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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Expand on that.

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

What did you work on while at Google?

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

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

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

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

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

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

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

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

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

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

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

Yes absolutely.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Can you expand on what’s been lost?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Early years. So I was born in the Dominican Republic. Me, my mom, and my sister—well my mom and my dad were never married at any point, so technically I’m a bastard child if that’s how you would like to call it.

It’s the same in Norway. Most of my family isn’t married in Norway and that’s normal. They all just make babies together.

[chuckles] Then my mom took me and my sister to New York at a very early age, at like five years. This is hard because I hardly ever talk about my mom because we’ve had a very rough history.

My mom was a single mother. She came to a new country, didn’t know the language at all, took on some small jobs here and there as a housekeeper—when I was very young—in New York. I was like five or six. I don’t even remember any of this really. It’s all stories that I’ve been told.

“It was a hard time for me when I was really young. We were poor and we all slept in one bed in New York City.”

During that time, she also got into the system. She applied for and received welfare, and then once I got a little older, I started seeing how my mom started to change. This is a touchy subject because I don’t really talk too much about this because it is kind of a dark period of mine—but my mom kind of got really unmotivated, stopped working, starting taking out a lot of student loans and doing college classes, even though it seemed like she wasn’t really into the profession and was just using it as a means of getting free money and really not spending too much time at home.

It was a hard time for me when I was really young. We were poor and we all slept in one bed in New York City. It was in the Upper East Side, and at that time that area wasn’t the Upper East Side that it is today I guess. It was higher up in the hundreds, so it was almost borderline East Harlem. So I was your typical poor kid in public school system growing up in New York

My dad, who I’ve been in contact with here and there, was actually—he’s a very smart businessman. His business started expanding and getting very big. At one point he came back to me right before I started junior high school, and saw how I was developing and wasn’t very happy. I would say I was a little bit of a rebel. I was staying out all the time. I was kind of like the independent, young New Yorker that most New York kids are really [chuckles]. Super independent, living our own lifestyles, doing whatever we wanted. He wasn’t very happy so he asked me if I wanted to come back with him.

At that time that was a really hard decision. I didn’t want to leave my mom. I knew that she was having trouble and I wanted to help her out, but I couldn’t really. It’s just hard for a young New York kid. I was maybe 14 or 15, I don’t remember exactly how old I was at the time when I moved to the Dominican Republic with my dad and went to junior high school and high school there. It’s funny because I look back at it and it’s probably the best decision I ever made. My dad was doing very well. I was able to live a different lifestyle that I’ve never lived before. It was much better than what I had in New York, surprisingly. It was also like the Dominican Republic In general, is a very family oriented country. A lot of the families stay together and they’re very close, so I got to meet my family, and be very close to them at all times. People that I’m so happy that I’ve gotten much closer with by moving back home. Since it was just me, my mom, and my sister.

So I’m going to take a step back, cause there’s actually a lot of stuff that I left out. [laughter]

Let’s go back. Let’s dig in.

Let’s go back a little. [chuckles] This is going to be a little weird. So when I was in New York, my mom (for a short while) worked for a couple of people that I hold very dearly to my life, and have helped me get to where I am right now. This couple hired my mom to be a housekeeper for them, and then they met me and my sister and took us under their wing. Almost as their own, but we never actually lived with them. But they were mentors to my sister and I when we were very young. The reason I never steered too far to the point of no return, was because of them. They were able to help guide and provide for us, which was something that we didn’t have when we were young so we’ve always held them as really close family members.

When my dad came to ask me to move back to the Dominican Republic is was a hard decision. It was one of those decisions where you’re like, “I’m going to leave this new family I have here, this small family that I just started making my own.” Then there was my mom who was having a lot of problems, so it was a really hard decision. I just took it and just went with it, but then again, I look back and I have no regrets.

In the Dominican Republic, it’s totally different. The lifestyle there is much more laid back. It’s not as hectic, and there isn’t so much childhood pressure that you would get in New York City. There were things that interested me that I could actually focus on.

I was a very creative person from a very young age and I was able to take the time and develop certain skills that I probably couldn’t have developed if I stayed in New York. Really, it was funny that a country like the Dominican Republic, where design isn’t as important, would help nurture me. I don’t know if important is the right word, but it is something that’s not always the forefront of a small country. I think countries like the Dominican Republic and smaller countries are very focused on creating businesses and things like that, and design is not really part of that equation —at least not yet.  

“Really, a lot the stuff that I learned was on my own. I just sat there. I played around with things. I spent a lot of days sitting in my room designing a little bit, (or at least what I thought was designing). I don’t know. If I look back on it, it’s probably crap now [chuckles], but it’s still good stuff.”

At that time, I saw an opportunity to help out with small marketing projects. I made some promotional flyers for nightclubs and stuff like that because they were like marketers basically and marketers needed creativity. Without creativity they can’t do their marketing. That’s where I got my start. I was 15, 16 years old and finally getting my hands on a computer with Photoshop and learning things like CorelDRAW, Photoshop Illustrator, Swift, Flash and all kinds of programs. Once I got my hands on those tools I started to expand from paper and just started playing around with new things.

In between that, the distractions were really around and I thought to myself should I be doing this? I think my dad did the right thing by never really talking to me about what direction I should go in because if that were the case, I probably wouldn’t have stuck with design. I think it was just a part of everyone’s mind that design just doesn’t equal success or an opportunity to be successful, but I was able to continue with that. Really, a lot the stuff that I learned was on my own. I just sat there. I played around with things. I spent a lot of days sitting in my room designing a little bit, (or at least what I thought was designing). I don’t know. If I look back on it, it’s probably crap now [chuckles], but it’s still good stuff.

Honestly, I think what really boosted me was in part what my dad did for me. He asked me to create branding for a new company that he was starting as a pharmacy chain—expanding the pharmacies that he already had—and I was able to create the branding for them. That’s where I saw the opportunity of getting into a professional field of design. So once I did that branding—I Googled what branding was and I was studying stuff like IBM and all these guys, just looking at what they were doing with the bold colors and textures and stuff like that. If you look at that pharmacy logo it’s very much inspired by that era [chuckles]. From there, it actually went off really well. I was able to learn a few things, how to work with print shops to get the logo right and do small things like that. That opportunity was huge for me. I think that really changed my direction of where I wanted to be headed.

“Anything I was able to get my hands on, I learned it by myself, and probably in the best way possible by grinding through it and doing extra class projects that weren’t mandatory.”

At the same time, the internet was really intriguing for me. It was really slow, [chuckles] it was painful in the Dominican Republic. We didn’t really have good internet there for a very long time until recently. I was super interested in web design, but I knew that my interest in particular was graphic design. That’s kind of what it was classified as. Just graphic design. At that time a lot of the schools that I was looking into when I was younger—during high school and after high school—they were all just advertising graphic design. I didn’t really know there was a web space or a product space. I think my abilities to see something and kind of shift to it what I thought was important—something that I knew was going to be big or huge at the time—is what also helped me a little bit. Taking matters into my own hands and learning things that I want to learn and doing things that I want to do, as stubborn as that sounds, is something that just helped. I never really spoke to my parents about my professional career, what I wanted my professional career to be, and that’s also helped, and they just let me do it. I went to school and did whatever I could do to get by.

I’m curious, I grew up in a very small town in North Carolina, and I don’t even think I heard the word “creative” until I was maybe sixteen. Where did you first get bit with the creative bug? Where were you when you were introduced to design as a concept?

It was in Manhattan actually. When I was really young, I took art classes in public school in P.S. 75 in New York. At that time, all my teachers really loved that I was super creative. They would push for me to continue being that way, and I remember right before I graduated junior high school, one of my teachers was pushing me to try and go to La Guardia high school, which is a design art school in New York city. So, I kind of had the knowledge that, “Hey, there is a design art field out there.” And really it just stuck with me. This is what I want to do, I’m really happy, and people enjoy my work. So at a very early age, I think living in New York just opened me up to that idea. And then after moving back there for college, I got to concentrate and just focus on it because there were very little distractions for me.

So walk me through the path from designing logos in your hometown to being in the middle of Silicon Valley.

So that was a little interesting. There’s going to be a little bashing in here. So when I was looking for colleges in New York—since I was technically a citizen at that time—I was able to look at U.S. colleges and I told my dad that I wanted to go to college and I’ll pay for it if I have to do it. But I want to do it in the U.S. because it’s design, right? In the Dominican Republic none of the universities taught design or had a big design field. There was one that partnered with Parsons but then still, I’d have to go to Parsons to be able to do a Dominican Republic kind of thing? So I decided to just bite the bullet and go. One school that accepted me and gave me somewhat of a scholarship was New York Institute of Technology. They’re a technology school in New York and had a graphic design program. And I was like, I’ll give it a shot and see how it goes.

“It was 2008, there was the peak of the recession. And it was so hard to find work, I think I probably interviewed like 20, 30 times with a range of people.”

Once I started there, it was kind of immediate to me that they didn’t seem to really specialize in the graphic design field—it was very much a traditional design kind of curriculum. But at the same time, I was starting to get into web design, and just the web in general. So there’s a few things that I did in college that leaned towards web design. I was already really proficient with different programs such as Photoshop, Illustrator, and Design. Anything I was able to get my hands on, I learned it by myself, and probably in the best way possible by grinding through it and doing extra class projects that weren’t mandatory. I’d even say that I was way ahead of the school curriculum, because they were trying to teach us those tools that I already excelled in. So during that time, I guess I just decided to learn HTML/CSS for one, which is probably the best thing I did in college—opening up code books and starting to learn it. In fact, that helped land me my first job and I’ll get to that later. Learning HTML/CSS during school was challenging because it’s not a school that was—it was very traditional, we were just drawing type on paper and learning lettering, whatever traditional graphic designers learn. But I love tech. I love anything that has to do with tech. I was into computers a lot so I got enough to afford a nice system that I just started to work on. And then I began to learn how to code, little by little, starting by building basic webpages and learning a little bit of Flash—something that I’m actually really happy that I dropped after a while because eventually it didn’t end up being that big, luckily. At that time people were like, “Flash this, Flash that, do Flash!” And I’m like, “ehh, no, no. I’ll learn how to build a webpage first and see how that goes.” And luckily I did that because soon after, Flash just died down really quickly.

Yep.

So I went through four years of college, four years of drawing and design and all that. It’s stuff that I enjoy doing, but I knew that in order for me to do what I like to do, which is like building things, and just being a part of a team, and doing stuff like that, web was like the place to be. I did some freelancing graphic design, and I wasn’t too happy with it. I freelanced for Scholastic Books for a while, and at that point, I just felt like it wasn’t challenging enough. It was a lot of small effortless jobs, doing a lot of designs that had already been done. There was not much room there to innovate and really excite me. But, when I looked at the web, it was the opposite. There was a lot there that wasn’t boring and I feel like at that time, I was reading articles about places like Facebook, and Google for instance, that were really interesting into how they built things, and how things were so new and fresh and exciting. So, once I graduated, I started looking at web agencies, like Huge Inc., and places—and small startups here and there, in Comcast. You know, things that were a little bit more in a digital range, to see if I could get my foot in the door and started learning more. Luckily, one of the startups, which was Livestream, allowed me to come in at the time. Mind you, at this time, it was really, really difficult to find work. It was 2008, there was the peak of the recession, [laughter] whatever the recession was. And it was so hard to find work, I think I probably interviewed like 20, 30 times with a range of people. When I interviewed at Livestream, they were just looking for a junior web designer, and one of the requirements was to hopefully know how to code. I actually had some prior knowledge of coding but I wasn’t great. And then I was like, “Yeah, I’ll take it.” It’s my first job and the only one that really gave me a concrete offer and I was just like, “I’ll do it.” [laughter] And that was my door into product design, and then that was my path. It was awesome at that point.

Were you still in New York at this point, or in Silicon Valley?

No, no, no, this is in New York. So, I went back to New York for college and I stayed there. Livestream is still located in New York and hired me after I graduated from college. Like, three or four months after college. Three or four months of excruciating job searching [laughter]. Yeah. It was also kind of difficult because my degree was for graphic design, so to prove that I can do web I had to build my own portfolio online. This isn’t something I would recommend anyone doing anymore because this is a new age, but I did some redesigns of websites that I thought needed the redesign and small things like that, but nowadays it’s not a great thing to do [laughter] so I would never recommend it. But at the time, anything was good to show and it was still kind of early, so why not.

What were those first years of work like for you?

Hard. I think I learned more in one year at Livestream than four years in college. It was extremely difficult. I had to really build my coding skills a lot, to the point where I was like a beginner and now I’m more than like—I’m pretty good [laughter]. And it was because of the fast paced work at Livestream. We had clients that required strict deadlines at the time, and I was doing a lot of custom development for some clients, so I had to build these Facebook apps. At that time, Facebook had page apps so I was doing a lot of that stuff, so designing them and then building them, and sometimes I had to build three or four apps a day.

Wow.

It got insane, yeah. It was really a lot of work. And then throughout that time I got to learn a lot about iconography and building UI and all that stuff. I was able to design one of their first iPhone apps and one of their first iPad apps at the time. That was all extremely exciting for me because the iPhone and similar gadgets were on the rise. I’d say I’d learned so much during that time. I was at LiveStream for four years, and those years were all difficult.

That’s a whole lifetime in startup years.

Yeah, I guess I got a little, I don’t know. Yeah, I don’t know. It was interesting. It was a lot of exciting work. I was learning a lot, so it kept me very busy and entertained. I guess I didn’t see myself needing to go anywhere.

I started at a very, very low salary. This is like a common story for a lot of people I bet. Especially women and minorities in general. Towards the tail end I started noticing a few patterns—I had to go through tough salary negotiations where I could get a livable wage. Even then I didn’t really feel like they wanted to take care of me, so eventually I just left.

“I’m happiest when I’m given the biggest challenges. It’s just like, ‘Look. We have something that we don’t know how to do. Can you help us out?’ And I’m like, ‘Yeah, let’s build a house [laughter]. Why not?’ I’m that person. You give me some crazy task and I’ll probably give it a try and see where I get to. It may not be perfect. I’ll probably warn you and be like, ‘Look. If it fucks up, I’m sorry [laughter].’ But I’ll give it a try. I’m not really scared of challenges and that’s helped my career out a lot I think.'”

It was really difficult at that time. A company came up to me—well actually a recruiter came up to me with an opportunity to kind of lead design at a small company, and I took it. This was just another step of a lot of learning. The company was called NewsCred. They’re still around and also in New York. I interviewed with them, and met their CEO and immediately we clicked. I was able to help lead their product design for their company. It was new to me, because I’d never led a team. Not anywhere remotely to that so again I had to quickly learn how to build a product from scratch, basically on my own from a design perspective, to actually being the UI engineer as well because we were really short staffed. So there was nobody to do the front end work.

So in like a year we built a product, a huge product for marketers that was like huge for them. And it was a huge win for me career wise, and that’s where I got, I guess that’s where, I still don’t know how Facebook found me, but that’s eventually how I came to Facebook a year later [chuckles]. Yeah, so it’s kind of a long road. There’s a lot of things in between.

I can relate. When I worked in start ups of like you’re just taxed with doing things you’ve never done before and you do whatever it takes to learn to learn them and do them. I’m just curious—when you encountered that atmosphere on day one of your first job, did you automatically feel like, ”Okay yeah, cool. I’m going to learn that shit and I’m just going to do it,” or were you just terrified? Did you have to go through any sort of personal process to convince yourself that you could do this stuff or did you just resolve to go do it?

No. I can do it, I’ve got to go learn it. I think that’s me. I think the last one’s me.

I’m happiest when I’m given the biggest challenges. It’s just like, “Look. We have something that we don’t know how to do. Can you help us out?” And I’m like, “Yeah, let’s build a house [laughter]. Why not?” I’m that person. You give me some crazy task and I’ll probably give it a try and see where I get to. It may not be perfect. I’ll probably warn you and be like, “Look. If it fucks up, I’m sorry [laughter].” But I’ll give it a try. I’m not really scared of challenges and that’s helped my career out a lot I think.

I think being a little brave and a little naive has helped a lot. Even with NewsCred, they knew that I never led a team before, but then they gave me a big task and knew that I could run with it and build something. In the few months that I started there, they had an idea of what they wanted. I was able to provide some kind of vision and just keep going with that and that kind of momentum it sticks to you early on in the production process. Once you’re able to at least come up with a defined vision and idea, it’s just like, “Yeah, that’ll stick. Let’s try and execute.”

“I think if you get scared about doing any minimal task, then it’s going to be harder for you down the road, because problems usually just get bigger.”

I feel like I’m the perfect person to be on product because it’s like I have enough experience now and enough know-how—I’ve made so many mistakes throughout the years—just kind of a better idea of where things should head in general. I was able to use that knowledge that I’ve built up from Livestream, all the mistakes that I’ve made and just like—let’s start over, let’s try something new and see how that process works. Maybe I’ve just been really lucky.

Anyway, it’s—yeah, I think that’s what works for me. I think it’s just—the bigger the challenge, the more excited I am and that’s a good thing for product designers.  I think if you get scared about doing any minimal task, then it’s going to be harder for you down the road, because problems usually just get bigger.

Totally. What is the most exciting thing to you about working in Silicon Valley right now, like building tools that are used by a billion people around the world? What do you love about your work?

I build tools for advertisers, so I’m on the advertising side of Facebook. And these are tools specialized for agency advertisers. This field excites me a ton. I think what we call business design is something that’s usually overlooked by a lot of designers. I think a lot of designers, like the more higher-visibility work and the nicer mobile apps and stuff like that. But I get more interested in complex challenges and complex problems. And being in business design at Facebook actually makes me super happy, because it’s a field that’s still kind of relatively new again, and this is something that I learned at NewsCred as well. NewsCred was also kind of like a B-to-B, it wasn’t like a B-to-C. And doing that I actually learned that, “Hey, this is actually a pretty cool field.” You can do some great things. What we’re trying to do at Facebook is humanize our products, and make those products easier for everyday use for advertisers. It’s a great challenge. Working for Facebook, at this scale—even at the scale of advertisers that we’re working for—is pretty insane. There’s a lot of pressure, but at the same time there is a lot of, how do you say that—gratitude?—for the work I’m doing. Is that right? I don’t know if that’s the right word.

Value.

Yeah, it’s super fulfilling. Honestly, Facebook is an awesome place to work at, just in general. I feel super grateful working here. It’s kind of like you’ve made it, in a way, especially for somebody like me that’s just been all over the place—just jumping left and right, crawling my way up. Then you’ve reached the top, and you’re just like, “Woah. This is a different world here. It works differently.” I’ve been extremely lucky. Just the path that I’ve taken and coming here to Silicon Valley—it’s great. I’m working with like-minded individuals—super smart individuals—and get to work with great designers that I look up to everyday—people that inspire me everyday. We just build off of this huge momentum and keep working on these great products all the time.

I love how the work that you’re doing ties back to the original work that interested you in the first place—designing for businesses as a kid.

Yeah, it’s great. I’m at a perfect place now. I’m an illustrator as well, so at times I miss doing consumer work in a way. I do miss that side of it a little bit but at the same time I’m super happy where I’m at. I come to work smiling every day. I’m one of the happiest people that comes in. Just knowing where I’m at now and just working with the people I work with, I’m super happy where I’m at.

“I feel super grateful working here. It’s kind of like you’ve made it, in a way, especially for somebody like me that’s just been all over the place—just jumping left and right, crawling my way up. Then you’ve reached the top, and you’re just like, ‘Woah. This is a different world here. It works differently.'”

What were your first impressions of Silicon Valley when you got here?

I was scared. I had no idea what to expect. One, I was one of those kids that just like loves small companies; loves small families. I used to bring the culture as much as possible to every small company. I’m the one that organized the karaoke events; the beer Fridays. I loved having that culture and building those things and working with people that just like to have fun while they’re working. So I was actually really scared. I read a lot of articles at the time that were like, “Oh, big company culture. Cubicles,” this and that. And then I was reading a lot about Facebook who tried to break down those barriers a little bit.

So that interested me a little bit. I was like, “OK, this is open, weird culture.” Still, what’s the top-down level? I’ve always had to deal with some kind of hierarchy that made my work a lot harder and at times—I was still scared. There’s so many people, and so many hurdles. Will I still have the control that I enjoy in my work, and would I still be able to influence and provide any kind of impact to the work that I’m doing? How many people am I working with? Am I just going to be editing buttons, and text inputs, and stuff for weeks? That would put me to sleep.

I came and interviewed, and even after the interview I was a little skeptical. I knew that the place was awesome. I was like, “Wow. This place is cool. This is like Disneyland for adults. It’s crazy.” Then I thought “How many other opportunities will there be for me to work at Facebook?” Why not give it a try? It was a company that I’ve always looked up to, and the design, and product work that they’ve been doing. Their mission is something that I have always—who can’t agree with their mission? It’s amazing, right? So I ended up biting the bullet and doing it. I don’t think it was a bad decision at all. I think it was actually a great decision. It’s worked out really well so far.

Awesome. What do you think are your biggest motivators or influences?

The more I talk to designers here, I always feel like they have specific examples of what these things are. I am going to be one of the few people that will tell you that it’s hard to say what it is. The challenge of the problems motivate me more than just specific people or influencers. I don’t have any influencers that are really big. I’ve always tried not to get too influenced by people, because then I feel like my work will depict that exact thing. It can be very easy to fall into that, but it is a good question, and I’ve never really thought of it that way. The people that influence me all the time are my coworkers. My immediate coworkers. The people who along with myself, solve these problems together. Also, just the problems, themselves, and who we’re solving these problems for.

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

The way my life has been, it’s kind of been all over the place. It shows that I’m not afraid to try new things. And that is exactly how it impacts my work. I’ve always been able to try and challenge my limits and try something new and push outside of my comfort zone, right? And that’s really defined a lot of my work. I’ve been able to do a lot of things with that like at Newscred and be able to build a new product that looked nothing like anything out there for the field because I can keep pushing and looking away from competition and trying that. I think that’s how my life has really benefitted my work, it’s just like don’t be afraid. Try it, do it and see what happens.

Yeah, for sure.

Even with Facebook I’ve been able to do that. Which sounds weird but, yeah, I can.

How do your family and friends from home feel about how far you’ve come and all the work that you’ve done?

You know, they don’t say much. [laughter] I think though, honestly—I know they’re very proud of me. My dad is super successful. My whole family is a huge success I think, and I’m really proud of them and they’re excellent people—amazing people. And having their support all the time has been—it keeps me going, makes me super happy. And my wife now too, she’s super supportive, she’s one of the best people—the best person I can be with right now and makes me super happy. We’ve been together for like eight years so she’s been through a lot of this stuff that I’ve been going through. And I guess back home, my family, they’re just very super happy, like always positive people. That’s kind of how I am and when I go home I’m just part of the family, I’m not any different really. And I love it that way, that’s how I want it to be.

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

Oh shit, that’s a good question.  You know, to be honest with you, I’ve always had a dream of finally owning what I’m building at one point. I’ve built so many great things for so many different companies and people and users, and I still want to build for users and people all the time. But I do want to eventually maybe do my own thing, like have my own creative business or boutique or whatever. And I’m really still kind of open to that idea, I’m hoping it just lands on my lap somehow, which it probably won’t, so I don’t know. We’ll see.

Well, I mean the cool thing about your work experience—having just done so much different stuff—you’re the kind of person who’s perfectly equipped to start your own thing later, you know?

Thank you for that. That’s a nice thing, I’ve never heard somebody say that.

Having done it myself, I’m so glad I worked in tech doing a million different things. And now I’m a photographer, but all of that stuff I did before is such a huge reason I’m successful. It’s so good to learn all those random things. It doesn’t make sense immediately, but it does later.

How’s that been for you? This is kind of like your own thing, right? I mean it’s super impressive.

Just a side project—that’s gotten really big.

I love your work by the way.

Thanks. Yeah, I mean it’s the best decision I ever made. You know, I still get to tangentially pop in and out of tech, and be involved however I want, but I work for myself, and I have complete control over who I work with, and I make way more money, and everything is better.

Yeah, that’s so cool. Yeah, it’s one of things like, you know, people have never had their doors open for them. It’s like I feel like I can do it, right, I’ll just work through it and find something great and do whatever I can. That’s a nice thing to have I think. I feel like my career, even though it’s been like painful a lot of times, is like, “Hey, I got here mainly on my own, just as much as possible, just working hard, and doing what I love.” So the creative field’s great. I love the field, it’s awesome. [chuckles]

Okay, last question, this is important. What advice would you give to folks from similar backgrounds to you, who want to get into tech?

Yeah, it’s an easy and hard question, because I feel like the advice I would give them would be very similar to what I did, right? But at the same time, I feel like the field itself has transformed to a lot of the young designers have learned things that at one point, I was the one learning it on my own, and these guys are learning it from school or on their own as well. I feel like the hacker mentality of building things and doing things that are unknown, is so much more natural these days than it was eight or nine years ago. It’s interesting because my advice to them—to the young adults coming out of college [chuckles] with a lot of knowledge in the tech industry and products and being surrounded by products is just take it all in and try and build things at all times. Build the smallest things to the biggest things. Just try and build stuff really. We’re all builders and even if it’s just a coffee table or any small thing, it’s important. It’s something that you’ll learn from. I would even say start small. If you want to start big, go ahead [chuckles]. There’s no real wrong path as long as you’re building and working. It’s funny because like five years ago, I would’ve been able to give you a better answer, but now days, I’m like, “These guys are doing pretty good.” I’ve seen a lot of these young university students graduating, and I’m super impressed by their work.

What about any thoughts for the Dominican Republic, your homeland?

For the Dominican Republic, I want them to take design more seriously because a lot of it is still thought to be extremely superficial, but design can do a lot of things to better a country in general—there’s a lot of possibility there. It’s not just graphic design anymore. In order to do that there needs to be work done around access to the internet. I know the internet is still extremely expensive and inaccessible for most of the country, but there’s so many things that you can do online right now that can help grow and nurture existing and new businesses while opening doors for engineering and design.

I hope it gets to the point where we can just have a lot of people like me just move there and work. One day, hopefully that’s the case.

“Just take it all in and try and build things at all times. Build the smallest things to the biggest things. Just try and build stuff really. We’re all builders and even if it’s just a coffee table or any small thing, it’s important. It’s something that you’ll learn from. I would even say start small. If you want to start big, go ahead [chuckles]. There’s no real wrong path as long as you’re building and working.”

“Being an immigrant taught me from an early age to observe carefully. The thought was always, ‘This is how things happen here,’ and not ‘This is just how things work.’ That probably influenced my observation skills from a pretty early age. “

“When I’m seeing people like 10, 15, 20 years older than me in leadership roles that are not like me in any way, it’s really hard to imagine yourself and what you’re working towards.”

“When I went to my first Women in Design talk, it was really the first time I saw women who had careers I aspired to in front of me, and it really did hit me, wow, this feels more reachable now. Hilariously—but in a sad way I guess—I was one of the people who was giving a talk. So you have be your own role model sometimes I guess. And that’s hard.”

“As many people do, I’ve often asked myself what my career goals are. But kind of related to the role models point, it’s hard to be able to point to someone and say, ‘I want to be that person.’ And It’s not cut and dry, like I’m a lawyer at a firm and I want to make partner. So all I’ve really had as a goal was I just want to learn and do something that it makes the world a little bit better.”

“We need to look at solving problems that are beyond the cushy, privileged problems. This is why diversity in tech is critical, and not just a nice-to-have. We need access to a wider set of problems.”

“Ask a lot of questions. Because there’s a finite amount of careers that are told to people when they’re ten and fifteen and even twenty. It’s like, doctor, lawyer, now engineer. But there’s all these jobs out there, and if you ask around you might find one that will fit your interests and strengths and things you’re excited about.”

I come from Canada.  My dad is an engineer and he always raised me to think about solving problems and building things, and my mom reinforced that too. I was one of those kids with a magical upbringing where I thought I could do anything. I thought the major problem with being an astronaut was that I needed glasses since I was five, not that I was not a man (there were no female astronauts yet). I didn’t think of myself as a girl or as a boy either, just as having unlimited potential.

I was socially very inept. I didn’t really know how to make friends. I could play with kids, but I didn’t know how to have an emotional girl relationship despite the couple of girlfriends who did their best to teach me because they were stranded with me in a small town. I was the top of my school in high school and just absolutely knew I was either going to become a professional musician or a professional engineer, and I had no doubt about being able to do either. And I picked Engineering, because I could always do music as a sideline.

“I was one of those kids with a magical upbringing where I thought I could do anything. I thought the major problem with being an astronaut was that I needed glasses since I was five, not that I was not a man (there were no female astronauts yet). I didn’t think of myself as a girl or as a boy either, just as having unlimited potential.”

Of course, I found university much harder than high school. Socially, again, I was still having huge problems. I was finding some friends that were amazing friends, who had the same interests as me, and we were connecting a way I’d never connected with other people before. Like the friends that I played “Magic: The Gathering” with after classes, and the friends I traveled to Gen Con with—the big gaming convention in the States. I traveled to Milwaukee from Kitchener-Waterloo for that convention. My studies were hard because now, I was with a hundred other students who had been the top of their classes. So I think that’s a pretty typical experience for men and women in Engineering.

I felt isolated for sure. I never knew how to analyze these things at a young age, so I was just oblivious. For example, I lost a friend in my first term who had been my roommate. After first term was over and we went off for our work terms and came back, I eventually realized she was no longer my friend, and I really must have been a social idiot to not know what I had done to make her not be my friend, and to take so long to realize that I had become not her friend. And by the time I realized, it would have felt really awkward to say, “Hey, why haven’t you been my friend for the last few months?” Like, to admit that I only just noticed. But I was so oblivious that at that age I could basically only shelve that information and try to understand it and process it later.

I really love solving problems and building things, and building on other people’s ideas. So my most successful times in University was when I got to do that, when we got to work on something together.  Sometimes it was outside of class like doing a creative writing workshop, and sometimes it was inside of class, like where we had to build a cardboard bridge for the Physics of Materials class. I knew that I would find that in industry, especially if I didn’t take a solitary engineering role. If I took a programming role and I stayed in front of my computer all day, or at least that was my image of it, then I wouldn’t be solving problems with people and be quite so collaborative. I’d be more isolated.

What I didn’t realize and what many people don’t realize is that engineers, even the ones who are called “individual contributors” are still incredibly collaborative. It’s hard to be an isolated engineer in the modern software industry. At least I was exposed to industry through my work terms. One of the fabulous things about my school was sending engineers off on work terms, six times in all. It was a five-year program so that they could send us off from January to April or send us off from June to August or send us off from September to December. So year-round, there would be engineering interns going off in all directions and some companies had this constant stream, not just summer interns, but a year-round rotation of interns coming through. And that exposure was fantastic for showing me that there were jobs that were people-oriented and collaborative. So the same thing I love about music, which was playing in an orchestra, I found that in computer science. It was initially being a program manager to bring together engineers with requirements and users and constraints and testers and making it all work, not instructing everybody what to do. So not like a conductor in an orchestra but the coordinator, the hub, the person who—by sharing the right information with the right people at the right time—could just make everything run smoothly.

What originally brought you to Silicon Valley?

Well I did have that moment of awe—of driving down the 101 and seeing one sign after another. In those days, it was seeing Sun and Oracle and AOL Online and Excite at Home. All of these signs along the freeway of companies I recognized—of innovative companies, one after another. So it was really fun to do that. I visited Silicon Valley from my first job up in Seattle before I moved to Silicon Valley. I spent four years in Seattle after university and I visited for conferences and meetings and things like that. And I knew where the interesting stuff was going on.

I wasn’t a good fit at Microsoft because it is a big corporation.  It can be a shark tank, rat race or whatever animal model you care to choose. I found a romantic interest in the Bay Area, and when the time came that I felt comfortable moving closer to this romantic interest, I was also quite happy to leave Microsoft and look for a startup job. And I found one and it was wonderful. I got to hire engineers, and build a team, and design, and code.  In order to get that job, I had to pretend I was more of a programmer than I had been for the last four years, but then I quickly had to make good on that promise. I know from reading the literature that not all women feel comfortable doing the fake-it-till-you-make-it thing. They underestimate their abilities rather than overestimate and I certainly overestimated my abilities, but I had the incredible support of a romantic interest.  He just thought it was a no-brainer that I could do this and he gave me a lot of confidence. The confidence of a parent or of a boyfriend can be huge for giving that boost, making the ask, applying for the job, saying, “Sure, I can do that.”  

“A calendaring standard had been marinating in my head for years. I finally figured out I could make a proposal that people would be interested in. I made a proposal of, “Here’s the smallest thing that we could build as a calendaring standard, that we could implement and inter-operate between calendar servers and calendar clients”. That’s the interaction when you open your calendar and you get it from the server: something new will show up on the phone and you’ll see it even if you entered it in your computer. That was what I wanted to solve first—not invitations or scheduling—but synchronizing that specific kind of data between devices.”

What are some of the proudest moments of your career?

I think the thing I’m most proud of happened after working on Internet standards for years, after I worked on some standards for document sharing and Web standards. Because I was involved in that while I was still at Microsoft, I was sent to look into the calendaring standards.  Not that Microsoft wanted to do anything but it needed to have somebody there to fill the seat at the table. But I was exposed to that so four years later, I had another chance to look at it and I had these ideas. A calendaring standard had been marinating in my head for years. I finally figured out I could make a proposal that people would be interested in. I made a proposal of, “Here’s the smallest thing that we could build as a calendaring standard, that we could implement and inter-operate between calendar servers and calendar clients”. That’s the interaction when you open your calendar and you get it from the server: something new will show up on the phone and you’ll see it even if you entered it in your computer. That was what I wanted to solve first—not invitations or scheduling—but synchronizing that specific kind of data between devices.

So we should all literally be thanking you for being able to use our calendars. Thank you.

After that, I went from writing my own standards and leading working groups to actually directing a part of the IETF. Web standards, email standards, calendaring standards, instant messaging standards, and a few others; all the ones that people think of as the Internet. I was one of the directors of that area for four years (which means I got selected twice to do that). That was incredibly political work with a long-term horizon. And so, I was not just writing a document anymore that might become a standard. I was getting the people together that might form a working group, that might choose an editor, that might write a document, that might be edited, that might be approved, that might be implemented that someday people might actually use in their software. There are so many stumbling blocks on the road, in such a political process, to get approval to start these things to get community agreement. It was all about getting community agreement, getting consensus and the technical issues became sore points rather than the fun parts, because the technical issues were wrapped up in people’s egos and politics.  

“I went cold turkey on standards. I had been doing it nearly full time, it was nearly my whole job, and then I went away, I completely stepped away. I’ve never been back to one of those meetings. I didn’t mean to make a dramatic exit, but I was done.  No hard feelings against anybody in particular, but I was just done.”

I really did burn out on that kind of work, and I decided to go for something completely different. Instead of this ten-year time horizon, how about a two month time horizon?

So I went cold turkey on standards. I had been doing it nearly full time, it was nearly my whole job, and then I went away, I completely stepped away. I’ve never been back to one of those meetings. I didn’t mean to make a dramatic exit, but I was done.  No hard feelings against anybody in particular, but I was just done. I’ll do something new; I’ll figure out a new career. I guess another thing I was scared of: there are some cantankerous curmudgeons in these standards groups who have been there for twenty years, so I gave myself ten. I figured, if I don’t become a cantankerous curmudgeon in ten years, great, I’ll give ten years and that will be useful to the community and to the internet, but after that I should go, because the last thing I want to become is one of these people who says well, you can’t do it because of this, this, or this reason—always complaining and saying “you can’t, you can’t.”

What are some of your favorite things about working in tech?

The technology industry reinvents itself over and over again. Younger people or newer people come in and overturn the status quo. If I can’t make myself young again, I can at least make myself new again [chuckles]. I can jump into something I haven’t done before, and ask questions, and say, “Wow, why can’t you do that?” Or, “What if you did it this way?” Startups have turned out to be a place where I can perennially do that.

A lot of people want to say, “What industry are you interested in doing a startup in?”  This comes up when I network, which I do constantly trying to find my next startup. If I am in a startup for a year, that’s great, but I’m constantly networking because it takes time to find another startup. When I say, “Do you know any interesting startups?”, people say, “Well, what industry are you interested in?” Well, anywhere where I can be useful and new at the same time.  Where I can have that excitement of digging into something new, and the utility of bringing this pattern-matching experience, like the experience of looking at big systems, and deep diving into protocol issues, and various startups—bringing all that experience to a brand new problem. It’s pretty useful [chuckles]. I can say that with confidence.

What have been some of your biggest struggles and roadblocks?

So some of the first problems that I ever had an inkling of were the problems of camaraderie.  I’m pretty sure what screwed my first term at university was a little bit of sexual liberation, of looking like a sex object to the guys in engineering. That meant that I couldn’t be a colleague, or couldn’t consistently be a colleague. Oh my God, once a guy in first term engineering from another class ran into my classroom and dumped a box on the table in front of me, in front of all my classmates, just before class started. They asked, “What’s that?” I looked, opened it up, and it’s a necklace. Instead of saying, “Oh, what an idiot that guy is,” they all looked at me: “What did you do to have this guy dump a necklace on you?” It made me stand out and be judged. Was I making women in engineering look bad? Well, it was my first time in college! Duh! [chuckles]

“I’m pretty sure what screwed my first term at university was a little bit of sexual liberation, of looking like a sex object to the guys in engineering. That meant that I couldn’t be a colleague, or couldn’t consistently be a colleague.”

Anyway, I was kind of shunned. That was really hard. I toned everything down. I started dressing more conservatively again. I stopped flirting. I resolved, “Maybe I shouldn’t have coffee with guys. We’re either working on homework or I can’t have coffee with you.” I made all sorts of restrictions like that and I became much more conservative again and good girl and serious and keep my glasses on more and my contacts in less. All the little things of holding myself to a mold that would not be mistaken for a sex object. Instead, geek girl: the geek girl mold allowed me to reclaim some camaraderie.

It’s not always possible. The first team of people at Microsoft that I loved working with and I wanted to be part of the team as much as anybody else on the team, well they played basketball together. Actually, I played basketball in high school and I missed it, so I thought, “Oh, this is great! I’ll come play basketball with you guys since you say it’s a casual pick-up game.” But after a couple times, they started sneaking out without telling me they were playing basketball. My best guess is that they didn’t like bumping into me. I was the only girl on the court. They didn’t want to hurt me. They didn’t want to come down with their elbows and get me in the face. They didn’t want to have to treat one person on court differently. They just didn’t want me in that pick-up game, so they stopped letting me know when they were going and it was clearly not working, so I needed to find other ways of finding that camaraderie. I did. I played networked computer games and I loved them. In many ways it was easy for me because I love video games. I got into juggling, I just did all kinds of geek stuff. I’m like, “Sure, I’ll do that geek thing, because here I am among geeks and it’ll be fun.” I really did enjoy that. But there were some sore spots there too.

“I was kind of shunned. That was really hard. I toned everything down. I started dressing more conservatively again. I stopped flirting. I resolved, “Maybe I shouldn’t have coffee with guys. We’re either working on homework or I can’t have coffee with you.” I made all sorts of restrictions like that and I became much more conservative again and good girl and serious and keep my glasses on more and my contacts in less. All the little things of holding myself to a mold that would not be mistaken for a sex object. Instead, geek girl: the geek girl mold allowed me to reclaim some camaraderie.”

Have you had other experience where you are treated differently as a woman in tech?

I do get underestimated. One of my favorite examples of being young and being underestimated, it’s very easy to walk into somebody’s office and just start asking questions like I need to learn this area, “can you answer some questions for me,” and ask a bunch of questions. But what I’m really doing is I’m getting time with a developer who would otherwise be prickly and defensive, and convincing him to change something that he holds dear by asking innocent sounding questions. And I learned to do it, and I felt manipulative, but it felt like it was really working so I tried to professionalize it.  I realized years later that what I was doing was the Socratic method. When you want to teach somebody something, and you ask them questions to arrive at it, that is called the Socratic method.

“One colleague who’s younger than me and less experienced than me, who thought it would be appropriate to give me some feedback after my first year as an Area Director.  He said, ‘Sometimes I think you don’t know the answer to something that I think you should know the answer to, so I think your weakness is you should be more technical.’ I had to say, ‘It’s called the Socratic method.’ And he boggled. He hadn’t considered that I really did know these things.”

Yet still I had colleagues… for example one colleague who’s younger than me and less experienced than me, who thought it would be appropriate to give me some feedback after my first year as an Area Director.  He said, “Sometimes I think you don’t know the answer to something that I think you should know the answer to, so I think your weakness is you should be more technical”. I had to say, “It’s called the Socratic method.” And he boggled. He hadn’t considered that I really did know these things. So all these guys who thought I was asking innocent questions, they underestimated me, and this colleague who knew me really well, we’d worked together closely for a year, he still underestimated me, thinking all these questions meant I didn’t really know any answers.

It take a lot of seniority for a woman to start being able to give answers instead of having to couch answers in questions, and I have gotten there. I still sometimes get horribly defensive and I hate to feel myself doing it. I start listing my credentials like I’m bragging to establish that I have that ability to give answers sometimes. Sometimes I’ll preface an answer with, “Here’s all the reasons why I’m going to give you an answer, and you need to respect that and not dismiss it.”

“I still sometimes get horribly defensive and I hate to feel myself doing it. I start listing my credentials like I’m bragging to establish that I have that ability to give answers sometimes. Sometimes I’ll preface an answer with, ‘Here’s all the reasons why I’m going to give you an answer, and you need to respect that and not dismiss it.'”

When I became a mom, something else changed completely. I started noticing that my commitment, my passion was now completely in question, and it hadn’t been before. When I was childless, I could be a geek—almost like people said, “Well, she must be basically a man in a woman’s body because look at how much she loves protocols, and architecture, and systems.” But then when I got pregnant and I very clearly was not a man, I noticed that was just overwhelming to people. People started saying things like, “Well, I guess you’ll be glad to leave work when you have the baby.” That had not been questioned before, and even the second time I had a baby, even though people knew I had previously had a baby and returned to work—the second time I had a baby, my board of directors was asking my CEO, “so are we going to lose our VP Eng after she has her baby? How do we know she’s coming back?”

It was when I had my first baby that I started reading a whole bunch of feminist literature and for a time period I became quite bitter and ranty. I started putting together patterns, like what had happened in that first time when I thought I was making friends in my engineering class and then the friendships collapsed and I had to find friends elsewhere in the university, in the math department and other engineering classes. I think I finally did analyze that correctly but I didn’t do it until 15 years later. After becoming bitter and over-educated about the barriers that I had been oblivious to, I started thinking, if only I could become oblivious again. I did manage to in some ways. I managed to put it out of my head.

“When I became a mom, something else changed completely. I started noticing that my commitment, my passion was now completely in question, and it hadn’t been before. When I was childless, I could be a geek—almost like people said, ‘Well, she must be basically a man in a woman’s body because look at how much she loves protocols, and architecture, and systems.’ But then when I got pregnant and I very clearly was not a man, I noticed that was just overwhelming to people. People started saying things like, ‘Well, I guess you’ll be glad to leave work when you have the baby.’ That had not been questioned before, and even the second time I had a baby, even though people knew I had previously had a baby and returned to work—the second time I had a baby, my board of directors was asking my CEO, ‘so are we going to lose our VP Eng after she has her baby? How do we know she’s coming back?'”

You’ve got to take every interaction at face value. I can’t assume that every interaction might be polluted by bias. I just have to assume it is what it is. “He didn’t like my idea. I didn’t convince him. I didn’t try hard enough. I didn’t put it the right way. He is not ready to hear it.” I don’t necessarily always blame myself, but I do leave it open. I don’t say, “Well, he didn’t listen because I’m a woman.” because that would just poison my life. I just say, “Well, it doesn’t always work. I’m not always able to convince somebody and what do I do now?” I just think that way. Take everything at face value.

I’m now at a point where I can identify in other women whether they are at that oblivious or denial phase or whether they’re at that eyes-open, perhaps bitter phase—and it is a phase change. You can see somebody making that phase change sometimes. You can see somebody approaching it and then stepping back if they choose to remain in denial.

“After becoming bitter and over-educated about the barriers that I had been oblivious to, I started thinking, if only I could become oblivious again. I did manage to in some ways. I managed to put it out of my head.”

How do you find balance between the two?

It’s more by compartmentalizing. In college, it was not possible to compartmentalize and even in my first few years out of college everybody made friends with everybody else from work. Being a cohort at Microsoft of new grads made us all potential friends. We sorted out into subgroups of close friends, but there was so much overlap between work and personal life that I couldn’t compartmentalize.

But I did manage to compartmentalize eventually. I found knitting groups and I expressed myself in fiber arts. I am a very technical knitter, no surprise. I knit some of the most challenging lace projects out there in order to challenge my brain.  I meet up with other knitters who are almost universally women and I geek out with them in a totally different way.  “Feel this fiber,” and “Yeah, this fiber that’s silk,” and “Oh my God, I could roll in it.” Knitters are wonderfully supportive and friendly, especially the geeky knitters, because nobody who’s a software engineer AND a knitter wants to exclude anybody, because they’re so niche already. I was able to go to contra dances, I was able to bring back the music into my life, and dress up girly, and twirl around in skirts in my thirties. I would leave work and go to a contra dance, and only if somebody asked, “what do you do?”  would I say, “I’m an engineer.”  I didn’t worry about being taken seriously because I’m just dancing.

“I’m now at a point where I can identify in other women whether they are at that oblivious or denial phase or whether they’re at that eyes-open, perhaps bitter phase—and it is a phase change. You can see somebody making that phase change sometimes. You can see somebody approaching it and then stepping back if they choose to remain in denial.”

What are some of your biggest struggles as a VP level woman in tech?

I’m finding ways to deal with it, but it for sure has because the number of decisions I have to make just goes up and up.  I’m not just deciding how to architect something, but how to tell somebody how to architect it, or whether to let them try it their own way and perhaps not do it right, and whether to hire somebody, whether to fire somebody.  Whether to make things blue or green – well not exactly, but that kind of low-level and high-level decisions all mixed in together in a day. And I get decision freeze sometimes, just where I don’t want to make one more decision, I don’t want to organize one more thing, or send one more email, or set up one more meeting. Because I do love my job, my social life has gone down.  Especially since having kids. I used to be the social coordinator for my geek group of friends in Seattle, and I’m just not that person anymore. I don’t have the capacity for it anymore.

What do you enjoy most about it?

It’s very high up the Maslow hierarchy of needs; it’s fulfilling work. It’s work that makes me feel, “I’m so excited to be putting together this picture, and sharing it with somebody else and including their ideas, and figuring out a way to picture it all so that we can convince the rest of the company to do it.” Those moments, I live for, and I try to seek them out.

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

We’re going through a couple of major changes that may be linked.  startups can build more functionality cheaper than ever with fewer people because we’ve evolved our web technology to be powerful and modular, so that you can build a little piece and hook it to five or ten other little pieces. When you build a website these days the internals are modular. You can pull in a module that does the login for your site and integrate that with a few tutorial steps and now you’ve got logins. Integrate a module that does image viewing and zooming; two days later you have image viewing and zooming. Those are both code modules that are open source, somebody else wrote, and you bring them into your project. But there’s also powerful services, for example pulling restaurants and photos people take in restaurants from Foursquare. You can integrate a service in a couple of days. It takes a lot longer to make everything work together smoothly, but the basic pieces can be pulled together so fast that a startup might only need one engineer to build its first product and show it. It might only need four months. It used to be that a startup always needed $6,000,000 minimum to get off the ground. The first startup I joined needed $6,000,000 and now people think that a couple $100,000 might get you off the ground. That’s more than an order of 10 drop and that is a game changer.

“You can integrate a service in a couple of days. It takes a lot longer to make everything work together smoothly, but the basic pieces can be pulled together so fast that a startup might only need one engineer to build its first product and show it. It might only need four months. It used to be that a startup always needed $6,000,000 minimum to get off the ground. The first startup I joined needed $6,000,000 and now people think that a couple $100,000 might get you off the ground. That’s more than an order of 10 drop and that is a game changer.”

I wonder it’s linked to the prevalence of women, or if it’s just coincidental that this has been the year of the women in my industry talking about getting harassed, women in the gaming industry particularly. Brianna Woo and Anita Sarkeesian. Twitter trolling happens publicly.  It always did used to happen, but it happened more in niches that fewer people could see. I’ve seen stories surface now about that happening 10 years ago. Where was the outrage 10 years ago? It apparently wasn’t surfacing high enough to be noticeable. I think that in the reaction to that, the backlash is happening because there’s pressure to change it for the better. The backlash is coming from people who don’t want that change.

I would like to see modern Web architecture, these modular tools that I was saying that make it possible to build stuff fast, and ways of working that give engineers a lot of autonomy—I would like to see those spread inside larger companies because I think larger companies have a lot of pent up, underused expertise and value. I don’t mind seeing big companies become better. I want to see Oracle become better and faster, and I still think there will be lots of room for small companies. It’s interesting to me how slow sometimes the adoption curve can be for something that, if you adopted it now, you’d be saving time within six months when the engineers are trained up, and yet five years pass before a company adopts that thing. There’s a saying in science, that science advances funeral by funeral. A generation of scientists has to be replaced by a new generation in order for a big idea to change the landscape and take over as the accepted idea. In my industry I think it’s the speed of hiring and firing—that a generation is how long people stay at a company. But I’m always excited to see that change happening, even if I think it’s inevitable.

“Twitter trolling happens publicly.  It always did used to happen, but it happened more in niches that fewer people could see. I’ve seen stories surface now about that happening 10 years ago. Where was the outrage 10 years ago? It apparently wasn’t surfacing high enough to be noticeable.”

Of course I want to see more women feeling happy about staying in technology. I want to see great paternity and maternity policies. I want to see it be okay for a guy to say he took time off to be with his baby, like one guy told me today.

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

I don’t. I have a best friend who’s a CTO or VP Eng at successive companies.  She’s my peer, but we go to each other for advice, supporting each other. I don’t really have mentors that I can look up to and model myself on.

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

I do. I love what I’m doing. And I have a lot of appetite for being in a small company. I often find being in a large company as stressful as being in a startup, which is not the normal experience. I find in a startup, the politics are at a manageable scale, and the priorities are very clear to everybody.   I can be a lot less stressed relative to other people in a startup. I don’t panic. When the services are down, you know it’s just a startup. It’s not 10 million people using it yet, so I don’t panic. I know people who panic in a startup because of being the only one there—the one in the spotlight. Well, I know people who panic at big and medium size companies too. But I actually think it’s more relevant when it’s a big company. Just because the blame can be spread more widely, doesn’t mean that an outage that affects 10 million people is better. It just has a bigger effect on the people who feel responsible. I’m able to put that in perspective when I work at a startup. It doesn’t have a lot of users yet, and so I say, “Okay, the system went down the weekend. We’ll write the tests to make sure it doesn’t happen again. No need to panic. Let’s just move on. Learn from it.”

“I don’t really have mentors that I can look up to and model myself on.”

So I see no reason why I won’t still be here in five or ten years. I would like to grow one of the startups that I join—and I know it’s never certain that I can do it—I would like to grow one of them to be a 200 person, a 300 person company. I want to be the CTO or VP Eng, one of the lead technical people. I don’t have to be the top. I can share responsibility very well. My co-founder in the last startup—we are excellent work partners. We fill in for each other’s weaknesses. I don’t do all the tech and he doesn’t do all the people stuff even though we obviously have strength in those directions. I could see myself sharing the responsibility at the top level of a company of 200 or 300. That’s where I’d like to be.

Lastly, what advice would you give to folks from similar backgrounds who are in tech or hoping to get into it?

Well, I find it hard to generalize my advice. I do give advice to people and I try to pitch it to the person where they’re at. I met an intern from my alma mater and she must be about 21. She’s in San Francisco for a work term and my advice for her was that this is a great time to meet with people. Say, “I’d like to pick your brain. I’d like to have coffee, and I’d like to know what you’re doing. I’d like to know why you started that startup,” and so many people will say yes if you reach out. Every person you have coffee with, you could say: “This is so great talking to you. I like what you told me about this. Can you suggest somebody else I could talk to in this area?” and they’ll suggest two more names. So, you can just go on having coffee with fantastically interesting people every week, and you will find it so rewarding to build that experience and that breadth of mindset.

So that was my advice to a twenty-one year old, and my advice to a twenty-eight year old entrepreneur was to get bloody minded, to stop worrying about the things that weren’t the most important things or whether as the founder of the company she should be doing engineering hiring. I said, “Is it the most important thing? Can you do it right? It is your most important thing. You need to do it right. Be bloody-minded about that. Push the boundaries. Go hunt people down and hire them for your startup. You can’t do the normal things.” So I was telling her to push the boundaries, use the bloody-mindedness to work the problem of hiring the way she would work a problem in math.

My advice for somebody who’s thinking about becoming a mom is to flex it.  Be flexible in your picture of how things are going to be. Be flexible about whether you’re going to have a nanny or a daycare. Be flexible about whether you’re going to cook nutritious meals yourself every night or whether you can hire a cook or bring your kids to the company cafeteria. Be flexible about everything and always be reworking the problem. Every year with kids the situation changes. Flex it.

Sure. My early years. I immigrated here when I was three. I don’t have any real memories of living in the Philippines, but that’s where I was born. I was largely raised in San Francisco, in a neighborhood called Bernal Heights. Back then, it was mostly just a blue-collar, lower-middle-class neighborhood. It wasn’t what it is today, which is starting to look a little chichi in some respects. Back then, security alarm systems for people were dogs in front of their houses that were loose and chasing you away.

I had to actually start going to school on my own at a pretty young age. I was walking by myself to school at the age of seven which can be a little scary in the city. Coming from an immigrant family, my parents were both working and they had asked my sisters for help with dropping me off at school, but they had their own world of stuff that they were dealing with. So, I ended up walking to school on my own. I was also a latchkey kid as early as five years old. It can be scary being at home alone, and so I had to learn to be independent and resourceful really early on. You have to be street smart and careful, so you in some ways you have to grow up too early.

“I was walking by myself to school at the age of seven which can be a little scary in the city. Coming from an immigrant family, my parents were both working and they had asked my sisters for help with dropping me off at school, but they had their own world of stuff that they were dealing with. So, I ended up walking to school on my own.”

You kind of lose that sense of innocence about things that kids should really enjoy. Like Santa and the tooth fairy. My parents, up front, when I was around five or six, told me there’s no such thing as Santa Claus and there’s no tooth fairy. I’ve been happy as a mother to see that innocence through the eyes of my children. I think that it’s wonderful to keep that in our young children for as long as possible, because the pragmatics of life will set in soon enough, and there’s no need to do that too early.

I started playing tennis when I was seven. My dad would play tennis on the weekend, from around six in the morning until noon, and so I’d hang out on the courts with him while he played with his friends. I would mostly go hit against a wall to practice playing tennis, and then he would spare half an hour or so to play with me at the end. As I got older, there was this national program during summer breaks that was cofounded by the legendary American tennis pro Arthur Ashe called National Junior Tennis League (NJTL). They were for inner-city kids to keep them out of trouble, because they knew that a lot of people couldn’t afford summer camps. I was one of those kids. I started playing more formal tennis and I was getting more actual lessons through that, which was a wonderful, wonderful program. That’s where I started really competing against boys in tennis, and really becoming a power hitter and really just enjoying that sport.

I really believe that, especially as a girl, playing sports helps with development in math and science and the confidence you need that lots of girls lose as they get into their teen years. I didn’t experience that lack of confidence and I attribute it to my participation in tennis. There have been some studies published about how girls (especially those participating in team sports) do much better in math and science. It’s actually the opposite effect for boys. It makes them much more aggressive. I’m grateful for the  experience of sports as a regular part of my life growing up. I’m also grateful for the fact that when I was 16, they (NJTL) gave me the opportunity to be one of their teachers.  At the time I was the youngest teacher they had ever hired and I taught both in Oakland as well as San Francisco. That helped me start exercising some leadership skills early in my life. I really appreciated that opportunity and that responsibility, and also being able to give back to kids in the neighborhood.

I started my interest in computers fairly early. This is way back when everything was command prompt driven. There was no user interface. There was no Windows. It was DOS-only green screen. Those were the early days of primitive spreadsheets and word processors. But it was interesting to use a computer back then – not everyone had one so it was novel. I grew up in those early days of using a computer when there was no Internet for the public. That didn’t happen for a while. In retrospect, it was a little less interesting too because it was more isolating since there was no social network to leverage. There weren’t any online resources to learn more about tech. The ability to learn from online communities and research was tough unless you were going to college and could get in those kinds of classes, which were also limited in those days.

“I started my interest in computers fairly early. This is way back when everything was command prompt driven. There was no user interface. There was no Windows. It was DOS-only green screen.”

My family situation was really difficult. We were an immigrant family and my parents had difficulty adjusting to the American culture. I was also the youngest of four girls but my sister who is closest in age—she’s about 2 years older than me—was born mentally retarded and her mental capacity is at the level of a three or four year old. Even though I’m technically the youngest, I’d end up spending a lot of time taking care of her. I would sit and do flashcards with her to try to teach her the alphabet and numbers. When I was a teenager I remember taking her to some of her doctor appointments and navigating the bus system with her to get there. It gave me a lot of responsibility really, really early on in life. I had my hopes of where I wanted to go and wishes for success. I did very well through most of my academic career, so I had these lofty goals to go to an Ivy League college at some point. I had made it to a top high school in San Francisco (Lowell High and they were rated really, really highly back then). I wished to go somewhere like Harvard for college but because my family life was really difficult, I had to make the decision to just compress my high school education as much as possible and I actually finished in three-and-a-half years. And when I was done and had finished all the credits to get my diploma, I left home when I was 17.

“My family situation was really difficult. We were an immigrant family and my parents had difficulty adjusting to the American culture. I was also the youngest of four girls but my sister who is closest in age—she’s about 2 years older than me—was born mentally retarded and her mental capacity is at the level of a three or four year old. Even though I’m technically the youngest, I’d end up spending a lot of time taking care of her. I would sit and do flashcards with her to try to teach her the alphabet and numbers.”

For some time, I was just trying to survive out in the world with no real support. I picked up my love for computers again when I was fortunate enough to land at a startup company in San Francisco that was building a network layer called TCP/IP for Windows. This was back when not all computers had networking capability. I landed an admin job (administrative assistant), which was not my dream job at that time, but was something I could easily get, and was good pay for a college student at that time. It re-exposed me to my love for tech, and my love for engineering, and it was good to see the work that they did.

I was also very lucky that there was an IT worker there (named Kate) who allowed me to spend some time with her, helping with her hardware, like swapping out motherboards, adding memory. I loved troubleshooting as well, so the QA team borrowed some of my time, and that was really great. That sort of really invigorated me to say, “Okay. I really need to get my act together and make sure I’m taking the right computer classes in college.” And so I continued down that route. I was in school part time and a lot of courses were very difficult to take at night. Generally, there were very limited classes in terms of the computer science program. Those programs were very, very new back then, so you were lucky if your school had a computer science program. I cobbled together my education as I went. We had a lay off at some point and I ended up in one more admin job. It was there that I was fortunate enough to make a connection with someone who recognized my troubleshooting and technical ability and after the startup was acquired, he recommended I apply for a support role at Lotus which was a subsidiary of IBM at that point. I interviewed and they hired me as a support person. I loved that they had given me that opportunity. It was such a great experience.

“I did very well through most of my academic career, so I had these lofty goals to go to an Ivy League college at some point. I had made it to a top high school in San Francisco (Lowell High and they were rated really, really highly back then). I wished to go somewhere like Harvard for college but because my family life was really difficult, I had to make the decision to just compress my high school education as much as possible and I actually finished in three-and-a-half years. And when I was done and had finished all the credits to get my diploma, I left home when I was 17.”

Pretty early on I ended up coming across this scripting language that was part of the extension framework for what was called LotusScript—it was in a desktop database called Lotus Approach which competed with Microsoft’s Access. No one knew how to use these API’s or the scripting language and I just sort of started playing around with it. I was able to use it to customize different interactions in the app. At some point there was an opportunity that came up for someone who needed to have some web skills and needed to know Lotus Script. The job was unfilled, so I kind of raised my hand and went, “Well, I can do this.” I applied. It was a little unusual for me to do it, because I was only three months in— three or four months into my support role, and for a good reason they want support people to stay in their roles for at least a year before moving on to something else.

They actually made an exception for me, which I was really grateful for, and allowed me to take on this role as an application engineer. That role ended up leading to other opportunities. It was still within the first few months of that role to take on a project to “webify” forms and reports in Approach. “Webifying” and creating dynamic pages was a thing back in the 90’s when most sites were still static. We were trying to take advantage of the new concepts of web forms to bring reports that people wanted to produce dynamically to the web. I worked with the DB2 group. DB2 was IBM’s database server solution. They had an internet connector that they had just built that could be used on the web and so I was able to connect the dots and build a wizard that took your Windows based forms and reports to the web and leveraged that dynamic connector. It was a lot of fun and a lot of hard work, and I did that in three months.

When I demoed it to a really senior engineer at Approach his reaction was, “How did you do that?” because it involved LotusScript, which no one knew; JavaScript, (which no one in our group knew and was an emerging language back then that no one was really an expert in at the time); HTML, which was also fairly new and the DB2 connector which had it’s own scripting, language, and integration. So I just connected those things, and back then there was no specific layout controls in HTML, so I had to build these crazy heuristics for trying to adapt them to the web because there was no X-Y coordinates that you could actually set your elements to. But I approximated it well enough that most forms and reports actually worked out pretty well. That was one of my first projects and I did that mostly solo, so it gave me the confidence that if I could do something like I could do almost anything. And I kept going. Not long after I transferred into main product engineering—doing C and C++ programming—one of my first projects was dealing with the Y2K problem. A lot of people back then started leaving for startups, because startups were the thing to do, so IBM was losing a lot of people in Silicon Valley. Eventually, they decided that they wanted to start doing some consolidation of our group in Lotus. They’d acquired Lotus the year before I’d started there and then they started to consolidate the group that I was in, and so I ended up in a group layoff that they did in order to consolidate things into IBM.  I went from there to a number of different startups where I continued to do development. Recently I went to look up the status of a couple of patent applications I had pending while I was there at IBM and realized that both were granted!

That was with the beginning of my career and I was grateful for the opportunity to continue working as an engineer for awhile. But from all my experiences with engineers, I was almost always the only woman in the group. There was one startup when there were two other women, but that was unusual. Most of the time in teams I was working on, I was the only woman in the group. To be really honest, it didn’t bother me. I didn’t really notice it in a bad way. We would go out for lunch, we would hang out, we would talk tech, etc.

I did a gig at Borland for two-and-a-half years— almost three years —as a pre-sales engineer. I was one of three for their worldwide organization, and I started noticing, “Okay. There are three of us women in sales engineering. That’s kind of interesting.” Again, it didn’t really bother me that much. The three of us still kind of keep in touch. We obviously bonded pretty easily, because we were the only women in any of our sales meetings. Once I earned a top SE award for my district. I was really proud of that because that was also the year I finally finished my college degree after more than 10 years. My sales rep at the time didn’t even know I was studying at night so she was impressed that I was able to kick butt at work and also finish my degree.

“Once I earned a top SE award for my district. I was really proud of that because that was also the year I finally finished my college degree after more than 10 years. My sales rep at the time didn’t even know I was studying at night so she was impressed that I was able to kick butt at work and also finish my degree.”

From Borland I landed at Microsoft, and it was one of those things where I thought, “Wow, an evangelist!” To be an evangelist, travel and speak at conferences, and present about the latest technologies was just an amazing opportunity. There also, for the first year and a half, I didn’t notice anything different. Again, I was one of the very few women in that evangelism organization. It’s probably a thousand people worldwide, at corporate it was about a hundred and fifty people, but only a few women. At the end of my first year, I married, became pregnant, was about to go on maternity leave. I had also moved back from Redmond down to Silicon Valley. They felt that I’d done well enough my very first year at Microsoft that they asked me to stay even though I was going to be remote. We actually had to get approval in order to keep me. It actually escalated all the way to the VP at the time, and he approved it, which was remarkable. Because Microsoft in those days wasn’t very pro remote-employee. I was very lucky that they allowed me to keep my job. Seven of the eight years that I was at Microsoft was remote. I used all the technologies that we had in order to make sure people knew that I was actively engaged, and still driving my initiatives, and I was still networking with the right groups, and getting a lot done in my particular area.

For the first year after I moved, quite a few coworkers had not realized I moved because I was able to create a strong virtual presence. I started noticing that I was being treated a little differently was when I came back from maternity leave. It wasn’t immediate. I had what I felt was a really weird experience of coworkers, partners I was working with, and customers saying, “Wow, you’re pregnant. Congratulations, that’s really great. You’re going to quit your job, right? And stay at home?” I had that over and over again. And I thought, “What? Really, you think I should? I never thought about just being a stay-at-home mom.”

“I started noticing that I was being treated a little differently was when I came back from maternity leave. It wasn’t immediate. I had what I felt was a really weird experience of coworkers, partners I was working with, and customers saying, ‘Wow, you’re pregnant. Congratulations, that’s really great. You’re going to quit your job, right? And stay at home?'”

I’ve had this long career, and suddenly people are saying, “You should stay home” I was getting a lot of peer pressure. I got some from some local moms that I started to meet as I was pregnant, and they were all saying, “Oh, you’re going to quit, right?” And I thought, “Oh…” I just wasn’t expecting that. It was strange to me, and foreign. Not one person ever asked my husband if he was taking time off for our first baby. I was planning on spending some maternity leave off with my young child. I was excited about having my first baby. And I took the 12 paid weeks off that Microsoft offered at that time. I could have taken more through vacation time or other means but I took the 12 weeks. With that first child it seemed to me that 12 weeks would be enough – that was more time than I had ever taken since I had started working when I was 17. In the end though, 12 weeks, for me, wasn’t enough, and I wish that I had taken a little bit longer. As I got back into my role and continuing to do my work, that this term of being “mommy tracked”, I started to feel like, “Wow, that’s actually real.” You’re not being given the opportunities to grow. You’re getting rated really highly for reviews and yet you see the remote colleagues getting the promotions that you’re also asking for. They happen to be male. And I don’t think any of that was intentionally malicious. I think people don’t understand what we know now as unconscious bias.

“As I got back into my role and continuing to do my work, that this term of being ‘mommy tracked,’ I started to feel like, ‘Wow, that’s actually real.’ You’re not being given the opportunities to grow. You’re getting rated really highly for reviews and yet you see the remote colleagues getting the promotions that you’re also asking for. They happen to be male. And I don’t think any of that was intentionally malicious. I think people don’t understand what we know now as unconscious bias.”

We’re doing a lot of training within Atlassian about this now—how to recognize it and what to do about that. That term didn’t exist back then. There was no way of knowing what was going on. I knew that my colleagues and my managers weren’t bad people, but I don’t think they recognized that. They were probably thinking, “She’s busy with her kids now. We can’t give her these responsibilities.” Every year I got great reviews and I was in the top quadrant of very promising and talented employees, yet my career really flatlined after I started having kids. To be clear though, I’m grateful for the time I had at Microsoft. I did get a variety of opportunities where I learned a lot, but I really wish that I could’ve taken my career a little bit farther while I was there.

The issues I experienced were not ones unique to Microsoft – these are issues that exist across our tech industry and we need to recognize it as a broad problem that we need to solve as a community. I did end up leaving Microsoft after eight years. I was ready at that point for bigger challenges. My younger child was in school. She had started kindergarten at that point. I really wanted the next big career opportunity. I went to Intuit for nine months. I was there for a short time in part because developer audience wasn’t a big focus for them at the time and I felt that was still  a big, big part of my career. I was recruited then by a fintech company called Yodlee. There I had the opportunity to exercise many different skills of mine from marketing to engineering, to planning and product management, as well as the evangelism piece.

And there was a really wonderful opportunity of just connecting the dots across many parts of the organization, and really focusing on evangelizing internally. The part of business that I was in wasn’t well understood, especially in our Bangalore office where all of our core engineering and product management was happening. So I spent some time in Bangalore. I actually did three trips in one year to Bangalore, just to really help educate them and to get the alignment that we really needed to be successful with that business. I’m really proud of that work.

I had a challenging project when I started. The developer portal they had wasn’t a true developer portal. You logged into a walled garden only to have three big PDFs to download as documentation that didn’t give enough guidance to get going on the APIs. It didn’t have online,, searchable documentation. It didn’t have a sandbox experience for you to try out the API, and I was able to get everyone rallied around it across all the different organizations, including the Security Office. So we were able to get a new portal out that actually did provide a sandbox environment, and that really shortened the duration of time for the sales reps to close deals with customers that were trying to evaluate their product. They were able to try it out and assess for themselves if the data they were getting was the kind of data that they needed for their solutions. I’m proud of the work that I did there.

I was recruited by Atlassian where I have been now for the last couple of years. Aside from the fact that I’ve built an evangelism team from the ground up, I think the thing that I’m most proud of is that I took some of the learnings that I had from my days at Microsoft. I was a chair for the Women at Microsoft Silicon Valley organization there – we grew an active community and had regular speakers and meetings. We also launched our first Silicon Valley Women at Microsoft conference at Microsoft while I was in that team. But, there was also this concept of mentoring rings that we ran in Silicon Valley. I thought that was unique to us. I didn’t really find any other information about mentoring rings outside of Microsoft. The idea is that it’s really difficult to find female leaders to be your mentor, because there are so few of them in tech. Yet all of us have something unique to contribute in terms of the skillsets, backgrounds, and the learnings we have through our work experiences.

The concept was born out of the idea that we can learn from each other, so let’s bootstrap ourselves together with these mentoring rings. I was part of the pilot group. Martha Galley, who’s now an exec over at Salesforce, was one of the driving forces behind that. So was Kris Olsen, who is a friend of ours who passed away too early. I think about her often when I’m doing my diversity work. I took that mentoring rings concept to Atlassian, and did the first pilot group over a year ago. Just this week the participants from that group (six of them) basically stepped up to run three new mentoring rings that they’re launching over the next few weeks. I’m so happy and proud that they felt it was such a worthwhile endeavor that we participated in a mentoring ring together, that we all learned from each other, and that we have formed a support network and our work has lasted outside of that. I did a women in tech speaker series too, where I invited different people I knew within the industry to come and talk about diversity challenges, specifically for women in tech. All talks were published on YouTube. This year I’m going to be shaking that up. Internally our volunteer initiative is called Side by Side. That’s our broad diversity initiative to make sure that we’re being inclusive of all groups. We’re going to be recasting my speaker series as Side by Side so we can include a broader pool of diversity topics. That brings us to today.

“There was also this concept of mentoring rings that we ran in Silicon Valley. The idea is that it’s really difficult to find female leaders to be your mentor, because there are so few of them in tech. Yet all of us have something unique to contribute in terms of the skillsets, backgrounds, and the learnings we have through our work experiences.”

When was the moment for you when you realized when you were interested in women’s initiatives? Because obviously it became a huge passion.

Yeah. You know what? For me, it was a “start-stop, start-stop” thing. Because I really wasn’t sure what I was experiencing when I came back from maternity leave, from that first child. There was this group starting out in Silicon Valley at that time within Microsoft just getting together for lunch. I went to one of the lunches so I could feel a little more connected to the local campus, because I didn’t work with anyone on our local campus at all. I only worked with folks in Redmond and our field organizations. So I went and I remember thinking, “Oh my God, they have a bunch of pink balloons. I hate the color pink,” [chuckles]. I went to lunch and they just had a very casual lunch get together. The evangelist in me said, “Well, you know? We should have a speaker series. We should get more people rallied around this. Let’s make this more structured. Get more people to come by inviting a speaker. We can still do the networking thing but why don’t we start getting people to come speak about these different topics.”

Claudia Galvan, who was one of the chairs at the time—she’s gone into a number of other amazing women in tech initiatives, and she’s still very, very active—reacted with, “Well, you should join our board.” I said, “Sure, why not?” I figured it would be a great opportunity to stay more connected. But to be honest, at that time, I just didn’t really identify that much with the issues. It took actually participating on that board for me to hear what was going on with the people on the board and people that would come to our program. I built my empathy around what was going on with other women. I realized, “Oh, well actually, this thing where I’m being told I need to work on my soft skills is because I’m assertive and they’re not used to women being assertive. They want me to be the quiet mommy in the corner. Got it, okay.” Other people are experiencing that.

“I built my empathy around what was going on with other women. I realized, ‘Oh, well actually, this thing where I’m being told I need to work on my soft skills is because I’m assertive and they’re not used to women being assertive. They want me to be the quiet mommy in the corner. Got it, okay.’ Other people are experiencing that.”

It helped me identify and put a label to some of the problems that were going on and realize that, “Oh, it is actually part of this diversity stuff that people are talking about.” It’s an issue, I just didn’t realize that was the experience I was having.  It’s all part of this. When I left Microsoft I was really just focusing on getting my career back on track at Intuit and Yodlee and there were already staffers running initiatives like that. I didn’t feel a compelling reason to be a driver in that area. I was happy to be a participant and supporter. It was at Atlassian where I felt like there wasn’t as much of that support yet and that I needed to help bring that along. I’ve been really happy to be part of the volunteer groups that are starting to embrace some of those changes.

The wonderful thing about Atlassian is our strong values. One of them is “Be the change you seek”. I took that and ran. The mentoring rings that I introduced were also launched in Sydney after our pilot in San Francisco. The leaders there reached out to me about how to run it, what people get out of it, what the ground rules are. They ran a successful one in Sydney. They also still meet up more casually like our group does. I think they’re also considering more mentoring rings. It was amazing that word got out about the mentoring rings experience such that so many people wanted to sign up in San Francisco, we had enough for three rings for this year! I thought it was really neat and I was just so proud of the team just to step up and pay it forward.

Over the years, have you seen the issues women are facing change? Or have they been really constant over time?

That’s a great question. I think a lot of it has been constant over time. I don’t know if you saw—There were some reports the other day about how someone had launched a board list, a suggested list of women to put on the board. It’s great that it’s a recognized problem, but before we wouldn’t have even talked about that because there weren’t enough women at that level of seniority (a decade or two ago) that you could even develop enough of a list. I think, too, what’s sad and remarkable is that in the ’80s we didn’t have such a significant problem with women in tech. We had a problem, but it wasn’t as bad. We’ve dropped the numbers, since the ’80s. So the number of people that are coming in, that pipeline problem, really is significant. I think it used to be in the thirties and now it’s 18% coming out of school going into tech that are women. I think that’s sad. We definitely need to fix that problem, that perception of what life is like as an engineer or being a woman in tech.

“What’s sad and remarkable is that in the ’80s we didn’t have such a significant problem with women in tech. We had a problem, but it wasn’t as bad. We’ve dropped the numbers, since the ’80s. So the number of people that are coming in, that pipeline problem, really is significant. I think it used to be in the thirties and now it’s 18% coming out of school going into tech that are women.”

I get this question sometimes about, “Well, I’m in sales or I’m in marketing here.”—Whether it’s Atlassian or Microsoft or somewhere else—and they ask me, “Do I count as a woman in tech? Absolutely. You’re a woman in the tech sector. You’re affected just as much as anyone else with some of these issues that happen. And you do have that unique factor, even though you’re in sales or marketing, you have to absorb some of the technology language in the products we’re working with. Yeah, absolutely, you are a woman in tech. I think the severity in issues may increase when you are an engineer because there are fewer women in engineering.

The language and behavior of engineering teams can be really, particularly tough, especially in a day and age where, we’re very casual and we’re coming in with hoodies, t-shirts, and jeans. We bring our gaming behavior, our nerf guns, and other things that are okay for the bro club, but not very inclusive of women that come in. And it’s not with any malicious intent. I’ve had really good friends in engineering. A lot of them, obviously, have been male and it’s a problem in education, helping them to build that empathy. It’s not that they don’t— they’re doing anything specifically malicious, in many cases, it’s just helping them to understand that things they do that they don’t recognize exclude someone. It can be harmful for someone’s career.

“The language and behavior of engineering teams can be really, particularly tough, especially in a day and age where, we’re very casual and we’re coming in with hoodies, t-shirts, and jeans. We bring our gaming behavior, our nerf guns, and other things that are okay for the bro club, but not very inclusive of women that come in. And it’s not with any malicious intent. I’ve had really good friends in engineering. A lot of them, obviously, have been male and it’s a problem in education, helping them to build that empathy. It’s not that they don’t— they’re doing anything specifically malicious, in many cases, it’s just helping them to understand that things they do that they don’t recognize exclude someone. It can be harmful for someone’s career.”

What are your thoughts on the state of tech in 2016 and the changes that you’ve seen over time? What is really exciting to you right now? What is frustrating to you right now?

I think in the last year and a half it’s been remarkable to see as much coverage as I’ve seen around the diversity problem. I mean, the volume’s pumped up right now. There are tons of articles. There are new articles almost every day, which is great. So it’s more of that education. What I would love to see more of—and I know a lot of companies are looking at this internally—is how to make actionable positive changes. A lot of that’s turning into “How do we roll out our unconscious bias training and make sure that it sticks?” How do we make that effective and not just have a presentation where we make people aware and then leave them feeling helpless that, “Oh, it’s just  innate— it’s a by-product of the fact that we learn those behaviors from caveman days to survive.”

You stereotype people based on something that has been built into your brain to help make sure that you can identify danger really quickly and run, but we apply that in our daily work life to people in not the best way. I think there’s still a level of pragmatics around how we make sure that we can really make those effective changes.

There are women-specific VCs that are starting to crop up, where the real focus is funding female-led startups, which is great. I think until we see more companies that are actually being led by women, we’re not going to see significant and fast change, because by and large, most tech companies are still being driven by white men. We don’t want to start excluding white men in the conversation, but it’s about making sure that the company that you work for really includes as many diverse groups as possible. It benefits the company. There are all these reports about how the more diverse a company is, the better off the shareholders and the company can be in terms of providing the right tools and products to their customers and getting their share prices up. So there’s massive benefits in doing that, and yet we’re still so slow in making sure that happens, you know. There are still lots of baby steps.

“I think until we see more companies that are actually being led by women, we’re not going to see significant and fast change, because by and large, most tech companies are still being driven by white men. We don’t want to start excluding white men in the conversation, but it’s about making sure that the company that you work for really includes as many diverse groups as possible. It benefits the company.”

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

Because of the way I grew up, I’m really persistent and tenacious with that marathon syndrome of “You’re going to get through it, and survive, and do the best that you can, and you want to be successful.” I sometimes forget and I remind myself. I walk into my home and go, “Wow, this is really my home.” I have a nice, comfortable home in an area where I don’t feel afraid to walk around, and it’s a luxury to be able to do that. I may not have made it here, had I not really been determined in those early days to be successful and pursue my passion in tech and to believe in myself, despite the lack of support that I had back then.

So I continue to use that in terms of solving problems and marathoning through cultural changes or organizational changes that happen. Those changes happen in any tech company you go to. At Microsoft we had re-orgs regularly—you could even experience more than one in a year. You’d get shifted to different teams and in order to survive an environment that can be really dynamic, you need to kind of be open to embracing the change, because that change can provide new opportunities for you. I try to stay optimistic. I’m also very pragmatic about things too, because when you’re a survivor you take things in with a more pragmatic perspective. When I look at these broad problems around diversity, I try to identify the meaningful thing that I can do to help. I don’t want to be the helpless victim. I’ve never wanted to be the helpless victim, so I do what I can to impact change. In the areas where I’ve been able to contribute I’m really happy with that, because I feel I’ve helped to make baby steps forward in my area, which for some people has been big for them. I’m happy with that.

“When I look at these broad problems around diversity, I try to identify the meaningful thing that I can do to help. I don’t want to be the helpless victim. I’ve never wanted to be the helpless victim, so I do what I can to impact change.”

You’ve impacted the lives of many, many women. I feel like that’s more than a baby step for a lot of people. You know?

Yeah, back to what am I disappointed with. The numbers are so sad. I just posted a blog about getting young children engaged and really hooked on programming. My kids are between the ages of five and ten, and they have been playing Minecraft. I started doing research and I realized, “Oh you can do Java programming to create your own mods”. Those are extensions of the game, which I think are too advanced for this age group. So I started poking around and realized, “Oh, there is this custom server that you can run called CanaryMod, and then add a plugin called ScriptCraft that will enable you to do this in Javascript. That’s fantastic. That’s such an accessible language even at this age.

And so I set that up and started playing with the kids, and they showed me how to play, because I didn’t know how to play Minecraft. So they had to show me the basics of the game before I could be productive with them. Then I showed them, “Oh, you want to build a house? Sure. Let me show you how to do that.” Because they can manually make it. It will take them forever. But with programming, you can use Javascript and create a castle instantaneously. You can create another Javascript call and have a dance floor, or a bounce house, a castle, or you can spawn a cow [chuckles]. They just thought it was so cool.

I wanted to make sure that they knew that they could do that, that they were empowered as young girls. I wanted them especially to know that math, science, and programming, are not “boy things”. They should see too that Mommy has done it, and can do it with them so they can do it as well. I recently blogged about this, and I had some of the parents internally say, “Oh, I’m so excited about that blog post. My kid’s are also doing Minecraft. We’re going to try this out!”

I had some friends on Facebook who also in tech share that in their networks. That was great to see. I thought, “well, someone’s going to think this blogpost is lame.” I’ve tried to simplify this to make it accessible for—not just super tech-y parents—but any parent to sit down with their kid, and set this up and try it out. I hope people do more things like that. I know there are a lot of different programs—a lot of content out there—that focuses on teens, older kids, and college students. I think, especially for girls, you have to start a little bit younger to get them really excited about technology. It’s funny how stereotyping happens so, so early. When the girls starting coming home and saying, Oh, yeah, robotic stuff? That’s for boys. I thought, No, that’s not true. So I wanted to really provide a way for them to feel empowered—that technology is totally within their reach, even at this age.

I love that. One more question. What advice would you give folks who’ve experienced struggles similar to yours, who are hoping to get into tech, or stay in tech?

To people trying to get into tech, reach out in your network, see if you can find someone who’s in the tech arena already, who really understands the day-to-day of what it is to be in tech. People have all sorts of notions from Hollywood about what the tech life is, and that’s such a narrow, narrow view. There are just so many amazing opportunities in tech, that I wish kids would come and speak with us more, and ask us, what is it really like? I would love for companies to do more of the “bring your kids, bring your local classroom to work” day, so that more kids can be exposed to what that’s really like, and realize, “Oh, it’s totally accessible. There are women there. There are people that look like me here.” That’s really important.

“To people trying to get into tech, reach out in your network, see if you can find someone who’s in the tech arena already, who really understands the day-to-day of what it is to be in tech. People have all sorts of notions from Hollywood about what the tech life is, and that’s such a narrow, narrow view.”

For women in particular, many aren’t sure that they want to stay, and that worries me too. The drop-out rate for women who are mid-career in tech is something like 56%! 56% is huge. That’s too much. I saw an article a few days ago about a company starting to experiment with basically, interning their mothers back in via a program they are calling “returnship.” It’s a program to get women who have been gone from the field for a while comfortable with coming back. I love that concept because I think there’s some pushback with women coming back if they’ve taken a two, three year break. It makes it really hard for them to come back, where they have to start at a level that it doesn’t make sense for what they’ve done in the past.

The other factor is just fear for the women coming back, “Can I do it, it’s been a couple years or three years, or maybe longer, am I capable?” That slow path back in and that support network, I think, is really huge. I think, too, that there should be an active network within a company, whenever a woman is leaving for maternity leave to support them and let them know, “Hey, take whatever leave that you need, and when you come back, we’re here for you, and here are other mothers that have gone through this, talk to them.”

“For women in particular, many aren’t sure that they want to stay, and that worries me too. The drop-out rate for women who are mid-career in tech is something like 56%! 56% is huge. That’s too much.”

Whenever we’ve had people that have gone on maternity leave, I actively reach out to them and talk about the potential challenges. I also remind them “Hey, you know what, don’t make any rash decisions while you’re pregnant, while you’re on leave because your hormones are still super, super high and you can make some decisions you might regret. Talk to me, reach out to the other moms that are here. I’m happy to help you, let’s talk through anything that you might feel is difficult. When you come back, you’re also going to not have as much sleep as you usually have. It’s going to be a transition so, however I can help you, you let me know.” I think that’s important to be supportive, especially once you’ve gone through it, to just let them know, “There’s a light at the end of the tunnel and you can make it through.”

Well, my early years… I come a from a city that feels pretty much like a small town in North Mexico called Chihuahua. Historically and geographically, it has been pretty isolated and is a bit of a singularity in the sense that the proximity to the border creates a culture that is similar to the American Southwest, but at the same time has a unique feel of Mexico. There’s a lot of pride about being from that area and that pride manifests itself in the observance of traditions, which include the strict definitions Mexico has about the role women are expected to play in society.

I was born there in the 1980s, and I come from a long line of people that have grown, and lived, and stayed there forever. Compared to previous generations, I’m actually one of the rare stories of “people who left town.” My parents have a very Mexican success story: my dad runs his own business and occupies a very masculine role in the family; my mom went to college and finished her master’s degree, but then chose to be a stay-at-home-mom after she had us.

“I was born there in the 1980s, and I come from a long line of people that have grown, and lived, and stayed there forever. Compared to previous generations, I’m actually one of the rare stories of ‘people who left town.'”

From the beginning, things seemed to point that I was going to be another kid that grew up there and was destined to get absorbed by the grind of the area. Outside of family businesses—and because of the proximity to the U.S.—most people there end up working in factory jobs. It’s either being part of an assembly line of some sort or managing manufacturing process and operations.

I went to school and studied electronic engineering, and throughout my studies, the mindset and the way people thought about their job opportunities in the future were like: “Yeah, I’m going to get this awesome job at this huge company’s maquila (manufacturing site) where I can put my skills to work.” That was just something that never felt quite right for me, just as many other aspects of my environment back then didn’t.

So you pursued electronic engineering. Did you have technical inclinations in childhood? What made you interested in that in the first place?

What made me interested in that is that I’ve always had this—I’m drawn into trying to understand how things work. I’m a very analytical person and a perfectionist; this makes me want to understand the excruciating details of how things work and connect. It’s funny, because it applies also to the perception of the self. I always thought it was the norm, but one of my first distinct memories as a child is about troubleshooting myself: being very aware of the things I perceived, the people I saw, and how they interacted with each other and with me.

For me, going into a STEM degree seemed like just an extension of my deep interest in understanding how the world works. Electronics seemed like such a fascinating field too, it was not something that I just learn by observing, I had to study and play with it. So it always occupied a special space in my mind.

“For me, going into a STEM degree seemed like just an extension of my deep interest in understanding how the world works.”

One of the first tangible events that inclined me pursue that degree was my first experience with Internet. I think I was about 12 when we first got Internet in Chihuahua. I remember going to this summer camp where they had like, I don’t know, 50 or 60 kids, and they were showing us “the Internet”. I was fascinated and wanted to know more about how that magical thing worked. Two things interested me. First, you have a piece of hardware—a computer—that creates this space for people to communicate.  Secondly, you also have a bunch of other things that somehow exist inside that space. Obviously, at the time I couldn’t wrap my head around it or make the differentiation between hardware and software, but being able to participate in something that felt much bigger than me made me realize I needed to learn more about it.

You were, from what I read, the only woman in your graduating college class. Was there any push back to you pursuing this field?

Yes. There was always push back and commentary around pursuing engineering. I think this even started a generation before mine. My mom wanted to be an architect and back then—that was around the seventies—my grandfather completely put his foot down and told her, “no, you can’t study that. That’s a man’s profession.” Women that want to get married—because that’s basically what the role of women in society is in Mexico—did not pursue those careers back then.

I remember growing up and seeing that, while my mom enjoyed her life and loved being with us, she also regretted not pursuing the path that she actually wanted to follow. I think she got a chance later in life to put that passion to work when my parents built their own house, but I feel that she always had this regret.

“There was always push back and commentary around pursuing engineering. I think this even started a generation before mine. My mom wanted to be an architect and back then—that was around the seventies—my grandfather completely put his foot down and told her, ‘No, you can’t study that. That’s a man’s profession.’ Women that want to get married—because that’s basically what the role of women in society is in Mexico—did not pursue those careers back then.”

I think that’s one of the reasons why my mom and my dad were pretty supportive of my choices, but I remember being asked, even by people at the university, questions like: “Is this what you really want to do? This is such a rigid and cerebral major. It doesn’t seem to match what you would want out of your life. You have a good track record, why don’t you go to a field that would put your skills to a better use?” Of course the definitions of “my life” and “my skills” were generally constrained by the narrow view of what a woman should want and be capable of.   

I even remember having a very good friend in my class tell me things like, “Well, we’re going to have to name you an honorary man because otherwise we can’t get things done.” Or being told by a male colleague “Well, see this is the thing; I’m not going to be able to treat you like a woman because you’re smarter than what a woman should be. So I will need to make an exception about how we treat each other.”  At the time it seemed oddly flattering, but it was always me, and the rest of women, and then my colleagues.

“I had to deal with others not only discouraging me with best intentions, but also questioning my ability to get things done, and making me feel really alienated.”

My time in college had these interesting factors: I had to deal with others not only discouraging me with best intentions, but also questioning my ability to get things done, and making me feel really alienated. I had the luck that my brother actually pursued the same degree—we’re just one year apart—and he was relentlessly supportive of me and a great help. We took several classes together, and having him there to tell me “I know you, and I know you can do this. You’re great, and nothing else matters. Keep going at it,” was really, really helpful. Him, and having my parents supporting my inclination for pursuing things that were out of the norm, were the two things that fueled me to keep going.

Also, as the only woman in an engineering class, people think that you have to leave behind your femininity. There’s this attitude of, “You can’t be an engineer and dress like a girl. You can’t be an engineer and expect to be taken seriously, if you’re wearing something that’s this color, or if you’re doing your hair in a certain way.”

Dating in college was funny: I would tell people what my degree was, most of them were like, “Why are you studying that? Women don’t study that.”  Or even have guys abruptly end conversations under the basis of “you’re not the type of woman I’m looking for” after finding out what I studied—standing 5’9” didn’t help either :).

“Dating in college was funny: I would tell people what my degree was, most of them were like, ‘Why are you studying that? Women don’t study that.’  Or even have guys abruptly end conversations under the basis of ‘You’re not the type of woman I’m looking for’ after finding out what I studied.”

My goodness. Then you ended up going to grad school in the United States. What was the motivation for moving to the States?

That comes way later. Moving to another country was never in my initial plan, it was something that just became possible as I advanced in my engineering career.

I first interned for a car manufacturer subsidiary, where we designed car cluster systems and quality tests. These systems are basically the panel in your dashboard that tells you whether your engine is okay, you have enough gas, and things like that. Part of it required coding in different languages, and gave me enough experience to then apply for a developer position in a Fortune 500 auto parts retailer as part of their IT operations in Mexico. I was fortunate enough to get a developer role there. It was not really aligned with what I thought I would end up doing with an electronic engineering degree, but it seemed like the right choice to make at the time, since most of my other EE prospects were back in some stage of manufacturing and I wanted to create and understand.

The closest I could get to building stuff was software. It was engineering work and I felt passionate about learning, so I grew into the role regardless of the usual “you’re one of the few women” challenges.

I eventually moved into a leadership position because I had a really good mentor that believed in me and gave me the shot, even if I was still pretty much fresh out of school. When I became a team lead, I started noticing that I wanted to learn more about how to be more effective at both managing projects and people—these were skills I never had developed with my original degree. It took me a long time to crystallize an awareness that there was a gap in my knowledge in those areas; then to actually get to the point where I could execute on it.

So there I was, leading a team of developers about two years and a half before I could even start acting on my pursuit and when I found out that Harvard had online courses that could be used to apply for a full program.

They don’t accept you right away. They require you first take three courses relevant to the program and have certain grades—B+ I think. One of the programs was really aligned with the things I wanted to learn and do.

I was working full time at that moment and you had to pay upfront, so I could not stop working if I wanted to study and I didn’t want to be tied up the terms of a scholarship. I didn’t have a great plan, but I ended up throwing myself into it, like “Well, let’s take this on.”

Completing the first courses at Harvard while working full-time was rough. I had a demanding position that would have me at work at 7 am, back at home around 6 pm—but often still on-call—to watch class and then figure out how to stay awake to work on my assignments.

“Completing the first courses at Harvard while working full-time was rough. I had a demanding position that would have me at work at 7 am, back at home around 6 pm—but often still on-call—to watch class and then figure out how to stay awake to work on my assignments.”

Certain classes would also require me to “be there,” and with the time difference this meant waking up even earlier and VCing into a class, only to cram a full day of work afterwards. I had very little spare time and most of my paycheck was actually either funding current classes or going into a savings account for whatever I had to do next. I knew I really wanted to do this, but I had no clue how I was going to make it happen. I could only keep going.

So I finished the courses I needed to get accepted into the program and had saved enough money to move over to Cambridge and find a job over there. I could not afford to just be a full time student and the student visa process could take another year or more. I was already running low on an empty tank after two years of the numerous personal, professional, and health tradeoffs I had to make to get to this point. Waiting more wasn’t in the realm of possibilities if I wanted to finish.

I quit my good paying job and moved in time for summer school and looked for work for a few months. I finally found a contractor job as a developer that left me in an interesting immigration and financial situation.  I could only take projects the staffing company approved, but unfortunately the region hit a bad economic time, and most of the jobs that we were expecting to find were not there anymore.

The situation was pretty precarious, without projects I didn’t have an income, but I still had to figure out my school and living expenses. I couldn’t take any other jobs under the risk of deportation, and I also spent a good chunk of my non-school time looking for projects and taking dead-end interviews that didn’t pan out and turn into real opportunities. My family helped, but they could only do so much with the distance and the currency exchange. It was a really interesting time in my life. I not only got to experience the challenges of being alone in a completely new place and working on my degree, but I also became very sensitive and aware of what it means to be an immigrant in this country; the adversities people need to overcome even if they have the best intentions and all the qualifications to pitch into a community.

“I not only got to experience the challenges of being alone in a completely new place and working on my degree, but I also became very sensitive and aware of what it means to be an immigrant in this country; the adversities people need to overcome even if they have the best intentions and all the qualifications to pitch into a community.”

Yeah. Tell me more about what it was like—being at Harvard, working full time, being an immigrant in a new country—did you know anyone else like you at all?

Not too many people. And that was actually really hard on me. While in Mexico, I could rely on my family and had constant and reliable support from them. This proximity evaporated the moment I moved to the U.S. This change, combined with all the job and immigration challenges, caused me to gradually lose my self-confidence and my belief that I could get things done.

People in privileged situations tend to optimize for the things that will give them the highest returns, including the relationships they engage in. At the time, I was not looking very hot in those people’s book, so it was hard to both make connections and friends who were truly interested in being part of my life. It also didn’t help that everyone was incredibly busy; people had jobs, many goals, and tended to be in networking-all-the-time mode.

There were a couple of organizations that I reached out to, and that started incorporating myself with more, but it still felt kind of forced. Maybe I had the wrong expectations about it, but it felt like you had to script your interactions and wear a mask to look appealing—to motivate people enough to start a relationship. That was really tolling and very different to what I was used to in Mexico.

“People in privileged situations tend to optimize for the things that will give them the highest returns, including the relationships they engage in. At the time, I was not looking very hot in those people’s book, so it was hard to both make connections and friends who were truly interested in being part of my life.”

There were a handful of people who became my support network, my boyfriend included. Having them was incredibly important for my sanity, but there was very little they could do to help with the job and immigration woes. For example, during a dry season of contracting projects, one of my professors offered me the opportunity to TA a class. It didn’t pay a lot, but it was a chance to get some money in and I felt really excited. I brought this offer back as a potential project to the company sponsoring my visa, but they declined since it was more expensive for them to have me make a little money than none at all.  Looking back at this makes me wonder what could I have done differently to take on opportunities like this.

So interesting. What happened after your graduated?

I actually ended up not completing my degree in Cambridge. We had a computer science fair in winter. I was showing off a project and had the luck to run into a Dropbox recruiter. We started chatting and he set me up for an interview. I started the interview cycle knowing my savings were pretty much dried up, the project situation hadn’t picked up, and my staying in the country would be difficult—if not impossible—if I couldn’t find a new project or an alternative soon. A few months without projects meant no visa sponsorship, which would result in dropping my studies and going back home to scramble. I was facing a harsh reality: I had a narrow chance of finishing my degree, after about a year of doing everything in my power to try to make things work.

I went through the interview cycle with Dropbox knowing I liked the company and I HAD to figure things out. The team was great and I knew I wanted to be part of it. Fortunately they liked me too and made me an offer, right after my other contract and visa fell through and I had a few days left to pack my stuff and go back home.

This offer allowed me to stay, but I still had to finish school. Dropbox agreed to give me a few months to wrap up most of the coursework back in Cambridge, while I negotiated with my career adviser to take the remaining classes from California.

I came to the point where I grabbed the few things I had and asked my boyfriend—who is German and had his own immigration woes—if he wanted to come with me to the other side of the country. He said yes, and we moved to California to start what would be my first year working full-time at Dropbox, finishing the remaining coursework, and finding time for a project I had started in the fall with some summer school folks.

“I would often wake up at 5 am to have meetings with my partners in Europe, go to work, come back, code for an hour, and then work on my assignments until I couldn’t keep my eyes open. Six months of trying to do these three things was enough to put me in my place: I fainted at work, ended up having pneumonia, and was completely immobile for three weeks.”

That’s a little bit of a parenthesis worth going into. That same year, I started working on a small tech venture with a few people I met in summer school. Most were part of an international program and were back in Europe when we started working on this knowledge management social network. At a high level, this project was looking to solve issues around reputable and peer-reviewed sources for academic research and how you get specialists to connect with the industry. It’s a hard problem to solve and I worked on this in between failed interviews and class assignments, because it was motivating and interesting.

When all other things started to go south, the project had kept me from feeling like a complete failure, so it was only natural that I decided to continue to work on it while I ramped up at Dropbox and worked on my few last courses remotely.  

This wasn’t cheap: I would often wake up at 5 am to have meetings with my partners in Europe, go to work, come back, code for an hour, and then work on my assignments until I couldn’t keep my eyes open. Six months of trying to do these three things was enough to put me in my place: I fainted at work, ended up having pneumonia, and was completely immobile for three weeks.

I felt really frustrated and angry because I knew that I had put myself in that situation and jeopardized my well-being; at the same time it was really hard to decide between this moonshot I had contributed to create from scratch and the ability to build a stable future with my partner in this country. I wanted to be and belong somewhere again, so I chose the latter.

Having to let go of that project will forever linger as a “what-if” that I may come to regret. However, I had to do what was right for getting my health and my work situation normalized, to finish my degree, and to get to the point that I could actually stay in the U.S.

After I moved here it became really apparent was that the opportunities and the things that I could achieve here were eons away from the stuff I imagined in Mexico.  A woman’s place in the US is not as narrow and constrained as it is in the Mexican society and there is a lot of space for creation.  I just had to figure out how to stay.

“After I moved here it became really apparent was that the opportunities and the things that I could achieve here were eons away from the stuff I imagined in Mexico.  A woman’s place in the US is not as narrow and constrained as it is in the Mexican society and there is a lot of space for creation.  I just had to figure out how to stay.”

Walk me through your experience working in Silicon Valley. How has it been for you?

It’s been, for the most part, a great learning experience. I feel very privileged and fortunate to have arrived to a point in my career where I’m finally doing something that I’m really passionate about full-time. I’m currently a Product Manager for the Dropbox desktop platform and the role has the right combination of technical challenge—for my analytical mind—and collaborative work to give me the space to be a positive agent of change. However, I was not immediately hired into this position. I started almost three years ago as a support engineer; getting to where I am today has been journey of its own.

I have to recognize that, while I set the milestones and direction for this adventure, Dropbox has been an incomparable development platform. The organization attracts incredibly talented people who are also really open, which generates a lot of opportunities for mentoring and learning. All the teams I’ve been a part of have demonstrated willingness to support and enable professional growth, overall if you have an idea of where you want to go or have concrete skills you want to obtain.

Tech can be a bit disconcerting for folks coming from other industries, overall when you look at really young companies that are the process of finding their values and character. When I joined I definitely went through an initial cultural shock. Between the famed Whiskey Fridays, where the whole company would party together, and the sometimes hilarious first world problems people would bring up, I felt like an alien in a parallel universe.  

I have to say, getting to spend time with my colleagues in a relaxed setting, allowed me to get to know them better and see there was a ton of substance behind that initial “elite party people” impression. It still took me some time to get over how disconnected from reality one can grow in this dreamlike environment. This is not Dropbox-specific, but probably more of a Bay Area thing. I’d hear people upset about having to deal with scheduling their Exec—a chore & task-doer service—when all I could think was that three months ago, I was making budgeting-fu just to buy groceries and eat more than lentils every day.

“It still took me some time to get over how disconnected from reality one can grow in this dreamlike environment. This is not Dropbox-specific, but probably more of a Bay Area thing. I’d hear people upset about having to deal with scheduling their Exec—a chore & task-doer service—when all I could think was that three months ago, I was making budgeting-fu just to buy groceries and eat more than lentils every day.”

It took me a while to learn to shake off the sense of strangeness. I could never articulate this in a conversation, but on occasions it seemed as if everyone I met had just been incredibly privileged and had never seen any hardships or experienced any setbacks in their life. It was of course a wrong first impression, which was mostly catalyzed by the competitive environment and the way it pushed people in general to be more vocal about their success than their failures.

Overtime, I was able to see all the humanity and the individuals behind those pristine and seemingly homogenous fronts. I believe Dropbox also realized that individuality and diversity is a key success factor, and little by little started dedicating cycles and very conscious efforts to attract and develop people from different backgrounds and mindsets.

“On occasions it seemed as if everyone I met had just been incredibly privileged and had never seen any hardships or experienced any setbacks in their life. It was of course a wrong first impression, which was mostly catalyzed by the competitive environment and the way it pushed people in general to be more vocal about their success than their failures.”

It was not only a “let’s change our interview and hiring strategies” kind of thing, it has been process where existing employees get involved in improving all aspects of the company and are asked to bring in ideas for the collective benefit. To me this is a huge leap and goes beyond the amount of change certain industries would be willing to challenge themselves to execute. I guess you can say that while tech can come across as immature, it is also pretty quick to identify issues, think through solutions, implement them (as imperfect as they might be), observe, and self-correct.

Yeah. Where have you found your support networks since you moved here?

My boyfriend has been my everlasting partner in crime, advisor, and even the driver of some healthy competition.  I’ve also kept close ties with my family, despite the distance. However, this time around I made it a point to find meaningful friendships and forge fulfilling professional relationships. Luckily, Dropbox is a great place to meet amazing people.

In a way, I think a lot of my friends ended up choosing me first, before I even knew we could be friends.  Some of us gravitated together because we were expats or were completely overwhelmed by the stark differences between where we came from and San Francisco. This immediate empathy and understanding that comes from knowing you don’t have to explain all your thoughts, instead you can go through an experience together, and give each other the courage to keep moving and making your voice be heard in this enormous jungle.  

Knowing other people cared, even if they were not close friends, also helped a lot. It’s funny how you don’t have to even know a person to show that you care and make a difference in their life. If I have to be honest, soon after I moved, I still had this insecurity that held me back from reaching out or forging relationships with people because of past experiences. I was a very introverted and withdrawn person for about a year before I could get over myself and open to people again. I have to thank those few folks that cared, and those who didn’t give up on me and became my friends. Those people who opened their houses and just asked me random questions about who I was and didn’t realize they were helping me get back on my feet again.

I’ve also had great mentors and teammates. My previous manager was a big influence and a great professional support. A lot of things didn’t immediately work to get where I wanted to go, but she was incredibly encouraging and didn’t let me cave in, even if this pursuit meant leaving her team.  Similarly, my current manager, went beyond anything our previous work relationship required, and was the architect for some of the opportunities that allowed me to prove myself and build the skills needed for my current role.

“Soon after I moved, I still had this insecurity that held me back from reaching out or forging relationships with people because of past experiences. I was a very introverted and withdrawn person for about a year before I could get over myself and open to people again. I have to thank those few folks that cared, and those who didn’t give up on me and became my friends. Those people who opened their houses and just asked me random questions about who I was and didn’t realize they were helping me get back on my feet again.”

That’s great. I would love to hear your thoughts on Silicon Valley versus the tech scene in Latin America. What is similar and what is different?

Oh god! First of all, I think that something that Latin America is constantly limiting itself to what other countries are doing in terms of innovation. Mexico in particular, is also very constrained by outdated regulations and ancient cultural paradigms. As a country, Mexico operates in an extremely hierarchical fashion, and in my experience, this is contrary to what you want in an environment when you want fast innovation like a start-up.

Innovation requires a collective and targeted effort, a group people pushing forward new ideas and solving problems to achieve a common goal. It doesn’t matter who comes up with the solution as long as there’s movement and breakthroughs that either move you closer to your objective or prove that it’s not worth pursuing. In Mexico this is mostly inconceivable, company culture stems from the concept of El Jefe, the boss, who is this almost epic figure who is both the CEO and looks at the big picture, but also needs to make all the calls and solve every other problem.  This is not only problematic because El Jefe rarely ends up being so epic, but it also disempower individuals and very few people get to experience a truly collaborative and semi-democratic environment. Mexican companies have a lot of problems to move forward if they don’t find a way to properly manage this.

Funding is also a huge issue. There is not that much capital laying around, and most people who have it not want to risk in technology bets, they prefer going for re-appropriating concepts proven elsewhere, or flat out projects that would further a political or social position. Mexico favors homogeneous and understood situations, being an exception or different can be a stigma more than a competitive advantage. This is a huge deterrent for innovators.

It’s a really interesting situation, because Mexico is in a privileged position to solve and understand problems that affect markets that Silicon Valley can’t wrap its head around, because they don’t exist here. If we, Mexicans, could self-analyze more and emulate less, the country would be in a much better spot.

Being an entrepreneur at scale is not common in Mexico. In general, this is reserved for people who come from money or have political connections.  Most of the new business are mom and pop shops, and even then, people who want to start their own, often need to do it as a side job first to build some capital.

“Mexico favors homogeneous and understood situations, being an exception or different can be a stigma more than a competitive advantage. This is a huge deterrent for innovators. It’s a really interesting situation, because Mexico is in a privileged position to solve and understand problems that affect markets that Silicon Valley can’t wrap its head around, because they don’t exist here. If we, Mexicans, could self-analyze more and emulate less, the country would be in a much better spot.”

How do you feel about the state of Silicon Valley tech in 2016? What is exciting to you? What is frustrating to you?

This will come across as very odd, but I’m intrigued to see how the tech scene matures and deals with economic de-acceleration. The possibility of economic troubles is never exciting, but I think there is a lot of great development and ideation takes place in less plentiful times.  Ideas and societies need to stand the proof of time, so I’m very curious about how things will fare after a bit of healthy natural selection.

Speaking about more positive things, I’m also really interested in seeing the momentum and impact around initiatives to make tech more diverse and to tighten its relationship with communities.  There still are a lot of opportunities to drive positive change.  It sometimes frustrates me to be faced with the sweeping assumption and perception that tech is an evil and selfish industry.  It’s imperfect—as any human endeavor—but there is definitely a lot of willingness and talent that is being used towards the common good.

“I’m intrigued to see how the tech scene matures and deals with economic de-acceleration. The possibility of economic troubles is never exciting, but I think there is a lot of great development and ideation takes place in less plentiful times.  Ideas and societies need to stand the proof of time, so I’m very curious about how things will fare after a bit of healthy natural selection.”

Yeah. How do you think the combination of your background and life experiences impact the way that you approach your work?

My life experiences have definitely made me overly aware other people’s feelings. I ended up developing a keen sense of empathy that I sometimes have to manage. It’s funny because, it can be overwhelming at times and I end up burying myself in technical or analytical tasks to balance it out. I rarely externalize this though!

My background is a obviously helpful and aligned with the things I want to accomplish nowadays. Having seen so many worse case scenarios, allows me to see things others tend to overlook and play devil’s advocate. You know that one important thing you forgot to do in that really important project? It’s most likely one of the things I’m thinking about right now. In a way I tend to take the posture of the forgotten because I have experienced it first hand many times. I think that’s one of the biggest values that I bring in both my role, and my daily interactions with people. My ability to understand, not only how people do something, but also their motivations, and to analyze a given situation and break it into smaller digestible chunks that can be looked at from various perspectives.

How do you think tech could do a better job of integrating different backgrounds and viewpoints into their product?

To begin, I think it’s really important for tech companies to validate their products outside Silicon Valley. Doing user studies people from different regions and occupations to figure out if what we’re building is actually valuable across the board. Getting users in the Bay Area can be pretty much of a self-fulfilling prophecy. The time designing a product has a good understanding of technology, and they validate products with people who live in an area where technology is prevalent and have expectations that are quite aligned with the ideas companies are producing. If it’s not done carefully, these exercises can be the equivalent of asking yourself if you like what you just did. A diverse set of users and opinions can immediately and positively impact the way we develop and think about products.

You can take that a step further by bringing people from different backgrounds into companies, which is a really hard problem to solve.  There are some historical and cultural components to the current makeup of the tech workforce. You can think about this situation in two time dimensions: today, we need to make sure people from different backgrounds and with the right skills have the opportunity to join tech; longer term, we need to make sure we increase the pool of people with skills and make these more attainable and accessible.

I’m personally particularly interested in the future investments we can do to improve this situation. How tech companies can partner with academia, government, and other institutions to make sure STEM education and critical thinking skills become part of the norm for future generations.  This is key, not only to make tech more diverse, but also to prepare for what humankind will face in the next 30 years in terms of AI developments.  

It is entirely possible that the job market as we have it today will cease to exist due to increased automation and technification. It is crucial that we think how we can empower future generations to thrive in this abysmally different context. Think about the impact a very specific type of technology will have, self-driving cars, for example, can turn around the enormous transportation industry and displace a number of direct and indirect jobs.  

Tech is in this privileged position to both further products and experiences, but also to see these type of potential social and human crisis before they happen.  We should think about products, yes, but also about how we can contribute to create a sustainable future and human development opportunities for the coming generations. How can we help schools to create curriculums that prepare people not for the jobs we had 30 years ago but for the jobs that will exist in 30 years?

Where do you see yourself in five or ten years?

I couldn’t well you where in the world I’ll be.  Hopefully around here, the weather is really nice!

Professionally, I would love to take the curiosity I had to put on hold, and start my own company. That little worm is still in the back of my mind. I would love to work in a project that challenges on my ability to look at problems from a fresh perspective, and also allows me to do something that’s humanly impactful.

My daily work is pretty satisfying, but creating something that can result in a perceivable improvement to human problems I care deeply about, would be beyond amazing. I feel really proud about the technical and design feats behind the experiences a product like Dropbox delivers; how seemingly small changes can make people more productive and happy. However, the learning and knowledge space is still something that profoundly resonates with me, and I would love to explore ideas in the boundary where information becomes actionable-knowledge.  I honestly don’t spend a lot of time thinking about specifics, because I know that once I start something my brain gets in this override mode and other things become secondary. It’s not time yet, but it’s definitely in the horizon. 

My last question for you would be based on all the things that you’ve learned, what advice would you give folks from similar backgrounds to you that are hoping to get into tech?

Don’t let anyone define or put a limit to what you can do. Not even yourself.  A lot of the times the issues that hold us back, are only the manifestation of our own insecurities and how much weight we give to people’s opinions in our lives.  My 20 year old self had no way of knowing I could come to where I am. That reality didn’t exist, I had no precedents or role models. All I had was a world of questions, some incomplete notion of self-worth, and a lot of tenacity. I let the questions and the curiosity lead me, instead of letting what I or others thought I could do, define me.

Many of those questions led to dead-ends and failures, but also taught me something. My questions grew bigger and my answers started coming faster. The only costs were to keep trying and not giving up.

If you want to get in tech, just do that, try. As painful—as bad as it can be, you will learn from doing. You will not accomplish anything by staying static waiting for your shot to come. Always be doing and always be open to changing the way you think about yourself and the problems around you. Most skills are a matter of time and patience, but the ability to analyze, self-correct, and motivate yourself will always be crucial to grow, regardless of the end goal.

“Don’t let anyone define or put a limit to what you can do. Not even yourself.  A lot of the times the issues that hold us back, are only the manifestation of our own insecurities and how much weight we give to people’s opinions in our lives.  My 20 year old self had no way of knowing I could come to where I am. That reality didn’t exist, I had no precedents or role models. All I had was a world of questions, some incomplete notion of self-worth, and a lot of tenacity. I let the questions and the curiosity lead me, instead of letting what I or others thought I could do, define me.”

Definitely! So I was born in Central Mexico to my parents and I am one of four children. And when I was around 8, my mother was diagnosed with cancer. So, she came to the United States to get treatment. She was also a migrant farm worker under amnesty;  it was a double blessing in disguise for her to be here. AA couple years later, we came as well. Because she was a permanent resident, she didn’t have the legal leverage to bring us legally even though we were her children. We came undocumented. Eventually, my mom, Mina, became a citizen and we thus became legal residents in the process. When I say here, I mean Redwood City, which is right, smack in the middle of Silicon Valley.

I don’t talk to many people who work in tech and who have grown up here poor. I think I just tweeted something around why people of low income backgrounds find it harder for to succeed in Silicon Valley. Yes, I grew up here,  I see have seen the changes, in the past decade or so. Yeah, I really loved growing up the Bay area. I call myself a Mexican-born, California-bred person. I don’t like the cold.

How did you first get interested in tech?

In high school, I took a computer science class. This was late 1990’s. The computer science class was really amazing. I was doing well. I was surprised. I took it just to say, “We’ll see, let me take this AP Computer Science class”. It ended up being that I really liked programming. I got a scholarship by a local engineering firm – Raychem to attend Berkeley.  The summer before my freshman year, I had my first internship in tech at Hewlett-Packard – at the age of 17.

I took an intro to computer science class but there wasn’t a lot of diversity. When I decided to change majors, my college advisor really didn’t push me to stay in engineering. But I wasn’t doing poorly and I wasn’t doing great, but I think about if I hadn’t stopped engineering, I would have been in a different path. Either way, my path came back to tech because my family lives in Silicon Valley. I went to grad school and I came back to the Bay Area and got a job in tech. It seems that everything was pushing me to be in tech. [laughter] I didn’t like that.

So tell me more about what it was like growing up in the heart of Silicon Valley as a low-income, undocumented immigrant family. It’s a contrast from a lot of folks who grow up in the middle of this.

It’s funny because I met someone that grew up in the peninsula and this person asked me where I grew up. Their second question was  “Are your parents venture capitalists?” [chuckles]. Which is so funny my parents being venture capital, my mom’s a single mom, my dad is still in Mexico. The contrast of what people think that my background is and and what the reality truly is.

I live in Redwood City, which is now the headquarters to Box and Evernote and bunch of other tech companies. When I was growing up, Redwood City was a very different place, it was predominantly Mexican. I remember one time—I worked at Stanford and I when someone asked me where I lived, they responded “That’s where all the nannies and gardeners live!”

A very drastic difference between the affluent Palo Alto and Redwood City. Palo Altowas home had a lot of traditional Silicon Valley – the Hewlett Packards of the world, the IBM’s, etcetera.

Basically, back then, it  was a different Redwood City that exists now.

For me, I worked in Palo Alto in high school but living in a one-bedroom apartment with my whole family. My whole family lived in a one-bedroom and there were six of us. Then my parents divorced.  We were then five; there were four children and my mom.

How’s the rest of your family doing?

Good, good. You know, my mom is amazing. She is one fierce woman. She has bought and maintains her own four-bedroom house. She is my inspiration, I love her. I have three healthy siblings, two beautiful little nieces. Our family is happy and stable—I think it’s because of my mother.

My mother was the cornerstone and she is a thousand more amazing—more times amazing than any other woman out there that I know. Yeah, she’s doing great. I tried to stop by the other day to see her but she wasn’t there I was just too tired and I went home. I live a block away from her so that was easy…

Okay, so let’s get into your work. You’ve had a really amazing career trajectory, like you’ve worked on very challenging projects for a lot of amazing companies. So tell me a bit about that.

I feel like every one of my accomplishments and “successes” that has been published or spoken of, there are hundreds times where I didn’t know what I was doing.

I lacked confidence early on. Then when I started at Twitter, I knew the power of Twitter, but I just didn’t know the impact of Twitter on my life. I look back and it was seven years ago – I can’t believe it!  I just really loved and continue to love, the product. Twitter was where my career and my passion for languages came together.

I came here when I was 10, I learned English within a year. I’m still friends with my teacher that taught me English! Then,  in high school, I learned French. In college I learned Portuguese, so by the time I was like 20, I had already learned three languages in less than ten years.

I love languages and I think that both having to work at all these tech companies, it kind of brings together my love for languages with technology, which I tell kids that technology will be one with their passion – you know, you want to be a zoologist, you want to be a doctor, you want to be a lawyer. All of these things will merge with technology because you’ll need to technology to work in these professions.

I think that at Twitter, it was great having been part of the international team where my passion made an impact.

After I left. In 2013, I wrote a blog post about diversity in tech before all the numbers came out, before there was a lot of PR around it. When 2014 came around a lot of the diversity numbers came out, and they were abysmal as it relates to race and gender. But race and gender numbers came out, and everybody was shocked.

But to me, it wasn’t a shock because I’ve been in this industry forever.

Then I was asked to be on numerous panels.

This one great panel, organized by USA Today, they wanted an entrepreneur that could be on a panel with the Reverend Jesse Jackson. They asked me, the heads of diversity from Facebook, Google, a Stanford law professor, and the reverend.

The whole time, the conversations focused on implicit biases and unconscious biases. There was a lack of accountability. Everybody was talking about recruiting at this campus or going to Grace Hopper as a way to “fix” the issue.

I thought to myself – that none of these program scaled. I thought to myself, “Well, why can’t we use technology to tackle and understand this issue.” That is how Atipica was born.

I wanted to understand the pipeline and the recruiting funnel. Diverse applicants don’t have the networks where their resume gets pushed to the front of the line.  Therefore, their resume usually gets lost in the shuffle, part of the 75% of their resumes are never seen by the human eye. There might be biases if they look at it. Diverse applicants don’t assess themselves well. For example, I have applied for the wrong job, and  technology should have rerouted me to the right job. That’s what I’ve working on.

The influence a name has on a resume. I often wonder, what is happening? How many diverse applicants are getting to their first interview or screening or whatever because of their name? At Atipica, we surface the applicants and interrupt biases – we don’t show names. In our product, we show just initials. We don’t show schools. We have worked a lot to interrupt pattern matching that occurs here in Silicon Valley, so that people can look beyond their implicit biases.

Related to that, I’m curious to know, in your personal experience obviously you’ve had experiences that feed into the work that you do now. I’m curious to know of any sort of personal struggles that you’ve had, going into the industry, as someone from a different background, or someone who was potentially looked over for a job. Have you struggled in that way, yourself?

Yeah, so, I’ve had people tell me that because I am Latina, I shouldn’t wear dresses, inherently just because of my background. Me wearing a dress makes it seem more sexy than, let’s say, a non-Latina wearing a dress.

Who would tell you that??

Human resources.

Wow.

There’s  a picture on the internet of me wearing a dress next to an ambassador, and it wasn’t like a short dress, it was a long dress, and it wasn’t tight, it was just like a nice, professional dress. But either way, I was oversexualized because I am Latina.

Diversity and inclusion comes in two parts – there’s diversity and there’s inclusion. In early stage startups, the environments may not be very diverse – but can be inclusive. At Twitter, I felt the leaders were very inclusive and my colleagues were as well.

Generally, as a Latina woman, I don’t just hit the glass ceiling, I  also hit the glass door and the glass wall because—if I lean in, people are going to think I’m feisty and stuffI don’t have the ability to do other things that other non-POC women might do.

I’ve witnessed a lot of uncomfortable situations coming from people in power and especially the lack of recognition by people that are in a privileged position. I have been in horribly uncomfortable situations that are illegal. Unfortunately, years ago, I decided which battles to pick and none of them were big enough to “burn” bridges. The situation is different now and I admire those women who are holding the industry accountable for their sexism and harassment.

I mentor other women and I advice them to stand up without alienating people – because I had to learn the hard way. When I mentored other women I said, “I’m going to tell you everything that happened to me so you do not do the same and maybe I can show you how to tackle this injustice.” There is one woman that was a friend of mine. She was on maternity leave from a tech company and they stopped vesting her shares during maternity leave.

Really?

Yeah. Oh my God. I guided her and told her to stay lit bit; she ended there for another couple years. She recently left for a better position at another startup. She negotiated that too.

There a lot of lessons I learned the hard way. It’s been years now since a lot of these things happened to me. Early in my career, it was really, really hard working in tech.

I have let go and I’m hopeful something came out of it – for the new generation of young girls joining this industry.

That being said, being an entrepreneur is another whole different story. It’s not this “death by a thousand papercuts” as much as it was working for tech five years ago [laughter]. Entrepreneurship, at least, is very transparent. They either invest in you or not. They may have their biases, they may not, blah blah. But there are hundreds of investors, if not thousands. Whereas, working for a tech company right now is, there are two paths – you stay there or not.  So if there is something that’s not right, what are the paths you can take? As an entrepreneur, you have many numerous paths to take if that were to happen.

Did you have mentors at any point in your career or did you just forged your own path?

I remember a very high profile woman I worked with. She recommended that I get a mentor, and I thought. A mentor is someone you convince to be your professional friend and rely on them. But as I saw great leaders, I understood the importance of mentors. The first Twitter employee, Crystal, did a lot to help me grow professionally.I always say that she was sort of like an unofficial mentor of mine.

As an entrepreneur, I now realize now that mentors that come in different packages, male, female. There’s people that are on the venture front, there’s peer mentors that are entrepreneurs, there’s my female mentors that have much more experiences like mine. Mentorship doesn’t have to be this consistent thing, it just has to a reality. For example, I know a VC –  I can email him anything and he will respond within half a day, and be like, “What do you need,” etc. I consider him a mentor, but he might not think himself as one, and I consider my friend a peer mentor—she’s a female entrepreneur who has raised capital. I think it’s never too late to find  “mentors” in your support circle.

I’m curious to know your biggest motivators that got you through everything.

My motivators are my family and my close friends who answer my text when I’m going through through the valley of despair.”Which all entrepreneurs go through. It’s like, ”What the heck am I doing? will anything ever look up?”

But my biggest motivators are  young people that email me or come up to me after a talk. I try to do more speaking engagements to young people than I do to adults. I have gotten these amazing messages from young people that either saw my stories or read something about me.

One of them is actually my mentee now. He read something on USA Today and now he is part of my life. Even when I am doubting myself, these young people believe in me. A few years ago, I traveled a lot and spoke to youth in Latin America. They were so taken back by my experience ”Whoa. You know you’re a Latina over there…” It is the youth, the next generation of game changers that are my motivators. Because, when they get to be my age, they can see themselves represented in this industry.

I often tell young, Latino youth that tech is creating this immense amount of wealth. Right now Mark Zuckerberg is the sixth richest man.

Tech is creating immense amounts of wealth, but  it’s not creating wealth for our communities and it’s definitely not creating wealth for our future generations. We need to be successful, create that wealth so that we can give back. In sum, I think my biggest motivators have always been the people on the outside that see themselves in me. I think that has always been my drive —even when I get sad, I read the emails these young kids have sent me, and it motivates me to get back up.

We touched on this a little bit earlier the kind of 2009 versus 2016, but how do you feel about the state of the industry in 2016—what are you really excited about, and what would you really like to see change?

I think the industry are having tough conversations with themselves. They need to see the monster they created and talk to see how they can move forward. There are going to be uncomfortable situations. We are facing this accountability crisis. People think, we should call others out, you know, on social media….we should like, blast them!

I’m like, “I’m not sure that’s the most productive way” but if that’s the way you want to handle a lot of the discussions, then go for it. At least we are having the tough conversations – regardless of the medium – then the healing will begin.

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

I’d love to have a restaurant, I love to cook. [laughter] I’ll have a restaurant in Silicon Valley. I think so, and I’m hoping that I have built a company that is inclusive, diverse—I think Biz Stone, who is the co-founder of Twitter always said, “Twitter was not the triumph of technology, is was a triumph of humanity.”

Atipica will be the triumph of humanity – but not relying on a sheet of paper to define talent and job compatibility. I’m hoping that people that don’t know how to write a resume will be able to say, “Hey, I can learn.”  

I’m hopeful that a lot of the startups that I advise right now grow to be successful businesses.

‘m hopeful that these numbers don’t stay the same; I’m certainly hopeful that Latinas are represented in a bigger number than we are now, especially  in product and engineering. I do think that this will be slow, as much as I love this industry, it’s an industry that has a long ways to it might not be 5 or 10 years…. it might take another couple generations.

But I’m hopeful by the time my grandchildren are grown, it won’t be something like this. But this is not all; I do think that everyone needs to combine their passion with what they do. I’m hoping that one day I’ll have a Youtube channel where I show my recipes [chuckles] and to continue with my hobbies.

This is my home—Silicon Valley is my home. Tech has been my passion, my career, and I can’t leave it completely. I don’t think that you can ever leave something.

For example I downloaded a meditation app, and it seemed like a good concept, but I didn’t like the UX. Part of my tech eye is always going to be on – how I utilize tech to improve myself, and improve others, improve the industry.

As closing I am curious to know what advice or lessons or just tips and tricks would you give folks from similar backgrounds to you that are hoping to get into tech but may not feel so encouraged.

Open up your networks.  You’re gonna get rejected—I got rejected after Twitter. What do I do next? I thought to myself. Keep asking. Keep asking. That’s the only way- because other people with privilege and access to networks are asking their friends all the time.  Someone from Stanford gets recruited by Facebook or goes to work at Google or someone leaves Google to go work at uber, those networks are going to perpetuate themselves to sameness. For us, we need  to hack the network.

I was born in South Africa. I was born in Soweto, which is a township in the Johannesburg area. And I was born there in the ’80s which was a very tumultuous time to be born there. The height of the armed resistance against Apartheid. My mom went to Soweto to have me from Botswana, which was where she was living with my father. My father was in exile at the time and so he couldn’t come in to South Africa. So the first couple of weeks of my life it was just me, mom and the grandparents. But then ended up going back to Botswana and was there for a little bit. But the circumstances worsened quite precipitously and it got very violent and a number of people were killed in our immediate circle, and my parents decided that we needed to leave, so we came to the United States.

Wow. Where’d you land?

New York City. JFK [chuckles].

What was that like for you?

I don’t know.

You were still tiny?

I was tiny. But it was a rough-and-tumble couple of months there. It was a thousand bucks, and the Hebrew International Aid Society was an organization that took us. They and New York Association for New Americans had been taking refuges obviously for quite some time, and they were just great to us. They saved us. We lived in the Latham Hotel, which was a homeless shelter. We were on food stamps, and jobless and penniless, and all that. My mom ended up getting a job as an ESL teacher at Fashion Institute of Technology, and my dad got a job as a cashier and coat checker at the Museum of Natural History. That was actually 30 years ago. 30 years ago in April is when we landed. Then my dad eventually became a teacher at a public school in Queens. And my mom became a permanent substitute at an elementary school. They were both teachers, and we eventually got an apartment in south Bronx near Jerome Avenue. You could hear Yankee stadium. Dad didn’t know what a baseball was, but he loved cricket, so we ultimately ended up going to some baseball games. We even saw the Yankees coming out of the stadium once, when  after a game and my dad met Reggie Jackson was the Yankee at the time. He ended up getting the tickets, so he’s a lifelong very big Yankees fan.

What was it like being raised in New York but in a family that’s not from New York or not from America?

That’s a good question, but it makes me realize I should tell more of the story. My parents were both trained as educators and they’ve been teachers in Botswana and in South Africa with my mom. They ultimately had heard from a fellow teacher at Maru-A-Pula in Botswana about a school called Milton Academy in Boston. My dad was doing some research and he ended up applying for a job at a school called Phillips Academy in Andover, Massachusetts. We drove up together, the whole family. They offered him the job, and we made the move. So I grow up in Andover, on an idyllic tree lined, prep-school campus as the son of a chemistry teacher.

Wow. That’s a change.

So maybe the question that you haven’t asked that is the interesting one to answer is, What’s it like going to and growing up on a fancy prep school campus while being eminently unfancy?

Yes.

I don’t know what it would be like not doing that. So I can’t really answer the counterfactual to it. But it was really wonderful. I learned English in preschool and I had learned Spanish in New York. Spanish was actually my first language. And then Xhosa, which is my sort of family language, was my second language. So I was speaking this very odd mix of the three when I got to preschool. The teachers were like, “Wow, it sounds like Spanish but he’s clicking.” It was funny. It was wonderful. I was the only black person in my class often. Sometimes there were two. So I learned to translate. I got really used to people wanting to play with my hair. Wanting me to, “Say your last name. Say it again. Say it again. Say it again.” And and I became fluent in the language of suburban affluent white America, but fluent in it knowing that I was never part of it. So I remember there was a moment when I was probably six or seven, where I was thinking about Ronald Reagan, because he had just been President. I had a panic moment because I was like, “Ronald Reagan was President and I don’t think I can be President because I’m black and because I wasn’t born here and because I have a funny name [chuckles].”Two out of those three are no longer thoughts that a six-year-old would have in those circumstances, which is pretty great. I had numbers of moments like that where I was just like, “Wow, I’m really not one of them.” And so it was always a little bit disorientated, especially because my parents being activists and civil rights activists particularly, always instilled in us a very, very strong sense of self and a very acute and intimate sensitivity to racism. So it was something I was always thinking about, and it was ever present. When I got to college and people like, “Oh. You went to Andover?” And it’s like, I’m a lot preppier than you think because I actually grew up on the campus but I’m a lot less preppy than you could ever understand, because of all the other stuff. And so, it’s just weird to be a third rail kid. To have a foot on both sides of the ocean.

Yeah. That’s interesting. What did you think you were going to be when you grew up? And did you have family pointing you in any particular direction?

I thought I was going to be the president until I was six. And then I thought, “You know what? I might still be able to.”

And then, later, I wanted to be a lawyer. And then I wanted to be a diplomat because my—I have diplomats in my family. So, I knew about it—I learned about it early. And they’re like, “Speaking multiple languages helps.” And I went, “Okay. Great.”

When I got to college, however, I wanted to be a chemical engineer. My dad was a chemistry teacher. I was his student in chemistry. I was a very disciplined and conscientious chemistry student. And so, when I—and I even weighed the quality of the chemical engineering as part of the decision matrix for choosing my college. So, I really wanted to be a chemical engineer, or so I thought.

Yeah. When did that turn?

When I hated college passionately.

Me too.

Really? Hooray! I hated college so much. There were a couple of reasons. One thing I always say somewhat jokingly is if you are a drop out of Harvard or Stanford you must be a genius, but if you’re a drop out of a community college you must be emotionally compromised somehow. I was actually just emotionally compromised, not a genius. I hated college because it was very lonely. I was black but not black American in the sense that I didn’t have the shared history and I didn’t grow up in a black American home. I grew up in a black home in a America. So that was a very strange thing that I couldn’t navigate and so finding my people was a little disorienting on that basis. I was preppy but not wealthy. I was African but not Nigerian. That was just from the social side I was very isolated. Academically, I hated engineering and I had gotten about half way through it and then I just stopped. I switched to philosophy, and thought that philosophy would be a very purely intellectually stimulating pursuit, and I was sorely disappointed by that too. I ended up dropping out and it was a pretty shameful dropout, but I remember that—I realized that most of the people who were at school were highly intrinsically motivated self-starters with working parents with graduate degrees and per capita incomes of $250K and greater, and so they needed Stanford degrees. The notion of it being the best school was really that they selected people who were already going to be okay, and I found that also to be really distasteful – like it was such a—it felt like it was finishing school for the already successful, which  got me really depressed.

So, I dropped out.

What happened after that?

We did a startup, naturally. That’s the thing about Stanford. I will say, 2003, four, five, startups were, compared to now, they weren’t on anybody’s radar. But a guy at the business school was working on a project out of this class, Formation of New Ventures, which was taught by a VC and, you know? And he and I crossed paths and he was like, “You should come work for me on this.” And he asked me to do it because I had a lot of Facebook friends and, at that time, that actually meant something [laughter].

And so, and he was working on a product that was oriented towards the demographic that I had the connection to which is the young professional types. And so, I agreed to work for him. And so, I came on as a very early employee and in very short order we raised some capital and I was launched into the tech world.

I’m curious what your impressions were, or maybe even preconceptions of Silicon Valley, and whether or not they lived up to your expectations.

I didn’t have a ton because I was interested in science and engineering, so not really in technology per say. Certainly not in business innovation, and so I didn’t come in with any sort of presumptions particularly. What I will say I was surprised by, and only recently I was stopped being surprised by the fact that it’s a human capital business. It’s a people business and people tend to have insular networks. It’s very much a people business with a lot of instinct and gut and those types of things tied to people. It’s not that accessible surprisingly. I would have thought, and there was a brief period where I did think it was ridiculously accessible. It’s funny because it should be the most accessible place in the world. That is, I think, a preconception that I was disabused of. The other piece is venture is even more intensely that way… Times a thousand

Walk me through the startup chapter of your life when you were in it as an employee.

Oh, boy. I think we accidentally picked up the anti-startup handbook [chuckles]. We were building in PHP. I think we were building in PHP because Facebook was but no other real reason. All of the engineers we knew wanted to build on the Ruby framework or rails framework and we hired a series of executives and we outsourced to Russia non-thoughtfully. We had a hierarchical culture that emerged relatively quickly. We’re dealing with some intense cultural stuff. It was chaotic. It was intensely chaotic. In retrospect we were on the verge of going out of business for six months and I was naive and didn’t quite realize it at the time because it is a momentum thing. When the momentum was good you feel awesome even though you’re spending other people’s money and you’re lighting it on fire, basically. That was intense. The high highs and frequent lows were also a feature in that chapter of startup life. In part because I was also just not in a very good state. It felt like I had failed, in fact. I think it’s safe to say I had failed, in the sense that my parents were deeply disappointed and concerned about my state of being, and my peer group didn’t really understand me, and they thought I was sort of flailing in the wind, and I felt a little bit like I was. And this cult of failure that people celebrate here is  because failure just sucks a lot.

There’s plenty of failure out there. It’s not hard to find. And when people here talk about failure, they’re actually talking about success, and they’re talking about overcoming failure, which is all well and good but celebrating failure is something that is a pet peeve of mine because of having felt like I was fully failed. And we were able to sort of land the plane on the startup and get an outcome for it, and exit the business in a way that we were licking our wounds a bit, but it’s still alive. But it felt like a failure, and these outcomes feel so binary here, where if you’re not on the, “Oh, my god, this is it crushing it” track, you have failed. And that just really hurts. It’s so defeating. It’s so de-motivating. And the piece that I find motivating is not when I’ve failed, but it’s believing that there’s a chance that I can eventually succeed [chuckles]. A promise of success is what’s motivating me. So that period I try not to think about that much, and I’ve managed just like we all have to retroactively tell the story very neatly. Like, “Oh, like 300,000 users and a Series A!” But the truth is the matter is I was just sort of lost and confused, and we were making not excellent decisions with this startup, and I didn’t know my ass from my elbow, and so it’s been clear to me, if I even was value add, even though the founder kept me on—so it was not recommended. People have asked me. It’s like, “Oh, should I drop out of school, because you did?” “Don’t. Please don’t.” It sucks. It’s so lonely, and it’s discouraging and it’s so embarrassing and shameful. Don’t do it, you know? And not enough people, I think, are talking about that, so.

You touched on otherness growing up. Not feeling like you fit in with white kids. Not feeling like you fit in with American black kids. Did you feel that otherness when you worked in startup land?

Oh, yeah. The otherness–if I had to characterize the feeling in one word, it would be poor [laughter]. And I hear people say, “Just boot strap it.” It’s like what does that mean, you know? My credit score got crushed because I wasn’t sophisticated about that and my parents, they didn’t know a ton about that stuff. And so, they hadn’t really given me all the lessons. I didn’t have a nest egg. I didn’t have savings to speak of. I didn’t have aunts and uncles who could float me five, ten K to say nothing of the 50, hundred K’s that people get. And yes, of course, there’s cultural stuff. And there is gas lighting and feelings of invisible racism and other isms that are manifesting in conversations and manifesting in the challenges I encounter when I access certain networks but when the truth—when push comes to shove, not having as much money as everybody else around me was by far the biggest feeling of othering or otherness.

Me too. Yeah. I remember going—and no one knew this but going to all of my friends’ millionaire houses and partying with them and then going home and eating my pocket ramen like every night and being like, “Fuck. Am I the only one in tech living like this?” 

And poverty’s expensive, you know? It kicks you—it has a cognitive toll and a physical toll and it’s really hard to keep pace in a fast-moving environment when you’re also trying to navigate your personal finances. And it’s hard to do that I remember, I said to somebody that I’ve never been to SXSW, because when I was a broke, startup person, whether I was an early employee, or later a founder, I just didn’t have the money to fly there. That’s why I didn’t go. Now it’s like, “I didn’t go, because I’m way too cool for it.” No, I just was poor, and you were not, because your aunt gave you money. People might be surprised by how often people outside of the dominant demographic just don’t have financial access. Just disproportionately, don’t have financial access, and therefore, our risk calculus and the way we navigate this world, and how we spend our time, has to be different, because there’s some stuff we can’t afford to do. Ski week? Fuck off.

Yeah. That tweet storm that went around yesterday, the YC guy, I was looking at the replies, and I saw one guy’s reply just be like, “Did you ever consider not taking funding?” I’m like, what a silly assumption. To assume that it’s possible for him to just bootstrap it. With what money?

Now that I’m on this side of the table, I’m guilty of this too. Come back to us when you have some traction. Why don’t you raise a friends or family or an angel round. a.k.a I assume that you are in your first degree connections, in a world of millionaires. Which is a horrible and stupid assumption, and is incorrect and is wrong.

I make the same assumptions, even as someone who wasn’t a rich person here. I still assume that everybody else is.

There’s also this weird duck syndrome thing too, where we’re part of your credibility and your ability to make moves in this network is fundamentally tied to a money thing. You have to hang and so you have to fake it. There are plenty of people I know, and I was one of these who were furiously paddling under the surface just to cruise. Just to have the right clothes, just to have the right gadgets. I was on a dumb phone for too long because I couldn’t afford a smartphone because my parents weren’t rich. We came here with nothing. In America, where people of color are disproportionately in less wealthy networks, that just means that money is a barrier. Period.

If you want to touch on being a founder, we can do that, but walk me through, from that first experience, to getting into VC. Did you have any idea that that would be the path?

No, I’m on record all over the place, saying I’d never be in a VC. I had a view of VC, that they were just … Also deep down, I felt too poor to ever become a VC, so that was also driving it. I also just had a view of VC as Menlo Park, khakis, Princeton, MBA. I didn’t feel like that was the person I was growing into. Turns out, that’s what VC’s are, which is fine. At some point, I worked for Obama’s campaign. He was my people obviously and I was so drawn to him spiritually and then politically and culturally. That was a defining experience for me, maybe the defining professional experience for me because I remembered that I came from a line of people who were very politically motivated, not in the sense of ambitious in elected office, but who were civil rights activists and from my father to my mom’s father and my father’s grandfather and it’s all an investment in the future — in mine and my generation’s lives. I felt like that was something that was important to me that I had forgotten in the rat race of Churn and MRR and valuations and tech conferences and shit and so it reminded me that the only work that I really felt was worth doing over the very long term had to have some political point of view and had to be positive social results and that stuck with me since and has changed the way I felt about business. And that deepens the more I learn about our economy and my view of capitalism. So that was awesome, like, introducing Michelle Obama on election eve, which was just wild. Then, after working on some startups, I realized that I wanted to repair the relationship with my parents and then went back to school.

At this point, were they super stressed about you?

Yeah, they were used to it, but there was a constant hum of stress that had been following them for years. I knew it, and I could hear it, too, so I had it, too.

What was it like, going back to school?

Best decision of my life. I met my wife. I met my wife, and I also got involved with the d. school, and started really enjoying some of the philosophy work I was doing —actually continued into graduate classes and began a thesis on the theory of intention, which I still find fascinating.  But instead of finishing a Master’s, I ended up dropping out again to join Collaborative Fund. But it was great to be, you know, learning environment, having lived, having done a couple startups, and been in different parts of the world, and been around poverty, and been around extreme wealth, and just seeing stuff, you know?

What have been some of the toughest parts of your work?

Toughest parts of the work. Well, VC is not–being a VC is one of the best jobs in the world so it’s hard to complain about it. I truly love it. And, on some level, it doesn’t feel right to complain about it but if I see fifteen hundred companies in a year I usually make six investments. And so, I’m in the business of saying no. And I’m a dream crusher. That’s my job. And “you are what you repeatedly do”, it’s been said, right? And so I crush dreams. And that is trying. It never gets easier. And because somebody will have such an amazing story. You can just see blood, sweat, and tears all over their product and you can see that they’re just hungry – physically and spiritually – and you have to say, “I don’t like your brand. it’s just so crappy. The hardest part about that, too, at the earliest stage, because there’s no data, is, I can’t say it’s not personal. It’s personal. That’s all it is. It’s not just, really hurt the people. I totally understand it, and some people get really offended, and take it personally, as they rightfully should. Doing that every day, just doesn’t feel good. Having to find a way to do that while also maintaining one’s reputation, because as a VC, your personal belief in your firm’s brand is all you have. If we have to disappoint people all day every day, and still maintain a good reputation, that’s a tough nut to crack. Finding ways to say no to people, such that they’ll say nice things, is a weird thing to have to do every day.

In this project the idea has come up that VCs are interested in investing only in problems that they can relate to. What are your thoughts?

Yeah, well, one of the things that I’ve caught myself doing, and I’m ashamed of, and I don’t do it anymore, or at least I try not to do it anymore is I’ll see a feminine hygeine product, and I’ll think, oh I don’t know anything about that market. But then I’ll see a construction management software, and I’ll think oh, that’s interesting. Which is crazy behavior and is deeply sexist behavior. And probably misogynistic behavior because tied to that is: I don’t want to know anything about X, Y, or Z. And that is dark. And I’ve caught myself doing that. And I’ve caught myself, also, meeting with an entrepreneur from Paducah, Kentucky and, on the basis of that person’s accent, making judgments about their likelihood of being an effective engineer. I’ve caught myself evaluating somebody’s watch or effective—maybe Spanish was their first language and they have slightly darker skin and then discounting the quality of the design of their product. Just stuff like that. And–

Interesting considering Spanish was your first language.

I know, right? Yeah [laughter]. And I am somebody who’s trying my hardest to actively avoid these unconscious biases. And so, Lord help the rest of the industry. And yeah. Lord help the rest of the industry. It’s so tough. And there’s so many companies that, if you are a 26-year-old heterosexual white male living in a city, you are their target customer. And one thing that’s funny about VC is most VCs are old, too, and don’t live in cities. And so, that’s not even their experience.

And I think it’s we invest in people who we recognize. And because ultimately this is a human capital business and the signals are instinct and gut driven and your networks are insular and stuff. So, if somebody uses the right language or communication—body language, physical language, et cetera, and makes you feel like you’re in home space, then, I think, that is a criteria that loosens the strings. And so, I think that means that I, conceivably, have an advantage investing in people of color, and that a woman should have an advantage investing in products that serve half of the population that has been underserved – in theory. In practice it’s hard because—this author Richard Wright talks about this phenomenon called the beast in the skull, where he says that the effect of racism—racism twists the psychology and the consciousness of the racist, and of the receiver of said racism. So I’m as awful as a so-called racist is,and so I don’t trust my instincts sometimes because I’m wracked with my own level of guilt about my own biases, and about stuff that I’ve internalized that I know has been fed to me and I really don’t want, but that I have. I get all twisted up about it myself, and that is tragic. I don’t really know what to do about that.

Let’s come back here for a second. How do you—we touched on this quite a bit, but how do you feel about the state of Tech in 2016? Like what is really exciting to you? What frustrates you?

What’s really exciting to me is the unrelenting optimism. I really do feel like Tech as an industry is a very supportive culture once you’re on the inside of it. And it’s a very collaborative culture and some people are always co-conspirators and stuff. And even though there are—yeah, so there’s that. And then the piece that troubles me a little bit is this thread, or this belief in the hero culture and the cult of the founder and these sycophants, you know? You know, Jobs didn’t change the world alone, obviously. And so it’s scary to think about that because I think of that makes it harder to build, really inclusive and ultimately resilient culture – that hero culture thing. And it’s also not true of the best of tech. The best of tech is very collaborative, and it’s very open to criticism and is constantly adjusting and is swim or die, and so it’s always moving, and the best of tech feels like a hip hop world – you’re only as good as your last hit, and you’re always trying to get on somebody else’s single, and there’s beefs, but you’re all in this together and ultimately you’re trying to lift—you’re trying to push the whole culture forward, and you’re remixing the past and you’re constantly sampling and you know your history and you’re tied to this optimism through generations. And I think these are really wonderful features of this industry and they’re poorly understood by people outside of it, and then a lot of newcomers, which scares me a little bit. I’m cautiously optimistic now.

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

Yes. A VC said something beautiful the day before yesterday. She was talking about feedback cycles and how some are longer and some are shorter. And in VC, the feedback cycle is so long that it looks like a straight line because it just takes forever to—it takes six, seven years to learn because that’s when whatever comes to fruition when you seeded the company. When it’s outcome has started to play out. And so, I don’t even know if I’m good at this yet. I know, now, that I can have a career in it but I don’t know if I’m going to get in it yet. And so, I think I need another three to five years to just know that. So, maybe ask me in three to five years but I suspect I’ll be doing this for 20 years.

My last question for you would be: what advice would you have for people from similar backgrounds who are hoping to get into tech or VC?

Number one would be to save money. Because if you have personal runway then you are structurally more like most of the people who have succeeded. That’s one and that’s not an easy thing to do, but save money. The second would be to try and divide the world of startups, especially in early stage setups, into two functions that constitute a startup. One is building the product. The other one is selling the product. And so figure out if you’re a builder or a seller and don’t be afraid of sales if you are a seller. Choose the one that you have the best chance at. By keeping it simple that way you can maybe orient and organize your activities around one of those two frameworks. Then, the third would be that who you know can be the difference maker, who you know is not whose cellphone and email address you have. It’s who is going to go into bat for you. A lot of people wrongly think that collecting a Rolodex is productive networking, and I think but that’s only 1% of it and I think that probably 60% of it is effective follow-up so I can’t tell you the number of times I’ve said, reach out to me and somebody reaches out. We have a nice first conversation. I don’t hear from them for a while and they reach out asking for something. At that point you’re like asking a stranger for something. What’s that going to do for you? Add value before you extract it. Be thoughtful and followup. Treat people well, meet them where they’re at. Be curious about other’s lives and learn about them. Listen to others and then use that to build your network.

Sure. I was born and raised in Rio de Janeiro, Brazil, born in Copacabana, like the song, which is a real neighborhood in Rio. Moved out of Copacabana to one of the suburbs of downtown Rio, but still within the city and lived there until I was 17. Had a pretty regular middle class upbringing in Rio. My dad is in the military. My mom was self-employed/artist, so she taught painting to middle aged women as kind of like almost like art therapy sort of thing. She always said it was a place for middle aged women to come and chat and kind of air their grievances, and in the meantime create something beautiful and then go home with it.

Amazing.

It was pretty chill. Went to private school, which is what we do in Brazil since the public system’s not very good. Spent most of my time playing soccer, avoiding homework. Eventually started playing music, so that changed a little bit. My teen years I started going more into—stopped playing some of the soccer, did even less homework, and spent most of my time in garages or with people who were into mostly American music in fact, and just making music, having a very typical teenage years until my family moved to the U.S. We can go into that in a minute, because I feel like those are no longer my early years. I want to give you a second to ask any further questions on that, but yeah, it was a pretty nice and safe upbringing, good supportive family, no plans of really living abroad at all. I come from a family of a long standing admirals and people from the Navy, so my father, my father’s father, my uncles were all in the Navy, and there was a little bit of pressure for me to go into that, but I quickly jumped down, wasn’t quite a good fit. Yeah. I can go into more details if you’d like to know more, but I think, yeah, it was a pretty straight forward upbringing, pretty happy one.

You kind of just touched on it, but what did your parents expect you to be or do when you grew up? Was their any family pressure?

Yeah. From my dad’s side. Nothing crazy, but there was definitely a certain level of expectation that I would go into the military. My dad was a one star admiral. My grandfather was a four star admiral, who eventually was the secretary of the Navy for the Brazilian president. I was named after him, so there was definitely some pressure of like following your grandfather’s footsteps, because I was named after him. I was really close to him obviously as well. There was a little bit of pressure there, but—Obviously I considered it. You don’t know, right? You always consider what your parents—or at least, I don’t know, I did. The more I learned about it I figured out that it wasn’t really the life for me, so I jumped out and decided—My mom never really had any expectations.

It was a very interesting household in the sense that my father was always strict, military strict, with nothing crazy, but obviously he liked order, and following directions, and making plans and following them, while my mom was an artist, still is. You can imagine very different ways to decide on priorities, and make decisions, and decide what to do, which is not a surprise that they’ve been divorced twice from each other. They got divorced for a while. They remarried each other, and now they’re divorced again. It’s not a surprise that that’s what happened. My favorite stat is that my dad is on his third marriage, but only second wife. Yeah. From my dad’s side some expectation that I would go in the military. Took some convincing to say that I didn’t want to, but eventually he got it. From my mom’s side not so much. She just wanted me to be happy and figure out what I wanted to do.

Yeah. Did you have any inclinations at the time of what you want to do instead?

I had no idea. I mean, the dream is always to go into music, right? A lot of my friends have in Brazil, which is awesome, super proud of them. I knew that I wasn’t quite good enough to do it, to cut it. I was good enough to hang out, and play, and make music, and have fun with it, nor did I really want to go through the lifestyle. I figured it’s kind of a brutal way to go through life. That was kind of the dream, right? Before that it was I want to be a soccer player. That’s what every single kid in Brazil wants to be. I was kind of good, but not good enough. Then after that I just kind of defaulted, was like, “I don’t know. I’ll work in corporate Brazil. I’ll get a business degree and work for a corporate or company and do something.” There was never a calling or anything like that.

Yeah, so you moved to the states by accident?

I did. I did. It certainly wasn’t my plan. My dad was in the military. He got transferred to Washington D.C. for a couple years. It’s very common. For two years he was essentially a diplomat. He was representing the Brazilian Navy in an American Defense Board where they discussed threats to the American continent. There was an Army, a Navy, and an Air Force guy from every country from Canada to Chile, except for Cuba obviously. Every two years they switched the roster a little bit. My dad got sent out. As I mentioned before I had no plans. It was never a dream of the family to move to America. We have no roots here or nobody in the family ever lived here, but it was an opportunity. It was a cool one, and I was seventeen.

Then that really set off a number of events that changed my life. That was in 2002. I’ve been here now every since. I’m 31, so I’m almost at the point that I’m officially half and half, which will be a strange time whenever that happens. A lot of things happened. We were moving halfway through my senior year of high school in Brazil, which would have been July, 2002. Our academic year is flipped, because our summer break is in December, so It was halfway through my senior year. A lot of families go through this in the military, so we knew that if I left halfway through my senior year, I would have—In the past when that happened they used to send you back a year, so you would get here in July and start junior year of high school. I was like six months away from going to college, and if I didn’t do anything, I would have landed here and been pushed back essentially two years.

What I did was I dropped out of Brazilian high school after my junior year. You’re told my the military like a year in advance like, “This is your next post,” get your affairs in order sort of thing. I dropped out, and I just took the Brazilian GED. Then I had my high school finished, and then I moved here and went to community college. The idea was I will be here for a couple of years. I’ll get an associates, learn English, and go back. That was the plan.

Wow. Walk me through the path you didn’t expect. You went to community college. There were some years in between, and then you ended up in a top five MBA program.

Yeah. Man, that’s a long time. What happened was I landed in D.C. I didn’t speak a lot of English. I spoke English as well as someone coming out of high school, in the US for example, would speak whatever second language they took.

Horribly.

Yeah. Exactly. I was a committed student, but even then I could understand about fifty percent of what people were saying, and I could probably order a burger and kind of get the basic stuff out, but definitely overwhelming. I got here, and I enrolled in community college. I went to Montgomery College, just outside of D.C. where we were living. I got this job, which was totally .. Should I say with whom? Well, we can talk about that later. It was with an ice cream shop and it was totally under the table, because I didn’t have the papers to work, but I was over two years. What are they going to do, kick me out? I’m leaving in two years. Who cares, right? It was something that other Brazilians had done before. It was actually very common that because military families were coming in and out every two years, essentially there would always be opening in these companies, the businesses, that were willing to hire illegal workers anyway. You would come and just kind of fill in for the other high school age person who just moved back to Brazil essentially, so I did that.

Turned out I made really great friends, and they were all American. Most of the people I worked with were American, although there were a couple other Brazilian military kids, but they were mostly American. We became real friends. They were all senior year in high school, and they were all applying to college the next year. A lot of them went to amazing schools like Wash U, Kalamazoo College, Northwestern University, which is where I actually ended up at for a masters degree. I figured out they were my friends and they were like, “Why aren’t you going to college?” I was like, “I don’t know. It was never part of the plan. I’m here for two years.”A year into I figured out a couple things. One is that if I got my associates and I went back to Brazil, none of that would have transferred, so I would have had to start college over again, which would have pushed me back five years. Whenever I literally have to start studying for the tests that are necessary to go to college in Brazil and so forth and so on. I was like, “Well, there’s another option, which is I can transfer here in the US and just study two more years and get a bachelor’s.

With the support of my friends, who were very well versed in the university application process in America, I figure out what I want to do and that I could do it, that I could transfer and I could complete it in two years. I decided that I wanted to do it. I sat my parents down and said, “This is what I want to do.” They looked at me and said, “That’s great, but we can’t help you really. Once we’re going back to Brazil we’re going to make money in reais again, which is the Brazilian currency, and there’s no way we can financially support you if you’re staying in the US for college for two more years.” I was like, “Okay. Well, let me think this through.” I figured out that a lot of universities around the U.S. give scholarships to international students, because they’re in places like Nebraska, or Omaha, or whatever, and they need to attract international students. What I did essentially was I bought a U.S. News college rankings magazine and I essentially called every university on it to ask, “Do you have an international students scholarship?” I figured out a couple that did and some that I was interested in.

I ended up applying to—and then I figured out later in the process—I knew I had to apply by like January 15th to be accepted for the fall, and then I was like, “Oh, there’s this thing you got to do. It’s the SAT.” I was like, “Ah, fuck. I had to study for the SAT in like two weeks, and take it, and get a good enough score to apply and build this whole application portfolio. I’m sure you know about getting your grades in order, get your SAT score, get your recommendation letters, write essays for applications, and all kinds of stuff. I did all of that and ended up applying to a couple of schools. I made some connections before since I called them with the international students affairs deans or whatever, provost, depending on the university. Ended up getting accepted into a small liberal arts school two and a half hours outside of Chicago called Illinois Wesleyan University, who gave me enough of a scholarship, it was about seventy percent, to go there for two more years. It was an easy decision. One of my best friends was going to Wash U. My girlfriend at the time was going to to Northwestern. I had a friend at Kalamazoo College. I was like, well my family’s leaving the East coast, I have no roots in America, so I might as well go close to where my friends are.

I got accepted and went to school for two more years. Graduated in 2006 with a sub par GPA, but in the green nonetheless and got a shitty job out of undergraduate. It was 2006, and I was doing customer service/sales support at Motorola, which even at the time was just after the Razr phase. Even then they were already starting to decline. I was working on the federal practice. It was really boring. Here’s the business that I was in. You know those radios that cops walk around with? That was the business I was supporting. You could not be more boring and stuffy. Anyway, it was a job, and it gave me a visa, and allowed me to stay. Eighteen months into it I was like, “I hate it. I need to get out.” I jumped ship, and I went to a company called Mintel. It’s a market research company, like a global company, and did sales from them. I jumped from customer service/sales support to doing inside sales, sales on the phone.

Then the biggest opportunity of my professional career up until that point happened, which was they had an opening for international sales, like outside sales. I was doing inside sales on the phone for like three months, and then it happened that they had an opening for their Latin American sales rep. Turns out it’s really hard to hire people who speak Portuguese, and Brazil was their biggest market. Although I had no experience in sales really, other than the three months that I had been doing their inside sales, they were like, “Well, we’ll give you a shot.” My job then went from being on the phone and just like repeating scripts to flying between Chicago and Sao Paulo once a month to meet with director of innovation and marketing of like Pepsi Co, which was nuts. I was completely unprepared. I studied business, but it was a liberal arts school. It didn’t matter. My senior year I was taking—What was I taking? Yeah. I was taking women’s literature in Afghanistan. Those were the level of classes I was taking, which was awesome. It was great, but I was not prepared for what I was jumping into.

It worked out that I was a quick learner and did that for like three, four years, which helped me put together an application, a portfolio, enough of a career portfolio to apply to Northwestern to get my MBA at Kellogg. Surprisingly they took me, even with my poor GPA, although I had some stories to tell of overcoming some challenges and getting to where I was and having a cool job, the international business, that’s always something that they look for. I had to be one of those guys that wrote an extra essay and was like, “Hey. My GPA really sucks. Here’s why. I was new to the country and whatever.”

They let me in, and it was the coolest thing. It was like going to college again for me, because—or actually going to college for the first time, because those first four years in America I didn’t really feel part of America. I was an expat and there was no really context or knowledge of what college was supposed to be. It was a lot about learning and just kind of getting through, meeting amazing people, but where as I go to Kellogg, I knew what the experience was supposed to be. I had been in America for almost ten years. It had been nine years when I started. It was 2011. I was much more comfortable with my environment and what I was doing, what I wanted to do. I kind of had a vision, as opposed to I just want to make it in this new country. It was an amazing two years. It was awesome. It prepared me for what I’m doing now.

How did you first get interested in tech, or were you even interested in tech?

Yes. I was always kind of techy. Even in the early mid-90s I was one of the first kids in my block to be online, and BBSs, and kind of testing it out. Ever since I was just kind of into it. Obviously I wasn’t a programmer or not a computer engineer or anything like that, but it was something I was excited about. I always spent a ton of money on it, so I figured I might as well get paid by them. When I went to business school I was like, “Well, I definitely want to get out of sales and do some more strategic work and do more marketing, although I’m still interested in revenue, so much so that I am in the revenue organization on Twitter. I’m not like closing the sales, because I didn’t want to live with a quota over my head anymore, although that was an incredible experience, and it prepared me to do everything that I did ever since, but I knew that I didn’t want to do that anymore. I knew when I went to business school, I said, “Well, I’m going to go to business school. I’m going to switch careers. I’m going to switch from sales to marketing, and I’m going to switch from services to tech.” That was kind of the idea.

I interned at Dell in Austin, tested Austin out. I also knew that I kind of wanted to get out of Chicago. I love Chicago, but I knew that if I didn’t get out then, I would stay there forever, which would have been fine, because I love Chicago, but it was a time to like, “I want to test something out and go to a new city.” I was really looking at Austin, Seattle, and SF. Went to Austin for a summer, and it was great, but I like to say there was a little bit too much Texas around it, so I knew that it wasn’t quite my scene. I decided to come to SF and CISCO was good enough to give me a job. Packed up and moved one more time across the country, from D.C. to Chicago, and then out to SF, and worked for CISCO for a couple years. Then today was just my one year anniversary at Twitter.

What were your first impressions of Silicon Valley, and what did you expect, and did it or did it not meet those expectations?

Yeah. It was definitely—I had two experiences. I had one that was landing at SF, and living in the city, and meeting a ton of new people. I felt like it was a very easy place to meet people, just because everyone here’s a transplant essentially, or it feels that way anyway. Here I am living in a new city, single. I just want to meet people. It’s going to be great. I was lucky also that after graduating from Kellogg eleven percent of my class moved to Silicon Valley. Not only was it easy to meet new people, but I was coming with a built in group of friends. It was a really active period the first six months. It was awesome. We were going out, like going to places and then walking out I was like, “Why would I ever do that again? That was a nightmare.”

Then next week I’d find myself there. It’s a weird place. It was an incredible six months. It was really fun, but at the same time I’m working for CISCO. It is an incredible company, but I would argue it’s not a very fast paced company, not anymore anyway, at least not the part of the business I was in. You felt like, “I come to the SF and I wanted to be on the forefront of tech. I want to be testing things. I want to be doing things really quickly and testing things, and trying them out, and launching, having impact. Then learning from them and then trying new things. CISCO really wasn’t set up that way at all. That was kind of a challenge. It was a great job. It paid great, and I worked with very smart people, but I wasn’t quite fulfilled professionally in the way that I wanted. That was kind of hard. That didn’t meet my expectations obviously, because I moved here, expected to be in the middle of it. After a year and a half I was like, “This has been great. I feel like I’ve learned a lot, but I feel like the learning curve has stagnated a little bit, and I want to continue to learn, so it may be time to try something new.”

What are some of the things in your work that really excite you now? What are some of your favorite parts of your work?

I love the immediacy of my work. I work on—What I try to do is I try to get—I guess the mandate of my job is to get more Twitter users to advertise on Twitter in the simplest way possible. How do we find businesses? How do we get organizations that are on Twitter and get them to spend money to advertise to reach more people on Twitter? I love the fact that we can come up with an idea today, build something in a week, and by next Monday we have a prototype out and we can kind of see, does this have legs? Does it not? We should stop, or maybe we should keep going. The fact that we can point to it and say, “I did this, and this is the result, and these are the people I worked with.” It’s really, really rewarding, and I feel like I’m surrounded by people who are much smarter than I am. I’m always learning from them, and I’m always challenged in a way that I didn’t expect and taking my initial idea and taking it to places that I would have never come up with on my own. That’s really fun. I love that part of the job.

What have been some of your biggest struggles? I mean, obviously we’ve covered quite a few of them in your process to this point, but what have been kind of the tough parts of your career that you’ve had to overcome?

My career, it was certainly feeling like I’m in a dead end job. That was really hard. That was before—this was in Chicago, my first job. That was really—It was really hard. I’m generally a pretty positive person. That’s the only time my friends at the time—I’ve had multiple friends come up to me. It’s like, “Dude. You’re really negative.” I say, “Ah, fuck. It’s getting to me a guess.” Although they never really told me until after I switched jobs, and then they’re like, “You’re in a much better mood these days.” Then we figured out that I had been really negative for a long time. That was really hard. It was definitely one of those things where it was really hard to get a job when I needed a visa. Not a lot of places sponsor you and so forth. I felt like I ended up taking a job that having all of the opportunity around like I normally maybe not probably wouldn’t take, but it’s something that you kind of jump in and you figure it out as you go. After a year and a half I figured out that it wasn’t for me, and I figured out a way to get out. That was hard.

I haven’t been in this stuff long enough to have true dark times or real stressful times, although anytime you’re looking for a job or you’re trying to—that’s when the city gets a little bit less friendly I think, is when we get a little bit more into the career side. Everyone moves out here. It is the true gold rush. Right? Everyone moves out here. At least most people move out here. At least especially in tech to make a mark for themselves, make a name for themselves. There’s a little bit of that—It’s obviously not everyone, but you do find people who don’t really care about hurting other people’s chances or being unfair to other people in order to get ahead. Luckily I haven’t encountered too many of those situations, but it certainly comes up, certainly some of that happens.

Yeah. I’m curious to know what your personal experience has been as an immigrant working in tech or just in your career in general? You mentioned you have a challenge of identifying role models you can personally identify with and little things like that. What is that experience like?

That’s really—There are a couple things that I can really point to that are positive and negative. On the negative side anyway it was hard because no one in my family went to college in Brazil, but even less so in America, so I was really lucky to be surrounded by people in D.C. who really took me under their wings, and were willing to help me, and study for the SAT with me, and write recommendations for me when they really didn’t have to. I find myself very lucky to have been in the right place in the right time, but I can completely understand how it would have been really hard if maybe I did land in D.C., maybe I landed in a more conservative area or a place where there isn’t that influx of expats so often that you kind of get used to kind of the challenge of an immigrant. I was really lucky in that sense, but for a while it was hard, because I have no idea what I was doing.

I was lucky that there was someone there to help me. I’ve been lucky to have friends that a couple times have been older to me and introduced me to the idea of an MBA. I had no idea that was an option really.—and see how people do it. It was like, “Fuck. That sounds like fun. That sounds like it would help my career and sounds like something I would want to learn about.” Again, I think I’m very lucky to have landed in places that are welcoming, mostly welcoming, to immigrants, really just open minded. That really helped me out, but you still always kind of feel like you don’t really know what you’re doing, even a little bit more than—I feel like most people feel that way anyway. At least that’s the way I felt. Should I be applying for school? Should I be getting my MBA? Should I be trying to get this job? There’s not a lot of people around you that have gone through the same path.

“That being said, I’ve had a really, really strange experience as an immigrant because—this is weird. Hopefully it doesn’t come out the wrong way, but I’ve been able to blend in in a really strange way. I’ve been at tables, just lunch tables, and I make a comment like—We’ll be talking about minorities or whatever and—It’s always on the news and we’ll talk about something. I’m like, “Yeah. We’re all minorities here.” Then someone will look at me and is like, “Well, not everyone,” as in they assume I’m a white guy, which is a strange thing. In a lot of people’s minds, until they get to know me or know a little bit about my story, they think I’m a white, American dude called Enrique, which makes no sense in the world. When they hear I’m Brazilian a lot of people ask, “Oh. So like your parents are Brazilian?” I’m like, “No. I was born and raised in Brazil. I’ve had the immigrant experience.” In a sense it hasn’t …

I guess what I’m trying to get at is I’ve been able to kind of hide in plain sight and avoid some of the immediate sort of reactions that—It was really surprising to me that someone was born in America, but was Mexican—I had friends like that that suffered way more prejudice than I ever did, because I have lighter color skin, and I have light eyes. It was a strange sort of—I’ve always kind of struggled with that identity that I’m called white very, very often. Obviously that’s not a bad thing. It’s not a bad or a good thing. It’s whatever, but it’s certainly not my experience, or at least maybe it is, because I’m considered white when people kind of in passing treat me in any kind of way. It’s definitely not my human experience of growing up and moving to America, and figuring things out. It’s been a strange experience a couple times to be confused for a suburban white guy that happens to be called Enrique. That doesn’t quite compute. It’s been strange, but I think overwhelmingly my experience has been positive. As I said, I’m really lucky to have landed at the right places surrounded by the right people completely by chance. Yeah. I think that’s as much as I can talk about that.

Yeah. That’s interesting. I’ve interviewed a couple of girls in this project who are black, but have lighter skin and have gone through really similar experiences where people will literally say some really racist shit in front of them, and they’re like, “Uh. You know I’m black right?” They just don’t even know, because they’re not black enough that it doesn’t register in their mind that this is a black person that they’re making a black joke in front of. It doesn’t register. That’s mind blowing.

It’s strange. Sometimes you pick up that fight. Sometimes you’re like, “Dude. That’s not—You probably shouldn’t be saying those things, and not because I’m Latino, it’s because that’s a racist thing to say. Nobody should say that.” Sometimes you’ll find yourself in that place—for whatever reason you’re in an environment that you don’t want to pick that fight, or you don’t want to be the person who starts a thing, and you have to kind of sit there and kind of play along. It’s like, “Well, I’ll play along for now, but good to know that you’re not a person I probably want to trust. You’re probably not a very good person if you believe what you’re saying.” Yeah.

It’s a strange thing. As I said, at least in my opinion it’s come as a blessing, because I’ve been, as I said, like hiding in plain sight, and people don’t treat me very differently. I feel like although I’ve had a lot of the immigrant experience, I haven’t had the minority experience, if you can split those two, and maybe you can, maybe you can’t, but I’ve had a lot of the immigrant experience of I just don’t know what I’m doing here, and I’m going to try to do this thing, but I have no idea how to get there, but I haven’t had the minority experience of being pulled over often or—I don’t know. That encompasses so many things, but I think you know what I’m saying.

Yeah. I think it’s a unique position to be in honestly, just based on what I’ve heard from all these interviews of like you are going to experience many, many micro-aggressions or aggressions that weren’t intended for you, but you are definitely affected by it. You know? It’s a really interesting thing where for me if someone makes a racist joke in front of me, I know it’s not for me, but it’s still like, “Dude. Don’t say that shit.” You know what I mean? I’m not even affected in the same way as—My sister’s half black, and she deals with this shit all the time, this like, “Uh. You didn’t know? I’m black.” It’s just like a funny situation.

Yeah. It’s one of those things that’s just part of life. I don’t know. It’s certainly been an interesting—how long it’s been now? Fourteen years? Yeah, in that sense of—Yeah. When I lived in D.C., traveling through Virginia and being just different enough that people kind of look at you funny—Maybe I was still tan enough that when I came from Brazil it was still soon enough when I moved here.

And it’s Virginia.

Right. That’s what I mean is anytime—I’m white enough to blend in urban areas, but when you leave those areas you definitely notice that things change a little bit.

Oh, yeah. Yeah. There’s definitely a—I’m from North Carolina, so there’s definitely a tighter set of requirements for being normal. I was too pale so I was weird. You know? It’s dumb.

It’s culture. It’s hard to generalize. There’s obviously a lot of good people, amazing people, in all places in America, but the norms change.

Yeah. For sure. What would you say are your biggest motivators? What drives you?

Man. Let’s see. I want to give you an answer that’s not really lame.

Well, it’s kind of a hard question. A lot of people are like, “Oh, shit. I haven’t even thought about this.”

I know. I don’t want to default to motivated by becoming a better person, whatever. I want to come up with a real answer. I’m motivated by two things. Well, I can think of two things that motivate me. One is actually the fact that I do like to learn and moving to SF I’ve been exposed to—I’ve started working with engineers and working with people who studied very different things from me, and I love learning what they know and adding those skill sets to my tool belt, if you will. I love that in the two years I’ve been here I’ve learned full programming languages. Not programming, but I know how to do SQL. I know how to do R for analysis. I like that kind of stuff. I like to be able to point to something and it’s like, “I learned that thing. I couldn’t do that a year ago, and now I can do that.” That’s really cool. I love to be able to do that.

At a personal level though what motivates me a lot is the experience of my grandfather who I was named after. He’s an interesting guy, because he was born in a very poor city of the Northeast of Brazil. He didn’t go to school until like he was in his teen years. At that point he moved to Rio, like the big city if you will, and lived with his uncle, or aunt, or something like that, and tried to get into a private school, because it was an issue for—You really try to avoid public education in Brazil.—and got turned away by the principal. He took a test and he’s like, “You’re never going to make it.” In a way it was the sort of regional you see in Brazil, which sometimes you see a different kind in America as well. In Rio it’s like, “Oh, you’re coming from the country, and you’re never going to make it here. You took a introductory test, and you’re so far below the bar you’re never going to make it.”

He went back, and he studied his ass off, and went back months later, and took the test again, and had the highest score. After that he was number one in his class his whole career, enrolled in the Navy, became a four star admiral, became a direct advisor to the first democratically elected president in Brazil in 1995. He had this stellar career. I really look at it and see how far he came and how he was able to bring his family out of poverty really in the Northeast. Maybe not poverty, but not a lot of opportunities to have kids that were able to get good educations and we’re able to have careers in Rio, and travel, and really open up the opportunities for his family. I look at that and say, “Okay. Well, because of him I was given a much better shot at having an opportunity to make a difference and to take my family from point A to point B.” I guess he did from point A to B. I guess I’m looking at point B to point C or whatever that is. That always keeps me in check and motivates me.

My grandfather went through much harder things and because of his hard work I don’t have to, so what can I do with that. What can I do with the hand that I’ve been dealt. I cherish being lucky. I find myself to have been very lucky since I moved to the U.S., being around good people, landing in good places. I never turn down an opportunity for that reason, because I try to appreciate the hand I’ve been dealt. I know personally what my grandfather had to go though to kind of impact the hand I was dealt in a way. That in a personal way that motivated me a lot. I try to keep track of that and stay on top of it.

How do you feel about the state of tech in 2016? What really excites you about it? What frustrates you about it? What would you like to see change?

“Yeah. I mean what excited me about it is something that has excited me for a long time. This is where the innovation that will impact the next twenty, thirty, fifty years, that’s where it’s happening, whether we’re talking about self-driving cars or whether we’re talking about new ways to communicate and affect revolutions and whatever, that’s really exciting to me. The way that the world is being transformed through technology, and a lot of that happens in Silicon Valley. The same thing that excited me twenty years ago—Although I didn’t understand it as to what was happening, but I was excited about the fact that things were changing, that’s what excites me.

The frustrating thing is even though we’re on the forefront and—Well, let me think about that. One of the things that frustrates me is that technology as a whole has been a driver for change within the technology world and within the business world as far as we’re—The tech companies, a lot of it is what’s driving the economy these days. Two out of the three most valuable companies in the world are tech companies. Right? We’re talking about Google. We’re talking about Apple. If you go to the top five, we have Amazon and Facebook, so we’re driving a lot of the changes.

I don’t think we’ve been able to impact policy. We’ve haven’t been able to impact culture, other than in big cities. Yeah. Mostly in big cities. We haven’t kind of been able to really become a mass appeal. Obviously it’s a slow process, but I’m frustrated by the fact that it’s been slow and the fact that—That shows itself in a lot of different ways, but I think policy has been a point of frustration for me, that there’s so much more information there and technology has tried to make efforts to make that available to people, but people still don’t have enough information to make the big decisions they have to make every day and/or every four years, or every two years, or whatever. It’s a really big challenge for people to have the right information at the right time. I think that’s frustrating that we haven’t been able to make that happen.

On a personal level it is frustrating to look around and see most boards of companies, most executive teams of companies, don’t have a representation of Latinos. There’s a big focus on adding diversity, but that’s just so hard. Twitter made it public last year that thirty-five percent—Whatever. I forget the number, but it is minority is diverse and the goal for this year is to increase it by one percent. I get it that it’s hard, but Jesus, like one percent. We can do better than this. That’s definitely a frustration. I feel like we haven’t—I don’t know. It feels like we haven’t really so many times put our money where our mouth is a lot of the time. I feel like we are so worried about the little Silicon Valley world of who has the highest valuation, who sold It for the biggest amount of money, who’s the new darling of VCs? We have all this cash, all this impact, we  can make such a big difference. We choose not to, because there’s all these other competing priorities. That being said, I’ve never been in a position where I had an opportunity to be a darling of a VC or sell it for hundreds of millions of dollars, so maybe I would have made the same choices. I’ve never had that experience, but looking from the outside it is certainly something that you look at as like it just looks like a missed opportunity.

I agree. 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? What kind of lessons have you learned that you’d share?

My advice is that it can be done. It can be done. You can’t be afraid of failing. One of the things that I learned by moving to America and—Maybe that could have happened in any country, because it’s really based on—because I’m speaking a language that I don’t have command of you just fail every twenty-five seconds in the most basic level. You just speak poorly or don’t understand something that’s around you. You can react a couple different ways to that. You can either shut down and say like “I’m just going to hang out with my Brazilian friends, because it’s easy,” or you can, “You know what? Screw it. I’m going to fail a ton, but I know that I can learn from it, and I can get better.” One of the reasons why I think I went with the latter was because I knew I was leaving in two years, which ended up not happening, but I was like, “Who cares? Right? I have nothing to lose. I’m going to leave in two years anyway.” That really made an impact. It kind of really changed the way I was wired in the sense that failing was totally okay. It’s the only way you learn. It’s the only way you can try, but you have to understand that—It’s kind of like career or …

Most of life really is kind of like baseball. If you can hit it thirty percent of the time, you’re doing really well. I guess my biggest advice is that it can be done, but you’re not going to go one for one or even one for two. You might have to try a few different times and reach out to people, try to find people that could relate to you, or try to reach out to anybody. I feel like most people would be willing to help you. You don’t have to pull on the racial string or similar experience, although that could be helpful. I think it can be done. I think people here are more welcoming than most places in the world, because like I said, we’re all transplants. We’ve all experienced in some sort of fashion being an outsider in SF, because most people came from outside of SF. I think people are more open than in most places. That would be my advice.