, it drives me crazy.

“When I write or make art, I like to put stuff everywhere but computers in their current conception don’t allow for creative messes. Sure, you can barf icons all over your desktop, but that’s not a creative mess. It feels heavy and in need of “organization.” Good messes feed my creativity through serendipity and flexibility. But my physical messes don’t have search for when I know exactly which bit of red paper has to go on the collage next. That divide between the physical and the digital will close, ‘cause me and my vice grip say so.”

What is it like straddling two worlds—art and tech—that often feel at odds with each other?

At work, I don’t feel at odds because like they specifically set up the lab for that kind of cross disciplinary flexibility. I am the most traditionally “visual art” person there, which I find funny since in grad school I was the most “tech” person, but being a weird inbetweener is kinda our thing at the lab. But when I’m out of my bubble it’s really hard because my work, and probably my personality too, is hard to parse as either or, as art or tech, as artist or researcher. A good example is that I don’t go to VR meetups any more. Everyone was too newness focused. There was no bubbling curiosity, no juicy conversation. It was just, sorry to say it but, a bunch of white dudes being boring. Ugh, tech Industry problems.

What are the biggest motivators behind your work?

I make art for two people, which people do not like to hear, but it’s true. I make sculpture for Steve Sedlmayr, my husband, who is such a fucking treasure, we’re 12 years this summer, and I make video for Vi Hart, who is one of my best friends and my boss. That’s it. The sculptural work is for him and the video work is for her. When I can make either of them tilt their head or think “What is that?” or smile or laugh or say “Yes. More please,” that’s winning.

There is definitely a subtle pressure from social media to care about a bigger audience and I do have a small audience online. Some people watch the videos online, and some people read the stuff that I publish, and that’s great but I don’t crave their opinions. For me, seeing Vi watch a video and afterward be like, “Damn!” That’s my chocolate sundae.

“I am the most traditionally “visual art” person there, which I find funny since in grad school I was the most “tech” person, but being a weird inbetweener is kinda our thing at the lab. But when I’m out of my bubble it’s really hard because my work, and probably my personality too, is hard to parse as either or, as art or tech, as artist or researcher. A good example is that I don’t go to VR meetups any more. Everyone was too newness focused. There was no bubbling curiosity, no juicy conversation. It was just, sorry to say it but, a bunch of white dudes being boring.”

I think it’s like you’ve miraculously managed to achieve something that I’m just starting to achieve—the “art of giving no fucks.”

I think it’s absolutely pivotal—or giving exactly the right fucks. You’re going to give a fuck about someone’s opinion, but just give it to exactly the right ones. My husband, he is also an artist. He makes games now but he knows a lot about sculpture and is really interested in sculpture. Making a sculpture for him is so powerful and awesome and his feedback really pushes me. Don’t give no fucks, just give the right ones.

I love it. What are your thoughts on the state of tech in 2016, both the tech that you considered tech and the tech that a lot of people consider tech?

Tech is so confusing. What even is the technology industry? Are search engines and camera manufacturers and Crispr therapies and video games really in the same industry? I feel like we use “the tech industry” the same way people used to “big business.” What is that thing I hear over and over about Uber? “Uber is a taxi company, not a tech company.” Bakers with online delivery are still bakers. Podcasters with an app are still in the business of podcasting. Tech is just a lazy over simplification of the Bay Area’s $785.5 billion economy that makes it all the more frustrating for people like me to take my work out into the world. I’m not an academic and I don’t make a product… I make art to do research.

Condensing all these different companies into a thing we call the tech industry does gives us something to blame for the city’s problems. The industry is refusing to act as proactive stewards of the place where their employees live. It seems like a lot of money’s being made and not very many taxes are ending up in city coffers. There is clear evidence that private corporate bus lines do increase evictions near their bus stops. Rents are increasing along with poverty.

“Tech is so confusing. What even is the technology industry? Are search engines and camera manufacturers and Crispr therapies and video games really in the same industry? I feel like we use “the tech industry” the same way people used to “big business.” What is that thing I hear over and over about Uber? “Uber is a taxi company, not a tech company.” Bakers with online delivery are still bakers. Podcasters with an app are still in the business of podcasting. Tech is just a lazy over simplification of the Bay Area’s $785.5 billion economy that makes it all the more frustrating for people like me to take my work out into the world.”

Homelessness is intensifying as more people are flooding into the Bay Area chasing after those sweet, sweet jobs. Did you know 70% of the homeless population in San Francisco was housed in the last year? Along with all these changes fear mongering about the collapse of San Francisco’s weirdo based culture. Most people would say that I’m being naive, that corporations have no obligation to nurture the community in which they exist, but if you don’t do that—if you don’t support the community—then all you’re doing is going to Southeast Asia and cutting down the mangrove forests and planting palm trees so that you can get palm oil. There it looks like environmental destruction, here it looks like community destruction. We have to grow out of the self centered capitalism that disregards the larger systematic effects until disaster strikes. We have to take responsibility for that because we’re not heartless idiots who just stomp around the world with our big dumb America boots. I don’t want to be that kind of America.

Man. It is kind of wild to think that big tech is actually necessary for new innovation to survive long term.

Oh yeah, I totally agree but also like big tech is completely dependent on Chinese money, right? Like a lot of VC money comes from China and that’s fine. I’m not saying it shouldn’t come from China but if that’s going to be true, then you also need to take into consideration the health of the system of products and money and labor is there too. The whole system should be healthy, not just any individual part of it. Why is making as much money as possible still a thing? Who in their right mind is motivated by I want to make as much money as humanly possible. Why? It’s boring. Come on. Look I was raised by a woman who taught me that holistic world views were the only path to true equality, whether that’s in a body or a society, and I hold that as a core value to this day.

“We have to grow out of the self centered capitalism that disregards the larger systematic effects until disaster strikes. We have to take responsibility for that because we’re not heartless idiots who just stomp around the world with our big dumb America boots. I don’t want to be that kind of America.”

Total side note, but maybe possibly related, I remember reading that you have received death threats for speaking your mind.

Oh yeah [chuckles] yeah, that was a problem. My team and I went to the first Oculus Connect, and there was an open panel, and it was being live streamed on the internet. And they were like, ”Anyone could come up and ask a question.” And there was 1% women at this conference and very few people of color and there were no female speakers and I was mad. So I went up and asked how they planned to prevent the clear race and gender biases of their conference and the industry as a whole from doing to VR what sexism and racism has done to video games.

And they answered it really poorly. It was so lame. But since I am female and it was live streamed that question turned into doxing, and death threats on 4chan and Reddit. We had to get our corporate security officer to intervene. It was scary. I hadn’t expected such an infantile response. I felt so naive. I’m still super naive, because I still assume that everyone wants everyone to be equal. Also, people who do death threats are so uncreative. I felt like they were just copy and pasting from Anita Sarkeesian‘s death threats.

I’m curious, are you able to give no fucks about that or­­…?

I don’t care.

That’s good.

Yeah but I have the ability not to care because of my privilege. 1. I’m white and cisgender and 2. I work for a place that can provide corporate security. Privilege means the death threats are less meaningful to me.

“The whole system should be healthy, not just any individual part of it. Why is making as much money as possible still a thing? Who in their right mind is motivated by I want to make as much money as humanly possible. Why? It’s boring. Come on.”

How do you think tech could be more accommodating right now to a more diverse set of people?

I mean hire them? I love Ta­-Nehisi Coates’s phrase “People who believe themselves to be white…” so I would say people who believe themselves to be white should maybe consider people who do not believe themselves to be white. People always complain the lack of diversity is a pipeline issue which is such blame shifting horse shit. If you think of people like crude oil who can only reach your factory via a standardized and maintained pipeline then maybe you shouldn’t be a company. Or hire people who you perceive to be less qualified. Because your perceptions of someone’s lower qualifications are based on your own biases. Go around saying that you’re biased. Be like, ”Hello. I’m white, and I have white people bias.” No one is going to think that you’re a horrible, evil person by acknowledging the fact that you’re biased. Everybody is biased, just acknowledge it, and then build systems to make sure that it doesn’t affect the population of your company. Super simple things. When you have a varied population of employees, go to them and be like, ”Hi. How are we not helping you to do your best work? Please tell me? We are trying to do better.” Be a person with feelings and failings for fuck sake.

What advice would you have for someone who wants to do meaningful work in tech, but doesn’t know where to start?

Pretend like you can accomplish the thing that you want, and write about it as though it were an inevitability. Write about how the meaningful tech that you want to make is the most important thing in your whole life. Read those writings into a camera. Publishing all of it online. Repeat. Thinking publicly and meaningfully about what it means to use a computer, what it means to use your phone, what it means to use stuff that you want to exist in the future will not only hone your ideas but attract interested bees. Write up design documents for your fake thing. Make drawing of it. Research. Don’t make a product. Go to the library. Because that’s what I do. I don’t make a product. I don’t make technology, really. I make art. I think deeply about the stuff I make and I write about it in clear ways people can connect with.

“People always complain the lack of diversity is a pipeline issue which is such blame shifting horse shit. If you think of people like crude oil who can only reach your factory via a standardized and maintained pipeline then maybe you shouldn’t be a company. Or hire people who you perceive to be less qualified. Because your perceptions of someone’s lower qualifications are based on your own biases. Go around saying that you’re biased. Be like, ‘Hello. I’m white, and I have white people bias.’ No one is going to think that you’re a horrible, evil person by acknowledging the fact that you’re biased. Everybody is biased, just acknowledge it, and then build systems to make sure that it doesn’t affect the population of your company. Super simple things. When you have a varied population of employees, go to them and be like, ‘Hi. How are we not helping you to do your best work? Please tell me? We are trying to do better.’ Be a person with feelings and failings for fuck sake.”

I’m Canadian. I was born and raised in Ottawa, Ontario—the capital of Canada. I was born to a quite young, single, soon-to-be-lesbian mother (she came out when she was three months pregnant) who had just left home. She didn’t know what the heck she was doing but had me anyway. There were not a lot of lesbians having children in the 70s, those who had them were coming out of straight marriages and had to be careful not to get their kids taken away, so she was a rare bird and it meant I also didn’t know a lot of other kids that had queer parents. So, my early years were unique in that way.

“I was born to a quite young, single, soon-to-be-lesbian mother (she came out when she was three months pregnant) who had just left home. She didn’t know what the heck she was doing but had me anyway. There were not a lot of lesbians having children in the 70s, those who had them were coming out of straight marriages and had to be careful not to get their kids taken away, so she was a rare bird and it meant I also didn’t know a lot of other kids that had queer parents. So, my early years were unique in that way.”

My mom was also an activist, feminist, and non-traditional woman (might be read as butch but never identified as such). She drove a taxi, did woodworking and construction, she DJ’d queer and women’s dances, and she was very active in Ottawa socially and politically. She was a role model for doing all sorts of different jobs and not knowing how it will all add up later.

She was also strong in math and logical thinking and that’s something I’m grateful for.  We’d play games at the grocery store doing the math on which size of a product was the best deal for the money. This was fun for me and a necessity for her. She didn’t earn much money so we never had a lot of stuff as I was growing up. My grandparents were my primary source of school supplies, clothes, toys, and candy, not my mom. She was on social assistance or earning a very low income so I was never certain I was going to go to university. I earned good grades and figured there might be scholarships.

My first 3 years of high school I was trying to fast track—my plan was to go to Queens University and be a lawyer, because I liked to argue. I was fast-tracking to do high school in four years instead of five by just doing the required classes instead of any electives so that I could get out of there faster, both away from my mom but also I needed to get the heck out of the country high school I was going to. Instead, I ran away from home at 17 and my school track slowed down. I ended up splitting my last year of course work back into a two year spread so I was only half time and just managed to complete high school while on social assistance. I filled out the university applications like everyone else, because it was free to do from high school, but I didn’t know how to follow up with interviews for the programs I applied to (film and animation) and I had no idea about student loans so I didn’t get into any of my choices.

“We never had a lot of stuff as I was growing up. My grandparents were my primary source of school supplies, clothes, toys, and candy, not my mom. She was on social assistance or earning a very low income so I was never certain I was going to go to university.”

At 19 I moved to Montreal from Ottawa and got involved in the political activism there through the women’s center at Concordia University. There I also learned about student loans and I applied again to University the next year. I was trying to get into film animation. I had always really wanted to make animated films but I couldn’t get into that program because I’d never taken enough art to have a portfolio. It was kind of a bummer because it’s like “I’m going to pay you for this degree, can’t I learn?” I had been drawing and doing comics my whole life, but not with any kind of formal training.

I ended up going into Women’s Studies because that’s what accepted me and I did a year and half of Women’s Studies. Then I dropped out when it got hard because I didn’t actually have any study skills. I did really well in high school without having to try very hard and suddenly, in university, I didn’t—I reached the limits of what I knew how to do off the top of my head. So I freaked out and dropped out and spent the next 10 years doing minimum wage jobs and evading loan collectors. That’s the early years.

At that point, I’m assuming you had absolutely no idea you’d be in Silicon Valley?

Oh my god no! I didn’t have any idea I’d be in Silicon Valley—didn’t even really think about its existence. I first was introduced to it in 2008 when I came out here to do an internship at Mozilla, which was across the road from the Google Mountain View campus.

I went back to school in 2005. I was turning 30. I was like, I need a job where I can get my teeth fixed. I figured I’d go punch a clock at IBM or something and have a decent middle-class income. And probably still live in Toronto, which is where I lived and went to school.

Discovering Open Source, getting involved with Mozilla, and then coming out here with a high-paying internship and being a part of the tech boom happening here—it’s nothing I could have imagined. I tried to move to San Francisco in 1997 as a young, broke queer. I worked under the table at a cafe and made $100 a week, which was barely enough to eat a Snickers bar for dinner and take the bus to work the next day. I didn’t know how to be an illegal alien here, had no safety net, and was not making enough money. At that same time a lot of my friends were being evicted, because of the first dotcom boom, and people were losing their housing, and moving further and further away from Mission/Valencia area. I was here for three or four weeks, and then had to go back to Canada, and go back to my own minimum wage jobs there. So I always wanted to come back and try again.

When the Mozilla job offer came through, I realized Mozilla would pay for me to move, and take care of my work visa, and I’d have health care. It felt like I had a red carpet rolled out for me returning. But I got back here to something akin to a funeral, for what San Francisco was. And again, people are being evicted, and there’s all this loss of radical queer & artists community. Then the housing market crashed. Everyone except for people in my industry was feeling it. At my job, we were still getting yearly raises.

“I went back to school in 2005. I was turning 30. I was like, I need a job where I can get my teeth fixed. I figured I’d go punch a clock at IBM or something and have a decent middle-class income.”

Wow. How jarring was it for you going from—I saw when I was stalking you online that six years ago you were making less than 10k a year, you grew up in poverty—and now you’re living a different life?

There’s an interesting trajectory there. I was very much—and my mom was like this too, spend everything you’ve got. You get a check and you spend it. In some ways, I was always very comforted by not having any money, because then I couldn’t sabotage it or mess it up. It was like, ‘I’ve spent all the money I’m going to spend, I have whatever groceries that are in my fridge, I have my bus pass in my pocket, I have my carton of cigarettes’ (when I smoked). I just took care of the things that were essential and then that was it. There was nothing else to worry about. I knew where to get free food. There is a certain ease to being broke when all your friends are also broke.  Everything we did for fun was free or super cheap.

I got a job offer at the end of my internship. I had been getting paid $5,000 a month to be an intern and I was saving it up to pay for the last year of school (eating 15 free meals a week at Google was instrumental in saving $), and I got a job offer of $60,000 for my first year out of school. To know that I was going back to school to finish up eight months and then to have a job right after, that paid so well, blew my mind. My mom was at the top level of her current career in government. She was—I should have mentioned this, she went back to school as soon as I left home at seventeen and she got a bachelor’s and a master’s really quick and then worked herself back into a middle class financial situation. She had grown up middle class. She got herself back into that and her partner, who she’s been with for 30 years now, comes from a  middle class background—two parents who are both PhD English professors, so they have a very comfortable life. They’re very thoughtful and conscious people who get to live very well. They don’t live extravagantly or anything, but they also make good money. And my mom, I think, has managed to probably catch up for all those years of struggling financially.  She’s supposed to retire in the next couple of years and I’m watching how that works out for her since she’s my main role model.

I observed her doing that, I observed another person who did that—going back to school then shooting up into a middle class job after not having money—and that was why I went back to school for a bachelor’s degree. I was also thinking “I’m doing it eight years earlier than my mom, so maybe I get eight years of advantage.” And I really did. I came out of the four year degree with a $60,000 job offer. My mom was making $92,000 at her top level government job. So I thought “Wow, I really am fast-tracking.”

“I tried to move to San Francisco in 1997 as a young, broke queer. I worked under the table at a cafe and made $100 a week, which was barely enough to eat a Snickers bar for dinner and take the bus to work the next day.”

The first couple of years I could pretend I still lived on $20,000 a year and feel like I was doing really good, and I fast-tracked paying off all my debts. My moms had to lend me money to do this degree because I had defaulted on student loans when I was 20 and I couldn’t access any student loans this time around. They were giving me a monthly stipend and paying my tuition and the deal was I’d pay them back half of their total spend, with no interest, which was an amazing deal.  I owed them $27,000 coming out of school, and I payed that all back in the first year. I also payed back $15,000 worth of credit card debt from supplementing working 20 hours while being in school full time.  Then I had a list of things I had to take care of. I had to get a bunch of crowns on my teeth because I had a ton of root canals with only temporary fillings on them. Probably $7000 went into my teeth in the first couple years. I also wanted to get top surgery more than anything in the world, so I did that in 2010.

I was debt free for exactly one month before my then-partner and I, bought a house in 2011. I signed my name on a $457,000 mortgage. I was literally debt free for one month. I went on a shopping spree in New York and got some new jeans and an expensive shirt and was like, “Woo-hoo. I don’t have to carry any debt this month!” and then we bought a house in San Francisco.

After we bought a house I did the last thing on my “perfect world” wish list which was getting Lasik and now I’m like a bionic person. I remember a time when I thought, “all I want is to be able to always have cigarettes and buy a beer at the end of the work day.” Now things are different. I don’t want those things anymore. I make all this money. What am I going to do with it?

I’m trying to learn how to do good things with money. I spend a lot of time trying to figure that out. I can just give money away. I pay more than half of things when I make more than somebody. For example, with my current roommate situation, we split the rent based on our respective incomes.  We don’t just split the rent in half because she makes a third of what I make. It’s nice to be able to do that. I love buying people dinner. I spend a lot of money on travel too, for me and also for others. That was totally new to me, jumping into this class. I’ve been to Vietnam, Mexico twice, Europe a handful of times. I had previously left the continent once when I was 15 on a school trip to London & Paris that my mom borrowed $1500 from my grandparents to pay for and they never let her forget it. I also do this thing called vacation, where you go away and read books and lay in sunshine. I learned how to do that and how to travel in different countries.  I got a first-class upgrade once. It was to my grandmother’s funeral, so I was a little bit like, “I’m so excited to fly first-class, but it’s a red-eye and I should be sleeping, but I can’t sleep because we’re getting cookies on a plane! It’s like two in the morning and I’m going to eat these cookies and watch all the free movies!”

“I feel like I’m in this industry because I want to shovel out as many resources as possible from its coffers but also so that I can make a getaway after a few more years and then me and all my people who don’t make this kind of money, who don’t have retirement plans, who don’t have this kind of financial stability, we get to go have a good life somewhere quiet. I don’t believe in doing this just for me. I have to do this for other people too, as many as I can. It’s not even enough. The wealth gap is growing so fast and even with the money I’m personally making, I can’t stop it or feel like I’m doing enough to help others.  Sometimes I want to run away from making money, go back to when things were easier and I wasn’t part of a very hated industry.”

I used to just road trip around Canada and the US. That was what we did. Just get in the car and drive to someone else’s town and sit around their mall or whatever.

I feel like I’m in this industry because I want to shovel out as many resources as possible from its coffers but also so that I can make a getaway after a few more years and then me and all my people who don’t make this kind of money, who don’t have retirement plans, who don’t have this kind of financial stability, we get to go have a good life somewhere quiet. I don’t believe in doing this just for me. I have to do this for other people too, as many as I can. It’s not even enough. The wealth gap is growing so fast and even with the money I’m personally making, I can’t stop it or feel like I’m doing enough to help others.  Sometimes I want to run away from making money, go back to when things were easier and I wasn’t part of a very hated industry.

Let’s dig in deeper on what you just said. What is your experience straddling communities of different levels of privilege. One being tech, and others being the queer/activist communities. Especially in San Francisco. What is that like for you?

Moving to San Francisco and having most people not know me here before I arrived with a job in tech—sometimes I feel really ashamed. I’m like, “I went back to school so I could fix my teeth, and I come here and it doesn’t matter who I am inside. I just look like a douchebag to people who don’t know me,” and that’s—and not only because I work in tech, but because I pass as a white guy to most strangers. There’s all these ways in which nobody sees the complexities and in some circumstances those complexities don’t matter. I just have to live with that. People are going to make the judgements they are going to make but it’s scary in San Francisco because it’s a super radical activist community that I wanted to come out and be a part of but I tiptoed around it for the first couple years because I was afraid people weren’t going to like me. I went back to school in software development because I liked computers my whole life and was pretty confident with them but also because I thought it would be a good skill to bring back to my communities. I had worked with some artist nonprofits in Toronto and they’re using the oldest computers, and they’re locked into proprietary software they can’t update because they can’t afford to update it. There’s just all these inefficiencies within non-profits because of a lack of tech fluency, and I was always the person who could fix computers or took a natural shine to that kind of stuff, so I thought why don’t I enhance that in what I go back to school for. It seemed like a good fit, I’ve always liked computers, I was the kind of person if I went to someone’s house and they had a computer- because I didn’t have my own computer until 2003. If I went to someone’s house and they had a computer I’d be like “oh can I hop on your computer?” When I got here I joined this queer SF mailing list and I would send messages saying, “Hey, if anybody wants to learn programming, I’d love to teach you what I know.” Nobody took me up on it. Nobody was interested. And nobody was getting mad at me for it either, but it just felt like I shouted to the dark, and I didn’t really understand why.

“Sometimes I feel really ashamed. I’m like, “I went back to school so I could fix my teeth, and I come here and it doesn’t matter who I am inside. I just look like a douchebag to people who don’t know me,” and that’s—and not only because I work in tech, but because I pass as a white guy to most strangers. There’s all these ways in which nobody sees the complexities and in some circumstances those complexities don’t matter. I just have to live with that.”

Sometimes people will approach me and be like, “Oh, I want to learn how to do what you do,” because they see the part where I have this financial stability, and who doesn’t want that? And I want that for people. So I’m like, “Yeah,” and then they’ll say, “But I hate computers,” and say, “Well, then I don’t know if I can help you.” You have to like this stuff a little bit or find at least some part of it interesting.

Then I started to wonder if maybe my role isn’t necessarily to help with the actual technology, even though I do as much as possible, like I’ll get used laptops from my workplace to people for whom a 2 year old laptop is a game changer, repurpose older model cell phones. There are ways in which I can help out in random instances with hardware, sometimes maybe I help someone with a website, though I don’t have much time to do that now that I work so much. These days it seems like the way I can help my community more is often through straight up funding and spreading fundraising asks to my networks which now contain more people who are outside of queer & activist communities—so I can help tap new sources.

Personally I’m curious, as someone—I grew up in a tiny town, moved here with $40, was broke as shit for a long time. And now I make a good living, and I found success to a degree. And the most prominent feeling from the entire experience, that I still experience today, is guilt. I’m really curious if you feel that too?

Yeah. Oh yeah, absolutely, I feel guilty. I managed to get myself a do-over and things went really well and I didn’t feel like I could take any pride in what I had done. Other people tell me I should, but I can’t. I have a really hard time with doing well while other people are suffering or struggling, and yet, at the same time, when I was broke, it wasn’t fun. I don’t miss that stress. I’m still so aware of some of that stress. I have the newest car now. I got a used Prius, a 2009, and it always starts. I get to do preventive maintenance on it, which no car I’d ever owned before got. I always had cars with weird electrical problems, horns that didn’t work, shot brakes, no heat, just stressful breakdowns waiting to happen around every corner.  It costs a lot more to have a car like that than it costs me to have this 2009 car but I would never have been able to qualify for a car loan before now.

I felt a lot of guilt when a friend of mine said, “You forget what it’s like to not have money,” or when I mention things like retirement. That’s the new thing I want to start focusing on, and I want to figure out ways of building a collective retirement fund or otherwise making sure that I’m not just saving for individual private success because my retirement is not going to be very fulfilling if my friends aren’t there. We don’t have a lot of ways to talk about this kind of stuff with people and I have a tendency to just try to give stuff away rather than be the person who has more. I’m not 100% sure that’s the best thing to do, but it’s all I know right now.

“When I was young and broke and people said how rich people have problems too, I’m like, “Whatever. They have money. I don’t believe you.” And now I make what to me is a ridiculous amount of money and I’m feeling that struggle to be happy. To be clear, some of the things I need to work on for my own happiness will exist at any income level but some of the factors are a direct result of being in such a different place than many of my peers. The guilt, stress, and shame are a constant source of exhaustion.  I don’t have any role models for this, and I have no idea what I’m doing.”

My ex is a public college teacher and she never got a raise the whole six years we were together. When we first got together, I was making almost as much as she was and by the time we split up I was making twice what she is. Every year I would come home and say I got a raise—every year that I got a raise—her face would just fall. She would be saying, “Oh, that’s really good for you,” but her entire face belied what she was saying because it was so obviously really hard for her to hear that and it was hard for me too. She should have been getting raises.  But did I wish I did not do it—not make more money, not get a raise, not bring that into our home and into our community? I don’t know.

Recently I have started to say I have five years left in this industry because I’m having a really hard time with the stress. When I was young and broke and people said how rich people have problems too, I’m like, “Whatever. They have money. I don’t believe you.” And now I make what to me is a ridiculous amount of money and I’m feeling that struggle to be happy. To be clear, some of the things I need to work on for my own happiness will exist at any income level but some of the factors are a direct result of being in such a different place than many of my peers. The guilt, stress, and shame are a constant source of exhaustion.  I don’t have any role models for this, and I have no idea what I’m doing.  I’m often curious how this works for other people who come from financially stable upbringings and who are making this kind of money in their 20s.

Yeah. Well, they probably never had to live on less.

I think they probably are saving a lot of money and not spending a lot of money. But that they consider themselves as not having a lot of money. Which isn’t how I approach it at all. I really had to learn how to save money and to learn to protect my savings account from myself. You know, the me that likes to just spend all the money so I don’t have to worry about fucking up with the money? Now I have learned to save money and then I have this little savings account that is growing with these automatic deposits and it got to a size where I was like, okay now I want to protect it—I don’t want to touch it. But I had never had that ability before to, like, put money aside and not touch it. I think that people who came up with money or who came up with security don’t worry about money like this—especially the tech guys who behave like “It’s not even about money. I just do it because I love it.” I call bullshit on that. You’re making money doing it! I don’t know if you’d be doing it if you also had to scramble for your next meal or didn’t have power and literally couldn’t do it because you didn’t have power. I think that they have a much more compartmentalized idea of budgeting and saving and things that let them think what they’re living on is what they have instead of counting their total wealth.  Not to mention anyone who might have someone preparing their meals, cleaning their home, doing their laundry, or raising their kids.

Yeah.

Imagine that saying:  It takes money to make money. For me, making money was a bit of a slippery slope at first because I was still doing things like spending a lot of money on a credit card and then paying it off with my next paycheck. I still haven’t figured out how to have the money for something I want to buy before I buy it.

Yeah. It sounds like we have very similar relationships to money [laughter].

Tell me more about the Ascend project.

That was my attempt to try to scale up what happened to me. I got involved in Open Source at Mozilla through school. I was a student at the time and I got to work on fixing bugs and was supported and grew into being a respected contributor to the Mozilla Project through continually showing up. That helped me secure an internship which helped me get my first tech job which helped me get to the $60,000 a year new grad gig. With all these code schools coming up, that were charging people, especially people coming from the underrepresented populations who are desperate for an opportunity to get a little bit of this tech money, it looked very predatory to me, and it still does. I wanted to see if I could do something where I could replicate what worked for me. Which was that you get involved, you get a chance to be free to do nothing but learn all day how to contribute to Open Source. Because contributing to Open Source is often a really important marker for someone who wants to try to break into a job in technology. And that’s often reserved for people who have this thing called “spare time,” which is really helped by someone else doing your laundry, cooking your dinner, and raising your kids. Right? This program was inspired by the thinking: what if we paid people to have the time to sit all day in a guided environment like I had with my teacher in school—where their only job is to learn how to be a contributor to open source to make a technical contribution by the end of six weeks.

I had an executive at Mozilla who was very supportive of my plan. We would pay participants an honorarium, cover childcare as needed, transit, we provided breakfast & lunch, we provide a work space, we provided laptops that they would get to keep after the 6 weeks were up and then we walked them through a lot of the stuff that I went through. I did a 12 or 13 week college course where I was in class once a week and then I did the project work in my own time. Ascend was an accelerator so we did six weeks, five days a week, nine to five. I wanted it to be only for people of color and that didn’t happen mostly for reasons of time and then also my own limits of knowledge & connection with Portland.

I had just read a study by the woman who wrote Unlocking the Clubhouse about women in CS and she did a second follow up study on Latinos and Blacks in tech based on L.A. high school students and she highlighted how those populations are actively dissuaded from getting involved in CS at all. Seriously—like “this isn’t for you.” I definitely wanted to work with people who are being told that they shouldn’t be here.

I was running it in Portland because Mozilla had an office in Portland. Immediately people were making fun of me for trying to do something that was reaching out to people of color in Portland because it’s 73% white. If it’s 73% white, that means there are people of color there and I only needed 20 people, so I still thought “this is possible.” I keynoted at a local open source conference to announce it. I was also able to hire a friend who was a WordPress developer and small business owner in Portland. She was a local person and she had freelancing skills I didn’t have so I asked her to come co-lead with me and bring those areas into the curriculum too. She also happens to be a black lesbian woman in tech. It seemed wise to have a good local role model/mentor because I was going to come in and teach and then go back to San Francisco.

“I had a manager who was really great. He was very clear about calling me she, as I had asked, and he would do what I call “pronoun showdowns” on my behalf which is when my manager is calling me ‘she’ to someone who’s calling me ‘he’ and they just go back and forth like that until the other person’s on board. I love watching other people do that instead of having to do it myself.”

I put the call out and I got 43 applicants and I had budget for 20 participants. I interviewed everybody who made it past a programming challenge (free online Javascript course) in order to select people. Out of 20 people, 18 completed the program. 1 of them had to go back to Mexico to deal with a family situation and then for immigration reasons was not able to return to Portland to complete. Another person I had to ask to leave the program because he wasn’t pulling his weight. He was falling asleep in class and not really participating. He just wasn’t at a level of maturity to be able to do the self-directed work that was required in this program. We were there to support and also to expose them to stuff and to try to help them connect the dots, but it was really a guided self-learning space. That was intentional so that each person was learning at their own pace, the idea being that wherever they came in at, six weeks later they were six weeks further from that point in terms of having picked up new skills. It was not the goal that they all hit each milestone in the same way.

It ended up being a really great cohort. There were a range of ages. I discovered a whole new demographic of people that I hadn’t even considered when it comes to not getting great opportunities in tech, which is women over 45 who already have experience in technology but cannot get interviews to save their lives because it’s like they disappeared from the view of anyone looking at resumes. The only advice I could give them was not to put the year they graduated on their resumes. We had three trans women and one trans man. We had 15 women and 5 men. Half the group were people of color. It was a mix of class backgrounds—some people who were actively street involved. The guy that I had to ask to leave was homeless at the time and when we talked about it not being a good fit he said, “It’s because I’m on the street.” I was like, “No, actually, it’s not just that. We asked you not to fall asleep in the classroom because it’s hard on the other 19 people to watch you sleeping while they’re trying to learn. We asked you to leave the classroom if you couldn’t stay awake and we provided a room where you could nap. You couldn’t stand up and go to the nap room and have a nap.” It was really that he wasn’t able to grab the opportunity this time around. He’s a really smart guy, and I hope there will be other opportunities.

I had lined up a few internships for these folks to apply to after. There were a couple internships at a place called Urban Airship. It was intentional that it be two so that the graduates could lean on each other and not be the only non-traditional intern coming in off the street. Outreachy had some internship spots, which is a Open Source Intern Project for non-traditional and non-student people. Three of the participants got into those. One of the women who did the program worked at AgileBits. She helped a couple of people get jobs there afterward. So there’s a pretty decent amount of success for folks that did the program. What’s sad to me, actually, is that the three trans women who did the program, not one of them got an internship or job out of this. And that’s something, if I could do it again, I would try to focus more on ways to move the needle on that segment of the population.

“I got involved in women in tech stuff as soon as I got here and each time there’s that moment where I walk into the room of all the other women and now, when that happens, usually I know at least one person there so it normalizes it pretty quickly if another woman shows she is being accepting of my presence there. Initially in the first couple of years it was really hard to go to those spaces and to hope I would connect with a friendly person who would recognize that I’m just a different kind of woman and be my friend, or just be friendly to me.”

Yeah. That segues into something I’m curious about. Your particular experience being genderqueer in tech—like I read the blog post about the Pinterest bathroom incident and your response to that. What is your personal experience been working in this industry as someone considered different in that way?

I’m pretty fortunate. At Mozilla I got to know several of the leaders in the project through the work I did at Seneca College because a lot of them happened to live in Toronto, some were even from Ottawa and we were all relatively close in age which provided the comfort of shared cultural history that Canadians of a certain age will have. They were all very geeky, friendly straight people, so I came into Mozilla with a safety net of sorts.

As I worked in the Bay Area office,  I shared more information about who I was and what I valued which was usually well received. There was a lot of crossover with where I was coming from in terms of queer/feminist/anti-capitalist beliefs and the values of Open Source. I had a manager who was really great. He was very clear about calling me she, as I had asked, and he would do what I call “pronoun showdowns” on my behalf which is when my manager is calling me ‘she’ to someone who’s calling me ‘he’ and they just go back and forth like that until the other person’s on board. I love watching other people do that instead of having to do it myself.

I got involved in women in tech stuff as soon as I got here and each time there’s that moment where I walk into the room of all the other women and now, when that happens, usually I know at least one person there so it normalizes it pretty quickly if another woman shows she is being accepting of my presence there. Initially in the first couple of years it was really hard to go to those spaces and to hope I would connect with a friendly person who would recognize that I’m just a different kind of woman and be my friend, or just be friendly to me. As I got more confident in those circles, I could move on to talking about what we were there for, whether it was learning Python or Java Script or trying to teach other people. I use a method of proximity and persistent attendance to build up relationships with people.  I suppose we all do that, I’m just doing it with the additional effort of being seen for more than my initial appearance. Once at a women in CS conference, sitting in a session, this woman turned to me and asked, “Why are you here?” I think she honestly thought she was kindly asking a man why he was at women’s conference. Stuff like that still happens.

“I use a method of proximity and persistent attendance to build up relationships with people.  I suppose we all do that, I’m just doing it with the additional effort of being seen for more than my initial appearance. Once at a women in CS conference, sitting in a session, this woman turned to me and asked, “Why are you here?” I think she honestly thought she was kindly asking a man why he was at women’s conference. Stuff like that still happens.”

I wrote that email to the women@ list at a couple of months into being at Pinterest and we have now hired more women so there are going to be women in my office who don’t know about that email, who don’t know me, and that always makes me nervous because that means over time the risk of someone being scared continues to be a possibility—actually, it might have happened the other day. I came to the office from the gym because we have a single stall, gender-neutral shower, which is really great. It’s a solo shower, so I don’t have to worry about using our gendered showers because I wouldn’t actually feel comfortable being in the woman’s shower as it’s a shared space with a bunch of stalls and then a common change room.  While I use women’s change rooms as needed in public gyms and pools, that’s not comfortable for me at work, even though some of my coworkers use my gym and we’ve run into each other there. Anyway, there were no towels in my shower—I call it my shower—so I went to the woman’s shower room and stuck my head in to see if there were towels and there were two people in there, where one of them was—I don’t know how naked she was, but she had a towel on at least some part of her. The other was somebody I knew so I asked her, “Do you have any towels because there’s none—” I said, “There’s none in the other one.” Afterwards I realized that was going to sound to the other woman like a man stuck his head into the room and asked for a towel. That bugged me for a little while, because I get frustrated with not being perceived as how I am inside but I have to let it go. I can’t take it back. Little moments like that can throw off my day sometimes.

There’s this whole thing here about, “Be your authentic self.” The longer I’m here, meaning in the tech industry, and the longer I’m at Pinterest, and the more I get to know people and feel confident in the value I provide in the job that I do, the more I get to be my authentic self. — Honestly, even at Mozilla, where I felt like I was a fairly visible and outspoken contributor, and a leader on some initiatives, I was maybe 10% of my “authentic self.” There’s a part of me that’s like, “You can’t handle an authentic me in this workplace, you really don’t want it. It would be distracting at best. It would be horrifying, maybe, at worst because I am radically opposed to a lot of the norms you take for granted and if I was speaking about that all the time I’d be alienating you instead of you alienating me all the time.”  I’d rather take the hit and be the outlier than make other people uncomfortable.  I’m being 10% of myself and that is enough to get people thinking I’m this eccentric person or this unique character, but it also does draws certain people in which can feel nice.  That helps me identify the folks I can create and dream a brighter future with.

Let’s go macro for a second. How do you feel about the state of tech in 2016? What excites you? What frustrates you? What would you like to see change?

One of the things that excites me, actually it’s something that Pinterest is doing. There are people here who are tasked with building up Pinterest’s being a good corporate citizen. It feels very genuine. If we can’t immediately destroy capitalism, at least people can work to make their organizations be good corporate citizens and yet a lot of companies aren’t even doing this. Pinterest does a lot of outreach and ground work in several communities in SOMA. We provide volunteers for meal service at a nearby soup kitchen. There are bi-weekly meals-on-wheels deliveries to seniors living in SROs in the Tenderloin as part of our new hire onboarding.  I’m part of a group of engineers who started a computer club at Bessie Carmichael, a middle school down the street where 95% of the kids are on free lunch programs and we’re showing up and trying to build relationships & mentoring as well as just showing the kids that there are non-family adults who care about them. Things like that give me hope that there’s some model for accountability among tech businesses in San Francisco.  To the extent that these types of programs help on the daily, we’re engaged and there’s never a question that it’s the right thing to do.

“Honestly, even at Mozilla, where I felt like I was a fairly visible and outspoken contributor, and a leader on some initiatives, I was maybe 10% of my “authentic self.” There’s a part of me that’s like, “You can’t handle an authentic me in this workplace, you really don’t want it. It would be distracting at best. It would be horrifying, maybe, at worst because I am radically opposed to a lot of the norms you take for granted and if I was speaking about that all the time I’d be alienating you instead of you alienating me all the time.”  I’d rather take the hit and be the outlier than make other people uncomfortable.”

I’m always going to want it to be more radical than it is. But here it’s being done in a way that’s very core to the company’s values and considering the size of the company and that they aren’t public yet, it gives me hope that this is going to be ingrained aspect of this company’s culture.

So then there’s the other side which is that a lot of technology in Silicon Valley is being invented for the convenience of the 10% who are making good money. That’s got to stop. When are people going to try to solve real problems? I’m really disappointed that all these people who have all these fancy degrees that they hold over the rest of our heads aren’t doing anything that’s more beneficial to more people. Also people keep saying, “Oh the bubble’s going to burst, the bubble’s going to burst.” I do want there to come a time where tech jobs aren’t so inflated in value. I would be happy to be earning $60,000 a year in a town where that was enough to be comfortable and housing costs were secure so that more people could also have $60,000 incomes and cities weren’t being overrun & overpriced because they’re the nexus of high-risk, high-yield startups.

I was talking with someone last night in regards to the homelessness crisis in SF.  We’ve been going out in the mornings to try (unsuccessfully) to stop the tent sweeps. Where are those people supposed to go? Why isn’t anyone taking Uber’s model and making land grabs of unattended and abandoned lots in San Francisco? Build tiny houses on them and just say, “Oh yeah. It’s like Uber for homeless people.” It’s housing. Real, cheap houses. And if someone who owns this abandoned land wants to actually do something with it, fine we’ll move. But until that point, it’s housing, and it’s safe, and it’s clean, and I don’t know, something really disruptive. It’s not specifically a tech thing. Actually, here’s a good one for tech. Why hasn’t anybody figured out yet how to make a containment system that police can use to stop people from hurting themselves or others without killing them? That’s a great technology problem. Bring on the hackathon for that.

Are there social good hackathons yet?

Yeah. There actually is one called Hack For Social Good. The thing about hackathons is that—and I have been in and organized them even— you don’t get a lot done in a weekend that actually can persist beyond that weekend demo. Also, the organizations you’re trying to create for sometimes don’t know how to scope what they want or what they need into a small enough project for a weekend of strangers skill-sharing. It’s great for getting ideas, and I think people were using them originally as a way to kick off their next start-up or application and then they trickled down into the underrepresented communities as this way for people to network and maybe learn skills.  Maven has done some great hackathons for LGBTQ youth and nonprofits who work with them where several folks have gotten a leg up into securing work in tech afterwards.  That’s a positive outcome, even if the hackathons themselves are mostly prototyping.

“A lot of technology in Silicon Valley is being invented for the convenience of the 10% who are making good money. That’s got to stop. When are people going to try to solve real problems? I’m really disappointed that all these people who have all these fancy degrees that they hold over the rest of our heads aren’t doing anything that’s more beneficial to more people.”

How do you think that your background—where you come from, the life experiences that you’ve had, who you are—impact the way that you approach your work? I feel like your whole interview is an answer to this question but I just want to see what you say. [laughter]

I bring sort of a socialist-communist perspective to things so that right there kind of changes a little bit of power dynamics that might exist that just don’t exist for me or that I don’t care to perpetuate. The feedback I get is that makes me really fun to work with and maybe that helps shape the culture in positive ways since by default I’m always dreaming of how we can do things in ways that are inclusive of the most people.  I like pulling people in to help me on—for example, a week long tech camp for LGBTQ youth. I’ll just tell the whole company what I’m doing and why it matters. Then I’ll get these people out of nowhere who will say they want to help. When they help, it’s transformative for them.  

What I really want, and what’s really at the bottom of anything I do, is I really want to transfer power and resources to places where those are limited and yet to never be the bottleneck of this transfer happening. I do stuff in a scrappy grassroots ways, so I’m teaching people to fish as I go.  I hope I’ll get better and better at that. Anything I do, like the Ascend Project for example everything about Ascend is in a public git repo so anybody could take our materials & notes and go make a similar project happen.

I really admire the programs and organizations that were started in the 60s & 70s that still exist today, and I spend a lot of time thinking about, “How do we do that now? Do we do that now? Is it happening and I’m not noticing it? Are we capable of creating lasting models for social justice? Do we need institutions?” Silicon Valley is trying to convince us everything should be “move fast and break things” but when you’re dealing with people who are marginalized surprise and breaking things can be very destabilizing.

“It’s really important to recognize that people might come into this at any point in their lives. We should be always be empowered to not know what we want to do in our 20s and still get to learn new jobs have dignity, autonomy, and opportunities for mastery of skills. Anyone at any age should be able to do what I do.”

What do you see yourself doing in five or ten years?

Five years from now I want to have my own business and be teaching in some capacity. I want to do the Ascend project but as a business—where I’m able to fund running a training center for folks to be learning tech skills on the job while we deliver products perhaps in partnership with federal government. Trainees can become worker/owners or go start their own thing—like take a couple of clients and go start their own thing because not everybody’s able to or wants to work for someone. Some people really need to be able to work from home or to have more flexibility and so creating opportunities for that is also a priority to me.

My last question for you—this one’s complicated for you. Because normally my last question for folks is like, “What advice would you give to folks who kind of come from similar backgrounds or life experiences or who are hoping to get into tech?” But it feels so much more complicated with you. So I’m like, do we restructure that question? Like, what would you want that question to be? It’s kind of like, “What lessons have you learned that you would like to share with the young ones just starting out?” But… I don’t know.

Well, first of all, I don’t know that it should just be for the young folks because I think it’s really important to recognize that people might come into this at any point in their lives. We should be always be empowered to not know what we want to do in our 20s and still get to learn new jobs have dignity, autonomy, and opportunities for mastery of skills. Anyone at any age should be able to do what I do.

When I did the Ascend project I was asking people to tell me about a problem they had solved. Because I think a lot of people confuse technology with liking computers. But that’s just a side note. Tech work is about solving problems. If you could tolerate getting stuck on something, bang your head against it, thinking you’re a total idiot and you’re never going to figure it out, and then managing to figure it out and get that euphoria of, “Oh my god. I did this thing. I didn’t think I could do a day, a week, a month ago.” And you get a little high from that and you’re willing to do it again, then you can do okay in technology. You could do well in a lot of different jobs. Technology is not this natural talent, a lot of the work we’re doing is not in any way rocket science. Which may or may not even be the hardest thing to do. I don’t know why that’s always the comparison. But rocket science is pretty exact. A lot of this stuff has room in it for you to bring your transferable skills from all sorts of other areas. I want to work with more people who have way different backgrounds, not just people whose lives have gone according to a plan.

I’ve had some people ask a similar sort of question at conferences, like the LGBTQ lunch that happens at Grace Hopper “What’s going to happen when school ends and I’m this genderqueer person trying to get a job?” and, “Is it going to be okay for me?” It probably will, because even though this place is full of white people with money and other privileged folks they’re all pretty nice. It’s a benign, institutionalized system of racism, sexism, heteronormativity. Whatever exists here, it’s super low-key so there’s microaggressions, guaranteed there’s microaggressions. So, you’ll survive and then it’s on people to figure out what they can tolerate and where they’re going to feel comfortable and successful.

That’s my advice, “You’ll survive at the very minimum!” Someone’s going to find comfort in that. You know what sucks is I can’t say you will thrive. I don’t think I’ll ever be able to say that to somebody who comes from any kind of underrepresented population, that they will thrive in this environment. I don’t see even the people who fit the mold thriving here. I think the current Silicon Valley model has isolated and cut off its workers from humanity and so those of us who come in knowing a little more about what’s happening outside this bubble just feel the pain more acutely. However we also have outside communities to retreat to in healing, I’m thankful for the contrast and I hope that others coming in will have that already or create it as needed.

“That’s my advice, ‘You’ll survive at the very minimum!’ Someone’s going to find comfort in that. You know what sucks is I can’t say you will thrive. I don’t think I’ll ever be able to say that to somebody who comes from any kind of underrepresented population, that they will thrive in this environment. I don’t see even the people who fit the mold thriving here. I think the current Silicon Valley model has isolated and cut off its workers from humanity and so those of us who come in knowing a little more about what’s happening outside this bubble just feel the pain more acutely.”

I grew up in San Jose, California. My family was middle-class. My father was a software engineer, my mother taught school. It was a very conservative household, or at least California conservative. That really textured my world view.

People ask me now, how that affected me being trans, and it’s… well, the thing that you are is such an anathema to the culture you’re brought up in. It’s problematic. I think the biggest impact was that I lacked any real sense of self. I was just trying to be what everybody around me wanted.

Teachers loved me, because I was always doing what they wanted, and I was way more concerned with the adults in my life than my peers. I always did what my parents, particularly my mom, expected. I was always filling particular roles. That really drove a lot of my life in terms of what I did. It wasn’t until decades later, post-transition, where I start to develop a real sense of self. And then I’m think, “Oh, that’s weird—how did I live so much of my life having no real sense of who I was, just trying to be what everybody around me wanted?”

Were you exposed to creativity or technology, or any of those concepts early on?

That’s an awesome thing about the household I grew up in. My dad worked in the software industry. We had computers and game systems in the house my entire life. That was always something we had. We had a Commodore 128. It has the basic interpreter on there. You could write little go-to loop-type things. Actually it was my friend’s dad who had the first computer I ever saw. I was—I want to say—three and a half, maybe four years old, and I’m over at my friend’s house and he’s got this Apple II. It has this green screen. My friend’s dad shows us this vector drawing of a frying pan. You can’t even see it on one screen all at once. You have to scroll or zoom out. I see this and then he shows this little game he wrote of where these little horses race across the screen. Seeing that was the moment where I was thought, “This is the most amazing things I’ve ever seen.” That moment still stands out in my head when people ask me, “How did you get into technology?” That moment was really defining.

Walk me from that moment to working in tech. How did you get into it? What has your career experience been like?

When I first started college I wanted to do something a bit different. I wanted do music for video games. I was strongly pushed by my mother to go into computer science. “You can make all this money doing software.” And so I went into it. It was an interesting thing—I was good at it and I did enjoy it. I think I still regret not following my heart at the time. I pursued a computer science degree, and then started working in the software industry. That’s all I’ve done since. It’s an interesting field. There are times when I love it, and there are times when I hate it.

“I was presenting very gender-queer in interviews. And not getting any offers. Finally, one day, I gave up. I went to an interview without nail polish, no lip gloss. I presented as male as possible. Lo and behold: I got an offer. The thing of it is every time I’ve been brought in for an on site interview, where I was presenting male, I received an offer.”

What are some of the highlights, and proudest moments, and things that have excited you the most about your time in tech?

That’s a great question. I was really proud of my work at One Medical. Before I left there, I took a few minutes and ran a query on the git repository. I wondered, “How much of this code base did I write?” It turned out to be around 40%. During the time I was there, the software team was on average of about five people. Sometimes less, sometimes a little bit more but I was the first developer they hired. Writing that much code could potentially be embarrassing, except that I’m very particular about not writing verbose or excessive code. I write what I need.

I’m really proud of what I did there. I’m proud of the type of work that we did and the direction we were going. That was a really neat part of my career.

Your work has certainly impacted me as a One Medical member.

I look at it, and it’s this was a really big thing that I poured a huge part of my life into, and I look at a lot of other things I’m really proud of, and I feel like none of them quite stand on that same tier. I think I wrote some beautiful code when I was doing device drivers, some really elegant things. I solved some really hard problems, but they just don’t stand up in terms of the long term term impact that they have. One thing exciting about my current role is that it has the same potential for long term impact. We are building tools to fight harassment. To me, that is just as big as doing medical software.

Tell me more about that.

Being harassed online sucks. And I’m working for the biggest player in open source community platforms: Github. They made a decision at a very high level to put money and people behind actually making Github a platform that is safe and inclusive. I’m building up a team; we’ve got a really good foundation in the works. It’s going to be a while until we have real tangible results, and it’s not an easy area. There are a lot of really tricky aspects to it. But those are challenges that I’m excited to rise to. I want to build the online space that I want to have for myself. I want to build an online space that sets the tone for the future. I don’t want just to make this platform good. I want to make it the best of show: a place where voices are not suppressed and that people feel safe.

“I want to build the online space that I want to have for myself. A place where voices are not suppressed and that people feel safe.”

On the flipside, what have some of your biggest struggles been in your career?

The biggest struggle was post-transition, or probably mid-transition, when I was trying to figure things out and just living in a sort of gender-queer life, and I needed to find a different job. I was determined that I didn’t want to work any place that won’t accept me as I am. So I was presenting very gender-queer in interviews. And not getting any offers. Finally, one day, I gave up. I went to an interview without nail polish, no lip gloss. I presented as male as possible. Lo and behold: I got an offer. The thing of it is every time I’ve been brought in for an on site interview, where I was presenting male, I received an offer.

So I got that job. I worked there for a couple of years, and then there were some really negative situations there, however I did manage to transition during that time. That company ended up being a mixed bag. I had some solid support from my peers, but I could’ve had a lot better support from management. I realized, at some point, that the professional relationship had become fairly dysfunctional.

I needed to move on. I started interviewing for other positions. At this point, I was presenting female. It’s a lot different interviewing for a tech job when presenting female.

The bad interviews were not a big deal. If my skill set and approach don’t line up with a company, I expect them to pass. But the good ones… the good ones kept resulting in rejection. When a company decides to keep moving forward, especially when it’s been multiple rounds, it’s clear that they think you are suited for the job. They are spending time and money to pursue you. These companies would get to the end of all of this and then decline me on the grounds of something we discussed as a non-issue in the very early rounds of screening. For example, “We think we want somebody with more such and such experience.” and you’re like, “Wait, we talked about that exact thing during the first phone screen!” Why would you put hours of your employees’ time and mine into this interview process if that thing was an issue?

It’s clear there is a bias at work. A lot of men don’t want to work for or with a woman. On top of that, I never know who might have read me as trans and had their own transphobia come into play. But it’s pretty easy to sabotage somebody in the interview process if you want to. And I’m sure anyone with a non-privileged background faces these exact same type of things where all it takes is, “I don’t think they’re a good fit,” or, “Nah, they made me kind of uncomfortable,” or, “I really didn’t like the way they answered this one thing.” It’s much easier to sabotage somebody than it is to champion for them.

“It’s pretty easy to sabotage somebody in the interview process if you want to. And I’m sure anyone with a non-privileged background faces these exact same type of things where all it takes is, ‘I don’t think they’re a good fit,’ or, ‘Nah, they made me kind of uncomfortable,’ or, ‘I really didn’t like the way they answered this one thing.’ It’s much easier to sabotage somebody than it is to champion for them.”

Let’s dig deeper into that because I’m sure you have a lot to say. You worked in tech for 15 years before you transitioned. So you have tons of experience in the industry. How is life before and after?

I have a much different understanding of privilege. There’s a difference between knowledge and understanding. And to fully grasp the level of privilege I was afforded, it took this very painful experience of having to job search for over a year, and a lot of great interviews that my previous experience said, oh yeah, you have an interview like that you’re going to get a nice offer, you’re going to have multiple offers coming in. You’ll be in this great competitive situation!

Instead I would find that even when things went really well, when I was expecting to receive an offer. I wasn’t sure if I wanted to work at some of these places. I would have been the first woman engineer. Do I really want to be that person? I’ve got a thick skin. I can handle it. I’ll do it.

But then they make the decision for me. They decide I am not up to the challenge of being the first woman. They can’t legally turn you away for that. But they can always come up with some other reason.

These situations brought me to very deep understanding of privilege. It is a much more nuanced and deep and personal thing than I understood before that.

“I’ve had to learn a lot about this privilege thing, and how much I had, and how much I’ve lost.”

There is a huge difference between the male friend who knows, “Oh, it’s not safe for you to walk down this street at night,” They will walk you to your car, all that stuff. They know about that and they do the right thing. But it’s a very different experience when you feel mortal terror. When you have to that walk by yourself, and you have some guy on a bicycle circling up, and coming up towards you, and approaching you, and– There’s a very different feeling and if you don’t have that experience, you’ll never fully understand. You will know. But you won’t understand.

That’s a much scarier place than just not being able to get a job. I’ve had to learn a lot about this privilege thing, and how much I had, and how much I’ve lost.

All of this has impacted me in a professional capacity. I am a huge champion of mitigating and eliminating bias in hiring. We have to really work hard to do this. Fortunately, we have good economic data on why you should do this. Ultimately companies should do this because it’s ethical, but sometimes you can’t always win over a board with the ethical argument. But you can at least win them over with the profit argument.

My experiences have made me a big advocate and champion for how to we empirically cut biases out of these processes, how do we give more opportunities to people from underprivileged backgrounds, how do we make tech a more equitable place? It already has huge economic barriers to entry, for instance, if you can’t afford to have a computer in your house. If I hadn’t grown up in an upper middle class family, would I be in tech right now? Probably not. I might have eventually had access to a computer at school and maybe that would’ve been enough, but it’s very different having had access to a lot of really interesting pieces of technology very young and very early and being able to just play with these things and grow to love them.

Where do you find your support networks?

Professionally or personally?

Both.

Personally, I’ve been very fortunate in terms of the circles of friends that were around me through my transition. The nature of all those relationships changed more than I thought it would. But in pretty much all cases, it was positive – even when that meant the distance in some of those relationships increased. I had a good group of friends to begin with, and that group turned into what I needed it to be. The nature of that circle of friends has changed and who I’m close to and who I’m not, but I have some absolutely amazing people in my life that are there when I need them, and people that I can count on when I feel like I can count on no one else.

“My experiences have made me a big advocate and champion for how to we empirically cut biases out of these processes, how do we give more opportunities to people from underprivileged backgrounds, how do we make tech a more equitable place? It already has huge economic barriers to entry, for instance, if you can’t afford to have a computer in your house. If I hadn’t grown up in an upper middle class family, would I be in tech right now? Probably not. I might have eventually had access to a computer at school and maybe that would’ve been enough, but it’s very different having had access to a lot of really interesting pieces of technology very young and very early and being able to just play with these things and grow to love them.”

Professionally, I feel like I’m only just dabbing my feet in. I’ve only been functioning in the professional world in a gender-variant way and then trans way for like the last four years. I don’t think I really gained much during the genderqueer portion of that, but once I transitioned and was presenting fully female, I have been able to establish some really good professional contacts. I was able to get more involved in organizations like Lesbians Who Tech and connect with other ladies in tech. That’s been very helpful.

It was a huge thing walking into GitHub and finding that there was a built-in support network of ladies there, who are in technology. And having lady managers as peers was actually a big thing. My previous company was too small for me to have any peers, let alone peers of the same gender as mine. That’s been huge. And that’s very recent, but there’s a couple of those people I know that long after I leave this place, they will still support me. I know who to go talk to. There’s experience and depth there.

How do you feel like your life experience has shaped the way that you approach your work?

It definitely shapes how I view the projects I’m working on. I am fortunate to get to take on a project that is directly related to being part of an underprivileged group. I have friends who’ve been deeply harassed for being trans online. Being able to directly work to change that is an incredible professional opportunity.

I have a fairly quiet online profile right now. Because of that, I haven’t faced a lot of direct harassment myself. But I’ve watched this play out in some friends’ lives. It’s personal. It is a very real thing, and being able to do something very real about it is very meaningful.

Earlier we were talking a little bit about really grasping the level of privilege that exists if you are a perceived straight, white, cis male. I’m not white, but I’m “white enough,” at least in the Bay Area. That’s definitely something I’ve started to understand better recently. Maybe some place else, I wouldn’t be white enough.

“We want the a diverse spectrum of candidates. We want to ask all of them questions about diversity, inclusion, and social impact. Those answers matter just as much as the technical questions. It has an amazing way of normalizing a lot of things. On top of that, you’ve now selected for people that are going to be looking for those qualities in others around them. You can leverage the effect people intrinsically wanting to hire others like themselves in a positive way, instead of the typical homogeneous, limiting way.”

These thing impact how I think about hiring and building teams. It changes the types of questions that types of questions you use.

We want the a diverse spectrum of candidates. We want to ask all of them questions about diversity, inclusion, and social impact. Those answers matter just as much as the technical questions. It has an amazing way of normalizing a lot of things. On top of that, you’ve now selected for people that are going to be looking for those qualities in others around them. You can leverage the effect people intrinsically wanting to hire others like themselves in a positive way, instead of the typical homogeneous, limiting way. That way tends to result in teams entirely of people from privileged white male backgrounds. I want other people to care about diversity inclusion. I want other people that are different than me.

I also want other people who might be like me. If you’re the only lady on a team, you desperately want to add another lady to that team. If you find someone who is qualified, you’re going to fight for them. Similarly, like if you’re a person of color, or if you’re a trans. Occasionally will have an interview where the video chat will come up, and I will suspect that the candidate is trans. I will want to give her extra privilege. And I have to actually fight a different type of bias there.  I still have to evaluate her on the same criteria I would any other candidate. Even though personally, I’m like, “I’d love to hire you just because you’re like me.” It’s the same thing. It’s an odd sensation.

Totally.

It ties in a little bit to my experiences, being functionally the same candidate presenting male and presenting female. It’s not that I answered questions differently, or did less well on the technical portions. It was like, yeah I’ve dealt with a lot of identity stuff, but that didn’t change in how smart I was. That didn’t change in how well I do in technical interviews. None of that changed, and yet the responses to me changed dramatically.

Did you experience similar biases when you were employed as well?

Oh,  I can talk about that little bit. In my previous position, it was a place where they all knew me through my transition (which was gradual). Having folks who are not close to you on a personal level see you in both genders is a little odd. I definitely saw ways where I was treated differently after transitioning. In the 15 years of my career prior to transitioning I was never, ever labeled as “aggressive.” Sometimes “assertive,” even “overly energetic,” “frenetic.” All sorts of labels would be applied to me, but never “aggressive.” Post-transition I got that feedback constantly. Especially when I was seeking any form of promotion – where that very behavior that almost guarantees reward of promotion in a male – it was used as criteria to claim that I was unsuited for a particular promotion.

“In the 15 years of my career prior to transitioning I was never, ever labeled as ‘aggressive.’ Sometimes ‘assertive,’ even ‘overly energetic,’ ‘frenetic.’ All sorts of labels would be applied to me, but never ‘aggressive.’ Post-transition I got that feedback constantly. Especially when I was seeking any form of promotion – where that very behavior that almost guarantees reward of promotion in a male – it was used as criteria to claim that I was unsuited for a particular promotion.”

If you get things done as a lady, you’re too aggressive.

Have you had mentors or people that you’ve looked up to along the way?

I have had people who have been mentors in very specific technical areas. I learned a lot about what good code looks like. When I was writing device drivers, I worked for this guy who was a terrible people manager, but a marvelous coder. He wrote beautiful code. That was when I really developed a sense of what beautiful code is. He was the type of person who wrote such beautiful code that almost anything you presented to him, he would not be super happy with. The highest praise was if you put something in front of him and he’d just scowl at it, but he’d have nothing to say. He would be essentially unhappy with it because it wasn’t something that he wrote, but he couldn’t actually come up with any criticism. I learned a lot from that.

I feel like I learned a lot about software management from watching a lot of people do it poorly. It’s an area where I can’t actually talk about a good mentor I have had because it’s a case where I, for the most part, just watched people fumble. I’ve also watched people who fumbled in many areas and then did one or two things right. I’ve tried to glean all these little bits. My strength as a manager is in aggregating all these lessons I’ve learned over years of watching people do things, both good and bad.

There was also a time when I had someone further up in the organization, two levels above me, at the start of my career, who saw potential in me as a leader. She started working with me to develop leadership traits and took time to meet with me one-on-one. That was actually really powerful now that I think back on it.

This was pre-transition for me. I never realized at the time what it must have taken for her to reach that level in that company as a woman. Now I can only imagine the battles she had to fight and what she had to do to get there. What an honor it was that she took time to mentor me.

More recently, I’ve been at a lot of startups and smaller firms. You often have a lot less opportunities for mentorship in those cases. You have a lot of opportunities for growth, but essentially if you’re at too small of a company, you have to look for external mentorship. This goes back to the identity thing I was talking about. If you don’t have a strong sense of self it’s hard to have really solid goals about what you wanna do with your career. Without clear goals it is easy to neglect mentorship and other career development.

It fascinates me that the shift into my actual gender was accompanied by a much clearer set of career and personal goals. Without low level psychological needs being met you can be blind to the higher level stuff. And it’s weird that you can be unaware that those needs are not being met.

How do you feel the state of tech in 2016? You’ve been here for a long time. What excites you, what frustrates you?

The thing that excites me the most, is that the conversation around diversity in tech feels like it is taking on a very vibrant life and it is very real. It’s both data-driven and personal, and we’re seeing that conversation play out, and we’re seeing the beginnings of real change. On the flipside, we’re seeing some really nasty counter-arguments, and we’re seeing a lot of people basically defend this concept of, “No. It’s a meritocracy. If you’re having issues, it’s because you are not good enough,” yet the data says that’s wrong.

“The conversation around diversity in tech feels like it is taking on a very vibrant life and it is very real. It’s both data-driven and personal, and we’re seeing that conversation play out, and we’re seeing the beginnings of real change. On the flipside, we’re seeing some really nasty counter-arguments, and we’re seeing a lot of people basically defend this concept of, “No. It’s a meritocracy. If you’re having issues, it’s because you are not good enough,” yet the data says that’s wrong.”

We’re seeing some companies are stepping up and doing things about it. And my hope is that those companies that are doing something about it don’t just play lip service to diversity and inclusion, but actually really step into that role and say, “We are going to do this really well,” and especially if they then see the rewards and they see economic benefits. That will really help as time moves forward, we’ll see a lot. We’ll see big shifts. If you look at other industries that had deal more direct with affirmative action in the 70s and 80s, you’ll see this indeed happened. Even some industries that are still known for being incredibly sexist. Take Law, which is known for having some really nasty misogyny baked into the system and yet we’re also still seeing that female lawyers are pretty big percentage.

I see tech in a position to actually do better. I want to see tech sidestep the “lean in” approach. Can tech avoid teaching everyone from diverse background to simply behave like the status quo? Can we instead bring a diversity of approaches and personalities into the workplace? The status quo is to expect underprivileged people to to go and behave like the white men in the industry. The more you can behave like these men, the better you will do.

We’re seeing in tech companies that are willing to actually move women into leadership. We do even better when we don’t just look for the women that emulate men but we look for women and people of diverse backgrounds that just are themselves. They bring a slightly different tone and perspective on things, as opposed to just the very stereotypical driven Type A masculine. Type A females are great but they are very different than their male counterparts in terms of their approach and what their goals are. And we’re seeing this type of shift, very slowly. I feel like we’re just at the beginning of this, which is a little painful, but we’re seeing that these shifts are happening and that there are more opportunities.

“The status quo is to expect underprivileged people to to go and behave like the white men in the industry. The more you can behave like these men, the better you will do.”

And we’re definitely seeing a lot more companies trying to just fix their diversity from this big number-game side of it and be like, “Well, we need to hire more women, we need to hire more people of color.” And that by itself is not good enough, because we’ll continue to maintain the reality, most women and people of color leave tech after less than 10 years. If we just hire diversity and we don’t build support networks, these people will be bullied out.

At my current company, I am part of several internal support networks. We are building sub-communities around being Latina or being a woman, etc. We are building these support networks internally in parallel with our recruiting efforts, and that’s a huge deal. And I’m seeing a couple other companies that are doing a pretty good job of that too. They understand that they can’t just hire people from diverse background, because they’ll end up leaving. You have to actually put a support system in for them. And as we see that, we’re seeing this growth and this vibrancy, and you see these just amazing things.

“Most women and people of color leave tech after less than 10 years. If we just hire diversity and we don’t build support networks, these people will be bullied out.”

What are you working on right now, either work-wise or personally, in 2016?

Professionally, I’m really working to build a solid team, to accomplish these goals that I have in terms of fighting harassment and abuse on the GitHub platform. That’s just an exciting thing to be working on, and I’m really excited to be recruiting and hiring for that, and trying to put in really solid processes around how we’re going about building the software we need. That’s exciting.

On a pseudo-professional note, I’m trying to do a lot more speaking and writing about these topics. There’s a reason I’m openly trans on the internet. I made a very conscious decision about that a year ago. I could very well be stealth on the internet. I can mostly be stealth in person, but I made a conscious decision that I have this privilege and if I’m stealth, I give up my voice. And it’s really hard to drive changes solely from the perspective of outsiders who are allies without the voice of those who are actually affected.

One of my big things for 2016 is doing a lot more speaking, and writing about this very topic, and sharing my stories. I’m an empiricist, so I want data on all this stuff. And I get frustrated. There’s not a lot of good data on many aspects of this. In some areas there’s great data. Like we know a lot about gender bias in terms of how it affects interviews. But there’s a lot less about how transphobia, or homophobia, etc come into play. So often the best we have is our stories and our anecdotes. And especially since they’re very real. We may not be able to statistically prove that this is happening, but we can appeal to people’s life experiences and hope they say, “Oh, yeah. That happened. I could totally see that happening more, and that shouldn’t be happening. What can I do about it?” I definitely am trying to use my voice to make the world a better place for anybody from a non-privileged background.

I would love to hear you speak. You’re so eloquent in everything you’ve said here.

Thank you.

Where do you see yourself in five or ten years? Do you think you’ll still be in tech?

Probably. I could see using some of my work, in terms of the trust and safety, could move me someplace different. But, if I do that it would still be someplace clearly related to these very issues of making sure that people have safe and inclusive spaces and that we’re building these types of places both in real life and on the internet. If I stay in tech I definitely hope to tackle some level of upper executive-style work within the tech industry. I think I have a lot to draw on in terms of that, and that’s a direction I would like to see my career go long-term.

What advice would you give to folks going through similar struggles or coming from similar backgrounds to you in tech?

That’s a hard one, because there’s a degree where I want to say,”Don’t give up.” And there’s another part of me that feels like that’s the most flippant advice in the world.

It was incredibly emotionally destructive for me to deal with the rejections of interviews I knew went well. I expected to be rejected for something that didn’t go very well, or I could tell we were just on different pages regarding management style. But the interviews where it was clear that we synced and it was clear that there was a good match and a good fit…. To get turned down for those was just unbearable. And no, not just once or twice — the first couple times you dismiss it. By the third and fourth time, it was really so incredibly emotionally destructive.

It’s hard for me in good faith to say, “Just stick it out, it’ll be fine.” We need diverse people in tech. I don’t know what the answer is there. It makes me sad that that’s the case.

“I’m an empiricist, so I want data on all this stuff. And I get frustrated. There’s not a lot of good data on many aspects of this. In some areas there’s great data. Like we know a lot about gender bias in terms of how it affects interviews. But there’s a lot less about how transphobia, or homophobia, etc come into play. So often the best we have is our stories and our anecdotes.”

We need to keep fighting to eliminate these biases and make sure people really do have a fair chance. Yet I know that not every company is trying to do that, and so I don’t know what the answer is. There’s a school of thought out there advocating that underprivileged folks should just be the entrepreneur and go that route. But then you have the problem of, yeah, you can do that, but the bias is then going to happen to you at the funding level.

The best I can do is try to leverage the privilege in my life to improve these situations. I have this privilege, I have a job, I have a position, I have authority. I can use that to try to fix these problems from that side. What do I tell someone who is young and up-and-coming? I can say, don’t even apply at the places that are shitty?

[laughter]

I don’t know how you make it. We’ve built a system that is so just difficult and ultimately cruel. I’m really hoping to see some of the very big players build out better programs for early engineers, early career engineers. I’m also hoping to see them build out better support systems for people in their mid-to-late career so that they can bring in women and people of color that have managed to survive and make it a good place to be. We have to see some big changes, both from start-ups and also from the big players, the big employers, the ones that employ tens of thousands and not just a few hundred here and there.

I was born and raised in Boston. My parents are immigrants from South America, and I am the first generation American in my family. I grew up in acity called Somerville, a really nice area outside of Boston that’s been getting more attention lately. Mostly, it’s experiencing gentrification, partially led by Harvard, but ia nice diverse city made up of immigrant and working class families.

When my parents left Brasil for the U.S., they left behind interesting lives and successful careers there. A lot of people assume that every immigrant who came to the US was looking for a better life or to chase the “American Dream,” but my parents didn’t have much of a choice. My older brother needed open-heart surgery and the only hospital successfully operating on children was in Boston. So my parents came to the US so he could get the life-saving surgery and care that he needed.

“When my parents left Brasil for the U.S., they left behind interesting lives and successful careers there. A lot of people assume that every immigrant who came to the US was looking for a better life or to chase the “American Dream,” but my parents didn’t have much of a choice. My older brother needed open-heart surgery and the only hospital successfully operating on children was in Boston.”

Not knowing English or knowing anyone here, they realized pretty quickly that it was really hard work. With few options, they started their own house cleaning business. They made flyers that read, “We put your house to shining.” I was too young to really understand but when I found a copy of the flyer when I was about 13 or 14, I thought it was amazing. I showed my mom and we laughed for a moment, but we then talked about how hard it was for her to be a domestic worker.

After my parents divorced and my mother switched careers, I saw her blossom into this really awesome woman. She started her experiences and background to make positive changes around her. She became an advocate for immigrant women, survivors of abuse, domestic workers and became a bit of an organizer.  As a kid, I didn’t fully appreciate what she did. I just assumed, “Oh, this is my mom. This is what all kids do. They go to these rallies, right?”

In your pre-interview that by the time you were 18, you already dealt with depression and experienced homelessness, you survived domestic violence, and you’ve given birth to a child.

A lot happened in my young life and I think when young people share their tough experiences, society’s first instinct is to blame their parents. My parents loved me, cared for me, and worked hard to do a lot for me. The issues I faced were complex and layered and the reality is that they were struggling too.

Sometime in my journey through middle school, I became depressed. I wasn’t sleeping, I was anxious, and I was having a hard time finding myself. My doctor was hesitant to label it “depression” and convinced my mom to take me out of my current environment to see if a change of scenery for an extended period of time would help me. She did. I spent 2 ½ months in Brasil with her and my brother learning more about my culture, visiting family, riding horses, and being away from what felt like a negative and toxic environment. But the trip had to end and I eventually had to come back home.

I think my parents were convinced that my peers were driving me into a downward spiral so they decided at the last minute to enroll me into a private catholic school in the next town over. Horrified, I spent days crying in my room. The new school was supposed to be a new chance for me to be around people who were smart and driven. The problem was that dozens of other parents felt that way too and sent their kids to this school thinking it would resolve all of their core issues. It ended up feeling like a space, a breeding ground, for young people with complex issues who were turning to drugs for relief.

“Since it was a Catholic school, we definitely did not receive information about making healthy choices around relationships, dating and sex. We weren’t provided with information on how to keep ourselves safe or recognize signs of abuse. We, the girls, were just expected to keep our legs closed.”

And since it was a Catholic school, we definitely did not receive information about making healthy choices around relationships, dating and sex. We weren’t provided with information on how to keep ourselves safe or recognize signs of abuse. We, the girls, were just expected to keep our legs closed. And the message at home wasn’t much different. I was the only girl among my siblings and often felt the burden of supporting my mother to help provide for the family. I did a lot of cleaning and cooking and my mom reminded me that as a kid, she was already the head of the house, hand-washing everyone’s laundry, cooking dinner every day and responsible as the head caregiver for her own 4 siblings. Her expectation for me was not to be an adult, but I was expected to be responsible.

“Having a lot of responsibility and never really getting the help I needed to cope with my issues made me a vulnerable target.”

By the age of 14, I was in school full-time, involved in a ton of extracurricular activities, babysitting and working as a hostess in a local restaurant so that I could help pay bills. Every month, I would help my mom sort through the bills and make phone calls to service providers to dispute charges or request help. My mom knew how to do this, but she explained to me that she felt her english was so bad that people would never take her as serious as they would take me. That even though she was a woman in her 40s, her broken english meant a child with no accent would have more respect in the US. And she didn’t get this idea from nowhere, it came from years of people telling her that they couldn’t understand her or that she should leave the country if she can’t learn english properly.

Having a lot of responsibility and never really getting the help I needed to cope with my issues made me a vulnerable target. During a very troubling time in my life, I met  someone a little older than me who maneuvered his way into my life by offering what a young vulnerable girl needed at the time: support. And this isn’t an uncommon tactic. People can sometimes sense when someone is going through something or feeling very vulnerable, but there are certain kinds of people that feel that and use it to prey on them.

“During my junior year of high school, I found out that I was pregnant.”

During my junior year of high school, I found out that I was pregnant. I thought, “Oh my God! This can’t be happening to me. I go to a Catholic school! My parents will hate me.”

To of add a layer to that, I knew that my mother was also a young mom and then my grandmother was a young mom, that my aunt was a young mom, and it continues across several generations. And since they are Latinas, I like to talk about the reality of teen pregnancy in our culture. In our communities, young motherhood isn’t framed as a negative outcome. At the same time, young motherhood isn’t the expectation. But in a culture where women are denied access to quality education and/or prevented from pursuing careers, the next step in life for young women is marriage and/or motherhood. And that was the story for a lot of the women in my family. There was no reason to wait until 30. If you didn’t intend on going to college or establishing a career, what are you supposed to do for over 10 years between your high school graduation and the “ideal” age of motherhood. But what happened, at least this is how I see it, my parents assumed that because I was born in the US, that I would adopt American cultural norms and beliefs.

But I got pregnant at 17 and the first adult I told was my school nurse. In theory, you would think the school nurse would understand, what is essentially, your health condition and provide you with unbiased advice. You assume that as a medical professional, they will help you. Being in a Catholic school made my pregnancy a little more complex. What I heard was, “You already made a mistake so you can’t make another one.” Of course, this was the discussion around my reproductive choice and instead of providing me with all of my options and going through what the best choice was for me might be, I didn’t have a choice. Despite that, I walked away thinking about the reality that I could still get an abortion and no one would know. I could just do it, tell no one, and start all over. But I think my nurse knew that, so she told all of my teachers about my pregnancy. So here I am: pregnant, junior year in a Catholic school and I had nuns and teachers pulling me aside to tell me what decision I should make and shouldn’t make. “Oh, one sin can be forgiven but not two.”  

“But I got pregnant at 17 and the first adult I told was my school nurse. In theory, you would think the school nurse would understand, what is essentially, your health condition and provide you with unbiased advice. You assume that as a medical professional, they will help you. Being in a Catholic school made my pregnancy a little more complex. What I heard was, ‘You already made a mistake so you can’t make another one.'”

I was young and really relied on the acceptance of the people around me. And I really believed that if everybody knew that I was pregnant, then noticed my belly wasn’t growing, that they’d know what I did. I thought they would judge me and I thought I would end up regretting the decision. I was stuck in a position where I couldn’t make the best choice for myself. And maybe the choice would have still been the same in the end, but at that time my judgment was so clouded. So, I decided to continue with my pregnancy.

I told my mom first and she couldn’t believe that her daughter was pregnant. And I don’t blame her. There’s an assumption and a false stereotype about what kind of girls get pregnant. And I didn’t “fit into” that stereotype as a responsible daughter, honor roll student, and class representative. My parents were upset and I can understand why. They worked really hard in a new country and fought so hard to shed themselves from the stereotypes that Latinos face in the United States. Then they discover their teenage daughter is pregnant. It felt like the ultimate stereotype and they didn’t support me. They kicked me out that day and I had to pack my things and move in with my boyfriend.

Oh my gosh.

That period was really hard for me, because I was leaving a home where I felt safe and in with someone who I barely knew. I was isolated from the only support system I ever had.

“My parents were upset and I can understand why. They worked really hard in a new country and fought so hard to shed themselves from the stereotypes that Latinos face in the United States. Then they discover their teenage daughter is pregnant. It felt like the ultimate stereotype and they didn’t support me. They kicked me out that day.”

To make things more complicated, he was a marine getting ready to leave for training. Before my first trimester ended, he was already gone and for the next 6 months, I was completely alone. And since I was no longer living with my parents, I finished my junior year of high school and enrolled as a senior in a new public high school.

In September of 2005, I started my last year of high school as the new pregnant girl. To top off the experience, my new guidance counselor learned of my pregnancy and decided to remove me from my honors classes and put me in slower-paced classes. When I asked her to put me back into honors, she told me that I probably wouldn’t even graduate and that I should just try to get by in the lower classes – as if she was doing me a favor. But my pregnancy wasn’t impacting my ability to function in class, and I wanted to learn and I wanted to feel challenged. I wanted to continue on the path that I was on, and I couldn’t do that if people were making decisions for me without involving me. Luckily someone else in the school knew about the situation and really wanted to be an advocate for me, and so she stood up for me and said, “Put her back in honors. If it gets to the point where it’s not going well then that’s a whole different story, but put her back in honors.” And they did.

The assumption is that our peers are the ones who will pick on teen moms or give us the hardest time, but they were actually the most supportive to me. My classmates were amazing. They brought me snacks, they carried my books, and they let me cut the lunch line. They asked me questions about what my experience was like, they offered to babysit, and they spent time with me so I wouldn’t feel so alone. In school, it was teachers who were judgmental and mean.

“Older women are celebrated, supported, and the people around them will help in any way they can. That doesn’t happen for teenage girls. When we are in pain or afraid, we don’t get help. We’re told our pregnancies are punishments and this is the consequence.”

These small gestures helped so much. I was too proud to ask for any assistance, because I didn’t want to be the stereotype of what a teen mom was. I wanted to prove people wrong because I often heard, “You became a teen mom because you wanted free stuff, you wanted handouts.” That fear of judgment actually put me in worse situations because– when I should have asked for help and when I should have gone to people to tell them what was going on, I didn’t want to, because I was afraid they were going to say, “I told you so.” or “You’re just like all teen moms.” People really don’t know what it’s like for a teenage girl to be pregnant, unless you were one yourself. Older women are celebrated, supported, and the people around them will help in any way they can. That doesn’t happen for teenage girls. When we are in pain or afraid, we don’t get help. We’re told our pregnancies are punishments and this is the consequence.

My daughter’s father returned four days before I went into labor. During my daughter’s delivery, there was a moment when I started panicking. Her birth was recorded so I can still watch the moment when I went from grunting to crying to staring at the ceiling. See, throughout my entire pregnancy people said things like, “This child’s going to ruin your life. You’re life is over. You’re not going to be able to do any of the things you ever wanted to do. This is the worst thing that could happen to you.” So as I was giving birth to her, I started panicking, because I realized I was giving life to the person who would end mine. And how do I love someone who is meant to ruin my life?

Because of that experience and internalized belief, I had a very negative journey through the first few years of motherhood. I was diagnosed with depression and prescribed anti-depressants. To make matters worse, I was in a horrible relationship and was constantly told that teen moms like me are never taken serious and that no one wanted to love a woman with stretch marks and a baby. There was no one cheering me on, no one who believed in me, and I felt entirely alone.

At the same time, I was constantly facing barriers in school. The school was only required to offer me tutoring in 4 of my 7 classes during maternity leave. It was the minimum required to help me simply pass the school year. But I didn’t want to just pass, I wanted to do well in every class and graduate with a good GPA, like I would have before my pregnancy. So my psychology teacher volunteered to come to my house every week and tutored me in all 7 courses. She brought my exams and quizzes and held my daughter so I could take them. She held my textbooks while I breastfed and was always proud of my progress. Returning to school was tough, the other teachers weren’t as fond of me or my “situation.” They would refuse to meet with my after school for help and embarrass me in class. One teacher told me in math class that there was no way I could catch up, so I proved her wrong by acing the class.

“I even had to fight for things like the right to pump breast milk twice a day. The school didn’t want to let me because they thought I was trying to find excuse to get out of class. Right. Because what every 18-year-old girl wants is to like skip her lunch break so she can be sit in the nurse’s office pumping milk and nibbling on crackers.”

But I even had to fight for things like the right to pump breast milk twice a day. The school didn’t want to let me because they thought I was trying to find excuse to get out of class. Right. Because what every 18-year-old girl wants is to like skip her lunch break so she can be sit in the nurse’s office pumping milk and nibbling on crackers. That is so much fun.

I dealt with a lot of people who constantly tried to limit my choices and my future. Then closer to the end of that semester, I went back to my guidance counselor’s office to ask if she could help me look over college applications. Most of my friends had already applied and had already found out where they were going, and I was late but wanted to do make it happen. Her response without even making eye contact with me was, “Well, let’s see if you even graduate high school first.”

God.

I walked away from that and thought, “Oh, she’s probably right. I probably won’t be able to do this, and I should probably take things one step at a time.” So I didn’t apply for college. Now, the good news is I did graduate high school on time and I did walk the stage with my class. I did get to stay in my honors classes throughout the whole year, and I did well in all of them, despite being a teen mom. I think, actually, I did better in school because I was a teen mom and because I had something else motivating me to do even better.  But people outside of me and my daughter’s life didn’t see that.  

So, you graduated, you didn’t go straight to college—what were those next few years like for you?

When I was in high school I really, really wanted to go to med school. I wanted to become a psychiatrist. Having been a young person who coped with depression, I knew what people like me needed and I understood the differences in cultural understanding of depression. For example—parts of my family are really religious and there have been times people said things like, “You’re not depressed, you’re just dealing with something. Pray to God. You’ll be fine.”

“No one in my family filled out a college application. I had no idea of what that process was like, I had no idea of what you were supposed to do, when you were supposed to do it, what was normal, what wasn’t.”

I knew at a young age that this was not right.  I just couldn’t articulate or figure it out, but I wanted to become a psychiatrist so that I could serve and help young people, like me. Now, the idea of going to med school was really overwhelming because again, my parents were immigrants and they weren’t citizens, and they weren’t in the best financial places, and no one in my family had ever gone to college. So I knew that first, they wouldn’t able to co-sign loans for me and I felt overwhelmed at the thought of the expense. And even if I chose another career, I didn’t know how to navigate the process.

No one in my family filled out a college application. I had no idea of what that process was like, I had no idea of what you were supposed to do, when you were supposed to do it, what was normal, what wasn’t. The idea of a young mom with no support becoming a psychiatrist felt way too overwhelming. It felt unattainable. So what I did was, after I graduated, that summer I looked at local state and community colleges that would accept late applications.I might not be able to become a psychiatrist right away but I can start the process  by becoming a nurse. It seemed a little more attainable and promised a guaranteed job.  So I applied for college, started in the fall, finished off my prerequisites, and prepared for a career in nursing.

“I entered college with a new identity. I didn’t tell anyone that I was a mom, including my professors. I just so badly wanted to be treated the same as everyone else.

I entered college with a new identity. I didn’t tell anyone that I was a mom, including my professors. I just so badly wanted to be treated the same as everyone else.  The problem was that I was still facing unresolved issues and an internalized belief that I was not valuable. So I didn’t ever explain anything to my professors and by my second year of school, I dropped out. I didn’t have reliable childcare, I was still coping with depression, and I was working a full-time job and living on my own.  I decided that if I was going to accomplish anything, I needed to take care of myself. That I was going to focus on being a good mom and practice self-care.

Wow. How did you end up in tech?

That’s a great question. It’s quite a little bit of a journey from that point to getting into tech. I don’t have a traditional tech background, as I think a lot of people do out here. After I took this break from school I started focusing on myself. I started to deconstruct and redefine what it meant to be a young woman and single mother in today’s society. I started talking to other young moms—which was life-changing—because it really helps when you don’t feel as isolated.

I started realizing that thousands and thousands and thousands of young women across the country are dealing with the same exact thing. 100,000 teens give birth every year—more than 80% were unplanned—and so many of them drop out of school, or feel pressured to leave or didn’t receive the support that they need to stay. Yet, many some of them share that it’s not actually pregnancy and parenthood that makes their lives hard, as we often hear, but it’s actually the way people treat us. It’s the way that our educators treat us. It’s the way a lot gate-keepers treat us. It’s the ways in which people invalidate who we are as just women and humans in society. The minute we become young parents we’re labeled as irresponsible, and told we’re awful people, and that we should just be isolated and not exposed to the general public because we’d cause an “epidemic.”

So I began looking at ways to counter-message the false reality that young mothers are not productive members of our society by leveraging the power of new tech, like social media. My first time trying out this theory was with the Children’s Hospital in Boston, where I developed a comprehensive strategy for using new tech to eliminate the feeling of isolation among over 500 young parents in Boston. That opportunity led to a hire at the Brigham and Women’s Hospital where I expanded the program to make an impact on reducing health disparities and improving health outcomes in the lives of young mothers of color in Boston. Then I was hired by  the Massachusetts Alliance on Teen Pregnancy where I worked on a $5M dollar grant from the CDC to reduce the teen pregnancy rate in two cities by 10% in five years. In a few months, I helped develop a social marketing campaign for two cities. We reached our 5-year targets before year 3.  

“Initially, I thought, ‘There is no way I want to work in tech. I can’t give into that culture or space because, well, it’s tech.”  I thought, ‘I can’t do that. I can’t be for racial justice and reproductive justice and work in tech. That doesn’t make sense.'”

While all of this was happening, I also started a grassroots campaign called #NoTeenShame to change a terrifying message that organizations like the Candies’ Foundation and multi-millionaire CEOs like Neil Cole share with teenage girls about sexuality and choice and I partnered with six other young moms from different parts of the country for its launch and within a week, it went viral and we were being featured in everything from Ms. Magazine to Business Insider.  It was exciting for people to see seven young moms of color across the country were starting a campaign against this multimillionaire CEO. It went viral to the point where he caught wind of it and wrote a response on The Huffington Post about it. It was not the response we were hoping, but it was a win for us none the less. Once that happened, we started getting contacted by just about every organization in the United States that was working with young people to get our insight on how to do the work better and more effectively. We got really busy really fast and people just started reaching up to us and asking, “Well, how can we replicate the models that you guys have used in your respective organizations to help young people? What should we be doing differently?” The series of all those events led to me developing strategic frameworks for using new technology for social impact and finally presenting at a tech conference here in San Francisco last year.

For a long time I envisioned tech as the enemy—I’m a reproductive justice activist. I’m a racial justice activist.

When I wased in San Francisco, I met someone on the executive team at a startup called Honor (where I work now) who was interested in the work that I did,how I accomplished it and how creative I was in using very little resources to accomplish a massive goal. And so we started talking, and I met other people on the executive team. Initially, I thought, “There is no way I want to work in tech. I can’t give into that culture or space because, well, it’s tech”  And so coming into this space, I thought, “I can’t do that. I can’t be for racial justice and reproductive justice and work in tech. That doesn’t make sense.” I had this assumption that social justice didn’t fit into tech, but I think that’s because I based my opinions on the negative stories I heard on the east coast. But once I met the people that were leading the company, I realized that so much of what I assumed about the people in Silicon Valley were wrong. But also that someone like me can still be in tech and be a valuable asset to the work. And as weird as this sounds, I do think I found that special startup that actually developed a really good frame from the very beginning of how they do work. So, I waited a while and I thought about it, went back to Boston, and decided to pursue the opportunity. I thought to myself, “Oh my god. I was 27 years old. I have a daughter. I’m a single mom, and the only family that I have in the US are just four people who live in Boston. And now I’m accepting the  opportunity to move to San Francisco to work in tech.” And that was hard to wrap my head around.

It was actually my mom who said, “Natasha, you can do this. You’ve overcome way harder things in your life.” When she was 27, she was on her way  to the US for a completely different life. And so she said, “I did it, and I’m not saying that we’re the same. But you can move across the country to pursue this. You can do this.” She also reminded me that I had to think about my daughter who’s really interested in science and has been going to all these science clubs. I now have an opportunity to actually be in this field, to actually be in tech, and provide her with an inside view of what this world is really like. She can watch me go through this process and this journey, and she’s going to see how hard it is. She’s going to see the good and the bad, but she’s going to see it. And she’s going to appreciate it. So, it was a combination of those things that made me decide to say yes to the new field and the big move.

So, what was Silicon Valley like for you when you first got here?

There’s been positives and negatives. One of the things that I actually had to overcome when I came here is how fast everything moves. It’s really fast-paced. Everybody told me it was like this, but it was ten times faster than what I’d prepared myself for. And initially, it was really hard, but I also had a really supportive group of people here where they were willing to help me adjust.

“I love that when I’m having lunch and sitting at a table with people who are amazing engineers, or accomplished healthcare professionals, and talented organizers. And we all sit at a lunch table enjoying each other’s company and discussing the very different experiences we’ve had—and how those diverse experiences shaped such an incredible company.”

The other difficult transition is coming from a space where I talked about racial and reproductive justice 24/7 without filtering myself. Prior to this role, I went to networking events where we introduced ourselves by identifying which pronouns we prefer, the issues we’re working on and how we identify. It’s much different here where I’m often asked to introduce myself by position, educational background and accomplishments. And even when I went to events centered on inclusion, I didn’t feel included. How are so many companies  hosting an event on improving inclusion in the tech sector, hosting in spaces that are difficult to access, and not offering things like child-care?

What has been most exciting of activating for you in your work here?

What’s been most exciting is the people that I get to work with. I love that when I’m having lunch and sitting at a table with people who are amazing engineers, or accomplished healthcare professionals, and talented organizers. And we all sit at a lunch table enjoying each other’s company and discussing the very different experiences we’ve had—and how those diverse experiences shaped such an incredible company.

Despite growing up 5 minutes from Harvard and 10 minutes from MIT, I felt so disconnected from people in tech. They seemed so unreachable and different. And I didn’t always see them as the people I wanted to aspire to become. The Harvard grads were the ones moving into our community, pushing families out of homes, so 5 or 6 students could move in, bumping up rent from $1000 to $3000, a profitable idea for landlords. So I witnessed how the growth and expansion of schools like Harvard led to the immersion of grad students into my community, which meant the immigrant and working class families had to leave.

“Despite growing up 5 minutes from Harvard and 10 minutes from MIT, I felt so disconnected from people in tech. They seemed so unreachable and different. And I didn’t always see them as the people I wanted to aspire to become.”

That played a role in how I perceived tech, even though I was using platforms like Facebook. It didn’t occur to me that someone not too distant from me created this. To the teenage me, it was just something that was created by someone somewhere. It took years before I learned that it was created 5 minutes from my house.

It was cool, but it frustrated me because I felt like there were so many issues impacting young people in Somerville and Cambridge and no one seemed to care. And it was frustrating to see people come from all over the world to study here, learn from the community, then leave forever. Now that I’m on the inside, I see how difficult it is to create tools that are genuinely helpful to people—especially if it’s for people of low-income. And it’s frustrating.  

I’m curious to know how that experience, seeing that tech ecosystem in Boston affects the way that you feel about the state of tech here right now?

Boston’s tech scene is very different than it is on the west coast. It’s thriving, but in a very different way. So although I was involved there, it didn’t help much when dealing with imposter syndrome. I think we often frame and consider imposter syndrome as a one time occurrence that we overcome. But what I learned is that it’s a life-long issue that you’re constantly battling. See, when my Boston friends learned the news of my move to San Francisco to work for an Andreessen-Horowitz backed startup, they were amazed. To them, I was doing what so many wished they could do and I was supposed to feel like “I did it!” And I did, but there’s still the reality that you’re constantly needing to be ahead of everyone else and doing incredibly well. I love the field and where I work, but there’s internal self-created pressure to make sure I’m outdoing myself.

“When everyone around you has very similar background, you can sometimes still feel like an outsider. I didn’t have the typical college experience, I didn’t have those amazing internship opportunities, and I didn’t have parents who could introduce me to really cool people or get me jobs or even read over my essay to see if they were grammatically correct. Growing up, I had to do and figure out all of those things on my own.”

But when everyone around you has very similar background, you can sometimes still feel like an outsider. I didn’t have the typical college experience, I didn’t have those amazing internship opportunities, and I didn’t have parents who could introduce me to really cool people or get me jobs or even read over my essay to see if they were grammatically correct. Growing up, I had to do and figure out all of those things on my own. So part of the culture shock is being lost in the conversations centered around privilege.

The other thing too that I notice out here that never happened to me before is we meet people and they’re constantly extracting from you. “What are your thoughts on this?” and “What are your thoughts on that?” And I’m hesitant to share information because also as a woman of color and having done really great work over the past decade I’ve constantly experienced situations where people with power will take a little bit of information from me and then turn it into something that they get credit for. And so, there’s this constant erasure that happens to young woman of color, so I’m hesitant to engage based on this historical experience. Especially if they’re not being transparent with me.

“I’m hesitant to share information because also as a woman of color and having done really great work over the past decade I’ve constantly experienced situations where people with power will take a little bit of information from me and then turn it into something that they get credit for. And so, there’s this constant erasure that happens to young woman of color, so I’m hesitant to engage based on this historical experience.”

The other piece is that I have internalized stigma as a teen mom and it pops up from time to time. I tend to find myself avoiding conversations that might turn into a discussion about me being a single parent that turns into facing a series of invasive questions. Because it happens. Too often. And it’s not intentional, but their unconscious bias just starts surfacing, and they ask, “Well, how old’s your kid? How old are you? Oh my God, that mean’s you were in like…” You literally see them every time look up, do the math, and they’re like, “Oh my god, you were 17! What was that like? What did your parents say?” And it just turns into this whole dialogue that I don’t want to be a part of. Interested in my story? Go read about it or watch Gilmore Girls. I don’t want my struggles to be the center of discussion, especially in a society where we were made to believe that teen parenthood is a bad thing.

How has everything we’ve talked about, both your experiences in tech so far, and your upbringing, and all of your cumulative experiences, how does that effect what is priority to you here? What is priority in a job, what is priority in what you’re trying to get out of Silicon Valley?

So it’s actually really interesting, because I feel like a lot of people out here are really focused on long-term planning. There’s nothing wrong with that, it’s necessary, but I feel like my goals are very different than a lot of people in my position. And that has a lot to do with the reality of how much progress I’ve already made in the past decade. I’ve met and exceeding so many of my own expectations for this period of time and I wanted to spend time acknowledging that and perfecting and improving everything I do now. It doesn’t mean I’m not going to push myself to grow more. I’m focused on ensuring what I do on a daily basis is amazing and meaningful—I’m focused on leaving behind a legacy that my daughter would be proud to share with her grandchildren.

I think a lot about how my mother’s move to the US changed the entire future of our family. So I can’t help but wonder what amazing choices I can make that will continue to do that. If I have the power to shape an incredible future generation, I will do that. And I want to be present today, enjoying my life and my daughter’s life—not waiting for happiness in the form of monetary success.

I’m curious to know how much you’re balancing what you’re working on now and the activism that you’ve been involved with so long, and what it’s like being a part of both of those worlds, especially in the context of San Francisco.

After accepting a position in tech, I thought that I could still be an activist and a writer. But I realized that it was going to take a lot of my mental capacity and energy to adapt to startup culture and do my work really well. Although my personal work is always with me, I knew that I moved across the country for this amazing opportunity and I wanted to dedicate as much a possible to meeting my expectations. Prior to my move to San Francisco, I was presenting at different conferences and organizations across the countries and being asked to do a lot of consultant and advisory work. I had to start declining a lot of those opportunities. And I had to adjust to the realization that nobody in this sector knows me, which is different than Boston.

“Prior to my move to San Francisco, I was presenting at different conferences and organizations across the countries and being asked to do a lot of consultant and advisory work. I had to start declining a lot of those opportunities. And I had to adjust to the realization that nobody in this sector knows me, which is different than Boston.”

Outside of work, my only priority is being a really amazing mom. That can be challenging when you’re working in an environment where working moms aren’t the majority. The ways in which you use and prioritize your time is different and participating in after-hours anything is often a challenge, even though they’re usually necessary and important. Childcare is an obstacle when you’re a single mom in a state where you have no family and feel like you’re already spending too much time away from your kid.

How’s your daughter liking San Francisco?

She loves it but hates the hills. I hate it more than she does honestly but she likes it here a lot. Ha!

She’s really thoughtful and friendly so she made a new best friend within her first week in school. It’s been super easy for her in that way. And like I mentioned earlier, she’s now really interested in Science. Back in Boston, she participated in many different science clubs and programs. It helped expand what her understanding of science was and she became really excited about the opportunity for me to work in tech. And I’m glad she felt good about the choice because I hope she can face an obstacle one day and remember that, “My mom went through this too.” And we have deep conversations about girls in STEM and what it’s like to be a girl in a lot of the science programs. It was interesting to me that she wasn’t interested in the field because of the cool “perks” but because she sees this space as the space where she can do amazing things. Her mission is to promote eco-friendly lifestyles and find a cure for Alzheimer’s. After my grandmother passed from Alzheimer’s, she felt deeply connected and spent a year asking me countless questions. She knows we’ve created tech to do some amazing things and hopes she can do something amazing too. And I’m going to nurture her interest in science until she does exactly what she wants to do.

“I think a lot about tech’s impact on marginalized people, and not just how they use the service but how they actually can be included in the development of new tech.”

How do your friends and family from home feel about how far you’ve come and all you’ve accomplished?

They’re really happy for me. Actually, I had one friend who she really said, “Natasha I think you did everything you could here. You literally accomplished everything and there wasn’t a better next step than this.” My mom is really proud.

How you feel about the state of tech in 2016? What excites you, what frustrates you, what would you like to see change?

I think a lot about tech’s impact on marginalized people, and not just how they use the service but how they actually can be included in the development of new tech. This is where my previous experience overlaps with what tech is missing—the ability to always center the needs of the people they’re targeting. When we’re talking about young people, I’d love to see them getting the support and resources they need to turn their innovative ideas into reality.

“As a mother in tech, I also faced the reality that so many of the programs meant to nurture girls’ interest in STEM are not easily accessible. The programs are often replicating the very same systems that worked for people already in tech. I’ve found myself feeling like the burden falls on parents to fix the pipeline issue and get girls into STEM.”

As a mother in tech, I also faced the reality that so many of the programs meant to nurture girls’ interest in STEM are not easily accessible. The programs are often replicating the very same systems that worked for people already in tech. I’ve found myself feeling like the burden falls on parents to fix the pipeline issue and get girls into STEM.

One example is my daughter had science club on Saturday mornings, and it was at a college campus, which has its pros and its cons. The pro is that it’s great to send girls to a college to see what that environment is like. The con is that it’s often inaccessible for a lot of parents and families and it requires a lot of commuting. And then the classes are so short that parents, can’t just drop off their kids at the program and then go home or doing something else and then come back. They must sit there waiting. So parents are asked to spend a few hours every weekend getting their kids to this program, waiting for them, and then commuting back home. And that could be a barrier to some. The other barrier, of course, is a lot of these programs are really expensive, so if you’re creating programs that are supposed to improve diversity but they’re really expensive, only the people who make enough money to afford it it will be able to get their children into it. There’s usually a financial aid or scholarship application, but it puts the burden on parents who are now of low income to prove to the program that their children deserve a chance. Now you have moms and dads or grandparents, being asked to fill out applications that ask invasive questions about their finances.

“They’re asking parents who are already dealing with a lot to prove and to open up about these issues with people they don’t even know, so that their kid can have an opportunity that they deserve. What if parents don’t even speak English or what if they’re undocumented and don’t have tax documents proving they are of low income?”

They’re asking parents who are already dealing with a lot to prove and to open up about these issues with people they don’t even know, so that their kid can have an opportunity that they deserve. What if parents don’t even speak English or what if they’re undocumented and don’t have tax documents proving they are of low income?

This is probably related to gender diversity, but you wrote in your pre-interview that you think men should lean out.

Before I joined tech, the concept of “leaning in” surfaced onto my radar. Initially, it felt like this was being proposed as a new idea, something that’s rarely been done before. It frustrated me. I’ve spent most of my life leaning in for survival. And leaning in is simply what marginalized women across the nation have been doing for their basic human rights for decades.

“Before I joined tech, the concept of “leaning in” surfaced onto my radar. Initially, it felt like this was being proposed as a new idea, something that’s rarely been done before. It frustrated me. I’ve spent most of my life leaning in for survival. And leaning in is simply what marginalized women across the nation have been doing for their basic human rights for decades.”

And when I look at the core issue, it’s equity in the workforce. Women aren’t paid fairly, but women didn’t create the unfair ways in which women are compensated. And women of color make significantly less than white women, and face higher rates of discrimination at work. Women leaning in can help change the ways in which women are perceived and treated, but men leaning out create genuine opportunities for women to rise. Leaning out as a man can mean giving up your spot on an all male panel to offer a woman on your team the opportunity, or giving press ops to women, being vocal about the important roles women hold in the company, and of course, paying them a fair and equitable salary. Because the burden of making the workforce fair and equitable shouldn’t be ours to carry.

“Leaning out as a man can mean giving up your spot on an all male panel to offer a woman on your team the opportunity, or giving press ops to women, being vocal about the important roles women hold in the company, and of course, paying them a fair and equitable salary. Because the burden of making the workforce fair and equitable shouldn’t be ours to carry.”

What advice would you have for those of similar backgrounds hoping to get into tech?

We’re all facing different obstacles or adversities, and there are periods in our lives where we may feel like we can’t do what we want. And when we live in a negative environment, you’re not just internally facing challenges, but you’re getting that external negative validation. Whether you are a teen mom or a young person facing any of the many obstacles that make our lives unnecessarily harder than it needs to be, stay focused on your own dreams. Find a mentor or two who are smart and kind, and only trust them for advice and guidance.

And constantly work on yourself and making you the best version you can be. We like to believe that at some point in our lives we reach our full potential, but what if it’s a life long journey where we’re constantly learning and constantly changing and improving? Don’t feel like you have to be the final version of you at this very moment, just be willing to learn. Stay true to who you are and accept that you are a work in progress.

“Don’t feel like you have to be the final version of you at this very moment, just be willing to learn. Stay true to who you are and accept that you are a work in progress.”

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.”

I was born in Thailand in 1980 in a refugee camp near the border of Thailand and Cambodia. It was the aftermath of the Killing Fields where a million Cambodians died during the Khmer Rouge’s communist regime. My parents never talked much about that time, since it was so traumatic for them. And I don’t remember anything because I was so young. I do know that both of my parents lost their first spouses during that time.

“I was the poorest person in class, and one of the only Cambodians. At the time, I didn’t realize everyone else was actually pretty poor. But there was still a hierarchy even amongst the poorest of the poor. Like it was hard getting teased for wearing the wrong type of shoes or the same shirt several days in a row.”

My mom did tell me about how I had gotten pneumonia as a baby and almost died. She still has the X-rays. It was very, very hard for her, but she loves telling me that the early sickness boosted my immune system because I rarely got sick after that as a child. Too bad it didn’t last into my 30s. I get colds all the time now.

In 1984, we immigrated to the US as refugees as war. Our airfare was sponsored by a Mormon family, whom I don’t remember ever meeting, but it’s why we converted to Mormonism. We landed in Oakland and I’ve been in the Bay Area ever since.

You may not have super early memories but I’m curious to know what it was like arriving at the States for your family and what adjusting to life in Oakland was like?

My earliest memory is us living in cramped apartments around the Lake Merritt area with my grandmother and cousins. I went to a year-round school called Franklin Elementary, which was predominantly Asian. After the first grade, we moved to West Oakland, and I attended Hoover Elementary which was mostly African-American.

“It  felt completely normal to live together with eight or nine people in a tiny one bedroom apartment. It was really communal, and we survived on very little—24k a year of government assistance, which my mom miraculously made work somehow.”

In both settings, I felt like an outsider. I was the poorest person in class, and one of the only Cambodians. At the time, I didn’t realize everyone else was actually pretty poor. But there was still a hierarchy even amongst the poorest of the poor. Like it was hard getting teased for wearing the wrong type of shoes or the same shirt several days in a row.

My parents also didn’t speak English, so it was a constant struggle to switch between different cultures between home and school.

What did your family expect of you? What kind of pressure did they put on you to excel or be something when you grew up or that sort of thing?

My mom was particularly emphatic about education, and doing well in school. That was the top-most priority. She would always say, “You don’t need friends. They’ll just bring you down. Just focus on school.” I just assumed it was an Asian mom thing. But later, I learned she had an uncle who paid for her to attend school back in Cambodia. That experience must have made her acutely value education, because it’s not free in many countries.

“Food is interesting. People I meet love to say, “wow, you must have had delicious food growing up”, as if every meal was a dish from their favorite Thai restaurant. It’s always weird to be exoticized. What was normal for us was actually an extremely basic diet of rice with a small side of protein. McDonald’s and Chinese take-out was like the “fancy” treat for special occasions.”

With my dad, he was hands-off about education, but he cared a lot about appearances. He learned to be a barber in the refugee camps and was very meticulous about it. He cut my hair growing up until his hands failed him. He was also very particular with the shoes and clothes he bought for me, even when they came from The Goodwill. I have a fond memory of him saving up money so that he could get pants made by a tailor in Chinatown. It was really fun to see him pick fabrics. I definitely got my eye for design from him.

What aspects of growing up to you obviously felt normal at the time? Now that you’re in Silicon Valley you’re like, “Man. My upbringing was different than a lot of people’s here.”? What memories stick out to you?

I have a lot of siblings, six younger than me and one older half-sister. It  felt completely normal to live together with eight or nine people in a tiny one bedroom apartment. It was really communal, and we survived on very little—24k a year of government assistance, which my mom miraculously made work somehow.

Nowadays, I hear complaints about how small the apartments are in SF and how making 175k/year isn’t enough. I totally get that in this market, but everything is much more luxurious than what I grew up with.

Food is interesting. People I meet love to say, “wow, you must have had delicious food growing up”, as if every meal was a dish from their favorite Thai restaurant. It’s always weird to be exoticized. What was normal for us was actually an extremely basic diet of rice with a small side of protein. McDonald’s and Chinese take-out was like the “fancy” treat for special occasions.

I remember one of my first “American” meals. A woman from our church invited me to her brother’s family for dinner. Everything was so plentiful, and I remember this giant salad bowl, and I immediately asked. “Oh, there’s no rice?” That became a running joke every time I ate dinner there. I also remembering getting to high school and eating a bagel for the first time. I was like, “Whoa, delicious!”

It’s amazing to think back, because I’m such a foodie now and really enjoy the spectrum of food available in San Francisco. I hate bagels now, though.

Oh man. What were school years like for you? Did you have any technical inclinations or creative inclinations? When was that first developing for you?

In first grade, we had a computer lab, which I took to very naturally. Creatively, I was obsessed with origami and could make very intricate pieces. My mom thought it was an incredible waste of paper, so I would rip out endsheets in books and use that for folding.

In middle school, I took both art and computer classes. What was really cool, was that my art teacher was married to my computer teacher. Later when my art teacher, Ms. James, found out that I’d become a designer, she was thrilled.

Walk me through those later years of school and then eventually getting into college.

High school was awesome. Many people talk about their high school years as the most horrible time in their lives, and I actually had a really wonderful time. I went to Oakland Technical High School—which I had to work really hard to enroll in, because it wasn’t my assigned school.

I had a great education because I was equally exposed to the sciences, liberal arts, and creative arts. I was in a Magnet program called the Health & Biosciences Academy, as well as a humanities program called Paideia, which was taught using the Socratic method. Both of those programs really taught me to think critically and very deeply about the world.

“I started studying for the SAT’s when I was in the seventh grade because I was just like, ‘If I don’t go to college, then I’m never leaving the ghetto.’ I had this great fear of being in a cycle of poverty that I saw my peers get trapped in.”

At the same time, I was also really involved in the journalism program. I was co-Editor-in-Chief of the school newspaper, which is where a lot of my inspiration to become a designer came from. We were designing the newspaper by hand, actually cutting out printed columns and doing paste-ups for the printers. I also worked on our high school’s first video yearbook, which introduced me to Adobe products for the first time.

Was college something you thought that was possible for you financially? Or like as a kid, did you think it was basically possible?

I always believed it was possible. I had both incredible faith and anxiety around it. I started studying for the SAT’s when I was in the seventh grade because I was just like, “If I don’t go to college, then I’m never leaving the ghetto.” I had this great fear of being in a cycle of poverty that I saw my peers get trapped in.

I didn’t worry too much about the financial aspect of it, because I was pretty aware of loans, scholarships, and grants. If I had worried too much about the finances, I think I would have been paralyzed to act.

In the last couple of years of high school, my grades ended up being really shitty, so I didn’t apply to the Ivies or UC’s like most of my Paideia classmates. I had been too focused on everything else that interested me non-academically: helping to run the school newspaper, starting a gay-straight alliance, leading our high school’s Sierra Club program, learning radio journalism at Youth Radio, and performing in plays and dances. And, at the same time, I was trying to come to terms with being both gay and Mormon. It was a lot, and my grades got pretty shot. In the end, I knew I wanted to do design and applied to just one school, the California College of Arts and Crafts. It’s now just called California College of the Arts. I was relieved when I was accepted, and I remember telling my best friend, Ben, “My future’s going to be okay now.”

At that point, did you have any idea that you’d end up working in Silicon Valley. Was that on your radar?

I don’t think so actually. The dotcom boom was still nascent when I entered college, and I was very interested in motion graphics because of the work I did on my high school’s video yearbook. Of course, the dotcom boom reached its peak quickly after I started school. CCA was mostly print-based, but a professor named David Karam started a program called New Media, which I quickly enrolled in. It was a mix of motion graphics, information design, programming, and interaction design. I fell in love with the classes and knew I wanted to work on very technical, internet-related projects.

What was going to art school like after coming from a big high school in Oakland?

I’d been exposed to so many different cultures and types of people early on in life—Asians around Lake Merritt, African Americans in West Oakland, and wealthy white Mormons in the Oakland hills and beyond—that adapting to art school was relatively fluid. You just learned to weave in and out of different groups.

On the other hand, I felt a lot of otherness. I met so many kids that came from an enormous amount of wealth and privilege, who weren’t serious at all. They didn’t know what they wanted to do and had parents who funded their experiment with art school. The majority of students truly wanted to be artists or designers and they were very serious about it, but others were just there to play.

Walk me through your tech career. What happened from there?

In college, I got a really awesome internship at a company called Move Design. It was started by two former IDEO designers, Peter Spreenberg and Samuel Lising. My friends, Dain and Kim, were also working there, so we just did a range of fun, interactive projects. I learned ActionScript, Lingo, JavaScript, PHP, and Perl during that time. That’s what really got me super excited about the internet, programming, and interaction design.

When the boom went bust, I went to work for Youth Radio in Berkeley as a teacher and designer.

After that, I was hired as an intern by Conor Mangat at MetaDesign, which is one of the top branding agencies in the world. The San Francisco office had been started by a favorite professor of mine, Terry Irwin, along with Erik Spiekermann and Bill Hill. I was lucky to get that job because it was the nadir of the dotcom bust. The San Francisco office had just downsized from over 100 people to less than 10, so I’m very grateful to Conor for believing in me early on.

“I joined the Gmail team. When I started, there was only one other full-time designer on Gmail. The way we ended up splitting it, was that my colleague, Jason Cornwell, worked on desktop, and I worked on mobile. It was just really cool to have that much responsibility and impact. Mobile Gmail was supposed to be my 20% project, but that quickly became my 120% project.”

My work at MetaDesign was mostly visual design for brands and websites, but eventually, I wanted to branch out into UX. I was really inspired by Hugh Dubberly, a former design manager at Apple who’s ridiculously smart and knowledgeable about design history and theory. He eventually became my mentor and hired me at his studio, Dubberly Design Office. I was super happy working there and stayed for 5 years.

One day a sourcer from Google emailed me out of the blue. I remembered when I was at MetaDesign, a recruiter from Apple had contacted me. I blew it off and later regretted it. So this time around, I decided to follow up on the email, even though I was very happy at Dubberly.

I had a few phone conversations with Google, then went down for a day of interviews. I was so impressed with everyone I talked to, and the opportunity for learning was so huge, that I decided join. It was an amazing experience, though when I first joined, I felt like I didn’t really belong there.

“It’s a big psychological shift to be a founder. Our employees depend on us to feed their families and themselves. They depend on us for helping them grow professionally and personally. I take it much more seriously because of that responsibility. It’s not a hobby. It’s a real business where the success or failure of the company has huge impacts on everyone.”

Expand on that.

I just felt like everyone was so much smarter or so much more accomplished. During orientation, they were like, “Oh, here’s some amazing people that work here.” They profile all these ridiculously-accomplished people. I’m like, “Uhh. What? Why am I even here?” Eventually you get over that a little bit, partly because you talk to other people who say, “Oh yeah, I felt the same way.” Later on, I read about impostor syndrome which describes this phenomenon.

What did you work on while at Google?

I joined the Gmail team. When I started, there was only one other full-time designer on Gmail. The way we ended up splitting it, was that my colleague, Jason Cornwell, worked on desktop, and I worked on mobile. It was just really cool to have that much responsibility and impact. Mobile Gmail was supposed to be my 20% project, but that quickly became my 120% project. Now the Gmail team is huge and it’s really awesome.

So crazy. What has it been like transitioning from a tech employee to tech-founder?

It’s definitely very different. There’s a lot more responsibility because of who is dependent on you. At Google, I was an individual contributor, and even though I had a lot of impact, no one was dependent on me for their own livelihood. It’s a big psychological shift to be a founder. Our employees depend on us to feed their families and themselves. They depend on us for helping them grow professionally and personally. I take it much more seriously because of that responsibility. It’s not a hobby. It’s a real business where the success or failure of the company has huge impacts on everyone.

What are some of the struggles and roadblocks that you’ve had to overcome both as employee and entrepreneur?

My biggest struggle is social anxiety, which progressively got worse as I got older. There were times when I would have panic attacks in public streets or just walking into a room. It was a huge barrier to becoming a leader. That probably held me back a little bit, actually probably a lot, at Google. I overcame it when I stumbled on a research program at Stanford that was comparing methodologies for treating social anxiety. I was accepted into the study, and went through 12 weeks of treatment and cognitive behavioral therapy. It worked, and it’s much less of a problem now, even though it’s always there.

“My biggest struggle is social anxiety, which progressively got worse as I got older. There were times when I would have panic attacks in public streets or just walking into a room. It was a huge barrier to becoming a leader.”

Awhile back, I read about how Nightmare on Elm Street was inspired by Cambodian trauma survivors who died in their sleep from nightmares. And I later read about how trauma, especially amongst survivors of genocide like Cambodians, can be passed down biologically to their children. It really helped explain why depression, stress, and anxiety is so prominent in my family, so it’s something I continuously watch out for in myself and my family.

What has working in tech been like knowing that you don’t have any financial network or safety net?

It’s hard and it’s fragile. I talk to a lot of other entrepreneurs who have families they can fall back on if they fail. And if their families aren’t wealthy by income, they own property and have accumulated value, so they still have another plan B. Many other entrepreneurs also have fewer financial obligations, meaning they don’t have to support their siblings, parents, or extended family. I get that everyone struggles. But clearly, some struggle more than others. A lot of people take for granted the network and privilege they have, and they don’t realize how incredibly lucky they are. For me, it’s always precarious. I’m on a founder’s salary, which is less than half of what I was making at Google, and I still need to support family members as well as myself. It’s very tough when you don’t have much of a plan B, but it makes me more driven to make the business succeed.

“I talk to a lot of other entrepreneurs who have families they can fall back on if they fail. And if their families aren’t wealthy by income, they own property and have accumulated value, so they still have another plan B. Many other entrepreneurs also have fewer financial obligations, meaning they don’t have to support their siblings, parents, or extended family. I get that everyone struggles. But clearly, some struggle more than others. A lot of people take for granted the network and privilege they have, and they don’t realize how incredibly lucky they are.”

Yeah. I feel you. Do you ever feel isolation in the industry? For me personally, when I worked in tech, I felt a sense of otherness and isolation a lot. Not from being a white chick, there are plenty of white chicks—but socioeconomically. I came from a small town, went to public state school, moved here with no money, also did not have a financial support network. I just never met anyone that I could really relate to. I’m curious if you ended up feeling those senses of isolation during your career? Just based on being different?

Yes absolutely.

At Google, I remember sitting at work and overhearing a conversation where someone said, “Oh yeah, I have a couple of houses and my partner has a house too, but it’s just too hard to manage.” She was literally complaining about having multiple houses, and I was just like, “Wow, what world is this?” It was definitely not a world I came from.

When you come from poverty and you’re also gay, Cambodian, Mormon, and a refugee of war, there’s always an inherent isolation. Of not fitting in anywhere. Of not knowing anyone else like you. Until my 20s, I was even stateless, and couldn’t get a passport from any country. So I felt a very deep sense of isolation. You have to cherish your own uniqueness, but you also have to learn how to adapt in order to survive. It’s exhausting.

Let’s get more into identity. What is your experience been as a gay man on top of everything else? I’m especially curious about being gay in the context of being Mormon.

That was really tough for me, because I was very religious in high school and earlier. I was a Boy Scout, I went to Mormon summer camps in Utah, and I planned to go on a mission. I tried very hard to be the perfect Mormon boy. And it took me a really, really long time to reconcile that. When you have this belief system that doesn’t include you, you have to figure out how you fit in or not. Eventually, I realized I didn’t fit in, and I became a much healthier person afterwards because I didn’t hate myself. In San Francisco, we still have some diversity left, so I don’t really feel too separate in terms of the gay facet of my identity. I feel lucky about that.

“When you come from poverty and you’re also gay, Cambodian, Mormon, and a refugee of war, there’s always an inherent isolation. Of not fitting in anywhere. Of not knowing anyone else like you. Until my 20s, I was even stateless, and couldn’t get a passport from any country. So I felt a very deep sense of isolation. You have to cherish your own uniqueness, but you also have to learn how to adapt in order to survive. It’s exhausting.”

On the flip side, I don’t know how active you are socially in the gay community, but what is it like being a techie in the gay community? Total other side of the coin.

Ah, this is an interesting topic. What’s sad is the mainstreaming of gay culture. I talked about this recently with my partner, Harold. When I was growing up, being gay was synonymous with being rebellious and iconoclastic. You were expected to be different. It was still taboo, but it afforded you a great amount of freedom and space to express yourself.

The world has made a lot of progress in acceptance of gay people, but a side effect is that assimilation has happened. Gay folks are in the mainstream, but they fit into what is acceptable. In media, they’re usually normalized into caricatures of what’s expected: wealthy white men who fun, attractive, and inoffensive. Yet there’s a full spectrum of people who still aren’t represented—there’s poor gay people, there’s gay people of color, there’s lesbians, there’s trans, there’s gender non-conformists, there’s gay people who are angry, and there’s people who have sex with the same gender but aren’t “gay.” So I’m saddened by the mainstreaming of gay culture, because I wish we had a greater representation of difference and all of the in-between states.

Most sad of all, is how mainstream San Francisco has become. One of my best friends, Sean, moved to the East Bay recently, and he was like, “Yeah, I wondered where all the people with the weird haircuts went. They’re all here in the East Bay!”

My next question, which we’re already touching on—what’s it like being both a techie and local?

In some ways, it’s really fun because I feel like I’m getting to do what I love in the place I grew up in. But, San Francisco has changed a lot. Oakland is changing even more. Many things have been lost because of how much tech has transformed the area. I miss that.

I’m in a rent-controlled apartment in San Francisco, and I can’t actually afford to move back to Oakland. It’s just really crazy because I spent all this time trying to escape Oakland, and then I can’t actually afford to go back. It’s very ironic. I touched on it a little bit when my friend made the comment about haircuts in the East Bay—San Francisco just isn’t as diverse as it once was. It’s very homogenous, and that’s increasingly getting harder for me to accept. It’s heartbreaking.

“I’m in a rent-controlled apartment in San Francisco, and I can’t actually afford to move back to Oakland. It’s just really crazy because I spent all this time trying to escape Oakland, and then I can’t actually afford to go back. It’s very ironic.”

I used to think I’d live in San Francisco for the rest of my life because it’s just so open, diverse, and you can live how you want to live. But when toast is $5 dollars, it’s kinda crazy. I actually love the $5 toast, but when that’s the norm, and there is not much deviation, it’s obscene.

Can you expand on what’s been lost?

My partner is much more conscious about social justice, diversity, and oppression. He’s definitely made me more attuned to those issues. For example, the queer arts in San Francisco is dying because it’s getting pushed out by rising rent prices, evictions, and a lack of studio spaces.

My techie side says, “Oh, well. It just means, as an artist, you have to adapt, and try to figure out who the audience is and cater to your audience”. The other side of me is like, “Wow. That’s a really shitty thing to say. These are people that have a particular point of view and a particular statement they want to make, and you’re telling them they need to suppress that?”

The fact is, their way of expression is being taken away from them. I have to constantly ask myself, “Am I part of the problem or am I not?” It’s very, very complicated and I’m not sure what the answer is.

How do your friends and family from growing up feel about how you turned out?

I think they’re all super excited for me. My mom still doesn’t really know what I do. She doesn’t have an understanding of technology but my siblings do. And I feel good in that I can set an example. I wish I could write an autobiography that was like, “I grew up poor, then bootstrapped myself, and did it all by myself,” but the reality is that I had a lot of help and people who believed in me. I had mentors, I had family that watched out for me, I had amazing teachers. I feel like it was definitely like a group effort, and so, I hope I continue being a good example for others. More importantly, I strive to help others in the same way others have supported me.

What would you say are your biggest motivators? What drives you?

Well, I had this experience growing up where I had to do a lot of translation and filling out of forms for my mother who didn’t speak English. That made me aware of things that may be invisible to others, like the design of forms, for example. So there’s a notion of service design that I get really interested in. How do you help others accomplish what they need to get done to survive or excel? Answering that question is a huge motivation for me. It’s partly why I started Mixmax with my friends, Olof and Brad. I wanted to make something that would actually help people do their own work better in order to succeed.

My life with my family and partner is also a major motivator for me. I’m driven to help support them. I believe when you succeed in your personal life, you also succeed in your professional life. It’s not about “balancing” work and life, but about creating flexibility in each so that both areas can succeed.

Let’s go macro for a second. How do you feel about the state of tech in 2016? What excites you, what frustrates you?

I’m extremely excited about software for professionals. It’s so cool to see how people use existing pro tools for their work. The current tools are really, really awful. It’s just amazing to me how much we focus on consumer products, but there’s this world of professional software that needs great design. So it’s very exciting to think about those possibilities.

What’s frustrating? Everyone is so entitled. It’s definitely a bubble in the Bay Area where people feel like they deserve the world, because they happen to be an in-demand tech person living here. Super, super frustrating. It’s refreshing to talk to people outside Silicon Valley, who are also hungry to learn and grow, but have a lot less entitlement.

“Always ask yourself, ‘How can I exceed expectations?’ Set explicit goals and push yourself to achieve more than what was previously asked of you.”

Lastly, what advice would you give to folks from similar backgrounds to you who are really interested in tech but just not quite sure how to get into it and succeed?

Gosh, let’s see. Well, one tip is to don’t be afraid to approach the people you admire and recruit them as mentors. You might be hesitant to reach out to people, because you think they’ll flat out reject you. For the most part, I have found that many people are willing to help and are awesome about it.

Another tip: always ask yourself, “How can I exceed expectations?” Set explicit goals and push yourself to achieve more than what was previously asked of you. I learned this from Google and from my time at Dubberly. Hugh phrased it as “pulling a rabbit out of a hat.” Overachievement increases the chances for success and learning.

My last advice is to foster a wide variety of interests that make you happy. Tech might not be what fulfills you in the end, so consider other things that could also make you happy, and at the same time, viable as a living. Even within tech, there are many hats to wear, many subjects to explore, and many products to design. It’s super open.

I grew up outside D.C in Virginia, a super nerdy kid.

What part of Virginia?

I come from Fairfax County, just south of D.C. It’s a pretty affluent area, but very diverse. I’ve realized in retrospect that it’s really out there in terms of median income, but actually has a lot of diverse immigrant populations. People are drawn towards working in D.C. Not a bad place to grow up, I would say. But it’s way more interesting with context about what the rest of the world is like—realizing how affluent and diverse the area is.

“I went to University of Virginia for undergrad and felt very out of place, and so I buried myself in more and more work. I got a double major and a masters in four years.”

Interesting. So, you were a nerdy kid. Did you feel that you were technically inclined early on?

I would say I was technically inclined. My parents were really supportive of my education. Even in elementary school, I was going to a local high school to take math classes and classes in Computer Science. I drew away from technical work for a while when I didn’t see there was creative work there, but now that I’ve come back to it it feels like a nerdy home for me.

Walk me through those early education years,going to college, and then eventually making your way all the way across the country.

I went to University of Virginia for undergrad and felt very out of place, and so I buried myself in more and more work. I got a double major and a masters in four years. I very much identified with being a great student. So at the end of my undergrad, I went straight into graduate school doing research. I got into MIT for a PHD program.

MIT was great for me in a lot of ways. MIT is such a hot bed of engineering creativity in a way that I hadn’t experienced before. UVA was very focused on business and their law school, so I hadn’t seen that engineering could be for things besides a well paying job. MIT has people programming LED everything for fun, building roller coasters out of plywood: things that I found very inspirational. And at the same time I was seeing creativity in engineering, I found that even though my graduate work was very interesting technically, it wasn’t drawing my attention. It didn’t have an immediate impact on the world.

Over time I realized that maybe I could be happier if I was doing something else. So I tried a software engineering internship. It wasn’t quite the place for me, but I realized I thought I could be happy doing software engineering somewhere else. After that, I ended up finding my current job, dropping out of grad school, and moving to San Francisco.

What were your first impressions of Silicon Valley? What were you expecting? How did it live up to – or not live up to – what you had thought it would be?

I’d had an internship at Berkeley one summer when I was 21. I stayed in a dorm at Berkeley, but was way shyer then. I was like: “Oh my gosh, this is the promised land. There are so many cool people walking around. If only I wasn’t too shy to talk to everyone I would be so happy and feel so at place here.”

“Just to be in a city where I didn’t feel weird was so liberating.”

And my move to San Francisco was just so dominated by becoming way more comfortable with myself. And in particular, at this sense of weirdness that I don’t think is necessarily caused by being queer, but that is very correlated for me. Just to be in a city where I didn’t feel weird was so liberating. So my first year here, I was happy just to party and explore in a way most people felt comfortable enough to do in college. I had fun!

But at that point, I didn’t quite get cultural context on a lot of things. Criticisms of privilege in tech weren’t on my radar at that point, or cultural critiques of privilege in the city. I was just thinking about how it was a fun party, and touching that for the first time. Just trying to find my place at that point.

“I felt very much like even a technical outsider, especially as the first inexperienced coder at my company. And that challenge concentrated me. I focused for eight hours a day in such an intense way I didn’t listen to music, didn’t look at my cell phone at all.”

Workwise, even though I had a technical background and plenty of CS classes, I hadn’t had as much experience coding as many people who work at top jobs here. I was very prepared in some ways and not quite totally prepared in others. I felt very much like even a technical outsider, especially as the first inexperienced coder at my company. And that challenge concentrated me. I focused for eight hours a day in such an intense way I didn’t listen to music, didn’t look at my cell phone at all.

Totally. I can so relate on the weird thing. I’m from North Carolina, like super close to where you’re from. People use the word weird all the time in North Carolina just to denote anything. Like, “Oh, that meal is weird,” or like, “That outfit is weird.” Weird is used all the time. Then I came here and I was like, “Oh my God. Nothing’s weird and everything’s weird at the same time.” That word doesn’t even work here. It was just so cool to suddenly—I was weird in North Carolina because I’m pale and wore black too much, things that are super normal here or in New York or whatever. Being intellectual. All of that was weird. Here it’s like, there is no such thing as weird anymore and that is the most amazing feeling.

God bless SF.

Seriously. So walk me through your experience working in tech so far. What is exciting to you about your work?

I’d coded before, but hadn’t thought about code as a means of communication. Basically, I was missing an appreciation of software engineering. Software engineering asks questions like “How do you write code that is easily understandable by other people?”, and “How do you write in a way that’s resilient to a bunch of unknown changes in the future?” Good software engineering is thoughtful, compassionate, and thorough.

Unlike most kinds of engineering, changing code means you can change your product every single day – so things can happen very quickly. It’s such a collaborative media, because software engineers are all collaboratively writing a huge document of code together. There’s a lot of coordination there that I find really interesting. And on top of that, I really appreciate making something, a product, that I use everyday and that people use everyday to make their lives better. For me, it’s just the right way to merge technical work with thoughtfulness about other people.

“I’d coded before, but hadn’t thought about code as a means of communication. Basically, I was missing an appreciation of software engineering. Software engineering asks questions like “How do you write code that is easily understandable by other people?”, and “How do you write in a way that’s resilient to a bunch of unknown changes in the future?” Good software engineering is thoughtful, compassionate, and thorough.”

Plus I’m starting now to be a manager, and that’s perfect for me. It’s combining mentorship, and talking people through their feelings in a way that I don’t think they often get to do inside of tech. That’s such a special combination of things that I have. So many of my one-on-ones are long walks up Potrero with cherry trees are magnolia trees, and that’s such a nice balance to writing software.

What have been some struggles for you ? For instance, you mentioned in your preinterview the flipside of being a badass queer woman in tech. Expand on that for me.

Sure. I got feedback from my manager that the way I presented myself didn’t always come across as technical and professional. And in some ways that was definitely true. We have an open bar at the office and I would be sipping scotch at 3 P.M. But, also, hearing that as queer woman, I couldn’t help but react as, “Yeah, of course I don’t look and act like straight white dudes.” Not that I don’t like the white dudes that I work with, but that feedback hit me in a way that made me cry. With work though, I came around to realizing that it’s no one’s job to make anyone feel welcome, and that’s not the purpose of the company. But now I’ve come around to the flipside of that — that there’s a business case for making sure that everyone feels included in the company. I had to go through all those emotional cycles of  — no one has to take care of me, but also I hope there are businesses out there that do recognize me.

“There’s a business case for making sure that everyone feels included in the company.”

And I do feel recognized by my company. I’ve gotten promotions, I’ve gotten to start managing, things like that. But I still often have feelings like, “I don’t look like tech,” or, “Is it cool enough to work in tech?” For myself, I often wonder, am I working with people that most directly bring out my best? I think working inside tech as a queer woman is a beautiful place to enact some kinds of change. I’m one of the most vocal advocate for diversity inside my company. But no one’s encouraging me on to do that, and so I wonder, am I growing the social responsibility parts of myself? In my current job, I’m definitely growing some emotional parts of myself, I’m definitely growing the technical parts of myself, but I don’t have direct role models for social responsibility in a way that I do think is very important in life.

Yeah, for sure. You don’t want to feel that your actions are in a silo.

Yeah. I’m changing my company for the better, but how important is it that any specific tech company gets better? I’m starting to speak at external events, but I don’t know if I’m changing things. Certainly, it makes me feel like more complete of a person if I have a chance to speak what I think is socially righteous. But I have to wonder – is this effective? And who is asking me if this is effective? Who is caring?

“Sometimes, it’s lonely. Other people don’t talk about diversity as much as I do—probably because they don’t have feel the lack of it in their core. So I try to translate my feelings into, ‘What is the business case for us?’ in a way that’s indisputably worth pursuing.”

My company is supportive. I just wrote a piece on diversity that we published on our company blog. And I’m so proud that we’re willing to do that. I do try to put diversity conversations into language that I think is approachable for people of privilege, and appreciate my company’s support as I’ve grown into being able to make that switch of language, from anger to something productive.

I want to get into privilege for a second. What is it like for you kind of straddling multiple worlds, some of which are privileged such as tech, and some of which aren’t as much, like being a woman and being queer?

I think about  privilege so much more than most of tech. I guess that happens anytime there are marginalized groups. Sometimes, it’s lonely. Other people don’t talk about diversity as much as I do– probably because they don’t have feel the lack of it in their core. So I try to translate my feelings into,”What is the business case for us?” in a way that’s indisputably worth pursuing.

“There is a radicalness to being a queer woman in a group of privilege, just being in tech myself. It’s kind of radical that I’m working here, and surviving, and thriving.”

It’s really easy to forget my duality in either context. When I met my girlfriend, she was working with homeless women a few blocks from my office. Dating her, I’ve gotten to feel and learn about both “tech sucks, it has so much privilege and it doesn’t talk about its privilege,” and, “Wait, there’s some surprising positive things in tech.” She’s so political, I don’t think she ever would have guessed that she would date someone in tech. But then also—there is a radicalness to being a queer woman in a group of privilege, just being in tech myself. It’s kind of radical that I’m working here, and surviving, and thriving.

A lot of times in queer communities, I do often feel out of place for working in a field of such privilege, but I do feel proud of that as long as I’m thinking about what social justice means there. So there’s nuance. Yes, I work in tech, but I’m trying to live that authentically and consciously.

Where have you found your support networks here?

My manager at Asana talks to me about everything through the lens of feelings, which is how I like to communicate. I appreciate mentorship from someone who is so multilingual: it’s rare to be able to talk about both feelings and technical work. A lot of my support has been external to work, because I need acknowledgement that it is work to be diverse and there are feelings that go along with that—and that’s not a conversation that happens much inside such a non-diverse field. My biggest support over the last few years, and someone who’s really increased my language around privilege in tech, is my girlfriend—she’s wonderful. And I do have to call out both of my parents as well.

“It’s rare to be able to talk about both feelings and technical work.”

Have there been any specific mentors or people that have been super pivotal in your career?

My manager has been very encouraging, though I haven’t worked with him directly on a team. But a lot of the growth that I’ve done is towards being able to run solo and having confidence in that. I’ve internalized over the last couple of years when you work inside a company, someone is deciding what work you’re doing. And definitely it is very liberating to have your own strong opinions about what I should be working on. I’ve been supported into having my own opinions and helping direct my own work, and also have input into what my team should be working on and how we work together. Inside most tech companies there’s less hierarchy and more making sure that lots of people are empowered. That’s been very positive for me.

What is important to you in a job now versus the beginning?

When I was applying for my first job from the East Coast, it was so hard to tell what companies were looking for, or to evaluate all the promises companies made. And so I just ended up working at the place I felt most emotionally comfortable. I loved that their job posting included not just technical requirements, but also their company values as well. I was really excited at the prospect of a job that was going to appreciate me for more than just my technical skills. Now that I’ve been in Silicon Valley for a few years, I recognize the nuance of how business models influence what you’re actually working on, of how specific engineering practices relate to your day-to-day, and how much time you have to spend fixing old issues as opposed to working on new features.

“I want white dudes to notice when they’re in rooms of all white dudes, and to acknowledge that it’s an issue.I’ve been in meetings that were 17 men and me. And I was so distracted the whole time. I kept going around and counting how many men were in the meeting with me because I just felt it so much. I really appreciated afterwards someone came up to me afterwards and said, ‘Did you notice you were the only woman in that meeting? That was weird.'”

And now I’m even more appreciative of being recognized as a whole person. I can imagine myself stuck at another company just typing code. At my current job, I’m appreciated for my emotional skills through management, I’m appreciated for my opinions about how products should be formed. That’s let me grow into a more well-rounded career, and let me pick my passions. It’s given the space for me to advocate strongly for diversity work and be a part of the process too. I’ve been part of the process as my company recognized diversity and inclusion work is a full time job, and as we hired someone into that roll, and I still feel listened to for my input.

Let’s talk more about your opinions on that—like what do you think tech could be doing better right now to be more accommodating to diversity?

The biggest thing is not only acknowledging how un-diverse tech is, but acknowledging in the day to day that that’s an issue, and believing it’s worth fixing. I want white dudes to notice when they’re in rooms of all white dudes, and to acknowledge that it’s an issue. Even though I work at an extremely thoughtful company—our numbers aren’t great. My engineering team is 9% women, let alone queerness, let alone groups I’m not even parts of, that I’m uncomfortable that we’re missing.

“I’m looking for humility from tech, stating that we own and acknowledge the lack of diversity is a problem and it’s our problem, or even just showing more complex understanding of the fact that they’re part of an issue. It makes me so pissed every time I hear someone say it’s a pipeline issue. Especially when you look at how many people are graduating with degrees from college with computer science degrees, and Silicon Valley is nowhere near as diverse as that. So you can talk about a pipeline issue, but that is not acknowledging your own flaws. I think that a first step is at least recognizing and validating the experience of the people that are out there.”

I’ve been in meetings that were 17 men and me. And I was so distracted the whole time. I kept going around and counting how many men were in the meeting with me because I just felt it so much. I really appreciated afterwards someone came up to me afterwards and said, “Did you notice you were the only woman in that meeting? That was weird.”

I’m looking for humility from tech, stating that we own and acknowledge the lack of diversity is a problem and it’s our problem, or even just showing more complex understanding of the fact that they’re part of an issue. It makes me so pissed every time I hear someone say it’s a pipeline issue. Especially when you look at how many people are graduating with degrees from college with computer science degrees, and Silicon Valley is nowhere near as diverse as that. So you can talk about a pipeline issue, but that is not acknowledging your own flaws. I think that a first step is at least recognizing and validating the experience of the people that are out there.

At a high level, how do you feel about the state of tech in 2016. What really excites you and what frustrates you?

There’s lots exciting about tech. I’m personally excited about tech in enterprise, which is creating things quickly as applied to how people do productive things. I appreciate getting to make something of value that’s such a core part of people’s workflows.

“Tech has so much potential, I think it’s worth being frustrated about because I love it and I think we could be doing better.”

What pisses me off the most is lack of acknowledgement of privilege and what that means. And that’s nothing new—there have always been so many industries with money who don’t recognize that. Tech has so much potential, I think it’s worth being frustrated about because I love it and I think we could be doing better.

How do you think your background and life experience impact the way that you approach your work?

My queerness has made me so emotional, and I think there’s so much room for emotional coders. It definitely makes me think about communication way more deeply. And that applies even more clearly to management than technical work. There is lots of room for emotional coaching in encouraging people to grow into responsibility, and I do that.

My best job before software engineering was as a summer camp counselor, and it’s just so funny how parallel some of those experiences are, in trying to find and share joy, and embarking on this huge collaborative journey together, whatever it is.

“My queerness has made me so emotional, and I think there’s so much room for emotional coders. It definitely makes me think about communication way more deeply.”

What are you working on right now, this year, either for work or for yourself?

I’ll say, this year, for myself, I’m working on making a stable, beautiful adult home life, starting to have gardens and making kombucha, trying to figure out long term purposes. I’m growing into a mature person in this city. It’s not brand new for me anymore!

My last question for you would be what advice would you have for folks from similar backgrounds or facing similar struggles, hoping to get into tech?

Work your network or work whatever is closest to your network. I have such a soft spot for people that I connect with emotionally, and talking them through application processes, whether it’s my company or even somewhere else. There are people who resonate with you, and it will bring them joy to help you find a job that’s going to make you happy. Like, if I’m going to be a marginalized person in tech, then part of my purpose is to help my kind, so if it’s not me I’m sure they can find someone.

Especially, traditional networking made me very uncomfortable in lots of ways, like feeling very insincere. And I think a lot of that didn’t seem my type, or my type of small talk even. But there are people out there—there are companies out there that are going to value your full personality. There’s enough jobs in tech that you can find one that is right for you, that accepts you, that is excited by you.

“There are people out there—there are companies out there that are going to value your full personality. There’s enough jobs in tech that you can find one that is right for you, that accepts you, that is excited by you.”

Full disclosure: I basically have handlers who will make sure I don’t say anything too off-color. But generally, the only things I avoid saying are partisan things because I run a non-partisan organization. Talking about being a woman in technology, or a gay woman in technology in San Francisco, is not partisan.

Or a “loud-mouth lady gay,” as you called yourself in your application?

Yeah. Being a loud-mouth lady gay led to me realizing that, “Oh my God, I’m no longer suited to work for other people.” The last boss I ever had said that she thought I would do much better working by myself. She was correct.

Okay. So let’s start from the beginning, Tell me a bit about your early years and where you come from.

I am from Brooklyn. I’m a fifth generation Brooklynite. My family has been there since 1890 on the maternal side and since 1910 or so on the paternal side. So we’re pretty run-of-the-mill Eastern European Jews who left Europe when Europe became less-hospitable. I’m from the part of the Brooklyn where the accent is from and where hipsters still don’t live. So when you think artisanal crafts, do not think of the Brooklyn that I grew up in or the Brooklyn that my mother currently lives in. My mother would have no idea by what you meant by “artisanal soap,” “artisanal candles,” “artisanal gefilte fish.” She just wouldn’t know what any of that means.

I respect that. What part?

Bensonhurst.

Bensonhurst, I do not know Bensonhurst.

Bensonhurst is where the “Honeymooners” took place, where “Welcome Back, Kotter” took place, and where “Saturday Night Fever” took place.

Wow, that’s really amazing. No, you don’t have an accent, but you have the East coast swagger, which I appreciate as a fellow-East coaster.

Thank you.

When did you first get interested in tech, and separately, when did you become interested in politics?

Those actually overlap a bit. I’m older than I look, so the first time that I used the internet was my first week of college. This was 1995 and I was definitely an early adopter. I was one of the first people in my circle to learn HTML, and I took some entry level design courses in college.

I first became strongly interested in politics the night of the 2000 Presidential election. I was with a group of friends in North Hampton, Massachusetts, and we were watching the returns. When Florida went blue my friends were like, “Okay, great, Gore’s president,” and went to sleep. I was like, “I’m just going to stay awake and watch the rest of the returns.” This meant I was awake and alone when Florida was suddenly red.

“Being a loud-mouth lady gay led to me realizing that, ‘Oh my God, I’m no longer suited to work for other people.’ The last boss I ever had said that she thought I would do much better working by myself. She was correct.”

Keep in mind it was the middle of the night in Florida when this happened. First the state was declared for Gore and then — what was the story? — they found a truck filled with ballots for the Republican candidate, George W. Bush. This was a very surprising thing to happen in the middle of the night, and a very surprising thing to happen in what was an overwhelmingly Jewish section of Florida. And then the recount dragged on forever and wound up at the Supreme Court.

I think that night was the first time I became cognizant of how important voter turnout is. The presidential election should never come down to multiple recounts of ballots in a single county in America. At the same time, I was young and doing other things with my life. In 2004, I decided it was time to get more involved in politics. I met Sharif, a man who was staring a project called Swing the State. People would register as volunteer online with Swing the State, and Sharif would help them travel into swing states to do voter registration and get out the vote work. I told Sharif I wanted to help, and that was that. I was somewhat technical at that point, and this was a highly technical project. It was really just Swing the State and MoveOn.org that were organizing volunteers online and then deploying them on the ground back then. Swing the State was my first political tech project. I just kept going from there.

So, at first, you were working in tech, and politics was a hobby?

No, actually, I was investigating police misconduct for the City of New York.

Okay, walk me through this whole thing. I’m going to stop talking. You take me from the beginning.

My career path makes absolutely no sense. Let’s set the stage. It’s 2000 and I lived in Western Mass, because that’s where I thought young lesbians lived. In 2001, I came to my senses and moved back to New York, because it turned out that Western Mass is actually where middle-aged lesbians live. So, I moved back to New York, and puttered around for a bit. In 2004 I got a job investigating police misconduct for the City of New York. This was an awesome job: I had a badge, and cops had to answer to me, and that was great. I met Sharif that year and started running Swing the State in my spare time with Sharif and about ten of our friends. This was a fiercely partisan project. We were like, “We do not want George W. Bush to win re-election. That would be terrible, we must put an immediate end to this.”

The 2004 election did not work out the way we wanted the 2004 election to work out. I continued investigating police misconduct until 2007. Then I got a phone call from a friend from college and he offered me a job at MySpace.com. I literally hadn’t heard from this guy in years. Do you remember MySpace?

I was very active on MySpace. It took me a long time to get it out of my top Google results.

Oh, that’s really funny. I was active on Friendster and then someone I worked with investigating police misconduct literally said to me, “Oh that’s right, you’re old. You people are all still on Friendster. Young people are on MySpace.” And I was like, “I’m young too!” So I created a MySpace profile that I literally never checked. I never really used MySpace until my friend from college called to offer me this job. I was wholly unqualified for this job —I feel like this is a key part of this story. But he knew that I had been running a civic tech project, and as far as he was concerned this meant i worked in technology. I was like, “No, no, no, I have passion projects in technology.” But, you know, this was 2007 and you could accept jobs that you weren’t remotely qualified for. So in 2007 I stopped investigating police misconduct, moved from New York City to Los Angeles, and started working at MySpace.com when MySpace was pretty much the center of the online universe.

I got to LA and realized I didn’t actually have any friends in LA. This meant I had a lot of downtime and decided it was time to start another election project. And that’s where Long Distance Voter comes from. From me not having any friends in Los Angeles.

“This was 2007 and you could accept jobs that you weren’t remotely qualified for. So in 2007 I stopped investigating police misconduct, moved from New York City to Los Angeles, and started working at MySpace.com when MySpace was pretty much the center of the online universe.”

That’s beautiful.

It’s amazing what not having friends will do for your spare time and your creative drive. So backing up a bit, in 2004 I thought that the best way to increase voter turnout was to register more voters. This was a very common thought back then. So Swing the State and our partner groups, like Acorn and America Coming Together (rest in peace both groups), were part of this massive, nationwide, voter registration effort. At the end of the day, it didn’t seem to have much of an impact on turnout. Progressives were out registering conservatives four to one, but we certainly weren’t winning elections.

By 2006, I started to wonder if voter registration was related to voter turnout in any way. I’m not an academic, I didn’t have an actual funds to study this, but my gut told me to focus on something other than voter registration. I decided that my next project was going to focus on some group of people who were already registered to vote, who were highly motivated to vote, and who had some sort of roadblock that I could clear using the internet. If we’re being honest, I mostly wanted to stop doing door-to-door voter registration. I’d done a ton of that in 2004 and 2006 and it was just terrible. So late in 2006 I decided I would never again carry a clipboard.

Anyway, so now it’s 2006 and I’m in Vegas—where all great ideas are born—at a brand new political conference called Yearly Kos. A group of us were sitting around, and my friend John wanted to go ride a mechanical bull. Everyone was drunk, and I was like, “Do not go ride a mechanical bull. This is a terrible idea. Instead of riding a mechanical bull, I need you to help me figure out something.” And John was like, “What?” I was like, “I need to come up with a group of people who are already registered to vote, who are highly motivated to vote, have some sort of roadblock that we can clear using the Internet, because I really, really do not want to have to go door-to-door every again.” And he was like, “What about absentee voters?” And I was like, “What?” And he was like, “When I did absentee in college, it was really confusing and I’m still not sure if my absentee ballot was counted. Is anyone running an absentee ballot project?” And I was like, “I don’t think so.” And he was like, “Great, we should do that,” and then went off to ride this mechanical bull. And that is Long Distance Voter’s origin story.

“I’m working at Myspace during the day as a product manager. So during the day I’m identifying what people need from the internet, and what sort of tools we should build, and how you could run an engineering team. At night, I’m working with my friends, and we’re doing our nerdy voting project. I continued this pattern of having working as a product manager during the day, and volunteering with my friends to save democracy at night, through several jobs.”

I don’t remember how riding the mechanical bull worked out for John. He obviously lived to the morning, because we were all fine the next day. Anyway, that conversation happened in 2006. In 2007, I moved to Los Angeles, had no friends, and reached back out to John about his absentee ballot website. John and I recruited a bunch of our former coworkers (we had all investigated police misconduct together for the City of New York) and we started building the Long Distance Voter website. We had $5,000. I think there were ten of us—there were ten of us. Everyone took five states. We called the Secretaries of State, we asked them to walk us through it. We called every Secretary of State in America, and we asked them how you voted absentee in their state. (This is incredibly boring, I realize. Just picture us all investigating police misconduct, that makes it more exciting.) We built what was essentially a Wiki, with one page per state, and we had our first half million visitors within six months. So, we were like, “Alright, let’s keep doing this. We’re awesome.” And so we kept working on the site. Everyone was a volunteer.

We added more features to the site because users asked us to. People asked, “Hey, how come you don’t have a voter registration tool?” So we threw the Rock the Vote voter registration tool into the site, and quickly became Rock the Vote’s number one partner — in terms of registrations — out of 500 groups using their tool. People started asking us when early voting happens, so we created early voting page which is still the first hit on Google. So we just kept going with the site.

Meanwhile, I’m working at Myspace during the day as a product manager. So during the day I’m identifying what people need from the internet, and what sort of tools we should build, and how you could run an engineering team. At night, I’m working with my friends, and we’re doing our nerdy voting project. I continued this pattern of having working as a product manager during the day, and volunteering with my friends to save democracy at night, through several jobs.

That’s amazing.

Thank you. It makes no sense though. Everyone in voting assumed this was my full-time job. I’ve been Debra Cleaver from Long Distance Voters since 2008. At the same exact time, I was Debra Cleaver from Myspace, then Debra Cleaver from Truecar.com, and then Debra Cleaver from Change.org. It’s like I was Batman, but less cool. I had an election alter ego who did not get to wear a mask and a suit.

I feel like we’ve I’ve heard a lot of exciting things you’ve worked on, have we missed any of the really proud and exciting things?

No. Honestly, spending my twenties investigating police misconduct for the City of New York was awesome. I would also say—and this is a fact—that the New York City Police Department is the best trained, most heavily regulated, police department in the world. The fact that New York City has civilian oversight is really meaningful. A lot of the nonsense that happens in other places does not happen in New York, or doesn’t happen without immediate repercussion. New York City’s Internal Affairs Bureau is the model for Internal Affairs departments throughout the country. Living outside of New York, I’m astonished that there are police departments with no civilian oversight. If the police are only accountable to themselves, and not to civilians, then we are living in a police state. That is the literal definition of a police state: one where the police are only accountable to themselves. In New York City, the police are ultimately accountable to the civilians that they police. That doesn’t seem to to be the case outside of New York. New York City is certainly not without its racial and systemic biases, obviously, but it never felt like the wild west. Outside of New York, things seem nuts right now in terms of police misconduct.

What have been your biggest struggles over your career path, be it directly related to work or even personal? What have been the hardships you’ve had to overcome?

I loved investigating police misconduct. It was just awesome. I was also our union shop steward. In addition to investigating police misconduct and running Swing the State with my friends, I also engaged in a three-year battle with management. I filed all these large group grievances against management, and won them all, and that was just amazing. So I had this really amazing time, investigating police misconduct, and being a bad-ass, and driving the management nuts, and being a union shop steward. And then one day I realized, “I need to get the hell out of government.” Once you win massive group grievances, your career is pretty much over, you’re black-balled.

“Working at MySpace was amazing. If you saw a woman in the engineering department, there was a very good chance she was in charge of her team. The MySpace technical team was run by women. So my introduction to working in tech was to have all these bad-ass, fierce, unapologetic women running the show.”

So, MySpace came at the exact right time. Working at MySpace was amazing. If you saw a woman in the engineering department, there was a very good chance she was in charge of her team. The MySpace technical team was run by women. So my introduction to working in tech was to have all these bad-ass, fierce, unapologetic women running the show. The women were incredibly smart and really scary, and they’ve accepted me as one of their own, and I always had a great time at work. The guys at work would tell me that that wasn’t the case at other tech companies and that their wives and girlfriends had a much harder time working in tech. And, I said, “Oh, that’s weird, because I feel like MySpace is female dominated.” And they were like, “Well, MySpace is the exception to the rule.”

And then, I went to work at TrueCar.com, which was an automotive tech company. It was male dominated, but still a really wonderful professional experience. It wasn’t fun, the way MySpace was fun, but everyone was a professional. We came in, we did our work, and we were all paid well, so we were motivated by money, not necessarily our love for the automotive industry. Even though it was a predominantly male staff, I never thought it was a boy’s club. And then I moved to San Francisco, and the San Francisco tech scene was unlike anything I’d ever seen.

Tell me more.

I came to San Francisco tech companies and I suddenly was surrounded by people who had never heard of professionalism. Everything from “please show up to work on time” to “please do not tell jokes during the day, this is inappropriate”. I’ve never considered professionalism and fun to be at odds. I was like, “Professionalism is what enables a diverse group of people to together.” My team at Myspace was widely regarded as one of the happiest teams in the company, and Myspace was a big company. My team was 50% loudmouth white homosexual, and 50% somewhat quiet engineer who had grown up in India. So this was not a group of people that you would expect would really gel, but we did. The quieter coworkers kept the loudmouths from being bonkers and off the wall. And the loudmouth homosexuals made things light hearted and fun. And we were absolutely the happiest team in the company, and professionalism was why we could work together. Ken, my lead developer, is a wonderful person, also a devout Christian. So just during the day I didn’t make off-color comments about religion, because that would inappropriate. We just didn’t make off-color race or gender jokes in general, cause that would be inappropriate. So we had this team at Myspace that was diverse in terms, and race, and religion, and country of origin, and still managed to laugh all day, every day.

Then I moved to San Francisco, and suddenly things were just not funny. It’s not funny when you’re in HipChat, and someone is literally telling dick jokes. And it’s not funny when you’re the only woman on a team of 35. I’m used to having more men than women on a team, but I’m certainly not used to having 35 men and one woman. And I’ve found that when you build a homogenous team, people forget all about professionalism because they don’t have to moderate their behavior to accommodate people who aren’t exactly like them.

“Then I moved to San Francisco, and suddenly things were just not funny. It’s not funny when you’re in HipChat, and someone is literally telling dick jokes. And it’s not funny when you’re the only woman on a team of 35.”

I’d never actually articulated to myself, ‘I work in a boys’ club’ until I started working in SF. I’m a short-haired, loud-mouthed dyke and I’m very comfortable with predominantly male environments. But a boys’ club is very different beast entirely.

You might need to pepper me with some questions now because good Lord, do I have stories. So many stories.

What have some of your experiences been like?

Okay, some of the stories are just kind of hilarious. I had one software engineer who would groom at his desk. He’d trim his nails and comb his very long beard and it was just kind of weird. And his hygiene just wasn’t great. Really sweet guy, but terrible hygiene. And he would take off his shoes and his feet smelled terrible. I just pulled his boss aside and was like, “You got to deal with this. We have to have a shoes on policy at work.” His boss looked pretty uncomfortable, but there was no way I was going to deal with that mess. I told the boss, “Maybe you can talk to the boys about hygiene. You don’t need to say any of us have brought it up but it would be great if people could bathe once a week. That would really be great.” That’s a funny story: you don’t expect to have to tell a 40-year old man to bathe, but not the end of the world.

“I’ve found that when you build a homogenous team, people forget all about professionalism because they don’t have to moderate their behavior to accommodate people who aren’t exactly like them.”

Less funny story. At one job a software engineer punched another software engineer in the face at the holiday Christmas party. Boys will be boys, I guess. One of the boys was mouthing off at another one of the boys, and the second boy had enough of it and punched the first boy in the face. On one hand, I would say a lot of us had wanted to punch this guy in the face. On the other hand, but you may fantasize about punching a co-worker in the face but you don’t actually do it. And they weren’t boys—they were grown men and we were at the company Christmas party. There was an open bar, and everybody was drunk and dancing, and out of the corner of my eye, I see people who look like bouncers and I think, “Those look like bouncers.” And then I immediately realize those are actual bouncers because one of the engineers just punched another engineer in the face. So that wasn’t great [chuckles].

I was like great, “I’m getting out of here.” And the CEO literally catches me as I’m leaving and he’s like, “Hey, what just happened?” And I was like, “Well, one of your engineers just punched another one of your engineers in the face.” And he was like, “Why?” And I was like, “I don’t know. I haven’t ever punched anyone in the face so I can’t really imagine.” And he’s like, “But you have to have some idea.” And I’m like, “Well, first, your engineers are a bunch of man children, and second of all the one who was punched in the face is really objectively very annoying, so he probably mouthed off to someone who’s much bigger than him and got hit in the face.”

At this point I’m just trying to leave because I was pretty drunk—there had been an open bar—and I’m like, “I just cannot be talking to this jackass CEO right now.” And he’s like still talking to me, and I was like, “Hey, I’m not trying to tell you how to run your business but you need to call the company attorney, like right now.” And he’s like, “No, no, I don’t think it’s a big deal. I don’t think we need an attorney.” And I’m like, “One of your employees just punched another employee in the face at a company-sponsored event. You need an attorney.” And he’s like, “No, no.” And I was like, “Oh my God, how can I make this clearer to you?” I said, “You need the other gay Jew. I am your product manager, the other gay Jew is your attorney. You need that gay Jew. I cannot help you with this situation. I don’t know why one of them punched another one in the face, but I do know that you need an attorney.” And, of course, the next day the attorney was like, “Thank you for having him call me.”

“I would also routinely wind up the only woman in a room of company leaders. This was a global company so we had 20 country directors at least 50%, maybe 60%, were women. But if we had a meeting of the country leaders, we would only fly men in.”

This situation was ironic because just a few hours before the Christmas party another product manager and I had gone to the CEO to the lack of professionalism with the engineers. He was like, “What do you mean?” And I was like, Well, in the past week, one of them stood up and yelled at another one for no apparent reason. Another decided that he’d had enough of a meeting that we were in, so he slammed the table and announced that he was “done talking about this.” And what he was done talking about was literally his team’s plan to finish a project, so he stormed out. We had another male engineer—I should stop saying male engineers, actually, they were all men—throw something in a meeting because he also didn’t feel like he should keep answering questions. And the questions were always about work, like, “When will this be done?”, or, “Can you help us understand why this project is four weeks late because we have outside partners who are waiting.”

So anyway, the day of the holiday party I went to the CEO to talk about the lack of professionalism, and several hours later one of the engineers punched another one in the face. Way to underscore my point.

God that was a long-winded story. I would also routinely wind up the only woman in a room of company leaders. This was a global company so we had 20 country directors at least 50%, maybe 60%, were women. But if we had a meeting of the country leaders, we would only fly men in.

What??

Right? So I started talking to the CEO about this, calling him out. The first time I walked into his office and said, “Hey, I think we need to talk. I just left a meeting of 15 people and I was the only woman in the room. And the only reasons I was there is that I happen to be based out of San Francisco, and the meeting was here, and I couldn’t help but notice that you didn’t fly any women in.” And he was like, “What do you mean?” And I was like, “More than 50% of the country directors are women. So when you were choosing who to fly in, why didn’t you choose to fly any of them in?” And he was like, “Oh, I hadn’t thought about that.” And I told him, point blank, “Listen, it’s pretty uncomfortable for me to say this, but I think you’re running like a boys’ club here. I don’t think this is conscious, but when you personally picture leadership, you seem to only be picturing men, and we need to think about what that means for our company.”

“There would be these meetings with say me, and the CEO, and say two other men. And I would just pitch an idea at CEO, and he’d say, ‘Well, that’s a terrible idea.’ And one of the other guys would repeat verbatim what I had maybe five minutes later (because we would have all agreed going into the meeting like that was the best plan), and the CEO would be say ‘That’s a great idea! Debra, why don’t you come up with ideas like this?'”

And at first he seemed pretty responsive to this, but nothing actually changed. I was good friends with the head of HR and we started to have unofficial conversations about this. Then then they became official conversations. And, oh my god, there would be these meetings with say me, and the CEO, and say two other men. And I would just pitch an idea at CEO, and he’d say, “Well, that’s a terrible idea.” And one of the other guys would repeat verbatim what I had maybe five minutes later (because we would have all agreed going into the meeting like that was the best plan), and the CEO would be say “That’s a great idea! Debra, why don’t you come up with ideas like this?”

The first time it happened everyone laughed because we all thought the CEO was kidding. And the CEO asks us why we’re laughing and one of the guys says, “Well, I mean this is Debra’s exact idea. She just said this five minutes ago.” And I was like, “Yeah, that’s my exact idea.” And the CEO was honestly confused. It was like he hadn’t been in the room at all. That was the first time I had encountered sexism that was like cartoonish in nature.

“It started to feel like a comical exercise in gender stereotyping, only it wasn’t actually funny.”

I was at that company for about a year and a half. It reached the point where the conversations with HR were no longer unofficial, and the CEO and I would get into it regularly. I would say things to him like, “Hey, your revenue projections are nonsensical. I can’t even imagine where you’re getting these numbers from, but based on our actual revenue patterns, we’re going to have layoffs.” And he would say, “Well, you’re just not being optimistic.” And I was say, “No, I’m just being realistic. We have a huge staff, so I think this is a problem.” Other times he would say that I wasn’t metric-driven, which was really bizarre to me since I was always trying to talk to him about revenue. Once after he told me that I wasn’t “metric driven” I said, “I don’t know ‘metric driven’ means what you think it means, but the metric that I want to discuss with you is revenue. Revenue is a fancy way to say the money we need to operate our company. Whenever I try to talk to you about revenue, you shoot down the conversation, but then you want to spend literally hours every day second guessing every minor decision I make because you’re worried that it will have only a .4% increase in conversions instead of .6%.”

This became a constant refrain with him. He would routinely say, “Well, you’re just not numbers driven,” or “Debra, you don’t have good ideas.” Because money clearly wasn’t an important metric . And it started to feel like a comical exercise in gender stereotyping, only it wasn’t actually funny.

I was going to leave, but then we got this new female president. I decided to stick around, and see if things improved. Things got really shitty, and literally I would get criticized for the tone of voice that I used in email. As if emails have a tone. During the last two months the president started telling me—I am not making this up—that I needed to smile more during the day. But the reason I stopped smiling was that it was just not fun to come into work. My guys—my team—actually noticed and asked if I was mad at them. And I was like, “What do you mean?” And they were like, “You used to joke around with us every morning and now you don’t joke around at all. You just put your headphones on and you work.” And I was like, “No, no, I’m not mad at you guys. I have things going on in life.” I was amazed that they’d noticed because, like lots of straight men who work in engineering, they were just completely oblivious to what was going on around them.

Oh, and the one performance review I had read like that that article that was going on around on Facebook that highlighted the phrases and that are only used in women’s performance reviews. Like “abrasive.” I was “abrasive.” We did 360 reviews and this feedback came from from male colleagues who hadn’t been pulling their weight at all until I was on staff. I would say to them things like, “Hey, we pay you six figures and in return for that we expect you to do the work that you’re assigned during the day in a reasonable timeframe.”

I’m trying to think of funny stories for you, but none of this was funny. My life was a parody of stereotypical sexist behavior.

Man, you worked at a comical extreme it sounds like.

The amazing thing about this is I had just left this automotive tech company, which was just not like that at all. It was professional, it was fine and sometimes I was the only woman in a room, but only because it’s tends to be men who are jazzed at the thought of working at an automotive tech company. The company where I had the most negative experience was a social enterprise where people really prided themselves on how aware they were of systemic racism and sexism and things like that. Irony alert.

Major.

Do you want to know how that ended? This is the only good part about this entire situation. There was this project that the CEO was really stoked on even though it was a really stupid idea. It was a clusterfuck of a project but my team took it on because we’d been working on something else forever and needed a change. I spoke to the heads of every major division in the company and we figured out literally the only path forward. I got buy off from everyone before talking to the CEO. Then someone’s assistant scheduled like seven hours of meetings, and I was like, “We don’t need seven hours of meetings, but whatever.”

We start the very first meeting, there was a room full of people, and I said to the CEO “Hey listen, everyone in the company has agreed there’s only one path forward, so all we really need right now from you, CEO, is for you to sign off on this path forward so everyone can get started.” And he spends the next seven hours laying into me as a person. How it’s clear I “haven’t really thought about the project” and “I’m not taking it seriously”. After a few hours I pulled the other product managers into the meetings as well because I needed backup. Both of them repeatedly told the CEO that we all agreed that there was only one path forward. So the CEO starts saying how it’s clear (somehow) that I’m “not thinking about the metrics and blah, blah, blah.”

So seven hours later, it’s time to leave for the day, and someone has scheduled some dinner that I’m supposed to go to. But I’m in tears, which has never happened to be before at work (don’t worry, no one saw). And I called a friend from New York. This guy has known me for two decades, and assumes someone has died because I’m crying. And I tell him, ”I’m crying because I have feelings. And I’m not used to having feelings. And I don’t know what to do about this.” My friend tells me, ”Go home, get a pint of ice cream, and watch Scandal or something.” And I’m telling him I can’t just go home because there’s some fucking dinner I have to attend. And he was like, ”Okay. You know how to handle this. Do not talk during the dinner. Just sit at the edge of the table and drink your wine and don’t talk to anyone.” And I was like, ”Okay. Got it. Just drink quietly.”

“So finally I say, ‘You wanna know what’s going on?’ And I held up my fork and said, ‘I would rather stab out my own eyes with this motherfucking fork than talk about our goddamn job or our goddamn misogynistic prick of a CEO.'”

So I get there and no one’s there, and I start drinking. Everyone else was a full 30 minutes late. And then we sit down and I’m like at the very end of the table, and someone’s like, “Hey, Debra, come sit at the head of the table.” Because normally I’m the funny one. And I’m like, ”Oh, fuck.” But I tell myself, ”Just keep drinking. Just keep drinking. You have this plan.” And everyone keeps trying to engage me in conversations, but I’m not willing to talk. And none of these people have ever seen me not say a word for 90 minutes, so it’s starting to get weird that I’m not talking.

Someone, I can’t remember who, just wouldn’t let it go and kept trying to engage me in conversation. And at this point I had probably a bottle of wine on my own, and I was like, “I just don’t really want to talk right now.” And someone’s like, “No, for real. You’ve never been quiet this long. What’s going on? Blah blah blah.” And they just kept trying to talk to me about work and about the meetings we’d just had and whatnot. So finally I say, “You wanna know what’s going on?” And I held up my fork and said, “I would rather stab out my own eyes with this motherfucking fork than talk about our goddamn job or our goddamn misogynistic prick of a CEO.”

And then I went back to eating my food while everyone else sat there stunned and quiet. I ate my food, finished my bottle of wine, went home, the next day took a sick day, and the next day was told to come into work at 8AM (which is two hours before I get to work) to be fired. And so ended my illustrious career working for someone else. Misogynistic prick in question did not fire me himself, he had a woman do it. And while she was firing me, she was said, “I am really sorry about his behavior the other day.” Because she had been there in the all-day meetings.

I still think that the fork incident was my finest professional moment. I can see how calling calling someone a misogynistic prick would be a problem, if it wasn’t objectively true. But in my defense, he was a misogynistic prick. This was just a statement of fact.

As an aside, the guy who punched the other guy in the face—not fired. The guy who’s throwing things in meetings—not fired. The guy who posted a bunch of swastikas on Facebook publicly while identifying the company he worked for—not fired. None of these people were fired. Me—a bottle of wine in, state objective truth about our boss—fired. So, I don’t know. I still think it was a good way to go out.

How do you feel about the state of tech in 2016? What excites you and what frustrates you?

I’ve never been interested in technology for technology’s sake. I’m not like, “Look at this awesome app that I downloaded that lets me throw angry birds at something.” I’ve always been interested in technology as a way to solve other problems. In 2004 when I first started wading into this political work it my question was, “How can we use the internet to organize volunteers?” Now, I look at the internet as a whole and think, “this is the most powerful and least expensive information distribution system we have ever seen.” The internet is the single most important advancement in human communication and information distribution since the printing press. Only it’s cheap It’s accessible for everyone. You could host a website for seven bucks a month at DreamHost and the whole world can see it.

“I’ve never been interested in technology for technology’s sake. I’ve always been interested in technology as a way to solve other problems.”

For me it’s not that we’re going to solve the issues plaguing American democracy with technology, it’s that we can use technology to amplify the solutions we’ve already identified. I’ve focused on education—how can we educate all Americans about voting without spending a bajillion dollars? We can use the internet. Every day I see so many examples of people using technology in creative ways to solve problems that are much bigger than “how am I going to get my laundry done” or “where can I find a taxi.” I love what we can do with technology, but I don’t necessarily love technology itself. I will use the most boring, established, non-sparkly technology to solve really big problems.

“For me it’s not that we’re going to solve the issues plaguing American democracy with technology, it’s that we can use technology to amplify the solutions we’ve already identified. I’ve focused on education—how can we educate all Americans about voting without spending a bajillion dollars? We can use the internet.”

In terms of culture there interesting things afoot in the tech world and in the valley. The younger women entering the field now have mentors that women my age didn’t necessarily have. And these mentors have had enough of this weird, sexist bullshit. There are a number of women in tech groups, and lesbians in tech, and a consistent topic of conversation is how do we protect these younger women? How can we make sure that sexism doesn’t thrive in the valley? And what do you do when your team is off the wall bonkers and out of control? A lot of us also think about how lack of diversity affects not just the companies, but the world. Who has access to technology and therefore who has access to information. There is so much thoughtful conversation going on around access issues.

I’ve personally come to believe that your user base will resemble your staff. If you have a staff that is 90% white men, you might wind up with user base that is 90% white men because your team will build a product that meets the needs of the people they know. You have these companies that are hegemonist and therefore the solutions they come out with are pretty defined and not very creative. In my field the way that plays out is through the techniques we use to reach underrepresented voters. We’re talking about low income voters, voters of color, young voters, urban voters. Basically people who aren’t straight white men. Traditional voter outreach tactics don’t seem to reach these groups, likely because elections and campaigns are generally run by straight white men. So these men run campaigns that speak to other straight white men, and a significant percentage of potential voters are left out of the fold. If we want to have an electorate that isn’t just straight white men, and we want to have candidates that aren’t just straight white men, we need to bring people who aren’t straight white men into the fold. I want to reach the people who are not being reached, and therefore I will not build a team of all straight white men, even if I live in San Francisco. If we all look the same, we’re going to reach the people who are already being reached.

“I’ve personally come to believe that your user base will resemble your staff. If you have a staff that is 90% white men, you might wind up with user base that is 90% white men because your team will build a product that meets the needs of the people they know.”

I think that’s true for every tech company. And just see right now in 2016, there is some sort of shift going on, and people are calling out the lack of diversity, they’re calling out the VCs, they’re calling out the CEOs.

Yeah, it could be why we’ve hit a wall with a lot of these unicorns, of like—you had all the potential to globalize, but at some point you hit a wall.

Yeah, you somehow were unable to reach people who didn’t look exactly like you. And it turns out there’s only so many users who look exactly like your team.

Oh, i just read a quote the other day on Facebook that was great. “When the lights come on, a unicorn is just a horse in a party hat with a fake horn.”

These unicorns, when you remove the VC funding, they’re often just failed companies.

So I was born and raised in Miami, Florida. At some point pretty early on someone identified that I wasn’t just good at math, I really liked it and so a few teachers over the years tried encouraging that, and then in a high school there was a teacher who picked up on it and said, “If you like math I’ve got something else you should start doing.” So he got me into programming because it was a lot of applied math. From there it took off like a rocket. I went to—a couple exceptional teachers notwithstanding—a really not-great public high school. I got into a top college for computer science. I spent five years working hard, not getting enough sleep, operating on probably unsafe amounts of caffeine, learning a lot, being around some really smart people, really intimidating people, learning how to socialize with people who were not just smart but interested in these things that I found interesting, which was new for me in my life.

“I was used to being on the outside. I was into math and computers and other people were into cars and sports.”

I was used to being on the outside. I was into math and computers and other people were into cars and sports. There’s nothing wrong with them having their interests but I didn’t have anyone else who shared mine. That changed when I got to college and it was amazing to have an environment that was basically built for doing that, for going and chasing something I’m interested in to the extreme. I didn’t do it perfect, right? I don’t think anyone does. I think a lot of people would go make some different decisions if they did college again, but that’s how it goes.

I had some summer internships out in California. My senior year I interviewed with Uber because—it’s funny because at the time one of the things that was intensely frustrating to me about my life was how difficult it was for me to get around Pittsburgh as a student. Just as someone who couldn’t afford to own a car in a place that needed one. Then I heard about Uber and thought, “that’s a path forward—that’s a way for people to not own cars.” So in 2013 I applied, 2014 I start my job after graduating. I’m actually working toward something I really do believe is good for the world. Working towards this future where individuals don’t have to own a car to survive and making things safer because people suck at driving, making driving a skill that people can get paid for rather than requiring everyone learn it.

“A couple close friends knew that I thought of myself as a woman, but that wasn’t a public-facing thing. It was actually a huge source of distress in my life. There was this thing that I feel about myself, that I just can’t tell the world in general.”

In parallel to the technical growth, I’d had struggles about my gender for a while. I presented as male basically until I graduated college. A couple close friends knew that I thought of myself as a woman, but that wasn’t a public-facing thing. It was actually a huge source of distress in my life. There was this thing that I feel about myself, that I just can’t tell the world in general. I felt really unsafe—I felt like I couldn’t come out in college, so moving across the country and starting my first job, coming from Pittsburgh to California felt like getting the chance to start my life with a clean slate. If there was anyone I knew in college who I didn’t want to talk to, who I thought wouldn’t like me, I didn’t have to deal with them. I was just in a different place, way bigger. I moved across the country, came out of the closet, and started a new job in the span of two weeks. Everyone tells me I’m crazy, but I think there’s no better way to do it. You want a clean break, everything’s new. I’ve been out and about and living as genuinely me as possible ever since starting this job, and I have never been happier. It’s been rad.

“I moved across the country, came out of the closet, and started a new job in the span of two weeks. Everyone tells me I’m crazy, but I think there’s no better way to do it. You want a clean break, everything’s new. I’ve been out and about and living as genuinely me as possible ever since starting this job, and I have never been happier. It’s been rad.”

What was college like for you, both academically and personally, as someone who didn’t totally feel like they could be yourself?

In a lot of ways, college was the first step in me feeling more comfortable being myself. In primary school—elementary, middle, and high school—being the smart person in the room, being the person who cared about school in the room, wasn’t taken well; that was something I learned to hide. And then going to college, and being able to chase that was awesome. There were some decisions I made that weren’t the best. I wish I’d had a better sense of how to manage my time before I got to college so I could’ve gotten more out of it, things like that. But being able to care about this and having that be okay and having no one judging me for that was great.

I feel like I got a lot out of college and I regret not learning more, but at the same time there is this thing that’s core to me. More than what I do, it’s how I relate to myself that I couldn’t share with the rest of the world—or at least I felt like I couldn’t share it to the rest of the world. It wasn’t pleasant. There were times where I felt totally miserable, that this is going to be bad forever, that I’m never going to be able to fix this, that I’m never going to feel comfortable coming out because I had really weird notions about what that would require, what that meant, or what the objective was, and was just confused. I didn’t have anyone to talk to about it because there weren’t that many other trans people at school. There was one who was in school at the same time as me, and we talked some, and she’s really cool, but still her experience was in a lot of ways very different. When I moved—When I eventually came out, and moved across the country, she did that before she got to college. She was four years ahead of me and that was part of what got me thinking about doing this. Well, maybe I could just be myself and be happy for that when I eventually moved away—moved to California. But it was hard. There were times when it seemed world-consuming, and I felt like my relationships with people were false because they were predicated on this presentation that was not true, wasn’t genuine. People who got along with me, I felt they got along with me because of a lie. That was awful.

So, you moved here with 100 bucks.

There’s this thing that a lot of companies do where you have some moving bonus, or some signing bonus but they’re done as reimbursement. So, I’m like I need to get out of here. I have enough to buy a plane ticket. A friend had been out here for awhile, and had savings before they even graduated college, gave me a very generous personal loan—they did me a huge personal favor, and covered the down payment on my apartment. “This is a no interest loan. Pay it back whenever you can.” That’s still—oh, my God. That’s so valuable to me. I could have crashed on someone’s couch for a while. That would have just been really, really bad for a bunch of reasons, and I would have gotten off to a horrible start while trying to balance all these other things with not having a private space.

“The first day I went out wearing a skirt and presenting as a girl I was instantly cat-called 50 feet from my front door.”

And finding a place is so hard in the first place. 

That was huge for me. But I drained my bank account buying a plane ticket. There was $100 left and I didn’t have a wardrobe—at least I didn’t have the right wardrobe. I had to use some creativity and find some good finds at thrift shops and stuff. I start my job and—I remember my first paycheck was needed to buy basic things, and ensuring I have enough money to be able to feed myself. Thinking I could have fed myself cheaper after every meal was not a pleasant feeling. So being able to not have to worry about food was cool. I remember a second paycheck though. I thought, “I’m going to spend an irresponsible portion of my net worth on a mattress [chuckles].” It was my first adult purchase—a really, really nice mattress. I don’t regret it in the least.

For sure [laughter]. Tell me about coming out at the same time as starting Uber and what that process has been like for you.

The thing I really want to stress is I don’t want this to come off as me dishing on the company, or it’s so bad because this is all I’ve got. I just want to make that clear. I know I don’t have to say that, I just feel more comfortable saying it.

Absolutely.

The option was come out before I started my job or come out after. I decided to do it before. Basically, everything all at once is new. The first day I went out wearing a skirt and presenting as a girl I was instantly cat-called 50 feet from my front door.  And that is the weirdest experience of my life, I still don’t know how to process that. You know? At the one time it’s really gross and disgusting and dangerous and I’m scared. And on the other hand it is upsettingly validating, especially for someone who is worried they won’t be read as female, right? For that to happen to you. It’s like, “well okay.” Oh God, that was weird.

Welcome. [chuckles]

Yea I know, right? That’s what everyone told me. It’s like, “Hi, yeah this is it.” I didn’t think women were making it up, and you can say you believe them and you know it happens to them but experiencing it is another thing entirely. So that was weird. But ignoring everything else—so like .3% of the US population is trans. Male or female, .3 right? So that’s about 1 in 300. That’s pretty small, right? So the odds of there being another trans person at any company I interviewed with was low and I was sure I was going to be the first wherever I ended up working. And a lot of people haven’t interacted with a trans person before. I’m six foot one, I had streaks of pink hair, because I don’t believe in half measures, if I’m going to stand out I’m going to stand out on my terms. [chuckle] I have a deeper voice than one would expect out of someone wearing a skirt. I stand out.

Some of it I think was imagined, just me being paranoid about it, and some of it was that definitely that I attract attention. Every time I would get up to go to the bathroom—by the end of the second week I’m sure it wasn’t actually happening anymore but for the first two months I felt like heads were turning every time I would get up to go do something. I was big and noticeable and habitually not wearing pants, I don’t even own jeans anymore, I only wear skirts, so there’s this skirt flapping behind me because I usually wear full length skirts. I drew attention, or felt like I did, and it didn’t feel like good attention, I was extremely self-conscious.

At this point I’m a lot more comfortable with it, but it was weird at the time. it happened to me everywhere. I couldn’t walk down the street without people—I could feel their eyes on me, I could see them staring at me. Now I’ve gotten into this habit—I used to avoid eye contact at all costs thinking “please don’t look at me, please don’t look at me.” Now if I catch people staring at me I take my sunglasses off and stare them down. I shouldn’t have to feel bad about being me. Nothing is wrong with me. There are things that are imperfect with me, but there’s nothing offensive about me walking down the street. I shouldn’t have to defend who I am to randoms on the street.

“I’m six foot one, I had streaks of pink hair, because I don’t believe in half measures, if I’m going to stand out I’m going to stand out on my terms. I have a deeper voice than one would expect out of someone wearing a skirt. I stand out.”

So at work you can imagine it being a technology company, have a company Q&A session in the style of Google. Every Tuesday we’d have a staff meeting plus Q&A session. I think my second month I had a question I wanted to ask. So I get up and I ask it at the microphone. There’s a ton of people in this room. When I ask the question these people can see me on the screen. They’re probably thinking okay there’s a girl coming to ask a question. They can see the skirt and long hair, I read as female. Then they hear my voice and every head spins to look at me. For all I know they were doing that for every question (and months later I pay attention and they are doing it for every question), but I’m recently out and self conscious, so I feel like it’s because my voice was so unexpected. No one made a big deal about my gender, but after that if I would be put on meetings for things related to what I was working on and I wouldn’t know any of the names on the meeting list, but I’d walk in and every single person would know me by name from asking that question. I can’t walk into a room and hide anymore. I don’t blend in.

It used to be the case that if I got attention I was asking for it. I didn’t get all the attention I was asking for, but I generally didn’t receive unwanted attention. Now whether or not I want it I’m getting it. I have difficulty with names so it’s double awkward and I feel mortified every time someone greets me by name and I don’t recognize them. I just feel bad about it. There was a lot of—at least in grade school—conditioning to be shy. I felt like I couldn’t really be good friends with people because I—not just like in grade school, but while growing up—I felt couldn’t be genuine because of this gender thing that I couldn’t tell anyone about. Plus, things I was interested in people around me didn’t care about. I was pretty shy and quiet. So for the shy person, the person who was quiet in the back of the room to get all this attention, all at once, was different. You can’t prepare for it.

“I used to avoid eye contact at all costs thinking, ‘Please don’t look at me, please don’t look at me.’ Now if I catch people staring at me I take my sunglasses off and stare them down. I shouldn’t have to feel bad about being me.”

You mentioned also that you are worried about calling yourself a woman in tech.

It’s not that I feel like I’m invading women’s spaces, but I’m afraid of being accused of that in women’s spaces, for the same reason that I’m a little scared of showing up to women in tech meetups or things in technology specifically for women because someone might try to throw it in my face and I just don’t want to have to deal with that. I get anxious in multiple-stall bathrooms. If there’s only gendered restrooms in a building and I might have to interact with someone while in there, it’s nerve wracking. I shouldn’t be worried about that and if someone makes that unpleasant for me it’s not my fault. But that doesn’t reduce the fear of it happening to me, that doesn’t make it any more pleasant. The fact that it’s not my fault is kind of irrelevant. I’m just scared of it. I have some friends who have been really good about bringing me to these things and trying to involve me more and the female coworkers I have have been nothing but welcoming and supportive.

[NOTE—this interview took place before the recent rash of states trying to pass legislation keeping transfolk out of restrooms of the appropriate gender.]

“It’s not that I feel like I’m invading women’s spaces, but I’m afraid of being accused of that in women’s spaces, for the same reason that I’m a little scared of showing up to women in tech meetups or things in technology specifically for women because someone might try to throw it in my face and I just don’t want to have to deal with that.”

Yeah, on the flip side you’re doing some really amazing work and working on really cool stuff—I don’t know how you can talk about that, but I’d like to hear what excites you about work and what are some of the rewarding things about your work.

This is going to be a little difficult to talk about. I work on map related technology at Uber. Things that attempt to model the physical world and how we interact with it, how cars interact with it, how cars move around in it, things that try make predictions about those interactions. Specifically our routing engine, trying to predict travel times and paths. These predictions are used to inform a lot of intelligent business decisions. So, when I improve the accuracy of some of these predictions, or make them slightly more hardware efficient it enables so much. If I can make this prediction faster and more efficient then people can do more and plan further out and make better decisions. We’re talking about internal consumers, people who are internally using this. If I make them more accurate than we can—we can make better decisions. We can make more informed decisions, we can ask more questions if we are able to go faster.

“I do work I know it’s reflected in the physical world. I know that something moved because of what I did, because of my ability to do my job well. That’s great. That’s awesome. That’s really satisfying.”

At the end of the day, the things that I work on have a direct bearing on physical world. Our ability to predict these things, or our software’s ability to predicts these things influences what Uber pool match you get or what driver get dispatched to you. It’s reflected in the physical world, right? I flick bits and atoms move. That’s huge. The impact of my work is tangible. When I do things that make improvements on a per trip basis, times the number of trips we’re doing… To be able to say that we made that point one percent improvement across all trips, that adds up fast. And it’s not some really large number of eyeballs on an ad, or displays on a webpage, or better search results, or something like that. Those are also—people care about those things too, obviously. But I do work I know it’s reflected in the physical world. I know that something moved because of what I did, because of my ability to do my job well. That’s great. That’s awesome. That’s really satisfying.

You haven’t been in Silicon Valley too long, but I’m curious to know if you still feel like you have to suppress feminine parts of yourself to fit in in tech? Does that make sense?

I guess this is a little bit difficult because how do you gender a behavior? It’s hard for me to identify individual behaviors that I have and say, “Oh, this is inherently feminine,” or, “Oh, this is inherently masculine.” The best I’ve got is I wear skirts every day. That’s probably feminine. We can safely say that’s pretty feminine, right?

That’s a great point.

I do that no matter what. If anyone’s uncomfortable with it, they can deal with it. My hair is dyed, my skirts are long… My femininity is about how I make sense to myself, I don’t feel like I suppress my femininity at work or in tech or like there’s a need to.

How has life changed for you positively now that you can be yourself?

I’m way happier. I was a pretty sad kid, even through college. I feel like my emotional state was generally not positive for various reasons. Coming out here and getting to be myself—not only to be myself but getting to live my own life—I got to choose my job. I get to choose what I do with my spare time. I don’t have these looming assignment deadlines left over from college. I feel like I—it’s not quite discovering myself, it’s more like building myself. I get to choose who I am, getting to pursue my own interests and do things that I want to do. Work or hobby or people I socialize with. That’s been incredibly rewarding. I’m happy with how my life is going. There are things I’d change, there are things I recognize about myself that I don’t fully like, that I would alter or improve in some way. That doesn’t mean I can’t like myself. I’m making progress in that direction. I’m getting to move there. I spend my time how I want. I’m learning to play piano. I love music, I’ve loved it as long as I can remember. I’ve never played it, but now I’ve found myself with discipline and personal time and resources to try to learn how to play instrument. I get to decide that’s something I want to do. If I want to spend my time making weird stuff like skirts that glow in the dark or feel like playing with LEDs or maybe some Thursday nights or Fridays night I just want to sit in my room and play games with friends, I don’t have to feel bad about that because I’m actually doing the things that I want to do. When I spend time idle, I don’t feel bad about what I’m not doing. Because most of what I want to do, I am doing. Some things are resource constrained. There’s some things I just straight up can’t afford to do, but I can work towards that.

“I get to choose who I am, getting to pursue my own interests and do things that I want to do. Work or hobby or people I socialize with. That’s been incredibly rewarding.”

What are your biggest motivators? What drives you?

I think, this is really, really trite and cliche. But, I really would like to contribute to making the world in some way, some tangible way a better place. And I do get to define like the ways in which I want to better it. Maybe that means, I don’t think any American should be required to own a car in order to live their lives. Which is not true for most Americans. You talk to people in L.A or Miami, you need a car in order to have a job, and it owns you. If I can make progress towards that I can say. If I can try to like give people the ability to move around more freely or encourage things to become dense and more friendly to people not owning these burdensome expensive things. It’s one example but if I can find a way to make progress towards that, that’s satisfying.

I know people who just have a job to pay bills. If I didn’t need money, I’d probably still be doing this job which is a great feeling. I don’t know a lot of people that could say that. It’s not just my job. I can improve the world in small ways too. Maybe I think that there should be more music in the world. Maybe I think people should be more expressive. I can be more expressive. I can try to put some emotion into sound and try to make that more true in the world. I can try to be kind to people, be friendly, try to be genuine, make people feel comfortable being genuine around me, try to carry this through more of my interactions with people. Professionally I try to think about this in terms of the world at large. How can I make progress towards things that I think are important on at scale?

In my personal life, a lot of it’s interacting with my immediate surroundings. I think people should feel comfortable being expressive, so I try to do that with myself. It would be nice if people could be genuine around each other and say what they mean. I try make friends who feel like they can do that, make me feel comfortable doing that, find small pieces of community that feel that way and feel like expressing yourself is not just powerful—it’s important. It’s not the best answer, but it is mine.

I think it’s great, and I think it’s so rad that you are able to be doing so much of that so early in your career

Yeah, both coworkers and friends outside of work who are a lot older than me will ask, “How old are you? You’re 24? What?!” People seem shocked.

I don’t have everything figured out, no 20-something has it all together—but I do think I’ve at least got a good sense of what is important to me. Maybe I don’t have the best sense of how to act on that and how to make progress on that, and those are definitely things that I struggle with and I’m learning about as I go, but I at least do have a sense of what’s important to me.

My last question for you would be: What advice would you give for folks going through similar struggles who are either in tech or hoping to get into tech?

This is really hard. It’s difficult to generalize from your own experience. Like, I’m an engineer. I believe in having a lot of data and making decisions based on that, and really I’ve only got my one story. But being the person who you feel like you are, the person who you want to be cannot be that bad. And the people who don’t want that person, you don’t always have to deal with.

I understand the parent thing. I’m not out to my parents. And if you’re dependent on your parents, and you feel like you can’t tell them, that’s hard. I think you should not be ashamed of who you are who you want to be. And if you don’t feel like you can act on that right now, then try to make progress towards it, work towards putting yourself in a position where you can act like that. What that means for different people in different situations, there’s a million different answers to. But I think—yeah, I mean, it’s hard—I have no idea.

I think it’s important to not be ashamed of who you want to be. And I think that’s the first step to caring for yourself. That’s also kind of cheesy, but it’s true, right? Like, if you care about yourself, you will put so much more effort into getting yourself into a better situation, getting yourself into a place where you can work on those things, where you can be the person you want to be. You shouldn’t be ashamed of feeling the way you feel and wanting to be who you want to be. I think that might really be the most important thing to recognize, that might be the thing that someone should’ve told me—I wish I’d heard that. Senior year of high school that would’ve been great to hear, just to know it, have it come from someone who really did know me and care for me. If you can put yourself in a position where you can care about yourself and you can like yourself it just changes the way you look at your situation. It’s no longer woe is me, and doom and gloom, and I deserve this, it becomes maybe I deserve better, maybe I can work towards that.

“If you care about yourself, you will put so much more effort into getting yourself into a better situation, getting yourself into a place where you can work on those things, where you can be the person you want to be. You shouldn’t be ashamed of feeling the way you feel and wanting to be who you want to be.”

I’m from Miami. My family family has four kids. I have an older brother, I have a twin sister, and I have a little sister. I did really well in school. I played sports: basketball, track. I went to college in Miami and then I went to law school at Florida State. I always liked tech, but it wasn’t a career when we were kids. There was War Games and Space Camp and movies about the craziness of hackers—how it could go horribly, horribly wrong, but it wasn’t a job that you could have. My elementary school—I was in a gifted program and they had a computer class—and I built a space game on a Commodore 64. Yeah, I’m dating myself. [chuckles]

I was really into tech when I was really young, but it wasn’t a thing you could do. And when I got to undergrad, that’s when email came out. I remember they were like, “You can have email.” I was like, “What the hell is email?” They were like, “You can write letters to people on the internet.” [chuckles] Napster was out then.  It was all kind of the early wild, wild west before Google.  And then when I went to law school, it was the first year they had a laptop requirement, and so we all had to get laptops, which was awesome. I downloaded the Mame arcade simulator, and so I just pressed F8 or whatever to put in quarters, and I’d be sitting in law school playing video games. It was awesome. [laughter]

“I was really into tech when I was really young, but it wasn’t a thing you could do.”

Then I finished that and went to D.C. and got a Masters of Law, because I didn’t know what lawyers did day to day, and I wanted to be good at what I did before I started it. But it seems I educated myself into a bit of a black hole.  Instead of staying in D.C., I went back to Florida and no one knew what my degree was or what could be done with it, and nobody wanted to pay me to figure that out.  But I had classmates who had my degree and they got credit for an extra year of practice and got jobs at these big firms, and I couldn’t get interviews. It became very clear that people are kind of colorblind to a degree when you’re young because you’re in school and you’re not really a threat, but once you come back as an adult, things change. I wasn’t ready for that transition, my family wasn’t ready for it, and it caused some really difficult times.

Wow.

Yeah. So then I practiced law for a while, which wasn’t what I ultimately wanted to do. I wanted to be a law professor, but I practiced for a while because my parents put their foot down after three degrees.  I needed to get a job.  So, I did practice but unfortunately I ended up working for people who saw the law as a business, not a profession. Which means that my ethics didn’t line up with theirs.

And so I kept ending up in situations where people would think that I should be so happy that they gave me a job that I should do whatever they wanted me to do. But I had earned my position. I had three degrees. Like you didn’t just hand me the job. But just by virtue of who I was it just became a thing that, “Yeah. But who else is going to hire you?”

So I kept ending up at these firms where they wanted to do things to make them richer at the expense of the clients. And at some point I was like, “You can continue going down the same path or you can do something different.” So, I decided to do education for a while.

And actually I had a pretty good time like with the students.  But once again I ran into some difficulties and ended up not being offered a position in 2008, which was the beginning of the recession.  If you got let go at that time, there was really no backstop. So, I ended up doing a couple different jobs, I was a personal trainer for 24 hour fitness [chuckles].

“I basically packed up all my things into four bags and took planes, trains, and automobile, all the way to L.A. I stayed with my twin for the holiday season, and I moved sight unseen to San Francisco with my unemployment check as my only source of income and started sending out applications.”

Oh man.

Yeah. I did a variety of things. I was teaching at the Strayer, in their business law of department. I was teaching white collar business law and I looked at my book and I realized there were no lawyers who wrote it. I was like, “Why are there no lawyers in a white collar criminal law book?”  And I realized, it was because lawyers didn’t like business and businessmen didn’t like the law. So I was like, “Oh, well, maybe, I can fill that niche.” So, I went back to FIU and got a Masters in International Business.  I specifically went back to my undergrad because it’s an international focused university, and I wanted an opportunity to do an international internship. And I did that.  My last semester I had an internship in Scotland. I worked for a start-up—actually incubator high tech company that made holograms. Actual holograms.  Like, “Help me, Obi Wan, you’re my only help!”

[ laughter] It’s insane. When I was working with them, they were a start-up, so I got to work on their website and stuff like that. I got into a little bit of HTML, and I was like, “This is kind of cool.”  When I came home, I had been thinking of this idea of a website.  Black Americans traveling internationally is a pretty new phenomenon in the numbers that we’re currently doing it. And a lot of us– because I’d done a couple of study abroads and every time I left the country, the whole community was like, “You’re going where?” [laughter] There’s an anxiety. And you can’t really say, “Oh well, he went or she went.” And it’s hard to point the elders to information. And you kind of just—you look like you’re just going out there on your own. I was like I should probably do a website for Black American travelers. So you can have basic information that you can share. That became my passion for a little while.  I created a website and it was a whole big thing, learning all the different coding and whatnot.  I did use a platform but still you have to learn some things on your own. I’d taken a position with an e-book publisher, so I learned more HTML and even some CSS. Just various things on how to structure content and whatnot. But I’d gotten to a point in my life and in my relationship at the time where things just weren’t working in Florida. I always try to come back to Florida to be successful because I’m from Florida. You see all these other people in your home doing these things, and you just want—this is my home, I want to be successful in my home.  But I finally reached a point where I had to realize it wasn’t going to happen. I’ve only been in California a year [chuckles]. I came here last January—actually the November before. I basically packed up all my things into four bags and took planes, trains, and automobile, all the way to L.A. I stayed with my twin for the holiday season, and I moved sight unseen to San Francisco with my unemployment check as my only source of income and started sending out applications.

I was in hostels. Then, the week that I was supposed to receive my last unemployment check, I completely freaked out.  I was like, “I had no other backup.”  I couldn’t go back to Florida, I had nothing. So, I’m online, I’m looking, I’m looking, and I found a job meet-up that was hosted by the San Francisco LGBT Center. So, I walked from North Beach down to the San Francisco LGBT Center.  I had no idea how far it was. I get there, and it had already started, but they were cool and we talked. They said they’d help me with my resume. I came back the next day, and they helped me with my resume and I went back to the hostel, revamped it, and then I papered the entire Bay Area with it. The next day, I was supposed to come back and talk to a career counselor. And I wake up in the morning, I look at my phone, and I have an email from this dude at Google.com.  I almost fell out of my bunk! [laughter] Because I was like, “What? I didn’t apply to any jobs at Google.”  So, one of the jobs I’d applied for was for a vendor who worked on campus at Google. He was like, “Hey, can you have a phone interview on Monday?” I was like, “Yes!”  So the phone interview was cool. He asked me if I could get down to Google on Wednesday. I took a bus, and then the Caltrain, and then two buses. I couldn’t find my first bus stop when I got off the Caltrain, and so I was freaking out, and my friend in Florida is trying to Google map it for me, and it was a whole thing. I find the bus stop, get on the bus, get off, go get some food, and go stand at the second bus stop for twenty minutes like, “Oh, I have plenty of time.” And the bus comes like, “Oh, no, you’re supposed to be on the other side of the street.” Now, I’m freaking out like, “I’m going to miss this interview!” Mind you, I’m right down the street from the campus, but I’ve never been, so I couldn’t tell. I just didn’t know.

“I couldn’t go back to Florida, I had nothing. So, I’m online, I’m looking, I’m looking, and I found a job meet-up that was hosted by the San Francisco LGBT Center. So, I walked from North Beach down to the San Francisco LGBT Center.  I had no idea how far it was. I get there, and it had already started, but they were cool and we talked. They said they’d help me with my resume. I came back the next day, and they helped me with my resume and I went back to the hostel, revamped it, and then I papered the entire Bay Area with it. The next day, I was supposed to come back and talk to a career counselor. And I wake up in the morning, I look at my phone, and I have an email from this dude at Google.com.”

Finally, the second bus comes, I get off and have to walk all the way to the edge of campus. But I actually got there fifteen minutes before my interview, after I’d already called the guy like, “I don’t think I’m going to make it on time!” And then I made it, and it was cool.  I had the interview and it went really well. I’m walking out and I was actually walking on Intuit’s campus because they’re across the street, and I was just walking around on the phone because it’s just beautiful. I get a phone call and I had to tell my friend, “I’m going to call you back because I’ve got a phone call.” And it was the recruiter saying they wanted to offer me the job and I was like, “What?” This was the day I received my last unemployment check. [chuckle] I got offered the job as a vendor at Google. The next day I got on a megabus and headed right to my sister’s in L.A. and just vegged out for two weeks. She was like, “You can just stay here.” It was great, and I started, but even then it took a while to get up and running. I still didn’t have housing together, that took a while. The first place I got housing I signed a six month sublease, and then in three months my sub-lessor [chuckle] contacted me and was like, “Yeah, so the lease is up.” And I was like, “What?” “Yeah, you need to get out this month.” That was tough and it was just a variety of different things like that that kept popping up.

I ended up actually having to leave Google because the prospects for long-term employment had gotten kind of iffy. Not that it wouldn’t have happened, but their time frame was a lot longer than mine. I had uprooted my whole life. I wasn’t really in a position to be in a wait-and-see kind of attitude. So I took the opportunity to go to Yahoo, which was terrifying [chuckles] because all of my friends were at Google. It’s the first place I called home since I left home. It was the family that I made in California. But I went to Yahoo, and almost immediately upon entering Yahoo as a contractor, they interviewed me for an FTE position. And about two weeks into January, I signed my contract for an FTE position. I started my Google contract position February 23rd of last year, and I was scheduled to start my Yahoo full-time position February 13th of this year.

Wow.

It was.  The difference a year can make is extraordinary.  But, unfortunately, Yahoo fell apart about a week after our initial interview and my job went with it.  They called the day my background check cleared and rescinded my contract.  It was devastating.  A body blow.  It shook my entire network.  Like, I had come to California to change my life and I made it happen all in one year.  And one phone call snatched the rug from under me, under all of us, yet again.  It’s hard to keep getting up.  And, if there was ever a moment where that was a question, this was it.  But, I think my fighter is hard-wired.  Like she can go on auto-pilot when all of my other systems shut down.  So, I somehow managed to apply for a few jobs during the devastation.  And my circle held me up.  My sister and my girlfriend particularly.  The Monday after the news, my girl ended up spending the day with me.  And we went for a walk in the park.  It was such a nice day out, sunny and warm, and it just healed me some.  Like, I was still hurt, but I wasn’t shattered anymore?  Like I could move forward. And that week a recruiter contacted me.  We had a really good phone interview about a job that wasn’t for me.  And she told me she also recruited for Google and asked if I wanted to go back.  And I told her “With all my heart and soul.”  Because when you take a blow like that, you just want to go home.  And Google is my home here.  So, we found a position I liked, I interviewed and I got it.  I’ve been there for a few weeks now and it’s different, like when you move back with your parents after college [chuckles].  But it’s good.

So how it’s been? Has tech lived up to your expectations? What are your first impressions?

Well, it is difficult when you start at Google, is what I’ve learned. Google is tops. It really—it doesn’t get much better, in my experience. I clearly come from a very difficult background, employment-wise. It doesn’t matter how intelligent I am, or how hard I worked, there was always a problem. And Google was the first place that I’ve worked where no one gave a shit. No one cared at all. And it was funny because I was actually sitting in one of the cafes one day, and a whole bunch of new Googlers—Nooglers—were coming off of a bus, and the first guy looked at me and was like—and you could see him running his training in his head like, “if she’s here, she’s supposed to be here.”  And I’m watching them all walk by and have this same conversation in their heads.  I know that it seems like they shouldn’t have to do this, but thank god they do. I’ve never been in a position where people self-corrected. When they recognized that they had felt something unreasonable and then fought themselves to make it right. I just felt that was brilliant. It’s not utopia, everywhere has difficulties but considering where I’ve come from, I could not have landed at a better place. My time at Yahoo was good but for different reasons. There was opportunity at Yahoo. There were things that I could do, things that I could bring to the company. But cultural wise, it’s a little more difficult because there wasn’t much diversity on campus. I didn’t have the self-correction thing. I had more just open stares–

“I clearly come from a very difficult background, employment-wise. It doesn’t matter how intelligent I am, or how hard I worked, there was always a problem.”

You mentioned that.

During my first week or so there, people just kept walking by my desk and looking at me, to reassure themselves that I’d still be there. There aren’t a lot of black people, and then I don’t resemble the ones they’re comfortable with. I used to have permed hair, I was a lawyer and would wear heels and suits and whatnot. I’m much older now and at this point, you’re going to be who you’re going to be. So I wear my little t-shirts and long sleeves [chuckles], and I wear my hair natural. And there just aren’t a lot of people like me at Yahoo. So it’s not hostility. It’s more discomfort, but it was disconcerting and really affected my decision to accept the FTE position. Because if I’m not there, then who’s there? So the culture can use a little help [chuckles], but the opportunities were there. So it was a balance. I’ve been in outright hostile situations more often than not. So a little bit of, “Oh my god, she works here?” I mean I could do without it, but it’s not going to destroy it for me [chuckles]. At this point, it’s a lot better than what I’ve seen before.

“Even in New York, people would stare at me. And I was like, ‘There’s a guy painted silver down the street. Why am I interesting?'”

It’s a blessing almost for you to be able to have that perspective, but I hate that it has to happen in the first place. You know what I mean?

Yeah, and it’s a hard fought blessing because in my twenties, it would have been different. But in my twenties it was new and raw, I was struggling with it a lot more. So to come here at this age, and for it to be this kind of struggle—I’m comfortable with it. So I kind of feel like all of the out-and-out fighting [chuckles] I basically did to hold onto my humanity on the East Coast kind of prepared me for the questioning looks of the West Coast. It’s just things are softer here. It’s not like the issues don’t exist, but people don’t tend to take it as far as obviously. It’s more abject curiosity. It’s funny because there are a lot of minorities in tech, they’re just not American minorities. It’s like, if you can accept minorities from other countries, why can you not accept your own? It’s the number one issue that I’ve had with Silicon Valley. We don’t ever seem to have a problem with the amount of women from other countries. We don’t ever seen to have a problem with brown people from the opposite side of the globe. But when you see a black person in tech or you see a program for Latinos in tech, then suddenly people are up in arms and, “Why are we handing out this and handing out that?” It’s like there’s an assumption that if people come from other countries, then they must have done something to make it. If minorities come from here, they must have been given something. I have four degrees from very good universities, so clearly no one gave me anything. You may have given me opportunity, but no one’s handing me my job. The fact that I don’t get the same credit, just to start, is frustrating. This is the life story for black women in this country for decades. So, just like those before us, you’re just kind of hoping that if you continue to do what you do, then maybe it will be easier for the next.

“It’s funny because there are a lot of minorities in tech, they’re just not American minorities. It’s like, if you can accept minorities from other countries, why can you not accept your own?”

You have a super interesting background. You have degrees in multiple disciplines. You’re so well-rounded and you come from the other side of the country, like myself. You didn’t go down the typical path at all. More and more, there are conversations around how being unique and being different makes you such an asset, in terms of contributing to a team or bringing perspective to a product. How do you think that impacts your approach to work and makes you bring something to the table?

Yeah. Well, I’ve always been a contributor. I enjoy being on a team. I appreciate that dynamic. My first stint at Google my diversity in intelligence, I guess, made me a leader.  Amongst my group at least, because they appreciated that I could see different sides of an argument, and because it makes it—I become like a translator. Especially since my first Google team—my first team at Google, there was me, a woman from Japan, a woman from Brazil, and an American girl with—she worked with the Canadian market.  So we all had very different understandings of the same sentence, and I could understand all of their understandings, and help them explain them to each other. And so I tend to bring value in that aspect, and people tend to be open to that. As far as it translating into a wider contribution to the company, that’s more difficult, because people are rightfully to some degree concerned about their position, and there’s always a difficulty because people think that you have the same motivations they have. And so people who are motivated by position are always concerned about other people trying to take theirs. If you have a good idea, or a good approach or something like that nature, they’re more concerned with how it affects them ultimately. ‘Will she come take my spot?’ But that’s a position I’ve always been in so I’m very comfortable with that– people thinking that way. It’s unfortunate, but that’s what my norm has been. I value Google. I value Yahoo. I value these companies that play a daily role in my life. For me it’s not really about, ‘Oh, if I do this I get to move here or do this?’ No, it’s about, ‘If we make Yahoo stronger it helps all of us.’ Yahoo seemed to be pretty open to using me in a variety of ways. I’ve only been back at Google for a few weeks but from the conversations we’ve had thus far, they’re open to using the talent I have in the ways that best benefit the company. That’s why I value Google, because that’s a philosophy I can believe in. We’ll have to see if it follows through, but I don’t really have much reason to believe that it doesn’t. The people who are in charge of that type of thing seem to have the mindset that I agree with, and the people who have difficulty with it don’t seem to be in my chain of command.  So, I’m not so concerned. It seems that at least in my department, the people at the top are pretty comfortable with who and what they are, and so they’d be willing to allow me to help the company when the opportunity presents itself.

“I have four degrees from very good universities, so clearly no one gave me anything. You may have given me opportunity, but no one’s handing me my job. The fact that I don’t get the same credit, just to start, is frustrating. This is the life story for black women in this country for decades. So, just like those before us, you’re just kind of hoping that if you continue to do what you do, then maybe it will be easier for the next.”

I love that you can have that focus.

At some point, I spent a lot of time fighting the expectations, fighting people’s opinions, fighting for what I rightfully earned. And I was miserable. And I didn’t get any of those things that I’d worked so hard for. The expectations were still there from one side, but people still saw me how they wanted to see me from the other, and I never received any benefit. You can only beat your head up against the wall for so long, and so then I was like, “Well, let me try and find an arena that doesn’t make me fight so hard for my humanity,” and I felt like tech was it. And it has been. While I was still a contractor at Yahoo, they still allowed me some input into some arenas that I didn’t expect. They actually took my input legitimately and forwarded it through proper channels and treated me as if my ideas mattered. And that’s the thing that I liked about Yahoo at the time, that that they still had the capacity to see human beings. It wasn’t a machine, there was still a human component. I think as long as they manage to keep that, they still have a fighting chance.

At work, do you have kind of a support network that keeps you grounded, or do you find that elsewhere? Like the LGBT community that you were involved with when you first got here?

I was actually heavily involved with LGBT ERG at Google, which is interesting because a lot of tech companies in Silicon Valley don’t allow vendors and contractors to be involved in their groups, which I think is really unfortunate. But I found a home with the Gayglers. A lot of them are still my friends, and a lot of the people who I worked with when I started are still my friends. At Yahoo, I made some more relationships. A couple of people I started friendships with. But I didn’t spent as much time on their campus in that way.  I hadn’t connected with their LGBT community, but between my old Google friends, my newer Yahoo friends, my girlfriend, and hopefully new Google friends. [chuckle] I actually met my girlfriend at Google as well.

Oh, really? Oh, man! It’s like you just found treasure as soon as you got here.

It was like the perfect place for me to start. I couldn’t—it wasn’t the place for me to grow at the time, but it was the place for me to get on my feet. And I will always appreciate it for that. Everywhere can’t be everything. I think I needed to be there to get a floor, to get a family, you know a home? But then, I had to branch out just like you do when you’re a kid. At some point you have to leave home, try to create something bigger for myself.

I really respect that. I think a lot of people a lot of people take the safe—they just stick around. You know?

Comfortable isn’t always safe and that’s what I was concerned with. Towards the end of my first Google gig, we were comfortable, but we didn’t feel safe. I felt like I could stay here and ultimately lose it all, or I can make this leap and possibly gain a whole lot. And it seems I made the right decision.

Have you had mentors, people that you know or you don’t know people that have inspired you on your path?

My twin inspires me, she always has. Our family is very competitive, and my twin is very smart, but I’m Very smart. In our family dynamics it was always difficult. She would study really hard and would get a B, and I would play around and scan the book last second and get an A. That’s tough. I don’t think she realized that I noticed that. Obviously I wouldn’t have felt guilty, this was in high school and middle school, but it wasn’t that I didn’t understand that our situations were different. I always kind of wanted her to get what she deserved or be what she wanted. She worked so hard. She went through, for several years she wanted to be a model, so I used to help her with that dream and whatever dreams she had. Recently, she actually published a book. She had her own launch party and it was awesome. It’s a dream that she’s been working on for seven years. I would edit it, then she’d pay to have it edited then she paid for a book cover, and images, and this, that, and the other. My whole life she has worked hard to pursue different dreams and I watched her. Even when they didn’t go the way she wanted, she never just quit. She never just said, “Well, I guess that didn’t work.” She would just find another dream and pursue that one. I was always inspired by her ability to keep going. When it got difficult for me, I didn’t necessarily look back on that example but I think I always had a little bit of it in me.

Over the last maybe ten years or so, we’ve gotten pretty close, and she’d call and check-in at the most opportune times [chuckles]. Just encouraging words to keep me moving. She had been trying to get me to leave Florida for some time. The last time I went down and it didn’t work out she was over it [chuckles], and so when I actually decided to go, she was all—”You need to come, you need to come here. It looks like you need to come here.” When I got the job as a vendor at Google, I couldn’t work out the housing situation since I wasn’t getting paid anymore, and she was like, “You can just stay here for a couple of weeks. My roommate will be fine. You’ll just sleep on the couch.” Even when I started working there, I still had to get finances together and get housing, and she would send me a little money here or there or talk to me and keep me focused. And  basically she’s kept me from being a hothead over the last two years, which is a thing. I’m not just generally a hothead, but once I hit a point, I’ve hit that point, and she’ll talk me down and like, “Look, this is where you were, this is where you are. I know this is difficult, but this is where you are, and it’s better than where you were, so breathe, relax, and then you can make a decision.” She said that a lot over the last year, year-and-a-half. I can’t say that I have any mentors in the tech community or anything like that, but having her in my corner has been—it’s a lifetime thing. She’s given me a path to follow and she’s a positive voice in my ear and I need it.

“I’m very excited about the ability of tech companies, since they have the resources and they have the ability to train and they have the people flooding their gates. They really do have the ability to pick and choose a workforce that can be anything they want it to be, and to create a corporation unlike any that you’ve seen. They are being socially responsible but profitable and bringing something good to the world. What scares me is what I actually see.”

I’m just curious to know what you think about the state of tech in Silicon Valley right now. What are you excited about, and what really frustrates you and what do you want to see change?

I’m excited about the possibilities of—when I was in business school, they talked about transnational corporations. And it’s like a new form of corporate entity, how you do business, how you see the world. And it’s really only possible if you, like a tech company, bring people in from all over the world and make a global focus your focus. So it’s not about diversity as in this many people of these people and this many of these people. It’s a diversity that’s bigger than that. It’s diversity of thought, diversity of focus, and how you approach problems in situations. So I’m very excited about the ability of tech companies, since they have the resources and they have the ability to train and they have the people flooding their gates. They really do have the ability to pick and choose a workforce that can be anything they want it to be, and to create a corporation unlike any that you’ve seen. They are being socially responsible but profitable and bringing something good to the world. What scares me is what I actually see.

“We have this idea of, everyone was a nerd, so why would there be bullies?”

That people are people, and when an organization gets large enough, they’re going to have a certain amount of people who are there for reasons that don’t align with the corporate strategy structure, vision, and mission. And allowing those people too much time and too much power can ultimately destroy an organization. You lose your focus. You lose your good people. And it scares me because it happens when it doesn’t have to. Companies that don’t necessarily need to cut cost, use contractors with completely opposing visions to cut cost. But you don’t need to cut cost. So why would you affect your work pool in that way? And so I see talented people moving from company to company to company, because the vision that they thought the company had when they came in was not the reality the C-suite built. And so I’m talking to different friends of mine who work in different tech companies, and the atmospheres are not what people outside of tech think they would be. We have this idea of, everyone was a nerd, so why would there be bullies? All of us got overtalked in high school and elementary school, so why would we overtalk people? You figure that this would be the one arena where you would know how to treat people, and care to treat them that way. And that’s the dream of Silicon Valley, for all of us who are coming from wherever, when we come here. But then we get here, and it feels a lot like the East Coast, and that’s demoralizing. Because if we can’t be better in Silicon Valley, we can’t be better. Where else in this country are we ever going to have this opportunity where there are enough resources, enough jobs, and enough companies with missions that aren’t just money-focused? There’s nowhere else in this country where we have this ability to be better. So if we can’t do it here, it speaks for all of us. And it’s scary. And so that’s—my biggest fear is that we won’t recognize that we can do better, and we’ll be mean girling in the cafeteria at a tech company in Silicon Valley, when all of us grew up on the other side of that. There shouldn’t be a place for that here. This is really our only safe haven, pretty much tech and academics, and if those two go down, then there’s no safe space for the square pegs and that’s a scary proposition.

“If we can’t be better in Silicon Valley, we can’t be better. Where else in this country are we ever going to have this opportunity where there are enough resources, enough jobs, and enough companies with missions that aren’t just money-focused? There’s nowhere else in this country where we have this ability to be better. So if we can’t do it here, it speaks for all of us. And it’s scary.”

Yeah. This is supposed to be the place where you can be an other.

Yes. Comfortably so. Accepted and appreciated for that. I mean, I’ve seen it in spots, and then I’ve seen the complete opposite. And it’s scary when you think we may get more of that than what we expected, you know?

Yeah. I’ll be curious to see what happens. I worked in tech for a few years, and six years ago, it was way more— it felt way more weird. Does that make sense?

Mm hmm.

It doesn’t feel so weird anymore.

Way too normal.

I don’t know how I feel about that.

It’s becoming way too normal. I shouldn’t stick out at all, you know [laughter]? I really shouldn’t. That’s the whole idea. That was what I loved about when I first got to LA. No one looked at you. Even in New York, people would stare at me. And I was like, “There’s a guy painted silver down the street. Why am I interesting?” But when I first got to LA, no one cared at all. And I just thought it was the greatest thing ever—that I could just be.

Yep.

But more and more, I’m becoming a thing again, and that is not what I expected. Nerds should be more open and accepting [chuckle]. So that’s been a bit of a concern. I don’t know how long it’s been going on because I’ve only been here a year, but I’ve felt it in the time that I’ve been here. And that’s disconcerting.

Going back to something you talked about earlier. People talk a lot about the hiring problem and the pipeline problem and the addressing diversity issue from a hiring perspective, but I’m also really interested in retention. And that’s not talked about quite as much. You’ve got people coming to the industry. They’re coming, but you’re losing them, like you said. I’m curious to hear your thoughts as someone who has this perspective in consulting and business strategy, and your thoughts around how are folks missing the mark in terms of talent retention.

They’re making it too complicated. It’s not that hard. Just don’t make me feel like I’m not supposed to be here. I’ve worked at two pretty big tech companies at this point. And the biggest difficulty that I’ve seen is most of the diversity is going to be in your contractor and vendor pool. There are more Black people working as contractors and vendors at Google than as FTEs. There are more of us working as contractors at Yahoo than working for Yahoo. So a lot of these companies don’t necessary have an issue with minorities. But they create a pretty clear line between contractors and FTEs, which creates a separation between your largely minority force and your largely majority force. And so you end up in a situation where everyone who looks like me is probably a contractor, so nobody pays attention to you. And you end up with full-time employees who are treated like contractors because that’s what people see. If the majority of the contractors are minorities, and the majority of FTEs aren’t, then “If you’re a minority, you must be a contractor, I don’t have to pay attention to you.” So it’s a structural way of internalizing these attitudes and beliefs that we didn’t intend to foster. There’s no real need for that.

I mean, your contractors work for you. You can’t do your business without them. They’re not necessarily less intelligent. I know that because I have four degrees and I’m a contractor, so clearly we’re not inferior beings.  But the issue is the need to create an entitled position socially. You already have stock options. You can go to the health center. There are already things that you can do that contractors can’t do. So, the fact that you have to create this ‘we’re better than you’ atmosphere necessarily injects some level of discrimination into your company that didn’t have to be there. I mean, it’s one thing to have different badges. No one really cares until it becomes a thing, until I’m walking on campus and I see someone look at my badge color before they say hi to me or don’t say hi to me. Or before they walk past me like they don’t see me. Those things aren’t necessarily racist when they’re set up, but if I am one of less than 2% of black people on your force, but your contractors have plenty of black people, all of a sudden now I am an ‘other’ because everyone thinks that I must be a contractor. It just makes it more complicated.

Just have your work force treat everyone like they’re okay. Say hi to anybody that walks past you. Speak when you’re spoken to.  Just basic human sensibility, and you can keep your minorities. Nobody’s asking for extra. Nobody wants a handout. Nobody needs special treatment. We just don’t want to be treated poorly. I think there’s this anxiety around the issue, and it makes people do a whole lot of things, but they don’t do the basics. So you’re having these courses, and you’re having these talks, and oh, let’s have a seminar, and a symposium, and let’s do this, and write this article, but when you walk around campus, do you say hi to each other? When you’re sitting in a meeting, do you notice when someone has something to say? When they say that thing, do you actually listen to it, and comment based on what they said, or do you just run through it like they didn’t say anything at all? Just basic human sensibility will make people want to work for you. But when you make it us versus them, then it’s more complicated, and then you have to try to force people. “Don’t treat these people worse than…” And so now people are actively trying to be overly friendly, which is also disingenuous, nobody wants that. I don’t want you to say hi to me because I’m the black chick. I want you to say hi to me because I’m on campus and I looked you in your face. That’s just basic. We manage, but it’s this whole– I work for, you work at, and that sense of entitlement has permeated all the Tech companies that I have even spoken to my friends about. And all those Tech companies have diversity issues.

“It’s not that hard. Just don’t make me feel like I’m not supposed to be here.”

Whoa. That’s just like a totally new systemic issue to me that is blowing my mind right now. It’s almost like, it’s creating—and I’m sure it’s not on purpose, but it’s created the system in which discrimination can be quietly applied to an area of tech that is not necessarily stigmatized and that’s crazy. It’s crazy.

Do you remember the situation where minorities are afraid to speak to other minorities? Because it’s like, “If I speak to you and you’re a contractor, they’re never going to believe I’m not a contractor.” Now you’ve created dissention within the minority groups because nobody wants to be connected to someone who is lower than them because people already want to think that they’re lower. So it’s just highly unnecessary, just speak, just work, just be kind to one another. It’s not that complicated. Teach manners in these intro classes. Teach cross-culture communication. People who grew up in this area think of things this way, the east coast sees it this way, the west coast see it this way, this country sees it this way, that country sees it that way. Know that while everyone won’t fit into those individual groups or sets, you may want to be cognizant that people from this country may speak about things in this light, or it may be more effective to explain it this way. Just teach people how to communicate with each other, and how to be kind and people will stay. We like our jobs, everyone who comes here likes their job. We just don’t want to be tortured and we don’t want to be a zoo animal. [chuckle] We don’t want to be petted, randomly, by people who think it’s their job to pet you. We just want to be a human and go to work every day. That’s all you want to do. It takes an effort in communication and understanding that everyone here deserves to be here. No one’s handing out jobs, to anyone, from anywhere.

“Just have your work force treat everyone like they’re okay. Say hi to anybody that walks past you. Speak when you’re spoken to.  Just basic human sensibility, and you can keep your minorities. Nobody’s asking for extra. Nobody wants a handout. Nobody needs special treatment. We just don’t want to be treated poorly.”

Lordy. People are treating it like it’s a zero-sum game. You are not taking something from someone, by being present.

That is also a difficulty.  The, “Oh well if we hire these people there’ll be less of—” No there won’t. There are still jobs, they’re still hiring. I hate the argument every time you say, let’s diversify. People say, “well we don’t want to lower our standards.” Did you lower your standards for me? Because I believe that I out-degree most of the people at my company. So it’s just this automatic assumption that we need a handout when it’s not that. The issue is, I have 4 degrees but I may have never been interviewed. How many people like me are out there because you want to interview people who you know and you understand and you feel comfortable with? Well, for the good of the company, maybe you should expand who you know, who you understand, and who you feel comfortable with. I’ve spent a lot of time traveling. I’m comfortable with pretty much anyone, pretty much anywhere.

“How many people like me are out there because you want to interview people who you know and you understand and you feel comfortable with? Well, for the good of the company, maybe you should expand who you know, who you understand, and who you feel comfortable with.”

A lot of people don’t travel.  Or they’ll travel with their friends to specific places that feel an awful lot like home.  So you don’t actually get a view of the world or meet different people or learn different things. It’s not that you’re actively not hiring women or any other minorities, it’s that you don’t know them and you can’t communicate with them. So you’re afraid of them and you’d rather not have them in your closer circles. That’s why teaching basic communication, teaching basic human kindness would make it easier to hire and to retain minorities of all sorts.

There’s is some media syndrome and I don’t think we understand it. You see it every day when you check Facebook. It’s like people feel like it gives them some sort of, I don’t know, intelligence credit. If they can just shoot people down and be hateful all the time. It’s like a new badge of honor of some sort, you know to be mean and unreasonable and just to hate [chuckle] for absolutely no reason. I don’t understand it. Life is really short, like really short. And I can’t waste time for any of it. I won’t waste time for any of it. I think by the time some of these people realize how short life is, they will have blown quite a bit of it. Just wasting life experience.

Yeah. I don’t think it works long term. I’m not convinced.

[chuckle] Maybe you won’t become a bitter old person. When I was in high school we were having a school function outside at my high school and I think there were older people.  I was standing outside waiting for my mom to pick me up, and a couple of them walked out and they were nice and they said hi or whatever. But two or three of them were just mean, just went out of their way to be mean to me because I was the youth and I was this and that, you know “kids these days.” And I was like, “How are you this bitter when you’re this old? Have you always been bitter?” But it’s just a horrible way to live. It’s like, even if you’re physically kind of crippled as an older person, if you’re kind, it changes the whole appearance of your face. It changes how the room feels when you’re in it, and I would rather go out like that than cussing the gods [chuckles] with my last angry breath. It just doesn’t seem to be worth it. Especially since you work in tech. How bad can it be [chuckles]? Really? This is like Disney World. How bad can your life be? They pay good salaries. The housing is expensive, but it’s nice. You can afford it on your salary. The food is good. You can get organic and whatever special stuff that you crave for a reasonable price. They will deliver anything from anywhere to your door at any point in time. You can go off the grid or use Google’s fiber or their phone service or anything else, anything that you want is within a dial of your phone. Wow, why so angry? [chuckles]

I so understand. I think perspective helps.

Yeah, I think it does.

Where do you think you’ll be in five or ten years? Do you think you’ll still be here?

Oh, no [laughter]. No, I’ve got plans. I wanted to do tech for a long time, and I have a set period of time that I want to spend specifically in tech solely. But I had dreams before I came here. So this was a dream that I wanted to fulfill, but it’s not my ultimate dream. Well, part of it was. Working at Google was an ultimate dream, but I’ve done that. So that’s cool [chuckles]. But yeah, I have things that I want to do with my life once this phase is over.  I’m not a lifer, but I don’t think I’ll ever truly leave tech. I was always kind of in it anyway. So this is a very important chapter in my life, but it won’t be the only one.

I’m excited to see what happens, what you end up doing. My last question for you was going to be what advice would you have to people who face similar struggles to you who are hoping to get into tech?

Don’t listen to anyone or anything. Well, listen, but always give yourself the final say. I don’t have a single tech degree [chuckles]. I came here to do a General Assembly course in UX design and it all fell apart when I was on the train in Texas because I couldn’t find housing. But I’m still here and now I’m in my second stint at Google with greater responsibilities. So it is possible.  If you’re willing to put in the work it is possible. You may have to go a different route. You may have to do some different things, but just don’t let someone else dictate to you the path that you need to take to be here. I had several people who I was trying to have as mentors who tried to tell me, “Do it this way, do it this way,” but they weren’t ways that fit what I wanted for my career and for my life. And I appreciated that they were trying to help me, but I had to do it my way, and I’m very happy that I did. Oh, and it will not be easy.  There will be traps and pitfalls, the rug may even get pulled more than once.  You can’t help what happens to you.  If you get hit hard enough, you will fall.  But you can control how you fall.  Always fall forward.  Take the blow.  Allow yourself the hurt.  But never go backwards.  Fight to fall forward and you’ll always have a reason to get up.

“You can’t help what happens to you.  If you get hit hard enough, you will fall.  But you can control how you fall.  Always fall forward.  Take the blow.  Allow yourself the hurt.  But never go backwards.  Fight to fall forward and you’ll always have a reason to get up.”