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.

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 am originally from North Hollywood, Los Angeles. Most of my early childhood and K-12 education was in San Fernando Valley. After high school, I moved to Japan for a decade-long stint, but upon returning to the Republic of California I have been traveling to/from Japan almost every 2-3 months for the past 16 years.

How did I end up in Japan? During my senior year of high school I was not sure what I wanted to do. Fortunately, I had many older friends in the animation industry, places like Disney; and the exposure piqued my interest to work in the animation industry. At the same time, there was a recession in the United States and a friend two years my senior, Ken Olling, told me I should move to Japan. He was already there. Given where LA was heading, I told myself, “Why not? Let’s do it.” and leaped from my cliff.

Through a series of autodidact experiences, I went from animation and storyboards to graphic design. From information design, to product management, to lecturing at Berkeley’s Haas School of Business,experience design, to product design. I did executive management and leadership for Fortune 500 companies and startups, before founding my own two hardware startups. Recently I have been helping at Stanford’s d.school, mentoring LGBTQ entrepreneurs, and advising a companies on the future of VR/AR peripherals, and bespoke rich retail operations with analytical insights, and home artificial intelligence.

What elements of it are the most exciting and engaging to you? What really activates you?

Some designers just like creating. Some designers like to create for the sake of getting their work out into the world. Some designers want to create work that persists so they can say I did that.

For me, I want to find the fundamental need and design to fill what is lacking. The most gratifying part is, finding a need, finding a way to create something that would delight, and wow, and make the end users smile when they experience that creation. What keeps me happy is knowing having the users love that creation as much as the team and I loved making it.

“I’ve never been one for conformity, or labels.”

Let’s go to the darkside for a minute. What has been some of the biggest struggles and roadblocks in your work? Either specific to a job or in the rest of your life.

Professional hard aspects were learning the grit and tenacity that’s required to try to raise venture capital as a queer entrepreneur. You know, I cannot say that I have had the darkest career experiences. Honestly, I think these and other previous hardships at Apple would be those experiences that consistently made me unhappy, but have galvanized and hardened me making me who I am today. I enjoy what I have done and absolutely love what I am doing. I am excited for what’s to come as my go forward.

What’s your experience is being a techie in the queer community?

There are levels of acceptance for nerdy and queer persons in the tech community. I’ve never been one for conformity, or labels, and I’m a staunch advocate for LGBTQ diversity and inclusion. Often times the Queer community in The City can be overly too serious and catty in acceptance of us outliers. Even CIS women can be quite catty, where I’ve recently run into this in women’s restrooms.

LBGTQ within the techie communities has been warm and welcoming, and very supportive, with the exclusion of fundraising with some VC’s. Sometimes the investment banking world has an unfortunate bro-culture within senior and midlevel partners. Younger generation VCs seem to be the exclusion. Where are the Queer VCs and funds? (laughing) 500.co and Women’s Startup Lab are the exceptions as they brand out advocating for these areas, I believe.

“LBGTQ within the techie communities has been warm and welcoming, and very supportive, with the exclusion of fundraising with some VC’s.”

My extraordinary queer corporate experience was great and I’ve seen support grow and flourish since 1994. My early days of Macromedia was extremely welcoming and inclusive. Adobe with their legacy Aquanet (Aldus days) queer community originating in Seattle and Apple Lambda have been safe environments. Sony when initially joining, I actually felt threatened, but through love and management support from my team in Sweden (Sony Mobile) and Japan (Sony HQ), we were able to work to ensure a safe and inclusive environment along with a successful corporate HRC index ranking. Throughout my time as executive leadership at Sony, we helped LGBTQ expatriates find safety and security in the San Francisco Creative Center studio. I affectionately referred to this as our LGBTQ underground railroad from Tokyo.

Unfortunately, the progress my team and I made in North Carolina at Sony Mobile and Research Triangle Park just took major bounds backward this past week. I stand with my brothers, sisters and others who are being put in harm’s way if North Carolina’s governor signs hate into law.

Trans people, especially trans women of color, are already at dramatically greater risk of violence and murder and policing restrooms sends a message to those who would do us harm that such behavior is condoned.

We, like everyone, deserve to live under laws that protect us from harm, not inflict it. 

“The biggest reason behind me not fully transitioning was fear for my 26-year career and financial implications for my family’s future.”

You’re the first trans person that I’ve interviewed for this project that hasn’t transitioned, and I’m curious if people feel the need to put you in a certain bucket or category trans-wise and have a hard time with it. Does that make sense?

[Editor’s note: Since this interview, Ana has decided to move forward with her transition, and this question has been edited. CONGRATS ANA!!!!!]

People have a hard time because of my size, age and need to categorize. I am 6’2’’, 300 pounds, and 43 years old. I am not a young, petite woman that is early in her career. I choose to manage my life circumstances accordingly. That said, transitioning means something different for each transperson from SRS to everything in between, changing their outward dress to align their heart, body, mind, and soul.

When we first spoke, Helena, the biggest reason behind me not fully transitioning was fear for my 26-year career and financial implications for my family’s future.

Since our initial conversation around this project, I have gathered my internal strength, focussed on bravery, with the support of my family and global community of loved ones, professional network, and have fully transitioned to a woman. I told myself, “Why not? Let’s do it.” and once again, leaped from my cliff like times before when moving to Japan, or starting my first two hardware startups, leveraging my core beliefs in Swagger & Whimsy, Humor & Tenacity, Creativity & Grit, has made this journey all the more rewarding. It’s a slow and steady experience and this project was the catalyst for my courage and my platform for the transition.

Dearest Ina Turpen Fried, you’re my muse, mentor <3 thank you for helping through my transition <3

What do you foresee happening to tech and design in 2016?

For me, 2016 is about heritage. It is about building products that are authentic and built to last. Like Le Creuset cookware, or KaiKaDō tea caddies we should craft technology and products that will not end up at the top of the e-waste pile every 6 months. That will be a major macro-trend for 2016. From a tech and design perspective, I liked what A16Z said as their sixteen predictions for 2016, two of which struck a chord with me.

The first one is Full Stack. Some people call it being T-shaped or being a ‘hybrid,’ being able to go deep in 1-2 areas and work interdisciplinary. It is one thing to be excellent in design, but to be successful in the future, you have to be able to know how to work across disciplines. For example, even if you are a designer and not an electrical engineer or mechanical engineer, you have become an expert in those fields to be in the trenches with them. You want to be able to communicate and understand them at a deep level to be successful. Andreessen Horowitz stated that they do not want to invest in companies or people that are not really full stack or have a full stack mentality.

The other trend that I see and am studying is the UI-less user experience. I am experimenting with UX agents that take natural gesture input, speech in particular.  Bots are the initial intelligence-singularity type of things that people will encounter. People on the creative side will need to get their heads around that whether we like it or not. It is going to be much like the movie Her. We will not be designing things that are screen or product based. Amazon Echo already does that to a degree. Siri’s not that great, but Google Voice is pretty darn good. Those are some of the big trends for me for 2016.

What advice would you have for those hoping to get into tech, based on lessons you’ve learned?

It’s a global world. People need to live abroad for a while or have done some meaningful life traveling. Through immersion, you understand other people’s situations from an anthropological perspective. Then you can better design meaningful experiences or products. You can’t do it if you’ve only lived in America. You cannot do it well if you’ve only lived in the Bay Area because our microcosm here is weird. For example, you can go to the Palo Alto area and everyone has an Apple watch. You go anywhere else in the United States, you go over in Japan or Europe, and you do not see many people with Apple watches. So we need to get out of this microcosm that we live in and actually experience the world to develop that skill set and sort of that tool set that you’ll be able to design and build meaningful experiences for the world. It is about perspective even if you may be designing for your geographic region going forward.

“So we need to get out of this microcosm that we live in and actually experience the world to develop that skill set and sort of that tool set that you’ll be able to design and build meaningful experiences for the world.”

I was born and raised in Michigan in the Metro-Detroit area. I was adopted and grew up actually quite privileged—my dad’s a lawyer. Growing up, I’ve never necessarily wanted or needed to want anything. But I definitely went through life questioning my gender which stemmed a lot of misguided anger that I have—at least I realize that now, looking back on those years.

I had a pretty normal childhood. I was definitely very nerdy and less masculine than the rest of the boys and got made fun of that and by the time high school came around, I figured, “Hey, smoking weed kind of helps me, you know, fit in with everybody else and forget about my gender issues. This fits.”  But by the end of freshman year, I was failing by a credit and my parents decided to send me to boarding school in Utah. I have a lot of feels about how they spent this ridiculous amount of money to force me back into not fitting in and living with these terrible boys who wanted nothing but to see the humor that was me losing my temper and attempting to fight them. All this instead of critically thinking about why I may be taking my issues out on drugs.

The drug use actually did get worse when I got back home and into my early to mid 20’s where I failed college. I ended up taking a couple years off though to regroup and ended up going to Broadcasting School which got me a job a few years later as a photojournalist in Northern Michigan, which is not where you want to be when you’re a queer person just starting to come to terms with your gender.

Where in Michigan? I love Michigan. I’ve almost moved to Detroit a couple of times.

I was in Cadillac, Traverse City, and Petoskey. That’s like—[puts hand up to represent the ‘mitten’ shape of Michigan] Here, here, here [points to areas near the fingertips on the left side]

I’ve been there!

Cabin fever set in after a little while and I didn’t really enjoy the work, and I wasn’t being paid well. At that point in time, I was ready to start talking to people who were questioning their gender so I could get a little bit better perspective, and those people weren’t available in northern Michigan. So I quit my job, and came back down to the Metro area, and started freelancing video productions and web design. Started getting really good with web design and after about a year of doing that, I realized I was actually doing the thing and making a living and I was really happy, but there was still something missing. That’s when I started my transition.

My transition actually went fairly well and mostly uneventful and I wonder why. My interactions with the shittiness of other people towards transwomen and transpeople in general, have come more recently rather than originally. It actually took until I went full-time to have my first truly awful experience. I’m well aware that I’ve been personally very privileged to have had a pretty uneventful transition, up until now.

So you went from photo journalism in northern Michigan to eventually product designer in San Francisco. How did that happen?

So, the thing about video production is that it take a lot from different visual and other mediums, graphic design being one that I excelled at.  Also, I had previous web development experience in high school. Actually, as early as middle school, I was taking my lunch break to work on my GeoCities site type of stuff, but moved away from it because web technologies associated with design were terrible up until about 2010.

I knew when I quit my job that video wasn’t going to pay the bills so I spent some time re-learning web technologies. I also had this theory that if most of my productions were going to end up online and I was building the content—why not also build the frame?  I started doing both concurrently and picked up new talents such as motion graphics (which translated really well to developing interaction prototypes) along the way though, after a while the video work kinda dried up and became a side gig. I just wasn’t very good at the hustle that was needed to procure video clients and convince them of the value of that work.

The web work eventually turned into more design focused work when a client of mine realized that was really where I shined. I was able to work on a few apps and some enterprise style websites that helped pad my portfolio.

So over the course of about a year I transitioned my work and life congruously, and at that point I was just bored of being freelance in Michigan, and kinda burnt out by the hours being high and the billable hours being low. I had always planned to come to the queer and tech mecca of SF, so I decided to put that together over about 7 months and flew here with a large suitcase, a backpack and a longboard that I had yet learned to ride.

What were your first impressions of Silicon Valley? What were you expecting? How did it live up, or not live up to your expectations?

It’s everything I hoped it to be, but I was definitely able to check my privilege quite a bit, moving out here, and see that it’s not all roses, and whatever that saying is. Life is lived out here, which is crazy. I was definitely sheltered from a lot of that, until I moved out here. A lot of my friends are struggling. In the past year I’ve made two friends who are homeless, and being able to help them where I can, and being able to see the struggle they deal with on the daily—it definitely allowed me to step back and think about how I see the world, and interact with people and create art.

When you moved to San Francisco, you were making 1,500 dollars a month, and it took you four months to find a full-time gig. Describe that time in your life.

So, I tried to find a roommate living situation before moving out here, but it didn’t work out, so I ended up paying for a month in an AirBnB hostel in the Outer Sunset where I lived with about 5-6 people while I looked for a more long-term living arrangement. After about 3 weeks I ended up finding a room in Oakland for $500 a month which was super lucky.

I actually ended up coming out here a week earlier than I planned because I had an interview with Charles Schwab fall in my lap. They ended up giving me some bullshit line of I’m too good for the job or something like that, you know, it was garbage. Apparently they changed the job description and are moving a lot of their jobs to Texas. I probably didn’t want to work there anyway.

Anyway, I got settled into Oakland and I was working on job hunting while fulfilling the hours I owed my client back in Michigan. I didn’t even get an interview for another 2 months. I think I really had to hone my resume to the Bay Area compared to what would have probably been acceptable in Michigan. I spent a lot of time working with the offerings at the SF LGBT center, specifically the TEEI program and the job clubs to update my resume. I had a lot of free time so I jumped on the opportunity to redesign my portfolio website as well as go to tech meet-ups and learn and connect with people. Also, of course, starting my life over and meeting new people, and learning to skateboard.

I ended up getting connected to my now boss randomly on Angel List—the only connection I had on there and he actually reached out to me before I even submitted to anyone. We had a couple of interviews. I wasn’t entirely sold on the job at first so I was a lot less on edge in the job interview and more myself, I guess you could say. You know, instead of the caricature of yourself you put on in job interviews. I think that helped. Anyways, I’ve been there since July in a contractor capacity and they’re officially hiring me next week.

Woo-hoo! Congrats!

Yeah. It was supposed to happen within three months, but we were also six months behind schedule on launching and everything, so… [chuckles]

Happens.

Yeah.

I want to know more about Allytees.

Allytees? Did you go to the website?

Mm-hmm.

So my best friend and I had been for a while thinking about different ways that we could give something to the LGBT community. The idea is that we have a way for allies of LGBT people to show their support by boldly claiming a person close to them is trans, gay, genderqueer, lesbian, asexual, etc. on a shirt. The shirt literally reads “my blank is a blank” or “My mom is a lesbian” or “My best friend is transgender.”

Now we could do this by having pages upon pages of items in an e-commerce site with all the different combinations of relationship to identification… but that would come out to something like 500 items for the variations of one product.  We could also have some dropdown to the side that the user could select, but that wasn’t any fun. We knew from the start that we had to allow the user to mockup the shirt on the shirt itself… something neither of us had ever seen before… here you’re given a product, an idea of a product, and here’s how you can modify it within these parameters. And I still have yet to see any website do that, where you actually mock up the product on the product itself.

It actually wouldn’t have been possible for us to do it if there weren’t the fulfillment options of direct to garment printing available. And at the time there was only one, and another one kind of getting its shit together. Now there’s like ten of them, literally like a year later, there’s like ten of these companies that allow you to send them orders over an API and they’ll print on demand and send to your customers. Joe and I actually needed some help with the API integration stuff and I was able to hire a developer—another trans woman—to do it.

It was nice to be able to invest in something for my community and also help get a solid portfolio piece on two people’s resume which eventually helped get us all jobs.

That’s really awesome.

Yeah, yeah, it was really nice.

What else has been really exciting to you about your work? What really activates you about design and product?

So what’s really gotten me is that this is real now. I’m a creative for a living which is freaky as hell, but I know this and much of the work is iterative and ultimately you end at those “aha” moment that really lift your spirits. It’s kind of a gut punch—a good gut punch—while you’re standing there looking at your work going  “Oh wait, fuck. Oh shit, that’s great!” Then you’re really excited about it. And then getting other people riled up about it as well and being a cheerleader for your own work is really the thing that moves me.

Improving on previous work is huge too. Knowing that you’re always learning. Maybe by the time you launch a design already feels long in the tooth, but you figure out what to do a couple weeks or months later and start working to implement the change.

Sometimes having to rush and put out work that you’re not entirely happy with but you end up getting positive feedback from is also kind of a stellar feeling. And being able to get to a point where I understand the logical aspect of why the design is the design. And why we have to push towards moving the design in this new direction because the current design is failing to keep up with the functionality. So it’s very much a whole brain task to do product design and that works with me very well. It’s very symbiotic with my personality and my ability as I generally approach product design, and other art I do in general, from both a creative and structural/logical perspective.

What been your experience been like in Silicon Valley as someone out as trans?

The thing is, I’ve never actually had the conversation, the trans conversation with my boss.

Interesting.

I know that I’m visibly trans, but I’ve never—that conversation has never come up.

That’s cool.

There were many times I would normally just talk about being trans, but I didn’t want to bring it up because I’ve been a contractor, and it’s easier to just say, “hey, goodbye contractor” than, “hey, goodbye employee.” But I’ve never had a problem with pronouns or anything like that. It weirds me out, but at the same time, I’m aware that I’m visible, so I’m not sure what’s going on in their heads at the same time so like whether, “Do they see it or do they not see it? Is it possible that they don’t see that I’m trans?” Who knows? I’m sure that conversation will come up at some point, especially once I start looking to use my benefits for my transition. I guess I’m just gonna ride this train as long as possible. Aside from being at work, I have felt, going to networking and stuff like that has been difficult. Never had any direct shittiness from people but kind of feel sometimes like I may not necessarily belong here.  So I definitely feel more comfortable in spaces of people who are marginalized. Like the “I Look Like An Engineer” campaign that went on. I was actually on the billboard, and was able to go to that, and that felt really good to be a part of stuff like that and I try to go to stuff like that and find a better community within the tech community with other people who aren’t cis white men. [chuckles]

Where do you find your support networks currently?

In my friends, actually mostly my partners. It’s actually nice now to have—back when I was freelancing, I didn’t really have much of a separation of work and play. And now I do, and in the past year, I’ve found that polyamory is kind of my M.O. for living my life with people that I care about. I find support in my partners, and the people who give a shit about me. I’ve found a lot of love in the Bay area since I’ve moved here, and it’s quite stunning. That’s really what keeps me going.

That’s beautiful. What is it like for you personally, straddling worlds of privilege like tech, and then other worlds that are underrepresented?

That’s a constant mental battle that I have. It’s something that I think about and unpack on a daily basis. I have these breakthroughs every once in awhile, where I’m like, ‘Okay. I don’t necessarily know how to express or talk about what I’m feeling with that.” But I want to make sure that I do right by my community and other communities that may need a collectively louder voice. It’s something that I’ve been more aware of since I moved out here and  I’ve been heavily unpacking it ever since.

I think mainly I want to use my art to help the community—you know—what I’m good at doing. I’ve been asked in the past to do things like canvassing and cold calling, which just makes me uncomfortable—makes all parties uncomfortable. I want to find ways where I can contribute in the highest capacity. For example the NTCE did a trans survey last year and needed a designer for the report. They were paying in this case, but I’d totally do something along those lines in my free time if an org needed it. I would have taken the NTCE, but I’m already slammed with two product launches coming up, so it was just bad timing.

I also have my own art projects that I can hopefully contribute to the zeitgeist that will push trans people forward.

Where do you see yourself in 5 or 10 years? Do you think you’ll still be here in the Valley?

I hope so. I really like Oakland. I really like my friends that I’ve made in the past year. I really like the opportunities that I have to create not only for myself, but also for all the cute queer trans kids. It’s quite magical here.

I’m looking forward to working on a few side projects. One is a slap-in-the-face video series about trans-women doing day to day things. I also have a longer mini-series that a friend is writing about a group of trans-women that I’ll be directing next year once pre-production is done. That’s a much a larger project.

Also working on a space for queer and trans artists to sell their wares. Kind of an extension of the Allytees thing, I think we did a lot right, but did a lot wrong, and I’ve been contemplating what the new brand will look like and how it will help to pay marginalized people for their ideas.

My last question for you would be, what advice would you give to folks from similar backgrounds to you who are hoping to get into tech or just make it work?

There are many factors and as I said before I’ve been very lucky to make it where I am today, but the core tenants of my being are having a passion for something and having some semblance of confidence in my ability to do the thing that I’m passionate about. But don’t be an asshole. If you come from a home that’s well off, it’s easy to dismiss things that you don’t understand or make fun of it, or assert your dominance over it. I mean, I could have very easily been a gatekeeper-type transwoman who tells other transwomen they’re not trans enough, but that’s never cool and shit like that needs to be called out. So, Wheaton’s law. Don’t be a dick.

I was born in Redding, California. My parents lived in Hayfork, which is a small town about an hour and a half outside of Redding. My dad is a Seventh Day Adventist minister and my mother is an RN. So I grew up in a very kind of traditional, middle-class, American home. I grew up mostly in Northern California. My dad moved around a bit because of working for the church. I lived in Redding, lived in the Napa area for a while, moved back to Redding. I did junior high, high school there in Redding. I don’t know, I guess during that time I had no clue where my life was headed. I was obviously dealing with a lot of gender stuff, even at a young age. But growing up in a pastor’s home, you’re not really able or ready to deal with that. So things didn’t really connect with me on the identity front or even the career front until much later in my life. I homeschooled for a while when I was a kid. Mostly because I did really well in English and reading and those type of things, but not so good in math or the sciences, so I was constantly fighting this battle over either being really behind everyone in terms of math in school, or being really ahead of everyone in terms of reading. We would have lesson plans and I would finish and then just be sitting there bored for 25 minutes. In fourth and fifth grade that’s not a really fun place to be. So I homeschooled third, fourth, fifth and sixth grades. Went back in seventh grade.

What was it like coming back in the middle of middle school?

It was really different. Going from homeschooling we had these booklets. So you would work through the booklets and then basically for a school year you had to finish 12 of them. You could do them at your own pace, so I would actually do most of them really early, I would work really hard and finish my entire year of school in less than a year of actual school. Which was great, because as a kid it gave me much more time to read and study the things I wanted to study, and tinker with computers. Growing up I had a Commadore 64 that I liked to screw around on. It gave me the opportunity to have a lot more free time to play with things, which was kind of fun.

So you were tinkering with computers. What were the early inclinations that you may be interested in tech?

It’s one of those things that I can look back now and identify stuff, but at the time I had no clue. Hindsight is 20/20, you know? I remember in junior high once I did go back to school—- it was when the TI graphing calculators were really big, and it’s amazing because they haven’t changed at all, even now, but the TI-83 and the TI-85 I think, or whatever they were— I used to take some of those with my friends and we wrote choose-your-own adventure RPG games in the style of those books, where there would be story things that were happening and you would choose where to go. It’s essentially like what twine games are now, especially in the queer women’s community. There’s a lot of twine gaming stuff. But we were doing that on a graphing calculator and passing it back and forth in class to play each other’s little games. That’s probably one of the most crystallized moments.

I played a lot of video games and computer games. Being somewhat gender-weird and feeling like an outsider, spending a lot of time at home on the computer, and lived on message boards and in online chatrooms and in game lobbies, playing games with weird people from all over. I guess technology always kind of was a connection to other people. It was definitely me reaching out trying to connect with people like me, other weirdos. It was a way of connecting that was really easy for me. Tech allowed you to be whoever you wanted to be, which was kind of cool. I think those are some of the earliest times when I noticed that I was somewhat good. I built a Windows 95 machine by myself and would take apart computers and rebuild them. I don’t do anything with hardware now, but looking back I can see the little kernels of getting interested in some of this stuff.

So, take me from getting a Master’s in Fine Arts and Theatre, and then eventually becoming a self-taught coder. Walk me through college, and that kind of wild transition.

So I went to college after high school. In high school I played in a lot of bands and was really interested in extracurricular stuff, and didn’t really have an academic focus. I learned that I kind of liked English a little bit more than I thought I did. But the big thing that I loved was theatre. I got to college, and first quarter I decided to audition for the play that the school was doing, and ended up getting myself cast in a devised ensemble theatre piece that we created ourselves, rehearsing 20 hours a week on top of our freshman load of classes. So I really fell into the theatre.

I changed my major 13 times in college. The first time was before I even got on campus, because when I registered switched my major and my minor, and so I had to change my major before I even started classes. Then I largely changed every quarter. Sometimes it was like minor changes, like I changed my minor out, I started off as a History major with a Religion minor. I dropped the Religion minor and then I added a Photography minor, then switched and did a Photography major and a History minor. Dropped the History minor, added a Graphic Design minor [chuckles]. It was just incremental weird changes. But again the kind of consistent thing in my life was theater. I was in theater rehearsals pretty much every quarter of my college experience.

By my Junior year, I was TA-ing for the Intro to Theater class. Freshmen when they would come in or— we made people who were trying to get teaching certificates take the class. For the education students, it’s a class which helps you get comfortable being up in front of people. I was the TA for that class for two years as an undergraduate, as a Junior and Senior. I kind of realized that I really enjoyed the classroom, I really enjoyed I had that realization that ultimately I liked learning. It didn’t really matter what major I was. I just enjoyed being in class. It kind of became clear that I needed to go to grad school. I very quickly settled on an English degree with an emphasis in Theater. I declared that my Junior year, winter quarter, and I graduated at the end of a regular four-year college program, which is kind of absurd [chuckles].

I was in an honors program which allowed me to get rid of most of my general ed and just take one honors course a quarter. It was Greatbooks focused. Some of them were more scientific, some of them were more literature-focused. We had one called Pattern which became relevant later on. We read Godel, Escher, Bach and we read Flatland and we talked a lot about things that would become more important as I became a software engineer. Just in terms of pattern recognition, how you build things and build systems that talk to each other. It’s funny because because that was actually the class that I hated the most out of my entire honors course. It just didn’t seem as relevant to me. It’s funny that that’s the one that now is probably the most relevant to my work.

I Graduated in 2010 and had, in January of 2010, applied for a master’s program in theater education. One of the three programs in the nation that really focus on this,and it was in Richmond, Virginia so I moved cross-country. I’d only ever lived in California. Moved to Richmond, Virginia and did two years of graduate course work there. That’s also when I started to come out and transition. It was kind of during that time, and then graduated from there in 2012. So I went straight from undergrad into graduate work. Graduated with a master’s degree at 22, 23.

After grad school, I moved back home with my parents and promptly couldn’t get a job doing anything, anywhere for any money. I had applied for teaching positions all over the nation. I had applied for adjunct for full teaching positions. I came pretty close to one position teaching theatre, actually at my undergrad, which was a conservative, private, Christian college. It was right before, and during as I was dealing with gender issues. It’s probably a good thing  I didn’t get that job, looking back on it. So I moved home with my parents, and got a minimum wage job in San Francisco, doing customer service. I guess it was a little bit more than minimum wage. San Francisco minimum wage is $12, and I was making $14. I worked for a company called The Civic Center Benefit District, literally cleaning the streets, interacting with the homeless population in San Francisco, helping visitors to the Civic Center District find their way to the symphony, the opera house, picking up syringes on the ground.

It was not fulfilling work. It was not work I felt good about doing. What the company would say, and what the company would make us do were two very different things. They said that our job was just to advise homeless people about city ordinances. Then they wanted us to actually enforce and get people to move on and not camp in front of businesses that were paying the Benefit District money. So I really struggled with it from a moral sense, but I needed the money and I was getting to the point where I didn’t want to live with my parents any more. I had started transition. I needed to start my own life.

A friend of mine who is a Software Engineer for Intel and the Yocto project. She came down and visited San Francisco, and we went out for drinks one night. She was like, “You should teach yourself how to program. I think you’d be really good at it.” I was like, [chuckles] “Are you kidding?” I didn’t deliberately take a math class in college. I have not taken a math class since high school. My junior year of high school, and I intentionally planned it out that way. I took the honors programs that I didn’t have to take any math. She was like, “You don’t need to know math to be a good software engineer. That’s a lie.”

So she planted this seed gave me some stupid trivia question. The question was essentially like, “There’s a wall and there are two light switches on one side and three lightbulbs on the other. You start on the side with the light switches and you can only go to the other side once. You have to figure out which light switch goes to which bulb.” The solution to me was very apparent. You turn one light switch on for a little while and then you turn that one off. You turn the other one on, and you go to the other side, and you check which one is cold. There are two off; one of them is warm, one of them is cold, and then one of them is on. It tells you which one’s which. I came up with that answer in about five minutes. She looked at me and she was like, “You need to go home and start learning how to program right now.”

So I did. I went home and I started working on Code Academy and started going through their online courses. I started with JavaScript. I found out that JavaScript is really confusing and kind of difficult, and actually gave up at first. I spent two weeks on JavaScript and got really frustrated and felt like it was moving very quickly and I wasn’t comprehending stuff. All of the extra syntax and curly braces and semicolons were just confusing me. So I gave up.

It was probably another month or so later I started dating a girl who was a Ruby engineer. We were kind of talking and I told her about my experience with Javascript and she’s like, “Oh, you should try Ruby. I think Ruby would be easier for you. It would be a better way to start.” So I did.  I started with Ruby and kind of fell in love and rushed through the CodeAcademy stuff and did a whole bunch of other online tutorials. There’s one called “Ruby Monk.” I did Test First Ruby the RubyKoans. I did anything I could get my hands on that was Ruby. And that probably took me about three months or so. I started to feel like I kind of knew what I was doing.

I Went to my first hack-a-thon after like two months— I had done a little bit of HTML and CSS work in college on my own blog or when I worked with a theater company I did some of the marketing and ticket sales, so I did a very bare bones HTML site for them. This was the first actual scripting, actual programming. In November of that year, which was 2014, I started working on a web application that indexes and maps gender-neutral restroom locations called REFUGE Restrooms. Started that at a hackathon. The team that I was working with wanted to do it in Python, JavaScript, and I said, “Okay. I’ll hop out where I can. I don’t have a ton of experience with those languages.”

After the hackathon, they didn’t really want to keep going. And this was a project that I cared a lot about, and I wanted to use it to keep learning. I felt like I had gone to a point where I knew a lot of building blocks, but I didn’t know how to build a house yet. I knew how to hammer some nails and do some screws into a few boards, but I didn’t know how to actually build a table. I had gotten frustrated, but finally I had this idea. I had this thing that I could actually build. So many people, when I started to teach myself, they were like, “Oh well, just build something.” I didn’t even know where start to build something. But finally I had an idea, and so I kind of started and had some terrible best practices in the original version of it, but worked on it for a couple months and took it to another hack-a-thon and got some people to help. In February, we launched the first iteration of it, RefugeRestrooms. During the month of February we got 35,000 unique site visits. And we were featured in AutoStraddle, Bustle, HuffPost Gay Voices, Advocate.

Awesome.

Mind you, at the same time I was working full time at this minimum wage job. I was pushing code in the morning before work. I usually worked a 2:00 to 11:00 PM shift. I was pushing code during my lunch breaks. I was pushing code after, on the way home on BART. I was coding until 1:00 AM, making bug fixes, because people are complaining about stuff, and then going back to work the next day. I was working eight hours at my job but then a full total of like 14 or more hours a day actually on this. My job really wasn’t well supervised, so I snuck into the library with my computer and pushing code while I was getting paid to clean the streets of San Francisco. I was working really hard. It was really exhausting. I was responding to press inquiries on my way walking to work. It was absurd.

I got to the point where something had to give. To get to the next level in my software engineering I needed to get paid to write code. I needed to spend all day writing code instead of spending all day trying to do other work. I started applying for jobs and applying for internships and entry-level positions and didn’t make a whole lot of inroads. Almost had a job with a non-profit, but they decided to go with someone who had more experience. I actually posted on Twitter. I was like, “Hey, I need a job. I work hard. I’m a self-starter. I completely taught myself. I launched this project from scratch. Someone take a chance on me.” I got a bunch of responses. Some of them started to go somewhere, some of them didn’t. but got a response from someone who worked for a small startup about 16 people—YC funded. They had just raised series B. They usually worked with interns from a school, and they were getting ready to have a new intern term, but they were open to hiring an intern not from a school—and asked if I would be interested in that. I said yes. I did a take-home problem for them. Came in, did an interview with them—an in-person interview for half a day. A week later they gave me an offer, and the offer was over twice what my salary was at my old job [chuckles]. I tried not to say yes too fast [chuckles]. Gave a week’s notice at my old company and very quickly moved into tech. My last day of work working at my old company was Sunday, and I started at the new company on Monday.

Found myself doing this six-month internship at a company that has actually ended up doing quite well. I work for a company called FutureAdvisor. We were acquired in October of this last year by BlackRock—the largest financial asset manager in the world. After being an intern for six months, I got promoted to full time very quickly as teams grow and change.  I am now the most tenured member of the front end team. There’s only four other engineers who have been at the company longer than me—which is a cool feeling [chuckles]. Yeah.

Tell me what you were expecting to get out of tech—you were hoping to get out of tech, and then tell me how it’s changed your life?

The biggest thing I was hoping for was a little bit of stability. When you’re working minimum wage, trying to live in the Bay area is really hard. Stuff has gotten even more ridiculous over the past couple of years, but even three years ago, it was still pretty ridiculous. I had an amazing deal for housing. I had a two-bedroom apartment in Berkeley that I was sharing with someone, and it was 1,300 dollars for the entire apartment, for the two-bedroom. I was paying 650 plus utilities, so my rent was 700-something. My take-home from my minimum wage job was 1,600 dollars a month. Almost half of my paycheck was going to rent. Then commute bart into the city, that’s about 250 bucks a month. Food is another 250 bucks a month, if you’re living really bare-bones, which meant I had 200 dollars a month of squeeze room. That’s exhausting. That gets exhausting to live that way.

Being trans, and having trans health care needs that are more expensive that a lot of insurance still don’t cover. It’s gotten better, but you just have a lot more extra expenses. So, I was really struggling, and so I was hoping for some amount of stability, being able to start to craft a life for myself. During this whole process, I ended up having a lot of housing instability. My roommate was going to leave the lease, and I could take over and get my own roommate to come in, which I was really excited about. And then, five weeks before the lease was up, he was like, “So, I decided to stay, so I’m showing somebody else your room today.” And I went, “Oh, okay. Well, I guess I’m looking for someplace else?” I’d been subletting the room from him essentially, he was the main lease holder. I subleased a small basement room in Bernal Heights for a few months. I lived in a warehouse in San Francisco for a little bit. I moved three times within the space of 1.5 months, which was really brutal and exhausting.

So, I’ve finally kind of gotten to a little bit of a more secure spot. I make a lot more money each month now. And working for a company that got acquired, I had suddenly extra money that I had to figure out what to do with. Two years ago, I didn’t have any money saved for retirement. I have $80,000 in student debt, so it’s really I’m just really swamped. I’ve started to make progress on my student loans. I had student loans at Sally Mae and student loans at the government. I’ve now completely paid off the Sally Mae loans, so I just have the government loans now. I actually, with my acquisition money, because I had already hit my one year cliff when we got acquired. I used that money as a down payment on a house. So, I’m a homeowner in the Bay Area now. And as long as I make my payments, I have housing stability for the rest of my life. I’m still getting extra stock payouts every month, and there are bonus pools built into our acquisition deal and stuff. And if those things work out in my favor, I could have the house paid off by the time I’m in my mid 30s, which is absurd.  There’s no way I could have even conceived that.

I was working minimum wage, did not have good health care. My deductible was 1,500 dollars. Surgery was a pipe dream. Being able to get bottom surgery. Suddenly working for a company that has really good health care, because it’s in tech, and they care about employees. My deductible is 200 dollars. My max out of pocket is 2,500 dollars. I got surgery for 2,500 dollars, which is absurd. It’s absurd. To go from, that wouldn’t have ever been a possibility for me, to suddenly, it was within my grasp. It was one of those things in my wildest dreams, I hoped could come from taking a career change in tech, but you have no clue. You have no clue what’s going to happen. Being someone who’s trans, being a trans woman, there’s a lot of prejudice, so you never know if you’re going to even be able to get a job in tech. You hear that things are somewhat better in tech. You never know, right? And I do think I kind of lucked out that my company really makes an effort for diversity. When I started there were five engineers and counting myself, three of us were women. I guess six counting myself so half of the team was women. That’s absurd, like that is absurd in startups. So, I kind of lucked out and I think finding the right spot I could kind of thrive in, it’s not been without it’s difficulties. As the team has grown and changed and brought on more people and new managers come in and whatever but…yeah.

This is such a good story. I’m so happy for you. 

It’s been really incredible.

I want to know more about your experience as being trans in tech. I also want to know what it’s like being someone with anxiety and depression in tech. I’ve talked to several trans folks in this project and I’ve also talked to a lot of folks with anxiety and depression. I want to know more about both of those for you.

Sure I guess I’ll talk about the anxiety first.

That is something on a day to day basis that does affect me. For awhile, I was pursuing getting actual medication for it. Let’s see. I’m trying to figure out the best way to get into this discussion. Maybe the best way is to, again, talk about the difference from working at my minimum wage job before to now.

When I was working a minimum wage job and I had a really bad mental health day, I still had to try to go to work. I still had to wake up, force myself to get out the door, because I literally could not afford to take a day off. You only have so much vacation hours, you only have so much sick hours. So, you literally can’t afford to take time off. You’re also in a situation where because of money situations, your anxiety is increased. So, it’s a tightrope walk. Right.

Getting a job in tech alleviates those money concerns. Like, my team has a “unlimited paid time off” policy. We also have sick days that our policy is, if you are not feeling well, don’t come into the office. I haven’t explicitly talked about mental health stuff with many of my coworkers, but the culture of my company is where somebody just sends an email and says, “Hey, I’m not feeling well. I’m going to work from home today,” or, “I’m going to go home,” they’re not met with a lot of questioning of that. In many regards, it’s a much healthier place.

On the other hand, though, the stakes of my job are a lot higher now. Before, I was getting paid to pick up syringes off the ground. Whether or not I picked them up today or tomorrow, there are going to be more syringes tomorrow. There’s going to be more trash tomorrow. It’s a never-ending process. If someone wasn’t there to tell a homeless person to move down the street, I actually felt better about my day. Versus, I work for a company that, we have millions of dollars under management.  We now are working with BlackRock— are working on major, major business deals. Our first business to business deal was announced a couple months ago. So we’re now partnering with other large banks to provide our service to their customers. That’s incredible, right? We have millions and millions of dollars under management. The stakes are all higher.

Granted I work on the framing mostly and I’m not dealing with the back-end algorithm that could really mess up someone’s financial future for the rest of their retirement. So the stakes are a little bit lower for me. But tech is a very fast-paced world. It’s go, go, go, go, go, go, go, which I think can be really hard as someone who struggled with anxiety and depression. I don’t know, I guess it’s been a mixed bag for me in terms of that. It’s been really rewarding to work on a team where I’m respected and where my opinion is valued and where I’m seen as someone who knows what I’m talking about. From a depression sense, it’s good to work at a place where I feel like my work is important and valued. We’re not working on Uber for ice cream cones. We’re working on something that, I think, is making the world a better place. We’re making retirement more accessible to people who couldn’t get there without us. That’s been something that’s helped my depression. Definitely.

Being able to create stability for myself has helped immensely. Being able to buy a home, being able to get surgery— those are the things that qualitatively improve my mental health, vastly. Since I bought my house—granted it’s only been a couple months—I bought my house in November, but my level of anxiety and depression shot down immediately. I’ve been a medical marijuana patient for a year and a half or two and used that to treat a lot of my anxiety. I was on Lexapro for a while, but realized that when I tend to have anxiety attacks, I tend to forget to take my medication. Which, taking an SSRI every day, you have to remember to take your medication. And so the way that that was treating the way that my anxiety manifest wasn’t really actually very helpful. But the amount in which I’ve had to medicate My anxiety and depression has dropped enormously, especially recently, which is great.

I think in general, people who work in tech, people who are engineers, are weird people. We are the people that are on the autism spectrum, we’re the people that struggle with anxiety and depression. So I feel like when I go to work, I’m working with people who, on some level, even if you don’t talk about it, they get it. They get when you’re having a hard time, they get whatever. Which is very different than I feel like working in some other sectors, because again, the people who developed good computer skills and learned how to talk and work with machines, are the people who didn’t have good people skills growing up [chuckles]. So they were the weirdos, with anxiety and depression, who didn’t want to go out and socialize and hang out at parties. They’re the people who just go home, and cuddle on the couch and watch TV every night. So I feel like tech has been a good place for me as someone who struggles with anxiety and depression.

Again, I think my viewpoint is probably a little bit skewed because I work for a company that I think is really positive. I also didn’t have to do a transition at work. All of my documentation and stuff were changed before I got into tech. I just came in with all of my documentation saying Teagan, with everything saying Teagan. I didn’t have to try to transition on a job place and come out to people. I just started work. I don’t keep it a secret from people. It’s pretty hard to because— I don’t know, I wrote this web application that indexes and maps neutral restroom locations and if you Google my name it’s the first thing that comes up. This advocate article with me. Whatever disillusioned hope I ever had of being stealth or whatever is not something that’s a reality for me. And I wouldn’t want to be anyway. It’s not something I bring up with people a lot, unless I become friends with them through the workplace, but I don’t try to hide it.  If it comes up in casual conversation, like I sometimes just say, ‘Oh, you know, because I’m trans, like blah, blah, blah this thing that I deal with’ or whatever.

I will say the acquisition process was a lot more stressful because of being trans and specifically because of healthcare. We had a really good health clinic and healthcare plan and policy for trans healthcare. I had already scheduled my surgery. Everything had been approved. Everything was in place, and then three months before surgery we get acquired. So suddenly, all of that is up in the air. When I’m having conversations then with my superiors about how I’m feeling about the acquisition, I have to be blatant and upfront about, ‘Look, these are all of the things.’ Where other people are just being concerned about money or about if they’re still going to have their job or whatever, there’s all of these extra levels of concerns that I had. Going from working a small San Francisco startup to a huge mulitnational corporation— it’s very different. In terms of how trans people are treated, you never know how that change is going to happen. So it made the process leading up to surgery be really stressful. I was not productive, and it was just from a very logistical standpoint of that all of our benefits suddenly changed. And so there was disability stuff to figure out, and there was leave stuff to figure out that then all had to be redone, and rechanged, and refiled, and you’re working on the clock. Right, because our benefits changed over January 1st, and my surgery was January 19. So that was an exhausting kind of moment. In general though, I think it’s been really good.

There’s another kind of genderqueer person who works at my company. There are two other gay men— so our engineering team is probably about 21 or 22 right now, 22, 23. Four of us are LGBT, so again I think it’s a little bit of an abnormal sample, not representative of tech everywhere. But it’s pretty cool, right, to be able to go to work and be seen by your co-workers. You know, there were other people at my company. So working in a really nice diverse workplace, I think has made it fairly easy to be trans in the workplace. I do notice some elements of— I feel like it’s been kind of creeping up as we grow and become more corporate in our culture, that men’s voices are being heard more than women’s voices. I think we’ve done some hard work to make sure that’s not the case. We have three, four engineering teams, one of them is managed by a woman. Our director of Algorithms is a woman. I’m the most senior engineer on the front-end staff, so we’ve done well and we’ve hired additional women, but I do notice management tends to pay more attention to the male members of the team, and it’s not— I don’t know. I don’t know, maybe it has gotten to the point where people are actually getting paid more than other people. I don’t know. Salary is such a weird thing in tech.

Maybe one last question would be, what kind of advice would you have for people that have faced similar struggles in either gender confusion or poverty, or all of the things you’ve been through, what are the biggest lessons that you’ve learned that you wished you’d known in the beginning?

I don’t know. It’s hard. I don’t want to be the person who says “Work hard and it’ll pay off,” because that’s kind of bullshit. And I do have a lot of privilege, and i try to be cognizant of that. I’m white. I come from a well-educated background. I’m suffering from a lot of student loans because of it now, but I was able to go to college and learn a lot of things about the world, which has made it much easier for me to succeed now. And so I think I want to recognize those things because it’s not just a situation of “Do good work. Work hard and it’ll pay off.” It’s not that.

Absolutely, the privileges and the things that— the situations that we come from affect our ability to succeed. You just have to hustle. Life is a fucking hustle. And, obviously, there’s mental health stuff and physical ability is— stuff and not everyone can do what I was doing in terms of working 14, 16-hour days to literally just push through. I don’t know.

Listen to yourself. Figure it out what it is that you want. Set some goals. Start working towards them. Evaluate, move forward.

Find a mentorship. I wouldn’t have been able to do what I’ve done without mentors across different parts of that journey. Whether it was Beth really on pushing me to even sit down and write my first line of code, or my friend Matt much later on when I had the internship, starting to talk about career development and where I wanted to go and how to maneuver to get promoted to full-time and to start a career track. Find people. There are career people, there are women that have been doing this, and they can help. Maybe not tell you what to do, but provide a sounding board, give wisdom from their own experience. I found that kind of stuff is really helpful because I could ask questions like, “Am I going crazy or is this something that is actually happening? Is this something that I need to be concerned about with the way that this manager is acting?” Because it can be really easy to get caught in your own struggle and your own moment, so being able to get a little perspective and jump outside of that is really helpful sometimes.

I pay for a therapist every week and it’s the best decision I ever made [laughter].

So while I wasn’t born there, I grew up in Georgia, metro Atlanta area.

We moved around a few different places in Georgia. Most of the time we lived in a town called Peachtree City, which is one of those suburban towns where there’s not a whole lot to do but there were golf cart paths throughout the entire city. So your family owned a golf cart, you drove it around and that was totally normal [laughs].

Growing up, my family never had a lot of money. No free or reduced lunch at schools and that type of thing. Some of those basic, everyday things people think of we couldn’t afford. At the same time, my mom worked for an airline, so we did grow up being able to travel a lot. It was interesting because, say my friends want me to go bowling, but I couldn’t pay the $5. But then they’re like, “Wait, how did you go to Switzerland?” [laughs]

Peachtree City was—I didn’t know if upper-middle class is the right term—but it was a relatively wealthy town because a lot of people who worked at the airport lived there. So we weren’t in the best part of town, but it wasn’t a dangerous area—it was just a little bit lower income. We had good schools which was really important.

Neither my mom’s family nor my dad’s family were from Georgia. It was just a place they picked on the map when we were moving there, but it was important to them that if we were going to stay there, that it be a good place like that to raise children. So most of my formative years – I think it was from fifth grade through high school – I was there.

I was never the popular kid. I did band in middle school. I was kind of the the nerdy kid. I didn’t recognize that I had gender issues at the time, although in retrospect it’s like—oh, that makes sense why I didn’t care so much about my appearance because I didn’t want to look like that in the first place [laughs].

I was also raised in a conservative religion which I just thought was normal—I thought that this is how life works, these are the parameters of life, here’s how you live, here are your values. I just kind of went along with that until high school when my parents started having marital problems. My dad ended up moving out of the house my senior year of high school, and their divorce was finalized I think two or three weeks before my high school graduation. That was one of the first big awakening moments of my life because I was like—this marriage that I thought was going to be forever—some axiom of reality almost—fell apart. It made me wonder, “What else in life have I just been taking for granted like this? And what else do I need to question?”

The answer in my head was, “Everything.” I needed to understand, “What do I actually believe?” Not just, “What was I told?”

What was your path out of Peachtree City?

In parallel with that, when there’s family issues going on, you don’t really think about things like hope – where do I want to go to college, what do I want to study – because you’re dealing with things at home. And so I ended up going to the college that my family wanted me to go to, which was a religious school, and it was not where I should have gone [laughter]. I realized that very quickly once I got there.

After a few years there, I realized I do have a choice about my life– maybe circumstances out of my control brought me here, but I can choose whether to stay here or not. I realized I had a choice and was like, “Okay, let’s go for it.”

Awesome.

Yeah. So, at that point I sent off a transfer application to University of Georgia without having ever visited there. Luckily I got in, and so while at the University of Georgia, my process of self-discovery continued.

But now, I was in an environment where I was like, “Okay, now I need to have this typical college experience.” By that, I don’t mean the partying. I never got into the partying scene, or anything like that, but just meet people, have new experiences, learn things, get different points of view. At that point I was done with church, but now was the process of figuring out, “What do I believe now?”

So, once that set of discovery was underway, then the gender issue was like, “MY TURN.” [chuckles]

Again, before that, I didn’t really realize it was there, even though in retrospect it’s like—yeah, it was there. [chuckles] So, that’s when I first started really exploring like, “Okay, what are these feelings? What does this mean? What should I do about it?”

I was very fearful, because even though I was in a college town, it was still the Deep South. I explored a little bit in my head, I tried a little bit out in public. I got involved at the LGBT organization at the school. I made some mental progress and dabbled a little bit, and got a better understanding of the world. But before I knew it, two and a half years passed and I was graduating.

Then reality is like, “Oh guess what? The professional world is not like school.”

Were you into tech at all at this point?

I knew my parents couldn’t afford to help me pay for college, so in my first semester I immediately looked for jobs. I got involved with Unix Users Group, and ended up getting a job referral through them after that first semester. I was like, “Okay. Even if they don’t necessarily know that I want to work in computers, it pays a lot better than other student jobs.” I definitely had some skills from that, plus just playing with computers growing up. I wasn’t quite the younger end of the millennial generation, where they grew up with all that, but there was AOL, and those kinds of things. I definitely had some of those basic skills.

So you graduated and started your move toward adult professional life. What happened next?

At that point I moved back in with my mom, because I didn’t know what exactly I wanted to do even then. I just needed to focus on finding a  job and it was really hard. I thought that because I had a degree then of course I’m going to be able to find a job. It won’t be perfect, but I’ll find something. That doesn’t work quite that easily, especially if you have a degree that was prepping you for grad school—not the job world.

While still living with my mom, she decided that she wanted to move to Phoenix to be closer to family, because her sister lives out there. So, I was like “Okay, well, I still don’t have a job, so I guess I’m along for this ride too.” So, I move to Phoenix and am still looking for a job and ended up in a call center on the phones. Not the funnest job in the world, but it was like, okay, at least I got a start. I have my own income.

So you got your start in a call center.

Yep, and even though the job wasn’t what I enjoyed, it got me started on a clearer path. My job was being on the phone. That said, I still had some of these computer skills from college. While I was on the phones in the call center, I was like, “This process could work a little bit better. This report would be so much more useful, if it gave this extra information.”

I would ask them, “How did you produce this? Could we make this better?” I would just do little things like that. Then after a while, they took notes of, “Hey, Michael (my former name) is doing these cool things, and we have this idea for a project we’d like to do,” so they pulled me off of the phones, and assigned me to a technical project.

Throughout the day, maybe two or three times a day, they would pass out little sheets that showed stats, because it was a very competitive, numbers-driven environment. They wanted a way to display those numbers much more frequently on the computer. And they knew I had some web development experience from college, and so they put me on the project and said, “Once this is done, you go back on the phones,” which wasn’t what I wanted to hear. Luckily, that project did not end up sending me back to the phones, because it worked out well enough.

Awesome.

So then I ended up working on their operations team, which slowly morphed over time as the team grew, and I started doing some other application development for them. Eventually at a team’s request I was able to transfer up to the office in San Francisco to provide more technical support.

So that’s how you ended up in Silicon Valley.

Yeah. And so that was great for a while. Then the manager who had brought me up here ended up leaving the company. It wasn’t bad. They just didn’t really know what to do with me at that point.

One of my teammates at the time ended up interviewing at Facebook. The position was a little too technical for him, so he gave them my name. They called me and I was like, “Well, I wasn’t even looking but Facebook’s calling me. I may as well at least talk to them.”

Yes [laughter]. Yes you should.

So I talked to them and ended up interviewing with them. It was going great. At the interviews it was really smooth, and I was like, “Okay, these went great. When do I start [chuckles]?”

They told me no. I was like, “No!” But the “no” was delivered really well. At a lot of places you get told no and you’re like, “Well, why? What was wrong with me?” But at Facebook they told me, “Okay, we thought you were a great cultural fit. You were a little bit weak on the coding interview. If our needs were different, then maybe that’s the kind of thing that we could bring you on and train you in, but we need more experienced people right now.”

So Facebook told you no and yet here I am talking to you from your office at Facebook?

They told me to keep in touch. I thought they were just saying that to be polite. Then, about a month after that, I got an E-mail from the recruiter just checking in to see how my job hunt was going. I was like, “Wait, are you serious about wanting to keep in touch?”

Then, a few months after that, I get another email saying, “Hey, can we set up a call?”

I get on the line with them, and they’re like, “Well, remember how we said if our needs were different? Well, our needs are different now. Are you still interested?” I was like, “Yeah!” They said, “Okay, well we talked with the team that had interviewed you before to see if they were still interested in you, and they gave a resounding yes, so we would like to extend you an offer without even re-interviewing.”

Wow. That’s amazing.

I was so glad I took that call in a private room, because I did a happy dance, and it would have been really embarrassing to be seen in public doing that. [laughter]

That’s kind of what kind of got that ball in motion. When I gave my notice, and I told them where I was going and they didn’t even attempt to counter. They kind of knew, “Yeah, this is a lot better opportunity than anything we can provide.” So then I was like, “okay, it’s time to go to Facebook.”

And at the time the gender stuff wasn’t even on my mind. The reason I thought when I moved from Phoenix to San Francisco, I was like, “Well, maybe it’ll be a better environment, it’s much more LGBT friendly there.” I was still terrified and even though the SF office was better than Phoenix culturally, it was still a big corporation and so I still didn’t feel like I could do anything about my gender issues. And so coming to Facebook, that wasn’t even an option on my mind.

But then I started seeing the information they were sending out about orientation, and one of the things in there said the dress code was that we want you to be your authentic self, so wear whatever you want. It was like, “Okay, this sounds good, but do they really mean it?” And so I showed up to work on my first day with my nails painted.

I figured that’s transgressive enough that I could kind of test the waters, and see if they really meant it, but not so much that if it was a major problem I would get sent home, or fired or something like that. And nobody said anything for like, two weeks, and then somebody said something nice about it. So it’s like, okay, this is different.

And then throughout orientation, and me even continuing throughout Facebook, you hear a lot about how we want people to be their authentic self and bring your full self to work because by doing that and not creating separate work and personal personas, you get to know your co-workers better. You have more relationships with them and get along with them and you understand and relate to them better. And so I was like, “Okay, cool.” But having grown up and you know, mostly red states, I had a lot of like baggage about what’s acceptable in society and here’s what you can do, here’s what you can’t do.

Yup.

It’s like out here I’m suddenly getting a different message—not only it’s okay to be yourself but we want you to be yourself. This one thing that we talk about here is that at Facebook we don’t want to just serve a certain class of people. We want to serve the whole world. And to be able to serve everybody, we need to be able to represent everybody. And that’s really why diversity is so important to Facebook because if you don’t have representatives from all sorts of populations, then how do you really know what they need and how to serve them?

Absolutely.

And so even for the first couple of months, I didn’t know if I believed it. And it’s not because of how they were delivering the message. It was because these beliefs that I had about myself and what’s possible were so limited from the past.

And so the longer I was here, I was like, “You know, maybe this is possible. Maybe this is what they mean. They really seriously mean this.”

So I started here in July of 2014, and by September was the first time I ever talked to a gender therapist because I realize that it was important to me not to ever die with regrets or have something that’s just… you didn’t do that you wanted to do. Nobody wants that life. You want to have a fulfilled life.

It’s not really now or never, but kind of like now is the best time to do it. So if I’m going to do it, I really should do it now.

So you decided to start your transition while at Facebook.

Yep. I talked to the gender therapist in September, and started on hormones in October.

It sounds like a quick turn around, but it was a lot of time of letting go of those beliefs that were limiting me. Earlier in my life those limits were coming from outside environments, whether it was church, whether it was society, whether it was school. Once those external limits were gone, then the new question was whether I can get past my own self-imposed limits.

Since then it’s been really amazing to see how it’s gone. Because being here really is what finally put me in place where it felt like I could do this.

In the past there were worries, doubts. Will my family reject me? Will I get fired from my job? Even at my last job where I was in San Francisco where transformation would be easier, I still had that fear.  Being at Facebook is the very first place in my life, that I ever felt like, this is something safe to explore and to do.

It was definitely not a punctuated process for me. It was something I started doing over time. Makeup over time, toward the end I sort of started dabbling with outfits a little bit. Throughout this whole time when I’m discovering who I am, and how I want to express myself, everybody was cool about it, because there’s so many different kinds of people both in San Francisco and at Facebook, that everybody understands and accepts this is who you are.

I just kept doing it because it’s like, “Oh, people are being nice to me and it’s okay.” Once, I came to work in a skirt and I still got invited to play ping pong. I was like, “Okay, cool!” [chuckles]

I just kept slowly making progress and progress as I became more comfortable and overcame any fears through so many supportive people. One of the biggest things I’ve learned through this journey is that it’s not something you can do on your own. You really have to look to those who have gone ahead of you, rely on those who support you.

Here at Facebook we do have a very strong LGBT employee resource group. And so there’s a lot of support there and there were other trans employees who I could go to and get their personal stories. Before it’s like okay you read these things on the internet about these strangers or these medical references, but I can’t personalize that. But here I was able to meet other people who have gone through these things and I can say, “Okay, here’s the way my story is similar to yours, here’s how it’s different.” And being able to see that and see how it actually plays out in life, and just bounce my ideas and thoughts off of these people really helped me move forward because otherwise it was so theoretical to me.

At some point in the process I went to a ladies wine night at a friend’s house and introduced myself to everybody as Addy. After that I was like, “I want to Facebook friend all of these people.” And I was like, “Oh, crap, but my name’s not Addy on Facebook.” So I was really torn because my Facebook account is kind of like my social hub – like all of my different social groups from my entire life are on Facebook. People from church. People from multiple colleges. People from various jobs.

I realized is that if it got to the point that not coming out was interfering with me being able to live the life that I wanted to live then that was the time to do something about it. So I was like, “Okay, well, here we go.” And I updated my name on Facebook.

I get in the next day and I’m like, “Okay how’s everybody going to react, how’s this going to go?” The only question people had for me is, “okay what would you like us to call you now?”

My boss automatically switched pronouns, if he messed them up he corrected himself, so it was just super smooth. That was what surprised me going through all these things—I was so afraid of how are people going to react. Who’s going to reject me, who’s not, and the response was remarkably positive. Some people from past jobs were a little awkward about it and some members of my family, like my Mom, really struggled with it. But in my family’s case they realized that even if they don’t understand it, or maybe don’t think it’s real so-to-speak, they did recognize that I was a lot happier. I’m like, “Okay, we’re going to ask some questions about these things but I was markedly happier.” So they’ve been supportive, so I just kind of going from there. I was like, “Okay, this is cool. Everybody’s supportive.” Since then it’s been great to see other people go through this process because one of the things that I mentioned that I learned was that you can’t do this alone. I fully recognize that I got help from so many people. It was important for me to be able to pass that on to others because I couldn’t do it on my own. I kind of owe that to other people to do it too.

I’m not politically active. Most of my help is kind of more personal. As new people join Facebook or realize that they’re struggling with gender issues, a lot of them get referred to me. Then I can kind of walk them through, “Okay, here are the great benefits we have. Here’s our local trans group at Facebook. Here’s what my experience has been so far.” So I think there are four people that I am mentoring right now.

That’s so great.

They identify at different parts of the spectrum, and they are at different points to the process. But look, this is important to me, so it’s really become a great little community. And it’s really fun to watch them as they go through some of the same steps that I did, because it gives them so much more perspective. Because when you’re the one going through it, like, “Oh my gosh, can I handle this?” And you see them going through and it’s like, “Oh. Is that what it looks like from the outside?” [laughter] And so it helps me both help them through it as well as understand my own journey, and put into perspective what I’ve done, which helps as I consider the next steps, because I don’t know exactly where this is going to go from here.

I’m kind of taking it one step at a time. I’m like, “Okay, I’m happy with what I’ve done so far. I don’t regret any of this.” I don’t necessarily know answers to questions like, “Do I want surgery?” I don’t know. And I realize it doesn’t matter. At this point, I can think, “What is the next step, and is that something I want?” And then it’s go, and then we’re moving forward. One day the answer to that question will be no, and then I’m done. [laughter]

This is where I’m at just now—I started hormones in October of 2014 so it’s not been quite a year and a half. And it really is kind of a second puberty. It will continue for a long time, both physically and mentally.

Yeah.

It really is a unique experience, because not very many people get to see from both sides of the gender equation.

I would love to hear more about this.

It definitely gives me a little bit more perspective on things. In some ways, it highlights for me the way the genders are treated differently. And it kind of upsets the feminist piece of me. I understand I’ll lose male privilege, but it’s not that I’m going to lose these rights. It’s like, well, everyone should have these rights. So, it makes it important for me to support those causes as well.

But I’m also learning the way that the two genders are similar. Everybody’s human and psychologically men and women are more similar than different. When you’re only on one side, you, to a certain extent, you romanticize or think of the other side as foreign, and it’s not. We’re all human.

So it’s been really interesting from both of those perspectives just to see how many interactions with others are different, how they’re not. And that’s kind of where I’m at. Today is just kind of continuing to learn and grow.

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

I don’t know. Throughout my life and all these different places I’ve lived, I’ve thought, “You know, this is a great place and I get to have these experiences, but not forever.”

Do you think you’d go back to the South?

Oh gosh no!

Yeah, me neither. [laughter]

Not for the reasons you would think. Like if people ask me, “Oh, should I move to Atlanta?” then I wouldn’t have any problem recommending it to them. I feel like Georgia is the past, for me.

It’s definitely important to me to keep moving forward in life. While I love my friends that I have there, it’s important to me that I keep moving forward and having new experiences and not just going back into the past. I want to keep moving forward and developing.

So I don’t think that that’s the right place for me, even though for other people– I mean it is a great city. It’s the economic capital of the South. But I don’t think it’s my future. San Francisco’s been the first place I ever thought, “You know, maybe?”

A long time ago I gave up trying to predict what the future will bring, because every year when I look back I could never have predicted where I am.

I do think that, for now, this is a great place for me to be. Facebook has so many opportunities both for personal growth and professional growth that I really have no reason I want to leave right now.

It’s actually kind of funny, the experience here almost feels like a time vortex. I’ve been here a little over a year and a half and I’ve done so much more here in that time than in multiple years at previous jobs. So I would like to keep that accelerated rate of growth and development as long as I could possibly manage it. And so I hope to be here for a long time.

There’s been so much conversation lately about how diverse teams perform better—how different perspectives are being brought to the table to inform a better product, especially for a company as global as Facebook. How do you feel like your background and life experience impact the way that you approach your work?

I think what I’d say to that one is that having grown up with scarce resources—when I was in the call center and we were building out that reporting and technical infrastructure, since it was all new to them, they weren’t necessarily committing funds to us, so there was this idea that resources are scarce, but you still want to keep doing more, growing more. It required me to develop creativity.

I was like, “Okay, well, how can I do this better? How can I make this faster? How can I make this handle more without being able to get additional resources?” That was my biggest thing that I got out of that last job—sometimes you just have to find creative solutions. You can’t always have tons of money or tons of resources to devote to a problem. And so you have to be like, okay, well, just because I don’t have the resources to do what you’re asking doesn’t mean we shouldn’t still try, doesn’t mean it isn’t still what we need to do.

And in my personal life, I don’t want to be held back by, well, I only have this much experience, or I only have this car, or that asset, or whatever. It’s like, I don’t want that. That’ll hold me back from continuing to learn and develop, and so I have to be creative and find a way to do more with less. And then when I get more resources, then great, I can use these more efficiently, and do even more. And so I think that’s really how my background has helped me here, is just that I can get pretty scrappy and figure some things out that other people wouldn’t have thought of because they didn’t have to struggle to be able to do that.

I love that. My last question—What advice would you give, based on lessons that you’ve learned, to folks from similar backgrounds hoping to get into tech?

I think the biggest one would be not to hold yourself back, because so many times we think that because of our circumstances that that’s all that we’ll ever have. It kind of sounds cliche to say “American dream,” but it kind of really is. That you believe in yourself, you know what is important to you what you’re passionate about, what you want out of life, not what you believe is possible based on past experiences. That’s what really helps me move forward because life’s been a surprise for me so many times.

A lot more is possible than you believe if you take advantage of opportunities. Sometimes they come by, and if you don’t take them, then they’re gone. So just keep your eye out for those, and when they come along don’t wait and say, ‘Maybe one day.’ Because there isn’t always a one day. Life is only so long, and everything in life changes. That is kind of what life is: it’s change. So take advantage of the opportunities when you have them. Learn all that you can. And just keep trying and learning.

My early years, I grew up in New Jersey, in the farm country of New Jersey. George Washington marched down Main Street in the town that I grew up in, so it’s incredibly insulated, affluent area—very straight, very normative. I lived there until I went to college.

What was your childhood like? Were you feeling totally isolated in childhood or were you feeling pretty normal?

I had a sibling and we’re close in age. We’re a year apart – a year and four months. That alleviated some of the feeling of isolation, but it took 30 minutes to get to the supermarket by car so it was hard not to feel isolated. My parents divorced and it took them about eight years. They were locked in our custody battle and it was really acrimonious. That started when I was in second or third grade and went on for a while, so that was tough too. Yeah.

How did you first discover tech? What was the early entry point into the world you are in now?

My entry point to technology came really late. We had a computer in our house, a Compaq, but it was in my dad’s office. My brother and I would only get to play video games on it once a week. We played that video game Myst. It was really hard. I didn’t have a cellphone until the middle or end of high school. My first regular access to a computer was in computer typing class. I remember those.

Oh yeah. I was so good at typing class.

Yeah [chuckles]. The typing programs. It wasn’t really a huge part of my life. We didn’t even really have cable growing up. I think it may have come later than other kids. Really, these memories may be similar to other millennials like dial-up internet, first AIM screen name, going into chat rooms. My brother and I, we’d go into chat rooms and type in ASL [age/sex/location], try to flirt with people, and that was always fun.  That was the beginning, I think, like teens. But even still, there was only one computer in the house and limited access.

It sounds very similar to my upbringing. What was your first AIM screen name?

Oh my God, dogluvr [chuckles]. But, it was–

No numbers?

…L-U-V-R [chuckles].

Wow. That’s good. I was maybe too late to the game to grab sunnygirl sans numbers, so I had to do sunnygirl87 which is ironic because I don’t even like sunlight.

[laughs]

Then I became puddinpie, because I loved pudding and I loved pie. Puddinpie26.

Oh my God [laughs].

Yeah. So many good ones.

Yeah, I love how they’re so naive, like so earnest, all of them. They’re great.

Did you have early inclinations about what you wanted to do, or be, when you grow up, and did you have any family pressure in any particular direction?

Yeah. My parents are very– they’re lawyers. They, like I said, they divorced, and they both remarried lawyers. They’re very much people that have always been on a track and expect everyone else to be on a track. I think they expected that I’d be a lawyer. I wanted to be a writer or a poet, definitely had more artistic inclinations.

So walk me through the winding path of you getting into tech.

Oh my God, I’ve started interviewing people at SoundCloud and I get asked that a lot and you would think that would help me crystalize my own answer by now but I’m still finding my way through it. I graduated college in 2010, that was deep in the recession and I was living in New York at the time, the first job I was able to get was working at a Borders before they went out of business. I was one of the people at the front with a Walkie Talkie that was busting shoplifters, that was my first job.

Amazing.

And then Borders folded and I just kind of took any job I could get – I went job to job and eventually decided to move out to the Bay area like typical Bay area story, no job, no place to live. All of my friends were giving me the advice to apply for things in tech because it was casting a line into to a larger pond.

The first job in tech I got was at this company called Code for America. It’s like a non-profit tech company [chuckles]. Sounds like an oxymoron, it is an oxymoron. I was there for a year and a half.

I’m a huge music nerd and decided I want to work in music tech, and that’s how I got into SoundCloud. It’s pretty lucky, when I look back on it now. I didn’t have any connections and being in tech has made me realize how nepotistic it is, and it’s all about who you know. I applied completely blind with just a cover letter and resume, and ended up getting the job. I work on their Community team, which is tech jargon for customer service. [chuckles]

I’ve been doing that for the last two years. That was a really quick synopsis, but there have been other detours– I thought I wanted to work in book publishing when I graduated from school and  I worked at Random House in New York City and I was doing book publishing for a while and then I think moving out here and being unemployed, it felt like tech was my only option, which is how it is, but I don’t know. It’s almost like I made the choice, but the choice also happened to me.

I probably use SoundCloud more than any other app total I think.

Wow.

I know. Well, I have music tastes that tend to surprise people—so when people want to know what kind of music I listen to, I’m like… the only way I even know how to begin explaining this is just to point you to SoundCloud and go look at my likes.

Anyway. What are some of the most exciting things to you about either your job specifically or working in this kind of industry?

I work in a niche inside technology, like music tech is a niche within the broader tech industry. I am excited by the fact that I’m actually passionate about the area of technology that I work in. I could be working in consumer tech or something where I feel absolutely nothing about what I’m doing. I feel good about that.

What would have been some of your biggest struggles during your time in tech?

Oh, man. The feeling of loneliness. SoundCloud is based in Berlin and I work in the San Francisco office and that’s an office of 20 people. I was one of the first out LGBT people at the office so there was a loneliness in that. Then it took me a year to come out to everyone as being gender queer, which is on the trans spectrum, and asking everyone to call me by gender neutral pronouns. That was a further segmentation of loneliness. That’s been hard. There have been moments of friction and– misunderstanding and just ignorance along the way, for sure.

I’m curious to know, where you have found your support networks during these times? I know that you formed one on your own.

That’s a really good question. Yeah, I ended up forming a diversity resource group with two other LGBT employees at SoundCloud at the time, which is crazy in a company of 250 people. But there were only three of us, and that was a support network. I have a really rich queer community outside of work, a really amazing, supportive girlfriend. All those things definitely strengthen me.

What is it like in your experience being deeply involved in two different communities of two very different levels of privilege? You’ve got tech and you’ve got the queer community—what’s it like to straddle both?

Yeah. Even outside of non queer spaces, these days I’m just incredibly reticent to say that I work in tech. I think in queer spaces and at queer parties, I feel that friction a lot too. I feel like– there are queer people who work in tech, obviously, but I think most of the queer folks in the community want to think of themselves as activists and disruptors and—oh, cute cat.

That’s Raphael.

Or artists. Not to say that you can’t be all those things, like an activist and a disruptor and a artist and work in tech, but I think there’s a perception in the queer community that you can’t and it feels a little like it’s– like you can’t hold both spaces. I have a dialogue with myself about this almost daily but I tell myself, “you are disrupting things just by virtue of stepping out, educating people on trans identity, and advocating for yourself and just getting in people’s faces and bringing things to light that would have never surfaced before.” I do feel like I’m disrupting and I do feel like I’m agitating things and I think that is a form of activism. But, in the two-minute elevator spiel of someone else who’s in the bar, I just sound like a yuppie, so it’s incredibly nuanced and a really frustrating thing to for sure.

What do you think are your biggest motivators?

At work or just life, both?

In life, what drives you?

Coffee. I have like a severe caffeine problem. [laughter]

I take a lot of pride in being a good child, and sibling, and partner, and friend. That’s something that drives me. I know that sounds a little corny but that’s a huge source of pride for me. Also just the fight to be seen, that too.

Yeah.

That moment when it finally clicks for someone. That’s happened a few times at work now, where after a lot of correction and a lot of nudging, they finally adapt, really ‘see’ you, and evolve in your direction. People start calling me “they” and they make me feel like they finally see me. That’s a motivator. That makes it all worth it.

How has coming out affected your perspectives on equality in the workplace?

I mean, I don’t know, I feel like there’s nothing I can say that hasn’t been said. Like, my workplace, Soundcloud, and other tech companies are incredibly white and male-dominated. All the leaders, for the most part, are white and male, and yeah, there are all kinds of ceilings that are yet to be shattered or even acknowledged before they can be shattered. Yeah, it’s hard working in a place where you feel the oppressiveness of all these different kinds of ceilings that exist for you, but you can’t really talk about it or acknowledge them, and that’s what it feels like. And I see those ceilings, and they’re not always just my own, but for people who are completely female identified, those ceilings exist and, yeah, there are just different kinds of ceilings and hurdles and it’s just funny because there’s also a ton of talk about diversity and inclusion right now. I feel like in the last year the discussion about diversity and inclusion in tech has just completely taken off, and for all this talk and conjecture, you would expect some more acknowledgement of the ceilings and hurdles that I’m talking about, but there’s a ton of talk and conjecture and it doesn’t feel like there’s a lot of change or momentum yet. So in terms of equality in the workplace, my perception is that there’s a lot of talk, but there’s yet to be much change. I mean, maybe the needle is just moving so slowly that it seems imperceptible, but I feel very impatient and weary a lot of the time with the theme of equality in the workplace.

Have you had any particular mentors or people that you’ve looked up to for inspiration, or even just people that have been pivotal in your career?

I have this theory about mentors. It’s like—you know when you’re dating someone and you really like them and you just want to define the relationship and ask them to be your girlfriend, boyfriend, whatever. I feel like my past experience with mentors is I’ve done that and then scared them away, so lately I’ve had mentors and I just don’t tell them they’re my mentors. I have people that I look up to and look toward for inspiration. But they’re not formal mentors because I think defining the relationship kind of ruins it a little bit. And yeah, there are just some badass women that work at SoundCloud – a lot of them have left – there’s a huge attrition problem. There’s a woman in our office who’s– it’s an open office floor plan and she’s taking calls and yelling at guys on the phone and making deals. She’s just taking up a lot of space in a way that I haven’t seen a woman do in a workplace– I’ve only ever seen men do that. She takes up space in every part of the office she’s in and it’s awesome. I’ve just never seen anything like it. There are just a lot of really assertive women that work at the company and that’s been cool to see.

What is important in a job to you now versus when you started? Like what do you feel is really priority to you, either currently or in the future?

I don’t want to settle for a job where I’m not a culture fit because I’ve done that too many times before. I don’t expect to stay at SoundCloud forever but I am a culture fit, for the most part, in the office right now. Like I come in and I feel accepted and I have friends and this is the first job where I’ve ever had that and I don’t want to settle for not feeling like a culture fit anymore because culture really makes or breaks a job. It sounds so obvious but it took me like four years to realize that.

How do your friends and family feel about the path that you’ve taken and the work that you’ve done? You’re not a lawyer.

I think they’re proud of me. My parents are not super adept with technology. Neither of them know or use SoundCloud or know what it is so they don’t exactly understand what I do day-to-day but they appreciate the fact that I’m in an industry that’s well regarded and I’m making my way so they seem okay.

That’s good. How do you think the culmination of your background and life experiences affect the way that you approach your work?

As I mentioned, I work on the Community team so that means just writing with users but I ended up moving into a specialization track and I’m writing with users that are in crisis and I have to moderate content that they report like if they are being abused or harassed on the site or if they see hate speech or unlawful content, sexually explicit content, basically all the ways that SoundCloud can be misused, I write at those users and I moderate that content. I definitely don’t think it’s a coincidence because I think my background allows me to be really compassionate and empathetic and I think having experienced discrimination and having had things happen to me that are abusive in the world I think it gives me a unique ability to moderate things—I don’t know, I think it all ties together in some strange way.

I’m curious to know what you feel like tech could do a better job of culturally.

Culturally? Like, broadly, it’s ideas of inclusivity. I mean I’ve interviewed at places in the past where you have to walk up a flight of stairs and there aren’t even accessible elevators and I just feel like there are all kinds of diversity that are thought of last or not at all. And there are the kinds of diversity that you can’t see. You know there’s mental illness and other kinds of illness that aren’t visible. So yeah, just broadening. I think diversity inclusion needs to be broadened and I think learning and development also needs to be brought in. There needs to be more rigorous sensitivity training done internally.

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

So I’m part of a support group for folks that are on the gender spectrum and we’ve all talked about making a zine and leaving it in lobbies of tech companies and just places around the city. So I really want to make that zine about gender and gender fluidity. That’s a huge goal. Yeah, also we’re working on bringing an external facilitator to this and having them do a training on trans-identity. A lot of people in the office, abroad especially, don’t understand what transgender means. Those are goals. I also played tennis for a lot of my youth and I really want to pick up tennis again.

Where do you see yourself in like 5 or 10 years? Do you think you’ll still be in tech?

I want to work on diversity and inclusion in tech, full time. I don’t think I’m going to be able to do that at SoundCloud, sadly, so I’m starting to look around and ask myself, where can I do this and how can I do this? Who will give me that shot? And eventually in ten years I hope that I will have gone to a company, learned the ropes, and then go out and become an independent consultant or started my own consultancy or something.

I love that.

So I think in ten years I’ll be working alongside or with tech. But, I don’t know if I’ll be in it anymore, strictly speaking.

I had a question but I lost it. Hold on. After a few hours of interviews, sometimes things start getting a little Swiss cheesy.

I’m sure.

Let’s see, my last question would be about like lessons you’ve learned and any advice that you’d have for folks who are just starting out in the industry or come from similar backgrounds to you or going through similar struggles?

I am still telling myself this now, but I think if someone who grew up and was socialized as a woman, I still fall into this trap of thinking I’m not good enough—basically imposter syndrome. I always applied for jobs that are exactly at the level that I’m at or slightly below. I’ve never applied for something that’s above my qualification level. I would advise someone who’s a woman or non-binary person to aim high, because I’m still learning how to do that and I’ve been out of school for almost six years and I’m still looking at things and applying to things that are just at my level. And, I think if you aim high, you’ll get farther faster.