I come from a big, New York City, Irish-Italian Catholic family.  I have eight older brothers and sisters and 21 nieces and nephews. I’m a bit of a black sheep in my family, politically and otherwise. I come from a very practical family of doctors and lawyers and bankers, and I was this artist and the performer. Nobody knew what I was going to end up doing including myself.

Interesting.

When I was young, I changed my mind every other day about what I was going to do, what I was going to be when I grew up. I probably stressed my parents out because they are very practically-minded. When it comes to language, they said, “Take Spanish!”, and I said, “I’m going to take French!” For a while, I majored in Art History, and my Dad recently admitted to me that he thought, “Oh my God, she’s never going to get a job.” To his credit, he never said anything at the time.

“For a while, I majored in Art History, and my Dad recently admitted to me that he thought, “Oh my God, she’s never going to get a job.””

I eventually majored in theater. It’s actually some of the most useful training that I did. You acquire an extraordinary set of skills in creating live theater. It’s highly collaborative, you have to work under stressful conditions, find ways around all kinds of constraints. It also develops your ability to empathize with other people and their stories, which is an essential skill for good design.

I definitely enjoyed the humanities and art, but I also had some interest in technology and science early on. Mostly as it related to how we can help people communicate or how can we use these tools to help people do things better and improve people’s lives. Always in an extremely applied way.

My graduate program really aligned with that kind of thinking. I was initially planning to apply to the NYU film school, but when I got the catalog, they had this program in it called the Interactive Telecommunications Program. The title sounds a bit dry, but the it ended up being a life changing experience for me. This was in 1994-95 when the web was really coming into its own, a time of really interesting experimentation. The program tries to meet at the crossroads of arts, technology, and people. It’s in NYU’s Tisch School of the Arts, so it’s kind of like a Media Lab run by poets. It’s really a remarkable place. Its student body was a mix of teachers, film-makers, policy makers, writers, journalist, artist and graphic designers. It continues to be an incredible advisory the experimentation. That’s where I taught myself how to build websites, then found myself in a startup, and a few acquisitions and 3 babies later, ended up moving to California to work for Google, then Youtube, and now at Facebook.

“I taught myself how to build websites, then found myself in a startup, and a few acquisitions and 3 babies later, ended up moving to California to work for Google, then Youtube, and now at Facebook.”

What was it like moving to Silicon Valley?

I should say I was born in Manhattan and then I grew up for chunks of time in New Jersey, Wisconsin, and Tennessee. So we moved around a lot, but all on the east coast. I never lived west of the Mississippi. I went to college in Boston, then studied art in France where I met my Canadian husband. I attended ITP in New York City, and then we got married we moved to Williamstown, Massachusetts in the Berkshire mountains where I was at a startup called Tripod. Then we moved to Boston when Tripod was acquired by Lycos. At that point, I was pregnant with my second baby, and the industry was in the doldrums. I decided to stay home for a while and we moved to North Carolina to be closer to family and live on a leaner budget. You see, at that point I had had three kids in four years and so was home full time for about four years in the middle of all of my different jobs.

And then I went back to work when my youngest was two. I joined the design team at Wachovia of all places, may it rest in peace. It was a great company to work for and a great re-entry for me after four years of being checked out and up to my eyeballs in diapers.

I had established a lot of strong relationships with designers at Wired Digital which also got acquired by Lycos. People like Jeff Veen and Doug Bowman. Extraordinary designers who also happened to be good people. They had gone to work for Google and next thing I knew, so was I, dragging my husband and kids with me.

I remember when I got the offer from Google, it was a big deal to move the family. We had a nice house. The kids were in good schools. I was close to my parents. I was agonizing over it, because I was asking my husband to quit a job he loved, which is not easy, and to move three kids. And he said, “When you get asked to pitch for the Yankees you don’t stay on the minor leagues. You must go and do this.” And that was about eight years ago. So I don’t know. I feel like it’s been an extraordinary experience because the concentration of talented, passionate people is so insanely high here. Just the level of competency and ingenuity and energy that people bring towards things is really special. And I think if I were ever to move to live some place else, I know that I would miss that.

“I remember when I got the offer from Google, it was a big deal to move the family. We had a nice house. The kids were in good schools. I was close to my parents. I was agonizing over it, because I was asking my husband to quit a job he loved, which is not easy, and to move three kids. And he said, ‘When you get asked to pitch for the Yankees you don’t stay on the minor leagues. You must go and do this.'”

For sure.

That being said, it’s also an extraordinarily work-oriented place. When I visit other places that aren’t as work-focused, I am reminded that most people don’t live their lives this way, and that there’s a certain level of sanity associated with not having everything revolve around your work. When we go back to the Berkshires in Western Massachusetts to visit friends, they don’t ask that much about Facebook, or technology, or start ups to invest in. They want to talk about art, music, go for a hike, visit a farm. I miss that sometimes.

Silicon Valley is like DC and LA. They are one industry towns, and so all of your friends are your colleagues and all of your colleagues are your friends, and even if you want to not think about work, it’s almost impossible not to. It can also be a pretty isolating place to live if you aren’t in the tech industry. There’s so much value put on tech that it almost feels that if you’re not doing that, you must not be doing something worthwhile, and that’s a shame.

So it’s a remarkable place to work. I have absolutely no regrets about being here, and I feel lucky every day to work at Facebook, a company with leaders and that I admire and respect and a mission I really believe in. AND it would be nice to have a little more balance sometimes.

“When I visit other places that aren’t as work-focused, I am reminded that most people don’t live their lives this way, and that there’s a certain level of sanity associated with not having everything revolve around your work. When we go back to the Berkshires in Western Massachusetts to visit friends, they don’t ask that much about Facebook, or technology, or start ups to invest in. They want to talk about art, music, go for a hike, visit a farm. I miss that sometimes.”

How do you think your background and life experiences have informed your work, and how you approach design at a global scale?

Well…

That’s a loaded question, I know.

Listen, I’m a well-off white person. So I feel like I need to tread carefully on saying, “My life experiences have helped me design for the entirety of humanity.” It’s a big challenge for companies like the ones that I’ve worked at to try to—with all good intentions—design for the scope and the diversity of the human population when we are so un-diverse as a workforce. That being said, there are a few things about the way I grew up that shape my perspective.

I feel like growing up in a very large family with a lot of personalities helps me to be adaptive and collaborative in a way that served me professionally. I can get along with most people. I’m just naturally inclined to figure out compromises and facilitate conversations, because that’s what you do when you have eight siblings. It’s just a basic survival tactic. Working in teams of people from different backgrounds and disciplines, these kinds of interpersonal skills are not something I take for granted, and I think I have my family to thank for a lot of that.

“Listen, I’m a well-off white person. So I feel like I need to tread carefully on saying, “My life experiences have helped me design for the entirety of humanity.” It’s a big challenge for companies like the ones that I’ve worked at to try to—with all good intentions—design for the scope and the diversity of the human population when we are so un-diverse as a workforce.”

I also really cherish my humanities and liberal arts education because I feel like it’s made me more curious and empathetic towards people with different experiences than me. I really appreciate the push towards getting more people, especially women and underrepresented minorities, into science and engineering. At the same time, I worry a bit that we are forgetting how important the humanities are to rounding out your education. Subjects like philosophy, anthropology, and psychology teach us about humans and their needs and desires. Without that training, I fear we’ll know how to build things but we may not have the compass to understand what to build and why. And that compass comes in large part through the humanities.

And obviously my training at ITP. The founder, Red Burns, was an important mentor to me. She really influenced my perspective and my philosophy on things. I don’t think I realized just how much until she passed away a few years ago. She was a total firecracker of a woman. She wasn’t that interested in the question, “What can we do with technology,” but instead asked us, “What can technology do for people?” Really putting technology in in service of people and not enslaving people to it. That’s something I really feel really passionately about.

And finally, I think that the people that you surround yourself with ultimately are the biggest influencers. My husband is a really wonderful person. Just by virtue of him, being from Canada and growing up in Quebec and just having a lot of different perspectives on things, I feel like he’s influenced my learning and development a lot over the years too. We’re celebrating our 20th wedding anniversary this year, so I’m thinking a lot about that right now. Obviously I was 12 when I got married [chuckles].

“I worry a bit that we are forgetting how important the humanities are to rounding out your education. Subjects like philosophy, anthropology, and psychology teach us about humans and their needs and desires. Without that training, I fear we’ll know how to build things but we may not have the compass to understand what to build and why.”

Obviously! As a designer, what is really exciting to you about your work? What activates you?

Something that always energies and inspires me is when I get to observe or experience the way other people live and and how those life experiences might cause them to see or value the products I build differently than I do. Years ago at Wachovia, we did a lot of research into how we could better support customers with severe visual impairments; this work was way ahead of its time. For most of us, online banking is a convenience, so we don’t have to go to the physical bank branch. But the people we met through that study couldn’t drive to a branch to take care of it themselves. For those who are blind or have seriously impaired vision, online banking is the difference between having financial independence and having to rely on someone else to do your banking for you. And the independence was crucially important to their well-being on so many levels. That made me realize something I’ve observed many times since…these technologies can mean very different things to different people depending on their context.

Most people look at Google search and think, “It’s so convenient to be able to look up whatever you want.” But, if you live in a place that doesn’t have libraries, Google in the difference between being able to educate yourself versus not. Or YouTube. Some people think of it as a place with entertaining videos, but if you live in a place that doesn’t have freedom of speech, it’s the difference between knowing what’s going on through citizen reporting or not.

I get really excited when we launch something and then get to see what people do with the things we make. When you are designing for a huge global audience, you can have a sense of what problem you are solving and try to design it in ways that will work for most people. But invariably, people will take that thing and apply it to things you never thought of. A good example is how Facebook Safety check came to being. Facebook wasn’t created as a crisis communications system, but with so many people connected on the platform, it was the natural and logical place for people to let their friends and family know they are Ok in the wake of a natural disaster or even a terrorist attack. So a team at Facebook observed this and designed not just for people but with people. I find that idea of co-designing with humanity to be really inspiring and exciting.

“When you are designing for a huge global audience, you can have a sense of what problem you are solving and try to design it in ways that will work for most people. But invariably, people will take that thing and apply it to things you never thought of. I find that idea of co-designing with humanity to be really inspiring and exciting.”

Ultimately I gravitate towards working on things that are good for the world. I know that sounds like a platitude. But I have to feel like the thing I’m working on intends to lift people up, in a very broad and democratizing way. I love breaking down the hierarchy. Whether it’s media hierarchy, or communication hierarchy, or whatever it is. I like the fact that a blind person wouldn’t have to rely on somebody to drive them to the bank. Or that a singer songwriter would be able to support themselves through YouTube videos instead of having to sign with a record label. Or that people could raise money for a cause they care about and actually move the needle on medical research like the ALS folks did on Facebook through the Ice Bucket Challenge.

Sometimes people look at what I’m working on now—digital advertising tools—and think, “Wow, you’ve gone 180 from there!” But I don’t see it that way at all. Ultimately what I’m working on now is about economic development and job creation. I think sometimes we look at the world’s problems—poverty, inequality, you name it—in very surface level ways, and what I’ve really enjoyed over past four years of working on the business side of Facebook is becoming smarter about how the world works, how society works, how the economy works and understanding that if you can help people provide for themselves, you have less war, you have less poverty, you have less terrorism, even.  

I definitely have a bit of an activist in me. I hate injustice and I hate unfairness and so I think I’ve been on this, I don’t know, 20 year voyage just trying to figure out how can design be a part of the solution. Because I feel like design is still only being applied to a very small percentage of the problems that it can solve. That’s what I’m doing more recently in my writing; just trying to encourage more designers to look past the obvious flashy thing they can be working on and think, “What could I change if I applied myself to software for the government,” or “How can design get involved in making the criminal justice more equitable and humane?” These are all design problems. They may be less sexy, behind the scenes. It’s not necessarily going to get you a big splashy article in the technology magazine, but who cares?

“I definitely have a bit of an activist in me. I hate injustice and I hate unfairness and so I think I’ve been on this, I don’t know, 20 year voyage just trying to figure out how can design be a part of the solution. Because I feel like design is still only being applied to a very small percentage of the problems that it solve.”

When did you start writing about your work?

I’ve always enjoyed writing and storytelling. As a leader, one of the most important skills is to be able to craft a narrative, a vision for what you want your team to aspire to, that captures their imagination. So in some form or another, I’ve been writing and storytelling my whole career, though I didn’t as publish my writing as much until more recently. The big driver of that was fairly practical.  We faced a big challenge a few years back attracting people to work on the business side of Facebook. It wasn’t visible to people. They knew the consumer-facing Facebook products, and that’s what most people coming in wanted to work on. I get that. And if it was visible to them, many were like, “Mmm, I don’t really want to work on ads.”

Making the work visible to people, helping them understand the impact, both on Facebook as a business and on society as a whole, how we can help improve the experience that people have at work day to day, as well as grow economies and create jobs…those were the big things that I focused on in terms of writing. About business design, and the way designers can have impact on a whole host of important issues.

Occasionally I’ll just get mad about something and write about it. A few months ago, I published an article about my uterus [chuckles]. I don’t know if you saw that.

Oh yeah [laughter]. We’re going to get to that in a minute.

I have 100 ideas of things that I’d like to write about. It frustrating to me that I haven’t succeeded in more consistently making time for it because I feel like it’s something that I’m good at, it’s something that I enjoy, and I feel a connection to people when I do it. But it’s always about capturing the time. You know how that is. I’m sure that’s how you feel about photography and other things.

“I was so frustrated and fed up on behalf of women in this industry who are trying to position themselves as equals and sometimes deserving to be seen as superior to some men in the industry, and just constantly having to pay this tax that men don’t have to pay around having talking about their personal lives. Or having it being positioned as, ‘Wow, you did all this in spite of being a mother!’ It’s just constantly minimizing their professional contributions. I don’t have any problem with anyone talking about their families and their role as a parent. But it should be on their terms, and they should never feel obligated to do it, in a context where they were asked to talk about their professional accomplishments. That’s my beef. And if you are going to ask those kinds of questions like, ‘How do you do it all?’, then ask the men too.”

Yeah, this project will very much be a snapshot of tech culture in 2016.

I’m a maker. I got into management a long time ago and realized that in the corporate context, the biggest value that I could provide is that I’m really good at building teams. So I had to let go of a lot of the hands-on contribution in the interest of making space for other people to do it. But I still have the urge, the urge to produce things, to find an outlet for that, to connect with what other people that are making and to be inspired by that. So I find different ways—you know, we have the Facebook Analog Research Lab where we print beautiful posters. I love just seeing what they’re making, and I get so excited about communication design that’s going on at Facebook. I think it’s really magical.

And then personally I do all kinds of things. I knit a lot, and I like to draw, and so writing – in addition to doing it because I think it’s really helpful to my work – is just a creative outlet for me. I never thought of myself as a writer until more recently, which is kind of interesting. I’ve always thought  of myself as a visual person or a performer, but I’ve surprised myself with how much gratification I get from writing.

Let’s talk about your uterus [laughter].

Everybody else is, why not? When I published that piece, I said to my husband something like, “At some point, I will regret making my uterus a topic of public conversation. I don’t know when it’s going to happen, but…”

You’ve written about the bias that you’ve seen on stage or at conferences. You also touched on, as you got older, you became more cognizant of bias in tech in general. Can you expand on that?

Yeah. It’s interesting, often I’ll take weeks, even months to write a complex piece about design. But with the piece about women in tech, I wrote the bulk of that in about 45 minutes at a Starbucks. I was so frustrated and fed up on behalf of women in this industry who are trying to position themselves as equals and sometimes deserving to be seen as superior to some men in the industry, and just constantly having to pay this tax that men don’t have to pay around having talking about their personal lives. Or having it being positioned as, “Wow, you did all this in spite of being a mother!” It’s just constantly minimizing their professional contributions.

I don’t have any problem with anyone talking about their families and their role as a parent. But it should be on their terms, and they should never feel obligated to do it, in a context where they were asked to talk about their professional accomplishments. That’s my beef. And if you are going to ask those kinds of questions like, “How do you do it all?”, then ask the men too.

When I published the article on Medium, I wasn’t surprised to hear from a lot of women who said it really resonated with them.  But it was really interesting to hear from many men, too, who were like, “You know what? I’m really pissed because I realized nobody ever asks me about my family. I think it’s because they think I don’t care as much about my family as my wife does.” The whole thing is dehumanizing to everyone. It’s like, “Women, all you are is a group of people who help make families, and then also could work. Men, you are people who work, and maybe you have a family.” It’s all based on really unfortunate stereotypes and doesn’t allow people to define themselves and how they want to be seen.

I also noticed in your writing that you gave people books for Christmas and I did the same thing.

Oh really?

Yes. I gave all my best friends like 10 books that affected me deeply in 2015, because last year was a year of reading self-help books and being a hermit. You also mentioned that you’re not like a huge books person. What was it about those books that impacted you so much?

Well, it’s interesting. I’ll tell you something that hardly anybody knows because I’m still processing it myself. I just got diagnosed with dyslexia a month ago [chuckles].

For real?

[laughter] My daughter has dyslexia, and when we were going through the process of getting her assessed they interviewed me and my husband. And after they interviewed me they were like, ‘’You probably have some undiagnosed issues.’’ I’ve always been a very slow reader, and I struggle to keep up with a lot of written information. I reverse things all the time and have a terrible sense of direction. There are a lot of things that in hindsight make a lot more sense. And so when they said that to me I was like, ‘’Hmm, that’s interesting.’’ I thought, ‘’I think I’m just going to get assessed, too, just to find out.’’ So I went through a formal assessment with the clinical psychologist, and boom, here I am.  

It’s kind of a wild thing to find this out a lot later than kids like my daughter discovered it. But I think you’re much better off finding that out today then when I was a kid. I don’t think people really understood it then. I think they may have thought that it was correlated with intelligence, which it isn’t at all. Maybe you get put in special ed when you didn’t need to, you just needed time accommodation. You know what I mean? I just think there’s a lot less stigma attached to it today. I see my daughter going through that. She’s like, “Yeah, it’s fine. I’m not embarrassed about it. I have a bunch of friends who are dyslexic [chuckles].” It’s like no big deal.

“If you survey successful, CEOs, there’s a disproportionate percentage of them that have dyslexia, or some kind of learning challenge. This makes sense because for those people, everything’s harder. They’re just naturally inclined to be tenacious and have grit, and to work through problems, and to recover from failure, because that’s how it is when you are a dyslexic in a world awash with written information. That whole notion of going beyond what you were born with is really appealing to me. It’s such an optimistic way of looking at human opportunity.”

I’m still processing what that means for me. But generally, I’m excited because I’m just a big believer in self-awareness and self-knowledge. If that’s true of my brain, I want to know it so that I can figure out how can I work more effectively. Just the recognition that I’m probably working X percent harder than I need to, and maybe there’s technology and tools that can help me have to work less hard at things is hopeful and liberating. I think I’ve believed in some contexts that I wasn’t as smart as the people around me, but the reality is that the mechanics of my brain were just slowing me down. I think we should all be interested in understanding how our minds work and how we can harness technology to work better.

When the psychologist asked me, “Margaret, what’s your relationship to reading?” I said, “I love stories.” She’s like, “That’s not the same thing. How do you feel about reading?” I said, “I love audiobooks.” I asked my mother one time what I used to do when I was a kid and she said, “You spent hours in your room, listening to those books that had the records that went along with them.” So interesting. Kids are amazing. They just figure out sometimes what they need even if adult don’t recognize that there’s an issue. Because one of the classic recommendation for people with dyslexia is to listen to audio versions while you’re reading the same written material. I guess I figure that out when I was three.

Anyway, I have hundreds and hundreds of books. I love stories and narrative so much, and yet reading a book just really takes me forever. If it’s not unbelievably engaging, I just don’t get through it. Which is frustrating because I’m an incredibly curious person and there’s 1,001 things I want to learn about. But I’ve found other ways to learn and grow. I don’t need to feel bad about it anymore. The reason this relates to the piece that I wrote about growth and vulnerability is two-fold; and this is so interesting in hindsight.

One is that Carol Dweck talks a lot about people with learning challenges in her book Mindset, because if you survey successful, CEOs, there’s a disproportionate percentage of them that have dyslexia, or some kind of learning challenge. This makes sense because for those people, everything’s harder. They’re just naturally inclined to be tenacious and have grit, and to work through problems, and to recover from failure, because that’s how it is when you are a dyslexic in a world awash with written information. That whole notion of going beyond what you were born with is really appealing to me. It’s such an optimistic way of looking at human opportunity.

The hardest thing sometimes is for people to get over their fear of failure, whether it’s professionally or personally. They pull punches all the time. They don’t take the risk, because they’re afraid of failing, and they miss all of the learning comes from failure. Mindset is a book that’s really been influential to me as a person, as a manager and a colleague, and as a parent, quite frankly. I really try to drive this into my kids, like, “Do your best and don’t worry about failing. I don’t actually care what classes you take, or what you study. But, don’t shy away from something because it’s hard.

And then, Brene Brown — who doesn’t love Brene Brown.

That was one of the books I gave to my friends this year.

Have you listened to any of her audio books? Her voice, her accent is just amazing. And she is so funny. But I think that book has been really influential for me, and just her teachings in general. And by the way, not coincidentally, both of those I listened as audio books. I never read the physical book [chuckle].

Funny, I think one of the things that I realized about myself, and I don’t know why this is, is that I am in a lot of ways unconcerned with admitting to my weaknesses. Sometimes it perplexes me about why people are afraid to do that. It’s absurd to think that we are all great at everything. Like its just an absurd notion, and I always tend to feel like if you own your bad PR, nobody can say anything about you that you haven’t already said about yourself. It’s very liberating.

What advice would you give to kind of young puppies starting out that you wish that you’d known in the beginning?

Take risks, especially when you’re young. You can fall down, but you won’t fall down that far because you’re already close to the ground.

[laughter]

It always makes me sad when people in early career play it too safe. I believe you can take smart risks through your entire career and most of the good things in my life have come from going with my instinct with no guarantees of success. Just figure out what’s the opportunity that’s going to challenge you and help you grow the most and not worry about the short term outcome. Because what you’re doing is you’re just building your toolkit, building your confidence, building the scenarios where you can be effective.

“It always makes me sad when people in early career play it too safe. I believe you can take smart risks through your entire career and most of the good things in my life have come from going with my instinct with no guarantees of success. Just figure out what’s the opportunity that’s going to challenge you and help you grow the most and not worry about the short term outcome. Because what you’re doing is you’re just building your toolkit, building your confidence, building the scenarios where you can be effective.”

I was born in Kansas City, Kansas, not Missouri. Very important distinction if you’re from Kansas City! I grew up with a very Midwestern lifestyle. My dad is a biologist, my mom was a nurse and a social worker—both of them super idealistic. For most of my childhood I lived on this state park, and my dad was the caretaker but also helping raise the money to permanently save the land. It was this 300-­acre plot of original prairie. A lot of my early memories were of him running this summer camp and taking care of all kinds of wild animals and running around on the prairie. I went to college at University of Kansas, so I stayed fairly local. I had planned to go to law school and follow a more idealistic path, follow in their footsteps, but ended up in college falling into video games. And that was the inflection point that changed everything.

Yeah, so you accidentally became the world’s first professional female gamer.

Yes, very accidentally. I was at the University of Kansas living in a dorm on the Honors floor. I had been elected the president of all the dorms, so I was living in this apartment, not a normal dorm room. And I was hanging out with mostly all these guys. I had always had guy friends. They were telling me about this game they were playing and they started getting me playing Doom. I loved it, so I got into Doom with them. Then they started telling me about this other game that was coming out—a sequel called Quake. When Quake came out, we all played together and we formed a clan, which is like a Quake team. We formed one of the very first clans and it was me and seven guys. To me, this was totally normal. Our clan was actually pretty competitive, and we ended up winning the very first clan tournament ever. We eventually moved into a house (though I technically didn’t live there). The eight of us were in this house just playing Quake 24/7. And, we were hosting LAN parties and having all of these people come visit us from all over the country. Other Quake clans would drive from multiple states to come play with us in person. And, this is in the days of 21 inch CRTs that were so heavy, but we were carrying them around competing and playing. So we had this whole scene going on and we all got really good. I was competitive with those guys, with one exception. We had one player who was just phenomenal, one of the best in the world.

At that time we started getting to know some of the guys in Dallas around the shooter scene there, where some of the most noteworthy teams were making first person shooter games. We started getting to know them and that included the developers of Quake. We even drove down to Dallas to talk to them in person. On one of the trips down to Dallas, a friend had met John Romero, who was a designer of Quake. This friend knew I was really good at games, and on my behalf he threw down a challenge. He told Romero, “There is this girl… she could kick your ass, and she wants to play you.”

“There was a ton of harassment and hate and sexism and abuse. People would send me hate email all the time. The emails were not just things like ‘women shouldn’t be in games,’ but very intensely personal and insulting. Every inch of my body was criticized, every aspect of my personality.”

So without my blessing and on my behalf he had thrown the gauntlet down. I had no idea if I could beat the guy or not, but over a couple of weeks we coordinated the time and we ended up going down there for this match. By the time we arrived, a lot of people in the gaming community had heard about it and there was actually gaming press there. We played at his office in Dalla s­­he was like a legend at this point ­­he was kind of a celebrity in the video gaming world. We were playing best out of three death matches and he won the first of the three, and then in the second game we were playing to 25 and he was up like 19 to 3, and I remember at that point he said something sexist. I just remember thinking that I cannot let this happen. I can’t lose. I can’t stomach what’s to come if I lose this match and all of the taunting that will come with it. I can do better than this and I’ve got to turn this around. And just like that I went on a rampage. I ended up winning that match and the next one, so I beat him the best two out of three.

After I won, it turned into “a thing” and I got a lot of coverage in gaming magazines and he had to create an online shrine to me. It just all snowballed from there. I was in gaming magazines. I got an offer of sponsorship from a competitive league to be their first full time paid cyber athlete and help this organization recruit a team of other pro video gamers. I had sponsorships from joystick companies and I got the chance to travel around the world and play in video game tournaments. It was a blast. But, it was not planned. It was very much a surprise.

What were some of the best moments of that time for you. What were your favorite things about that experience?

The thing I remember most about that experience was that it opened up the world for me. I had never been out of the country. I grew up in Kansas City and had been there pretty much my whole life until this point. It opened up all these experiences and other cultures and things I never really even knew were accessible. I got to travel to other countries and people hosted me in their homes. It was a great education. And I had never really thought, “Oh, I’d love to leave the country but it’s not possible.” It’s almost like I didn’t realize it was out there to be experienced. So for me this was an awakening and the first time that I saw the rest of the world. It was also just a surreal experience being strangely internet famous. It came with lots of pros and cons, but it was also a very unique, singular experience that not a lot of people get to have. Thanks to my internet fame, I met a lot of friends and interesting people. It connected me to the world in a way that I wouldn’t have experienced otherwise.

What were some of the tough parts and the tough lessons to learn?

The worst part was that even at that time ­ it was pre­-Facebook and pre-­Twitter and all of that ­even at that time I got a lot of harassment. There was a ton of harassment and hate and sexism and abuse. People would send me hate email all the time. The emails were not just things like “women shouldn’t be in games,” but very intensely personal and insulting. Every inch of my body was criticized, every aspect of my personality. People would dig up old pictures of me in high school and new pictures and write these elaborate multi-­page teardowns of every aspect of my being. At one point an ex-­boyfriend posted a lengthy insulting, derogatory post on one of the biggest gaming blogs at that time.

It was exhausting because it just felt like I couldn’t escape it ­even at home. I didn’t get much harassment that went beyond the digital at that point thank goodness, but I did get a few phone calls. It just started to feel like I had all of the downside of being famous without any of the upside—like money. I lost a lot of privacy. But I wasn’t really making much money. I didn’t have any of the upside or protection that comes with some types of fame. There was no real benefit to this. The benefit of connecting with people was so drowned out by how bad it felt to be in the spotlight. It really made me realize that I did not want to live like that. It was not an enjoyable way to be in the world, and it took its toll on my relationships. It just made­­ it made me view people as much more hostile than I had ever thought they might be.

“It just started to feel like I had all of the downside of being famous without any of the upside—like money. I lost a lot of privacy. But I wasn’t really making much money. I didn’t have any of the upside or protection that comes with some types of fame. There was no real benefit to this. The benefit of connecting with people was so drowned out by how bad it felt to be in the spotlight.”

Yeah, for sure. So how’d you get out?

Well, I kind of slowly backed away, you know? I quietly just backed my way out of the room. I was in a relationship—I had ended up dating that designer of Doom and Quake. We were in a relationship and we dated for five years, and it was pretty serious, but I ended up breaking up with him. And when that happened I moved to LA and away from Dallas. I took an initial job in games, but I made a conscious decision that I was going to start to look at other opportunities that would be adjacent but not directly in games. I consciously made an effort to step back from some of the press opportunities. I just slowly backed away from the attention.

It wasn’t an overnight decision. I didn’t do anything dramatic. I just felt like, “I have to get away from this, because it feels miserable and exhausting on a day-­to-­day basis.” At that time, I was working for Warner Brothers and I met this sales guy, Matt Golden, at a vendor who was selling technology to us. I was making games at WB, but Matt and I really hit it off. I thought he was great, and at one point he called me up and offered me an opportunity to take a junior sales role working for him. I’d never done sales before and I considered myself quite shy. He said, “I think I can teach you to sell, and you’ll be selling a little bit to game companies, but other companies as well.” So I jumped at that chance and that was a fork in the road for me. Ever since then, I’ve touched games, I’ve never completely left them, but I’ve never worked full-time in the industry since that point.

Was there any reaction from the community of, “Hey, where are you, we want to keep abusing you?” Or did they just move on to the next thing?

They just moved on to the next thing. I would occasionally get little pings, positive and negative. Even to this day­­ it’s hilarious to me, but even now I’ll occasionally walk into a meeting and somebody will say, “Hey, I know you. I remember who you are.” Occasionally, things will pop up online or somebody will post about me, and it’s fifty­-fifty. Sometimes it’s kind of positive and friendly and other times it’s negative and derogatory. But more than anything, the interest just faded away, and I was grateful for that. It is honestly what I was hoping would happen. It really was a gradual pulling away from the entire thing.

And now you’re an executive in technology. How did all of that experience, good and bad, inform your work now?

It informs my work in so many ways. I have been quite lucky, because that experience in gaming opened a lot of doors. It is still a great conversation starter, or sometimes it’s the reason somebody knows my name and makes a connection. So I took that baseline and went down a different path and found some great mentors. These folks taught me new skills that could build on top of my knowledge of gaming.

One of the biggest things I took away from my experience in gaming is that it was (and still is) a male-­dominated culture and industry. But I thrived in that environment and I made some great friends and connections. There were many great things about that experience, and I feel like I learned how to relate and thrive in that very male culture.

Silicon Valley (where I work now) is actually not much different. A lot of my time since those days has been in sales and business development. It is still an extremely male culture. It’s also a culture filled with highly intelligent people. Similarly, gaming culture was filled with extremely bright and passionate people. I see a lot of the similarities between those gamers that I used to socialize with and the people I sell technology to now, even if they’re not gamers. The personality types are similar, the interests are similar, and the way that I’ve been able to relate to them and gain credibility is similar.

In the end, building on that experience has been quite helpful, and it makes me feel comfortable and at ease because this is my spot. Even though I’m still often the only woman in the room, I feel like this is my place, this is what I’ve always been a part of. That comfort level was gained through my experience in gaming.

“I was going into the office everyday and like, ‘Yep, everything’s amazing and this is great and I’m here to crush it,’ and just executing on my job and nobody knew. Nobody knew that at home I had this young daughter who was crying for her dad who no longer was willing to see her, and that I was about to be evicted.”

Throughout this whole time or most of this time, you’ve been a single mom. How is that?

Being a full custody single parent is difficult, regardless of the circumstances. It is by far the hardest thing I have ever done. Trying to combine being that with being a tech executive has been incredibly challenging. All along I knew what I wanted for my daughter: I wanted to build a career that would inspire her. I also knew that I didn’t want to give myself up. I didn’t want to follow the motto of parenting that says, you dedicate all your time to your child, and you minimize time away. I wanted to have a life, too, because I wasn’t done living. My philosophy on parenting is that you build a life that shows your child how rich life can be, and how great and rewarding a career can be, and how great your friendships and relationships can be. So, I had this idea in my head of building an amazing life so she could see that and have that model. I feel like I’ve mostly done that, but it has been exceedingly hard because I feel like I have lived on a treadmill for the last decade of my life. From the second I wake up in the morning, I have a job. I have a job at home, and I’m a mom and I’m doing that and I go to work and it’s extremely intense and focused. And then I get home and I value that time at home with her so highly and I want that to be quality time. I try to give her that at the level of quality, the level of engagement that she deserves. It’s hard to succeed at that when I am so exhausted from working so hard all day at a challenging job. It’s tough, and trying to keep up the facade at work that I’m fine and I’m not exhausted and I’m not just completely run ragged is not easy.

For the first five years of single parenting, I was also extremely broke. Right after I moved to San Francisco as a newly single mom, I was about 12 hours away from being evicted from my apartment here. And it was absolutely terrifying. And yet, I was going into the office everyday and like, “Yep, everything’s amazing and this is great and I’m here to crush it,” and just executing on my job and nobody knew. Nobody knew that at home I had this young daughter who was crying for her dad who no longer was willing to see her, and that I was about to be evicted. Trying to keep up that dual existence was just incredibly hard, and I am grateful it’s easier now. But I am also acutely aware of the fight that single parents must fight. It’s not easy.

Balancing work and single parenting, I’ve often got this insanely ridiculous challenge going on at home, and yet the second I show up to work, I need to execute at a high level as if I’m just one of the other guys who’s 25 and single. Trying to maintain that level of energy, the enthusiasm, that facade that everything is fine­­ that has been the hardest part.

Where do you find you support networks? 

I am extremely independent. I’m not good at asking for help and for the first six or seven years of being a single mom, I really did not ask for help unless it was truly an emergency. I kept to myself and I did not let people help me or even know I might need help. Over the last few years, I made a conscious decision that I need to let more people in, and I have formed this amazing network of really wonderful, supportive friends. I’m working on learning to be more vulnerable and tell them when I need help. They are amazing and always show up for me. The biggest change on this front was actually just a couple of months ago. I moved my mom, who is retired, out from Kansas City and into my house. Now she’s living with us, and we have a three generation female family going on right now [chuckles]

“I am extremely independent. I’m not good at asking for help and for the first six or seven years of being a single mom, I really did not ask for help unless it was truly an emergency. I kept to myself and I did not let people help me or even know I might need help.”

Amazing. I want to go backward a little bit. Just even out of my own selfish curiosity. I deal with a tiny bit of hate that slowly increases every time I do better at something, but I’m learning to not give a shit, and I feel so much better about it since starting to learn that process and apply it. Like the fact that you have had every inch of your body criticized and yet you were able to pose for Playboy—how are you able to go from experiencing what no human really should experience in terms of humanity and then just et it roll off your back? Or does it never roll off your back?

Honestly, it never rolls off my back. As much as I wish I could tell you that I don’t give a shit, I do ­ even when I don’t want to. And it’s really hard. It still bothers me, always. I think it’s unrealistic to expect that sort of harassment or abuse to just roll off. It’s an inhumane task, and I think it puts undue pressure on the receiver of that abuse. What I’ve gotten better at is shortening the amount of time that things bother me. I give myself permission to be upset and be offended and be hurt because I deserve that. I should be offended, and it’s not OK to be treated like that. But then I make a conscious decision that continuing that letting myself feel bad any longer is actually hurting me. So there’s an end to it. I make a conscious decision to move on. I’ve accepted that this stuff is always going to bother me. I’m always going to care. I do make different decisions now, because I know the weight of online abuse. But I’m also extremely competitive, and I firmly believe that the best form of revenge or payback is simply to win. Any time I get upset, any time I’m hurt, I just let it flow through. And then I double back down and I tell myself that I’ve just got to fight through it. And there may not be an immediate victory, there may not be that sweet feeling of revenge right away or a sense that I’ve avenged a wrong. But I know that in the fullness of time, I will succeed and that that will be the proof that the critics were wrong.

“Honestly, it never rolls off my back. As much as I wish I could tell you that I don’t give a shit, I do ­ even when I don’t want to. And it’s really hard. It still bothers me, always. I think it’s unrealistic to expect that sort of harassment or abuse to just roll off.”

What would you say are your biggest motivators?

My number one motivator in life is providing a great life for my daughter. I am a big believer that providing a great life for my daughter includes living a great life myself. That central desire to show her what a great life looks like guides a lot of my decisions. It guides me to take risks and to push myself to go out and even have fun when I might be more inclined to isolate and stay at home. I don’t want her to see me as this person who just isolates and sits on the couch. That idea drives me to push myself in all areas. Beyond that, I am compelled by learning and challenging myself. I love to be challenged and to feel like I’m always growing. I know that when I feel that little hint of discomfort, that I’m probably doing the right thing. I know I’m challenging myself just a little bit in a way that I’m not comfortable with, and I like that feeling because that’s how I know I’m on to something.

How has having a kid­­ and really all of your experiences affected your priorities? Particularly in terms of what you look for in a job and future jobs?

Having a daughter has made me look at opportunities differently than I would have expected. I think I would have expected that it would make me more cautious, but having her actually has made me a little bit more of a risk taker in some ways. I feel a little more compelled to take a shot at things that might seem unattainable. There’s always this balance in my head of risk versus playing the role of the caregiver and sole breadwinner in my family, and needing to ensure our financial security. So there’s always the pull of needing to play it safe with really swinging for the fences for my daughter to watch. And usually that “swing for the fences” desire wins out. I try to push myself in that direction. I’ve never been very good about middle ground. I don’t do well in the gray area. I’m in or I’m out. I don’t like to just hang out and chill. In every role I’m in, if I’m not 100% invested and I am not in it to win it, then I might as well not be there. I’m not really capable of doing the normal 9 to 5 thing. I suppose that having my daughter has intensified both the desire for security and the desire to take risks. But that desire to take risks is the one that usually wins.

What do you love about working in tech after all these years?

I love working in tech because it forces me to be creative on a number of different planes. You have to synthesize so much information, whether it’s about technology or solutions or people. There are so many aspects to consider in a situation, and you’re often solving new problems. There’s no clean template to work from. That multifaceted challenge is what I enjoy. Most of my time in tech has been in some kind of a sales role, and usually I’m doing highly technical sales.

My job often feels like piecing together a puzzle. I love figuring out how to motivate another company with very, very intelligent employees to work with your company and use your technology. It takes more than people skills and it takes more than technical skills. The blend of those two things is really compelling for me. I feel like I’m always having to find a new strategy, and really deeply listen to people to understand how to be successful.

“I love working in tech because it forces me to be creative on a number of different planes. You have to synthesize so much information, whether it’s about technology or solutions or people. There are so many aspects to consider in a situation, and you’re often solving new problems. There’s no clean template to work from.”

Yeah. Let’s go macro for a second. How do you feel about the state of tech in 2016? What is exciting to you, what’s frustrating to you, what would you like to see change?

I think the state of tech is pretty frustrating. I don’t feel like the situation for women has improved in any meaningful way over the last few years. I see a lot of talk about it, so many tweets and posts and meetups. But my own experience has not improved in that time, and in talking to my peers and my mentors their experiences aren’t improving either. I find that really disheartening.

The reality still is that there are pockets of more diverse teams and there are pockets where there are more women. But I’m not encountering those pockets very often. It’s still a very isolating experience to be a woman in tech for me. There are some brilliant, badass women out there, but in my day-­to-­day it is rare for me to interact with women.

“It’s still a very isolating experience to be a woman in tech for me. There are some brilliant, badass women out there, but in my day-­to-­day it is rare for me to interact with women.”

I’m excited about so many of the new technologies that are being built that are going to fundamentally transform the way people live. I want to be a part of transforming peoples’ lives and making them better and easier. That’s exciting to me. What is concerning to me is the dearth of women on the teams building those technologies. Women’s needs and the way we live our lives are not necessarily taken into account in the same way when this new tech gets built. Some of that is intentional, but I think more of that exclusion is simply out of ignorance.

When people design products, they are limited by their own life experience, needs, and perceptions. It’s only natural that men would design experiences for their needs more effectively than they might design for women. I worry that as they become so much more prevalent and so much more mainstream that the divide between men’s and women’s experiences of the world is only going to get bigger.

I appreciate all of the work being done on the “pipeline problem” of bringing more women into the tech workforce. That is important work. However, I strongly believe that the pipeline is not the core problem at this point. There are some deep cultural issues we need to face as an industry to reduce churn before filling the pipe can ever be really effective.

“When people design products, they are limited by their own life experience, needs, and perceptions. It’s only natural that men would design experiences for their needs more effectively than they might design for women. I worry that as they become so much more prevalent and so much more mainstream that the divide between men’s and women’s experiences of the world is only going to get bigger.”

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

I do not think I will live in the Bay Area. I am really fortunate to own a home here, but even being in the top 1% of income earners, I struggle to maintain the type of life I want for my daughter here. It’s exceedingly hard to raise a family here. We’re failing the kids in our public schools here while rich kids just go to private school. Living in the Bay Area and working in tech feels like a treadmill that I can’t quite get off. I’m having fun; I’m still running and I’m smiling, but I’m 39 years old this year and I’m starting to think about how sustainable this is. Can I continue? Absolutely. Do I want to continue to run at this pace with so little gain? I don’t think so. I want to keep building businesses and I want to participate in this, but I also want to change the game for myself. I would love to see myself in five to ten years owning my own company, but not necessarily a venture backed company. I would love to start more of a lifestyle business that I can feel good about and believe in, but is also compatible with having a family, and having a great home life, and enjoying life. Life is short, and I want to enjoy that time and not lose my entire life to this work.

What advice would you give to young women hoping to get into tech? 

The number one piece of advice I would give to women in our position would be to be aggressive even if it is not your nature. Get out there and advocate for yourself. You don’t have to change your personality. But you do have to fight for yourself and for your outcomes. There is such a level of reward for aggressiveness and the “cult of the hustle” is so celebrated in the valley. There are some good reasons for that, because hustle is great and it gets things done and it gets you out there and gets your product out there. Relentless hustle is often required to build a successful business. And what I find is that other styles aren’t necessarily as celebrated or appreciated today in this world. Right or wrong, if you want that opportunity you have to adapt and be aggressive and hustle and put yourself out there without apologies. Don’t feel bad about it, don’t be ashamed of it. Ask yourself, “Why not me?” When you look around at different opportunities, whatever they may be, look at the people there and say, “Why not me? Why couldn’t I do that? Is there a real reason that I can’t? Is there something special about them that I don’t have?” And the truth is that almost always there’s not. There’s no reason why you can’t get there. I remind myself of that when I start feeling a little “less than.” I’m every bit as capable and intelligent as my competitors. The other thing that I try to remember is that everybody feels that level of insecurity. That is not abnormal.

“The number one piece of advice I would give to women in our position would be to be aggressive even if it is not your nature. Get out there and advocate for yourself. You don’t have to change your personality. But you do have to fight for yourself and for your outcomes.”

The truth is that we are the adults that we’ve all been waiting for. Everybody feels like they are waiting for the adults to show up, for somebody more competent or knowledgeable, but the truth is, we’re those people. You’re that person. So own it and don’t ever believe you are less than that.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Oh my gosh.

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

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

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

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

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

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

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

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

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

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

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

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

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

God.

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

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

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

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

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

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

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

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

Wow. How did you end up in tech?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

How’s your daughter liking San Francisco?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

I grew up in this really janky town called Fontana, which they nicknamed Fontucky, which pretty much sums it up. It was a really rough and tumble part of the inland empire, and I spent most of my young years there and remember it pretty fondly, although there was definitely a lot of racial tension out there.

I grew up in this really janky town called Fontana, which they nicknamed Fontucky, which pretty much sums it up.

In elementary school, we moved to this place called Chino. If you’ve ever watched the OC, Chino is “the other side of the tracks.” There were a lot of Hispanic, African American, and Asian gangs out there. I grew up really into skateboarding and punk rock, and that was my way of being outside of all that stuff. I still had a lot of friends that were involved gang different gangs and I remember seeing the older high school people get into a lot of trouble, which had a big impact on the younger generation. But also still having this thing that was my own, which was skateboarding, music, and my friends. We still got into our share of trouble, but were luckily on the edge of a lot of the really bad stuff that was happening around us.

I grew up in a musical family. My mom is a singer; she sang in church. My grandmother was a pretty amazing multi-instrumentalist back in the Philippines. She sang, played violin, and piano and all of that. My brother played music growing up; he was a pianist and violinist. My dad was a guitarist. He’d do rock and roll guitar, and was super into Santana and the Beatles. He used to play in rock bands in the Philippines and they’d ditch school just to play music and stuff which is where I got it from, the DNA. I was definitely the nerdy band kid playing saxophone in marching band, but that influenced my musical taste because I started getting more into jazz music through the saxophone.

I started playing a lot of jazz because it was stimulating for me mentally, and my curiosity was piqued the more that I got into the technical aspects of music. But then there is this raw emotional side of music that, listening to punk-rock and stuff also satisfied for me. There are two separate things that attracted me to these kind of polar opposite types of music, and I think resonated with me as this person who lived in two worlds.

Many of my friends were really into gangs and drugs, getting into a lot of trouble. I was never into that, but I definitely tagged along and got into loose mischievous things. Some of them went to jail, and it just didn’t end up well for them.

By the time I got to high school, Chino had now split into two parts, and this new city had formed called Chino Hills. It was this old part of town that used to be cow pastures and stuff, but it became this weird middle-class and yuppy part of town. But we still lived in this part that was on the outskirts, I guess, but still a part of Chino Hills. The new high school was this weird mix of suburban yuppie kids, but also other kids from Hispanic neighborhoods. Everyone from the surrounding area went there since it was the only school around. That was a funny, interesting time, because all of these other little subculture started to emerge. It’s a lot different than it is now because you had to meet people with similar interests. That’s how you discovered music and cults and all that. There wasn’t the internet or Facebook groups. I definitely gravitated toward those more outcast, black sheep type of people. I played in ska and reggae bands, and played some rockabilly music too, but still in the jazz band in high school. It was a big part of my life.

It seems like a really positive childhood experience, considering how rough it was where you grew up. Like you were super curious and hobby-focused.

Yeah, definitely—when something piques my interest I get obsessive about it, and that drives me—I get tunnel vision and that really is the thing that just encompasses all of my time. And I’d say that’s the stuff that kept me out of the really dark parts of where I grew up. Like, my parents and I were not on the same page, if you know what I mean. They’re super religious, Filipino Catholics. My brother and I weren’t super close. We’re like two totally different people. I think we were close when we were really young, but I think the older he got, like Jr high school, we didn’t really hang out at the time, because he’s 4 years older than me. By the time I got to high school, he’d graduated and he went to the military.

Many of my friends were really into gangs and drugs, getting into a lot of trouble. I was never into that, but I definitely tagged along and got into loose mischievous things. Some of them went to jail, and it just didn’t end up well for them.

Take me on the journey from that to getting into tech.

I was still really obsessed with music. I studied Jazz composition as well as recording engineering right after high school. I thought that’s what I was going to do, so I got a degree in recording engineering. After that, I started working in a small studio on Melrose. That was interesting because I was still relatively young,maybe 19, 20 when I was doing that. I was working for other artists. I was tracking their sessions and it was really weird because I think one of my main clients was this group of Pasadena Blood gangster rappers. They would pack the studio and just get insanely stoned and argue over stupid stuff. I was just not into that music. It was just a weird mix and I was like, why am I in here recording their sessions. It was still a good experience, and really good exposure to something different.

For a good three or four months, I was interviewing relentlessly. It was before web design was super prominent, so I had a physical portfolio full of books and printed pieces and I just talked to anyone that would check out my work or even give me some advice. I’d say I had maybe thirty or forty interviews in this short time span.

George Clinton was the main cash cow for the studio. Whenever he would come in, he would kick out whoever was in their at the time so they could record, but I got to spend some time in some of their sessions. Basically, they’d just get blitzed and then turn on the microphones, and then just creating this weird mix of sound that was part babble and part music. Long story short, I was about to have a kid and the music biz wasn’t cutting it. My girlfriend was 19 at the time, freshly out of high school. I was 20 or 21—and I decided that I needed to step it up. Being young and naive, I thought, “Hey, I’ll go to art school,” thinking that would be better. I went to the Art Center College of Design in Pasadena and took fine arts, printmaking, as well as environmental design. My passion in terms of design, was the built space. So once I graduated there, I was pretty adamant about not going into tech. In early 2000, web design was really hadn’t caught up to traditional forms of graphic design, and you didn’t have a lot of control. Being very classically trained as a designer, you just—in those early days—were like, “Oh, God. I don’t even want to touch the web. It’s pretty atrocious.”

I started working in the Getty Museum as an exhibition designer. I did interior architecture, environmental graphic design, and furniture. It was lots of fun working in an academic space, with very low consequences in the sense that I’m designing educational exhibits about historic art, or famous people, or just bodies of work. It was the best place for me to learn my craft and I was able to explore all different mediums. But the pay was shitty, and having a newborn child and working in a museum…I knew it would be a fun opportunity, but I couldn’t do it forever. It’s crazy for me to see people there for 10-20 years. Just thinking how they lived off that salary, because I wasn’t getting paid anything and and could’ve made more working in retail or doing something like that.

San Francisco was always a special place for me. It’s like my second home away from Los Angeles. And I’d gotten so burnt out from sitting in traffic and just grinding it out in LA, that I thought that I would try to move up to the Bay area. And once I made that decision, then I just came up here and pounded the pavement.

For a good three or four months, I was interviewing relentlessly. It was before web design was super prominent, so I had a physical portfolio full of books and printed pieces and I just talked to anyone that would check out my work or even give me some advice. I’d say I had maybe thirty or forty interviews in this short time span. Then, one of my friends that I went to school with that was a little bit older than me got a job at Google. He was the first brand guy there. So I met with him, and then I met with someone at Facebook. I think that was actually kind of serendipitous because my portfolio had nothing to do with tech, it was all environmental design. But I think some of them had gone to the Getty and seen an exhibit, and I told them that I designed it, and it was like, “Oh my God, that was a great exhibit.” I think that’s how I caught their eye, because I just applied through a random ad on some kind of job listing site. I didn’t have any ambitions of going into tech, per se, but I thought Facebook would be an interesting gig, and all the people that I met were these really idealistic young entrepreneurial types, and they really sold me on the opportunity at Facebook. All my friends were like, “Facebook sounds like a horrible job, why would you work there?” Especially going from the Getty, which is this Mecca if you’re into high design or whatever. But again, I just couldn’t live like that. It was just really bad. Facebook didn’t have a brand per say, it was much smaller than Myspace. I think Friendster was still around at that time. Honestly it just seemed a lot easier for me to get my family up here through Facebook. Also there was this opportunity to build a brand at a consumer internet company that I don’t think had really been done super successfully before then. That’s kind of what got me up to the Bay area—happenstance. Not even looking for tech, jobs but just looking for a job in a city that I was really interested in living in.

All my friends were like, “Facebook sounds like a horrible job, why would you work there?” Especially going from the Getty, which is this Mecca if you’re into high design or whatever. But again, I just couldn’t live like that. It was just really bad. Facebook didn’t have a brand per say, it was much smaller than Myspace. I think Friendster was still around at that time.

That’s cool. How big was Facebook at the time?

We had just opened our fifth office which was in New York. It was New York, Chicago, and a couple of random cities in the United States. Five offices, most of those people were sales people. So I would say it was maybe 400-500 people. In terms of design, the design team was still really small—definitely less than 10, maybe 7 or 8 people. Engineering was rather large but product design was a tiny little team.

Was your role defined as soon as you got there? Or was it just up to you?

There wasn’t a bunch of projects waiting for me there. I think I asked my manager at the time what I should be working on, and he just pointed to some people across the room and was like—“go talk to them and see what they’re doing.” He encouraged me to put myself out there and start seeing where I could dive in and have the most impact. Which was something super foreign to me because working in an exhibition design studio—especially the Getty Museum—they have their exhibits planned out probably a decade in advance to be honest with you. They’re like, we know what we’re doing 5 years from now in August. So it’s kind of like a machine there.

At Facebook I had no idea what I was doing. I knew that I would be focusing on communication design and more of the brand aspects of it, but I don’t even think we knew what that was at Facebook. It was still early in my career so I didn’t have any formulated opinions on it. It was this perfect storm of “just go with your gut and see what happens.”

Walk me through some of your projects over the course of your tech career, they vary quite a bit.

Early on, I was kind of feeling my way out through the place and understanding the identity system, which wasn’t really apparent. It was a logotype, color, and basic stuff. But it didn’t have any voice in terms of the visual identity. In fact, we intentionally didn’t have a brand voice in the early days. I worked with some of the sales and marketing teams to create some of their collateral, like brochures, little handouts for sales events. And that’s how I started—a lot of those relatively small design tasks. Working with HR to do the employee benefit packets, stuff like that. After a while I think we started to just go for it and take the reins.

The more the company grew, the more initiatives we started to realize were happening that were pretty large, at least for the company at that scale. Having some experience in environmental design, I took on some work doing their conferences. We did their first F8, which is their developer’s conference. At the time, I think they had done one already, but it was relatively small in scale, and it was almost this popup thing. We had some insight on budget, and we had some direction on the content, but for the most part we had very little oversight in terms of how it was going to manifest physically.

At Facebook I had no idea what I was doing. I knew that I would be focusing on communication design and more of the brand aspects of it, but I don’t even think we knew what that was at Facebook. It was still early in my career so I didn’t have any formulated opinions on it. It was this perfect storm of “just go with your gut and see what happens.”

So the other partner that I had at the time was this guy, Ben Barry. He and I were both similar, young and wide-eyed, hungry designers, and I think we just started making and designing and building things for this physical event. It was just the two of us alone in a warehouse with screen printing tables, assembling them ourselves, and people were just like “why are you doing that, why don’t you rent them.” And for us, no one was going to give us money to do this stuff, so we were just going to make them on the cheap, and we wanted this aesthetic to feel very DIY and handcrafted. Mainly just out of necessity, because if we had a bigger budget we would have spent more money to make it a little bit more elaborate. Most of it was just working with our hands and trying to bring this—it’s like this idea of what a hacker-based visual identity might look like. We were just trying things and making stuff. It was super fun.

For me, the biggest opportunity at Facebook was that we were building this product, but the story of the company was very focused on data, and privacy, and this young renegade CEO. Everyone forgot about what the product was enabling. Which was just communication with people and families—communities sharing information and really changing the way they they interacted.

So early on, using film was one of our easiest ways to capture a lot of those stories, document them, and get them out there. We started doing small brand video projects. Then we started doing bigger product launches and creating narrative pieces around specific products. But then we also got into documenting human stories that were on Facebook, which for me was the most fun part of being there, getting to travel and hear about these communities and different people that were doing interesting things with Facebook, in some remote part of the world. A small crew of people shooting, editing, and creating this channel to deliver stories on behalf of the brand, was a really powerful thing for me. It was this big arc for me, thinking I was going to design web pages and ultimately doing these really big brand initiatives over the course of about five years.

I think the Analog Research Lab is one of the coolest things I saw when I first visited Facebook’s campus, and you created it. How did that come about?

I mentioned the F8 conferences that we did early on — I would say that was the impetus for us to build a space to make stuff. We had this huge warehouse that was basically used for storage, and no one knew that we were in there. We just started making stuff in the corner. I think somehow we just weaseled access into the garage, and then they looked the other way and let us do whatever we wanted in there.

For me, the biggest opportunity at Facebook was that we were building this product, but the story of the company was very focused on data, and privacy, and this young renegade CEO. Everyone forgot about what the product was enabling. Which was just communication with people and families—communities sharing information and really changing the way they they interacted.

We started bringing in our own supplies. I think the Analog Research Lab started with some homemade silkscreens and some power tools that we had that was our own personal equipment. We just started making and building in the space, and accumulating equipment over time. Officially made it a thing after these F8 conferences, once people saw some of the output, then we started working out of there more and more, Ben Barry and I.

Before Ben Barry came to Facebook, he worked at a screen-printing studio in Austin called The Decoder Ring. I used to teach letterpress at Art Center before moving up here, in Pasadena. So we had this strong connection to the tactile and the physically made design stuff. And being in a world of engineers, and product, and web designers, it was a hyperdigital space. We just wanted to keep our hands dirty and still keep those skills sharp.

It was a way for us to break out of that very technological world. Then we bought some legit screen printing equipment. I found an old letterpress that I restored, and it’s still there today. We just started producing tons of hand-crafted stuff. Not just to make pretty things, but a lot of it was centered around the messages themselves. We were trying to bring the company’s values to life, but also use the lab as this provocateur inside the company. We would print posters, slogans of things that were in the air—sayings, or mantras—and we would commit them to paper.

The fact that we were using these seemingly antiquated pieces of communication technology was very subtle; but it was conceptual for us in the sense that Facebook was building this communication platform which was a paradigm shift from all the different means of communications that existed. People didn’t see it in this trajectory of human communication; from cave paintings to scribes to the Gutenberg bible. All of these things increasingly ramped up the amount of information that people were producing and consuming. Facebook is no different.

My father used to work for Pacific Bell, the telephone company. There were payphones on every street. Now that I’m an adult, you can’t even find a payphone out here. That’s how fast these communication platforms are changing. We just wanted to use the letters as a way to tie these things together. It wasn’t a project that was delivered to us or that was cued up for us. It was a passion and a very personal thing for us. That was how it took off. Once we moved to the current campus, we put it front and center. It became a landmark inside of the campus. It has a full staff now. There’s a shop manager and designers that work full time in there, but for us it was definitely a “nights and weekends” type of personally driven thing.

I love that it was a side project and it wasn’t necessarily in the realm of specialty that you were hired to work. You were pioneers for work culture that way. You guys started the posters-in-the-tech-office movement, I don’t know what else to call it. Who would have thought that something that didn’t feel necessary to a digital company or a digital product actually made ripples across all of tech?

Yeah. It’s pretty wild that now it’s all par-for-the-course, I guess. When I moved over to Pinterest, early on someone asked me, “Hey, can you make posters of some of our values?” I’m like, “No. I’m not going to do that. Not because I don’t want to do it but because I don’t think it’s what we need.” We delivered an idea because that’s what Facebook needed at the time to catalyze the culture around these things. But Pinterest was different.

I want to go into Pinterest as well, but I’m curious about something. Just hearing you talk about your work—it’s so interesting that you worked in tech at a time when specialization was important. Yet you seem to have broken those rules all over the place. It’s so interesting to me that you were so successful at that and made so many impactful projects. Did people notice that you were all over the place, and were they okay with it? I’m just so curious as to how you were able to create that path of your own when it wasn’t normal.

I don’t think at the time that people quite understood it, I don’t even think we understood it. We were just doing whatever we thought was important or whatever floated our boat at the time, I guess. I would say, in hindsight, it definitely has become a model. There were always marketing designers inside of companies, tech companies or not, but brand-focused designers were never really given the autonomy in tech companies the way that engineers and product designers were. There is still, like you mentioned, specialization. I think there are still a fair amount of generalists that they hired early on at Facebook. It could be because it was what the early team valued, and they knew that people who can do lots of different things are going to be able to move the needle more in that very malleable time. I’d say now it’s very specialized. You need to be a certain type of designer or engineer on a specific platform.

My father used to work for Pacific Bell, the telephone company. There were payphones on every street. Now that I’m an adult, you can’t even find a payphone out here. That’s how fast these communication platforms are changing.

I would say even though my work is seemingly diverse, when you look at an exhibition, or video, or whatever, a digital piece, there’s still a central trend which is around narrative and storytelling. I think that comes through in a lot of work, and being thoughtful about the strategy—if I were to describe the specialty that I bring, it’s probably more on the strategic side of brand. Most people only see the output, and they see my portfolio and they’re like, “Wow, you do all kinds of different stuff.” It’s because I don’t start with an output. I’m not a video person, I’m not an environmental designer. Those are appropriate mediums for whatever objective I’m trying to accomplish. Having that approach gave me the flexibility, but also still tied all that stuff together. Now I think there is a model for that inside of a tech company. Although I still think it’s hard for companies to kind of wrangle them in. A lot of it is about the culture and the leadership, and how willing they are to give you autonomy, which is rare for a lot of companies.

How was designing the new Facebook building with Frank Gehry?

I don’t think I’ll ever top that in my career, ever. That was the coolest thing I’ve ever done. I got to spend a lot of time with him. He’s in his 80s and he’s still the hardest working guy in the studio. He’s not doing all the grunt work, but he’s still a pretty active individual. Just being able to see the way that he works, which for me was pretty interesting, I say like most people that you think about, when they’re at a certain level like he is like, “Oh, this guy might be crazy cerebral or just really out there and different.” But he’s just the epitome of California cool, super laid back, but also still has this punk rock ethos, you know? The more people that I work with and seeing them operating at the highest level of their field—that gives me hope for our industry. Because there are definitely people that are super smart and crazy talented, but I think they make a thing out of being crazy smart and talented. Some like Frank Gehry do really cool shit, and if it fails, he’s still pushing himself to do better and more interesting and more unique stuff. That was the best part of my career.

Then you went to Pinterest.

It was just fun to get back into a smaller stage of a company, around something that was more personally relevant. A lot of the stuff I did at Facebook, from a superficial and aesthetic standpoint, probably would’ve worked better at Pinterest because it is this creative platform and there’s a lot of very specific things that we’re doing in the Analog Research Lab that actually worked well content-wise on Pinterest, like the DIY stuff. Not that I didn’t like the mission at Facebook. I think it’s pretty amazing, but being a creative individual, and going to art school, and always being connected to that, I think Pinterest brought me closer to my roots. I was around a bunch of people that were more like me.

The more people that I work with and seeing them operating at the highest level of their field—that gives me hope for our industry.

Pinterest has a much stronger personal relevance to me. I think that’s why the work that I was doing—even though it wasn’t necessarily at the scale of Facebook—there was always this this intimacy about it. It felt a little better to me because I would use this product pretty religiously.

Across your time in tech, what have been your biggest hardships and the biggest obstacles for you?

On the one hand I love the autonomy and being able to try stuff and come to the table with ideas, but I still operate in a very structured way and if I don’t have a framework, then it’s really hard for me to move forward. I think that’s what a more traditional design setting gave me. We have this exhibit going out this day, and this is the process, and it enabled me to be hyper-creative in a very streamlined way. So the lack of that has been the biggest challenge. Theoretically, I should be the one imposing that stuff, but it’s not as straightforward as that. It’s a pretty fluid, yet tumultuous environment to begin with, and each company is trying to do something different, including building the company that they want. When you bring existing processes to the table, I think it takes a lot of energy to implement those things, because everyone’s pretty reluctant to in the beginning.

When I first started at Facebook, I would find myself around people that were Ivy league or maybe had a lot of money. Part of me growing up in inland empire and the east side of Southern California just thinking, “How did I end up here?” It’s kind of crazy. It’s this conflict of money, class and upbringing that has been a weird struggle for me.

I think culturally, it’s also been a challenge. The culture of Bay Area Silicon Valley tech. I didn’t grow up like that, so I think it’s really weird for me, to be honest. Even now, having lived in the Bay Area for a good 10 years, there’s a side of me that sees all the money, and the crazy entitlement that goes around, and it really bums me out. It makes me not super excited about it anymore. It got progressively more over time, but even when I first started at Facebook, I would find myself around people that were Ivy league or maybe had a lot of money. Part of me growing up in inland empire and the east side of Southern California just thinking, “How did I end up here?” It’s kind of crazy. It’s this conflict of money, class and upbringing that has been a weird struggle for me.

You describe yourself as a broke, punk rocker from L.A. How did you fit in, or feel like you fit in, in your early days in tech and even now?

It was hard and I would say what resonated with me was the entrepreneurial spirit of early Facebook. And I think if it wasn’t Facebook, I don’t think it would have worked so well for me. Mainly because they let me explore myself creatively. Not intentionally, they just were too busy doing their own thing, and I was still producing a fair amount of work that was having some impact. I was also able to do that in a space where I didn’t have a ton of oversight, which is super rare. A lot of the great designers that I look up to, seem to have a combination either a good patron, or a studio, or a client that allows them to take those risks, and I had that at Facebook. I always use that as a benchmark which for me is not the right way to do it because all the jobs after that, I’m like “oh man at Facebook it was so different.” But I realize that it was a time in my career that I’ll probably never be able to replicate. I mean, I shouldn’t try to, I should just let these other things be themselves, you know?

The culture of Bay Area Silicon Valley tech. I didn’t grow up like that, so I think it’s really weird for me, to be honest. Even now, having lived in the Bay Area for a good 10 years, there’s a side of me that sees all the money, and the crazy entitlement that goes around, and it really bums me out. It makes me not super excited about it anymore.

I still have my family too, so that was the biggest thing because part of my life goals at the time were getting my family on their feet, and I was super determined. I think in many ways I just blocked out a lot of things. I had my eye on the prize for a long time, which was really hard to achieve, like getting out of debt, and owning a home, and the basic needs stuff. That’s really all that I cared about. I think everything else just kind of tuned out for a while.

Were you one of the first parents at Facebook?

Definitely on the design team. It wasn’t until relatively recently that those people I was on the team with at the time started having children. Only a handful of them. I still see them in my Facebook feed and they’re posting newborn photos. My daughter’s a teenager now. She spent a lot of time with me at Facebook in the early days. She would come to work with me and hang out and I would just let her run around the office. She knows Mark and Sheryl. She’s seen all those people. For all she knew at the time, they could have worked for me. I’m like “no, that young guy over there is the boss of all of this stuff.”

I tend to work early. I would take the Caltrain and get there super early in the morning. Sometimes at 6:00, 7:00 in the morning and be the first one there for a good 2 hours. But then people would want to meet at 6:00 at night. I’m like, “I got to go home. I got to eat dinner with the family,” and that was a struggle. But I didn’t feel like it was too much of a compromise. Everyone’s like, “why does he always leave early?” It wasn’t super early, it was just normal time, but they were a young crew of people that worked super-late. Now they know because they’re all having little babies and they’re like, “This is so hard,” and I’m like, “No shit, try doing it when you don’t have the financial means and the support network!”

How do your friends and family from home feel about the work you’ve done and how you turned out?

I think my parents are proud. Just being at Facebook, they assume that I’m a billionaire.

It’s a weird environment. And I think if you don’t live in the Bay Area or work in tech it’s so foreign. Even being inside of it you’re just like, “What is happening?” It’s such a weird thing. Each company is different and there’s all these different groups of people. Someone will write a book about this someday—but at this point in time, you kinda gotta be here to experience it.

Where do you see yourself in five or ten years? Do you see yourself still working in tech?

I don’t know if I see myself working in tech. My goal is definitely to have my own design practice. In five years my daughter will be in college, which, for me is crazy because we don’t have another kid and I’ll still be 40 years old. Relatively young in the sense of having a child that’s already out of the nest. That for me is pretty exciting, because we basically did our family life backwards. We had a kid early. We kind of grinded it out at work and got on our feet as a family. I didn’t spend my 20s dicking around going to clubs and stuff. Now I’m able to go out without freaking out about a babysitter. I’m starting to experience the city from a young adult’s eyes versus a parent’s eye, which is a new thing for my wife and I. If I’m able to travel and still have my own clientele and do stuff, that would be pretty amazing. I can’t say I won’t be in tech because I think most people are somehow tangentially connected to tech. Even if you’re freelancing as a designer, you might have a tech client, because that’s the predominant industry paying good money. I do see myself doing more music. That’s been number one on my list, trying to get a group people playing again. Also, doing more makerly things, like furniture design. Or make something physical and tangible versus working on a computer.

What advice would you have for people from similar backgrounds who are hoping to get into tech?

I guess the philosophical side of me is saying: First examine your motives. Sometimes a problem isn’t in the motive, but in the fact that you have a motive at all. And I think for me, just being able to navigate these really weird situations at times, was because I felt like a conscious observer and I was trying to be really objective towards things. But I think, had I come in with a goal being monetary or superficial stuff, then I don’t know if tech would have worked well for me. So that’s probably my first advice, which I don’t even know if that’s advice. But if you’re following tech because that’s where the money is, or that’s seemingly the most fluid and flexible work environment, I’d say all of those things are superficial. Examine what it is that really motivates you and see how tech either gets you closer to that or doesn’t, and make a real decision.

Someone will write a book about this someday—but at this point in time, you kinda gotta be here to experience it.

I come from North Carolina. I grew up in a small town, Teachey, North Carolina, about 45 minutes from Wilmington, NC. Population: 200. I grew up doing a lot of farming, working the fields, tobacco cropping and things of that nature. But I had a passion for art and drawing. I was an artist. I used to draw on classmates clothes. I used to do paintings. Initially, I got into computer graphic design.

So you were a creative kid growing up. I’m impressed that you found that so early. I’m from New Bern, so I know what it’s like growing up in a tiny North Carolina town. I had no exposure to the word “creativity” until I moved to Raleigh.

Wow!

What was it like being a creative kid in the small-town South?

It was fun. I can’t remember what drew me to art and drawing, but it was something I just seemed to like to do. Like every kid, of course, I played sports, but I knew I liked to draw. I knew I wanted to paint. You know, every entrepreneur has a story about, “Oh, I used to sell lemonade in the neighborhood.” I think everybody has a great story around that, but for me, I used to draw on people’s clothes like graffiti or the Super Mario Brothers character or their initials, and that was my hustle. That was my side project. It was how I brought a little extra money for school shopping. Growing that’s what I did, and eventually, that was the beginning of my tech career. After high school, I was like, “What am I going to do?” I went to a one-year school for computer graphic design and ended up doing that and getting a job at the Jacksonville Daily News Paper for computer graphic design. An area which you know about, Jacksonville, NC.

“I feel like it’s rooted in my blood and my history to be a connector. Being someone who brings communities together.”

I know Jacksonville very well. I grew up 45 minutes from it.

I worked about four years at The Jacksonville Daily News. Two years where I was doing graphic design, newspaper ads and then two years in IT. I started doing desktop support and to show my age, I used to go to people’s houses with a floppy disk to set them up with dial-up networking. So I feel like it’s rooted in my blood and my history to be a connector. Being someone who brings communities together.

Yeah. So, when I first connected with you and discovered you seven or eight years ago, you were deep in the North Carolina tech scene in Raleigh and I was just a bartender who happened to like tech. You were one of the first people I discovered when I found Twitter and that whole network of techies in North Carolina. What was the North Carolina tech scene like at that time?

I moved to Raleigh in 1998 from Teachey, NC  and that’s the beginning of the end of the first dot-com bubble. Raleigh-Durham and The Research Triangle Park and that whole area were like, “We are Silicon Valley 2.0.”  The tech scene at that time had Sony Ericsson, Cisco, SASS, all these tech companies.  When the crash happened, it hit the NC community harder than other tech communities because it didn’t have the wealth to put back into the community like Silicon Valley has. A lot of entrepreneurs just didn’t survive. Innovation and the tech ecosystem wasn’t thriving and growing. It just came back to sports and universities. I felt like, “Wow, there’s still a lot of opportunities here, there’s a lot of community here, but we’re not coming together.” That was the beginning of blogging. That was the beginning of blogger meet-ups and then tweet-ups. Twitter launched in 2006. I was one of the first 1000 users to join Twitter. Then we started seeing the beginning of the web 2.0 movement. People were like, “Everything’s a fad.” I’m like, “No, this is great! It’s now connecting us with people all over the world. We can build relationships; we can create communities and awareness.” I started connecting with people at NC State and then we  began doing blogger meet-ups. Me being a geek, a nerd and working IT, I was into everything tech. I was reading everything that happened in Silicon Valley and the Bay Area. I’m like, “We can replicate—at least from an event standpoint—what they’re doing over there in Boulder too. So the community started growing. There were a lot of people like my friend Ryan who’s at IBM. Another friend who was at an interactive agency, Kipp, who’s now the CMO of Hub Spot. We have another friend Jeff, who was working at a marketing agency. Now he’s a professor—I think in Chicago—teaching social media and business.

“When the crash happened, it hit the NC community harder than other tech communities because it didn’t have the wealth to put back into the community like Silicon Valley has. A lot of entrepreneurs just didn’t survive.”

We all came together and just started doing these events and replicating from content and an event standpoint what we saw in Boulder and Silicon Valley, like Ignite events. The community started growing and surprised some, but when you think about it,  it made sense because the universities and Research Triangle Park had an active iPhone development community. There were a lot of IOS developers who were one of the first teams to make a million dollars on the app store. Just like even today, there’s a Bitcoin community in the area. So the tech community was thriving, all the pieces were there, but we all came together to start making the events more community focused.

Walk me down that path from doing all this great work in the Raleigh tech scene to then moving to Silicon Valley and making moves there. What was the impetus for moving across the country to build something on your own?

So if I’m 100% honest, when I was saying that I was reading all of the blogs and reading everything that was happening in Silicon Valley, there was some jealousy there. Being a geek and being a nerd, you want to be a part of the energy. You want to be a part of what’s happening in tech. I’m not a person that’s a big fan of tradition or stereotypes, or being put in a box. I’m just like, if they can do it, I can do it too, right? That’s how I think and operate. And so, I got fed up for a while. I was just doing a lot of work in NC and a colleague reached out to me. He was like, “Let’s build this mobile app. It’s similar to Foursquare but just for the Raleigh-Durham area, we called it TriOut.

“Being a geek and being a nerd, you want to be a part of the energy. You want to be a part of what’s happening in tech. I’m not a person that’s a big fan of tradition or stereotypes, or being put in a box. I’m just like, if they can do it, I can do it too, right? That’s how I think and operate.”

I remember that.

Yeah, one of the few people. And so we came together, we launched the TriOut iPhone app and a social network. So from 2009 to 2011, that was what we did. We were a startup in the area, one of the few tech startups. And we grew the platform, the service, and had a lot of great support from small businesses, but even in that time the companies were not ready for location-based platforms or using a mobile app to reach the customers. Most of the businesses were not even embracing Twitter and Facebook, much less a mobile app. That took a lot of work and energy out of us, knocking on doors of businesses and trying to grow the startup in the area. We did get some interest from investors, but we ended up selling the platform technology to NC State University.

“We received tons of crazy press. We were in CNN’s documentary Blacks In America. CNN created some controversy, but we had people talking, and the show inspired thousands. Because for the first time, you saw African-Americans and women and minorities on TV doing tech startups. It wasn’t that common; African-Americans were like, ‘what’s that?’ They didn’t think it was for them because we just didn’t have the exposure and lack of role models in the tech industry.”

In 2011, the data came out that only 1% of tech startups are founded by an underrepresented individual and by that time I’m like, I’m part of that  1%. I know how hard it is. I’ve been in tech my whole life, what else can I do to learn but also educate others to be more successful. So I partnered with a colleague of mine, Angela Benton, and we had an idea for a startup house helping unrepresented entrepreneurs go to Silicon Valley for the summer. It would be a mix of the real world meets the social network, and we pivoted and just created an incubator-accelerator and moved to Silicon Valley for four months. That was the birth of NewME. We received tons of crazy press. We were in CNN’s documentary Blacks In America. CNN created some controversy, but we had people talking, and the show inspired thousands. Because for the first time, you saw African-Americans and women and minorities on TV doing tech startups. It wasn’t that common; African-Americans were like, “what’s that?” They didn’t think it was for them because we just didn’t have the exposure and lack of role models in the tech industry. So I officially made that move in 2012 from North Carolina to San Francisco.

What were your first impressions of Silicon Valley like? What were you expecting and how was it similar or different to those expectations?

I haven’t been asked that question that way before. When we moved to Mountain View, I was expecting Mountain View to be more like how San Francisco is now. That was the first impression. I also was surprised how everything closed around 9 o’clock. Isn’t this Silicon Valley; this is where things are happening. I thought people would stay up and work all night at coffee shops. No, everybody’s gone at nine. So I was like, “Hmm. Surprising.” Later I learned most of the developers were hacker houses.

There was no Helio’s (a coworking cafe we both frequented in Raleigh) open ’til midnight.

No, there’s no Cafe Helio’s in Mountain View. But one of the biggest surprises that is still relevant to this day was that people say how competitive it is as a tech entrepreneur. It is very competitive, especially when you’re trying to raise capital. Everybody is trying to reach the same 50 to 100, 200 investors. But overall, because of the density of entrepreneurs, everybody’s willing to help. That was surprising because in North Carolina there was only a small hub of entrepreneurs, the same thing in Durham. In Chapel Hill, there’s community around UNC, but it’s so competitive because everybody’s trying to fight for those smaller amounts of investment and there’s a limited awareness of community. So that was surprising, like wow, there’s so many people that want to help you. It was also surprising as I learned about how the ecosystem operated, how people may or may not help you.  If you are working on something world changing, if you are cool, if you are getting into the right circles, if you are drama free. You know what I’m saying, if you’re a signal that the ecosystem measures entrepreneurs by.

When you got here, what was the community of underrepresented entrepreneurs like? How did people form support networks at the time and what were some of the biggest issues they were facing?

When we first came to Silicon Valley, people had started reading about us in the news. We were in the Wall Street Journal. We were in a CNN documentary, and then because of our relationships using social media, we had a network. We weren’t starting from zero, which was very, very helpful and valuable. When we came to San Francisco, there was an organization called Black Founders. They held a welcome brunch for us. When we got here, we were already working with Mitch and Freada Kapor. They were mentors and speakers in our program. We were connected to Ken Colemen, another was a mentor, Stephen Adams, who had been out in Silicon Valley for 20 years. These individuals who have been here, they were opening doors and embracing us, and that was important. It felt right because we came from North Carolina, and I was too surprised also. Everybody knows that there’s a sense of a problem that there’s a lack of diversity in tech. And some people have been out here for years who have made a lot of success for themselves and their network, but it hasn’t been pushed to the forefront of the conversation. And I was surprised why has that been the case. If you’re here, why hasn’t there been more effort? I was surprised about that. At the same time, I started understanding why, because there are unspoken rules that you don’t talk about race in tech. Because of the false belief of meritocracy. You don’t speak of culture because it’s the good old boys who work and the create the culture, it works, so why to change it. You don’t fit in. You’re not a culture fit. I started seeing how these communities operated.

Regardless, the community embraced us, but not everyone. Some people told me; “Don’t come out here and mess it up for us.” “I’ve got it good right now. I made it. Don’t screw it up for me.” Which is unfortunate, but I get it. So it was good and bad.

“I started understanding why, because there are unspoken rules that you don’t talk about race in tech. Because of the false belief of meritocracy. You don’t speak of culture because it’s the good old boys who work and the create the culture, it works, so why to change it. You don’t fit in. You’re not a culture fit. I started seeing how these communities operated.”

What have been some of the most exciting parts of building an incubator and building conferences? What has been some of the most fulfilling parts of that work for you?

Hearing the stories later. That has been some of the most inspirational aspects of this all. I do this work because I love it. I do this because it’s needed. I do it because I want to leave a legacy for my son, and he says, “Well, my daddy is doing this, and he did it for me.”  And I care! I’ve traveled to speak at conferences in Detroit and Atlanta and abroad, and you hear entrepreneurs and individuals say, “You know what, I read about you, and that inspired me to get into tech now. And now I’m working for this hedge fund.” Or, “Now I’m doing this startup.” Or, “Now I’m doing this.” Or, “I saw you on TV, I read this article, and now I’m hosting this event.” That is the most exciting part. It’s also un-measurable in some sense because you don’t know all the people you can reach or who’s watching you. You see the work you’re doing and hope for that they can learn and get inspired for themselves. So that has been the most valuable. And then there’re the other tangible aspects of it where somebody got a job through an introduction or someone met a co-founder or  some serendipitous meeting happened because of the work we’ve been doing. And then, of course, there’s the one where people just created a team, and they’re raising money because you introduced them to the right investor and so forth.

“I do this work because I love it. I do this because it’s needed. I do it because I want to leave a legacy for my son, and he says, ‘Well, my daddy is doing this, and he did it for me.'”

What personally has been the most challenging thing or the biggest hurdles for you as an entrepreneur?

Being an entrepreneur but also coming from North Carolina and being black, I still deal with confidence and credibility. I still deal with the fact that I didn’t go to an Ivy League school. I haven’t created a product that millions of people have tested or downloaded. I haven’t raised millions of dollars. I haven’t had an exit or created a 100x opportunity for an investor. I deal with imposter syndrome. Those things are all signals in Silicon Valley and tech people look at those terms of success metrics. That doesn’t mean it’s right, right? It’s just their signals in Silicon Valley / Bay Area, the system that’s been established. But those signals play in the back of my mind where even today,I was talking to my partner. She was like, “I don’t have to live up to those standards, and I don’t have to get those individuals approval, right? Who are they, and why should I be trying to get their approval or live under their standards? I don’t have to seek to get in that particular network. The work I’m doing is just as important or more and what I’m doing has better values and integrity.” So the biggest challenge is most definitely the confidence and dealing with credibility despite all the work and success I’ve had so far.

“Coming from North Carolina and being black, I still deal with confidence and credibility. I still deal with the fact that I didn’t go to an Ivy League school. I haven’t created a product that millions of people have tested or downloaded. I haven’t raised millions of dollars. I haven’t had an exit or created a 100x opportunity for an investor. I deal with imposter syndrome.”

Yeah, I feel like one of the biggest moments for me in the last few years was having this moment where I was like, “Oh, I don’t have to please and get approval from every single person. It’s a waste of time. It’s unproductive.”

Yes, and now I learned to stop caring about what other people think. Now I focus on being happy and what that means. Being happy with just yourself and being aware of how you think, having a cognitive awareness of how you process your thoughts, your emotions. Being inspirational to yourself and how you think and how you feel, thinking “You know what? I’m happy, I’m healthy,” and like you said not trying to please everyone.

“I learned to stop caring about what other people think. Now I focus on being happy and what that means.”

Have you had mentors or people that you’ve looked up to for inspiration or  people who have been pivotal in your career along the way?

Yes, one I mentioned earlier was Steve Adams. He’s  the entrepreneur at Heart also. Been in Silicon Valley for around 20 plus years, and raised over 20 or 40 million dollars over his career. He’s an African-American guy who pulled me along the side and just really has helped coach me and advise me on life. Sometimes it’s been about a product I’ve built but most times the feedback has been about my life. Another person is, Shellye Archambeau, who’s the CEO of MetricStream. Shellye is an inspirational mentor where she drops those little nuggets, life lessons like, “Keep doing what you’re doing. I believe in you, keep writing, keep story-telling, keep me updated.” Because all those things were a sign that someone cares, right? Another mentor is Cedric Brown. He’s also from North Carolina. He went to UNC, and he works with Kapor Capital For Social Impact. We have lunch every couple of months in Oakland and really just talk about life and relationships. Those individuals are people I call mentors but also friends, and it took a while for me to develop those relationships. There’s  also Steve Blank. Steve Blank is a guy who everybody knows in entrepreneurship tech. I got a chance to build a relationship over a two or three year period with Steve. I’ve been to his house a couple of times and talked about entrepreneurship, and he gets it. Being able to leverage his brand, his name and path to my career has been key. Also Kathleen Warner and Kelly Hoey, who both are on the East Coast, these two amazing ladies who I’ve met over my career, they get it, they care, and they just want to see good people win. It’s been good to be able to have those individuals in my life.

You’re from a tiny town. When I meet people who are from tiny towns in the South, I’m like, “Oh my god, you got out too, that’s crazy!” [laughter]  So I’m curious to know, where do you think you got those entrepreneurial qualities like that appetite for risk and the drive, where do you think that came from?

It originates from both sides of my parents. I look at my father. He and I spent a lot of time working on cars. That’s what we do in the South, right? We worked on engines; we worked on go-carts. We just like to build things with our hands, so I think that’s where the artistic side of me came from, but for me it was computers. My mom used to work for the government. She worked for HUD, the state, and always had that kind of entrepreneurship drive and spirit. She’s now had her own business in Teachey for ten, maybe fifteen years now. When she started, I helped her when it was a print business. Then she got into insurance and taxes, and it’s been her business for years. The house is paid for, and they are doing well in the South.

So I got that drive from both of them. When I look at my grandfather on my mother’s side, he died before I was born, he was a police officer. My great-aunt was a school teacher on my mom’s side. And my grandfather on my father’s side was an entrepreneur.  I remember going out with him; he used to take me to the farm. That was my summer job. I would work in a field all day starting around 6 am until like 3 o’clock, and we’d go to the farmers market and sell the vegetables, and he’d give me five dollars. I’d be like, “That’s all I get?”

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

With my immediate family, I have two sisters, a younger and an older sister. They all get it. My parents, they get it. I was always pushing tech on them.  “Hey, do this, sign-up for that.” I set up my moms’ network at her home office. Her home office network was better than the local town’s network, with more computers and printers. I would say that they are happy for me. It’s been tough because a lot of African American families—and people in the South, no matter what race, they don’t leave their hometown that often. They don’t go too far.

“It’s been tough because a lot of African American families—and people in the South, no matter what race, they don’t leave their hometown that often. They don’t go too far.”

At times, when I come home to visit, they sit watching TV. I’m like, “What are we doing?”. One of the things I remember  my first cousin telling me. We all have family who have been in and out of jail or things of that nature. He’s a cousin  who now is getting his life together, who’s working,  but he told me” You’ve  got to keep doing what you’re doing.” He’s like, “I tell my friends I’ve got that cousin who’s out in Silicon Valley who works with Google and all these other big tech companies. He’s out there making a name for himself.” For him to say that, inspires me to keep doing what I’m doing because he didn’t think that it was an opportunity for him, and you don’t see that many African Americans in tech.  I have a Slack group called BlackMenInTech.com, with about 300 black guys from across the country who work at Google, Facebook, Uber, etc. Some are entrepreneurs; some live in the midwest. We had a guy in the Slack group who lives in Cleveland, Ohio. He was like: “Wow. I didn’t know there were this many black guys working in tech.” Because if you are in Cleveland, Ohio or New Bern, North Carolina, and you read all the news you’d think it was just all white guys. You wouldn’t know that there’s any diversity out here at all. So the work that we all are doing is important,  these stories that you are doing are important.

“If you are in Cleveland, Ohio or New Bern, North Carolina, and you read all the news you’d think it was just all white guys. You wouldn’t know that there’s any diversity out here at all. So the work that we all are doing is important.”

It’s one of the biggest drivers of this project because I think people are going to come to this and for the first time see people that look like them and who are from where they’re from. I think so many people have no idea that Silicon Valley is even an option for them because they’ve never seen anyone like them in it. That’s a problem.

Or they don’t see any women. They don’t see any women in various roles. Women in leadership or women CEOs and technical positions, or even the fact that you can just create a real business using technology. It doesn’t have to be trying to go to IPO. It doesn’t have to be the next Instagram or whatever, but just great business. It’s getting so bad that the narrative out there is  that you can’t just live here and be happy [chuckles].

In the last few years, how have you seen tech culture change, particularly in being more accommodating to people of color. How has it changed, and/or has it gotten worse? How about right now in 2016?

Harvard Business Review and Fortune Magazine began publishing articles on diversity programs, and how they are not inclusive of white men and how white men are starting to fear a more diverse workforce and fearful of losing job opportunities. Then you start seeing these posts on income inequality from super well-known rich investors. Then stories about income inequality became a hot topic. I began to think that people with money who have been making money in tech, which has primarily been white males are now looking at this change regarding diversity inclusion and income inequality, computer science for everybody, and saying that “Isn’t it starting to level the playing field?” You look at all these VC posts and all these subtle changes, then the monopoly and the control they’ve been having, the power they’ve been having over who gets funded, how they get funded and controlling the market. It’s going to impact how they get access to early deals and opportunities to create wealth for them. That insinuates fear, and that bothers me because when people start taking emotional actions around fear where they don’t want change, that mindset is going to hurt everyone.  That bothers me.

“You look at all these VC posts and all these subtle changes, then the monopoly and the control they’ve been having, the power they’ve been having over who gets funded, how they get funded and controlling the market. It’s going to impact how they get access to early deals and opportunities to create wealth for them. That insinuates fear, and that bothers me because when people start taking emotional actions around fear where they don’t want change, that mindset is going to hurt everyone.”

That’s just one case, and it’s why we need inclusion in tech. We need to show that diversity is good for the world and good for the American economy. We need to do what we can to close the wealth-access gap. Because that whole economy is going to crash if we don’t.

Whoa, that is blowing my mind for second right now, the idea that diversification of entrepreneurship makes VCs lives harder because it messes with the system they’ve built and optimized for.

Yeah, [chuckles]. It’s an uncertain outlook, but if you look at how things are being portrayed, that’s what’s happening, right?

Yeah. Absolutely. That’s a major thing, and well-founded. This is the year of VCs biting their tongue, that’s for sure.

I know, right? But the good side of it is the fact that these stories are now being told, people are taking action. With action comes accountability, with awareness comes responsibility, more resources towards education. People are starting to care more. We call it a tech business, but everything we do affects people. We have to care more about people no matter what race, what gender, ethnicity, or religion. We have to look at ways of how we can create wealth because tech is one of the only industries in the world where we don’t have to go to a four-year university to get a job, even though that’s where the bar is set with ivy league schools, right? You can come into tech; you can learn to code or be great at project management, or have the right passion and get a job,to create wealth and impact not only in your life, but your family’s life. We need to do that with the income gap,  the education gap,  the average salary gap, and the unemployment gap. We need more people in tech from all races, genders, and cultures.

Personally, how do you think tech can be more accommodating to underrepresented entrepreneurs in the industry?

For me, I believe tech can be more accommodating when we look at the workforce. We need people who care in leadership and are who are held accountable. They are in positions that can be nonthreatening or non-bias towards diverse individuals. I think that’s some of the hardest problems we’re facing right now, that a lot of the workforce is only 2% black, 1% Latino, about 11% women. How did that happen? That’s just the workforce. People have to care and be accountable, and they haven’t been. If they were, it wouldn’t be as it is. For entrepreneurs, it’s going to come down to the biases that investors have regarding what makes a successful team because it’s not just the money, right? It’s the opportunity they get. It’s the chance to test your hypothesis to see if this problem that you’re solving has a particular value. Everybody doesn’t get that opportunity. Because even if you get the money,  then it’s the mentorship, it’s the relationship, it’s the open doors, the partnerships, everything that comes with the relationship with investors.

I see so many great entrepreneurs who work their asses off. But it’s everything else. They get special access because they’re in a particular network, but if you don’t fit a particular stereotype, you don’t get that same opportunity. We need to change that in entrepreneurship. At the same time, I can’t speak for the Latino culture because I’m not Latino, but for the African American culture, we also need to look internally, look at our culture and how can we change our priorities. How can we change our focus? Regarding where I grew up, yes I got into art, but it was all about Michael Jordan, it was all about Michael Jackson, it was all about Eddie Murphy, and the comedians. That’s why we have this next generation of Kevin Harts, and just repeat, repeat, repeat. We’re in 2016; now we need more role models in tech. We also need  to disrupt the African American culture and our values, get focused on creating wealth. That’s not on the street, it’s not on the court, it’s not on the stage.

“Regarding where I grew up, yes I got into art, but it was all about Michael Jordan, it was all about Michael Jackson, it was all about Eddie Murphy, and the comedians. That’s why we have this next generation of Kevin Harts, and just repeat, repeat, repeat. We’re in 2016; now we need more role models in tech. We also need  to disrupt the African American culture and our values, get focused on creating wealth. That’s not on the street, it’s not on the court, it’s not on the stage.”

What are you working on right now? Either for others or yourself?

You made me pause because you said for myself and I’m like, what do I do for myself? [chuckles]

Right. I know the feeling.

For me, I just really like being healthy. Being healthy and happy. Being fit is also part of the San Francisco culture. But I just really like being happy and healthy, emotionally, intellectually, and also physically. That’s taking care of yourself, as number one.

Yeah. It’s hard to prioritize, isn’t it? Honestly. I finally figured it out this year, but I sympathize with people who can’t figure out how to make that work because they’re trying to make it work career or money-wise.

It’s hard to balance. Professionally I did a lot of cool projects over years. In 2014 I created a non-profit BUILDUP. In 2015 my partner, Melinda Epler and I started Tech Inclusion because we had begun seeing all the conversations around diversity and inclusion in tech, but most of the conversation are around the problems. We were like, we know too many people who do amazing work, but they don’t know each other. We also know a lot of the new diversity hires, a lot of individuals having this conversation, but they are not connected. Everybody was looking for solutions. We thought” how can we bring people together?” So we created the Tech Inclusion conference in 2015 and recently announced a new partnership with Google For Entrepreneurs; and we’re going to have the conference in New York and San Francisco. We hope to create opportunities and the spaces to solve these problems.

Where do you see yourself in five or ten years? Do you think you’ll still be in tech and what kind of problems do you see yourself solving?

I’m always going to be in Tech. So I pause, and I laugh because I’m like—where I see myself in five years could depend on how the presidential race goes in 2016, and where I am in the country or out of the country. Regardless, in five years, I hope to continue to support the early stage entrepreneurs, and my passion is to have a venture fund one day. I’m going to put myself in the position to be on that path. Maybe get into education by teaching, and I still have some aspirations for entrepreneurship—a couple of ideas.  I have asthma, so I want to do something in asthma and biotech.

My last question for you is: what advice would you give to folks from similar backgrounds as you who are hoping to get into tech? What do you wish you’d known in the beginning?

My advice is to keep learning. There’s a book called Mindset, by Carol Dweck and I think everybody should read it because it’s about knowing the difference between a growth mindset and a fixed mindset. If you have a growth mindset, you can learn anything and have the confidence to complete your goals. I think that’s like number one. Number two, believe that no door is closed. If you just learn how things work, you can open any door. Number three is to travel. If I never got outside of Raleigh, I  wouldn’t be in San Francisco today. So, travel the world, get out of the country, get your passport and just go!  Learn, see the world, build relationships and then be mindful that we have so many ways of communicating today. Create a real strategic plan of how you are going to communicate with your network. This sounds so basic, but in this world, if you put out positive energy, put out to the world that you are somebody and want to help others, it will come back to you. You just have to continue to put out positive energy. Last, build something. Whether your build a product,  a community,  a service,your network,  your intellect, build something!

“In this world, if you put out positive energy, put out to the world that you are somebody and want to help others, it will come back to you. You just have to continue to put out positive energy.”

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

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

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

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

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

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

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

What originally brought you to Silicon Valley?

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

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

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

What are some of the proudest moments of your career?

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

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

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

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

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

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

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

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

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

What have been some of your biggest struggles and roadblocks?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

How do you find balance between the two?

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

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

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

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

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

What do you enjoy most about it?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

I was born in Seattle, but my dad was in the navy so we moved around a bit. When I was 8, we moved to the Philippines where I lived for 15 years, so I pretty much grew up there.

What was it like growing up there? Especially as someone who had a taste of the States.

It was difficult at first because I didn’t speak Filipino, so I had a tutor to learn it. It was weird at first because obviously I look Filipino, but other kids treated me differently because I didn’t speak the language and I sounded different.  But I was young so I adjusted quickly. I started college when I was 16 and majored in Computer Science.  The plan was always to come back to U.S after we graduate, but I had a little detour. 

In my senior year, I had an unplanned pregnancy. It was really difficult being in a Catholic university in a conservative and predominantly-Catholic country.  I felt like I disappointed my parents and was a cause of embarrassment in the family.  I was a good kid, I had good grades and a good life, I just made a bad decision.  I was fortunate that my mom really pushed for me to finish college.  A lot of other girls in the same situation would have dropped out of school because the family wouldn’t be able to face that embarrassment. I got married then a few months later I had my daughter.

“In my senior year, I had an unplanned pregnancy. It was really difficult being in a Catholic university in a conservative and predominantly-Catholic country.  I felt like I disappointed my parents and was a cause of embarrassment in the family.  I was a good kid, I had good grades and a good life, I just made a bad decision.”

I had to postpone a final project presentation because she arrived 2 weeks early.    Because I was busy with my senior year, I didn’t have time to attend childbirth classes or read books.  I didn’t even know an epidural existed until years later!  A week after giving birth, I had to go back to school for final exams. I wasn’t planning on attending graduation but I found out that I graduated cum laude and actually 3rd in my class. My parents attended and they were happy and proud of me.

After graduation, my husband and I each moved back with our parents. My parents offered to look after my daughter so I could work.  My mom was a stay-at-home mom and didn’t get to use her Engineering degree and she said “I want you to have a career.”  But in the small hometown where we lived, there were no software jobs.  This was back in 1999 and unless you lived in Manila, there wasn’t much to do with a CS degree.  

Not that I had the time or energy to really think about my career. I was pretty much in survival mode and all I needed was a job so i can feed my baby. I got a job teaching at a small technical college and after a semester, I worked for another company but didn’t really use much related to CS.  My husband and I split up in the meantime.  It was a lot of stress for a young marriage.  

What did you do to try to turn things around?

After my daughter turned 2, I decided it was time to come back to the US to find a better job.  My sister was kind enough to lend me money for a one-way ticket to Texas where she and my other sister lived.  The hardest part was leaving my daughter with my parents.  But I had to until I could find a job and be able to afford to support the both of us.  It was pretty scary. It was 2001 during a recession and it was hard to find a job.  I had a few temp jobs doing random things, like sorting mail and data entry.  Finally, a small software company hired me to do customer service. I was able to save some money, and after 7 months of being apart, my parents brought my daughter here. I stayed at that company for 7 years, and I went from customer service to QA.  In the middle of this, I remarried then after 3 years got divorced to get out of an unhealthy relationship.  On top of that I had $24,000 in debt.  I really made all my stupid decisions in my 20s. 

“After my daughter turned 2, I decided it was time to come back to the US to find a better job.  My sister was kind enough to lend me money for a one-way ticket to Texas where she and my other sister lived.  The hardest part was leaving my daughter with my parents.  But I had to until I could find a job and be able to afford to support the both of us.”

I then moved to a big semiconductor company where I stayed for 4 years. My life started stabilizing in my 30s.  It took me 2 years to get completely get out of debt.  I was making better money.  And I was in a healthy relationship.  After Thanksgiving in 2012, most of our business unit got laid off. It was my first time to experience this. It was scary especially being in a single income household.  

All these years I was in a career crisis. I didn’t really know what I wanted to be when I grow up [chuckle]. I always hear “follow your passion” but this was never clear to me.  I have a lot of things I’m interested in but none that I’m both passionate about and am good enough at to make a living.  If I had followed that advice, I’d probably be a failed travel blogger. So back to getting laid off.  Part of our package was tuition reimbursement. The idea was for the company to pay for you to acquire some skill to get a new job. It wasn’t enough money to get a new degree and believe it or not, I used to dream up my ideal job and think, if only I studied to become a lawyer or an accountant! In the end, I thought, okay, practically speaking, with this amount, what can I do?  Well, I have a CS degree and I haven’t written a single line of code since I graduated so maybe I should learn a new language.  I searched for the top jobs in my field.  I looked at jobs at Google, Amazon, and Apple, and I was just curious, what kind of skills are they looking for?  Long story short, I signed up for an online Python class.   It was difficult at first to get started, but I realized that the concepts that I knew were the same, just the syntax was different.  It was like falling in love again!  It was exciting solving each problem, the same feeling I had solving problems in BASIC when I was 9, and Pascal in college.

In the meantime, Amazon had contacted me and many of my co-workers through LinkedIn because a lot of the skills we had in embedded software were what they were looking for.  I went for the interview thinking, “This is really going to be a practice interview. There’s no way I’m moving to California.” [chuckle].  I got a job offer, and it was compelling enough for me to consider it. It was a hard decision to leave my support system, and move to a place that I’ve never been to before where the cost of living is just so high.  

The move turned out to be the best thing that happened to my career!  I continued learning Python and applying it at work.  I found that the better I got, the more I felt enjoyment and passion in my work. The move also turned out to be great for my daughter, being able to play in one of the top high school drum lines in the US. She cried at first because she would be leaving friends and going to a new high school.  But she said, “If you think that’s what best for us, then I will support you.”  

Like a little adult.

Yeah. I think because it’s just the two of us, I tend to talk with her about everything, including finances. So she understood why we made the move.  Anyway, I feel like I have so much energy and desire to learn new things.  Next year she’ll be off to college so I’ll even have more time to focus and go on to the next phase of my career.

What a story. What overall is the most exciting to you about working in tech? What things are you really proud of and what about the work really activates you?

What I love about working in tech is being able to work on products that change people’s lives.  I read the reviews on Amazon Echo and it’s amazing to see how customers use device, especially disabled people.  It’s pretty exciting and inspiring.

People are speculating that technology like the Echo is the future.

Yes it’s very exciting to be part of that!

I’m curious to know what it was like culturally going from the Philippines to Texas, then from Texas to Silicon Valley.

Culturally, going from the Philippines to Texas was a breath of fresh air for me.  In the Philippines there was such a stigma of being a single parent.  You and your child get either judged or pitied on.  Hopefully things have changed there since then.  Regarding moving from Dallas to the Bay Area, I love the culture of learning and trying to be the best at what you do.  There are so many movements, organizations, meet ups in tech that it’s not hard for the enthusiasm to rub off on you.  I’m not saying it didn’t exist in Dallas, but maybe I just was not in that environment.

What has your experience been work-wise as a single mother?

The biggest difference for me is not being able to travel for business.  It has to be planned and I could only go if I had someone I trusted, like my parents, to look after my child.  I think that being a parent is hard whether you’re a single parent or part of a two-parent household.  As far as my daily work, when my daughter was younger, I had to force myself to be efficient because I didn’t have the luxury of staying extra hours if I didn’t manage my time well.  

What’s it been like, leaving your support network in Texas, and then trying to find support networks here?  Have you found them yet?

It was difficult leaving my family and friends. I’m a bit towards the introverted side, so it took effort and courage to put myself out there and make new friends.  I mentioned that my daughter is in the drum line at her school’s marching band.  Volunteering for that enabled me to meet other parents who were very welcoming.  It definitely involved getting out of my comfort zone.

“I always come across difficult problems to solve at work.  But they’re almost never as bad as the difficult problems I’ve had to face in life.”

Have you had any particular mentors in your career?

Yes, in Texas I had a good manager who mentored me when I was new to QA.  I’ve also had several good managers since I moved here.  One managed me remotely from Seattle and he always talked about improving my skills thinking not just about my current company but for my future career.  I thought that was kind of refreshing. Maybe that was another one of those cultural differences back in Dallas where I didn’t feel like I could be that open with my managers about my career because if it may not line up with what is best for their team.  You have this fear of being the first to go in a layoff if they knew you had any thoughts about leaving.  Here, no one expects you to stay in one place for 10 years, or even 5 years, so you can be much more open.  

It’s like to keep you, they have to nurture that.

Exactly. Having a good manager is important to me, so when I interview, I make sure it goes both ways.  

What do you look for in a job now compared to earlier in your career?

I look for somewhere where I can add value to team or company, in an environment that supports autonomy and creativity. It would be great to work on something that customers love, and I can say, “I worked on that!”  

How do your friends and family feel about how far you’ve come?

My parents were always supportive of me and cheered me on every step forward I made.  Today, I feel that I’ve made my parents proud.   My daughter always thanks me for being a great mom.  That means a lot to me. 

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

I always come across difficult problems to solve at work.  But they’re almost never as bad as the difficult problems I’ve had to face in life.  I also am not confused anymore about what I want to do with my career.  Getting rid of that lingering doubt helps me focus better.   

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

I think the Connected Home and Internet-of-Things will be big this year.  I’m excited to be part of that.  But I think it will be important for people to distinguish between the ones that improve your quality of life and others that are just innovation for innovation’s sake.  

Technology aside, I see a lot of exciting and frustrating moments about improving diversity in tech.  Women in Tech in particular is close to my heart, having a daughter who is exploring careers and deciding what to major in.  I see a lot of movement around this and I feel hopeful.  She took Java programming this year at school to test the waters and see if she liked it enough to minor in Computer Science.  She had a good experience and now she is thinking about majoring in it.  She might still change mind of course, but my hope is for her to experience a more gender-diverse tech world than I did.  

What are your goals for 2016? Either for work or for yourself.

I have a lot of goals.  At the start of each year, I write my goals for the year  and I like to revisit it throughout the year to see if I’m making progress.  The career goal I set for myself this year was to switch roles from a QA Engineer to a Software Development Engineer in Test.  I talked with my manager about it and I’m happy to say that I am working on that transition now.  My personal goals involve getting better at programming, reading more, traveling more, living healthier, watching more concerts, getting back into playing the drums and maybe even playing in a band!

Where do you see yourself in five or ten years?

I would love to be a software developer and build something.  In 10 years, I’d love to be able to at the top of my industry.  I don’t know what that will look like yet.  Maybe those jobs don’t even exist yet, just like many of the tech jobs now didn’t exist 10 years ago.

My last question for you would be, what advice would you have for folks that are going through some hardships, or had crazy life obstacles thrown at them and are trying to figure out their career?

Have a goal, make a plan and focus on the process of getting there.  There are times when life is crazy that you don’t have the time or energy to even focus on your career.  But it’s not always going to be a hardship.  Set realistic expectations given the situation that you currently have.  For example, when the kids are young and you don’t have help, maybe all you can focus on is raising them and doing “good enough” at your job.  Accept that that’s where you are right now.  They will get more independent as they grow, and you can execute on your plan one little step at a time.  Manage your time well.  We all only have 24 hours in a day.  Figure out what’s important to you.  For me, getting 8 hours of sleep is priority.  If you feel like you never have the time or energy, try to identify and fix the unimportant things that suck up your time, or things that cause you stress.  It might be debt, health, relationship stress.  Read books and learn from other people on how to deal with these problems.  There’s no need to learn all of life’s lessons the hard way.  It makes it easier to work on your career when you can lessen or eliminate other stresses in your life.  Lastly, for parents, don’t let your life revolve around your children.  They will turn 18, graduate and be on their own. Don’t forget to treat yourself with love and kindness.

“Have a goal, make a plan and focus on the process of getting there.  There are times when life is crazy that you don’t have the time or energy to even focus on your career.  But it’s not always going to be a hardship.”

I grew up in the Santa Cruz Mountains. I have three sisters. I come from very old-fashioned Italian background. I wasn’t encouraged to do a lot in terms of career. It’s kind of the mindset that you get married, you have kids, you stay home or get a small job, but your husband has the main job role. That’s what you do.

I ended up going down a path that wasn’t necessarily… I guess the word I’m looking for is fulfilling. I got married at twenty-three, had my son at twenty-five, and became an aesthetician. Though I was grateful for my job, it was not stimulating, and financially, it was not fulfilling. I wanted to also be an inspiration for my son. How could I tell him to do all these things, like learn how to code and that tech was the future, when I wasn’t going down that path myself?

“I got married at twenty-three, had my son at twenty-five, and became an aesthetician. Though I was grateful for my job, it was not stimulating, and financially, it was not fulfilling. I wanted to also be an inspiration for my son. How could I tell him to do all these things, like learn how to code and that tech was the future, when I wasn’t going down that path myself?”

One day, I re-applied to college. I majored in Communications, since I knew I was good at that, even though I knew I wanted to do so much more. I started taking classes through the University of Massachusetts. I did all my classes online, and after I accumulated enough credits, I was accepted into the bachelor program. I looked at the program and realized this would take me years to complete. As a mother in her mid-thirties, I didn’t have the luxury of time that someone in their early twenties may have. I needed to figure out a different path. I started looking into internships, and found an internship with a PR company. The woman who hired me was named Xinea. Through her, I was exposed to tech startups and Bitcoin. I worked with her for a few months, and then I got a call from Facebook. I interviewed, but did not expect to actually get the job offer. Surprisingly, they offered me a position with the Ads department. It just seemed like everything I was aiming for just kept happening—which, I don’t how that happened, but it worked out.

At Facebook, I worked on a tool that enables you to customize what kind of ads come into your feed. While I was there I took advantage of many of the programs they offered to their employees: They offered some free coding programs, like a PHP coding program for just women. It was my first experience even using the command line. I didn’t even know what Terminal was, let alone PHP or Python. Being able to see that you can manipulate or create tools using these languages was just very exciting. I eventually looked into different coding boot camps. I looked into Hackbright, an all-coding female boot camp. I attempted to start my application, and then I stopped; I saw the acceptance rate was about four percent. Because I thought, ”I’m a parent, I’m a wife, I’m in my thirties. I have no business doing this. I don’t know anything technical to be able to say that I want to be a software engineer.” I put that on hold for about a year. I started looking outside of Facebook for jobs, because I was really interested in engineering, but also more of the security aspect of it. I found a job with WhiteHat Security; the position was in marketing, which is fine.

I still felt like there was a part of the tech world that I wanted to be in, but I didn’t feel that I had that traditional background to get there. I didn’t go to a major big-name school; I didn’t have a computer science degree; I was in my later thirties; and I had children. It just seemed like everything that was supposed to have already happened, I missed out on. I talked to my husband, who was very supportive. He’s a self-taught security professional and one of the most intelligent people I know. He helped when I felt like giving up. He encouraged me to apply for Hackbright. He kept me going.

“I attempted to start my application, and then I stopped; I saw the acceptance rate was about four percent. Because I thought, ”I’m a parent, I’m a wife, I’m in my thirties. I have no business doing this. I don’t know anything technical to be able to say that I want to be a software engineer.'”

Initially, I did not get in. I received a email that said I was not accepted and to try again in six months. I just felt that if I lost this opportunity, I would lose it forever. This was my moment. I wrote them an email and I said, “I was so nervous on my interview, I did not represent myself in a way that truly conveyed who I am. Please give me another chance.” They wrote me back, and they said, “We have never allowed anyone to re-do an interview. But your email was so encouraging that we are going to allow you to interview again.”

My second interview was much better and I was accepted! Once I started my cohort, I still felt a little bit like a fish out of water, but it was understanding the technology and understanding what it is that they teach women that don’t know anything about software development. You can come in to Hackbright with a background in tech, or you can come in knowing nothing. That’s basically where I came in, I was starting from the ground up.

After I graduated, I went through many interviews. I was going through multiple software engineering position interviews, but I still felt that I wanted to to pursue security. I found an opening at Lending Club and it was through a network of people I knew. They offered me a position on the Application Security team. Now, two weeks into it, I am an Application Security Engineer. I was an aesthetician [laughs]. It’s so random and exciting.

Tell me more about the challenges of getting to this point—like you commuted four hours a day. What were some of the challenges of this experience, and the hardships that you had to overcome?

I had mentioned before that when I first started becoming interested in learning how to code, I had a very limited technical background. I was not a IT or Comp. Sci major that decided, “Oh, I think I want to be a software engineer.” I started asking some of the engineers at Facebook about how I can learn how to code and what is it like to have that job. The one engineer who would sit next to me was very encouraging. He would say, “It takes a lot of practice” and offer to show me how he fixes bugs in the code. Not everyone is that encouraging or helpful unfortunately.

We had an event at Facebook, and it was an Ads event to teach people in other departments what the Ads team does. The event had a Game of Thrones theme, which I was very excited about. I remember talking to someone from another team. I wanted to ask about the code but was slightly intimidated since I was very new to the world of code. So I got the courage and I said, “So what code does this code run on?” And there was a female engineer there and she turned to me and she just laughed in my face. She just laughed at me because I wasn’t part of that group, I was not an engineer, and obviously a noob. At that moment, I realized that high school was never over.

“I remember talking to someone from another team. I wanted to ask about the code but was slightly intimidated since I was very new to the world of code. So I got the courage and I said, ‘So what code does this code run on?’ And there was a female engineer there and she turned to me and she just laughed in my face. She just laughed at me because I wasn’t part of that group, I was not an engineer, and obviously a noob. At that moment, I realized that high school was never over.”

Aside from my own personal challenges, I also had the challenge of maintaining my family life as well. I knew that once I started my four hour a day commute, it would be a difficult to find someone to pick up my son from the school bus. I have two other step-children, so there’s three kids altogether that need to be cared for. Fortunately, between my husband and family—and sometimes I would even have to leave class and do pick up—we worked it out.  I would get home at 8:00 or 8:30. The kids go to bed at 9:30. I wouldn’t see them very much, but fortunately they were all understanding. It was hard to feel so out of touch with my family but I felt it was important to do this for myself—and also for the kids. They need to see the importance of not giving up and hopefully the importance of learning how to code.

What are some of the most exciting things to you of working in tech and coding? What part of the work really activates you?

My first week at my new job, we all had a one-week bootcamp to get us to understand how the technology department operates. We went over everything from setting up dev environments to database schemas. I was in these classes with people who went to big colleges or had years of experiences or master degrees in computer science. Seeing that I was able to contribute to the conversations—and even knew about some topics that maybe some of them didn’t—felt really good. It reminded me that I had made the right choice to quit my job and take that chance. Understanding technology and knowing a coding language really gives you magic powers. It’s like being Harry Potter. You have a power that not many people do. And I think for me, I feel more excited about it because it was something that three years ago I wouldn’t have been able to say that I would be able to do this. It’s all still very surreal.

“Understanding technology and knowing a coding language really gives you magic powers. It’s like being Harry Potter. You have a power that not many people do.”

What are the biggest motivators behind your work?

My husband first, then the kids. My husband is very encouraging to me and that in turn motivates me. I want him to see that I can go from knowing so little, to having tech-related conversations without any issue. Tech is his world and I want to join him and be part of it. Steve would be proud of anything I do, but it makes me happy that I am joining him in “The Matrix.”

We tell the kids that coding is very important to learn. I feel it’s important for the future for people to understand how to code and being in tune with technology. We sent the kids to coding classes. I wanted them to see me making that effort to learn the topic that we preach about so often.

Lastly, I am motivated by becoming an inspiration for someone else who is in a similar situation. I started taking phone calls for people that are interested in Hackbright or another coding bootcamp, people who maybe aren’t sure about the commitment. I actually just got an email today from one young lady who said, “I really appreciate that you encouraged me and told me the benefits of going down this path. I was just accepted to Hackbright!” You get to the point when you’re older that you realize there are things that, if you want to do them you’re going to have to sacrifice. I didn’t want to take no for an answer. I didn’t want to say my time is up. I wanted to be part of the Harry Potter group and know the magic.

Where have you found support networks along the way? Obviously your family, but have you found them in the industry as well?

I found most of my support through co-workers in the security industry. I had some mentors, and they’re all men, which I love, because I feel that a lot of women want to be in the industry: They want to be software engineers, they want to be QA testers, they want to be in security, but the ratio is more men. I’m the only female on my team right now, which could make people uncomfortable. I am very comfortable with it and I don’t even think about the ratio. Maybe others don’t feel that they have that support, but I actually feel that I have had a lot of support.

How do your family and friends from your past feel about how much your life has changed and all the work that you’ve done?

I have a coworker, Katie, that still can’t believe that I’ve made it to this point, because she said—her and I, we took a Python class together at Facebook—”I can’t believe it. You said you wanted to do this and here you are and you’re working. You’re an engineer.” She gave up on learning Python. It wasn’t for her, but it was nice of her to congratulate and be supportive. Honestly, I don’t know if my family quite grasps what it is that I do. I think they get it, but not really. They are extremely supportive in knowing that I wanted to do something and achieved it, but I am not sure they understand the job.

How do you think the culmination of your background and your life experiences impact the way you approach your work as an engineer?

Starting my first tech job made me feel like a fish out of water. I felt like I knew nothing. So to survive one day at a time I used my experience in marketing, PR, just working with people in general. This is a huge asset to have. If I came straight from just a tech background, you know I went for a tech major and maybe I didn’t have that interpersonal skills, it wouldn’t make it as easy for me to just go up to someone and say, “I’m not really getting this, but, with your help I may.” I feel that my communication skills have come into play and I feel it is something that can really help the team when working with other teams and developers.

As far as 2016 goals, what little things are you working on right now, either for work or for yourself? Like what are the things you want to accomplish this year?

2016 goals are learn as much as I can about being an applications security engineer. Understanding the vulnerabilities, understanding how to secure code and understanding all the acronyms that I hear during the day. It’s all new to me. Lending Club gave me an opportunity to learn, and I’m going to run with that. I want to still practice everything I learned at Hackbright because that was the golden ticket that got me in. I also would like to continue to help other women that are in the same place that I was in. I had moments of serious doubt and I can’t believe I thought about not taking this chance. If I could help sway more women to trust in themselves and just go for it, that would be wonderful.

From kind of a high level, how do you feel about the state of technology in 2016? What really excites you, and what would you like to see change?

That’s a good question. I am very impressed with the way that technology is progressing. I like the ideas. I like that there’s always something new. It’s hard to keep up, I have to say. You think you have found the best tool to help with a current project, and then something new and more advanced comes out. I really enjoy that and love seeing the speed of progression. The amount of intelligence out there right now, even just in Silicon Valley is huge. I work with so many insanely intelligent people which has me very excited about the future and what is to come.

As far as what I would like to see change, right now, and it has been for the last couple years when I’ve been working, my goal has been to get into security. Rewind a little bit, when I was at Facebook, I knew I wanted to get into security. I had no idea how to do it. This is before even seriously considering Hackbright. I went to Jen Henley, who is the director of security operations at Facebook, and she sat down with me and just kind of gave me a guide on what to do to get into security. I started volunteering with their security awareness events, and then I went to work for WhiteHat Security. My husband is in security, and so by osmosis, I learned to love it. I think that it is an area of technology that is overseen. People are looking for the next best company, the next best app, but they’re not looking at the dangers that are involved in it. They are not taking the time to understand all the possible vulnerabilities and how they can be exploited. All of our lives are on technology. Everything important to you in online, your information, your personal lives, your photos, your family, and if someone’s not out there protecting that then all is lost.

What advice would you give to folks who are feeling like they have similar backgrounds to yours? Maybe they feel like their ship has sailed, they’ve had kids, they are in their thirties, they feel like that there’s no way that they could get into tech now, but they would love to. What advice would you have for those folks?

My advice is, time is going to pass anyway. Someone told me this a couple years ago and it resonated with me. It’s true. Time is going to pass anyway, and you don’t want to go down the road and think, “You know, I wish I did x, y, z.” For me, I went to a start-up convention and I just looked around and saw these people making these exciting new tech tools to improve our everyday life and I just thought, I need to know this, I want to be part of this.

If someone is working in a position and they’re unfulfilled or dream of changing positions and making a career change, and they think, “I’m too old or I have kids, I can’t do it,” then my advice is that time is going to pass regardless, and you don’t want to regret it not taking that chance. You only have one life.

You could go down it by going through a boot camp. You could look at CodeAcademy or, just take a Girl Develop It class for beginners. Start somewhere and I promise the momentum will take you the rest of the way. I took some online courses and GDI classes before I went to Hackbright. Just getting that little bit of experience is enough to drive you to continue on and finish the journey. I went from what I was doing—aesthetician work at ten dollars an hour a couple days a week—to a great job as an Associate Application Security Engineer. It was not an easy journey. I got denied a lot. I interviewed a lot, I got turned down a lot. My path was not paved with open doors. I faced a lot of disappointment in all phases of my journey. It worked out, and I would say don’t get discouraged. Just keep going, because it’ll happen.