My family’s from a farming community in Haiti. When my parents moved to Boston in their mid twenties, they had children pretty immediately. At the time, me and my 3 siblings lived in mostly illegal communities. It’s interesting because you don’t know that you live in that sort of community until you start meeting Americans who live a bit differently. We were very “green.” We used buckets of water to bathe instead of running shower water. Our front lawn was a garden. My parents were not accustomed to refrigerators so they became a pneumonia scare in our household. In fact, to them everything caused pneumonia and everything could be cured with a cup of tea.

“At the time, me and my 3 siblings lived in mostly illegal communities. It’s interesting because you don’t know that you live in that sort of community until you start meeting Americans who live a bit differently. We were very “green.” We used buckets of water to bathe instead of running shower water.”

Growing up I was a very, very inquisitive child. I constantly asked questions, and context clues meant everything to me. It always confused me how people would do things without asking why? My parents had a lot of difficulty answering my questions due to the language and culture barriers. They encouraged me to read more, with the mindset that the bigger the book, the smarter I would be. The older and dustier the book, the smarter I would be. The harder the cover, the smarter I would be. Really interesting context when you really think about it. I eventually started reading dictionaries and encyclopedias, searching for answers.

When I was 11 years old, I noticed an advertisement on the back of a magazine with the words, “Do you have questions?” I took this as a sign to get tons of questions answered. I ran away from home in search for the magazine headquarter, which happened to be in Boston. Upon arrival, there was a massive exchange of questioning and they soon realized that I had no idea what my address, phone number or birthday was. They sat me in front of a computer and taught me how to play solitaire until my mother eventually found me. My question started to shift from day to day questions, to questions around machinery, interface and context. That began my path into the world of User Experience.

How were you were first introduced to Computer Science and/or UX?

Well my mom brought me back to the magazine HQ the following Monday and told me not to tell my father. In our household, the girls were very protected. I was supposed to go to school and get home as quickly as possible. I was not allowed to make friends. But my mom was a bit of a secret feminist and encouraged me to outsmart the boys and teach her all I had learned in school. Staff at the magazine were pretty impressed by me and encouraged me to continue learning about technology. They eventually were able to take me to a place called The Computer Clubhouse while my mom worked. The Computer Clubhouse was a free technical after school program designed by professors and students at the MIT Media Lab. They targeted inner city kids as young as 8 years old and taught us how to use industry level technical tools. They believed exposing underrepresented individuals to a number of technical skills early on, could help bridge the digital divide. The additional blessing was the frequent visits from people of color at MIT pursuing PhDs in Computer Science and Media. At age 12, I played with actuators and sensors. I also was introduced to coding and programed the very first driverless lego cars.

When I was 14 years old, I ended up in foster care due to a variety of reasons including domestic violence and cultural friction. I ran away a lot and was very depressed through those middle school and high school years without my family. Despite all the personal struggle, I always found my way back to the computer clubhouse. I had all these cool tech skills and loved teaching. By the time I was 17 years old, I was teaching girls how to make their own web pages and remove the proof watermark off photos they had not yet purchased from school. I shortly became an assistant manager at the computer clubhouse, a Tech coordinator at the local YWCAs, the Museum of Science’s technology courses instructor and an IT risk auditor at Harvard University all while I attended undergrad.

“When I was 14 years old, I ended up in foster care due to a variety of reasons including domestic violence and cultural friction. I ran away a lot and was very depressed through those middle school and high school years without my family.”

Despite all of my technical ability, I was too scared to pursue a computer science degree. I believed it was a man’s job despite the fact that I was already doing it. So I went to school for Information Systems and sociology while teaching computer science on the side. When I was in my junior year at undergrad, I decided to take a java course and was pleasantly surprised. I already knew how to do a lot of this stuff. The wave of questions began again. “Does that mean I can code? What’s the point of the degree? Do you need a degree to be a coder? I’m confused. Can you just learn this stuff on your own? Are you not an engineer unless you learn to be engineer in school? Are Haitians who build bridges without degrees not engineers? Wait, what do I do with this sociology degree?” Sociology was the field that touched my heart and technology was the field that stimulated my mind.

I took several psychology classes and professors really felt that it might be my calling. But I could not imagine humanities paying back school loans. By the time I graduated I decided I wanted to do it all. I took to the Google search engine and typed in all my passions, “sociology, psychology, computer science, engineering, hands on, love, forgiveness…” And two fields popped up—human factors engineering and human computer interaction.

How did you make that transition?

I went to Michigan to pursue both degrees: a masters in human computer interaction and a PhD in Human Factors Engineering. It was EVERYTHING. I had somehow found fields that connected culture, engineering, empathy and compassion. And I got to doodle all day to top it off. The wonderful thing about the Computer Clubhouse is that it was funded by Intel. I was able to work my way through the network and worked as a human factors engineer while attending grad school.

At Intel, I met an amazing woman and Intel Fellow known as Genevieve Bell. Genevieve was an anthropologist and a human factors engineer who focused on cultural practices. That was the moment my entire life started to make sense. I had grown to a place where I truly appreciated cultural differences and empathized with day to day struggles of Keeping Up with the Silicon Valley Millennials. I knew I could help make life a little more easier. I wanted to help design products that showcased empathy. And I knew it was my destiny.

Walk me through your work and what you’re working on now.

I eventually went on to work on international projects as either a developer, engineer, or designer across many industries; from government to medical devices to worldwide leaders in IT. Today, I continue the great work at Google in the consumer operations space. I get to measure my work impact globally. I am also launching a personal global passion project called Tech Social Impact Conference in the first quarter of 2017. The conference sparks conversation about developing intentional awareness in product development. In Silicon Valley, we get to see how design and technology can provide social and ethical benefits (and sometimes consequences). I’d like us to share principles and approaches to contribute to a better tomorrow for the next billion users.

“Another goal I am working on is changing the way we do research in the tech industry. I want to make that our research takes into account social and economic backgrounds. Are we designing towards the average income in the United States? Are our studies mix gendered? Have we paid attention to accessibility? I’m all about making a difference in this world, and I know I am in a very privileged position to influence that change.”

Another goal I am working on is changing the way we do research in the tech industry. I want to make that our research takes into account social and economic backgrounds. Are we designing towards the average income in the United States? Are our studies mix gendered? Have we paid attention to accessibility? I’m all about making a difference in this world, and I know I am in a very privileged position to influence that change.

It’s so cool to see all of the ties to your work from your childhood to now. What parts of your work as a researcher really activate you? What do you love the most?

I get super excited when I get in front of people, and I mean real people (no offense to Silicon Valley folks), I’m so passionate and empathetic towards the people I design for. When they’re in front of me, I want them to be comfortable. I want to hear their truths. I want them to tell us how we suck. I want them to know that I appreciate it, and I want to make a difference for them.

It’s one of those things, when I’m in front of somebody, when I’m in front of an actual human being, to know that, “okay, maybe you don’t have the same technical abilities as I, or maybe you feel a little scared, but I’m going to change this for you. I’m going to make this easier for you.” It empowers me. I just ran eight studies today with folks, and every last one of them said, “I’m not really good at tech. I feel like I’m messing up.” I say, “This is exactly what I need. And you’re perfect. I need you to tell us everything we could be doing wrong, so we can fix this for the lot of you that may feel the same. It’s not about looking for a tech genius. If that was the case, we’d make no money. And we need you to keep paying us, so I need to know everything that makes you cringe and what makes you happy.”

I’m curious to know, in your eyes, the potential of research in tech and what are the problems that we should be solving with research? What are we not doing to approach this correctly?

The reason research is so beautiful is because it’s data. When folks try to say “This is how I feel this should be designed,” I can say “Well, 80 percent of people we tested won’t go through it.” Or when I hear, “Can these users really speak for the rest of the country?” I’ll say, “Well, you know there’s this little thing called sample sizing. Pretty dope stuff.” It’s just really empowering to influence people with research.

“We’re not building for just ourselves anymore. We’re a global society. Everyone is using our technology. There is a huge culture shift and focus on design for the next billion users and I think it’s a great direction. And guess what? Sometimes design requires contrast. That means we may need to have different people seated at the table to help us design. You might just have to hire that super poor person in the village you’re building for. It might just mean spending time living in the communities you are serving. It might mean better design for our products due to diversity of thought.”

The problems we should be solving for is cross-culture design. We’re not building for just ourselves anymore. We’re a global society. Everyone is using our technology. There is a huge culture shift and focus on design for the next billion users and I think it’s a great direction. And guess what? Sometimes design requires contrast. That means we may need to have different people seated at the table to help us design. You might just have to hire that super poor person in the village you’re building for. It might just mean spending time living in the communities you are serving. It might mean better design for our products due to diversity of thought. I see nothing but wins when you consider research as a primary practice to help think more critically about the ethical and societal implications of the technologies we design in this world.

Let’s go back to your personal narrative. Tell me about some of the bigger roadblocks and struggles, in your career that you’ve had to overcome.

Being yourself in a world where being yourself seems wrong. In the last year mentors have been telling me that I can fully be myself and be accepted. I never believed that. It wasn’t because no one was telling me I couldn’t be myself. The culture just didn’t seem to want me. So I faked it. I fake laughed at jokes, I fake pretended to see movies I hadn’t seen. I faked drinking beer when I thought it was disgusting. I tried to be a bro when there’s not an ounce of bro in me. It’s pretty draining because I would spend 80 percent of my day pretending to be somebody else­­ or I’d sit in silence when I’m not a silent person. There’s some parts of me I just cannot hold back, like when I disagree.

“In the last year mentors have been telling me that I can fully be myself and be accepted. I never believed that. It wasn’t because no one was telling me I couldn’t be myself. The culture just didn’t seem to want me. So I faked it. I fake laughed at jokes, I fake pretended to see movies I hadn’t seen. I faked drinking beer when I thought it was disgusting. I tried to be a bro when there’s not an ounce of bro in me. It’s pretty draining because I would spend 80 percent of my day pretending to be somebody else­­ or I’d sit in silence when I’m not a silent person.”

It’s still a work in progress but I’m trying to be unapologetically myself no matter where I go. I’m now about 70% myself which is pretty amazing. I would never have imagined that. And I have experienced so much good because of it. A mentor once told me that the Valley was a strange enough place where I could fit in and be appreciated for my differences because everyone is so different. Another mentor told me, “I don’t know if you know this, but when computer science first came out, it was considered a woman’s job. It was like secretarial work. But all of a sudden because somebody told us women we can’t do this­­ or that— that perceived ability has disabled some of our powers. It’s insane. And we as women are fully capable of doing any and everything in tech, if not better.” These words definitely helped.

When did your attention start turning towards educating minority communities?

I’m very passionate about that because someone took the time to show me that I wasn’t forgotten and look how far I’ve gone. And it’s important to know that it also took someone that looked like me. So I serve that truth right back.

I also truly believe this—if you want to hire somebody, look at their story. The story matters to me. That’s how you find out actionable potential. That’s how you know that you can take this kid off the street, show him a few lines of code, and all the sudden he’s the inventor of a killer startup. It’s about finding folks that are hungry. So I set up the environment, and the folks who are hungry, come to eat.

“If you want to hire somebody, look at their story. The story matters to me. That’s how you find out actionable potential. That’s how you know that you can take this kid off the street, show him a few lines of code, and all the sudden he’s the inventor of a killer startup. It’s about finding folks that are hungry. So I set up the environment, and the folks who are hungry, come to eat.”

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

Everything I’ve done has been because of experiences I’ve had. At one point I wanted to prove my value because I felt tossed away by the world. Now, it’s about making people know they are valued and impacting the world that way.

Last question. What advice would you have for young women, young people of color who are really hoping to get into tech but just don’t know where to start?

Look at several LinkedIn profiles for individuals who are in the career you want. Write down all the things that interest you and the common themes/skills. Teach yourself those skills. Put said skill into practice. Slap new skill on resume. Rinse. Repeat.

The majority of the things I know came from tinkering, searching for free education online, and application of that education. Don’t believe the hype that you have to be in school to learn new things. Now I don’t mean drop out. College is awesome. Go to college if you can. What I mean is that you can teach yourself almost anything these days. if you allow for a little discipline. What kept me motivated was knowing that the short term sacrifice of taking the time to learn something on my own, was going to lead to longterm rewards.

“Look at several LinkedIn profiles for individuals who are in the career you want. Write down all the things that interest you and the common themes/skills. Teach yourself those skills. Put said skill into practice. Slap new skill on resume. Rinse. Repeat.”

And please, don’t be like me for the majority of my life and not ask for help. The world is so much better when you stay open and vulnerable about learning through others. Lastly, sounds cliche, but no such thing as a dumb question. Get your education on.

I come from Seattle, Washington. I was born and raised there. My parents were a typical blue collar, working class, immigrant family. They made tofu for a living, and so I grew up in a world where soybeans were everywhere. We sold the tofu to two kinds of customers: regular folks like teachers or gardeners, or to businesses like restaurants. And it was very hard work, working all the time, waking up early in the morning ­ two o’clock in the morning ­ working to six at night. It was pretty intense, but I learned how to work.

What did your parents expect of you in term of a career?

My mom’s the third generation and my dad’s first. They just wanted us to get to college somehow. That was just a dream, because both of them hadn’t gone to college. My dad didn’t go to high school.

When did you first feel any inclinations towards tech or design?

I was lucky to have been born in the era when the Commodore PET came out, which was a little computer. I was also lucky to receive the benefit of the civil rights work in the 60s. Seattle was de­segregated. The people on the poorer side of town were bussed to the richer side of town. I was in the poor side of town. I was bussed to the rich side of town and they had this computer in math class. That’s where I found my first computer in the 70s.

Then you ended up going into software engineering as a student, correct?

Yeah. It was really my parents’ dream for us to go to college and it was either Harvard or MIT. My older brother didn’t get into Harvard, so he was considered a failure [chuckles]. So I said, “Well, I’ve got to get into MIT,” and I got to MIT and studied computer science there.

“If you connect your understanding of technology with an understanding of the history of art, you can do something new. When you do something new, it hurts because nobody likes what you’re doing because it’s different. I think our inclination is to be afraid of that pain.”

When did you become interested in design and then the integration of the two?

Well I think as a child I was said to be good at math and art, but my parents would never tell anybody I was good at art because they felt that couldn’t get you a job. I was “good at math” is what they’d always say. I loved drawing. I loved thinking visually. When I got to MIT, I tried to defect. I discovered this department called “architecture.” My dad figured out what I was doing so, “No, no, no, no, no. You’re not going to be able to feed yourself, so computer science; go back there,” kind of thing. But I used to go to the library at MIT and I would find these books on design. At the time I was probably one of the best icon editors on campus at MIT. Computers were just becoming visual and I was the guy that could make good icons. I thought I was really good at it. Then I found this book by Paul Rand, the graphic designer, and I thought, “Man, he is so much better than I am at this stuff.” [chuckles] That’s how I found the field of design.

Such a huge part of your work is combining tech and art and exploring the integration of the two. When did this feel like a focal point for you more than just doing the work that’s assigned to you?

That’s a great question. I forget all the time that I cared about that, if that makes sense. I’ll be waking up and saying, “Oh yeah, I care about how those two connect.” Then I’m off forgetting everything. “Oh yeah, I care about that.”

I guess it’s because I was lucky in the 80s and 90s to see how, if you connect your understanding of technology with an understanding of the history of art, you can do something new. When you do something new, it hurts because nobody likes what you’re doing because it’s different. Each time you touch that third rail, you’re like, “Ouch! I don’t want to do that. I want to be a regular engineer. Or, I want to be a regular artist.” So I think our inclination is to be afraid of that pain. I’ll come close to it and I’ll go away from it [chuckles] and I’ll come close to it and then go away from it. I’ve always been having this problem. I’ll be in art school, I’ll be in engineering school, I’ll be in Silicon Valley. I’ve always been running from and towards the third rail.

“I’ve always experienced push­back. In art school, I remember in the early 90s my conservative design teachers told me, “Stop making things move on the screen. That’s not right.” Or being at MIT, and my engineering teachers telling me, “Why do you care how it feels, just make it run faster.” I think that anyone messing with the field they’re in, and how it’s “supposed to be” gets in trouble and it goes back to that key question: “How much pain can you take standing at the intersection of fields?” I guess I’ve always wanted to feel that pain. I guess I feel alive in it.”

I don’t think we have time to run through the entire course of your career but at a high level, what aspects of your work have you been proudest of, and what about your work activates you?

Wow. Well I think any creative person you talk to will tell you they’re not really proud of what they’ve done, because they’re still searching. So I don’t think I’m proud of anything I’ve ever done. I think that I’m always surprised when I see something I did in the past ­. What I’ve seen about getting older, is you’re like, “Did I do that? I don’t remember doing that. I guess that was kind of okay, but I could have done better” kind of thing [chuckles]. So nothing in particular, really. I’m glad that I’ve continued to learn, try new things. Being in venture capital is my most ambitious art project to date.

I definitely want to go into that with you, in a little bit. In terms of integrating the tech and art worlds, did people see it the way­ or as naturally as you see it? Like, from a political perspective, has there been push­back from either side, when you’ve for instance been pushing tech onto RISD, or pushing art into Silicon Valley?

Yeah. I think. I’m glad you asked that question. I’ve always experienced push­back. In art school, I remember in the early 90s my conservative design teachers told me, “Stop making things move on the screen. That’s not right.” Or being at MIT, and my engineering teachers telling me, “Why do you care how it feels, just make it run faster.” I think that anyone messing with the field they’re in, and how it’s “supposed to be” gets in trouble and it goes back to that key question: “How much pain can you take standing at the intersection of fields?” I guess I’ve always wanted to feel that pain. I guess I feel alive in it.

What are the problems that you seek to solve with your work?

Right now I want to address the fact that most of the power in the world is controlled by people who understand money, and in many cases have understood it for multiple generations.

Creative people are trained to not care for money. I think because of this, creative peope—when I say creative people, I mean like arts, design, or even engineers who love to make things—or “makers” tend to believe that money is evil, bad, corrupting, dangerous. My passion is to enable makers to understand that money is just a medium. And like all media, it can do good, it can do bad. In the same way we can’t say that all art does good—there are bad artists. There are Evil artists. and so money can be used in the same way: for good, for bad.

Similar but slightly different question: What are the biggest motivators in your work? What drives you?

To question what I know, because I’m supposed to know a lot of things. And each time I feel, “Maybe I understand this,” I’m like, “Oh, I don’t get it.” Being in Silicon Valley has been so humbling. To meet people like yourself who are really in a whole different way of thinking that I overlooked, and didn’t fully understand, and I wasn’t a part of. That’s why for me, living here­­ I’ve been living in like a Millennial, I have no possessions, and am living in Airbnbs and Uber­ing everywhere. To understand how your generation feels right now has been an exciting moment for me. I love this project you’re doing and I love how you imagined it and I love how after you have gone through most iterations of yourself, you came to see this as important and there’s nothing to stop you. You just said, “I’m going to do it. Suddenly, I have 500 people who want to be a part of it.” And I thought, “Thank goodness that people like you are saying, ‘Of course I can. Because technology is something I’m not afraid of, but I’m not just technologist. I’m a person of culture, and I’ll combine them together and show them.’”

“Being in venture capital is my most ambitious art project to date.”

Amen and thank you. This is a little bit of a side step, but you’re on the board of Wieden, and I’m curious to hear how you apply your perspectives and methodology to advertising.

Oh. Well, a lot of my passion is going back to the world of money, the world of control. I’d like to be a creative person who is in board roles who can argue for creative. So on Wieden’s board, I channel the guy who can talk money, but can talk creative too. The questions always have to be not about pure profitability, but creative integrity. And the reason why Dan Wieden brought me into his world is that he wanted to make sure that all the discussions come back to, “Are we a creative culture?” So I like those kinds of roles, where creativity matters at the very top. I recognize that such opportunities are precious, and are meant to be made into something, and to be taken to their fullest.

When was the moment when money became important to you as something integral in the design process?

It was in the year 2001. It was the dot­com crash. And some of my colleagues at MIT owned a lot of stocks. And we were at a meeting where they were facepalming and going, “Oh no, oh no,” because they were losing all kinds of money. I had no money, so I didn’t know what they were talking about [chuckles]. And oh my gosh. Shortly thereafter, MIT did some restructuring, and I remember there was a CFO type person who said to me, “John, you’re the creative person, so don’t worry about the money. We’ll figure it out. You just go and be creative.” And he was maybe the third person in my life who had said the same thing to me. And when someone tells you, “Don’t worry your pretty little head, John. It’s going to be okay,” I get worried. I wonder, “What are you hiding from me?” And I realized, I would read newspapers and not understand the financial terms ­­ and the legal terms too. Sure, I could read People Magazine, one of my favorite things. And it’s so vacuous, and easy to read. But I couldn’t read The Wall Street Journal. And so I did my MBA to begin to learn the language of the finance and business world to get to feeling, “Oh that’s what you’re saying. Oh that’s what I didn’t understand.” Here I was, limited to being told that I’ll do the creative part, and you someone else would do the money part. I wondered, “How much am I giving away? How do I take back my integrity?” That’s where this drive all came from.

Interesting. Did you ever expect to be in Silicon Valley Venture Capital?

Never. I actually had never heard of “venture capital” until I got to Silicon Valley. Well, I kind of heard of it; but I didn’t know what it was at all. In full disclosure, I just sort of bumble into things. With the attitude like, “Oh, I’ll try that,. I’ll try that.” I remember feeling, “Venture Capital? What is that?” Two months before I arrived I bought a book on venture capital. I read it, didn’t quite understand it. So since I’ve arrived, it’s just been a lot of learning. I marveled at how a little bit of money can become a large amount of money? I didn’t know it was possible.  I then wondered, “Wait, so what are the letters? What do they mean? Oh, they’re in sequence. Okay, I get it.” All these things that I had no idea about­­ and just to realize it now in my lifetime has felt like a blessing.

I’ve also found that people who find out I work in venture capital will say to me, “Oh, venture capitalists, they’re bad, bad”. I don’t know what they’re talking about. I know a lot of bad people in the academic world – and some good ones. And I can say I know a lot of good venture capitalists – they’re pretty amazing. I love how their goal is to see the impossible happen. And when we think in this start­up, Silicon Valley world, that’s a kind of a mantra—you know, “Make the world a better place” or whatever—I love that the people who have the funds to power these things, a significant percentage of them, do believe the impossible is possible. I think that’s magic.

Tell me more about your first impressions of Silicon Valley.

Well, you know that my first impression was – the lack of  diversity in tech, and how there aren’t enough women, people of color, and it’s not addressed sufficiently. I noticed it from the very beginning. But then I noticed that it was because I myself wasn’t making a conscious effort to change that in my own activities. Maybe in my first few months I met mainly young white men, because they would introduce me to more young white men. And so after a while I realized, “Oh, maybe I’m doing this wrong. It isn’t that the system is doing me wrong; what do I have to do differently?” So I began asking myself if I’m having ten people that I’m seeing, how can I now consciously edit my direction. I found that my conversations and gatherings became so much better than when they were less diverse.

So when people say that diversity is important, I like to say instead, “No, it isn’t important. It’s essential to increase the quality of discourse.” When I was leading RISD, I had the opposite problem because there were ~70% or more women in the student body. So I would always be like, “So where are the men?” So again, we have to recognize the situation we’re in and we have to take action. But I’m by no means perfect with regards to my diversity record, but I do strive to be conscious, aware, and take action on the matter.

“When people say that diversity is important, I like to say instead, ‘No, it isn’t important. It’s essential to increase the quality of discourse.’“

Tell me about how kind of the culmination of your previous work impacts how you’re approaching your work in VC.

Oh, absolutely. I became president of a college in 2008 because I read the “Audacity of Hope,” and I listened to the audio book and it was so inspiring as an American to hear that anyone, any American, no matter what age, race, or creed can make a difference. “Yes, we can.” So, when the headhunting firm, Spencer Stuart, called me up and said, “Hey, you want to be president of a college?” And I said, “I can’t do that.” But yeah, I finished my MBA, but I don’t have any experience, and I was never a dean or a provost or all these special titles along the way. I can’t do that. And in my voice I could hear, “Yes we can. Yes we can!”

And so Obama became president that year—the same year the financial crisis happened. Me too, I was brought in as a person who was going to bring in new ideas, and then shortly after I arrive I’m overseeing the worst layoff in the history of the place. And I’m no longer a person with ideas, and immediately assume the role of the pragmatist and operator working to navigate a financial crisis. And it was kind of like a sock in the gut and in the face. And so I had to become a different person. And I’m grateful because otherwise I wouldn’t have learned how to operate at scale as a leader.  I wouldn’t have had to reform the business model, or really understand the business of a university, and to understand where every dime goes. That was a great outcome, but a hard process along the way. And so I come to Silicon Valley to learn that this knowledge of how to run an organization at scale through difficult times is valuable here, which I find very promising and positive. It isn’t that people here are all about fail fast. It’s, “Can you recover fast?” And I’ know how to recover – it just takes hard, and smart, work.

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

I think what excites me is that there’s a kind of awareness that maybe we need to make things for more kinds of people than those who live in Silicon Valley. You can call it diversity, inclusion, all kinds of things ­­ it doesn’t matter. We recognize there’s a strong business case for matters that impact people who live outside this region, and by knowing what they care about, we can  actually have a bigger impact. That excites me: not the technology. There’s a realization occurring here in this region.

What turns me off? ­­ I don’t know. I mean, so many things get me grumpy in general, I guess [laughter] if there were one thing that ticks me off, it is that certain voices still cannot be heard, and I believe that with the fortune and responsibility in the voice that I have, I want to do everything I can to amplify those voices. But more work has to be done.

I saw that you started a newsletter recently, for Asian­ Americans in tech.

You noticed that. I guess that I woke up one weekend realizing that, “Hey, I’m Asian.” It was this weird moment that came to me. I mean, as an Asian American, I try to hide. I try to fit in, and that’s been my whole life. I’ve always fought for everyone’s cause whether it’s African Americans, Latin Americans, LGBTQ, and any group feeling social injustice at unfair scales. Anyone. Because I know what it’s like to feel different, but I realized recently that I don’t do anything for Asian people, and it was just this, “Why don’t I?” It’s because I don’t want to people to pay attention to the fact that I am not like them. I realized what a disservice I was doing. When I saw Tracy Chou, ­she’s amazing – I felt I had to do something.

She’s in my project!

She’s like Legolas. She’s  like Legolas with the arrows in how deeply she is engaged in these matters. She made me think, “Wow, I’ve got to get off my butt and say something.” That’s why I wrote the essay, “Did I grow up and become the yellow hand?” Am I the type­-O hand on the emoji keyboard that doesn’t stand for any particular skin color or culture? I felt that maybe I should stand for something. That’s why that began. Thanks for noticing that.

I keep an eye on things [chuckles]. I’m on Twitter a lot when I’m not shooting. Let’s see, I’m curious to know your thoughts on how Silicon Valley seems to approach design.

Oh, it’s very exciting. What’s so exciting about how Silicon Valley works is that it lives in the true era that no one could have imagined, where the product is no longer five zones removed from the consumer. There is no need for the intermediary to sell the water bottle that you drink; it’s right there on the other side of the phone’s glass. You’re using the product, and not only that but it’s being used not by a few people but millions of people. So Silicon Valley designers deal with a significantly different kind of design, the design where the product is the brand, is the expression, is delivered in real time, and it can be changed every day if the budget existed. Whereas the old design is, “I’ll make these glasses, I hope they’re awesome. We shipped them; they didn’t sell. Well that’s because I was a genius and people didn’t get it.” Or, “I shipped my glasses and some sold. Hmm, okay well let’s get lucky next time.” Silicon Valley designers live in a world where the thing they’re selling is never going to be done being made, and is being shipped live. That is an amazing thing, and these design outcomes are fundamentally different than how design was done in the past. And the designers suffer at the same time too, because people who made things like in the old world got to finish it. “It’s done. It’s been finalized. It will never change now that it’s done. Isn’t it amazing? It so amazing. It’s done.” Whereas people who design in tech never get to be done. So when I saw that you were a photographer and you were taking photographs, you were able to go back to the world of “done,” because done is the best place to be. But you have both in you. You know exactly what that’s like, you know what this it is like for designers in tech. And you’re still so young, so you’ll find all these new things in your life. It’s being in this imbalanced place, that makes you a unique person in the future, I believe. That new person is part of your project. I think you’ve just started.

Thank you.

You’re like, “Oh, this is something. What is this?” Scratch head, scratch head. This is a good beginning.

This is the kind of work I’ve been wanting to do my whole life, and this is the first month that I feel like I’ve had the time and the resources to do it.

That’s good. You’ve earned it.

I do feel like I’m just at the beginning. So I appreciate the encouragement.

Absolutely.

What are your thoughts on the relationship between tech and art here?

It’s tough. In New York, it’s easy to be an artist, because there’s a lot of artists there. There’s a history of art galleries there. For example, if you’re in Paris, it’s easy to be an artist – it’s also easy to be a mathematician, I hear. Here the spirit of art is not a strong spirit, which I think signals great opportunity. And I think people, like yourself, who can seize the moment and think, “Well, maybe there isn’t a strong art community of a certain art, but maybe there’s a strong community for a different kind of art.” I think that work will be done, and that work has to be done.

Even the fact that you’re reaching out to the world and pulling people into this world that you have ­­ that’s a different kind of art. It’s like Jenny Holzer taking portraits, 80 portraits, live around the world. That feels like a kind of art that’s natural here and can be celebrated, versus old school, like “Let’s take a motor and let’s attach it to a paint can and let’s make art.” And hearing a gallery crowd cheer you on and say, “Oh, my gosh. That was amazing art. It’s right in front of me. It’s finished. It’s done.” That’s not art anymore – at least for people in the future. The new art lives with people. And I think this region would be more likely to understand that. So I’m hoping that the gallery system can evolve to accept that future. I’m sure it’s going to happen, but it’s going to be a problem for a while. If you have more of that kind of art, then the new kind of galleries will emerge, and the market will emerge from that. And I hope that you, Helena, will sell different aspects of your process as products to find that different audience and to help this region talk about art in the new language your generation will create.

One thing I’ve noticed interviewing designers, particularly designers who have worked on the East Coast and in New York city, is the frustration at a lack of philosophy in start­up design. In my experience, I remember at least, when I worked in Tech, how much technical specialization is valued versus philosophy, and I’m curious to see I you have felt any of that yourself.

Yeah. This may be a kind of blasphemy, but I used to be a member of those cults of the old world’s philosophy. I was long a part of the Swiss Typography mafia in Shinjuku. At the time, I loved the perfect movements of type by 0.001 points – where the average human being couldn’t really tell anything had changed. Invisible details, you know? I used to love that. And then I realized it was a cult, and a form of brainwashing. It was a constraining thing. It was a safe place to be, and great to have learned.

So both skills are important – the place of safety that the past provides, and the new things that can be made in the medium of technology. It’s the people who can go across the two, fluidly, that I think this region needs more of. But if you take a viewpoint of, “I know philosophy; you don’t. So you suck.” Or, “I can code; you don’t. So you suck.”

“If there were one thing that ticks me off, it is that certain voices still cannot be heard, and I believe that with the fortune and responsibility in the voice that I have, I want to do everything I can to amplify those voices. But more work has to be done.”

It’s almost like both sides are the same in that way, which is funny to think about.

That’s how sides are made. There are those who say, “I know this; you don’t know that.” Then another person nods in disbelief, “What? You don’t know that? Really? You didn’t know that?” Hmm. I’m so over that kind of thinking. I’m not into that at all. We can all learn from each other.

What are your photographs behind you? What are they?

Some are mine, some are from friends. I try not to have my own photos up there, because it feels like I’m looking at my own iMac screensaver or something.

I understand.

Or having like a portrait of yourself in your bedroom.

It’s a bit awkward, I understand.

Okay, where do I want to go now? What are you working on right now, in 2016, either for work or for yourself?

I’m working on the 2016 #DesignInTech Report ­ ­the second edition. Last year it came out at SXSW. I thought it would get 50,000 views—it had 850,000 views. So, surprise! Sheer luck. I’m like, “Woah.” I’m making the new version—that’s coming out in three weeks, so I’m sitting in front of Keynote, moving things around, and tossing things out. I hope it’s able to communicate this relationship between business, design, and tech that I care about.  I want to keep showing how it’s valuable, and that you can assign dollar signs to it: DESIGN is DE$IGN. Some people consider the dollar signs as being dirty, or just outright wrong. But I consider it work that I get to do right now. So I’m going to do it.

How is life without possessions right now? Do you feel like you’re going to stick to that for a while?

It’s been really great. I was observing how younger people live lighter lives, so I’ve been getting to live that right now. When I was at RISD, I had an 18 room mansion with six bathrooms or whatever, and I didn’t have that much stuff anyways. Now I just kind of have a suitcase and travel light, and after I broke my right arm over the winter holidays by tripping while on a run, I can’t carry as much now. So I’m even lighter now.

That’s interesting because I’ve historically been a person who gets rid of everything she owns every time she moves­­.

Interesting.

And I’ve moved a lot. And this is the first time I’ve ever put things on the wall in my apartment. It’s the first time I’ve ever had more than a Craigslist couch or a Craigslist bed. It’s really new and interesting for me and I think it’s been good for me in a way because I think I would have moved from San Francisco for reasons that don’t even make sense, like, “Things are great. Let me just completely like throw it all at the air and move somewhere else. But this have forced me to be stable for the first time in my life. So I think it might be good for me for now.

That’s the thing; you live different lives. So this part of your life is this.

Where do you see yourself in five or ten years?

Wow. I hope that I’m still involved in the start­up world. I hope I’m making a start­up, or I hope I’m at a start­up. I’ve just learned so much from the start­up generation. I figure I have to learn more by being in that world. That’s what I hope.

My last question for you would be, based on the lessons you’ve learned through your own experience or the experience of those you’ve taught, what advice would you give to young designers just getting their start in tech?

I would strongly suggest that they be curious about business because business is only scary when it’s not understood. People who are creative especially in the tech world will be looked down upon unless they are curious about business. Everyone’s got a different language. The more languages you speak, the more positive damage you can do on the world [chuckles]. So that’s my take.

“I would strongly suggest that they be curious about business because business is only scary when it’s not understood. People who are creative especially in the tech world will be looked down upon unless they are curious about business. Everyone’s got a different language. The more languages you speak, the more positive damage you can do on the world.”

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

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

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

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

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

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

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

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

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

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

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

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

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

Tell me more about that.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Where do you find your support networks?

Professionally or personally?

Both.

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

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

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

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

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

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

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

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

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

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

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

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

Totally.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Thank you.

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

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

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

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

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

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

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

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

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

[laughter]

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

1987, I was conceived, no—where I came from—as it relates to being a quote-unquote woman in technology, the origin story is probably about like this: I was a science nerd in high school. I was really into chemistry. I really liked my AP chemistry class. I was president of the science olympiad team, in Nashville, Tennessee. It was not a school that was particularly known for its academics, to be totally honest. I found my spot there.

I was born in in Fremont, California. There were a few reasons my family moved to Nashville. One of them was the chaos of being a student in the Bay Area at that time. My parents are aging hippies and they just weren’t that into exposing their kids to that level of insanity. I sort of did my own thing for high school and I seemed to turn out okay, so I appreciate that. I was a science olympiad nerd. I applied to a couple of different schools. I got into M.I.T. to study chemistry.

That’s actually my first degree, I have a Bachelor’s degree in chemistry. While I was pursuing a chemistry degree, I had a bunch of friends who were pursuing computer science degrees. I would look at them out of the corner of my eye and see what they were learning. It seemed pretty different. Compared to what I was learning it seemed like they were learning a toolkit for solving arbitrary problems in the world in a way that was really cross-disciplinary. I felt I was learning the history of chemistry in a way that could be really fun for some people, but what they were doing seemed very broadly appealing and relevant. I ended up taking a couple of CS classes. I actually sort of illicitly pursued a computer science internship without telling my chemistry advisor. He was quite unhappy with me when he found out about that. I ended up liking it a lot, and I ended up getting a bachelor’s degree in computer science as well. I got a master’s degree in computer science, and the rest is history.

That’s how I got started. I did take a couple programing classes in high school, although I wouldn’t claim that I understood the power of it then. I really started pursuing the discipline in college. I think that’s actually important to note because a lot of my friends at school had been programming since they were babies. This meant that I had a lot of catching up to do. This instilled in me a very serious and personal empathy for beginners. I also had to validate for myself that if you work hard, and if you work harder than anybody else you can catch up.

So I did that. As I got my master’s degree, I had some friends who were starting a startup called KSplice. KSplice’s story is the gift that keeps on giving, like the Silicon Valley, like the HBO show Silicon Valley has derived a number of entertaining stories from KSplice the start up. We were all computer nerds together at MIT’s computing club. They started KSplice around a technology for rebootless kernel updates on Linux. It’s like a very exciting, serious, distance program, a challenge.

“The good people and the smart people are going to treat you equally and like a human being and not like a woman in technology.”

They were a little bit older than me so when I graduated, I joined them as an early kernel engineering hire at the startup. We built it into a real business that ended up making money, being profitable. We did a bunch of goofy stuff during that time. This is like the authentic startup experience where we were working at the house where all the founders lived. It was a disaster. Dubiously zoned. We’d all have to hide when the landlord came by. There were mice everywhere. Dudes were showering with their girlfriends during the workday. All kinds of goofy stuff that has made it into various Silicon Valley episodes. It was a really good experience in learning what it means to build something from scratch.

Totally self-funded. Didn’t take any outside investment. We worked all the time, didn’t pay ourselves for a long time. That company was acquired by Oracle, and we hung out at Oracle for a little while. We left Oracle, went back to one of our apartments and continued to startup number two with the same team. Startup number two was called Zulip, it was building a real-time collaboration service for businesses. Sort of like Slack before Slack was Slack. Did the Zulip thing for a while. Zulip was acquired by Dropbox about two years ago. Now I’m at Dropbox where I’m an engineering director and a chief of staff for a VP of Engineering.

How was your experience as a female entrepreneur?

The good people and the smart people are going to treat you equally and like a human being and not like a woman in technology. The people that I was very intentionally surrounding myself with, like my peers at MIT and then my co-founders, are awesome and we work well together and we trust each other. I would take a bullet for those guys.

There was never an issue. I wasn’t the face of fundraising because my role as a founder was to run engineering organization. Our CEO and our COO were all fundraising while we were busy building the product.

The first time in the context of my professional career that I had a rude awakening about this: We had this really, really successful blog. We got really good at writing blog posts that we’d get a bunch of attention from the tech community. We knew how to get to the top of hacker news. We once made the mistake of having a blog post that included a picture of us. That is when I had the great pleasure of receiving a lot of commentary about how I looked in a blog post that was, otherwise, about engineering.

That was maybe the rudest awakening. There were also a lot of people misgendering me when talking about the author in the blog post, even though my name in Jessica. That would be a small cut in a death by a thousand papercuts situation. I don’t really try to put my face out on the internet, especially on things that are closely associated with my social media, because it’s not that fun.

I always felt really good about running a startup and the people I was surrounded by. Now at Dropbox, I am the most senior woman at the company currently. I believe I have a tremendous amount of freedom and flexibility and respect. I feel good about that, but again, I think it’s who you surround yourself with that matters. There are plenty of assholes that you could maybe end up being surrounded by, but the good people and the smart people, they know what’s up. They know what actually matters is having great people, totally respective of their gender or other qualities.

How did you end up as a technical consultant for Silicon Valley (the TV show)?

The show is this wonderful uncanny view of the valley and what’s uncomfortable about this industry. I only worked it tech for a few years, but I made it through one episode and it was like “This is too real” and I couldn’t get through. Like I said, Ksplice is really like the gift that keeps on giving. So what happened was that the Silicon Valley writers they were doing a tour of a bunch of the startups in the valley and they came to Dropbox.

Our PR team was like, “Who are some entertaining people in engineering?” and my name came up. They shoved 25 people into a conference room to ask questions. They wanted to just hear ambient stories that could be interesting and they wanted to dig in a little bit on storage, which is part of a plotline for season one.

I seized upon the opportunity to regale them with many amusing anecdotes from Ksplice. It was all kinds of goofy stuff. The service we were building is a technology for rebootless kernel updates on linux. You care about rebootless kernel on linux if you have a lot of computers and if you have a lot of computers frequently you are a hosting company or you are in the porn industry.

I just have so many stories around debugging technical issues on the computers of various companies in the porn industry, and they are just very funny. I thought that if it could tell a bunch of these goofy stories to the Silicon Valley writers and they thought I was sufficiently entertaining that they wanted to keep talking to me so we kept meeting.

They would ask me funny questions and I would tell them stories. I ended up becoming a senior technical consultant, which is important because James Cowling, who is another person from Dropbox, who is a technical consultant for the show, he’s just a technical consultant. So my name is in every credits and his is only in the episodes he directly contributed to.

That was fun and we- James and I together- helped design their little data center from season two. They invited us to the taping for scene one of episode one of season two, which is filmed at AT&T Park. They had all the celebs out, the Winklevoss were there. Drew and Raj made the cameos in their goofy stuff. It was fun to watch the behind the scenes take on how this stuff gets made. It was fun.

I love it. Let’s go into some of the other things. Aside from your job at Dropbox, you do a lot of work on improving diversity and inclusive culture at work and in the Python community. Tell me more.

I started using Python in school. It is one of the primary languages that many IT classes are taught in. I used Python in all my internships. I’ve actually used Python in every job I’ve ever had.

My first ever contribution to an open source project was while I was an intern at VM Ware. I was using this library called Twisted, which is a Python library for event-driven networking in Python. I had noticed that some of the documentation was confusing, and I thought that this might be an opportunity to contribute back to an open source project. I heard that was a thing that you could do. It seemed scary, but maybe I could figure it out.

I decided I was going to do it, but I was super nervous about it. I quadruple-checked all of the new contributor guidelines for this incredibly simple documentation badge. I agonized over the ticket creation, the title of the ticket, and the body of the ticket, and hovered my mouse over the submit button for multiple minutes, and it was like, “Someone is going to yell at me. This is going to be terrible.” I finally hit the submit button, and then, they’re like, the nicest people.

Glyph, who is one of the creators at Twisted, who is now a good friend of mine, personally helped me through getting this first patch applied. He is super patient and helpful and nice. He is not at all intimidating, even though he’s the creator of the project, and had every reason to not help me. Despite being incredibly nervous, I had this super, super positive first experience with open source contribution, which is not what most experience.

Anecdotally, that is not a typical. I think it ended up being good for Twisted, because I ended up contributing a lot more to the project. I ended up becoming a core maintainer for the project and writing a book on Twisted with O’Reilly. I really invested in the community over the years after that initial contribution. It also made me very aware of the fact that this is not an experience that everyone necessarily has. It made me very committed to wanting other people to have that experience as well. That has become my personal direction open source.

That was happening and then in sort of a parallel work stream there was this program that was happening on the West Coast while I was still in Boston as a student. It is called RailsBridge, which is like one of the earlier efforts in this wave of diversity outreach, to get more women into the Ruby/Ruby and Rails community.

I got to talking with Ashish Leroya, a friend who is also an open source nerd too, about doing something like this in Boston. We didn’t know Ruby. We knew Python. We thought, “What if we just do this in the Python community?” So we hooked up with the Boston Python user group and convinced and Ned Batchelder.

We convinced this guy Ned, one of the long time organizers of Boston Python, to let us run an intro to Python workshop, specifically for women in Boston, under the Boston Python User Group. It was sort of a bold thing to do because I didn’t really know who we were. Getting the right messaging out can be a little tricky, but he was game for it. We ended up selling out, basically, immediately. It was free, but it ended up filling up immediately.

We ended up running a bunch of these. I became an organizer for the Boston Python User Group. Then the Boston Python User Group, in large part due to these types of initiatives and other very intentional initiatives around providing a more inclusive user group for people of various backgrounds.

“As it turns out, if you make an effort to be welcoming to one set of people, you will probably actually become more welcoming to everybody, which is the secret to all diversity, everybody just actually helps everyone.”

Boston is a great testing ground for this, because it has a very high density tech population. It is adjacent to a bunch of other stuff, like bio-tech, a lot of entrepreneurs, music is very big—so there are a bunch of adjacent fields that leverage programming that you can tap into if you do a good job of being welcoming.

We ran a bunch of these diversity outreach workshops, and then a bunch of crazy statistics occurred. We set out a goal – it’s as true in my day job as in these open source communities – like you set a goal and then you measure it to know if you’re like actually doing what you intended to do. We had this goal around increasing the representation of women at user group events. We started at nearly 0% at user group events for women, wanting to boost that to 15%. We instantly achieved that by running these intro workshops and some follow-up events. It really became a pipeline of events.

Then we were able to sustain that participation rate for several years. I’d have to check in with Ned about what the latest stats are, but while I was there in Boston, this represented a huge leap in the actual composition of the user group but also the way that it felt. It became a real poster-child/example set of processes that were adopted by user groups around the United States and globally. We gave a talk about this at PyCon, and it’s been replicated like all over the world, which is pretty amazing.

So I was an organizer for the Boston part of the user group, which is part of this initiative, became the largest user group in the world. As it turns out, if you make an effort to be welcoming to one set of people, you will probably actually become more welcoming to everybody, which is the secret to all diversity, everybody just actually helps everyone.

I then ran for and then became a director for the Python Software Foundation, which the non-profit and stewarding organization behind the Python programming language and community. I served as a director for a couple of years and I was also a co-chair for our Outreach and Education Committee, which provided a lot of funding to educational initiatives. They use Python.

For the last three years I’ve been the diversity chair for Python. There are many Python conferences around the world. Python is the original big international conference that’s held in North America somewhere once a year. I’ve been the diversity chair for the past three years, so in the three years I’ve always had that role formally.

There’s a pretty sick set of statistics about this. If you look in the old Twitter feed, like three years prior to me having this role, the percentage of speakers at Python who were women was one percent, and then it was 5%, and then it was 10%. When formalized, and I was investing time in and getting other people to invest time in, it was 15 %, and then it was 33%. By the time this project launches, that number will increase to 41%, which is insanely high for a very prestigious open source conference. This is a conference with a highly competitive and actually mostly blind selection process, so this is a pure top of the funnel investment with real payoff.

You’ve engineered a system that was successful in increasing diversity in this specific culture. What are the things that have worked and what are the roadblocks that you see that make it tougher to replicate across all tech?

I should caveat the whole prior discussion with the fact that gender is not the only demographic that matters. Gender happens to be relatively easy to measure, in a way that’s not super creepy, and track over time. Women are half the population. It’s a very obvious needle to move. Let’s pretend that we wish there were more women in engineering in our company. It can be women, or it can be any other demographic that you’re trying to optimize for. Here’s the process:

Step zero: it has to actually be a place where people want to work. For example, it has to be a place that equitably retains and promotes women. There’s no point worrying about and investing a bunch of time in the hiring process if once people join, there they’re going to be unhappy and they’re going to quit. That’s step zero. You have to measure this stuff or you won’t know if you’re doing a good job. Do that.

Step one: You have to have an equitable evaluation pipeline.You’re the only one who’s measuring it, so you need to measure segments broken down by the demographics that you care about. If your evaluation process is fair, and has equitable outcomes, this will stabilize across the demographics that you care about. There’s a standard pipeline analysis for this, which is like your pre-onset to onset, and your onset to offer, offer to offer accept. You have to ensure that whole process is equitable.

“If all it is a math problem, what it really is, then is just a prioritization question because anybody can do the math. It’s a question for you as the head of a company, what is the appropriate way to prioritize this problem? If your company is running out of money tomorrow and has a bunch of other problems, maybe this isn’t the thing that you need to be paying attention too. But I suspect if you want to be a company that’s around for the long haul and you want to attract the best talents and retain it, you probably have to care about this whether you like it or not because people like me are going to opt out of working at your company if you don’t make it a priority.”

The beauty of this is that when you achieve steps zero and one, it becomes a numbers game. You have to pass through raids on an evaluation pipeline that is equitable and dumps candidates into an environment that is equitable, all you have to do then is have some outcomes that you want, back up the math on that and that’s a set of top of funnel targets that your job. Your job is to incentivize a diverse top of the funnel that will cause the math to happen from the pipeline that has those outcomes. That’s all it is. It is just a math problem.

If all it is a math problem, what it really is, then is just a prioritization question because anybody can do the math. It’s a question for you as the head of a company, what is the appropriate way to prioritize this problem? If your company is running out of money tomorrow and has a bunch of other problems, maybe this isn’t the thing that you need to be paying attention too. But I suspect if you want to be a company that’s around for the long haul and you want to attract the best talents and retain it, you probably have to care about this whether you like it or not because people like me are going to opt out of working at your company if you don’t make it a priority.

Then, it’s a prioritization question, so you make sure that it’s staffed appropriately with recruiting and with event coordinators and it’s incentivized appropriately with your hiring managers and with recruiting. Then you just do it. Any company that says that they care about this, in particular, if you’re going to write a blog post about it or something where you’re going to say that you care about it and then you report back next year that nothing has changed, you don’t have to make up a crazy story about it. You just didn’t prioritize it sufficiently. Just own that. It’s your decision to make and you can evaluate the pros and cons, but that’s all it is. It was a prioritization decision. Once you have an inclusive culture, it will make for an equitable pipeline and a properly incentivized top of the funnel and that’s all there is to it. So, simple, right? How do people screw this up?

Well, it’s funny hearing just the very first step and making it—even just for tension it’s just starting to be talked about. It’s crazy.

If that sounded depressing, the good news is that I think that it has become something that people have to care about and it will just naturally become a thing that accompanies our better add over time. Enough people are going to be doing this. Kids these days who are going to  graduated from college soon. They’re going to enter into a work force, or they’re not even going to realize that it used to be difficult to get engineering teams to talk about why this was a thing they should care about. It’s a different scene these days. That’s extremely encouraging. We should be vigilant about this stuff. It’s easy to regress, but I’m pretty optimistic.

Do you feel the inclination to apply your knowledge, and what you’ve learned, and your experience, into different specific niches of tech after this? After Python?

That question is, what do I actually care about in life, which is a totally different question, although we could talk about that, if you want.

We can talk about that.

I am not strongly motivated by being in an engineering leadership position at a tech company. I appear to be pretty good at it, which is why I keep doing it, and then keep getting into increasingly large levels of responsibility for it. I really like people. I really like surrounding myself with the types of people that you find  in these organizations. There are other things that I actually care about in life and I would expect that in the arch of my adult life and I will move into a pretty different role over time.

Things that I care about include—they’re going to all sound related. Things that I care about include the democratic machine, like democracy as an institution mostly in the United States. I care about education. I care about journalism. And then I care about the power of media more broadly to educate and influence people. These things are all related. You need an aware and educated population that is able to work together in a democratic society to move each other forward. That’s how it’s all related.

All of these things, one property that’s really nice about being in a software company or being in software, is the scale. You can write software that you continually distribute to everybody, to hundreds of millions of people if you want. That is incredibly powerful and once you have a taste of doing that, it can be difficult to do work that scales less. For example, it is difficult to visualize myself being a teacher in a classroom. Maybe if I’m a teacher in a classroom that is on the  internet and reaches lots and lots of people, maybe that’s appealing. Or if I’m helping to drive policy decisions that impact many, many people, that’s appealing. It’s finding the impact at scale in these fields that I’m pretty passionate about in a way that parallels the opportunities scale that you can have in software. Those are things I actually care about.

Why have you been working in tech companies and for a while if it’s not really what you care about?

I’ve learned that it’s been intentional. I’ve learned a bunch of highly transferable skills building companies and managing increasingly complex organizations.I wouldn’t go back and undo it. I will eventually, over the course of my life, move into something that’s more differently related to one of these four topics that I mentioned. A change from holding a leadership position in a pure tech company.

On that note, I’m curious about your high-level thoughts on the state of tech in 2016, and what excites you, specifically the potential of tech’s applications to those things that you care about.

It’s a good question. I mean some of these things are a little obvious, and if I were better predicting the non-obvious things, like maybe I should be a VC and just cash a bunch of checks, ha!

I’m a pretty avid Twitter user.  When I watch grassroots political movements on Twitter that’s exciting to me. The internet is amazing. It connects people independent of distance. That’s why the internet is the greatest invention of all time, and I’m a little bit obsessed with it. There is also the infrastructure of the internet, we could go off on a whole weird tangent about that. That’s exciting.

To follow up on that, that was a lot of the stuff that I think is the biggest set of issues isn’t going to get solved. Sometimes the solution isn’t technological. There will be technological platforms that will enable the people who are going to cause the change to do it, but at the end of the day the thing that’s going to make a difference. Problems like fulfilling the promise of a equitable  public education in the U.S. is not going to be solved by technology. I don’t think it is—I could be wrong. Sorry to any ed-tech people who end up reading this.

I don’t think like a piece of software is going to solve that problem. It’s going to be the policies and the institutional infrastructure around people that we change that solves it. Which is part of why I probably won’t be building the software for very long. I’m going to be more directly in the sector with the people who are making the change. Probably.

Do you have feelings about technology influencing the rate at which policy can be changed?

You would hope that it makes it faster. If you could vote from your phone, or a computer, that’d be pretty great. The place that I just was before I was here, I was just in Buenos Aires, and they have compulsory voting. Because you have a bunch of people who vote because they have to, and they don’t know what’s going on. There are pros and cons to compulsory voting. It’s too bad that the engagement is so low in the U.S., but if we could make it easier to vote, that’d be pretty sweet. Although in this election, I think that we’re going to have better turnout than ever before. It’s a crazy time.

What is frustrating to you about tech in its current state, and what would you like to see change?

I think it’s bad that in the US there is a monopoly on this sort of startup ecosystem and culture. Really the only game in town is Silicon Valley, and I’m sort of a walking example of this. I was in Boston, started two tech companies in Boston and even we succumbed to the pull of Silicon Valley.

It’s because money is better out here. The tech companies who are going to acquire you are going to pay bigger premiums out west. The talent’s all out here. The network is out here. And that’s bad. What do we learn in history about monopolies? Like, monopolies are—in the long run they’re bad for innovation.

I would love to see truly competitive alternative to Silicon Valley in the United States. I would love to see competition that it’s a healthier culture, and maybe promotes people being willing to invest in ideas deeply, for a long time. Really bringing expertise in a domain to solving real problems in the world, as opposed to just building apps. That is my fantasy is that 20 years from now.

From all of your experiences, having not worked only in Silicon Valley proper, being a female developer, doing tons of diversity work, I would just be curious to hear your general thoughts right now on the state of diversity in tech. Aside from the system that can fix it, or even the high-level roadblocks you’ve seen.

If you look at the research, the data tells us that there’s a leaky pipeline and that diversity for women in industry as compared to graduation rates is still trailing behind and it’s a much worse story for other demographics. If we wanted to pick on ethnic demographics, the story for African-Americans and Hispanics is much worse. That sucks! I don’t want to be in a different industry though.  

Why do we even care that the tech industry be reflective of the population that it serves? It has such a profound ability to change people’s lives if we do it the right way. I personally wouldn’t want to leave because of the shitty pipeline issues that I’d rather fight, but not everybody has the luxury of being able to do that. I mean, the trends are weird, right? The trends for women in CS were going down for a really long time. My understanding is that they’re back on the upswing, but the peak was decades ago, and we have a lot of ground to recover. I feel like there’s a lot of work to do, but that’s work worth doing.

I keep going back to the story you shared of having such a positive first experience in shipping that patch to the open source project. I wonder how massively important those first experiences are, and whether they’re positive or negative.

Hugely.

—and whether or not that turns a person into a incredibly high contributor vs someone who eventually leaves the industry.

Anyone in data tells us that it’s usually important. It doesn’t even have to be anecdotal, I think we just know from the data.

This is related to some of the things we’ve talked about, but it’s worth saying. I get asked quite a bit why I spend a bunch of time on outreach in Tech, and the real actual reason for this is different from what people would expect. I believe we will build better products if the people who are developing these products are a  reflection of the population that we are serving.

It’s the right thing to do. I want any kids that I have to feel like they can do anything in the world. Those are all the reasons why, and I believe that it is important that people have access to programing.

“Learning how to program allows you to develop the confidence that you can learn how to operate within a system and to deconstruct it and to tear it down to make it better.”

Not everybody has to be a programmer but let them always have the opportunity to try it out. It is the first time that you can become fluent in a system, so that you understand that you can change it and that lesson that everything in the world is a system that can be understood and deconstructed and changed in that way. I think many people probably never have had the luxury to navel gaze about this stuff. Learning how to program allows you to develop the confidence that you can learn how to operate within a system and to deconstruct it and to tear it down to make it better.

Knowing how to do that and have confidence in that as a programmer is already very powerful because when you know how to program you can create all of these amazing things in the world. The more important lesson there is that you have gained—you have had this experience of observing a system and believing that you can change it. And that’s the thing that I actually want everybody on the planet to experience because there are many systems, and some of these systems are software systems, but probably the most important ones are people systems, and it’s not actually any different.

“Everything is a system that you can understand, and you can deconstruct, and you can break down, and you can change.”

Everything is a system that you can understand, and you can deconstruct, and you can break down, and you can change. That is the thing that I actually want everybody to experience. That is why I spend all of my time—or a bunch of time—teaching beginners of diverse backgrounds how to program, because that is maybe the most profound thing that I’ve ever experienced, and maybe one of the more profound things that many, many people in the world can experience if they have a chance to do so.

What advice would you give to folks who hope to get into programming or are just getting started?

I’m a lot more confident now than when I was when I was 18.I don’t know if there’s a way to short circuit that. I don’t know if there’s a world where anybody can tell you like believe in yourself, have the confidence. I don’t know if there’s any way to learn that through experience but it makes such a big difference. Given my experiences in college, feeling like I had to work harder than all of my peers who’d been doing this for a lot longer than me, and later to get to the point where I could prove myself to them and validate that I was as good as everyone else like a big validation.

By having the confidence to dive into that and to totally believe people actually thought I was good wasn’t simple. It was like an imposter syndrome. The side issue I want you to learn about is imposter syndrome. It actually makes material impact in your life. This is one of those beautiful things that you realize that if you put into it you could reflect on it could actually change your behavior. I think that’s how I would summarize it. If I had known about it when I was 16 or 18, that would have been helpful.

Sure. I’m from the St. Louis, Missouri area. Technically I’m from southern Illinois, but when I say Illinois, people think Chicago, which is like six hours north of Shiloh, Illinois, where I’m from. I lived there from kindergarten until I graduated from high school.

I was always a shy kid—soft spoken, quiet, very much a bookworm. I was also into video games from an early age thanks to my dad’s influence. I also really liked the internet because it was this new, shiny thing. In Belleville, most people are like-minded—so because the Internet has so many subcultures,  I felt like I could finally find my place. I eventually taught myself how to code, HTML and CSS to start, and how to create graphics. I made random websites based on stuff I was interested in; I think I made my first website in 6th grade. It was on Geocities [laughter]. I kept doing it throughout high school and it morphed into my passion.

After high school, I went to a small school called Maryville University in St. Louis, thinking like, “I’m going to be a web designer for a living, that’s a thing people do I guess?” But my school didn’t actually have much for web design. I told them I wanted to major in web design, but they’re like “uh, we don’t have that, what are you talking about?” They did have very small graphic design program, so I decided to major in that.

“The summer before my sophomore year, my dad got laid off so my parents couldn’t help me with school anymore. I had a decent scholarship based on my strong academics from high school, but my university was so expensive that I couldn’t afford the rest of the tuition. The school wouldn’t let me continue until I paid back what owed from my freshman year, so I left school and got two jobs: first at Build a Bear and the Apple Store, and then Apple and a waitressing job.”

The summer before my sophomore year, my dad got laid off so my parents couldn’t help me with school anymore. I had a decent scholarship based on my strong academics from high school, but my university was so expensive that I couldn’t afford the rest of the tuition. The school wouldn’t let me continue until I paid back what owed from my freshman year, so I left school and got two jobs: first at Build a Bear and the Apple Store, and then Apple and a waitressing job. I was thinking, “well, I’ll work on paying them back and just figure it out as I go.” After about 2 years of working while taking a few community college classes, I finally paid back the freshman year debt. But by then I was so disillusioned with Maryville University and the Midwest in general that I was like, “well, I’m moving to California now.” So I went online and searched for design programs in California.

I found a school in San Francisco and I got interested in their animation program. Suddenly I was like “well now I’m going to be an animator.” So I saved up, transferred Apple stores, and moved to San Francisco to attend the Art Institute of California (AI). Eventually I figured out that animation wasn’t a great fit for me. I love to watch animation, but I didn’t enjoy the process of making it and the school was extremely expensive. But by that point I was already kind of in love with San Francisco. I’d been here about a year, so I was like, well I may not be going to school there anymore, but I have to figure out how I can stay here. So I left AI, then I went on Craigslist and found a second job, working as an office assistant at a startup called Socialcast in SOMA. I  eventually let them know I was into design and that I could code, so they allowed me to take on some small projects for the company while I worked as an office assistant. When my boss went on maternity leave, I quit my job at Apple and went to Socialcast full time, which kind of started me on this tech path.

“Learning how to code was very tedious for me [chuckles]. I had to follow so many tutorials. I also feel like I’m always comparing myself to developers I meet here who are extremely talented. Sometimes I don’t even want to call myself a coder or developer compared to them. I’m a designer who can code. That’s an important distinction to me.”

What was the experience like for you, teaching yourself to design and code?

It partially goes on instinct. I’ve always be attracted to visual endeavors; I’ve been drawing, painting, and things like that since I was in junior high. So I feel like design is very similar to where it really helps if you some natural instinct for things like handling visuals and being empathetic to users, but there are also many things you have to be taught. As for coding, there’s more effort involved for me. I enjoy it, but I sometimes struggle with the logic behind it. Learning how to code was very tedious for me [chuckles]. I had to follow so many tutorials. I also feel like I’m always comparing myself to developers I meet here who are extremely talented. Sometimes I don’t even want to call myself a coder or developer compared to them. I’m a designer who can code. That’s an important distinction to me. Learning how to code was challenging, but learning how to design has been fun because it’s about reading people’s emotions, designing interactions and visuals, and things like that. And I am always learning. I’ve never had a full formal design education. It’s mostly been on the job experience. Since that’s something I’m aware of, I always try to keep reading and learning.

Tell me a little bit more about your work and things that you’re proud of—things that really excite you about your work.

One thing I’m a big advocate for in my work is thinking outside the typical mold that tech people in Silicon valley seem to be designing for. Even in the most subtle ways, so many people are designing for users who are in demographics that are similar to themselves or other people in their “bubble.” By default, they are designing for someone who looks like them. And most designers in San Francisco are white guys, with some white girls mixed in here and there. So I’m often the person chiming in with things like “Wait why do all of the avatars have that kind of hair? Not everyone has that texture. Why are all the hands holding the mobile devices in these photo white” And I know details like that are such a non-issue for some people, but because I notice it I like to challenge other designers on it when I can. Lately I’m reading up on things like how to design for those with disabilities, like design for people with hearing or visual disabilities. So that’s kind of the thing I really get excited about, just thinking about audiences that aren’t as focused on.

“One thing I’m a big advocate for in my work is thinking outside the typical mold that tech people in Silicon valley seem to be designing for. Even in the most subtle ways, so many people are designing for users who are in demographics that are similar to themselves or other people in their “bubble.” By default, they are designing for someone who looks like them.”

What were your first impressions of Silicon Valley?

I didn’t really have a strong impression of it before moving here. I think I saw a movie when I was in junior high, Pirates of Silicon Valley? I really never saw myself having anything to do with it—I didn’t correlate my nerdy hobbies like web design to be related to tech. And then when I got the job at Socialcast, it was still all so new to me. There were only like 10 to 15 people in the office at the time, and I didn’t even know what a startup was. I was coming in thinking like, “Ok, I need something that’s going to pay my bills—that’s all I care about.” But when I got hired they were starting a round of funding, so I was being thrown into this fast paced startup world. And at the same time, I was still working part time at the Apple Store. So it was very different, being an hourly retail employee going into a startup world. I had no idea of what to expect but what I learned very quickly is there’s a lot of really smart people working really hard on something, and everyone’s really passionate. So that was kind of cool because that’s the kind of work ethic that I personally admire. So I was like, “Okay, so much is happening here.” So I didn’t know what I was witnessing when I first moved here, and in retrospect I’m like, “Man, I should have met more people and networked and all that!” But also, I’m terrible at networking, but it was still cool though to be a part of it.

“I would definitely say a sense of isolation. It’s a little due to my own personal insecurities because I haven’t finished school, but on top of that, it’s hard when no one looks like you or can relate to struggles you may have.”

What have been some of the tougher parts about working in tech for you?

I would definitely say a sense of isolation. It’s a little due to my own personal insecurities because I haven’t finished school, but on top of that, it’s hard when no one looks like you or can relate to struggles you may have. It’s been a challenge for me lately, especially now that I’m getting older and really wanting to explore and embrace my ethnicity. I actually did a 23andme genealogy test like two years ago to learn about my heritage and ethnicity because there’s a lot of holes in my family tree and I just had this feeling of wanting to define who I am, ethnically. Lately I’m feeling much more aware of what it means to be a Black woman than I have been ever before. I’m finally confident in proudly declaring that I’m a Black woman, but I work in an industry where I feel like I can’t let that pride be known because I don’t want to make a lot of people uncomfortable. So it’s kind of like a weird double act where outside of work, I feel very “woke” or aware of social justice and civil rights issues affecting Black Americans and other minority groups, but then at work that side of me never comes out because I’m scared that it’s not appropriate. And then I feel so frustrated that I’m even having this internal struggle where I’m so concerned about making other people uncomfortable.

“Lately I’m feeling much more aware of what it means to be a Black woman than I have been ever before. I’m finally confident in proudly declaring that I’m a Black woman, but I work in an industry where I feel like I can’t let that pride be known because I don’t want to make a lot of people uncomfortable. So it’s kind of like a weird double act where outside of work, I feel very “woke” or aware of social justice and civil rights issues affecting Black Americans and other minority groups, but then at work that side of me never comes out because I’m scared that it’s not appropriate. And then I feel so frustrated that I’m even having this internal struggle where I’m so concerned about making other people uncomfortable.”

It doesn’t help that I have had these awkward conversations where people just don’t know or care that I identify as Black so they feel comfortable saying really ridiculous or ignorant things. Like once I was in Lyft and the driver talking about Ferguson because I mentioned I’m from St. Louis. It was right around the protests that happened after Mike Brown was shot and he was totally ragging on protesters, and just being very insulting and condescending to the community as a whole. I remember thinking “Wow, would he say all of that to me if I had visibly darker skin?” Would he be comfortable saying, “These people are rioting like animals”’ or whatever he said. I think the answer is no, he wouldn’t have.

And so that’s the worry I have—although someone may seem like a great person overall, they’ll have some beliefs may be really different than mine when it comes down to it and I don’t want to cause problems at work or networking as a result. I don’t want to make people feel uncomfortable or exclude them from my life due to difference of opinion, but to me there are some ways of thinking that I can’t accept because they actively hurt people. So I end up compromising my beliefs and tolerating things that I know I shouldn’t. In the past, I would just nervously laugh along with jokes and smile when on the inside I don’t agree. Lately, in the last year or so, I’m trying harder to tactfully call people out, but it’s quite hard to do sometimes.

“I don’t want to make people feel uncomfortable or exclude them from my life due to difference of opinion, but to me there are some ways of thinking that I can’t accept because they actively hurt people. So I end up compromising my beliefs and tolerating things that I know I shouldn’t. In the past, I would just nervously laugh along with jokes and smile when on the inside I don’t agree. Lately, in the last year or so, I’m trying harder to tactfully call people out, but it’s quite hard to do sometimes.”

One star for that driver.

Yeah, but, ugh, that’s one thing I’m so embarrassed about to this day! I didn’t even rate him badly. I just was like, “Oh, he was really nice before we talked about Ferguson, and he obviously has no idea what he was talking about.” I still gave him 5 stars. I basically give everyone a 5 star, but after that, it haunted me for weeks. I feel like Tiffany today would not have been so meek, but back then I was still so mousy about issues of race and politics. I just didn’t want to talk about it, because ignoring microaggressions is what has helped me thrive in college and in my career.

And I don’t want to sound like I think I some perfect person who gets it right each time. Honestly, in the past I used to think most race issues didn’t affect me. But because I have a younger brother, I see him in all of these young black and brown men being targeted by police brutality or the justice system. So that helped wake me up, because my family isn’t totally protected from the effects of institutional racism just because we have lighter skin. It could happen to me too. And at the same time, me finally realizing that social justice issues directly affect me or those I care about shouldn’t have been what made me finally pay attention to systematic inequalities. So now I occasionally feel guilty for judging people who are ignorant about civil rights issues because I was still quite naive seven years ago when I first moved here.

“Honestly, in the past I used to think most race issues didn’t affect me. But because I have a younger brother, I see him in all of these young black and brown men being targeted by police brutality or the justice system. So that helped wake me up, because my family isn’t totally protected from the effects of institutional racism just because we have lighter skin. It could happen to me too.”

But I think most people, even the naive, now know that something is going with the race relations in this country. It’s good. I feel like it all of of this racial tension needs to come up to the surface so people can talk about it. While we may never be able to end racism, we can start acknowledging and addressing the systemic issues and begin to move forward. Because I think when Barack Obama got elected, people were like, “Well, racism is over!” I don’t think that’s been quite the case [chuckles]. It’s been a very weird thing to witness on the activism I’m seeing online and offline elsewhere versus what I’m witnessing in my real life.

Yeah, it’s so interesting. Have you found support networks here yet?

I have, and I haven’t. I follow lots of different social justice accounts on Tumblr and Twitter, where people can share their own personal stories or report on different situations happening across the globe. It’s nice to find a connection through other people’s experiences.

The one support group I have found that is local is online, a Bay Area “Women of Color in Tech” group. It’s nice to have a place where other women of color will listen to my concerns and validate my feelings. So I have found a support group in that sense, but I haven’t actually made any friends in the group.

I have friends in the Bay Area that are designers of course—other women designers and other women of color designers—mostly Asian women. And while I’m sure we could discuss the hardships of being a woman in tech, I don’t think I could approach them about issues concerning race or anti-blackness. I don’t know if they will feel comfortable talking about it, and honestly I also don’t know how much they would care. I don’t think I’d find any support in my professional network. So that’s something I do think is missing, that solidarity.

“The Bay Area is more diverse overall than my hometown, but seeing black and brown faces is so rare in tech. One of my friends from grade school had a work trip here recently, we met to catch up and talk about work and life in general. It was so nice just vibing with her. Because I hadn’t done that ever, really— talking about professional issues as a black woman with another black woman. She isn’t a designer—she works in economics. But it was still nice to have that moment.”

The Bay Area is more diverse overall than my hometown, but seeing black and brown faces is so rare in tech. One of my friends from grade school had a work trip here recently, we met to catch up and talk about work and life in general. It was so nice just vibing with her. Because I hadn’t done that ever, really— talking about professional issues as a black woman with another black woman. She isn’t a designer—she works in economics. But it was still nice to have that moment. I wish I could discuss social justice issues more and talk about these things openly, instead of me being complacent and pretending that race isn’t the issue. Unless I’m on Tumblr, and then I feel okay publicly acknowledging that it’s an issue [chuckles].

Yeah. You mentioned in your pre-interview that you hadn’t met another black woman designer in your six years here in tech?

Yeah. I feel like I’ve met maybe one or two in passing, but I’ve definitely never worked with or had a friendship with another black woman designer. Obviously I don’t want to be friends with someone just because we have a similar ethnic background—that’s shallow. But it does make me sad to knowing I have no black designer friends—male or female. That’s weird to me. I know there’s black women designers out there. There has to be. But where are they? If there are no black women designing the apps and sites that so many people use, then that voice isn’t being presented or considered in the design. Are things being designed with black women in mind? Or Latina or Hispanic women? I don’t know. I don’t think so.

Do you feel like you have role models that you can look up to?

I don’t have any black woman designers, but I do have other female designers as role models, for sure. Actually, one of my personal designer role models is one of my really good friends. She’s an amazing designer and an even better person. She’s also a woman of color too. I used to work with her at my last job. Once she left, I realized how wonderful it is to have a friend and mentor at work. Not only does she mentor me in design, but I’ve learned so much from her about workplace politics. I’ve witnessed people discriminate against her. I don’t know how much of it was race related, perhaps some of it was, but working with her I saw what it looks like when men are threatened by strong women. Confident and smart women taking taking leadership positions threatens some men, and I witnessed that happen. And it was unfortunate, but she handled it with such grace, elegance, and perseverance. I’m glad that I have someone that I can turn to not only for career and design advice, but also for help in navigating the realities of being a minority and a woman in the design world. She’s definitely someone I can go to when I feel like I’m lost.

You touched on this and you mentioned in your pre-interview that you’ve had some really unique experiences as a pale black person.

Sometimes I think that non-black people don’t really know what I am, which used to actually really surprise me. I never thought of myself as being racially ambiguous until I got to college. My school wasn’t diverse and I started getting the “what are you?” questions. Right now I have braids, I think maybe that helps. People are like “oh ok, well, she’s something…” but when I first moved here I used to straighten my hair. A common question I get is if I am part Japanese, which is amusing to me because I have 0% East Asian genetics. I just happen to love studying the language.

But from time to time, I’ll hear comments from people or they do things like casually quote a song and use the n-word, I’m just like “whoa, would you have been as comfortable saying that if I had darker skin?” I don’t think they would. Like you wouldn’t have said that if I had the same skin tone as my dad, who matches the visible spectrum of what non-black people perceive as being black. So I think sometimes people feel like more comfortable saying things that are not appropriate around me, but on the flip side I think that it’s kind of up to me to say something. But that’s also much pressure! I’m naturally not a combative or antagonistic person, but even when I’ve spoken up in the past, people are like “Oh, what are you mixed with?” So it’s always really awkward. But I’ve always felt like I have had to prove my blackness. So even today, I find myself being like “Stereotypes are gross but of course I can dance, of course I can cook soul food.”

As an adult, I have wondered how many other black people think about this stuff, but I don’t have a network of people talk about it with in the Bay Area. Growing up, I really never talked about race like this. The St. Louis area is very segregated. It’s like you’re black or you’re white—even non-black people of color seemed to “pick a side,” if you will. And I liked things that black people weren’t supposed to like, like computers, video games, and anime. I took advanced classes in junior high and high school where there were only a handful of black kids, in a school that was like 50% black. And then I had this super light skin, eyes, and hair that somehow made me a target for some black kid bullies, saying I stuff like I wasn’t even an Oreo (an insult saying someone is black on the outside, white on the inside), that I was just an other.

So, by the time I started college, I was perfectly happy being like “fine, they don’t think I’m black, whatever. I’m just my own thing.” Which was so weird, because my dad is Black, and my mom is technically mixed with White but identifies as Black. So at home, I was Black but at school I felt too intimidated to say I was Black. So that’s why I think I’ve had this epiphany in the last few years where I’m like, no I am Black too. The 23andme test was like the final bit of ammo I needed. I’m 68% African. I may be mixed with other things, but that is my proof. It’s what made feel like I can claim my blackness, even though I’m on the lighter side of the spectrum of American Blackness.

“I feel like I’ve met maybe one or two in passing, but I’ve definitely never worked with or had a friendship with another black woman designer. Obviously I don’t want to be friends with someone just because we have a similar ethnic background—that’s shallow. But it does make me sad to knowing I have no black designer friends—male or female. That’s weird to me. I know there’s black women designers out there. There has to be. But where are they? If there are no black women designing the apps and sites that so many people use, then that voice isn’t being presented or considered in the design. Are things being designed with black women in mind? Or Latina or Hispanic women? I don’t know. I don’t think so.”

I know my friends and even family aren’t aware of these internal identity struggles I have. So, I know sometimes I’m more sensitive about making people accept that I am a valid form of Blackness. Which sounds really weird because at the same time if you talked to me ten years ago I would be like, “No, I’m not black. Black people don’t accept me and so I don’t accept them.”

And I know I don’t face the same level of discrimination that comes with darker skin. I also know that light skin privilege exists. I feel like I’m in a very interesting place today and definitely this is like—I’ve never even talked about this with anybody like before. I feel so comfortable discussing this with you [chuckles], but now that you asked that question, all of the feelings that I had before about how I never really felt like I could proudly say that I’m a black person. But now, I do feel like that and sometimes I’m almost like beating that fact over people’s heads because I’m finally like comfortable saying that. But, that’s only around friends. When it comes to work, I don’t really like to talk about race because like I said, I’m always worried about the reaction I’ll get.

I’ve talked a lot with people about how like the way that they grew up and how it impacts like how they are in work environments and stuff like that. For some people, it manifests in now wanting to like minimize conflict and that sort of thing. So I’m curious how like you’re upbringing you think affects like how you deal with stuff in the workplace.

I would agree with that for sure. I think people from the Midwest tend to like be really nice up front, because that’s just how you’re supposed to be—neighborly and super accommodating. And so I definitely have that quality, but even in my own home growing up, I was always the very quiet one. But that said, I feel like as I’m getting older, finding my voice, and becoming more comfortable in myself, I definitely am getting better at speaking out when I don’t like something. But I do sometimes catch people off guard when I don’t like something because I usually am so easygoing. I naturally want people to get along and want there to be harmony and balance. But when I do have to confront someone over something I have to psyche myself into it. Like I said about the Lyft driver guy, like I could have passively given him a bad review, but I still felt bad doing that. I was thinking “Oh but he has a hard job too and maybe he had a bad day.”

I have a very similar temperament. I’m just now learning to stand up for myself too—not letting everything slide.

That’s my biggest thing. I’ve always struggled with microaggressions, even before I knew what they were called. They have happened to me my whole life and I have typically just let them slide. I felt like at some point, I’d eventually reach a breaking point over it so that’s why I felt I had to get better at not letting them go. But standing up for myself—even if it’s not confronting someone in the moment—that’s my personal goal is to be able to do that.

I honestly still can’t.

It’s hard. One of my current goals is to, especially with someone I care about, is to call them out on it if they say something that isn’t cool. For all scenarios, even when it’s not something that directly relates to me. Especially in work situations, where I’m like, “I’m cool with you and we’re friends, but you can’t say that kind of stuff about women or make jokes about someone’s body or sexuality or anything like that.” Being in the Bay Area, sometimes I feel like I’m working with a lot of immature man children. Like a designer I worked with compared an Asian interview subject, specifically her voice and laugh, to a yellowface character from a sketch tv show. This was during an interview round table session, in front of other senior people and the recruiter. No one said anything. Like, he was a senior team member and he was openly making jokes like that. I wish I had said something, you know? When I think back to stuff like that I always feel a kind of pang of regret, like “I should have said something.”

Based on all of your experiences, what would you look for in a future job?

That’s something I’m thinking about a lot now. I have separate buckets of criteria for what I’m looking for in future roles. Like is it a job where the product is  making a difference in people’s lives, helping somehow? Is it a job where I am being fulfilled personally? Is the team diverse? So far, the jobs I’ve had have been really good for personal growth and career growth, but they haven’t matched the other criteria as much. And for the second criteria bucket, for a future job I definitely would love to do something related to like my hobbies or interests. Like I have been studying Japanese for almost a decade now. So I would love to do something with Japanese in my career so it feels like it’s not just a hobby and something that I’m actually using everyday.

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

I think what’s really exciting is that the things we work on in tech are so normal for everyone, even those outside of the tech world now. Actually, I just got back from Bahrain last week. My friend is from there and I went for her wedding. In Bahrain, Instagram was everywhere. And it was so crazy think that this product that was originally created by a small team in the same city where I live is touching so many people’s lives across the world. Like storefronts had their Instagram names on the sign below the store’s name, like that’s how big it is there.

But what scares or frustrates me is like stuff like bullying, or how tech can give hatred such a prominent platform.

“Diversity and inclusion just isn’t a concern for most people in tech. For example, if you’re happy and comfortable with your design team being homogenous, then you’re probably not going to feel challenged to make it diverse unless somebody points out, ‘Hey, this is a problem.'”

Also, it seems that now people are getting so hung up on online relationships that they don’t know how to have offline relationships anymore. I just watched Master of None and all those things he’s talking about are things that I am witnessing friends go through. Like people don’t know how to have relationships. They’re so worried because there’s like 5,000 people they can date via an app. They don’t want to settle and things like that. So that kind of scares me… And I’m a technology optimist.

A lot of people are scared of the Big Brotherness Google a lot, but I’m the person who’s like, “Google, take my data. You help me get to meetings on time; you help me not get lost. You can have all my data.” But I’m always a little worried that the era of optimism and innocence with the Internet is gone. People are more nefarious and don’t have the best intentions with your data out there. So that’s another thing I think is really big for tech right now is security. Now that the internet is more mature, we’re starting to really see more standards now. From a product development standpoint, maybe you can’t move fast and break things—to quote Facebook—but now users are more aware about their data. So you have to spend more time making sure your product is safe and compliant. So I think it’s nice that we are self-regulating things, but I don’t want tech to get too regulated. The Internet has always been a special place with unlimited creativity. Overall, tech is very exciting right now. So that’s kind of the cool part, witnessing it all.

How do you think tech can be more accommodating to diverse perspectives in design?

That’s something that I think about a lot. I really think it goes down to getting people involved early. I’ve met people here who have a lot of privilege, but they don’t realize it. And it’s very much a buddy system in tech where one person gets into a company, and then they only refer their friends and others in the social bubble. And because they don’t have a diverse friend group, the company’s demographics become very uniformed. Many people seem threatened by the idea of forcing diversity, but I think it is good to have someone at an executive level who is tasked with increasing diversity and making workplaces inclusive to all kinds of people.

Diversity and inclusion just isn’t a concern for most people in tech. For example, if you’re happy and comfortable with your design team being homogenous, then you’re probably not going to feel challenged to make it diverse unless somebody points out, “Hey, this is a problem.” I do feel lucky that at my current job we do have some diversity in the sense that there we have people of color on the team, and it’s mostly women. But we’re just a small company, and no one’s looking to us as a design leader in the industry compared to places like Facebook, Twitter, Pinterest, Google. And from what I’ve seen, those teams aren’t diverse.

“Black Twitter, a lot of the young people on there, they’re hilarious and amazing and I love it, but how many of the young kids participating are going to think, “I want to get a job doing something related to this?” I don’t think many are because it’s not being presented as something that they can be apart of. These platforms need to reach out early because that’s their audience right there.”

InVision just had a documentary they did I think last year or a couple of months ago, and it was like the top designers disrupters in the industry. Not one person of color was in there, I think. Maybe there one woman on the list. Stuff like that. People aren’t doing it on purpose. I think most of the people in these companies just don’t have very diverse professional and personal groups, so they likely couldn’t seek out diverse voices even if they wanted to. But if no one’s calling it out, it’s not going to change.

We also need to go into primary and high schools and get kids involved earlier. And not just coding—I think that introducing design as career options for underrepresented groups is important too. Because the kids—Twitter, for example. Black Twitter, a lot of the young people on there, they’re hilarious and amazing and I love it, but how many of the young kids participating are going to think, “I want to get a job doing something related to this?” I don’t think many are because it’s not being presented as something that they can be apart of. These platforms need to reach out early because that’s their audience right there. If you have a diverse user base, but the people creating the product aren’t, then you’re going to have some problems eventually. Tumblr had a problem, actually, awhile ago where they censored some popular tag, flagging it as not safe for work or something? I don’t remember, but it impacted a huge chunk of Tumblr’s user base. A lot of marginalized groups that feel like they can find their place or community on Tumblr, but suddenly they’re being treated different by the app developers. So now they don’t trust the app, and it’s perceived value for the user goes down. If only there had been one person, one voice on the team that could have been like, “Hey, this isn’t such a good idea.” That could have been avoided.

That’s why you need diverse teams. My hope is that as the internet generation grows up, we start seeing more diversity. I hope that tech becomes less of a “bro club.”

“I would love to stay in San Francisco for the next five years but realistically, I can’t. And I know I am speaking of a place of total privilege, as a tech worker in San Francisco. I can’t imagine how hard it was if I was still working retail or if I was working as an artist. I worry that life in San Francisco is not sustainable, so I really don’t know where I’ll be in five years.”

Where do you see yourself in five or ten years?

Oh gosh. Well as much as I love San Francisco, it’s really different now compared to when I moved here. I moved from Lower Haight to live in the Outer Sunset by the by the beach in 2014. I love living by the beach, but we truly only moved there because it was the cheapest place to find a bigger apartment at the time. But now getting downtown for work is such a hassle. I would love the ability to live closer to downtown, but I am not comfortable with how high rents are here. I would love to stay in San Francisco for the next five years but realistically, I can’t. And I know I am speaking of a place of total privilege, as a tech worker in San Francisco. I can’t imagine how hard it was if I was still working retail or if I was working as an artist. I worry that life in San Francisco is not sustainable, so I really don’t know where I’ll be in five years. I hope I’m still working as a designer, but likely it’ll be in a different area. I’ve heard that L.A. has a “Silicon Beach,” and I know there is a “Silicon Prairie” somewhere in the Midwest, although I see myself on a coast. I just hope that wherever I am in five years, I am making user experiences that are helpful to someone.

“You really have to be very self-driven because there are times where it seems that no one’s going to help you. You really do have to be self-driven, which I know can be hard, especially when you’re young. But when you’re competing with very privileged people for highly desired jobs, you can’t afford to wait around—you have to create opportunities by showing others your talents and interests.”

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

You really have to be very self-driven because there are times where it seems that no one’s going to help you. You really do have to be self-driven, which I know can be hard, especially when you’re young. But when you’re competing with very privileged people for highly desired jobs, you can’t afford to wait around—you have to create opportunities by showing others your talents and interests. When I got that job at my first startup, if I had waited for someone to ask me, “Well what do you want want to do besides admin work?” I don’t think that day would have come. Instead, I was like, “I know how to code. You guys need someone to make these internal pages. Do you want me to do?”

Another piece of advice is, as a person of color, people may look down on you sometimes or have lowered expectations. It hurts, but you have to say, “You know what, I don’t care about you. I’m going to give it 110% and prove you wrong.”

And finally, if you’re feeling alone, go online for support! Learn very early how to efficiently use Google. Search engines are your best friend. You can learn the basics by getting on free sites like Codecademy for code or UXPin for design. There are also tons of design and code communities out there, from Twitter to StackExchange to Quora to Reddit. It can be lonely and frustrating to work in tech, and it can be a lot of hard work, but overall it’s such an interesting and exciting place to be.

“It can be lonely and frustrating to work in tech, and it can be a lot of hard work, but overall it’s such an interesting and exciting place to be.”

]]> /tiffany-taylor/feed/ 0 /erica-baker/ /erica-baker/#respond Tue, 29 Mar 2016 03:50:56 +0000 http://techies.wpengine.com/?p=178 Where are you from? What were your early years like and where did you come from?

I am, technically, from Germany. I was born in Germany because I’m a military kid, but I lived all over the place. My path was Germany, to New Mexico, to Miami, to Alaska, to South Carolina, back to Alaska, back to Miami, back to Alaska, then to Atlanta, then New York, then California. I have to look at the map in my head as I’m saying that [chuckles].

How’d you first get interested in tech?

When I was younger my mom had a computer in the house. She was in the Air Force, also, and she did combat plans. And she had the computer around, and I used to poke around on it. And this was before Windows even happened. I still very much remember the black and green screen. And then about 5th grade— I was poking around when I was little, just playing Carmen Sandiego and that sort of thing. In about 5th grade my teacher decided that I should go to this thing that was in the city because we were in Alaska by this time. And so I got in a taxicab and went to a city as a ten-year-old all by myself, which — I thought I was grown. But it was teaching kids how to use HyperCard, which is, I don’t know, very early precursor, predecessor, I guess, to the web. It didn’t connect, but it was the idea of linking things together, and that’s how you navigated it. So I learned that, and then I was like, “I love this. I want to do this.” And I was just so enamored with computers, and I just spent all the time I possibly could either reading books or on computers. And then I learned how to install things on computers. And I learned how to dabble in hacking computers—and then senior year in high school I took a zero hour class which is like a class before school started that was not for credit that was learning how to program calculators. TI-83s. So we wrote BASIC on calculators which was good times typing and pressing those little buttons. There was no keyboard. Oh, yeah. Writing code on those things is not fun, but I got that. I got that feel, got that passion for it. So I—

You went to school early for it!

Yeah. And I was writing and making websites when I was a teenager and that sort of thing. My Geocities site was legit [laughter].

But yeah, I had that and I was like, “All right! I want to do this for my job.”

So I went to school at the University of Miami and I was a CS major for a year and it was the worst thing I ever did. Going back to Miami was great, but going to school next to one of the best beaches in the world was not a good idea when you’re coming from Alaska. Because it’s like, “But the beach is there. Class? The beach is there.” Then, when your classes are horrible because you’re the only woman, or one of  a few women in your CS class, and also you’re the only black person or one of two black people, and definitely the only black woman in your CS class, it’s like, “I don’t want to go there. It doesn’t feel good. The professor sucks and also he looks at me like I shouldn’t even be there. He won’t even call on me when I raise my hand, and he acts like I’m wasting his time,” and I’m like, “I don’t like it.”  So I didn’t finish my CS major there. I left after my first year and went back to, the University of Alaska, switched to a degree program, an AS degree, micro-computer support, which they’ve changed to IT something or another. Finished that, and then started working for the University. I intended to get my bachelor’s but they were like, “Hey, 21 year old Erica, we’re going to pay you $45,000 a year. Into it?” I was like, “Yup. Into it. Give me the money.”

So that was your first foray into work.

That was it. Windows Domain Administrator for the University of Alaska Statewide Systems.

Amazing. And so walk me through the path from that to what you’re doing now? Take me through it.

Windows domain admin at the University of Alaska. I got married—that didn’t work out. Then I was like, “I’m getting the fuck out of Alaska.” I was like, “All right. I’m going to apply for any job in a warm place.” And I was like, “East Coast”, because that is where the rest of my family is.  My dad was in Florida at the time. I was like, “Okay, anywhere in the East Coast that’s warm: I’m there.” I applied for a network operations position at Home Depot’s headquarters. Got that. Moved my entire life to Atlanta in three weeks from Alaska, which was fun. Yeah. I was at Home Depot for a year—I did network operations and mobile desktop support—then switched to this company called Scientific Games because they were going to pay me more money to do desktop support. So I did that. While I was there, someone told me about this site called Craigslist. I was like, “What is even a Craigslist?” I was looking at Craigslist and there was a job opening for Google. I was like, “Google doesn’t advertise jobs on Craigslist. No one even knows what Craigslist is. Why would Google have their jobs there?” I applied for this job at Google and I thought it was fake. I thought it was pretend, right? “This is a scam. I’m going to use my throwaway email address because this is totally a scam, but I’m going to send them my resume. But I know this is not real.”, until I flew in for my onsite interview in New York. And at this point I’m like, “Okay, so this is not fake. This is for real. Let me put my game face on.” So I pull up to New York, put my game face on, got the job. Worked at Google for nine years. Started as a field tech—which is kind of desktop support plus plus, and then did Google TV for awhile because I’m really into TV—I like to watch TV a lot—and then I switched back to the corporate engineering organization, and then I switched to SRE,  Site Reliability Engineering.

After that I went to Slack, because I was like, “I can’t work at Google anymore. It’s horrible. It hurts my soul to work here. I’m gonna work somewhere that is either making a difference in the world, or a place where I can be happy.’ Slack was a place where I can be happy.

I’m assuming that in your nine years at Google— I kind of want to dig deeper into— hopping from department to department, how was that? What were some of the projects that you worked on? Hopefully there were some parts that were really exciting and appealed to you and that you’re proud of.

In Atlanta it was cool because it was a small office and there were a lot of people there and it was very diverse. This was the most diverse office I worked in my entire time at Google. Everybody was there. When I moved to the New York office, it wasn’t as diverse. Also I was in a cold place again. Bad choice [laughs].  But I worked on  my favorite projects there, which is when Google did the DoubleClick acquisition, I did the IT onboarding. I was responsible for making sure all 500 employees that we onboarded got all their stuff, like their hardware, their usernames. I had to set up a whole process to get 500 people through the onboarding process within two days.

But that project was one of the most stressful things I’ve ever, ever done in my life. It’s one of the most rewarding projects that I’ve ever done. And I only got to do that project because my manager switched to a female manager at the time, and she believed in me and was like, “Erica can do this. She’s going to do it.” I don’t think that any other manager would have taken that chance on me because it was huge and I really appreciate her. She’s one of my favorite people at Google. I hope she ends up running Google one day, she was great.

And I switched— when I left New York, when I came to Mountain View, I was an Exec Tech and that was interesting, being in a position to work with all the executives at Google is tricky, because they are in positions—or were in positions—where they felt like they could say whatever they want to say. They didn’t have to put any checks on what they said. One executive thought I was my office mate’s admin assistant, walked in and was like, “Is Frank here?” I was like, “No Frank’s not here.” He’s like, “Oh, well can you tell him I came by and take this message?” I was like, “Can I help you with something? Do you need technical support or something? Is there something I can bring you?” Like, “Oh, you can do that too?” I was like, “Yeah.” He’s like, “Oh, I just thought you were his admin assistant.” I’m like, “Word? Really? Really?!” So that was super frustrating. They just had no qualms about saying the most fucked up shit. One of the executive’s admins— I was sitting outside a board meeting, and she walks over to me—as I’m sitting outside of the board meeting—and she’s, “Are you security?” I’m like, “No. I’m sitting here in my not security uniform wearing my work dress clothes, because I’m sitting outside a board meeting waiting for them to tell me that they need support with something. No! Not security!” I was so pissed off about that, but that sort of thing happened all the time. It was interesting, it was never that overt in either Atlanta or New York. I didn’t have much issue in New York, aside from them passing me over for stuff that could help my career for white dudes. That was the only problem I had in New York. Nobody ever came up to me and was like, “I think you’re an admin,” or “You must be security, because what else would you be doing here.” Working with the exec support— like the project I worked on, like working with the exec assistants to help them get their jobs done, like writing one auth little tools for them to blast an entire department with emails to go on a ski trip. Neat little tools to help them— I don’t know, like migrate from Palm contacts to Google contacts because that was the thing that they had to do. That was fun. That was rewarding. Even though there was bad, there was that good. There were some good people I was working with.

Well, we’ve already touched on this a good bit, but what have been your biggest struggles?

Like those things that I told you about. People just assuming that because I am a black woman—the worst one is people who assume that I only got hired because of affirmative action or whatever. It’s like, “No. I came in and I destroyed the interviews, and that’s how I got hired. I’m really fucking smart. I don’t throw it around, but I’m in MENSA. I’m not dumb, but you want to assume just because you look at me, you see I have brown skin and I’m a woman that, somehow, I’m not worthy. Immediately, that’s your assumption, and that is the worst thing that I have to deal with always.

“People just assuming that because I am a black woman—the worst one is people who assume that I only got hired because of Affirmative Action or whatever. It’s like, ‘No. I came in and I destroyed the interviews, and that’s how I got hired. I’m really fucking smart.'”

I wrote this thing called “The Other Side of Diversity.” I had been going to therapy and I was like, “I need to work out and figure out why I’m so unhealthy.” I was writing things— there were so many other things that I wrote about my life that I posted on my personal blog, and this one thing was like, “This is going to be the thing I write about working in tech, what it feels like to be a black woman in tech.” Everybody’s like, “Oh, we need more women of color in tech,” but here’s what it actually feels like to be a woman of color in tech. I wrote it all down and then it got so much feedback and when I wrote it, I was like, “This is what it feels like for me, but I didn’t know that it was everybody. There were so many people who were like, “This is exactly my story, this has happened to me, all these things.” I was like, “You know what? I don’t need to put myself through this.” There are other options out there. I don’t need to be hurting myself because someone says, “Oh, Google is the best place to work.” P.S., not the best place to work at all. But there was just a moment where I was like, “You know what, I don’t need to be here. I can go somewhere else.” At that point, I was like, “I’m going to go somewhere else,” because staying here will literally make me sick. It will make me stressed out, and stress leads to sickness, and I’m not going to do it anymore. And so I left. Right? [chuckles]

It’s amazing you lasted nine years.

My family got a lot of pride out of me working at Google. I was the one who made it, and I didn’t want to let them down. After a while, I was like, “I need to do this for me.”

How’s life been at Slack?

So great. It’s just so different to work in a place where the focus on inclusion comes from leadership. At Google, Larry would sometimes say something about diversity when a bad thing happened, but he would never proactively be like, “We need to fix this. This is a problem for us. I care about this.” It was either a PR situation for him or it was that something bad happened and we need to make sure that people know that we care about the diversity. But at Slack, Stewart was just like, “Yeah, this is important. This is super important to me, and this is super important to this company. We need to be out ahead of this before we even become a big company. This is really fucking crucial. We can’t mess this up,” because he’s so big on fairness and justice and making sure that we don’t contribute to the problems in tech. And so just to have the different ethos at the top of the company affects so much. Every company should be run by a philosophy major.

“Just to have the different ethos at the top of the company affects so much. Every company should be run by a philosophy major.”

Tell me about whether or not you’ve had mentors or role models or even inspiration during your time in tech, or none at all?

None. No mentors. I guess maybe the lady I told you about who believed in me to do the project, that was the closest thing to a role model. I had something like a mentor for the last few months I was at Google, and she was pretty cool, but she was super busy, because everybody knew she was great, and so we rarely had time to meet up. Besides those two, from my 15 years in tech, I’ve not had a mentor, ever. People like to mentor people who look like them, and there’s nobody in tech who looks like me. Well not nobody, but there are very few people in tech who look like me. There are definitely very few within my line of work, like in operations and system administrations and that sort of thing.

Yeah, for sure. And your family’s not here, so I’m curious to know where you found early support networks.

Yeah, my mom was up in Yuba City and my sister is still up in Yuba City. My mom passed away in 2010, but my step-dad is still there, and my sister and her kids and husband are still there so, when I need to get away, that is where I go. But outside of going to see them, like there were no support networks here for me, until I decided that I needed to not be in the South Bay. Because there’s nothing there for me, like everybody there treated me like I was different, because I looked different, and so I felt different.  Oakland, it was like “Oh, hey, my people.” And I now have a great support network, I have so many friends and places I can go and get away from tech, which is important to me. I think that’s a good thing for everyone to have, an outlet to get away from tech.

How did you do it?

I just survived. I didn’t flourish. We have this thing at Slack called “thriving,” and I didn’t thrive, I survived. That’s how I did it. So glad I feel like I’m living again, versus existing.

What are your biggest motivators? What drives you?

Making sure my nieces and nephews have a good role model. My nieces and nephews’ mom and dad are great, but they aren’t in tech and my nieces and nephews don’t see that tech is a thing that someone can do. I want for them to be able to see me do these things. I want for them to see me achieve. I want them to know that it is something that they can aspire to. That’s a huge motivator for me. My work on diversity and inclusion, I am motivated by making sure that the industry gets better for people who come after me. Because I don’t want anybody else to have to experience what I experienced. Diversity and inclusion work is not my first choice. If I could be spending my free time doing stuff, I’d be doing genealogy all the time. That is what I love to do. But I work on diversity and inclusion because it’s super important. Right now I get to have this voice—people listen to me for some reason, and I have support at work to continue speaking about these things;and permission to say whatever I feel from the CEO of my company—which is super rare, Not everybody gets that. And it’s a huge privilege, and so I’m not going to waste that privilege. I want to use it to speak up so that we can make improvements. I think the first step is talking about what’s going on and then getting uncomfortable. It’s not going to be easy, right? Talking about sexism and racism is super hard, but I feel like we keep talking about it, people will get used to talking about it. And then we can move on to fixing it.

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

I think we are doing major things and making major accomplishments and taking major steps forward in tech. So many innovations, so many new cool things out there. Tech itself is great. The social structures, I guess that have been built within tech, the diversity of Tech? Horrible. The way people behave in Tech, horrible. We’ve created this system wherein as long as you know how to write code, as long as you perform well in your job, you should feel free to say whatever you want to about whoever. Like that’s the system we’ve built, and that’s not so good.

“The problem in Tech is that nobody wants to acknowledge that because they want to believe that it’s a meritocracy. They want to believe that their hard work is what got them here like they’ve struggled and suffered for all this time and that’s how they got here instead saying, ‘Maybe you got here because that guy you knew in college he referred you for a job but he didn’t refer the black girl who was also in the same class who actually got better grades than you.'”

And also, people are so married to this idea of meritocracy and like “Oh Tech is a meritocracy,” and whatnot that they can’t get beyond that and see that Tech is just another part of the society we’re in and it is affected by systemic racism, systemic sexism, and all manner of injustice just like everything else.

The problem in Tech is that nobody wants to acknowledge that because they want to believe that it’s a meritocracy. They want to believe that their hard work is what got them here like they’ve struggled and suffered for all this time and that’s how they got here instead saying, “Maybe you got here because that guy you knew in college he referred you for a job but he didn’t refer the black girl who was also in the same class who actually got better grades than you.” They don’t think about that—it’s just like, “I worked hard to get here, so I deserve to be here.” And that’s— it’s really unfortunate that that’s a widespread belief, and it’s hard to change people’s thinking on that. They’re really really married to that idea that it’s a meritocracy and if we can convince some folks that it’s not and that there’s some systemic issues that we need to work on then I think we can move forward.

I think the idea that it’s not a perfect meritocracy threatens some people’s own credentials and it scares them.

Oh it definitely does, and I think that there are many people who are frightened of it.  Yes. They’re so scared of that. Because to consider that maybe you are not like this super smart, super special person, that got into tech…like that’s the story that they’ve been told, like at Google “we hire the BEST engineers in the world, only the best. We get all the best.” It’s the story that they’ve been spoon-fed and they get attached to that story, and to take that story away is just like NO. This legitimizes me. This makes me important, and to take that away is like, now they don’t have something to cling to, to show that they have value.

Yeah. I remember the moment where I became disillusioned. It was when I worked at this little YC startup, and I was so passionate about the product. I was obsessed with it. But I started seeing that it wasn’t about the products—for me it was about the product, but for them it wasn’t about that, it was about finding something that they could sell, or making something decent enough that they could sell. And then, it was about hiring another McKinsey alum to help them sell it through the connections that they all had from their networks and it was just like, “Oh, this isn’t about what I thought it was. This is about boys all sitting in a room together and selling stuff to each other.” And that was a moment where I was like, “Oh man, like, my high hopes and my naive ideas about what everyone was here for. It’s not what I thought it was.”

To have that moment of realization is hard.  Oh, I thought I was working in the best company in the world. Turns out, no—I believed the hype I drank the Kool-aid. But, no. I am sorry you experienced that. It’s frustrating.

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

I already spoke about being able to assimilate really easily, so that has impacted my life, But also when I was growing up I had this button that said question authority. And I believe that. I don’t know where I got it. I am pretty sure my mom never gave it to me, because my mom did not like when I questioned her. She was the authority person. But, you know, I strongly believed in questioning authority. And also there is a song in 1996-1997, in Biggie’s last album. It was “N-words bleed”. And the lyric that really stuck to me was “N-words bleed just like us. Picture me being scared of an N-word who breathes the same air as me.” And even though the language is wrong, and the song is about being in the streets, and murder and that sort of thing,that line for me, is like, “Oh right. That’s just saying that everybody out there is a person just like me. And I don’t need to be afraid of them because they’re just another person. They breathe just like me. They poop just like me. That CEO, or whatever, that I just said, “Hi” to or whatever, or emailed or asked the question or didn’t feel any qualms about talking to, that’s just another person. They just had different life experience than me and they got a little luckier than I did. And so that has helped me a lot in my career because, for some reason, people think that being able to speak to people in positions of power and authority— it’s like a magic trick or something. No. They’re just other human beings.

Let’s go back to Slack. As an outsider, I just feel like they’re leading the front, in terms of diversity and inclusion. And not just in quantitative ways, like everybody’s doing—posting the numbers or whatever, but hosting Deray at the office. All these little things. And Stewart not being afraid to speak up as an executive.

The head of diversity should be the CEO. CEO can have a deputy. It’s like, this is my deputy of diversity or whatever. But the CEO should be the person for whom all diversity reports  go to.  The CEO should be the person who is leading this charge.

This is the person who everybody has to report to about diversity. This is the person who will tell the company how the diversity is going — that sort of thing. Like, the CEO should be the person in charge, and they might say, you know, the deputy is going to take care of these parts, but you’re still answering to me about it, right? And so that is what I think should happen with CEOs. Sadly, it doesn’t happen. Companies just hire Heads of Diversity. And then, they think that’s all they need to solve the problem. Especially Twitter hiring Head of Diversity that was ineffective as a Head of Diversity in other companies.

“The head of diversity should be the CEO. CEO can have a deputy. It’s like, this is my deputy of diversity or whatever. But the CEO should be the person for whom all diversity reports  go to.  The CEO should be the person who is leading this charge.”

What would be a very easy next step for them to do?

Those quantitative numbers about how many people they have hired, that’s all about recruiting. They need to start focusing on retention and happiness. How are people at your company feeling? A great thing Google did just before I left is that they do these surveys every year called Googlegeist—they surveyed the entire company to see how they are feeling about working at Google. For the first time last year, they asked people, randomly selected groups of people to do a separate ends of the survey. And one of those was diversity related, like if you feel comfortable sharing your gender, if you feel comfortable sharing your ethnicity and then, you know, answer a few questions. And they found that people who were black people at Google, did not feel like they could succeed in the way that other people felt like they could succeed at Google. And that is a huge metric to be watched. That should be what they pay attention to. You’re hiring? Fine. But, to feel like you cannot succeed in your workplace is a problem. And they need to make sure that number is going up, right? So, companies can be tracking retention, how people feel included in ways that works for them. They should not be high-fiving just because their 2% went up to 3%. That’s terrible. High-five when your percentage matches the rest of The United States population. When you have, whatever the current percentage is, of black people in The United States at your company, then high-five yourself. Same for the Latinas and Latinos etc. Then you can high-five.

“That should be what they pay attention to. You’re hiring? Fine. But, to feel like you cannot succeed in your workplace is a problem. And they need to make sure that number is going up, right? So, companies can be tracking retention, how people feel included in ways that works for them. They should not be high-fiving just because their 2% went up to 3%. That’s terrible.”

What do you think tech can do better to keep talent from leaving?

Understand first that your talent is leaving because your culture is horrible. Come to terms with it. Get really uncomfortable with it and then get comfortable with it and then fix it, right? Recognize that you’re going to have to do some work on your culture. You just can’t keep shoving people in like, “Oh, we’re going to just hire all these black people or these Latino people or these women. We’re just going to keep hiring and hiring, and that’ll fix it.” I feel like companies need to recognize that that’s a problem that they have and then work on it. Like I said, it’s like we’re looking at every little thing, and I feel like companies can look at every little thing. Like, “What is this here for?  Why are we playing ping-pong? What is this serving? Who is this serving? Who is this for?” That sort of thing. Every single aspect of your culture. Look at it with a fine-tooth comb. It’s going to be painful, it’s going to suck! People are not going to like it. But look at every single aspect of your culture with a fine-tooth comb and figure out what is not inclusive. What would feel weird for somebody to participate in? Maybe that trip to the gun range, maybe not the best idea for a team off-site. You know, that sort of thing.

“Understand first that your talent is leaving because your culture is horrible. Come to terms with it. Get really uncomfortable with it and then get comfortable with it and then fix it, right? Recognize that you’re going to have to do some work on your culture. You just can’t keep shoving people in like, ‘Oh, we’re going to just hire all these black people or these Latino people or these women. We’re just going to keep hiring and hiring, and that’ll fix it.’ I feel like companies need to recognize that that’s a problem that they have and then work on it.”

Where do you see yourself in five or ten years?

Hopefully alive? [laughter] You know what, I don’t know. If Slack is still here, I’ll still be here. But if Slack is not here, I won’t be. Slack is my last stop.

Unless I start my own company— which I don’t see happening. Everybody keeps trying to push me towards that, and I’m like, “I don’t have an idea that is good enough to start my own company.” But unless I start my own company, Slack is my last stop in this industry. I will go back to the East Coast and work on whatever. Photography maybe. I don’t know. Something on the East Coast and chill, and not be in this terrible, terrible environment. Unless it gets better. If it gets better, I might stick around, but I don’t think that’s going to happen in five to 10 years. Maybe 20.

“I think the first step is talking about what’s going on and then getting uncomfortable. It’s not going to be easy, right? Talking about sexism and racism is super hard, but I feel like we keep talking about it, people will get used to talking about it. And then we can move on to fixing it.”

What advice do you have for those from a similar background who want to get into tech?

If they’re in tech, recognize that you’re not alone, find your people. There may be only a few at your company, but there are many of us out there not in your company. Figure out how to get to your people. There are women in tech groups, and women of color in tech groups, and people of color in tech groups all over FaceBook. And there’s Slack groups or whatever. Find your people, and I can’t even stress how important that is because it gives you a place to go when you feel like there’s nowhere to turn. Try not to get discouraged. I’m not going to tell people not to rage-quit because I’ve been right on the cusp of doing that many times. But try not to get too discouraged, and if you do get too discouraged, tell your people. If you found them, well they can help you out with that. Don’t be afraid to speak up, and if you feel like you don’t have a voice and  you need your story to be told I’m happy to tell stories for anybody. If you need to be anonymous I’m happy to do that. For people who aren’t in the industry already, make sure you really want to be here. You have to really want to be here to deal with all this shit. Like if I did not love computers as much as I do I would not still be here. If I did not love tech as much as I do I would not be here. I’d be off somewhere trying to get a law degree or something because that was what I wanted before I discovered computers, I wanted to be a lawyer, so that’s what I’d be doing. But I love Tech so much, that I can’t let go of it. But make sure you really want to be here, because that love is what’s going to keep you here when someone tells you that you shouldn’t be here. 

“Try not to get discouraged. I’m not going to tell people not to rage-quit because I’ve been right on the cusp of doing that many times. But try not to get too discouraged, and if you do get too discouraged, tell your people. If you found them, well they can help you out with that. Don’t be afraid to speak up, and if you feel like you don’t have a voice and  you need your story to be told I’m happy to tell stories for anybody.”

I grew up in the Bay Area. Both my parents were computer science PhDs and software engineers. As a kid I practically grew up in my parents’ office, surrounded by computers. It might seem like I was always destined to be in Silicon Valley and to be a software engineer. But actually, back then, tech wasn’t glamourous. And I didn’t actually know what my parents were up to. I didn’t think of tech as a dream career; I just knew it was one thing that I could do because both of my parents did it. Even though I eventually ended up in tech, it wasn’t because I had set my sights on it and headed directly there.

So you didn’t always know you would be an engineer. When was kind of the moment that you first became interested in a real way?

I can’t pinpoint a specific moment.

It was always a possibility because both my parents had been engineers, but even all through college I wasn’t sure what I was going to do. I started thinking I might want to do linguistics. I also considered bioengineering, because biotech seemed like it might be hot. But I took a class or two in each of those fields and decided they weren’t for me. I ended up doing an electrical engineering major, mostly because of continuous iterations of sunk cost fallacy after I took a circuits class with some frosh dorm-mates. A year into that I decided I didn’t like EE, either. I finally landed in the master’s program for computer science, but still more to prove that I could do a master’s in something technical than anything else. A friend had dared me to do it. As I went through my degree programs, I started to become more okay with the idea of doing something on the engineering side. And so when I was graduating, I looked at data science or data analyst type roles—getting closer to engineering, but still not quite there; and somewhat reluctantly I also interviewed for software engineering roles, because every company was hiring engineers and there were more opportunities there.

In the end, I was convinced to join Quora as a software engineer. At that time, the company was only four people and they really just needed engineers to help build out the product. As for my inclinations towards data science or data analysis, there just wasn’t any data yet. Adam told me to try out the engineering side and we could re-adjust later if it wasn’t working. I figured I would give it a shot. So that’s when I actually started doing software engineering. That’s also when I actually started realizing how cool software was. Of course I’d taken computer science classes, I’d done internships, etc. but it wasn’t until I was on the ground floor of a really early stage startup that I understood that we were building a product from scratch and that I realized how powerful it was to be bringing things into existence. Somehow before that I didn’t get that engineering is about building things; a bit ironic, given that I already had two degrees in engineering by that point. But finally at Quora, I got it.  

What are some of the things that you are proud of over the course of your career so far?

As an engineer, I’ve found the most exciting and rewarding experiences to be in the early stages of building products and getting them off the ground. I was at Quora early, as #5. I signed on with Pinterest when there were only 8 people on the team. With both companies, I joined before it was clear at all that the products would become big, whether anyone would be interested in using them, and it’s been amazing to be a part of both those early teams building out and scaling consumer web-scale products.

Aside from that, I’ve done some work supporting and advocating for diversity in tech and though I’m just a small part of the movement, I’m proud that the last few years have seen dramatic change in the industry’s awareness of the issues and commitment to fixing them. When I first started working, I felt overwhelmingly alone and frustrated, and I didn’t know whether it was just me, if I had anyone to turn to, and just generally what was even going on. We’re far from having fixed any of our diversity issues, but they’re at least out in the open and people are starting to talk about them now.

You are known as a major catalyst in getting tech companies in Silicon Valley to acknowledge their diversity issues. When were the seeds for that planted?

Early on, when I was at Quora, I was very plugged into the startup community and in the course of being on the site itself, going to events, all of that, I got to know people at lots of different companies. Not deliberately, but just offhand, I also came to know how many female engineers were at each of these companies. I had a rough mental catalog. Not perfect, but I had some sense of what companies were up to, and it was more than anyone else had, I think.

Then there was a specific moment, when I was at the Grace Hopper conference in 2013, at a group breakfast with Sheryl Sandberg, where she made a comment to the effect of how the numbers of women in tech were dropping precipitously and we needed to take action, that I had the gut response: “How do you know what the numbers are? How does anyone know what the numbers are?” And then I was struck by the irony that in an industry that was so data-driven, where we had metrics and dashboards for everything, where we studied conversion funnels from landing page to signup to activation so fastidiously, where we ran A/B tests for every new color and UI element much less new features; we had no data on diversity.

“I was at the Grace Hopper conference in 2013, at a group breakfast with Sheryl Sandberg, where she made a comment to the effect of how the numbers of women in tech were dropping precipitously and we needed to take action, that I had the gut response: ‘How do you know what the numbers are? How does anyone know what the numbers are?’ And then I was struck by the irony that in an industry that was so data-driven, where we had metrics and dashboards for everything, where we studied conversion funnels from landing page to signup to activation so fastidiously, where we ran A/B tests for every new color and UI element much less new features; we had no data on diversity.”

When I got home to San Francisco after the conference, with all these thoughts still swirling around in my head, I sat down and wrote a Medium post. It was framed as a call to action but in truth I didn’t expect anyone to take it on. I definitely wasn’t the first person to ask for numbers. Even in the process of writing my post, I went googling and found a CNN report from a few years prior that said that investigators had reached out to a bunch of tech companies to ask their numbers and all the companies said, “No. No thank you.”

I didn’t expect anything to change after I wrote my post. It was a big (and pleasant!) surprise to me when people started sharing their numbers with me over Twitter. But then I realized that my @mentions were not a good place for this data to live, and so I set up a GitHub repository to track it. Why GitHub? It was something that a lot of engineers are used to using. And it supported tracking the metadata: who was submitting the data, what their source was, the date of submission, any other relevant context, and also the history of updates. The project was meant to be crowdsourced, so it was important that we had that metadata.

I’m up to about 250 companies now that have submitted their data. It’s mostly the smaller companies, but that’s fine, actually. What’s more important is that there was an upswell in attention on the subject and the larger companies realized too that it was important to publish their data. In May of 2014, a few months after I wrote my Medium post and started my GitHub repository, Google was the first big tech company to release a holistic diversity data report. The story I’ve heard through back channels, though I haven’t been able to validate it, is that people in Google HR got wind of what I was doing, discussed, the question made its way all the way up to Larry, and he made the call to release their data despite objections from legal. And their report was more than just women in engineering; it also had race breakdowns, and it covered tech, business, leadership, etc. After Google, most of the other major tech companies followed suit. It’s become an industry-wide movement.

I’ve been hearing women recently who work at well-known companies here and talk about wanting to leave those companies for Pinterest, because they want to work with badass ladies and that’s like becoming more and more of a priority for more and more talented people that just want to be surrounded by with other really talented people.

Yes, I’ve heard that a lot amongst my friends too. They’ll say things like, “I don’t have to put up with BS anymore.” And I’ve felt similarly myself. Even within Pinterest, where I’ve changed teams a few times, when I’ve looked around, one of my top criteria has been whether there are women that I’d want to work with. Not to say that I’d necessarily rule out opportunities on teams that didn’t have women, but at this point I really prioritize being able to work with other talented women. I’ve worked on a few teams now that had 50/50 gender balance, and I can say that the dynamic is different, and so much better, when that’s the case. That’s not to fault men on more male-dominated teams, but the dynamic really is very different.

Absolutely. How have you seen tech’s attitude towards women changed since you’ve started in the industry?

There is substantially more awareness now of unconscious bias and the ways in which women (and underrepresented minorities) can be disadvantaged, even if unintentionally. I’ve also seen a lot more allies become a part of the conversation and the solution. But it’s a slow shift. We’re trying to engineer a really big cultural change, and that takes time.

And people have lived their whole lives under certain conceptions of how things work, their certain beliefs about the world. And it’s hard to dispel those in just a short period of time.

I get surprised that these people still exist, but explain to those who are in doubt about this why having a team with diverse perspectives is beneficial to a product.

First, there’s the research that shows that diversity makes teams more creative, more diligent and thoughtful. Intuitively that makes sense. People from different backgrounds and perspectives engage in different ways, and in more diverse team settings people are forced to confront the reality that other people may perceive and think about things differently, and therefore end up working a little bit harder to justify their thoughts, their opinions, whatever they’re proposing. And the research also shows that diversity drives better business outcomes. It’s smart business.

“People would make comments about Pinterest like, “Oh, that seems like a niche market.” They thought it was niche only because they weren’t women.”

As for the tech industry specifically, we’re building products and services for everyone. The quality, relevance, and impact of these products and services can only be improved by having the people who are building them be demographically representative of the people who are using them. Here’s an example of a very obvious oversight from lack of gender diversity: Apple launched HealthKit in iOS 8 as a comprehensive health and fitness portal app to track nearly everything you could think of tracking, things like blood alcohol content, inhaler usage, sodium intake , but somehow they missed period tracking. This is the one thing that almost all women track and have tracked probably for the entirety of human history, even in the absence of any fancy quantified self devices or apps. But you know, women’s health, no big deal. To be fair, I don’t know if there were women on the HealthKit team, and maybe there were and something just went awry, but it feels like if there had been more gender balance on that team they wouldn’t have missed something so obvious.

I remember when Pinterest first launched and there was so much hoopla over how this company catered to a population outside of Silicon Valley and grew so huge and it blew people’s minds. They couldn’t believe that by catering to the world outside of Silicon Valley that they had tapped into something lucrative.

People would make comments about Pinterest like, “Oh, that seems like a niche market.” They thought it was niche only because they weren’t women.

An interesting comparison point is other major Internet properties that skew male. They’re considered neutral. Think Wikipedia. Something like 90% of their top editors are male, but the Wikipedia is regarded as very neutral source of truth. Nobody ever talks about how masculine Wikipedia is, because in our society male is the default. Only when a site has a demographic that skews female does it have to be called out as “so feminine, so female”.

Personally, how do you think your background and life experiences have affected the way that you approach your work and your perspectives around the things that you build?

To be very honest, I’ve grown up very privileged and a lot of my life experience matches that of many other people in tech. Somehow the most unusual part of my background is that I’m a woman, which doesn’t seem like it should be that unusual.

One more thing to mention, maybe: I’m very American, but I’m also the child of immigrant parents. I still have a bit of the immigrant mentality. There are a lot of things that you don’t take for granted when you are not from the country you live in—you don’t have your support systems here, you’re much more focused on survival, as opposed to assuming that things will always be fine and there’ll be people to support you. There’s a certain risk aversion that comes from that, an unwillingness to “rock the boat,” so to speak.

“There are so many other people that have worked on diversity in tech, too. There are so many people that have been a part of this crowd agitating for change. It feels unfair to me that I get the attention that I do. But if I have the stage, I’m going to try to use it.”

There’s also that feeling of being an other. I grew up never seeing any images in media of people who looked like me, whether in entertainment, politics, business… I was just talking to some friends the other day about Disney movies and which ones we like the most. My favorite has always been Mulan, but it’s hard for me to know if I like Mulan the best because she’s the only one who looks anything like me, or if I would have liked it the same with a blonde blue-eyed princess.

On that dimension of being race and being Asian, though, one interesting thing about tech is that Asians are so overrepresented. Asians aren’t a minority in tech. When people talk about people of color in tech, they don’t include Asians even though Asians are people of color.

So obviously your diversity work has kind of thrust you into the public, and you’ve become a very public face of diversity. How has that affected your life? I’m sure it’s been positive and a little scary.

It’s been surprisingly positive.

That’s good.

I do find the attention a little strange because I don’t think my story is that special or that I’ve done that much. There are so many other people that have worked on diversity in tech, too. There are so many people that have been a part of this crowd agitating for change. It feels unfair to me that I get the attention that I do. But if I have the stage, I’m going to try to use it.

On the negative side—I’ve been pretty lucky to not have had any serious incidents of stalking or harassment, only a couple of cases. I don’t think they’re that bad, although I’ve had people tell me, “It’s not normal to have stalkers at all. The fact that you’ve had to go to the police before is not normal.” But it hasn’t been that bad.

Wow. It’s funny that we feel that it’s totally normal, because we have perspective from these other women in the industry who have gone through things a thousand times worse.

Oh, yeah. It’s like, “Oh, I’ve only had, like, two stalkers.”

Oh, man. Back to what you were just talking about earlier—you’ve written about being Asian in tech, and how sometimes the Asian population can be put in a bit of an awkward place in discussions around racism and discrimination. I’d love to hear more on that.

The topic has been wearing on me a bit as I’ve heard so much talk about issues of race and racial diversity in tech, people insisting that we need more people of color in tech—but Asians are so conveniently left out. There are plenty of Asians in tech, and we are people of color. Somehow in the tech context, though, we don’t count. It’s only Blacks or Latin@s. That’s such a strange oversight to me. Sure, Asians are overrepresented in tech, and yes, we complicate the conversation. But that doesn’t mean we shouldn’t be a part of the conversation.

“I’ve been pretty lucky to not have had any serious incidents of stalking or harassment, only a couple of cases. I don’t think they’re that bad, although I’ve had people tell me, ‘It’s not normal to have stalkers at all. The fact that you’ve had to go to the police before is not normal.'”

If we back out to a larger conversation of Asians in America, perhaps the first thing to talk about is the model minority myth. We’re expected to be hardworking and good at science and nerdy things. In theory this sets us up for success in tech. But this model minority myth is dangerous. It was originally constructed as a tool of anti-Black racism in response to the civil rights movements of the 60s, setting apart Asians as a community of color that has succeeded due to our work ethic and good character (and thus implicating Blacks as responsible for their own inability to pull themselves out of poverty and crime). It cleaves apart communities of color in a way that props up white dominance and supremacy. And it’s also not actually that great for Asians. Part of the stereotype of Asians is that we’re good rank-and-file employees but not good leaders, and that’s borne out in the numbers. We’re overrepresented in the lower ranks and underrepresented in executive roles; there’s definitely a bamboo ceiling. And if we go back to intersectionality, the expectations on Asian women are even more constraining than those on Asian men.

As you can tell, I’m kind of all over the place on this subject as I’m still trying to feel out the relevant themes in the conversation.

I think that most people don’t even know the complexities whatsoever. I didn’t know the term “bamboo ceiling” until I did this project and saw the term in my submissions.

It’s also really important that Asians get involved in the conversations around having more Black and Latin@ people in tech instead of being complicit in racism against them.

Kind of in the same realm, do people make assumptions about you based on what you look like—being race, gender, fashion, demeanor?

Yeah. It was much more so the case earlier in my career. Maybe partly because I was younger and not as far along in my career and fewer people knew who I was.

I had the experience once of going to a conference (PyCon) and people not taking me seriously when I was wearing a dress and looked feminine—they assumed I worked in recruiting—but then engaging me in technical conversation when I showed up the next day in a t-shirt and jeans. Another time I went to a woman’s meetup and when I mentioned to someone I had worked at Quora and was then at Pinterest, her first response to that bit of information was to ask, “Are you the community manager?” Not to say that there’s anything wrong with recruiting or community management, but it’s frustrating for those of us in engineering to be always assumed to not be in engineering.

Each of these experiences isn’t so significant in of itself, but repeated over and over it’s that feeling of death by a thousand papercuts.

Yeah, I get it. Even in photography, I have people assume that I’m not the photographer.

That’s so frustrating.

Have you had mentors or people that you’ve looked up to for inspiration?

I don’t have mentors in the classical sense of the word, although there are people that I’ve found resonance with, in specific aspects of their identity and success. The closest I’ve had to a mentor is probably my mom: She was a software engineer, and so she just was an example of what I could become. And that was very powerful.

A few years ago people used to ask me this question a lot. “Do you have any mentors?” And it was usually a binary choice. “Sheryl or Marissa?” I never really identified with either of them very much. Sheryl’s not technical. Marissa was technical but never worked as an engineer either. And she has made statements to the effect of, “I don’t think that I would consider myself a feminist,” and denied the role of gender in the modern world, which is very baffling to me.

One person that I really admire is Megan Smith. Not a mentor, but definitely someone I look to for inspiration. She’s a badass MIT-trained engineer and has held a number of important leadership roles; she’s very motivated by impact and has done a lot of great work with Google and now in the government. And she’s very compelling in calling people to action in a way that conveys urgency but not shame.

What are your biggest motivators?

My biggest motivation is a sense of moral responsibility in taking advantage of all the privilege and advantages I’ve had to make the world a better place. I know that’s very vague and not prescriptive at all, but I’m trying to turn that motivation into something real.

I was lucky to be born in America and to grow up here in the Bay Area, in a middle class family, with parents that valued education and let me focus on my education and not worry about anything else. I was lucky again in being able to attend Stanford and to have all the compounding privileges from that. Good internships, good career opportunities, the right networks. I didn’t deserve all of what I’ve been given but it’s not like I can give it back. All I can do is try to pay it forward.

Similarly, I feel like you do a lot to give back to the community, and when did that become particularly important to you?

It became most important to me after I’d had a series of not-great experiences, felt very alone and unsupported, and didn’t know where to turn. I was seriously considering quitting tech. And that’s despite the fact that I love software engineering. I love coding. I love building things. The job is a great match for my skill set, and there’s a lot of market demand for software engineers. Even so, I was really close to leaving. And I imagine there are a lot of others—actually, I know that there are a lot of others—who’ve had the same sort of frustrating experiences that I had. I just want to help make it so fewer people have to go through that.

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

In terms of diversity in tech, we still have a long way to go. We’re trying to make that difficult transition from awareness of issues to commitment to action. Commitment is more than a blog post saying, “We care about diversity and here are our numbers.” But it’s hard to make diversity a priority because it’s a long-term strategy. It’s not something the companies see the benefits of immediately. Teams don’t suddenly more innovative as soon as a woman or black person is added to the mix. So in the face of short-term prioritization, companies are often unwilling to commit to diversity.

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

I hope so! I don’t know exactly what I’ll be doing, but I hope that I’ll be using the power of software to help alleviate issues of social injustice. Again, very non-prescriptive. But I think there’s a lot of opportunity to apply tech to these problems that haven’t traditionally been the focus of the tech industry.

There’s that criticism of Silicon Valley startups, that they’re focused solving one problem: “What is my mother no longer doing for me?” And they’re getting so much funding and attention! Some of the criticism is fair, I think.

Yeah. There are many many many people in the industry—a lot of which I’m interviewing for this—that know the potential that tech can make on real, significant problems outside of Silicon Valley.

We definitely are starting to see more of those companies. They’re not as flashy, not as sexy, but so important. Just for a few examples: There’s Honor, which is helping to provide elder care. And I was just talking to someone last weekend whose company is using data science to map out gas leaks from pipelines and to provide that information back to drilling companies. They’re addressing the problem of climate change through data science.

“Commitment is more than a blog post saying, ‘We care about diversity and here are our numbers.’ But it’s hard to make diversity a priority because it’s a long-term strategy. It’s not something the companies see the benefits of immediately. Teams don’t suddenly more innovative as soon as a woman or black person is added to the mix. So in the face of short-term prioritization, companies are often unwilling to commit to diversity.”

I feel like, keeping talent in tech is just as hard as recruiting it in the first place. So what do you think tech can do currently to prevent folks from leaving?

This is a hard problem since it’s not that there’s just one thing that’s wrong. It’s a whole culture that’s broken, we have to change the culture, and culture change is hard. Recently I’ve been trying to read up on different social movements, like the civil rights movement, to understand how those have played out and where they’ve seen success and failure. But even for the Black community, after decades of civil rights activism, there’s so much left to do. Just take a look at our system of mass incarceration that is essentially systemic racism.

But to get back to the specific question of tech, what companies can do to start addressing retention issues—going back to the metrics—is to measure everything and to understand where the problems lie. Google, for example, measures everything and they have a whole people analytics team that’s looking at this kind of data. They saw that there was an attrition problem with new moms and introduced a more generous maternity leave policy. When they did that, attrition dropped by 50 percent. The data is clearly going to be very useful in informing policy decisions within companies.

And lastly, what advice would you give to folks who may be able to relate to you in some ways that are hoping to get into tech?

The tech industry may be simultaneously easier and harder than you might expect to get into. On the one hand, something like software engineering is really just a trade skill, something you can pick up if you are interested and put in the time. On the other hand, the culture and values and processes that define the industry right now aren’t always very conducive to inclusivity and it can be difficult to navigate. But being in tech is about building the future of the world we live in, and it’s worth it.

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

What part of Virginia?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

God bless SF.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Where have you found your support networks here?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

I was born in the Philippines. I’m ¾ Filipina and ¼ Austrian. I understand Tagalog and I speak elementary German. I have lived in the Philippines, Germany, and all over the United States (Connecticut, Nebraska, Missouri, California, New York, Boston). My family relocated a lot because of work, so from an early age I was comfortable with the idea of constant change and impermanence.

I was a hard worker and rather ambitious for as long as I can remember. For example, in the third grade, there were these boxes with cards in various colors for different topics like math, language, science, etc. Every day you were supposed to do three. I remember feeling rather competitive and ambitious (with myself, not against other classmates) and I would want to finish the whole box as fast as I could. So what I would do is, I would steal a large quantity of cards, take them home, and then I would work on them the whole day. Sometimes it’d be 9:00 PM and my mom would be like, “Why are you still working?”. I would lie and tell her that it was homework and I recall she was so perplexed – how can a third grader have so much homework? My teachers were also perplexed at how I managed to finish boxes and boxes of cards during school hours, but for me, it was just fun.

How did you first discover tech and get into tech?

I first learned about tech at Stanford. When I started at Stanford, I was certain I would become an investment banker and work for Goldman Sachs. My grand life ambition at the time was to one day become the CEO of Goldman Sachs and I had to start now!

One day, my best friend was telling me how she discovered the tech industry and how she wanted to “do start-ups”. I asked her what that meant and she said, “Well, in tech you have a really scrappy attitude. So, let’s say you don’t have a table. What do you do? Well, you don’t buy a table. You don’t have time for that. You grab a box, then you rip down the door, you put the door on top of the box, and ta-da! You have a table. That’s how scrappy you have to be when you do start-ups.”

“If I’m going to be CEO one day it might as well be now.”

Her “how to make a table” story made such an impression on me. It was the seed of ever considering doing a start-up because I could see myself thriving in an environment with other people who shared that scrappy attitude.

I continued to pursue my investment banking dream. I became the president of the investment club, did internships at top banks every single summer and even during the year, and eventually got an offer from J.P. Morgan in New York for their Leveraged Finance division. But the truth was, by the time I experienced the “New York banker lifestyle” that I always dreamed of, I was deeply unfulfilled. I remember asking my boss, “If I put in the best work possible and have the skill-set of an Associate a year from now, will you promote me?” And he said, “No, it doesn’t matter how good you are, you still have to do 3 years and then go to business school for 2 years and only then can you become an Associate.” This didn’t sit well with me and long story short (after relinquishing my “banker identity” that I had held on to for so long) I decided I was going to start a company.

I realized that if I wanted infinite skill-set growth and no system to hold me back, that I could make this work if I created a profitable company by the time I graduated from college. I had one year. If I’m going to be CEO one day it might as well be now.

Looking back at this rejection of the J.P. Morgan offer and starting the journey on the scrappy startup path, I now see that this was the beginning of my ability to reject a traditional hierarchical system that I used to follow so strictly. Back then, I based my personal worth on my company name and job title, and back then, it needed to be Goldman Sachs and CEO. Rejecting that value system, however, has helped me realize that my value lies in deciding what I want to do and then making it happen. I no longer had to knock on someone’s door, play by the rules, form myself into “this perfect person” with a prestigious job and title. Now, I could simply decide what I wanted to happen and then make it happen.

A week after I turned down my “dream job”, I started teaching myself static front-end web development (HTML/CSS). I made a website all about how to get top investment banking internships (because that was the only topic I could write about in great detail that would be valuable to many at the time). My first business taught students all about how to prepare for finance interviews, how to write great resumes, how to get top internships. I wrote all the content, wrote all the HTML/CSS web pages, hooked up PayPal to sell my resume review and interview prep service, then I put it online and made it a real thing.

“I no longer had to knock on someone’s door, play by the rules, form myself into “this perfect person” with a prestigious job and title. Now, I could simply decide what I wanted to happen and then make it happen.”

So, that was my first tech-enabled small business. I saw the full stack, from the web development to actually providing a service to my customers. Its growth motivated me to do something bigger and something not about finance. But I could see it now. I could see how if I made this my craft, I could make something really impactful.

Four months later, I started my first “real” tech company. The first idea that got me really excited was basically Airbnb for tourism. I wanted to build a site that sold fun and unique tour experiences like “Espresso Bar Hopping in SF’s Mission District”. I was a single founder with grit and an idea. There was an upcoming Entrepreneurship class and I decided that my goal was to take the class and make revenues by the end of the class so that I could work on this full time after graduation.

Over the course of the quarter I led a team of students. Since I was the only technical person on the team, I designed and wrote another basic website and integrated with PayPal. My team and I created real tours on campus, one was a design workshop at the D School, another was a tour of the Solar Car team’s workspace, for example. We sold our first tours and we were in business. If I recall correctly, my teacher said we were probably the first team ever to make revenues during the class in the history of the class. Shortly after, I recruited a technical co-founder and we decided to really build this as a business with the joint goal that we had to grow our revenues enough so that we could support ourselves full time after graduation.

One of the things we did was apply to Y Combinator. My co-founder was obsessed with being a “YC Company” but I didn’t really see what the hype was. I remember in our interview with Paul Graham he said, “You’re talented but I hate your idea. Change it, apply again, and we’ll accept you.” And both of us were like…hell no. We’re not changing our idea because you told us to! We’re founders!

Eventually though, as we did the math on our revenues, we realized, “Shit. We’re not going to make enough money if we don’t do something to accelerate our revenue growth ASAP.” Graduation was coming up. So, we started frantically calling tour operators, because we reasoned that if they knew how to sell tours well that we could learn a thing or two from them. This was a stressful time because I had to learn how to cold-call. I remember waking up at eight in the morning – which was an ungodly time to be awake as a student – calling these people, stuttering, and then getting hung up on. It sucked!

And then one person hung up on my co-founder, and he was fed up with it. And my co-founder said, ”You know what? I’m going to call him back. And I’m going to say, ”Don’t hung up on me, talk to me.” Ballsy, but that’s why I admired him. So he called again and the tour operator said, “You know what kid? I like you. You really want to help me? Build software for me.” We realized many of these tour operators were running their businesses on spreadsheets and whiteboards and quickly changed our pitch to cold-calling them and saying, “Hey we’re two Stanford kids who can make software for you—how much will you pay us?”

This became our new line of business. This time around, people were much more interested and some of them had such a “hair on fire need” that they wanted to meet us at 7am the very next day. We got our first customers that way and quickly made enough revenues to cover our cost of living within the first three months of running the business. I graduated, was able to move to San Francisco, pay rent. This was in 2011 and I was paying $600/mo to share a studio but you know what, I had my own company and we were killin’ it!

“I worked for a start-up for a few months, was a personal trainer for a few weeks, had many side gigs, I did a bunch of random, random things. I was searching.”

Eventually, running this business was no longer fulfilling. I realized that at the end of the day, all my efforts went towards making tourism software and helping tour operators save time and money. The day to day work was far from glamorous. Suddenly, I couldn’t see myself working on this “for the rest of my life” like I could when I first started, because we had rapidly pivoted our business into “whatever would pay us a bunch of money” without giving a care about whether this was actually the direction we wanted to take our lives. I was about 22 years old so it was great to learn this lesson early on in life. I decided I was going to leave the company and that in the future, I would very carefully choose who my customers are. Because if I’m going to spend all my time catering to their needs, I want to make a more meaningful impact at a deeply personal level.

And that was basically the end of that company (for me). A whole year went by. I worked for a start-up for a few months, was a personal trainer for a few weeks, had many side gigs, I did a bunch of random, random things. I was searching. One of the random life-changing things I did was attend Railsbridge, a free 2-day ruby on rails seminar for women. After this seminar I realized I was pretty good at Rails and wanted to really learn how to code so that I could build and test other start-up ideas rapidly.

This is how Spitfire started. It was my chosen “coding project”. I wanted to build a site called “Spitfire” that was a place where badass women could go to be with other badass women and become stronger, smarter, and inspired. There was something exciting about the identity of “a spitfire” that I captured in early versions of the site that kept me learning Ruby, Rails, Javascript, and that kept me developing the idea.

Soon, I was immersed into learning to code. Every time I would learn something new, I would add/modify Spitfire, then show it to people and ask for their thoughts. Months later, I had a mobile web strength training app that people were actually using. Since the mobile web app was so popular, I decided to make it a real native iOS app and started learning Objective-C/iOS.

“Every time VCs or investors would say things like, ‘I can’t see this being a large market,’ or otherwise express disbelief it would definitely annoy me, but not discourage me, because in my gut all of those interactions with customers that I had were just proving their opinions wrong.”

Eventually, the iOS app had about 100 people using the beta, and that’s around the time when I realized that this can be a real brand. A real business. I recruited my co-founder Nidhi Kulkarni, an extremely talented engineer from MIT who was also a D1 NCAA lightweight rower in college. I met her at a party and we connected as both women in tech and female athletes.

Soon, we had an app that was ready for submission to the App Store. This was a really exciting time because we didn’t think anything would happen. We thought it’d be a big achievement if we got 1000 of our friends to use it. But something crazy happened. Apple ended up featuring it on the front page that first week we launched, and we were stunned. We were stunned that this thing we created was viewed as good enough by Apple to be featured on the home page.

We couldn’t get any work done that day. We just kept looking at our dashboard and seeing downloads go up and up. That’s when we realized that there was something here that was much bigger than what we previously thought. This app is no longer for hardcore athletes like us. It’s a product that resonates with the everyday woman who aspires to train and develop her inner athlete. And that’s huge.

“If we don’t actually make women stronger, if our work doesn’t help instill true confidence from within, then we are failing. You have to be really careful in the health and fitness industry because if you don’t think deeply about your language, your photography, your diet recommendations, you can actually hurt and hamper people at scale and cause people to have low self esteem and eating disorders.”

We have come a long way since then. Over the last few years we raised funding from TechStars, launched a successful 179% funded Kickstarter, got featured in major news publications like Washington Post and ABC/CBS news, have recently reached our milestone of 100k users and are making our first revenues through our premium subscription offering.

Of course, those are just the successes. I’m not quite ready to discuss the hardships we have gone through at length just yet but one of the toughest years we had was 2015 when my co-founder’s mother passed away. She was with her family in New Jersey for a good chunk of that year. Our progress slowed to a crawl and I actually got pretty depressed while she was gone. So we definitely have had ups and downs.

What do you think are the biggest motivators behind your work?

I am the most motivated about building Spitfire into an eternal resource that truly helps women build their mental and physical strength and that grows into a brand that truly represents the female athlete within. If we don’t actually make women stronger, if our work doesn’t help instill true confidence from within, then we are failing. You have to be really careful in the health and fitness industry because if you don’t think deeply about your language, your photography, your diet recommendations, you can actually hurt and hamper people at scale and cause people to have low self esteem and eating disorders.

I want to help women internalize that they are strong, powerful, independent. I care a lot about that transformation and it’s both physical and mental. I view Spitfire as a vehicle to take that transformation and allow a lot of people to experience that for themselves in their own way.

“I want to help women internalize that they are strong, powerful, independent.”

We definitely have already seen the transformative effect of Spitfire on various women’s lives, but I still feel like we have a lot of work to do and a long journey ahead. This mental and physical transformation into one’s most confident and independent self is one of the most exciting things that Spitfire can offer. That’s the part of spitfire that I’m really excited about.

How did you learn not to get discouraged when people disagreed with your idea behind Spitfire?

From very early on, when I would talk to various women about Spitfire, they would just get so excited. Their eyes would light up and they would say things like, “I need that in my life! That’s for me.”

So, every time VCs or investors would say things like, “I can’t see this being a large market” or otherwise express disbelief it would definitely annoy me, but not discourage me, because in my gut all of those interactions with customers that I had were just proving their opinions wrong.

“At first, I was kind of like, ‘Oh no, he’s disagreeing! He’s a big prestigious VC and he’s disagreeing!’ And then eventually I would just conclude, ‘Wow, this guy is an idiot.’ But I would still be nice. And smile. And then eventually I just decided, ‘You know what? I’m tired of hearing this shit. I’m going to argue back and tell them that they’re wrong.’ And the first time I told a VC that he was straight out wrong, it felt so good. He was surprised. We couldn’t come to an agreement, but I felt badass as fuck for standing my ground.”

Back when I was just getting started, whenever random people said things like, “Oh, no one’s going to actually use this.” I couldn’t help but think, “Wait a second. Every single interaction and every single data point with a customer tells me otherwise.” Eventually all of those interactions and data points solidified my intuition. At first, I was kind of like, “Oh no, he’s disagreeing! He’s a big prestigious VC and he’s disagreeing!” And then eventually I would just conclude, “Wow, this guy is an idiot.” But I would still be nice. And smile. And then eventually I just decided, “You know what? I’m tired of hearing this shit. I’m going to argue back and tell them that they’re wrong.” And the first time I told a VC that he was straight out wrong, it felt so good. He was surprised. We couldn’t come to an agreement, but I felt badass as fuck for standing my ground.

How do feel like you fit into Silicon Valley culture?

I fit in well with other engineers. I enjoy meeting with the types of engineers who care about what they’re working on, who have side projects and who tinker with new technologies because they’re excited about it. Who are always building things. Trying to get better. I really get along with those types of engineers. Brogrammers—not so much.

“When it comes to venture capital, funding, large tech companies, and the ‘grow fast and become a rocket ship’ mindset, I disassociate with that and view myself as an outsider to those types of belief systems.”

I also fit in very well with the women in tech community. I see or hang out with other women and tech and have this sense of calm, I feel like, “these are my people!”

However, when it comes to venture capital, funding, large tech companies, and the “grow fast and become a rocket ship” mindset, I disassociate with that and view myself as an outsider to those types of belief systems.

It feels like there are people who work inside “big tech company” paradise, and then I view me and my co-founder as wolves on the outside, in the snow, hunting for food every day. We’re just in a very different mental and physical place.

I feel proud to say, “I learned to code and built a great product with my co-founder.” But I don’t feel like, “I’m in tech and being in this industry resonates with me.” Because it doesn’t. So that’s kind of a sensitive topic.

My identity doesn’t really lie with tech, it lies more with the strength community and especially women’s empowerment, badassery, strength training community.

I’m curious how you found strength training in the first place.

I was an avid runner in college, I ran multiple marathons and half marathons. After several knee injuries, I decided to learn how to squat. From there, I learned I really liked the weight room and how it felt to lift and build muscle. Running helped me develop the ability to endure tough times, but weight training helped me develop the ability to take on tough times with strength and power.

“It feels like there are people who work inside ‘big tech company’ paradise, and then I view me and my co-founder as wolves on the outside, in the snow, hunting for food every day. We’re just in a very different mental and physical place.”

I got into Olympic style weightlifting because a trainer at my local gym saw my potential encouraged me to compete in the sport. I didn’t even know the sport existed! “There’s a competition in two weeks, I’ll train you for free.” I learned the snatch and the clean and jerk that day and competed two weeks later. I was already able to clean and jerk my body weight and snatch 85% of my bodyweight in two weeks, so I realized I had potential to be pretty good at this sport.

I fell in love with weightlifting because I wanted to train feeling badass at every single training day. Why train to critique one’s body in a mirror when you can train to feel so good about what you just lifted and how you lifted it?

Where do you see yourself in the future?

I see Spitfire as a healthy and growing (but still young) child. I think we’re going to have a small team. We are not going to be one of those “grow as fast as possible” companies, but one that has a very clear sense of what it stands for and that forges ahead on its own and at it’s own pace. It doesn’t try to rush, or it doesn’t try to push itself when it doesn’t need to. It blossoms on it’s own so I see myself still at the helm of that, and guiding it, and working with a bigger but still tight knit team.

I believe Spitfire is going to be a brand that’s in people’s lives on a daily basis and that’s as well known but more badass and more iconic than Nike. Our presence in people’s lives is going to be positively influential and nourishing. The content that we’re going to produce, the things that we’re going to promote, it’s going to have a clear, distinct, unique identity that is really hard to copy, and I feel like people are going to try and copy it, or copy aspects of it, and they’re just not going to nail it, or they’re not going to do it right. People are going to know when it’s by Spitfire and when it’s by someone trying to be like Spitfire.

Investors will ask stuff like, “How are you going to beat Nike?” It’s funny because Nike, they’re trying to appeal to as many people as possible. But we’re speaking to one very specific thing – that inner voice in every woman that makes her feel like, “I’m a badass and I can do anything I put my mind to.”

“We are not going to be one of those ‘grow as fast as possible’ companies, but one that has a very clear sense of what it stands for and that forges ahead on its own and at it’s own pace.”

People at Nike don’t wake up every morning and think about how they’re going to achieve that. They’re in the business of clothes, shoes, and wearables. But we are going to get better and better at speaking so soulfully to women’s deep inner selves, we’re going to be a distinct persona in people’s heads and women are going to want to have a daily dose of spitfire in their lives. That is where I want to get.

Personally, I also want to be a really competitive national Olympic weightlifter. I see myself doing weight-lifting for a long time. There are some internationally competitive women in weightlifting who are in their forties right now and they’re doing amazing – and I want to be just like them. They are so happy. They are so fulfilled and kicking ass! I want to lift heavy shit. It’s funny, when weight lifting gets hard I ask myself, “Why, why do I do this?!” Well, one day I decided I was tired of being weak. And unlike many, I decided I was going to do something about it. And that’s why I’m here now.

What advice would for others wanting to build a product of their own?

When people ask me how to learn how to code, they often ask questions like – What programming language should I learn? Or what book should I read? Instead of suddenly picking a programming language I usually ask, is there something cool that you personally want to see in the world that you would love to make?

Then I say, “Okay, take that, and make it really, really, really crystal clear, and then scope it down to the most basic thing you can think of, and then learn how to code that.”

Because when you learn how to code the other way—by learning a language—you just end up reading a bunch of stuff that you don’t know how to apply. But when you have a very specific vision for what you want to build, you end up deciding what you need to know to build the thing, and you just break down the pieces.

“One day I decided I was tired of being weak. And unlike many, I decided I was going to do something about it. And that’s why I’m here now.”

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.”