I was formed in a culture clash. I’m first generation Eurasian—Czech, Filipina, Taiwanese—and was raised in a small hippie town founded by an Indian guru in Iowa. Fitting in was never a possibility; I spent my childhood hoping to be noticed for something else other than being different.

What was family life like? What did your family expect of you career-wise?

When I was thirteen my father took a trip to the east coast and brought me back a Harvard t-shirt. As the eldest of four, I bore the brunt of his immigrant dreams. Thankfully he was more of a “follow your passion” type guy than one who pushed for law or medicine.

My biological mother hails from a rural village in the Philippines and was the first in her family to finish high school and go to college. When she obtained a PhD and position at MIT, she cemented a place in the provincial hall of fame. I don’t know much else about who she is unfortunately. She died in a car accident when I was young, but even her ghost is hard to live up to.

“Fitting in was never a possibility; I spent my childhood hoping to be noticed for something else other than being different.”

My father is a kooky but brilliant underachiever, a renaissance man who possesses that rare blend of a critical mind and creative talents which he channels into architecture, art, philosophy, and poetry, and deftly speaks at least five languages. He has an anti-authority streak, refusing to work for anyone else and only at his own whim.

His lack of material success is an endless source of frustration for him, and seems to only be redeemable by his children’s. He taught us to read as toddlers and multiplication in kindergarten, and hoped that this would set us on a trajectory for life. My (half) siblings are in their twenties and are wonderful people with musical abilities, artistic talents, keen minds, and sensitive hearts. So maybe he was right.

I can’t imagine my potential career ever entered my stepmother’s mind; she didn’t care for me much as I was a reminder of the woman before her. As for my father, what I did or was didn’t seem to matter to him as long as I made him look good.

What did you think you were going to be when you grew up?

When I was a child I had no sense of future; I just wanted to read and climb trees. As a teenager I lived to travel and got any and all odd jobs to make it happen. The world was a wondrous place of beautiful landscapes and art with fascinating history, and full of unique people. When my grandmother described the life of an ambassador, I set my heart on it, and actually chose Tufts for their International Relations program. Politics lost its allure quickly though, and I ended up majoring in Anthropology.

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

For the first decade and change of my career, I helped foster communities around tech products, namely Yelp and Airbnb. I’d have to credit my childhood experience as part of a meditation community in Iowa as being the most enlightening case study on how to create a movement. I experienced first hand what motivates and inspires people to give their time, resources, and hearts to a cause; How hierarchy and different power structures influences people’s drive and sense of ownership; The ways that norms are reinforced and what happens when people act out; What to do when the message gets out of hand. Life lessons for me.

How did you first get interested in tech?

I’m compelled by how tech allows people to live more enriching, fulfilling lives. The idea of “tech” didn’t initially interest me. I used Napster, ICQ, and ebay in college, but never gave much thought to actually working in the sector. In fact, had you asked me then I was totally ignorant of the fact that from the ashes dot com bust interesting companies were emerging. But I’ve never been someone who’s motivated by contributing to cutting-edge technical developments. I often wish I had a more visionary bent.

“We landed in SF with a cell phone, $300 bucks, and a backpack full of sarongs. Every day for the first two weeks we set up shop selling sarongs on Haight Street and trolling Craigslist for opps. I went through a series of odd jobs: pyramid schemes selling office supplies, handling boa constrictors, trimming weed, data entry.”

How’d you end up in SF and in tech?

In 2004 after college I sold all my worldly possessions and moved to Bali, Indonesia. It was first put on the map by my midwife “auntie” who opens birthing centers in developing countries. After a few months traipsing around the island and bumming around on the beach with my then-boyfriend, we ran out of money. I had no interest in going back to Boston, so when he suggested we go to SF because of the great house scene (we both fancied ourselves aspiring DJs) I agreed despite having never been to the city. I knew one person from my hometown living there and she offered up her couch to us as a temporary crash pad.

So we landed in SF with a cell phone, $300 bucks, and a backpack full of sarongs.

Every day for the first two weeks we set up shop selling sarongs on Haight Street and trolling Craigslist for opps. I went through a series of odd jobs: pyramid schemes selling office supplies, handling boa constrictors, trimming weed, data entry. Until I landed a temp job at a commercial property insurance company. I was so happy to have regular income, it took me a year to realize that the agency had been taking an unfair cut.

I ended up in tech by sweet serendipity. First, I randomly saw Yelp paraphernalia on the bus and later found out that I shared a route with the graphic designer. Then I got a Daily Candy newsletter sponsored by Yelp. Being new to the city, I was curious about places to go and badly needed friends. So when I visited the site and saw several hundred people yapping about things to see and eat, I got hooked. I discovered some great places through the site and shared my reviews in return. The marketing director, Nish Nadaraja, took notice and invited me to one of the first Yelp events ever, at a place restaurant called Oola on Folsom.

“For weeks after, I emailed any and all contacts at Yelp in hopes of getting a job. They were like, ‘Can you code? No? Sorry, we’ve got nothing for you.’ But a few months after, they posted for an Office / HR Manager and I jumped on it.”

I wasn’t quite sure what to expect, so I put on my best tweed blazer and flared jeans (gah!) and dragged my then-boyfriend along to the party. I had prepared myself for an awkward experience, but when I saw Jane Kwett, a face I recognized from the site at the door I was put at ease. Entering the party and plied with a cocktail, I was thrilled to meet all the characters I’d be interacting with online in 3D. Everyone was welcoming, clever, and slightly nerdy, and I immediately felt like I wanted to be part of their tribe.

That night, I met the CEO Jeremy and much of the eight person team. For weeks after, I emailed any and all contacts at Yelp in hopes of getting a job. They were like, “Can you code? No? Sorry, we’ve got nothing for you.” But a few months after, they posted for an Office / HR Manager and I jumped on it.

What were your first impressions of Silicon Valley?

The early 2000s stereotypes were true: the scene I was privy to was mostly enginerds in hoodies who wore a rotating collection of startup t-shirts. When I started working at Yelp, we were sharing office space with a few other companies that were birthed from MRL Ventures, the incubator started by Max Levchin (Paypal co-founder). I didn’t know anyone else working at startups in the city. Most people I met in technology were at the old giants—eBay, Salesforce, Cisco—in the South Bay and a handful were at Google and a rising star called Facebook.

Walk me through your experience working in tech.

In 2004 at 22 years old, I started off as an admin at Yelp when the company was nine people. After a year or so, when the company set its sights on expansion, I joined the marketing department. We had a market-by-market strategy which involved a person on the ground leading the efforts. So off I went to Boston to launch our third city.

Essentially it was my job to introduce new people to the product and made sure they continued to participate. Tactically, this combined a heady mix of online engagement, offline events, local PR, content, and partnerships. Internally we were referred to as the “Mayors” of the city as we were always out and about. After Boston was up and running I found and trained a successor and moved onto the next market. After tackling a few cities, four years of a 24/7 lifestyle, and experiencing the company explode to over a thousand employees, I was in desperate need of a break. It was whiplash inducing, but awesome.

During a cross-country road trip with my now husband then boyfriend, I read about a site called Airbnb where you could stay at people’s homes instead of a hotel. I loved the concept. When I returned to SF and read that they were part of YC Combinator I figured they might be a company worth working for and figuratively banged down their door until I got an interview. This was 2010.

I was slightly disappointed to hear they’d recently moved out of the cofounders home as I looked forward to an intimate team again. But working at a place without a shower probably meant better hours. The position they were hiring for was content and as a weekly newsletter was part of our Yelp responsibility, I figured it was something I could tackle. I was also stoked about the introverted nature of the job as I felt socially tapped out. Fourteen interviews later I was offered the position – at a salary I’d been making years prior. Yelp had not yet gone public, so in hindsight this was probably not the wisest decision. But I negotiated a larger equity stake and began clicking away.

At 28, I was one of the oldest people at the company. What the team lacked in experience, they made up for in passion, creativity, and scrappy. Everyone was running a million miles an hour—sometimes in different directions—but there was certainly no lack of motivation. It was intoxicating.

What was it like building communities from the ground up? Did you have free reign to just build and learn as you went?

Marketing starts out a series of experiments of different channels—test and measure, tweak and repeat. As the bulk of my experience has been at early stage startups, there’s little dev and data time to devote to our cause. So initially you’ve gotta run on your assumptions. Nowadays, there’s a plethora of bolt-on products that can track anything under the sun. We weren’t so lucky in my day.

Fortunately at Yelp, Nish at developed a tried-and-true strategy that we were able to adjust to our local markets, so there was little on the strategy level for us to hash out. We had very clear output metrics and were rewarded with recognition accordingly. So I knew what I needed to do to excel.

Airbnb was green field. From the marketing side, they’d dabbled in the basic channels—social, content via blog, and video—as reflected by the team’s talents. But everything was a bit haphazard and as the founders had never managed marketing, we were left mostly to our own devices. Shortly after I joined they brought in a consultant named Julie Supan, formerly VP of Marketing from YouTube, who’d been recommended by investors.

Julie gave us much needed structure and our first tangible goal—to articulate the vision and mission of the company. As the content lead, I spent countless hours with her and cofounders in hopes of distilling the company’s raison d’être, and working in tandem with product, produced the Home and About pages seen by hundreds of millions of people around the globe.

After a few months, Brian and Joe got pumped about doing more community-oriented efforts and switched me to the task. They were excited about bringing people together offline with the hopes of activating host growth in target markets. How to do this, and to some extent where to activate, was up to me. The traveling began.

“I never saw myself paving any path. I’ve always felt more like a pinball ricocheting.”

At first we mostly operated from hunches. I had few tools to work with, aside from pulling the emails of hosts in certain geographies. Everything was tracked manually: the number of attendees, behavior changes post-event, referrals they brought in. We tested different promotions aiming to get a broader, new audience. Though all we could see were the number of properties in each city and the hits to the blog. As they kept increasing at a faster rate, we assumed we were doing something correctly. We optimized the sequence of different types of events: launch parties, host training sessions, and in-home host celebrations, as markets matured.

It wasn’t until my second year in, after I had grown the team to dozens of Community Managers in key cities, that the data dudes had the bandwidth to definitively prove our hypotheses: yes, users who attended events became more successful hosts and repeat travelers with higher lifetime values. It was not for naught.

Where do you think you got the knack for paving your own path in your career?

It’s interesting you phrase it like that. I never saw myself paving any path. I’ve always felt more like a pinball ricocheting. My decisions have seemed like a series of decisions optimizing for local maximums, more like a moth smelling its way than an arrow flying straight and true. But I’ve been fortunate that my compass has always taken me to good places and that’s reinforcing.

I attribute this to two things: only work for companies with a product I’m crazy about and want to use—case in point, I’m typing this from an Airbnb and I haven’t worked at there in years. And comfort with extreme risk. I can’t tell you how many times people have tried to dissuade me for working where I have, “Let a stranger sleep in your bed? That’s nuts.” or “Do they have any money? You’re going to be out of a job in months.” And the number of raises I’ve forgone for equity?! What can I say? I’m a stubborn believer.

What do you look for in a job now vs when you started?

In the past, my sole criterion was all about the product – did I use it, did I love it? Nowadays, it’s not just about product but also about timing. So much changes when a company scales and matures: employee culture, potential impact, compensation, career development and potential, time commitment. In the past I’ve liked the early stages when there’s freedom to be unconventional and potential to lay a strong foundation for growth. But there’s tradeoffs too, lack of stability and work/life balance, lower pay due to low revenue and/or funding, to name a few. I’m finally starting to understand why people I respect have worked at ebay and other corporate giants haha.

Overall, what have been the most exciting things about your work? What about your work really activates you? What are you proudest of?

It has been immensely gratifying to help shape a nascent product into something that tens millions of people interact with regularly. The sheer scale of potential impact of technology is astounding and addicting. I get most excited when hearing the stories of how people have improved their livelihoods, relationships, and decisions using products I’ve worked on: Business owners on Yelp attracting passion clientele that lets them thrive; Hosts at Airbnb being able to send their kids to better school or using the extra income to pursue a new career. It doesn’t have to be in profound ways either. Little incremental increases still count for me.

Everything I’m most proud of has a name: they are the people who comprised my team at Airbnb and are the founders of my portfolio companies now. We are made better by the people who give us reign and feedback, and that goes in both directions. I’ve never been a leader by force; if I had a superpower I think it would be that I recognize drive in others and the (potential) skills they possess, and will fight for the resources to make them successful. I hope my people feel the same way.

What has your experience been like transitioning into investing?

After Yelp and Airbnb went well, people began coming to me for advice about marketing.  I joined a few companies as an advisor—namely Skillshare and Threadflip—and helped craft their growth strategies. It was a great way to see these companies from the inside, providing valuable diligence. I then joined 500 Startup’s mentor network, offering guidance to their portfolio companies. This gave me increased insight into new sectors and teams, as well as keep a pulse on industry trends.

When I didn’t have ample bandwidth to go around, I asked how else I might be of help and was told that investing in these companies would be the next best thing. While of course I understood that this involved a high level of risk, I allowed myself to start investing because I felt like I received more from the startup ecosystem than I deserved and I wanted to give back.

“I read various approaches to portfolio theory, and thought it would be wise to invest in things I knew best – female-friendly consumer tech products.”

A few deals into it, finding that I enjoyed myself and that I was inclined to do more, I thought it would be best to get more educated on the matter. I didn’t know many early operators who were investing at that point. So I signed up for an angel investor crash course with Pipeline Angels. Hungry for deeper info, I flew to New York for another seminar with 37 Angels. Confident around a basic term sheet and having expanded my deal flow to the east cost, things ramped up.

“VCs tend to invest in what they know—problems they can relate to.” Tell me your thoughts on this, and what you’ve observed during your time in the and whether this is true to you as an investor.

It’s much easier to assess the value of a product if it’s solving a problem you can understand. Otherwise, you’re relying on the opinions of other people to determine its merits. Also, if it’s a sector you’re familiar with there’s likely better deal flow from your network. You’ll see Institutional VCs often determine their investment theses based on the experience of the partners.

I read various approaches to portfolio theory, and thought it would be wise to invest in things I knew best – female-friendly consumer tech products. Initially I took the “fund founders not (necessarily) products” adage to heart and invested in a few niche products started by people I believed were smart and competent. But as my capital amounts increased I became more discerning about the track record of the founder and the potential market size. From an ethos standpoint, I would love to invest in clean tech and education, but as these are sectors I know little about there’s an increased risk and decrease in my value-add to founders. The key advantage for me to potentially work as an institutional would be to gain knowledge from partners of these sectors. It may still happen.

“I can’t tell you the number of times founders have told me that community ROI can’t be calculated. Ask any technical person what they think of marketers and they’ll likely say that they’re “creative” or “feeler” types with no methods or data to back up their initiatives. I think this has largely been perpetuated by startups hiring smart but inexperienced people to run marketing because early on they can’t afford seasoned talent. This pattern, in addition to data and dev time being protected fiercely, can make it difficult to track returns. But that’s easily solved by the right tools.”

In general, how has your experience been as a woman in tech?

I know everyone anticipates horror stories and I hate to disappoint, but I don’t feel like my path in tech was made significantly more difficult by being a woman. I think this was partially because I was in a field—marketing—that’s high percentage female. I can’t recall any instances when I felt like the target of sexism. However, there has been the conscious awareness that I mustn’t play into the stereotypes of “bad” female behavior i.e. emotional irrationality and outbursts which factors into my communication style and has influenced my feeling comfortable speaking out in opposition. As I’ve rose in the ranks I’ve also been keenly mindful as to not come off too strongly or alpha for fear of being seen as a bitch or unlikeable.

While I also pride myself on being somewhat stylish, I know my friendliness is often mistaken as flirtatiousness so in the past five years or so I’ve been more conservative in my apparel choices—nothing revealing or body conforming. But the reasons for doing so are not just to discourage male attention, but to remove all question of why I may be getting ahead other than my own merit. I’m sure most men never have to consider this. Truthfully, I suspect I’ve largely been shielded from some of the more overtly inappropriate behavior from men because I’ve been in a serious relationship for most of my career.

What have been your biggest struggles?

I can’t tell you the number of times founders have told me that community ROI can’t be calculated. Ask any technical person what they think of marketers and they’ll likely say that they’re “creative” or “feeler” types with no methods or data to back up their initiatives. I think this has largely been perpetuated by startups hiring smart but inexperienced people to run marketing because early on they can’t afford seasoned talent. This pattern, in addition to data and dev time being protected fiercely, can make it difficult to track returns. But that’s easily solved by the right tools.

Like many marketing and community folks, I’ve had to contend with this much of my career. It’s hard enough trying to grow and engage users without having to constantly prove why you should exist. Oh, I should note that these stereotypes have shifted a bit as performance marketers have rebranded themselves as “growth hackers”. If there are any brand / community folks out there, I’ll cut to the chase: you’ll never get a lower CPA from any channel other than paid, so don’t try; instead focus on increasing LTV.

Angel investing is tricky and largely a failing proposition. You’ve heard about the power law rules of the game, right? Where one of your bets can potentially make up for all the others that have flamed out. Well, that means you’re competing for the hot deals with all the other early stage investors. Now that everyone’s an angel, getting into the deal is the hard part. So your network is everything.

Problem is, people have to know you’re doing a certain thing in order to share that type of info with you. And when I’m learning the ropes, I always shy away from the spotlight. There’s an inherent conflict, which I’ve now mostly overcome. But I’m sure I missed out on a lot in the meantime.

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

I am grateful at Yelp to have had a number of bosses all strong in their own dimensions: Geoff Donaker Yelp COO with his business acumen and analytical bent, Nish Nadaraja for his creativity and engaging pen, Michelle Broderick for her direct but encouraging management style and sharp wit. Much of the time when I was an operator, I was so heads down building that I did little in the way of networking or professional development. It’s a shame in hindsight as I had access to an amazing group of investors and advisors and I regret not taking advantage.

The story has played out differently with angel investing though. For many months I was afraid to tell anyone I had started, afraid of smarter people scrutinizing my picks and judging me accordingly. But after I’d grown more comfortable and started asking people in my network for their thoughts on deals I found that most were more than happy to candidly share. Kanyi Maqubela, Josh Felser, and Niko Bonatsos have all been encouraging and insightful and I am ever grateful.

I’m a huge fan of Cyan Banister. I respect that she struck out on her own as an angel, not waiting for an institutional to invest under, and absolutely kicked ass. So stoked to hear Founders Fund brought her on as partner—couldn’t be more well deserved. From afar, I’m a great admirer of Aileen Lee and have watched or read every panel, interview, or talk she’s ever done. She’s sharp, irreverent, and downright cool. And of course a great picker. It would be a dream to work with her one day.

What are your biggest motivators?

I want my brain to be stretched. I’d like to grow in so many ways: creatively, business-savvy, analytically – and I hope to be able to help people in some way during this process.

Where have you found support networks?

Connecting with people that have shared plights and joys has been illuminating and validating. David Spinks gets full credit for bringing together community people through his organization and event series CMX, and I’ve met so many wonderful people that way. I’ve also gleaned valuable info and support from women in 37 Angels. The group consists of investors of various ages and backgrounds, and I’ve enjoyed their difference in perspectives. The startup scene can be a myopic echo chamber.

What would you like to see change?

The “change the world” mantra of tech is a double edged sword. On one hand, it’s a boon to the industry, attracting people from all corners of the earth to try and create a company for the goodness of humanity, and to leave a meaningful legacy behind. On the other hand, it creates this immense pressure to dream bigger and solve bigger problems. I’ve seen people spiral into incredible existential crises because they don’t (yet) have an idea that will change the world on a massive scale and it makes them really unhappy. We need to allow ourselves to work on things that move us, however seemingly insignificant. Everything starts out small.

There also needs to be more people of color, women, those from developing countries, and people from various socio-economic backgrounds in VC, so that the types of problems that are being funded are speaking to the needs of a broader swath of the world.

“I’ve seen people spiral into incredible existential crises because they don’t (yet) have an idea that will change the world on a massive scale and it makes them really unhappy. We need to allow ourselves to work on things that move us, however seemingly insignificant. Everything starts out small.”

And not to open a whole can of worms, but we need to close the gender pay gap.

So what are you working on right now, either for work or for yourself?

As Kim Hunter from Women Catalysts so nicely summed up, I believe that life is not a ladder, it’s a jungle gym. We don’t have to take a straight path to the top. We can be many things at different times.

Earlier this year I started a tiny tiny microfund that invests in restaurants, something I’ve been doing occasionally over the last few years. Many will laugh as it’s often thought of as a losing proposition. But this isn’t about 100x returns for me; I’ve got reasonable IRR in mind. My motivation stems from conversations with restauranteurs and chefs; I realized they lacked a supportive ecosystem. In an affluent city such as San Francisco with such a food-obsessed populace, this didn’t seem right. I hope to create a stronger bridge between the tech and food communities.

I’ve spent years focused on my career, ignoring the other aspects of life. This phase is about reaching new professional frontiers, but also being intentional about my family life, health, spirituality, and creative side.

How do your friends and family feel about the work you’ve done?

My family doesn’t really have any idea what I’ve done. They just know I have a decent amount of Google search results. As for my friends, I hope they’ve deemed me having accomplished enough to warrant their respect and esteemed company—hah!

What do you think about the state of tech in 2016?

Big question here. I could talk about the funding environment tightening up, how there’s no stone unturned in consumer, yadda yadda yadda. But you’ve heard it all before, I’m sure. So I’ll give you my take: I’m encouraged to see resources pouring into healthcare, clean tech, and education. But the overwhelming feeling is one of immense possibility, mostly inspired by my husband (who’s a programmer). I’m eager to see what the future holds with AI and VR/AR. In the next decade, we’re going to see massive shifts in production and human behavior with these technologies in ways we can’t possibly predict. As cliche as it sounds, I actually do feel blessed to be alive at this time in history.

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

Learn a hard skill. Move to a tech hub. Hunt down companies who hope to make a dent in the world in a way you can get behind. Bang down their door. Work hard for them, for free if you have to. Develop a network of peers and mentors. Stay up on the industry happs. Help people and be kind. You’ll be amazed at what comes back in return.

“Help people and be kind. You’ll be amazed at what comes back in return.”

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’m from a town called Newtown, Pennsylvania, it’s about 45 minutes north of Philadelphia. I grew up there, but went to high school in Princeton New Jersey, which was kind of interesting  because it was a day school, so I would drive back and forth across the river every day from Pennsylvania to New Jersey to go to school. The school I went to for middle and high school was a school called Stuart Country Day School. It was very interesting, it was an all-girls private Catholic school.

I think that was definitely formative, in terms of only being around other girls for most of my significant schooling. So I’m definitely a proponent of single-sex education, at least in the classroom. I think that it suffered a little bit because we didn’t have a social component, like a brother school with high school boys. The prom was kind of weird because it was just  women in dresses, but we still had a great time. But in terms of academics, it was definitely cool to be in advanced physics classes with all girls.

“I hadn’t really considered computer science as a major, mostly because I didn’t really know what computer science was. When someone told me they had a degree in computer science, I thought, ‘Oh, that’s like the Geek Squad.’ I didn’t really understand what that meant, and what you do. As a funny anecdote, I actually remember one of my teachers in high school saying, ‘I really think you’d like this computer science stuff. You could get a great job.’ I was looking through some information trying to figure out what kind of jobs I could get with that degree, and one of the things was a job at Google.  I remember asking her, ‘How could you work at Google? It’s a website; that doesn’t make sense!'”

I can’t even imagine what that’s like.

It was pretty awesome. This whole concept of, “Women can’t do science” and “girls are bad at math,” just wasn’t a thing, because it was like, “Well, someone has to be good at calculus, and we’re all women, so…”

I love that. When did you first get interested in tech? Was it early on, or was it after you were already in it?

I actually got interested in that in college. I hadn’t really considered computer science as a major, mostly because I didn’t really know what computer science was. When someone told me they had a degree in computer science, I thought, “Oh, that’s like the Geek Squad.” I didn’t really understand what that meant, and what you do. As a funny anecdote, I actually remember one of my teachers in high school saying, “I really think you’d like this computer science stuff. You could get a great job.” I was looking through some information trying to figure out what kind of jobs I could get with that degree, and one of the things was a job at Google.  I remember asking her, “How could you work at Google? It’s a website; that doesn’t make sense!” [chuckles].

Little did you know.

Yeah. Surprise! [laughter]

How was your college experience working in computer science? I’m assuming that it was gender mixed at this point.

After high school, I enrolled in the engineering school at the University of Pennsylvania. First of all, it was  a culture shock to go from an environment that was all girls to an environment that was almost entirely male. That was just a strange transition to make. I think college is what made me know for sure that I wanted to be in tech. It’s also probably the time when I wanted to quit tech the most and it would oscillate back and forth everyday.

Tell me more about that.

I struggled a lot with confidence and identity in college because there was this general feeling that there’s a certain type of student in CS and that student is going to grow up and change the world. They’re the next Mark Zuckerberg and the next Bill Gates. That archetype was almost always a white or Asian male student. But even more so than their race or their gender, it was really this attitude that you had to be bored in class. In your 100- and 200-level courses, you had to be like “It’s so easy; I’ve done this so many times; I’m so bored.”  And because they were so “bored” in these very difficult classes, they would go home and spend all their time learning about other technologies because they had the time to do that, apparently.  It turned into a vicious cycle where you would talk to some classmates and they would be like, “Oh, you don’t know Django?” And you’re like, “No. I’m in CS 101. Why would I know—what is that?”  And they’re like, “Oh, well, I’ve been programming since I was 14.” So even though I was learning a lot, I always felt like I was behind my classmates because I had to work hard just to get my schoolwork done.

“I struggled a lot with confidence and identity in college because there was this general feeling that there’s a certain type of student in CS and that student is going to grow up and change the world. They’re the next Mark Zuckerberg and the next Bill Gates.”

You’re not the first person to say that was the vibe. It was competitive—flaunting, some maybe not even being truthful about it.  Everybody competing about how easy this is, when in reality, most people are like, “Am I the only one who’s struggling here?”

Yeah, and that was very different from high school for me. I’m not going to beat around the bush; my high school was very, very competitive. But you could see the toll that the hard work was taking on the students. No student would ever tell you, “Oh, I’m so bored, this is so easy for me.” Students were like, “Yes, this is a lot of hard work and I’m tired as hell”. When I went to college, I really fell for the idea—for a long time—that if you don’t find everything easy then there is something is wrong with you. It felt as though even if you got an A, if you had to work for the A, then you didn’t really belong there.

“When I went to college, I really fell for the idea—for a long time—that if you don’t find everything easy then there is something is wrong with you. It felt as though even if you got an A, if you had to work for the A, then you didn’t really belong there.”

From there, walk me through how you got into your career.

After I graduated, I did an internship at Apple. That was a ton of fun. I learned a lot and it was incredible to actually see one of these big tech companies from the inside. After I finished up at Apple I went back to Penn to finish my Master’s. Looking back, I think the reason I did the Master’s was because I didn’t feel confident in my own skills. I figured instead of graduating with a Bachelor’s and maybe not getting the job I wanted, I would stay for another year and finish up the Master’s. I thought that would put me on par with my undergrad classmates, which was not true, but that’s what I still believed deep down.

So I went back and did my Master’s, and while I was in school I met a guy named Andrew, who eventually became a good friend of mine. When I met him, he was looking for people to work on his app. He was a business and product-minded kind of guy with a lot of hustle, and I decided to work with him and see what came of it. We ended up working together during my last semester on iPhone/iPad apps, and we had a ton of fun. So after I graduated, we decided to just start a company called Nymbly. It was just the two of us, contracting and writing apps. We did that for about a year, and we had this whole plan where we were going to become this tech/media empire where we would do contracting, then subcontracting, and then start coming out with original content. We had a few successful apps, but the overall vision was way too ambitious. After a year I was struggling, and we decided to take a break and quit while we were ahead and still friends—and still healthy [laughter]. We ended up going to a company in New York called Fueled. It was this big flashy agency that was doing apps for both big companies and one-person startups, and they had their own original content. It was exactly like what we had hoped our company would be. We both quit Nymbly, applied to Fueled, and got hired in more or less the same roles. That was super cool, because it felt like an acquisition but without the paperwork [laughter]. I ended up moving up to New York to work for them.

And how did you end up at Google?

Before I accepted the offer at Fueled, I had been in contact with a Google recruiter, but I put my application on hold because I got the Fueled offer soon after that. A few months later, they got back in touch and I decided to just continue the interview process to see if I would have gotten the job. The answer was yes, and I was like, “Are you kidding me? If I had known it was going to be yes, I would have just waited [laughter].”

But it worked out, and I ended up moving over to Google New York. That was probably the greatest day of my life. The first day at Google I got the hat with the pinwheel and everything.

Working at a website? Woohoo!

I should go back and email that high school teacher and just tell her,”I did it. I’m working at a website.” [laughter]

So you’re doing really well at Google.

Yes.. I joined the Google Wallet team for iOS because I really wanted to make sure I kept doing iOS development. I was on the Google Wallet team for about a year, and then there was a restructuring and we ended up moving the Wallet team from New York to San Francisco. I had a choice between staying at Google NYC in a new role, or moving and keeping my current role. I liked what I was doing, so I moved to  San Francisco, and that’s where I am now. I live in Oakland these days.

“I was terrified, but I didn’t want to tell anyone at work that, so I tried to be confident at work and then I would go home and freak out. I was really afraid that I was going to mess it up and that in messing it up not only would I ruin my own career, I would ruin the careers of all the people who came after me that look like me. I was afraid that if I made a major mistake people would say, ‘See, this is why we don’t put black women in charge of stuff because look what happened to Google Wallet,’ and that would be the reference from then on.”

How was that shift for you? I’ve lived in New York and San Francisco and I love them both, but they’re so different.

That was a crazy shift. As an East-Coaster I am confused by California daily, and I just don’t understand what’s wrong with people sometimes. They’re too nice!

I get it.

Yeah. The geographical transition was interesting, but the work transition was even more daunting. In the shuffle of moving everything from New York to California I went from being one of a handful of junior engineers on the team to being the lead engineer. I decided to run with it and it’s been about a year since then.

Was there any apprehension about suddenly taking charge ?

I was terrified, but I didn’t want to tell anyone at work that, so I tried to be confident at work and then I would go home and freak out. I was really afraid that I was going to mess it up and that in messing it up not only would I ruin my own career, I would ruin the careers of all the people who came after me that look like me. I was afraid that if I made a major mistake people would say, “See, this is why we don’t put black women in charge of stuff because look what happened to Google Wallet,” and that would be the reference from then on.

On that note, what has been your struggle either in work, or the culture, or anything?  What has been hard for you and what have been road blocks?

I think that at work my struggle has really been this fear of failure, specifically being afraid that my failure is going to be an issue for not only myself but also for other black women in the future. Sometimes that leads to a little bit of extra frustration. I look around at my coworkers and I know that if a white guy messes something up he’s probably going to be fine, relatively speaking. Sure, he messed up the big meeting, but no one’s going to look at him and think, “Boy, that went poorly, maybe we shouldn’t let white guys run meetings anymore.” That’s just not a thing that people are likely to say. Sometimes I get tired of the fact that there’s this extra pressure on top of already having what I consider to be a pretty difficult job, so that’s definitely a challenge. Some people talk about not fitting in with the stereotypical geek culture of Star Wars, Star Trek, video games, comics, etc. That hasn’t been too much of an issue because I naturally gravitated toward that stuff anyway. I think the number one issue I have is really just the confidence and the identity thing. It goes back to those same issues from college of feeling like I’m the only person that’s struggling with something, or I’m the only person that hasn’t read this book, or learned this specific part of computer science. That feeling is so dangerous because it makes you think that whatever it is that you didn’t do, you’re the only person that didn’t do it. “That thing that you’re not doing? Everyone else is doing it and that’s why they’re going to be the next Steve Jobs and you’re not.” And even though I know that’s not true, it’s very, very hard to break that cycle and stop listening to that narrative whenever you hear it. I think that it is really isolating when all of us feel pressure to just make it all look so easy and refuse to share that sometimes things are really difficult for us. I think it affects your work relationships, too. There are times when I’m reluctant to go to someone for help because I don’t want them to know that I’m struggling, or I don’t want them to know that I didn’t quite understand something. Sometimes, rather than asking someone and getting a five-minute explanation, I’ll go home and read documents for an hour to try and figure it out because I don’t want everyone to know that I had trouble. I know it sounds crazy, but I still find myself doing it sometimes, and I see lots of other people doing it, too.

“I think that at work my struggle has really been this fear of failure, specifically being afraid that my failure is going to be an issue for not only myself but also for other black women in the future. Sometimes that leads to a little bit of extra frustration. I look around at my coworkers and I know that if a white guy messes something up he’s probably going to be fine, relatively speaking. Sure, he messed up the big meeting, but no one’s going to look at him and think, ‘Boy, that went poorly, maybe we shouldn’t let white guys run meetings anymore.'”

I can totally relate. During my time in tech, I remember just putting in hours and hours and hours of secret work, to make sure that I was twice as good without having to ask for help. 

In your pre-interview, you mentioned being a double minority in tech,  and I’m curious to know if you experience the two separately, in different ways? Does that make sense?

Well, it’s very hard. A lot of times, when there is an incident, it’s so subtle that you can’t tell what the other person was reacting to, race, gender, or both. I think the time that I’ve felt one minority status more so than the other is actually when I would go to the computer science club for women in school, or the female employee group at work. I actually feel a lot of otherness in those situations because even though on the surface, the group is dedicated to women and our unified experiences, they often cut out the experiences of women of color. It’s  like the lowest common denominator; the women’s groups only talk about experiences that all women face, not experiences that some women in the group may face. It ends up being mostly about the experiences of white women, rather than any and all women.

“I think that it is really isolating when all of us feel pressure to just make it all look so easy and refuse to share that sometimes things are really difficult for us. I think it affects your work relationships, too. There are times when I’m reluctant to go to someone for help because I don’t want them to know that I’m struggling, or I don’t want them to know that I didn’t quite understand something. Sometimes, rather than asking someone and getting a five-minute explanation, I’ll go home and read documents for an hour to try and figure it out because I don’t want everyone to know that I had trouble. I know it sounds crazy, but I still find myself doing it sometimes, and I see lots of other people doing it, too.”

That’s really interesting. I am learning so much from this project. It’s really amazing. Have you had mentors or people that you’ve looked up for inspiration along the way or have you just been creating your own path?

Yeah, I definitely have. My parents are definitely examples for me. Both of them grew up in low-income areas and went on to graduate-school and were very successful. Within the office, I was very fortunate to be placed in a group where the director was black. He was also one of the advisors of the Black Googler Network, so it was really cool to be able to talk to him, because he was someone who was higher up in engineering. He had experienced a ton of things within Google as an engineering director. But he also understood the product that I work on, so I didn’t have to talk in vague terms. I could actually talk to him about the work I was doing on a daily basis, and that was really great.

Similar, but different, what are your biggest motivators? What drives you?

It’s different every day. I think overall what drives me is really just wanting to see what I can do. I think something that’s unique to this generation is that when we were kids, we were told, “You’re so smart. You’re so talented. You’re going to do amazing things. You’re going to change the world.” So now that I’m older, it feels like it’s time to put my money where my mouth is. A lot of people are motivated by a single cause, and I just want to find something and run with it until I can’t do it anymore, then switch and do something else until I can’t do that anymore, and see where I land.

Back to your parents, how do your friends and family from home feel about the work that you’ve done and how far you’ve come?

I think they’re definitely proud. It’s funny because neither of my parents have technical backgrounds – they’re both in law – and sometimes I’ll try to explain why something was good or bad and they’re like, “That’s nice. Just keep up the computer stuff.” I’m like, “Alright thanks, I will.” [chuckle] But knowing people are rooting for me means the world to me.

“I think the time that I’ve felt one minority status more so than the other is actually when I would go to the computer science club for women in school, or the female employee group at work. I actually feel a lot of otherness in those situations because even though on the surface, the group is dedicated to women and our unified experiences, they often cut out the experiences of women of color. It’s  like the lowest common denominator; the women’s groups only talk about experiences that all women face, not experiences that some women in the group may face. It ends up being mostly about the experiences of white women, rather than any and all women.”

You’re far from home, so where do you find your support networks here?

It’s difficult, to be honest. I’ve actually started going to more meetups and events for women in tech, or people of color in tech, or women of color in tech, or any combination of that. Those have actually been really cool just to start building a friend network and things like that. It is tough, though. Most of my friends and family are on the East Coast. I also think it helps a ton that my boyfriend moved out here with me from New York, and we live together. It’s been really great to have him since he’s the one person who understands everything I’ve been through recently. He’s also in tech, so he understands the work I do, in addition to things like the cross-country move. He is  the one person that’s been here for the whole thing [chuckles].

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

I think those are actually the same thing. I think what frustrates me—I’ll start with that—is this proliferation of useless tech. People are just pouring money into it, and it’s like, “Oh wow, an app that’s like Tinder for cats.” I’m not going to use that. Yet, they manage to raise like $10 million—that makes no sense. It’s ridiculous. Especially in San Francisco, everywhere you go, there’s a person who’s trying to push a stupid startup on you. But I think that there’s more people who are finally coming to that realization, and there’s a second undercurrent of people who are intentionally shunning those things and turning toward what I think are better causes. I’ve seen education becoming a bigger thing. There are startups trying to fix what’s wrong with the government or the environment, and more focus on diversity and inclusion. It seem like people are turning toward more serious causes than just seeing what kind of app you can make, how fast, and how much money someone will give you for it.

So I’m hopeful about that.

What do you love most about working in tech and the environment you’ve ended up in?

I think I’m a person that even if I wasn’t in tech, I would be a techie-type person. I would be all about my phone and all about my computer, so it’s cool that, given that that’s something that I think I naturally gravitate toward as a hobby, I get to see the cutting edge of that. And to understand how the products you use work is really empowering as a consumer. And then in terms of being at Google, I think it’s really cool that there’s so many people who are so incredibly brilliant and talented, that you could walk down the hallway and run into someone who wrote the book that you were just reading before you got up. It’s great to be in an environment where there’s that many smart people all working toward a common goal.

What do you think your background and life experiences impacts the way that you do your work and bring something to a team?

I think that the number one thing that I bring to the team is making sure to always acknowledge other perspectives. For example, the product I work on is a personal finance app. Growing up I came from a very economically privileged background. I was a prep school kid.  Even though I’m privileged enough that I don’t experience some of the things that a lot of our users experience, I think being “on the outside” in other ways has ingrained it in me to always at least ask what someone else would think about the product we’ve made, and not to assume my experience is the default. I think that sometimes people get worried about being privileged and they ask, “How could I have every perspective? I haven’t experienced what it’s like to be everyone, that’s ridiculous!” The result is that they view designing products for everyone as an impossible task, and don’t even try. You don’t need to have every perspective yourself. You just need to be able to know that someone else might think about things a different way, or they might use the product in a different way. To be willing to go out and ask those questions and figure out what that different way of thinking is, I think it’s pretty valuable.

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

For work, still Wallet, though I’m excited to say I’ll be transferring to the Android Wear team soon. Personally, however,the thing I’m really excited about—which has nothing to do with tech—is adult literacy, teaching with the Second Start program through the Oakland public library. I just signed up and completed the training, and soon I’ll be assigned a student. I’m going to start meeting with them in the next couple of weeks. I’m so excited to be able to teach someone to read.

Do you feel that compulsion the longer that you’re here, to start giving back to the city and getting more involved in things like that?

Yeah, I’m definitely feeling very connected to the community in Oakland. And I think there was also a realization that everything that I have is because of the fact that I read something. I read some book that sparked an interest in something that led to an interest in something else, which made me pick up another book and read something else. And the whole chain of everything I know and care about is built from things that I’ve read. I don’t even know how much of my waking time I spend reading. It’s probably about 75 percent. I’m always looking at something. Imagining what that’s like to not be able to read and to be so cut off from that experience. It breaks my heart, so I want to try and do something about it.

“Even though I’m privileged enough that I don’t experience some of the things that a lot of our users experience, I think being ‘on the outside’ in other ways has ingrained it in me to always at least ask what someone else would think about the product we’ve made, and not to assume my experience is the default. I think that sometimes people get worried about being privileged and they ask, ‘How could I have every perspective? I haven’t experienced what it’s like to be everyone, that’s ridiculous!’ The result is that they view designing products for everyone as an impossible task, and don’t even try. You don’t need to have every perspective yourself. You just need to be able to know that someone else might think about things a different way, or they might use the product in a different way. To be willing to go out and ask those questions and figure out what that different way of thinking is, I think it’s pretty valuable.”

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

Yeah, I think I’ll still be in tech. Like I said earlier, I want to go as far as I can with something until I can’t anymore, and then just figure out where I can go from there. I think that I still have a lot to learn in tech. I’ve mostly been doing mobile development. I haven’t tried my hand at hardware or server-side development, or even front-end web development. I still have a lot that I could learn within tech.

Lastly, what kind of lessons have you learned or what advice would you give to folks starting out in tech, or hoping to get into tech?

The number one piece of advice would be: tech is not easy and don’t get discouraged, or think you’re not cut out for it if something is difficult. If it seems like everyone else around you is having an easy time of it, trust me, they’re not. It sound  cliche, to say “believe in yourself.” But really, do it.

“Tech is not easy and don’t get discouraged, or think you’re not cut out for it if something is difficult. If it seems like everyone else around you is having an easy time of it, trust me, they’re not.”

I grew up in the Midwest first in Pennsylvania until I was 9 – and then Ohio, and I started programming in high school. During Sophomore year I decided to be lazy and take an extra study hall, but the computer science teacher, Mrs. Petite, hunted me down, along with all the other advanced math students, and said “You should take my class,” and I’m so glad she did.  I took two and a half years of computer science in high school and just absolutely loved it. My first class was in Visual Basic, and I made the video game Frogger as my final project.

At the end of my sophomore year I was very nervous, I knew that my school had AP computer science courses but I wasn’t sure if I would be good at it.  I asked my teacher Mrs. Petite who said, “Of course you would be. Sign up.” So I did. I took AP computer science A junior year in C++ and AP computer science B senior year in Java.  I fell in love with programming in high school, I loved how quickly I could bring my ideas to life, and so I went into college knowing I wanted to major in computer science.

“I fell in love with programming in high school, I loved how quickly I could bring my ideas to life, and so I went into college knowing I wanted to major in computer science.”

How was college for you?

College was great! I always knew from a young age that I wanted to do engineering or math or science based things. I just liked them in addition to a healthy appreciation of the art.  I spent a lot of time writing, reading literature and dabbling painting and pottery. But I had a penchant for the sciences, so when I applied to colleges I focused on schools with computer science departments.

I eventually chose Cornell University in Ithaca, New York which has a really excellent computer science program.  It is a super tough program but it was really fun. I have some best friends from that program that I still very close with even though we live in different cities.

In college I also TA’d a class that was the Intro to Data Structures course in Java.  I also became interested in game design and built a couple video games, via an elective program.  I was also incredibly interested in computer graphics because I liked the idea that I could visualize or see what I was making and create art. I also came to realize that I was really bad at linear algebra, or not really bad but I was never going to be great at it, so then I thought maybe I should pick a different area to focus on.  

During college I interned at bunch at different places including Stanford’s Linear Accelerator Center (SLAC) and Microsoft.

At SLAC I had my first introduction to large scale computing.  They had, at the time, one of the larger academic computing clusters that the scientists working at the accelerator could use to analyze and compute all the data they were collecting.  In order to do this they needed massive compute, and I worked on the team there that provided it.

I also did a more traditional internship after my junior year at Microsoft, in Seattle.  I worked on Windows Live Experiences which was how I got involved with networking and found a passion for building things that socially connect people.  

When choosing a full time job after college I really wanted to work in Video Games.  I wasn’t exactly sure what area of computer science I wanted to focus in so I figured I might as well just build something that I think is fun.  I ended up landing at Microsoft in Microsoft Studios because I got an offer to work on the Gears of War Series, an Xbox Game.    

“When choosing a full time job after college I really wanted to work in Video Games.  I wasn’t exactly sure what area of computer science I wanted to focus in so I figured I might as well just build something that I think is fun.”

So let’s dig into those first experiences. How was working Seattle? How was working in games?

I loved working in games. I’m really glad I did it in my early 20s. I’m also really glad I’m done, or am on a break from the industry at least for awhile, because it is pretty exhausting. The crazy hours you hear about are 100% true, but I learned so much in those first six/seven years I spent in games because you just work all the time. I loved it and I was having a blast so I don’t regret any of it, just sometimes your priorities change away from just work as you get older.

“I loved working in games. I’m really glad I did it in my early 20s. I’m also really glad I’m done, or am on a break from the industry at least for awhile, because it is pretty exhausting.”

So I worked on Gears of War 2 which was a phenomenal opportunity straight out of college that doesn’t happen in the games industry that often. So I got very lucky and I worked my ass off. We were working 60+ hours a week as soon as I started, and I remember sleeping on the floor to finish builds and taking naps as things were compiling. Game builds actually take a really long time because you have to compile the assets down and then package it into something the Xbox knows how to run. There’s this xkcd comic of, “Oh, it’s compiling” and that’s a real joke in the game industry.

I then continued to work in the Gears of War franchise on Gears of War 3.  As we were working on that—an internal studio instead of Microsoft—343 Industries was created to take over the Halo franchise from Bungie, the studio that created Halo.

“We were working 60+ hours a week as soon as I started, and I remember sleeping on the floor to finish builds and taking naps as things were compiling.”

In 2009, I was loaned out to 343 to work on one of the first title applications on the Xbox360, Halo Waypoint.  Originally on the Xbox360, you had this standard dashboard and all you could really do on the console was play games, I don’t know if people remember that, this was a while ago. And then they added the applications like Netflix, Hulu, Youtube, etc…. Halo Waypoint was also one of the first of what we call title applications, that came out.  It was very new, and I jumped on it because I thought that was really exciting.

At the end of the Halo Waypoint project, I learned that 343 Industries had positions open, so I moved over to that studio full time when it was about 40 or 50 people. I was Web Service Developer number 2 that they hired, so that was pretty cool because we got to take over this whole charter of the Halo universe. I was really young, only 23, so this was an amazing opportunity, so I just ran with it.

Halo was really fun, it was this crazy wonderful experience. It was very career-defining for me. It’s definitely the biggest thing I’ve done at this point. We re-wrote all of the Halo services in Azure, which is Microsoft’s cloud compute. We also built a lot of it on top of this Microsoft Research technology called Orleans. The Orleans team was amazing we approached them and said, “Hey, we like your stuff. We would like to build all of the Halo services. Will you work with us?” and they were crazy enough to say, “Yes.”  Then we were crazy enough to think we could do this so we did it and it was amazing. It really led me to love, not only games and creating the social aspects of it, but also introduced me to Distributed Systems.  

What was it like to be a woman in the Game Industry?

There’s obviously a lot of controversy going on about the games industry now. Everyone knows about all the harassment, especially a lot of women are facing in that industry, especially online, and all the horror stories that are coming out. I actually had a very positive experience, at least with my studio. I attribute a lot of that to the fact that Bonnie Ross is the studio General Manager, and she runs all of Halo at Microsoft. And then the executive producer of Halo 4 was Kiki Wolfkill, another really fantastic woman. And so, when I joined the studio, I was literally joining a studio run by women, and it was fantastic. I think it just set the tone. Even on little things like t-shirt orders always included female-sizes even when we were only ordering like 30 shirts, things like that. The studio always felt very inclusive.

Trade shows were a little different. People would come up to me and say, “Oh, you’re not in marketing?” And I’m like, “No dude, I make the game.” And that was always surprising to people.  I used to count the number of times a person said “Really?” I got up to five once.

“I actually had a very positive experience, at least with my studio. I attribute a lot of that to the fact that Bonnie Ross is the studio General Manager, and she runs all of Halo at Microsoft. And then the executive producer of Halo 4 was Kiki Wolfkill, another really fantastic woman. And so, when I joined the studio, I was literally joining a studio run by women, and it was fantastic. I think it just set the tone. Even on little things like t-shirt orders always included female-sizes even when we were only ordering like 30 shirts, things like that. The studio always felt very inclusive. Trade shows were a little different. People would come up to me and say, ‘Oh, you’re not in marketing?’ And I’m like, ‘No dude, I make the game.'”

So you left 343 Industries? What was the impetus?

Some of it was just—I’d been at Microsoft for five, six years, something like that. Problems start looking more of the same and there was just some things I wanted to go explore outside in other parts of the industry. I was also very burnt out. To be perfectly honest, I was working really long hours even after we shipped Halo 4.

Shipping Halo 4 was one of the most magical, sleep-deprived, wonderful experiences of my life.  I loved every minute of it and leaving Halo in 2015 was really hard, but sometimes you get to a point where you want to do or explore other things.

I then did a year at HBO, which started up a studio in Seattle.  Essentially I was working on what became HBO Now.  I stayed there for only a year.  It wasn’t the best culture fit for me.  

So then I made the decision to move to San Francisco.  I knew a lot of people in San Francisco. I was super excited by the tech scene, just because a lot of stuff is happening and it’s interesting. So I started looking around and interviewed with literally everyone [chuckles]. I had a bunch of job offers from some really amazing places but ended up deciding on taking a job at Twitter, and so that’s where I am now.

What excites you in your work now? Is there a thread across all your work, from games to Twitter?  

I really love Distributed Systems.  The space is developing really quickly as applications have to scale to handle larger amounts of data that’s globally distributed.  In addition we now expect services to be always on.  Down time isn’t acceptable.  So there are a lot of really hard problems in this space, and a lot of overlap between research and industry that really excites me.

I also love Twitter as a platform.  Just like games, I’m helping to build social connected experiences that bring people together. I’ve learned a lot on Twitter, and made some really close friends who I first connected with via Twitter.  I also think Twitter does a lot of good in the world, giving people a voice.

“I really love Distributed Systems.  The space is developing really quickly as applications have to scale to handle larger amounts of data that’s globally distributed.  In addition we now expect services to be always on.  Down time isn’t acceptable.  So there are a lot of really hard problems in this space, and a lot of overlap between research and industry that really excites me.”

How did you get into speaking and writing?  How has that experience been for you?

So I kind of got pushed into speaking actually.  I’ve been very fortunate in my career to have a bunch of people who have sponsored me.  So at Microsoft, Clemens Vasters and Scott Hanselman sought me out and encouraged me to come talk on their podcasts.  I also have a friend Kate Matusdaria who made the intro that led to my first conference talk at Surge 2014.  

I also got invited to speak at Ordev 2014 basically because I got into a heated argument on Twitter with Kelly Sommers and some folks from the Node.js community about Orleans.  Afterwards one of the conference organizers reached out to me saying, “We are really interested in learning more about Orleans and saw the conversation on Twitter, would you like to come talk about it.”  So I responded “I guess, sure. That sounds great.”

My first conference talks went over very well, from those came more talk invitations and most recently an article on The Verification of a Distributed System that was published in the Communications of the ACM.  

What’s it been like being a senior-level woman in Tech in Silicon Valley?

It’s definitely hard, and it gets harder as you get more senior I think.  But I’m in tech because all the toys I want to play with are here, and I love the work I do, so I’m here for the long haul.  

Most days it is fine but every now and then there are things that grate on you.  There’s a lot of little things, like getting offered “uni-sex” aka men’s sized shirts.  Or people being surprised when you say I’m a Tech Lead.  Then there are some people who want to see your credentials.  At this point I’m just like, “Do you need a moment to Google me, hold on I’ll wait.”  Honestly the reason I’ve been hustling so hard the past few years, all the talks and articles outside of my day to day job, helps with my visibility/credibility in the industry.  It makes it easier to show up, because some people already know your name.  

“Most days it is fine but every now and then there are things that grate on you.  There’s a lot of little things, like getting offered ‘uni-sex’ aka men’s sized shirts.  Or people being surprised when you say I’m a Tech Lead.  Then there are some people who want to see your credentials.  At this point I’m just like, ‘Do you need a moment to Google me, hold on I’ll wait.'”

Where have you traditionally found your support networks, and where do you find them now?

My family has always been a huge support.  In the tech community I’ve met a lot of friends via IRC and Twitter, I know that sounds super nerdy.  One of my best friends, Ines Sombra, I knew because of Twitter and we met for coffee when I was in the process of moving down to San Francisco.  There is also a group of people I know from IRC channels, where we talked about distributed systems, and since have become friends.  I’m really grateful for all of them because I have a really strong network of women and men who are very supportive, who get it, who have my back, and I think that is really important for staying in the tech industry.  I do not know how I would do it otherwise.  

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

My mother has always had a career, a very strong one, she’s currently a Director at the US Department of Transportation right now, and has been CFO at companies.  She’s always been managing teams and directors of them, and implementing these big projects. You know, just seeing her out there doing that makes me believe I can.  So her career definitely influenced me early on to also want that for myself.   

Have you had other specific role-models in your life? People that have inspired you?

I feel like I owe quite a bit to my high school Computer Science teacher, Caroline Petite.  If she hadn’t encouraged me to take her class, I probably wouldn’t be where I am today.  Her passion for programming and teaching really inspired me.  I still stay in touch with her via Twitter it’s great, she’s fantastic.

Of course Barbara Liskov, one of the greats of distributed systems, and one of only two women to win the Turing Award.  Also Nancy Lynch, she wrote one of the canocical distributed algorithms books, and has done foundational research in the space.  Just seeing them out there excelling in the space is inspiring to me.  I hope I get to meet them one day.

“I owe quite a bit to my high school Computer Science teacher, Caroline Petite.  If she hadn’t encouraged me to take her class, I probably wouldn’t be where I am today.”

Then there are the women I know more personally who inspire me; Camille Fournier, Ines Sombra, Jessie Frazelle, Charity Majors, Jill Wetzler, Elaine Greenberg, all these women in tech inspire in different ways, and I’m lucky to count them as friends.  

What really excites you about tech right now?

So I get really excited about academia and industry partnerships.  I think we are in a very fortunate time where these key partnerships are starting to happen, because I think we’ve hit the sweet spot where the industry actually faces some of the problems that academia is trying to solve in distributed systems.  In the 70s and 80s when some of the canonical distributed systems papers were written people were still running things on one machine, so it wasn’t as applicable to industry at that point.

I have been fortunate in my career to work with some wonderful researchers like The Orleans Team at Microsoft Research.  I also am lucky to get to chat with academics like Peter Bailis and Peter Alvaro and pick their brains, and hopefully partner with them sometime in the future.

“So I get really excited about academia and industry partnerships.  I think we are in a very fortunate time where these key partnerships are starting to happen, because I think we’ve hit the sweet spot where the industry actually faces some of the problems that academia is trying to solve in distributed systems.”

What would you like to see change in Silicon Valley?

I think Hero Culture is really harmful.  The idea of this one awesome developer who jumps in and saves the day, or founded the entire company, or wrote an open source library all on their own.  I get that it’s a good story, but I’m always skeptical when I hear them, because I’m like did they really or is this just the myth we are telling?

I also think Hero Culture can be really toxic to teams.  It doesn’t foster a collaborative environment.  It’s not helping other engineers on your team grow, especially the junior engineers.  It also creates single points of failures and bottle-necks in your organizations.

But hey, it’s a good narrative.  Who doesn’t like a good story where the hero comes in and saves the day. It’s a much easier story to package and sell versus the team of complicated individuals that had to band together to do something.  

“I think Hero Culture is really harmful.  The idea of this one awesome developer who jumps in and saves the day, or founded the entire company, or wrote an open source library all on their own.  I get that it’s a good story, but I’m always skeptical when I hear them, because I’m like did they really or is this just the myth we are telling?”

Where do you see yourself in five or ten years? You’ve mentioned you’ll stay in tech, but what do you think you’ll be up to?

I’m really indecisive right now about what I want to do next.  Part of me wants to go and travel and work for a while.  In tech we are really lucky that you can find a job that will let you do this and work from wherever you want, and I think that would be an amazing experience.

Long term, I would like to work on more teams where industry and academia are working together.  I think I’m particularly strong in that area, I learn very quickly and understand how much tech we need to solve a business problem.  I hope to keep doing hardcore distributed systems.  I find this area really fascinating, and I don’t think it is going to run out of problems to solve any time soon.  

Honestly the answer to this question changes constantly.  I guess I just hope I’m always learning and expanding my knowledge. I want to keep sharing what I know, having fun doing it, and feel like I’m working on worthwhile projects that make some positive impact on society whether it’s entertaining people or helping facilitate communication.  

Lastly, what advice would you have for women in tech who are hoping to follow in the same kind of path?

You just have to be stubborn right now.  You have to realize that it’s not really fair, and it’s going to be hard.  I know you aren’t supposed to say that but it’s the reality of the situation.  If you consistently show up, do good work, and find a supportive group of people, you can do well.  It may take switching jobs a couple of times, and that’s ok, you don’t owe anyone anything, find a place that’s right for you.

There’s this great interview with Mindy Kaling where she talks about confidence.  She says “Confidence is just entitlement,” and that you earn it by you showing up, working hard, and earning your entitlement.  

Taylor Swift also summed this up well in her acceptance speech at the 2016 Grammys saying, “but if you just focus on the work and you don’t let those people sidetrack you, someday when you get where you’re going, you’ll look around and you’ll know it was you and the people who love you who put you there and that will be the greatest feeling in the world.”

So I think that’s the advice, you just have to show up, do really good work, find the people who love and support you, recognize it is probably not fair, and be a little stubborn.  

“You just have to be stubborn right now.  You have to realize that it’s not really fair, and it’s going to be hard.  I know you aren’t supposed to say that but it’s the reality of the situation.  If you consistently show up, do good work, and find a supportive group of people, you can do well.  It may take switching jobs a couple of times, and that’s ok, you don’t owe anyone anything, find a place that’s right for you.”

I was born in New York. My mom and dad lived in a bad neighborhood and then I think my dad caught someone pulling a TV, their TV out of their apartment at one point, and then they decided to move to the suburbs.

The suburbs are what? Only 30 miles away from where they were in New York, but it’s a world apart. It’s really the kind of place where someone like me can grow up, and just not quite fit in. I think that was really important to my development, because it got me really used to thinking for myself. That’s been really the most satisfying thirty-something-year arc in my life going from public schools in New Jersey, all the way to corporate publishing jobs to doing my own things that are weird and special in their own way and loved for that. That’s been a really big trend in my life, just that feeling of not quite agreeing with the crowd. I started understanding that in New Jersey.

“That’s been a really big trend in my life, just that feeling of not quite agreeing with the crowd.”

What was it like? You are first-generation American on both sides, right?

I think I’m one-and-a-half. My mom has a really thick Queens accent. She went to fashion school in New York she designed jeans in the ’80s for Jordache. My dad is from Hong Kong and was a computer engineer for Hewlett Packard in the ’80s.

What did your parents expect of you growing up? What did they think you were going to do?

My parents really didn’t expect anything, and that was maddening at times. When you’re a kid, you get put into music lessons. I was like, “I don’t want to do this,” and they’re like, “Okay.” That’s not a normal reaction for stereotypical Chinese parents. They were letting us do whatever we wanted to. It’s reflected in the professions of all my brothers. One of my brothers is a musician. Another brother is a furniture maker. That has led to us having not a ton of guidance or structure.

My dad had a really overbearing dad and overbearing older brother, so he never wanted to tell us what to do, as a matter of principle. My mom was just really into being a free spirit. She let us do our own thing. To be honest, when I was younger, that really came off as not giving us enough support, direction. I don’t think people become really, really excellent without some sort of pressure, and that was kind of the pressure that I was given. It wasn’t ever pressure to get good grades. It wasn’t pressure to be a doctor. It wasn’t pressure to do anything and except be myself and do what I wanted to do. It’s a lot of responsibility to listen to what yourself and find out what’s right for you, without anyone programming you for that.

“It’s a lot of responsibility to listen to what yourself and find out what’s right for you, without anyone programming you for that.”

You mentioned that going to school in New Jersey was weird. Tell me more.

I think it was like subtly racist in a way that it just is. In a way that’s not explicit, and I think there’s a weird social dynamic there. That’s part of why I moved to Hawaii. It’s like I don’t need to be a minority anymore. And I really carry that confidence with me that I get from living in a place where I’m not a minority, all the time. New Jersey was just kind of very racist, very classist. It was just like not where I belonged. I’m into deep urban-ness, or I’m into nature, but I’m not into this gray mushy zone in between, that’s kind of what the suburbs were for me.

What were your inclinations as a kid? Did they skew technological? Did they skew towards writing?

My father was an engineer, and we didn’t play sports. We would build remote-controlled cars, and I built my first by myself at 7, and the 16-year-old guy across the street couldn’t figure out how to build his, so I knew I was kind of a nerd by that time. We played around computers, and went shopping for gadgets in Hong Kong during my summers. I just had an aptitude for writing and reading when I was younger. I think, I’m actually at the same reading a comprehension level, now that I did when I was seven. Can you imagine not being any better reading when you’re 39 than when you were seven years old? It’s like bizarre.

Tiny genius Brian.

I don’t know if genius is the thing. It’s like, “why haven’t you got any smarter since you were seven?”

I like the bird sounds that are happening on that side of the audio.

That’s funny that you can hear that. There’s parrots here. I think they filmed some Elvis movie that had green parrots, and then they released them at the end of the filming and then they started breeding. It’s this weird invasive, beautiful parrot species that lives in my neighborhood.

Walk me through the windy path that got you into tech, and your editorial career in tech.

I don’t even know—I don’t consider myself in tech. I went to college in Boston and I switched majors about six times, and I took summer school every summer to catch up, but I never did, and ended up with—you needed 100 credits to graduate and I had 150 by the time I was done. I went from Philosophy to English to Journalism to Photojournalism to Computer Science to Business with an IT slant on it. I was pretty good at photojournalism and really fast in the dark room. Then one day this journalist comes in from the Boston Globe and this was like 1999, so it was beginning of a pretty dark age for newspapers. They could see the internet coming. This one veteran was like, “80% of you won’t get jobs and 20% of you who will will work 80 hours a week for $20,000 a year. It’s going to be bad.” And the same week this artist woman that I was madly in love with said, “Well, I want to be an artist, so I’m probably going to have to marry someone who’s financially responsible.” And I was like, “Alright, maybe I should go to business school.” So I transferred because I was a pretty reckless, idiotic, romantic young person.

I didn’t like it at all in business school. I didn’t fit in. I didn’t have nice clothes. And I didn’t do great. But then it was like 2000, and I got a job at this small web-development firm, and within two months of getting that job I got laid off from the bubble bursting. There were no jobs. So in San Francisco I remember, like, seven people who were let go were crying and then I was just like, “Thanks for the job, it was really nice meeting you.” I just kind of knew that I wasn’t supposed to be doing that kind of work. Plus a couple times I got in trouble for reading about gadgets online, I don’t know why, but it was just interesting foreshadowing.

“I didn’t like it at all in business school. I didn’t fit in. I didn’t have nice clothes. And I didn’t do great.”

I went to work at my boxing gym at the time that I’d just joined. I’d always had a really strong affinity for martial arts. I joined this gym, and I went from answering phones and signing people up and sweeping the floors to eventually teaching. That took like 3 or 4 years and I think I learned a lot in that gym about hustle and working hard. I was so happy, just sweeping the floors and exercising like 5 hours a day, 6 days a week and getting into really good shape, making like 5 or 6 dollars and hour. My life was really simple. At one point, I started to just notice like, philosophically, I was not that aligned with this concept of fighting all the time.

I remember fighting with this woman who became a professional later, she punched me in the nose, and then she was like, “Do you want a tampon?,” it was like the constant joke, my nose used to bleed all the time. So, I just started to realize people in the gym were kind of crazy in a way that I didn’t necessarily want to be. Also, fighters don’t age well, they get beaten-up, and you get brain damage, and they start slurring their speech and it’s just really rough. I saw the writing on the wall, but at some point it really came together when the owner of the gym was hurt as badly as can be.

“I went to work at my boxing gym at the time that I’d just joined. I’d always had a really strong affinity for martial arts. I joined this gym, and I went from answering phones and signing people up and sweeping the floors to eventually teaching. That took like 3 or 4 years and I think I learned a lot in that gym about hustle and working hard. I was so happy, just sweeping the floors and exercising like 5 hours a day, 6 days a week and getting into really good shape, making like 5 or 6 dollars and hour. My life was really simple.”

We would practice in a warehouse space and it had a garage door so we could get airflow. The professionals, who trained in the afternoon, were practicing when all a sudden we hear this crash. Out in front, some guy in this like Jeep Cherokee—he looked like a total techie yuppie, some redheaded nerdy dude—had taken his green Jeep and backed it into a car that happened to belong to the owner of the gym, Alex Gong. He was a professional fighter. I think his fight name was F-14, as in the jet.

The techie put his car in drive and took off down Clementina Street into 5th. Alex being Alex, super combative, professional fighter, super aggressive dude, chases after him wearing boxing shorts and no shirt. I think he took off his boxing gloves, I don’t know. Chases him down. The guy gets stuck in traffic on 5th by the highway entrance. I chase after him with a camera because I’m like, “Well, I’m starting to be a journalist. Let me take a photo of the license plate.” So I run a block, I catch up and I see Alex reaching into the car and getting the guy to try to pull over by taking his keys out. The light turns green, and I hear, “Pop,” and I see Alex fall down. Alex was shot in the chest by this totally yuppie looking guy. The guy took off. Some witnesses got the license plate. A cop showed up immediately, but Alex was dead on the ground.

I don’t remember what I did. Somehow I told the people at the gym that Alex had gotten shot. I don’t know if I had a cellphone back then. Alex was lying in the middle of the street, wearing boxing shorts and I was the only one there who knew him. The cop said, “You should give him CPR.” I’m like “He’s got blood and vomit all over his mouth.” He’s like “use your t-shirt as a mask” So I used my t-shirt and I gave him CPR but in my head, I’m like, “He’s so dead, there’s not even any blood coming out of his wound on his chest.” I just knew he was dead. There was no reviving him. He was shot around the chest, around the heart.

For me, the entire situation can be summed up as live by the sword, die by the sword. So we grieved, and nobody really took the lesson the way that I did. And my lesson was you have to find a way that’s not as conflict-oriented in life.

From then I just really started putting energy into my work life. I took the tools from the gym, the work ethic, the hustle, the pacing, the style, the strategy and I put it towards work. I would just work so hard and I got whatever job I wanted eventually, even if I had to apply a few times. That’s how I got in the door at Wired Magazine.

“From then I just really started putting energy into my work life. I took the tools from the gym, the work ethic, the hustle, the pacing, the style, the strategy and I put it towards work. I would just work so hard and I got whatever job I wanted eventually, even if I had to apply a few times. That’s how I got in the door at Wired Magazine.”

I spent a few years there, but it was like me and sixteen senior editors who never really listened to me, as was their right. That’s just how it was at magazines. And so I left for Gawker where I got a job running Gizmodo, which at the time was small. You didn’t leave a magazine for a blog in 2006, it wasn’t a thing yet. But I knew it was a place where I could do my own thing. And so that’s how I got into being editor-in-chief at Gizmodo. And for five years it was not that different from boxing; being punched in the face every day was actually easier than working at Gawker. It was like so combative internally, so combative externally and you burn all these bridges and you just piss everyone off. But you’re doing that to get the story and get it fast. And I really liked that, but I really liked helping people more, which is what led me to leave and do Wirecutter.

It’s funny, this fall I’ll be at Wirecutter five years, and that’s how long I was at Gawker. But at Gawker, I was thirty-five pounds heavier than I am now, because I was so unhealthy, and so unhappy, and so stressed all the time. So, it’s kind of like I can feel my life evolving in a way that I really like.

“And so that’s how I got into being editor-in-chief at Gizmodo. And for five years it was not that different from boxing; being punched in the face every day was actually easier than working at Gawker. It was like so combative internally, so combative externally and you burn all these bridges and you just piss everyone off. But you’re doing that to get the story and get it fast. And I really liked that, but I really liked helping people more, which is what led me to leave and do Wirecutter.”

What was the impetus for starting the Wirecutter?

I always thought it was really weird when I’d talk to other people who are not into tech, they would ask me, “What do you do?” And I’d go “Oh, I run one of the biggest tech blogs in the world.” But the weird thing is if they weren’t in the tech industry, they’d always ask me this one question, which is, “Oh, I’m trying to buy this, like, camera or this TV, or headphones, or—which thing has thing has this, or—can you help me?” And I’d be like, “Actually, I don’t know.” Like I don’t know. Like I know about all these news things, but you just don’t write about that what people should actually buy.

I just saw this opportunity for this list that was not going to make a lot of traffic, but it would just be this master list of, hey, if you need, like, a $500 TV, this is the one you should get. It sounds like, to some people I describe it to, they’re like, “That sounds like what already exists.” And I’d go, “Yeah, but what already exists will take you, like, an hour to sort through, whereas we only need two minutes to use this list, The Wirecutter. Do you want to save 95% of your time that you spend comparison shopping on this one article that can just help you instantly?” And the answer is yes, and once people use it, they get it.

After leaving Gawker, I had all these really great job offers, but I really wanted to do The Wirecutter. I couldn’t stand the thought of it not existing. So I started out small. I just Airbnb’d my house, and sold my fancy car and just got a cheap truck, and I just started working on it. At some point, the idea just popped. I was just living in Hawaii trying to balance out work and surf, and just everything started to get super amazing. I only expected to do it as a hobby, but it became a real obsession for me.

“After leaving Gawker, I had all these really great job offers, but I really wanted to do The Wirecutter. I couldn’t stand the thought of it not existing. So I started out small. I just Airbnb’d my house, and sold my fancy car and just got a cheap truck, and I just started working on it.”

How did all your time in the blogosphere and the whole tech ecosystem affect your decision-making strategy as an entrepreneur?

I have a lot of disadvantages compared to normal CEO. I think as a journalist you have a lot of common sense and you have a good nose for bullshit, and you need to do stuff that you believe in. The Wirecutter was a concept I could really believe in, but I also knew that, because it was so kind of radical at the time, people were like, “How are you going to be ranked on Google? How are you going to make traffic so you can make ad money?” My pitch was like we are going to ignore a lot of noise and only be updated 10 times a month at most. They’re like, “You’re only going to do 10 articles a month?” I’m like, “Yeah.” Then they’re like, “I don’t know how that’s going to work money-wise.” I’m like, “Neither do I. I’m not sure. I don’t care.” If you’re a VC, you’re probably not going to understand why you should give me money after a conversation like that.

“My pitch was like we are going to ignore a lot of noise and only be updated 10 times a month at most. They’re like, ‘You’re only going to do 10 articles a month?’ I’m like, ‘Yeah.’ Then they’re like, ‘I don’t know how that’s going to work money-wise.” I’m like, “Neither do I. I’m not sure. I don’t care.’ If you’re a VC, you’re probably not going to understand why you should give me money after a conversation like that.”

We got a launch sponsor, Intel, but I don’t think anyone but me understood that we were going to have so little traffic because we were not publishing junk en masse. God bless them. I just also knew that in publishing, you can’t apply those kind of models of extreme growth that you can get from launching a free app that has a free service that grows so fast because it’s all free. You know, like you can’t match that with content. Content’s pretty expensive. Anyone who says it’s not is doing garbage. It just doesn’t grow the same way, and if it does it’s growing because of kind of tricks. So, to do something that’s really high quality, you need to allow it to grow very slow in a way that’s not compatible with most modern, tech-oriented VC, and that’s basically what we’ve done. It took about 2 years before I really could pay myself outside of poverty levels but I didn’t need much. I just kept borrowing money and just living very frugally and I just didn’t want anyone telling me what to do or to do it faster. I think that way was the key.

“Content’s pretty expensive. Anyone who says it’s not is doing garbage. It just doesn’t grow the same way, and if it does it’s growing because of kind of tricks. So, to do something that’s really high quality, you need to allow it to grow very slow in a way that’s not compatible with most modern, tech-oriented VC, and that’s basically what we’ve done. It took about 2 years before I really could pay myself outside of poverty levels but I didn’t need much. I just kept borrowing money and just living very frugally and I just didn’t want anyone telling me what to do or to do it faster. I think that way was the key.”

What metrics have become most important to you?

Metrics? Any two solid metrics that kind of go against each other really work for me.

Sessions is really cool because it rewards my team for not only getting new people but having people return. Having people return is a sign of quality and satisfaction and that’s what we’re going for. On top of that, we’re doing some interesting stuff with data. We ask questions like, “Do you need an 8,000-word article on 10-dollar vegetable peelers?” We’ve also learned that after people trust our work, they only read the first like 30 seconds, and then they stop, and they buy what we recommend.

“After people trust our work, they only read the first like 30 seconds, and then they stop, and they buy what we recommend.”

How many people are you paying regularly now?

Roughly 60, plus freelancers. Sometimes people just think it’s me doing it by myself!

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

The Wirecutter is a really mission-oriented place. So we are not here to make traffic, or be a big media company, or be fancy. We’re just trying to be really useful for people. Shopping really sucks. Everyone has a couple things we’re really excited to shop for, whether that’s leather jackets or surfboards or something that you just will spend unlimited amount of time shopping for. But most stuff’s not like that. Shopping really sucks. It’s such a waste of time and it’s stressful and why even bother with stuff that you’re not that excited about? Helping people with those situations gets us up in the morning. When someone’s like, “Oh, I don’t know what to get. I hate this,” and I can drop a Wirecutter link in front of them like, “Here you go.” That is the most satisfying thing. I love that feeling.

I’m currently using three different things I brought on The Wirecutter for this project.

A microphone?

A little lav and a little recorder and my monitor.

Awesome.

What personally motivates you to do all this stuff?

I think it’s really complex. I love my work so much. I’m satisfied in that regard. But, I would say that, it’s also at the end of the day, we are not our jobs. I have so many things I love to do. I just wish there were 48 hours in a day. Right now, I’d say work takes up 80% of my energy, maybe 90%. I think that’s normal in most people, especially San Francisco friends who work very hard. But that’s not really how it is in Hawaii for a lot of my friends.

You mentioned that in Hawaii, you are not a minority anymore and that is something that you appreciate. I’m curious to know if you experienced isolation or otherness in Silicon Valley?

I think in San Francisco and in tech, I think like being an Asian male is probably the same as being a white male. There is not a ceiling there, or it’s a reduced ceiling. Maybe it’s not on the executive level where you still don’t have a lot of diversity. But San Francisco’s not bad. I think socially, I think in dating there’s discrimination. The data scientist from OK Cupid wrote a book and paraphrasing his findings, he said, “people are really racist when it comes to dating.” The feeling of discrimination is not as strong for me in places where I am not a minority, like in Hong Kong or Hawaii.

Do you have any advice for folks hoping to make it in the big world of tech?

I think you have to take some things really seriously, and then some things not seriously, and you just have to have the wisdom to know the difference. There’s knowing how to work with others, but not following people blindly. There’s a lot of seemingly contradictory advice that isn’t really contradictory if you understand the nuance. Anyone who’s really doing well, in any field, has a bunch of similar traits and mindset. They have these seemingly contradictory things in balance where they do know how to work in a group, but they also are not beholden to groupthink.

What I realized about my friends in San Francisco and LA is that people in California are so much more brave, optimistic, willing to just go for it, than my friends in either Hawaii or New York. I really appreciate that about California, and San Francisco in particular. Everyone is just trying to do pretty big things, if not huge things. That energy is contagious. It’s beautiful to have this example of a peer group that is not afraid to go for it.

“I think you have to take some things really seriously, and then some things not seriously, and you just have to have the wisdom to know the difference.”