Okay. Let’s start from the top. Tell me a bit about your early years and where you come from.

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.”