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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Tell me more about your first impressions of Silicon Valley.

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

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

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

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

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

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

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

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

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

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

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

She’s in my project!

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

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

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

Thank you.

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

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

That’s good. You’ve earned it.

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

Absolutely.

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

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

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

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

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

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

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

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

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

What are your photographs behind you? What are they?

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

I understand.

Or having like a portrait of yourself in your bedroom.

It’s a bit awkward, I understand.

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

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

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

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

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

Interesting.

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

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

Where do you see yourself in five or ten years?

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

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

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

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

I’m originally from Queens New York, born and raised. I was born in Jamaica, Queens, New York. It’s called 40 Projects. I lived there until I was about 6. Once I turned six I moved to Flushing, Queens, Latimer Gardens Projects. A lot of my life was school of hard knocks, in the struggle. I like to describe my story as that “rose that grew from concrete” story.

I’ve been very fortunate and blessed, quite frankly, to have gone through that because it actually made me a lot stronger, a lot more resilient, a lot more confident in my ability to move faster out of need and necessity. That hunger comes out of nothing other than need. It’s just a part of me now.

Yeah, totally. I know this is a loaded question, but can you share some of those struggles that you faced in childhood that you had to overcome to get where you are?

Well one, living in the projects is not easy. Two, I’ve had to go through the whole welfare thing among other things, right? I had the great fortune to go to boarding school for high school on full scholarship, one of the best high schools in the country. At that point I got to see really how the other half lives. Going to school with Fords and Rockefellers and that sort of thing. It was a really inspiring thing to me because I got to see number one, that I could compete similarly at the highest level and with the best of them. No matter what our upbringings were. It also showed me that I had a hell of a lot to learn.

When I juxtapose my upbringing with that boarding school experience it’s kind of night and day. To be honest, I needed to have both of those experiences to become who I am.

“I like to describe my story as that ‘rose that grew from concrete’ story. I’ve been very fortunate and blessed, quite frankly, to have gone through that because it actually made me a lot stronger, a lot more resilient, a lot more confident in my ability to move faster out of need and necessity. That hunger comes out of nothing other than need. It’s just a part of me now.”

I want to quickly segue to your work now. I personally think you guys are doing the best consumer facing brand work in Silicon Valley. I am a super fan.

Thank you. That makes me feel great.

Tell me more about the brand that you guys have built and your philosophy behind it.

Yeah, my philosophy about branding is I don’t like describing our brand. I’ve got a lesson I learned a couple of years ago from a marketing professor I trust from Stanford. She said “Tristan, brand is not what you say it is, it’s what they say it is.” I really articulate our brand through our customer stories. Fortunately a lot of them are consistent!

I get emails all the time from customers that talk about the success they’re having. I got an email from a woman who said “thank you for finally helping single moms teach their sons how to shave.” Or “thank you for fighting for a product that works.”

You know that’s my story. A pretty important rite of passage. As a young man in the Army, you have to shave everyday. These are the stories that I need to hear, that we’re onto something special. A lot of these stories are incredibly similar. If we can tell those stories through our own kind of authentic narrative, then I think we’ve nailed something and we’ve done it, right?

I’m always hard-pressed to say, “Hey, here’s what our brand is right now” because it’s also so adaptive, but so far it’s been incredibly consistent and told through our own customers stories.

I love it. Tell me a bit more about how you hire and how that has contributed to the success of your company.

I think one thing I think a lot about is this term ‘culture fit’. I think it’s a silly, silly, silly, silly phrase, specifically because no one defines it. It is important to me to really define what that means to people. Before I raised a cent in money, I wrote down the six values of the company. Courage, Inspiration, Respect, Judgement, Wellness, Loyalty. They’re all defined on our website etcetera. It wasn’t enough to just put in on our website. I wanted to entrench it in every single thing that we do. If you get reviews, you are rated according to your goal attainment but also every single one of those values. Are you inspiring? Are you practicing good judgement? Are you being courageous and inspiring?

“I think one thing I think a lot about is this term ‘culture fit’. I think it’s a silly, silly, silly, silly phrase, specifically because no one defines it. It is important to me to really define what that means to people.”

Also our interview process. We’re going to ask leading questions to get at one’s courage. We’re going to ask leading questions to get at one’s loyalty and respect. It provides an objective framework for folks who are not me to scale the hiring process in a way that’s clearly defined. I think that’s contributed quite a bit to a lot of success that we’ve had, and because Bevel is probably one of the most diverse companies on the planet in technology especially.

Yeah, absolutely. Something that’s come up in this project is that VC’s typically invest in problems that they can personally relate to. I’m curious if you experience quite a bit of skepticism building products for people of color in tech…

Yeah, I still do.

And how do you overcome that?

I mean, I overcome it by delivering product that works, building product that people love. To this day, people still don’t think this thing is going to work which is crazy to me because it’s just so clear that there’s such a consumer demand for this. That’s fine. They can think what they want to but we’re just going to keep moving towards our true north which is just delighting our customers and making health and beauty simple. That’s it. I don’t need their validation.

Yeah. I feel you. Another huge thing in this project has been people feeling a sense of isolation not knowing anyone who was like them or came from an unusual background, something that I definitely felt when I worked in tech.

Yeah.

I’m curious about your experience early in your career coming into tech in terms of feeling isolated or not knowing anyone like you and how you feel about it now.

My whole journey here started in 2008 when I came out to go to business school. That was the first time I had even heard about Silicon Valley. I didn’t even know it was a place. I was very lucky to have an email address that had .edu at the end. It allowed me to speak to a lot of folks that I might not have gotten access to otherwise. Fortunately, they saw it as coming from a place of pure genuine interest. For me, the isolation wasn’t there insomuch as my ability to speak to folks. Primarily, it was inability to speak to folks that looked like me. There just aren’t enough people. One thing that’s important is to increase the number of folks. Some of the stuff that we’re doing at CODE2040 really speaks to that because I saw there was a need. Even some of the stuff that we’re doing at Walker & Company. I see bouts of isolation but nothing to really restrict me from chasing ambition I suppose.

“To this day, people still don’t think this thing is going to work which is crazy to me because it’s just so clear that there’s such a consumer demand for this. That’s fine. They can think what they want to but we’re just going to keep moving towards our true north which is just delighting our customers and making health and beauty simple. That’s it. I don’t need their validation.”

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

I think a lot about looking longer term. I want this to be 150 year old organization right? When I’m long gone, what’s the kind of legacy that I hope to leave? There are two things I think are incredibly important here. Number one (and this is the stuff that motivates me), I look at my son.

I want him to be treated as a first class consumer along with anyone else where his interests and needs are respected. Secondly, I want him to know and feel like he can produce at the highest level without bias.

When I think about my motivational driver, it’s allowing and getting him to live in that world.

“I look at my son. I want him to be treated as a first class consumer along with anyone else where his interests and needs are respected. Secondly, I want him to know and feel like he can produce at the highest level without bias. When I think about my motivational driver, it’s allowing and getting him to live in that world.”

Similar question, do you feel pressure as one of the few celebrated founders of color in Silicon Valley?

Well, I mean I’d be lying if I said I didn’t feel any semblance of it. I have a responsibility. I’ve been given this amazing opportunity to give back. Period. I want to make sure that I’m doing right by the folks who have actually given me the opportunity and offering other folks that might be on the come up the same opportunity. Code 2040, Walker & Company, et cetera, I’m dedicating my life to this. I’m doing everything that I can to mitigate any need for that pressure. It’s less pressure and more responsibility. I have a responsibility to not only succeed but also to help others who look like me succeed. That just makes it easier for the next group of folks.

You’ve come up a lot in this project in other interviews.

Oh, very cool. Hopefully good things!

Good things and kind of profound things—like someone literally said “Tristan can’t carry the torch for us forever, you know.”

Nothing will have changed if that’s the case. That’s not something that I want. I say that because there are a lot of people doing amazing things that should be celebrated. Right? I get a ton of interviews all the time and folks reach out to me to talk and I’m like “stop talking to me.” Talk to these folks that really have an interesting story to tell. There are other folks and let’s celebrate them just as we celebrate Tristan because it should be done. There are some other folks who just say that Tristan’s sucking up all the oxygen. I think a lot of people think that I do that purposely. I actually try and … I really, really try to not do any of it anymore. It’s unfair. It really is.

I’m sure you’re frustrated with that, you probably feel like it’s a little lazy.

Exactly.

I get it. I’m really sensitive about it as the founder of this project, of “No, no, no, don’t talk to me. Talk to the people in this project.”

Totally.

“I’ve been given this amazing opportunity to give back. Period. I want to make sure that I’m doing right by the folks who have actually given me the opportunity and offering other folks that might be on the come up the same opportunity. Code 2040, Walker & Company, et cetera, I’m dedicating my life to this. I’m doing everything that I can to mitigate any need for that pressure. It’s less pressure and more responsibility. I have a responsibility to not only succeed but also to help others who look like me succeed. That just makes it easier for the next group of folks.”

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

Look, I don’t think about it. I just think about being the most faithful person I can be. I care about building the most important organization I can and I care about ensuring that my family is taken care of and safe. That’s enough for me to focus on. I can’t really focus too much on the ebbs and flows of macroeconomic stuff. If it’s not for the sake of my own personal business?

My last question for you before I send you off is what advice would you give to folks of similar background who are hoping to get in tech or just getting started.

Yeah, this is the same advice I give to pretty much anybody. I get it from Tyler Perry. What he said kind of fundamentally changed my life. He said “Tristan you realize your potential as an entrepreneur when you understand that the trials you go through and the blessings you receive are the exact same things.” What he meant by that was those trials you go through are just lessons. Lessons and blessings. You have to revel in that. It was the most important thing that I needed to hear because it’s actually made me a little bit more sane as a CEO. It’s given me more perspective. It allows me to focus on the right things right now. That’s something that should not only apply to business but just general life. Right?

That, combined with my own personal faith gives me a strong arsenal in executing my plans.

“Those trials you go through are just lessons. Lessons and blessings. You have to revel in that. It was the most important thing that I needed to hear because it’s actually made me a little bit more sane as a CEO. It’s given me more perspective. It allows me to focus on the right things right now. That’s something that should not only apply to business but just general life.”

I grew up in New York city in the upper west side of Manhattan, which is very diverse. My mom is black and my dad is white so I grew up in a mixed-race household and went to a very diverse public school growing up. And so, I had the quite fortunate experience of growing up surrounded by a very brilliant, multicultural set of people for pretty much my entire childhood.

How do you feel like that’s shaped you in your work?

I loved growing up in New York City. There are a lot of points of independence that I took for granted as a kid there. I mean, I was getting myself to and from school and playdates by the time I was 11. You see everything in New York. You see wealth. You see poverty. You see the best and the worst of society. You see people from all backgrounds. You hear every language being spoken on a daily basis. It’s just such a multicultural upbringing, that I think it really shaped my view of what the world can or should look like.

I’m curious to know if you had any inclinations growing up that you would end up in the tech industry. What did you think you were going to be as a kid?

I never thought I’d end up in the tech industry. As a little kid, I thought I wanted to be a pediatrician, because that was like the only job that I understood. But, I never was interested in tech until coming out to Stanford and spending time in Silicon Valley.

“You see everything in New York. You see wealth. You see poverty. You see the best and the worst of society. You see people from all backgrounds. You hear every language being spoken on a daily basis. It’s just such a multicultural upbringing, that I think it really shaped my view of what the world can or should look like.”

What was the impetus for that?

I felt like I wanted to go back to school because I wanted to learn how to build a better non-profit. I was kind of just disillusioned with the disconnect between revenues and expenses of the non-profit sector. You’re always begging for money. So I decided the quickest way to figure out how to be able to do that was to go to grad school. And Stanford, of all the business schools in particular that I visited, seemed to have by far the most diverse student body in terms of professional background and professional address. It was the only place I went where I didn’t feel like a total freak for trying to do something in the non-profit sector.

I was in Harvard when Zuckerberg started Facebook. There was no (the way there is I think in so many college campuses today) dialogue around entrepreneurship and tech. It was like, “Oh, there’s this weird thing that we log into and you can post your photos.” It wasn’t in my vocabulary until coming to Silicon Valley.

Tell me more about your time at Stanford. Obviously what you do now came out of that, but what were your first impressions of Silicon Valley and of Stanford Academia, and this whole kind of new tech world that suddenly you find yourself in?

My first impression was that I was horrified because you had to drive a car to get anywhere and I’d never lived in a place where that was a requirement! I found it very isolating at first.  I was used to being in cities where you walk around and you see the life and the industry. In New York, it’s obvious how much is going on. You walk out on any street in Silicon Valley and it looks like nothing is happening, which couldn’t be further from the truth. I became more curious as I had more exposure, but I think the main thing was that the mindset out here was so different than what I was used to. The East Coast tends to be more traditional. People here are always interested in the disruption or the next new thing. If you have an idea, the response is often, ”Go for it. Try it out.”

“I sat down with Tristan for coffee. We started talking about the fact that, by year 2040, people of color will be the majority in the U.S. He’d read a book that projected the demise of the middle class as accelerated by the adoption of technology and was in a place of—if this is what’s at risk, how do we make sure that disenfranchised communities aren’t further disenfranchised by the adoption and of technology? That was what lead to the impetus for the idea—how do we make the tech sector more inclusive so that people of color—Blacks and Latinos in particular—are not kind of left further on the sidelines further oppressed as our economy rapidly transitions towards a technology-enabled, technology-driven economy.”

Walk me through the moment of creation of CODE2040.

The moment of creation came about almost a year after Tristan and I had left Stanford. I did a year of business school and was trying to figure out what to do over the summer, and a friend of a friend was starting a tech company and they had a product that was in soft-mode that they were interested in rolling out across college campuses. I had, in another lifetime started a program on a college campus and had this experience in getting a bunch of shoes galvanized around an idea, and they were like, ”Cool. Just take that and write a roll-out plan for the products.” It felt like something I could properly figure out. So I went and joined this company for a summer internship with the roll-out plan. I ended up running the product team, which included kind of a segment of the company. But because my background was not in product development when I took over the work, I took an approach of systems and process design that would allow for maximal creative input and use of data. That led me to work very closely with the engineering team, the QA team, the design team. I got a real appreciation of those skillsets. There is a lot of understanding that I did there as well, about engineers’ needs.

I transitioned myself out of the organization because having a non-technical person running product for a developer facing product did not make sense. I was coming out of that when I sat down with Tristan for coffee. We started talking about the fact that, by year 2040, people of color will be the majority in the U.S. He’d read a book that projected the demise of the middle class as accelerated by the adoption of technology and was in a place of—if this is what’s at risk, how do we make sure that disenfranchised communities aren’t further disenfranchised by the adoption and of technology? That was what lead to the impetus for the idea—how do we make the tech sector more inclusive so that people of color—Blacks and Latinos in particular—are not kind of left further on the sidelines further oppressed as our economy rapidly transitions towards a technology-enabled, technology-driven economy.

What has been the most exciting and activating parts of your work since its creation?

It’s hard to choose. I think that it’s been really exciting to see how individuals have been catalyzed by their time with us. They’re so talented, but a lot of them don’t have the access to the breadth of opportunities that could really launch them into being leaders in the field. But I think one of the most gratifying pieces of what we do has been working with the tech companies. It’s certainly not true across the board, but there are companies out there who feel like they don’t know how to do diversity right. To be a place where those companies can go and have that conversation and get resources, that starts initiate systems change. I think the third piece is probably the hardest to quantify or measure, but is about amplifying others. People on Twitter reach out and are say, “I just want you to know that I am so happy that you are doing this work because I feel less alone.”

What have been some of the biggest roadblocks and struggles as an entrepreneur and in building this product?

It’s been really hard for me to wrap my head around actually being the CEO and what that means in terms of terms of how I act and how people view me. I prefer to empower people around me. To take on as much responsibility as is humanly possible, and probably more than is healthy sometimes. I believe very strongly in distributed responsibility. I believe in a hierarchy, but you push decision making down the chain as much as possible. It’s really hard for me to remember that people really look to me for a specific level of authority and that my title conveys something, rightly or wrongly about who I am and the level of importance that I hold. I think that has been my struggle that has led me to be really slow to make certain choices or improvements in ways that I think has then made my own job harder.

“It’s certainly not true across the board, but there are companies out there who feel like they don’t know how to do diversity right. To be a place where those companies can go and have that conversation and get resources, that starts initiate systems change.”

What were some roadblocks specifically to launching 2040?

They’ve shifted a lot. Initially the big question was, “How do we get companies to believe that there is black female talent out there, that is ‘qualified’?” I would say our first inflection point was two years in when enough companies had had terrific experiences with us, that it switched to entirely inbound companies who want to work with us and hire our students. We ended up throttling our growth. That’s just really hard, period. I don’t know anybody who can solve that well-—anybody who has made that extremely efficient. I’d say for the next two years, that was a real throttle for us. How do we solve those operational expansions? We’re 18 people on staff now but we could have twice as many people and that would be super helpful. But that’s twice as expensive. Now, it’s a matter of how do we create a growth plan that’s really thoughtful and then funded in a way that’s really thoughtful. Now, it’s the question of how and when do we invest for growth. That’s the hardest challenge that we’re facing right now—how do we get the right resources someplace and deploy them as efficiently as possible.

“Black and Latina/o students often say, ‘Why would I want to go to an industry where I can never advance, and nobody’s going to value me and I’m going to feel like an outsider?'”

In watching your fellows move through the industry, what have you all learned through your experience about the cultural and behavioral patterns in tech around people of color?

A lot. We’ve seen a real and really beneficial shift in the narrative over the last four years. When we started CODE2040, the dominant narrative at the time was that tech is meritocracy. If there aren’t people of color in the industry, that’s because they don’t deserve to be there. We managed to move to a place where people were willing to question that assumption, but still felt like, “Well, yeah, maybe they deserve to be there, but we can’t find them. They don’t exist.”

I think people are still trying to figure out what is that other thing that is happening. A piece of it that we know from working with 75 tech companies and close to 200 students in the fall’s program alone, is that there is a culture component. It is a combination of a retention issue, and people who opt out. Black and Latina/o students often say, “Why would I want to go to an industry where I can never advance, and nobody’s going to value me and I’m going to feel like an outsider?”

I think there’s also a growing dialogue now about this false idea of the “hiring bar.” There just is no objective set of standards around hiring. I think what we certainly believe is that there is actually is no good measurement right now. We need to get better at that.

“When we started CODE2040, the dominant narrative at the time was that tech is meritocracy. If there aren’t people of color in the industry, that’s because they don’t deserve to be there. We managed to move to a place where people were willing to question that assumption, but still felt like, ‘Well, yeah, maybe they deserve to be there, but we can’t find them. They don’t exist.'”

What have been your biggest motivators in your work? What at the core drives you?

I’ve always, since I was a kid, had a really strong sense of fairness and justice. It’s not about who’s inherently good, bad, right or wrong, but there’s all these unseen threads that influence how we each act and achieve and show up on a day to day basis. I think that CODE2040 has obviously a strong direct service component. We work directly with students, we’re not an advocacy organization, but we do all that in service of being able to create larger systems change.

How do you think your background impacts the way you approach your work?

Essentially, CODE2040 is this giant code switch for people on both sides. Like how, if you’re a person of color, you had a certain set of life experiences. How do you show up in a room that looks like a tech company? And if you are a tech company, how do you show up in a way that lets people who just don’t approach the world the way you approach the world be included and comfortable? I was in enough diverse rooms growing up that I knew it was possible and that it didn’t have to be weird and uncomfortable. It could be super normal. This whole idea of  discomfort with diversity just never crossed my mind.

“Essentially, CODE2040 is this giant code switch for people on both sides. Like how, if you’re a person of color, you had a certain set of life experiences. How do you show up in a room that looks like a tech company? And if you are a tech company, how do you show up in a way that lets people who just don’t approach the world the way you approach the world be included and comfortable?”

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

In a lot of ways I’m way more optimistic than I was a few years back. I think tech has always been good at iterating and learning and failing forward and all of that. It’s historically been relegated to products and not people and I think we’re starting to see that ethos move into the people’s space as well. But there’s also a big question mark in my mind around—as tech becomes more pervasive across industries and across the country, now what? What does it look like when there’s a thriving tech sector in Austin? In Durham? All these places that have wildly different backgrounds and backdrops than California, both economically, culturally, ethnically, in terms of industry. I think tech in the future is going to look wildly different than it does today and I don’t know what it will look like.

How do you think tech can do a better job accommodating people of color right now?

One, we need to get serious about doing better on hiring. Treating that as a real competency where people are trained and there’s more structure around it. It’s like way too loose right now. So many companies have the intention to be more diverse but don’t actually have the actions to back it up. Tech undervalues HR.

The other piece is recognizing how important culture is and that it’s really hard to change. You have to seed it at the beginning but it’s possible to change it if it’s important to you.

What advice would you give to young folks, people of color, who really like tech and want to get into it?

Find your “tribe.” I find my most effective mentors are my peers, people who have different strengths and skill sets but also people who just have my back and who I can admit my failures to. I think if you’re in a situation where you’re not around your network, crafting a professional one can go a long way to making it feel like a more welcoming and exciting place.

“Find your ‘tribe.’ I find my most effective mentors are my peers, people who have different strengths and skill sets but also people who just have my back and who I can admit my failures to. I think if you’re in a situation where you’re not around your network, crafting a professional one can go a long way to making it feel like a more welcoming and exciting place.”

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

Interesting.

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

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

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

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

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

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

What was it like moving to Silicon Valley?

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

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

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

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

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

For sure.

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

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

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

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

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

Well…

That’s a loaded question, I know.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

When did you start writing about your work?

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

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

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

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

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

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

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

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

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

Let’s talk about your uterus [laughter].

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

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

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

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

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

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

Oh really?

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

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

For real?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[laughter]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Yeah, for sure. So how’d you get out?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Where do you find you support networks? 

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

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

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

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

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

What would you say are your biggest motivators?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

I was born in Richmond, Virginia, nowhere near Silicon Valley or any really tech hub. DC is rising but it’s nowhere near like SF, New York, and LA. I grew up with that cliche story of growing up in a lower income area, growing up in the projects, not growing up with a lot, having a single mother. I try not to harp on that too much because I know there’s so many others that have dealt with that same background and those same problems. But growing up was actually pretty normal to me because when you grow up and struggle that’s all you know. When you don’t see other people who have a lot, you just think living the way you do is normal. You think gunshots are normal. You think drug dealing is normal. You think not having enough to eat is normal. So I never grew up thinking that I had it rough or I had it hard. I knew it sucked at times but I never really felt like we were poor. It wasn’t until I got my first job at 14 and I realized that, “Man, there’s people out here that are doing a lot better than I am.”

Growing up it just felt  really normal. And like I said, when I first got that first job it was at this museum and I started to see white people for the first time. Just imagine like seeing white people on TV and seeing these people but never really integrating with them or interacting with them. Because I came from a side of town that was mostly black and Latino. So I started to see those things, and I saw nice cars; I saw families seeming so carefree and just frivolous about their spending, and I started to realize that there was a whole ‘nother world out there. And then that’s when I really started to get into the internet and really started to research, and I saw that the was a whole ‘nother world outside of what I grew up in.

“Growing up was actually pretty normal to me because when you grow up and struggle that’s all you know. When you don’t see other people who have a lot, you just think living the way you do is normal. You think gunshots are normal. You think drug dealing is normal. You think not having enough to eat is normal. So I never grew up thinking that I had it rough or I had it hard. I knew it sucked at times but I never really felt like we were poor. It wasn’t until I got my first job at 14 and I realized that, ‘Man, there’s people out here that are doing a lot better than I am.'”

And that’s really what made me start to love technology—the ability to connect with people outside of me few block radius and from what I knew. From there it was just working and supporting my mom. You know, my mom didn’t go to college. No one in my family went to college. She worked as a custodian for the Federal Reserve Bank and she didn’t make a lot of money. I was paying a lot of the bills. Like I said, I started working at 14 years old and, yeah, it was definitely a struggle.

Throughout my highschool years, we maintained but there was certain that happened within my family with financial struggles that led to me being homeless. I don’t like to talk too much about my family because I just feel like that’s their business and this is family business and so I kind of like put the focus on me being homeless. I don’t like talking about their situation because I just don’t feel like its right to put out their situation. There was a series of events that led to me being homeless for a year.

“My mom didn’t go to college. No one in my family went to college. She worked as a custodian for the Federal Reserve Bank and she didn’t make a lot of money. I was paying a lot of the bills. I started working at 14 years old and, yeah, it was definitely a struggle.”

It was my senior year of high school and it was really, really a tough time for me. I lived out of my car that didn’t work so I couldn’t even turn the heat on or anything like that it was just parked, and yeah, it was tough. I tried to make it to school—my goal was three days a week. Some days I would have to go to school without showering for a few days.

It was just tough for me because I was always such a social guy and I felt afraid to interact with people because I felt like I smelled or I was wearing the same clothes or things like that. I would do a bunch of different odd jobs like cleaning people’s windshields at gas stations and just hanging around until the owner of the gas station would chase me out or shoveling people’s snow, or raking their lawns, or doing whatever I could to make money and afford a motel for myself and things like that. It was a really, really difficult time in my life, probably the hardest thing I’ve ever done.

“There was a series of events that led to me being homeless for a year. It was my senior year of high school and it was really, really a tough time for me. I lived out of my car that didn’t work so I couldn’t even turn the heat on or anything like that it was just parked, and yeah, it was tough. I tried to make it to school—my goal was three days a week. Some days I would have to go to school without showering for a few days.”

I know breaking through tech is tough, especially for people that look like myself, but finishing school and still making something of myself after that year was probably the hardest thing that I’ve ever had to do. I still was able to graduate high school and make my mom proud. That’s probably my biggest accomplishment.

I was fortunate that my girlfriend at the time, her dad didn’t know I was homeless, but he knew I was in a bad situation. He paid for one college application for me. That college application was to Virginia Tech. Virginia Tech really appealed to me because I was so enamored with tech, technology, computers. I really thought I wanted to be a computer engineer. I ended up going to Virginia Tech, but I didn’t know anything about financial aid or anything like that. So I applied to financial aid late, and I didn’t get enough money to cover my first semester, so I needed to get a job. My first job happened to be a marketing role at United Way. I was able to blend my love for technology with marketing. I was like, “Why does our website look the way that it does? We need to optimize this. Why are we using Facebook to promote our events? Why are we using social media? Why are we collecting e-mails and have a newsletter? Why aren’t we working on our search rankings and things like that. It was just my introduction to technology, and I didn’t know at the time what I was doing. I didn’t know about digital marketing and growth marketing and things like that. It just was like an uncanny ability for me to understand both sides and the tactics to help grow a company. That kind of led to where I am now. A year after that I started my first company at 19 years old, which I actually sold years later. That’s the beginning.

“I used to go to the public library, I didn’t have internet, and things like that, or reliable internet at home. I used to collect the free monthly trial AOL discs just to access the internet.”

How did you first get exposed to tech?

At the local library! At my job we had a computer. I would sneak on a computer and look, and research things, and I saw all the cool things happening. I remember just watching Facebook, and I was so mad because I wasn’t in college and I didn’t have a college e-mail address, and I couldn’t access Facebook.

There’s this cool thing just happening in front of my eyes. Reading all these articles on the web and what was going on, and none of my friends were talking about this, it seemed like a completely different world. I was like a kid in his own imaginary world, it was just great to do that. I didn’t really have any friends or anybody else that was really interested in it because you’ve got to understand when we started becoming teenagers, my friends started becoming drug dealers. My friends were caught up in other things that were street related. They weren’t really worried about tech or anything like that, so it was two different worlds. I used to go to the public library, I didn’t have internet, and things like that, or reliable internet at home. I used to collect the free monthly trial AOL discs just to access the internet.

I just found different ways to play with tech even though I didn’t have the money for it. Though marketing was never anything that I thought I wanted to do. It’s interesting because when I was a kid, I used to sell, which is part of marketing smart drugs by the way. I used to buy like candy and bubble gum and indifferent things, and then I would resell it at a premium price at school. That’s when I really started understanding supply and demand before I even took any business classes. Because I could buy a pack of bubble gum at 50 cents and then sell each piece for 50 cents. I had a love for that entrepreneurial spirit and marketing and selling.  And, when I came over to United Way, there were a lot of things that really made sense to just blend the things I learned about technology and the web.

Tell me about starting a company at 19. How did 19-year-old you have zero risk aversion and just feel like, “I can do this?”

You know what’s so funny? When I started this company, I didn’t tell a lot of my friends. It was one of those things I wanted to try and do on my own. It was all bootstrapped. I was using a little bit of money that I was making from United Way. They started me off at $7 dollars an hour or something like that. I ended up at $9 when I became full-time. Putting a little money away there and was doing a little consulting on the side.

I imagined working as a marketing consultant, doing things that I probably would do now and charge so much money for, for like $12 bucks an hour or $15. I thought I was making bank at the time and I didn’t realize how much they were getting over on me. Back then, you could probably get a whole marketing strategy from me for like $75 bucks. And I thought I got over on you!

Anyway, at 19 I liked to party. In a lot of places there’s a very strong bar culture of 21+ people. I was like, well what about us 18 to 20 year olds? There’s tons of us and we don’t really have anywhere to go. So I created a platform. I created a strategy where I would take these events and I would go to different warehouses, or clubhouses, or restaurants, or wherever, and throw parties and live events there where you didn’t have to be 21. You didn’t have to drink there and people 21+ joined too. They thought  “Oh, these parties are happening, these live events are cool.”

Then I match that with my love for technology and digital where I really implemented Facebook as a strong growth driver for my events. I was lucky back then. Facebook events started coming out, it was like a strong driver for growth of getting people involved in the events, and then also setting up my own digital platform for the company where people knew that you could keep updated with all our different events and things like that.

One of the biggest drivers of growth was photography. You have to remember, this is back in 2007, 2008, when people didn’t have these fancy iPhones, with these great cameras. When people came out to our parties, you could get a really nice picture done, and you knew that one or two days later, you’d be able to see those pictures on our platform. Also on Facebook as well and different Facebook groups. We were able to blend tech, the digital space with photography, with live events that kind of make a really, really cool company.

It was really successful for a while and it died down a little bit when I started getting more into my academics. Then I started up again and it was doing moderately well, but then I actually had someone who was in the live events business that wanted to kind of adopt my model. By this time, Instagram had came out and all that stuff, so our photography hook wasn’t as strong. So they bought my company. It wasn’t like a huge amount or anything, but it was the most money I’ve ever seen in my life, and it was a huge, a huge, huge accomplishment for me. Life changing.

So then you ended up being a marketing executive in your early 20s.

I did. So I sold my company and also I was working for Neil Strauss, famous author and entrepreneur, radio host. He had really popular books like The Game and Emergency and things like that. The Game is probably his most famous book. He used to write for Rolling Stone. He has his own masterminding group. He also has his own radio show on Sirius XM, so I was doing digital initiatives and digital marketing for him.

Sean Ellis reached out to me, which most people in the tech industry know as the most famous marketer. He’s known for coining the term growth hacking, by growing companies like Dropbox, Eventbrite, LogMeIn, Uproar – numerous IPOs, numerous billion dollar companies, and he gave the keys to marketing for his company to a 23-year-old kid, and it was really, really exciting.

We worked on Qualaroo together and got to the point of being profitable. We all know working in start ups, especially SaaS businesses, reaching profitability is hard. To help with marketing and lead a company into the green was really exciting. Along with that, starting GrowthHackers.com with him and that turning into its own entity in this own company itself. It was a very exciting time for me as a marketer. It really strengthened my skills and my technological skills, and my marketing skills during that time was awesome. At the time I was running marketing and I end up becoming the head of growth over at GrowthHackers.

“I would literally work maybe like 6:00 AM and work until 7:00 pm. On the way home, I would stop at Subway every single day. I would grab a tuna sandwich. I’m a man of habit. I would grab a tuna sandwich, scarf that down, get home, and literally start working on projects and different things that I was doing until  3:00 or 4:00 in the morning.”

At the same time, I started MilliSense, which is my marketing firm that I am CEO of today. I was having a conversation with my mom, and I was like, “Hey, I have all these people coming to me about consulting or whatever. It’s killing me tax-wise. Look, I need to start something, start a company.” I’m sitting there with my mom, and I’m just like, “I really want to dedicate something to her.” I was like, “Hey mom, I want to name my company after you.” And she was like, “No, no you’re not. Whatever.” And I remember sending her pictures when I got the LLC and things for MilliSense. The name comes from my mom’s name, which is Millicent. And because my mom always made sense of things.

That’s what we kind of do when we work with a lot of tech companies, a lot of startups, a lot of companies that are boot strapped. I try not to take that mentality of those agencies or marketing firms that try to overcharge people and things like that. I really want to help entrepreneurs and people be able to accomplish their dreams. So there’s really no set price for us to do things. We’re all about negotiating.

I would literally work maybe like 6:00 AM and work until 7:00 pm. On the way home, I would stop at Subway every single day. I would grab a tuna sandwich. I’m a man of habit. I would grab a tuna sandwich, scarf that down, get home, and literally start working on projects and different things that I was doing until  3:00 or 4:00 in the morning. It was pretty crazy.

I was running growth and doing stuff for growth hackers while running various other projects. I was reached out to by Sticker Mule. I was 25 years old at the time, and they offered me the opportunity to be their chief marketing officer at 25 years old. It was a huge opportunity, because a lot of people aren’t aware of Sticker Mule. Sticker Mule isn’t your average start up. It’s really a mid-size business, but the revenue they’re generating, the number of employees that they have, made it a major operation. To manage a marketing team of that size and be a C-level exec at a company like that was amazing. I was able to have a lot of success there and it really built my profile even more. We grew revenue almost 50% during my time there. We almost tripled website traffic. I was so nervous going into that role, and I did my thing. It was great.

I was balancing that with MilliSense, so I was CEO of MilliSense still, while serving as CMO of a multi-million dollar company. Call me crazy.

That is crazy. I’m so curious. Your hustle comes from your background for sure. But I’m also curious, you were able to confidently go in as a consultant as a teenager, and you were charging just $12 an hour, but you were still selling it. I’m curious to know, where did you get that belief that you could do it? You know what I mean? It’s like you didn’t get that crippling gene of self-doubt.

Actually, I would disagree with that. I’m my biggest critic. I doubt myself a lot. I just don’t allow self-doubt to prevent me from accomplishing the things I want to do and making my dreams happen.

One of the people that worked at United Way with me, her friend had a small restaurant in Blacksburg and just needed help with creating a Facebook page and doing some social media stuff and marketing, and she was like, “Hey, you know, I’ll pay you $10 an hour to help me out.” And I was like, “$10 an hour. Yeah, I’ll absolutely do this.” So once that happened, there was a chain of events where just word of mouth, and then it just made me more confident that I could do the things that I could do and be able to say, “No, I actually want $25 an hour or $30 an hour or $50 an hour.” It kind of just spiraled from there, but yeah, I go back and forth in my head about a lot of things all the time. Sticker Mule was one of them, and that was one of the latest things that I did.

“I’m my biggest critic. I doubt myself a lot. I just don’t allow self-doubt to prevent me from accomplishing the things I want to do and making my dreams happen.”

By the way, to update, I’m back and full-time as CEO of my company, MilliSense. I’m also working on some software to go along with the consulting service as well, which I’m excited about. I’m also full-time with Microsoft as a consultant. We’ll try to do the numbers, try to figure out the numbers, but I’m working on new projects with Microsoft that I’m really really excited about. I’m leading growth and marketing strategy.  It’s cool to get enterprise experience on a tech level too.

I’m pretty sure we’re going to talk about struggles later. One of the biggest things was, it is an absolute bias in Silicon Valley about working at a Google, Facebook, or Twitter, or Yahoo beforehand and you will just not have doors open up to you if you hadn’t worked at one of those companies.

Yeah, why don’t we just dive in, tell me more about your experiences with big company bias.

That’s been really tough for me because I understand my skill set and my abilities and I know I can do that at a larger scale, but I’ve literally been turned down by some really successful companies for roles because they told me I didn’t have the enterprise experience. That’s really disheartening to me because I feel like the things that you have to do at a small or mid-sized company pales in comparison to some of the things that you have to do at an enterprise.

“There’s also a bias for people who speak out on diversity, that speak out on social issues, that are voicing their opinions and not being quiet.”

My friends that have worked in enterprise companies don’t realize what it feels like to know that hey, if I don’t work today that literally might affect the bottom line of my company, my livelihood and so there’s a lot of bias there if you haven’t come from one of those companies.

That leads to a whole slew of problems because people that look like me aren’t at those companies or aren’t getting those opportunities especially if you didn’t come from a Stanford or some Ivy League school or whatever. It’s really, really disheartening and the you see the new Unicorn companies the Snapchats, the Ubers the IBMs, what are they doing? The exact same thing! They’re trying to get the Google people, the Facebook people, and they want people with the same pedigrees that look like them.

It’s a wheel that keeps turning. It feels like you’re not going anywhere. No matter all the success I’ve had, the credentials I’ve built, a lot of people will say, “Oh, you’ve made it,” and they don’t realize there are still a lot of doors closed to me just off the strength of big company experience.

There’s also a bias for people who speak out on diversity, that speak out on social issues, that are voicing their opinions and not being quiet. The one thing I’ve noticed about many people that I’ve met, black employees at the Googles, and the Microsofts, and the Apples,  they stay in their lane. They stay and keep that cookie cutter image no matter how they may feel internally where they won’t speak out on things, where they won’t step out and be who they really are because they know they have to fit this certain image for this company.

It’s really disheartening that some of the more successful people had to do that. I’ve actually ran into this at companies I’ve been at where they say, “Hey, you can’t really speak out on these things,” or “You can’t say the things you do because our customers see that and things like that.” I can’t be a part of a company where I can’t speak my mind, and stand up for the things that I believe in, or the things that I feel that are unjust.

It definitely closes doors to you because they’ll see you not as a person, but as a problem. They’ll see you also as someone who has their own personal brand. You look at a company like Snapchat– can you name one person at Snapchat that has a personal brand outside of Evan Spiegel? Everyone just falls in line. I think you should be able to try to be the best person that you can be. Unfortunately that doesn’t happen a lot of times in tech.

“I can’t be a part of a company where I can’t speak my mind, and stand up for the things that I believe in, or the things that I feel that are unjust.”

You mention you touch on your experiences with age bias and retro bias and your pre-interview I’m curious to hear more about your experiences.

On age and racial bias – Before I took a job with Sean, I was applying to a lot of tech jobs, and I wasn’t getting responses back. I had a LinkedIn profile, I had a really good resume, I had run marketing at a few different companies, I had successfully sold a company, and I still wasn’t getting responses back, and I couldn’t figure it out.

My spidey senses were tingling when it came to racism, and so I created a fake LinkedIn page with a white person stock photo, changed up the name to be very, very let’s say proper, and pretty much had the same resume. I sent this out to 10 people, because I’m all about testing. I sent the A/B testing racism here in the 7 out of 10 people that didn’t respond to me actually responded to that fake profile.

You probably tried to find me on Linkedin and you realized I don’t have one. I never felt the need to use Linkedin because I just was so turned off from that experience. I know a lot of people that are judged by their Linkedin profile. The color of their skin. The way that they look. I deleted my profile and I was just like, “Man that’s sucks.”

“I created a fake LinkedIn page with a white person stock photo, changed up the name to be very, very let’s say proper, and pretty much had the same resume. I sent this out to 10 people, because I’m all about testing. I sent the A/B testing racism here in the 7 out of 10 people that didn’t respond to me actually responded to that fake profile.”

It is similar with young people. I even talked to–I’m not going to name his name, but he is a white young male CEO of a successful startup right now. They’ve raised millions of dollars in capital, and he said that to get a job he actually had to photoshop his face to make him look older in his linkedin. That’s coming from a white male, so there’s definitely ageism and racism when it comes to this stuff.

I’ve literally been told, “Hey, you need to wait your time and put in more time.” And things like that. That is completely related to age, because as far as the steps I’ve needed to take to get to where I am, I’ve been successful.  Everywhere I’ve went I’ve got the experience. I have proven results. I’m not a person who doesn’t have results. I’m all about data, and so the fact that people still judge me off my age is crazy. I used to wear that as a badge of honor because I was like, “I’m 25, I’m 24, I’m 23, and I did this? I thought that was awesome.” And then I started to realize that a lot of people resent that unfortunately. Because a lot of people look at you like, “Hey, when I was 25 I was still a product manager making $50,000 at wherever, and you want to be a VP.” So it’s tough.

“I’ve literally been told, ‘Hey, you need to wait your time and put in more time.’ And things like that. That is completely related to age, because as far as the steps I’ve needed to take to get to where I am, I’ve been successful.  Everywhere I’ve went I’ve got the experience. I have proven results. I’m not a person who doesn’t have results. I’m all about data, and so the fact that people still judge me off my age is crazy.”

On the racial side, there is just blatant ignorance when it comes to the skills and abilities and people of color. Like, people just literally look past us and think that we’re not equipped, or because we look different or may dress different or not come from the same background as you that we can’t do this job. I’ve actually been turned down from jobs which should have been like my expectations and things like that because I feel like people judge me for things outside of my work and my resume. So it’s definitely been tough.

I remember when I was head of comms, and like 22 years old, and I act so much younger now than I did then, because if anyone found out how young I was, their demeanor to me immediately changed, and they literally started treating me like a tiny girl-child, but I just pretended I was in my 30s my whole early 20s. It was the only I could be taken half-seriously.

I’m also interested in talking about kind of anti-marketing bias, like I worked in comms for instance, which is non-technical.  Even though growth hacking is very quantitative and data driven, it’s still kind of lumped into that soft-skill or not-necessary-skill category. I’m curious to just hear your thoughts on that bias.

Yes, it’s so bad. It’s really, really bad because a lot of people are from that engineering background, and they think marketing is so trivial. A lot of engineers I’ve met, surprisingly enough, think they’re good marketers. They think that they understand, and I’m like, “You’re not, you’re not a good marketer.” And it’s almost like– I’ve come across a lot of engineering founders that is not more so, not that they’re looking for marketing help because they feel like they need someone else’s expertise, but because they don’t have time for it.

They still, in their heads, think that they are the best marketer for the company and things like that. And that’s really, really, really tough to deal with. And whenever I come into a new company, it’s almost like a stare down with the engineers. You got to prove that you’re not going to back down, and that you understand the things they’re doing, you understand the lingo. I would say this to a lot of marketers with in tech. Even if you don’t learn, learn how to speak, learn the lingo. Learn, and maybe to do basic things so that you can at least have conversations with these people.

Make sure that everything you’re doing can be proved with data because that’s what they’re going to respect. A lot of engineers think we’re just people that just come up with ideas and thought at a wall, but if you come in and you have an actual organized disciplined data that you’re having processed, they’ll respect you a lot more. I feel like marketers have the shortest leash when it comes to start-ups and tact.

“Make sure that everything you’re doing can be proved with data because that’s what they’re going to respect.”

I know engineers that are chilling, they just do the minimum and especially if you have a founder that’s not technical. Engineers get away with murder especially if they don’t understand what the engineers are doing. Marketers they give brain for everything and a lot of times it’s stuff that has to do with market fit and the product still needing to be developed, but if the product isn’t selling and the marketer’s getting blamed for it.

I was actually just having a conversation with somebody growth hacking. It is like that cool thing in tech right now but it’s tough because people look at us, is like these unicorn marketers that are supposed to just come into your company, and then, boom hockey stick growth and that’s not the case. And so, a lot of the guys that I know that work in growth and marketing are at places maybe, 8 to 12 months and that’s it. These are the people that get blamed for when the product isn’t selling, when they’re not getting traffic and things like that, and is not looked at engineering product.

So, that’s probably been the toughest thing for me. I was mentoring at a tradecraft in San Francisco, and one of the things that I told him was that to be a growth marketer is a nomadic lifestyle within start-ups and Tech, because when things go wrong, you’re going to be looked at first. And you’re going to be the one that is let go, or you’re going to be the one that gets to blame. And so, just realize that if you want to be a marketer at Tech unless you’re at a big company where you more relaxed like in Facebook or things like that, you’re going to be jumping from company to company, because you’re going to get into a lot of bad situations.

What are the things that you love about being your own boss and approaching work that way?

The biggest thing that I love is – and you don’t hear me talk about it a lot – is being able to give back to the community and do volunteer work. I don’t have to worry about meetings and calendars. I’m able to volunteer every week and do the things that I love to give back.

I remember being cooped up in offices at startups, working from dusk till dawn on projects and not having time to myself. To have that flexibility to do the things I love and to be able to give back, and to travel. A lot of my travel is related to business. I’m headed to Boston, then St. Martin, then Beijing and Nevada and all these places but even though is work related, I still get to enjoy traveling and doing things.

I could say that, because I’ve built something for myself and that feels really good. I don’t feel like I’m a slave to someone else’s company or beliefs, or whatever. I’m able to speak freely and do the things that I want to do, because I know that I’ve built a skill for myself and I’ve worked hard, and I say this with the most humility, that I know that I have talent. I know that I can bring something to the table, and so, because I continuously work every single day to get better as a marketer and as a leader. I have that value proposition that you have to let me be who I am if you want to work with me. That’s what’s been great so far and has led to a lot of great opportunities, and I’m loving it.

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

They think I’m a celebrity.  No one from where I’m from really makes it out, or does these things, or is printed in magazines, and have articles written about them, or get to be interviewed by people like you. This doesn’t happen. It’s all pretty crazy to them. They still look at me like the same person though. They’re still going to make jokes about me. They’re going to still be hard on me, but at the same time they are definitely enamored with the idea that so many people are appreciative of my story. People want to hear from me and want to work with me and they’re definitely really, really proud. That’s something that means the world to me. Got to keep pushing!

How do you feel about the state of tech in 2016? What’s really exciting to you? What frustrates you?

I’m very excited about the overall interest within the tech industry and how everyone’s kind of throwing their name in the ring. I know some people don’t want other people invading Silicon Valley. They don’t want so many people gaining interest. What they don’t realize is that these mainstream people or people from different places gaining interest will only affect the youth.

When I get to talk to kids from back home, and I tell them about how basketball players and celebrities are involved in tech. It’s just really inspiring to people. I really like the work that CODE2040 is doing. Black Girls Code and all these different organizations raise interest within the black, Latino, and minority communities and movement into tech. Those are the things that I’m most excited about, personally.

“I don’t really see any change when it comes to diversity. I hear a lot of people talking and then you see the actions of people and it doesn’t really change. That’s really disheartening for me to see within tech, that I really feel like things are not going to change. When you look at these companies that are talking about diversity and how much they want to change, you’re like, ‘Yeah, they’re going to change.’ Then you look back in 2012, and they were saying the same thing and still have the same numbers.”

The thing that I dislike is this whole unicorn bullshit and these crazy wild valuations, talk about how the bubble is bursting, how that’s affecting actual, real quality startups that’s coming out now, that are struggling to get funding because you’ve had so many of these flops or these companies that got way too much money without any type of validation.

I think it’s just going to be really, really tough for people. All the startups I’ve started, it’s all bootstrapped. It’s all stuff that I did myself, so I’ve never had to raise money for any of my companies. It’s now a really, really tough time for that.

I don’t really see any change when it comes to diversity. I hear a lot of people talking and then you see the actions of people and it doesn’t really change. That’s really disheartening for me to see within tech, that I really feel like things are not going to change. When you look at these companies that are talking about diversity and how much they want to change, you’re like, “Yeah, they’re going to change.” Then you look back in 2012, and they were saying the same thing and still have the same numbers. So that’s something that I don’t really like as well. There’s a lot of things I don’t like, but I won’t harp on them. Hopefully, they’ll be changed.

People have to understand that having white women at your events and conferences does not mean diversity. Yes, a white woman is diversity, but a lot of people, it was like, “Oh, we have have a black man and we have a woman, so we have black representation and woman representation.” No, you can have a black woman and you can have a Spanish woman, you can have a Native American woman, you can have different women of color at these events. Just because you have a woman there, does not mean that you have diversity, and I absolutely hate that. It annoys me so much. Or just try convincing conferences that just don’t have any color at all, and I’ll call them out. I’ll call them up. People think sometimes that I’m calling them up because I’m jealous because I’m not speaking there or whatever. That is absolutely not the case. It’s just like, I just want to see people who look like me. I want to see people from diverse and different backgrounds speak at these events. And I feel like there’s so many people to choose from and you just don’t see it at all. I could probably go on and on about things that I hate about tech in 2016, but, yes, that’s some of it.

“People have to understand that having white women at your events and conferences does not mean diversity.”

What advice would you give folks who come from tough backgrounds, backgrounds similar to yours, who maybe want to get into tech, but don’t feel like it’s even possible?

Well, first of all, I would say build your skills. There’s so much free information online. You can learn how to code online. You can learn different marketing skills online. There’s so so many different things that you can do right online to build your skills. There’s going to be a lot of people that don’t give you an opportunity or chance.

Create things for yourself, it’s so easy to set up. Like the Shopify store where you’re selling some T-shirts or whatever. It is to prove that I can do marketing. Look I’m 18, 19 years old and I sold $20,000 dollars in T-shirts in a year. That might not be a lot, but that’s a lot. That’s crazy to do that at 18 or 19 years old.

“Just because you have a woman there, does not mean that you have diversity, and I absolutely hate that. It annoys me so much. Or just try convincing conferences that just don’t have any color at all, and I’ll call them out. I’ll call them up. People think sometimes that I’m calling them up because I’m jealous because I’m not speaking there or whatever. That is absolutely not the case. It’s just like, I just want to see people who look like me. I want to see people from diverse and different backgrounds speak at these events. And I feel like there’s so many people to choose from and you just don’t see it at all.”

You start putting a portfolio together of the work you’ve done. Whether you’ve built apps, or built websites, or you started a blog and you’re able to push this much content. It’s never too early to start working on your personal brand as long as you have built skills to go along with that and expertise to go along with that. Just start building that brand for yourself and have value that you can bring.

Don’t get discouraged because the Googles of the world and the Microsofts and Apples or whatever don’t want to hire you. There’s a lot of small, bootstrapped companies that need your help. Do whatever you got to do. If they’re barely paying you, then work nights and weekends and do whatever you have to do but just gain that experience as quickly as possible.

“Don’t get discouraged because the Googles of the world and the Microsofts and Apples or whatever don’t want to hire you. There’s a lot of small, bootstrapped companies that need your help. Do whatever you got to do.”

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 grew up on a farm in Oregon in the 1970’s-80’s. My dad built a computer for me and my siblings in the late 70s when I was in grade school, and I still have it. It has a wooden case. You can’t plug it into a TV anymore, because that sort of TV doesn’t exist anymore, but it’s how I first learned how to program using BASIC. It had a cassette drive that connected to it to store and load data. I would write one program at a time or I’d copy a program out of a book. Then I’d be able to play PacMan or Caterpillar, or some game I wrote, for hours and days. That computer was one of the best things that ever happened to me.

I went to college at University of Washington in Seattle, and by then I had gone through a Commodore 64 and a couple of Macs: first an Apple II and then a Mac Classic. I finished degrees in statistical computing and economics at University of Washington in 1993, where there were very few women in programming and statistics.

“I grew up on a farm in Oregon in the 1970’s-80’s. My dad built a computer for me and my siblings in the late 70s when I was in grade school, and I still have it. It has a wooden case. You can’t plug it into a TV anymore, because that sort of TV doesn’t exist anymore, but it’s how I first learned how to program using BASIC. It had a cassette drive that connected to it to store and load data. I would write one program at a time or I’d copy a program out of a book. Then I’d be able to play PacMan or Caterpillar, or some game I wrote, for hours and days. That computer was one of the best things that ever happened to me.”

After university I went to work for a startup cell phone company called McCaw Cellular. I was a statistician and used neural nets to do predictive modeling. I worked in the database marketing group and did analysis to predict whom to target with marketing based on how they were using their cell phones (analog phones at that time—bricks and flip phones). I was analyzing data with a Sun SPARCstation running HNC neural network software and SPSS. The SPARCstation was one of the fastest desktop computers at that time and now they are essentially doorstops—they didn’t even have 1GB of RAM and they were considered fast and powerful. [laughter]

McCaw Cellular owned the Cellular One networks in the United States and they were the largest cellphone company in the early 90’s. While I worked there, they were bought by AT&T and became a part of AT&T Wireless Services. About the same time that AT&T was buying McCaw, NCSA came out with Mosaic—the first graphical web browser. Mosaic turned into the first version of the Netscape web browser. I decided that creating things in HTML was more interesting than analyzing data and I looked for a job in San Francisco. I moved to San Francisco in 1996.

I worked for a small web company—now a huge web company called Organic Online—as their QA Manager. I left Organic to work for a startup called Electric Minds. That startup died about four months after I started there. It was 1997 and there was a lot of demand for freelance work. I started doing consulting work and then started my own consulting company.

“During the 17 years that I was the head of my own company, I would often go to meetings with prospective clients. If I brought along a man, who worked with/for me, then often the prospective client would assume he was my boss. Repeatedly—that experience never faded over all of those years.”

I named the company OTIVO and we provided a variety of research and testing consulting services—browser compatibility testing, automated testing, accessibility testing, server performance and load testing, user research and user testing. The company grew from just me to 30 people and then the NASDAQ crashed in the spring of 2000. By the end of 2000 the company had reduced to 5 people, as the dotcom bubble burst and hundreds of companies (including our clients) died.

I ran that consulting company for 17 years until I started at Dropbox about two years ago. I wanted to work with a team in a larger company and be a part of projects that lasted longer than a consulting role.

During the 17 years that I was the head of my own company, I would often go to meetings with prospective clients. If I brought along a man, who worked with/for me, then often the prospective client would assume he was my boss. Repeatedly—that experience never faded over all of those years.

“I’m acutely aware that diversity in the tech industry has progressed very little since I first started working in tech in 1993. It was mostly men then, and now, 23 years later, it’s still mostly men, particularly in engineering, product, design, and sales.”

In the fall of 2013 I put together a resume (which I hadn’t done since 1996), let everyone know I was on the market, and researched how to interview for jobs.

I joined Dropbox in May 2014 and started to grow a research team.

Tell me more about your philosophy behind growing a diverse research team at Dropbox.

I’m acutely aware that diversity in the tech industry has progressed very little since I first started working in tech in 1993. It was mostly men then, and now, 23 years later, it’s still mostly men, particularly in engineering, product, design, and sales. As I was interviewing dozens and dozens of people for research positions (to grow the team), I made a plan in my mind to create a diverse team.

A lot of people think that it’s hard to hire a diverse team in tech. It’s not. I think it’s all about where you’re looking for hires and how you’re evaluating their qualifications. If you’re relying on referrals, then you’re going to get more people like you. If you’re only looking at people from specific universities or specific companies/industries, then you’ve narrowed your pool of potential hires to a small group (who are probably fairly homogenous).

Look outside your networks, look outside specific roles, take a second or third look at a resume that you dismiss. If you don’t know the school or the company or the industry or the roles, do some research. Often you will find smart creative people who are a good fit for the role from other industries/companies/universities/roles who can apply their experience and skills very adeptly to the role you’re hiring.

“A lot of people think that it’s hard to hire a diverse team in tech. It’s not. I think it’s all about where you’re looking for hires and how you’re evaluating their qualifications. If you’re relying on referrals, then you’re going to get more people like you. If you’re only looking at people from specific universities or specific companies/industries, then you’ve narrowed your pool of potential hires to a small group (who are probably fairly homogenous).”

I hired a very diverse team of 20 people—millennials to genX (genX is “old” in the current tech industry), from a lot of different backgrounds, including different schools, races, genders, and cultures, and from a variety of different companies and industries. Some with kids (which is also not common in the current tech industry), and some queer and some straight. That team is the most diverse team at Dropbox.

Then, in February 2016, I changed my role and moved to the Marketing team. Most of the team I created has stayed in Design.

“Look outside your networks, look outside specific roles, take a second or third look at a resume that you dismiss. If you don’t know the school or the company or the industry or the roles, do some research. Often you will find smart creative people who are a good fit for the role from other industries/companies/universities/roles who can apply their experience and skills very adeptly to the role you’re hiring.”

Sometimes I wish I hadn’t joined the tech industry. In college, I was recruited to become an actuary (because I scored high on their tests). At the time, the biggest reason I didn’t consider that job is because I was told I would have to wear a dress or skirt to work. My pants and jacket weren’t acceptable office wear. That was only 20-some years ago. While the tech industry is great for individuality of expression as far as not caring whether most men or women wear dresses or suits, it doesn’t mean that women achieve the same heights of leadership. It’s disappointing, to me, that it’s 20-some years later and that great individuality of expression hasn’t bridged the diversity divide, and we’re still in some ways talking about the same (or even bigger) issues with diversity in tech.

How do you think the culmination of your background and life experience impacts your approach to research and building teams?

When you do research for a product that has hundreds of millions of people using it, then you know that those people have two things in common: (1) they’re human and (2) they’re using some device to access your product. If you’re a team that’s doing research to represent the people who use your product (or, by same logic, if you’re a product manager or designer or engineer building/designing product for those people) then it helps to have a team that represents those hundreds of millions of people.

“The more diverse your team is, the more you’ll empathize with a wider swath of the people who use your product, and the better your product will become for the people who use it. When the team gets together to meet, then there are a lot of different life experiences and perspectives to improve the discussion.”

The more diverse your team is, the more you’ll empathize with a wider swath of the people who use your product, and the better your product will become for the people who use it. When the team gets together to meet, then there are a lot of different life experiences and perspectives to improve the discussion.

For example, everybody can look at a chair and say it’s blue, but if you ask if about the chair’s style, then everyone will use their subjective experiences and knowledge and data to say something different about the chair.

Of course, you can do amazing work and create excellent products with a homogenous group. However, I’ve worked with hundreds of different teams throughout my career and have noticed that more ideas are created with a group that has more differences. It’s simply because how you experienced life lends differently to the work that you do.

For example, I grew up on a farm, you grew up in a city, I went to a public school, you went to a private school. Those experiences will give both of us different viewpoints and perspectives that will give me ideas and you ideas we wouldn’t have thought of on our own.

It’s important to show up and be yourself in tech, particularly if you aren’t a part of the majority. We all have limited time here on the planet and we’re all better for the experience of working with and collaborating with and hanging out with people who are not like us. I learn better and work better when I’m around people who aren’t all just like me.

“Of course, you can do amazing work and create excellent products with a homogenous group. However, I’ve worked with hundreds of different teams throughout my career and have noticed that more ideas are created with a group that has more differences. It’s simply because how you experienced life lends differently to the work that you do.”

I’m a middle aged lesbian, and a mother, so it’s super easy, in the tech industry, to work with people who aren’t just like me (middle aged lesbians with kids are usually a minority in tech). But I could, of course, go back to consulting, or find a company that has more people like me, and be familiar and comfortable and, quite frankly, be completely bored.

Our experience at work is made better when we work with and talk with people who didn’t have similar life/work/education experiences. We find that we all have human experiences in common that aren’t necessarily defined by demographics or university affiliations.

In your personal experience, what have been some of your biggest struggles in the industry, either as a woman or part of other minority groups?

There was an article in the New York Times recently about why young women aren’t identifying with Hillary Clinton and there was one piece in that article that really struck me. It’s that young women in college haven’t been in a workplace yet so they don’t identify with somebody who talks about workplace struggles because that’s not something that’s happened to them yet. But women over 30 tend to identify more with Hillary Clinton because, when she talks about issues in the workplace, those women have already been in the workplace long enough that they’ve seen things happen, and they realize, “Oh, yeah. This is true.” That was me in my 20’s—I’d had a few experiences of gender discrimination but I wasn’t yet a parent and I hadn’t yet had decades of work experience and micro-aggressions and discrimination based on my gender.

I’ve noticed, anecdotally, that it’s sometimes more difficult for women to get promoted because it’s the men who are doing the promoting and they tend to promote other men. I’ve noticed this across dozens of companies where I’ve consulted or worked—not any specific company. The people who are in charge of hiring or promotions often tend towards hiring and promoting the people who look like them.

“I’ve noticed, anecdotally, that it’s sometimes more difficult for women to get promoted because it’s the men who are doing the promoting and they tend to promote other men. I’ve noticed this across dozens of companies where I’ve consulted or worked—not any specific company. The people who are in charge of hiring or promotions often tend towards hiring and promoting the people who look like them.”

This means that if you’re a woman you have to do more to make yourself stand out and be noticed, because you don’t just automatically stand out and be noticed because you don’t look like the people who are making the decisions. That was the theme in the article about Hillary Clinton. In my experience, most women I’ve worked with have experienced or heard stories of seeing men get promoted and recognized when the women are doing exactly the same work. I would love to see someone do research and put hard and fast numbers on this but, since this happens inside of groups and teams, you can’t easily do research on that.

You’ve stuck it out and there are positives to your career. And you’ve done a lot of amazing things. I’m curious, what’s the glue that holds you in place? What are the things about your work that really continues to activate you and what else is keeping you here? Is it support networks? Has it been mentors?

I love the tech industry for the challenges and problems to solve. There’s always more to do than time in the day and it forces prioritization and organization. I like working on a team of people who are working on different projects. I started to get lonely towards the end of the 17 years of running a consulting company. It’s more social, with more opportunities to get to know different perspectives, in a larger company.

I saw a friend of mine recently who has also been running his own consulting company for a while, and he asked me, “Do you miss it?” And I immediately responded, “Absolutely not.” As much the continued diversity issues in tech frustrate me, I still love working in tech.

I like it for working on problems and solving things, or not solving things, or creating things and failing, or creating things and succeeding. It’s much more interesting to me than the consulting work I did where I’d work with a company for four months, work on one thing and then leave. I like being in a more dynamic atmosphere. Tech gives you that, and other industries give you that too—medicine gives you that, law can give you that, politics gives you that. There are a bunch of different types of work that give you that.

“There’s a stereotype of women, of moms and of grandmas, of not being tech-savvy (though most women over 70 are quite tech-savvy). Also there’s an assumption that I often hear, that if you’re over 40 or over 50 then you aren’t a tech native and you probably have a hard time with technology compared with a millennial. I’m not offended. When I hear this (at least once/week) then I point out that I’m one of billions of people in my age group who know how to do a lot more than just turn their phone on and off.”

Back to ageism, I’m curious to know if you have started experiencing any. You joked about being people’s mom’s age, but I’m curious to know if you’ve started experiencing what might be microaggressions, or if you’ve been hearing about the same kind of things from your peers, that sort of thing.

If you glance at me you might not think that I’m in my mid-40’s, so people usually think that I’m in my 30s and say things to me like, “We need to make this easy enough for moms to use. Moms can’t usually figure out something like this.” I’ll let them talk some more about their ideas and then I’ll mention that I’m a mom. Or someone will say, “only young people do this, like you and me” And I’ll ask, “What’s young? I’m in my mid-40’s.” Being tech-savvy or using a lot of tech is not only the domain of people under 35 (any more).

There’s a stereotype of women, of moms and of grandmas, of not being tech-savvy (though most women over 70 are quite tech-savvy). Also there’s an assumption that I often hear, that if you’re over 40 or over 50 then you aren’t a tech native and you probably have a hard time with technology compared with a millennial. I’m not offended. When I hear this (at least once/week) then I point out that I’m one of billions of people in my age group who know how to do a lot more than just turn their phone on and off.

From a high level, how do you feel about the state of tech in 2016? What excites you about the future? What frustrates you and would you like to see change?

I wish someone would solve the video conferencing problem—video conferencing still does not work really well. I want a less bulky Android watch. The new ASUS zenwatch is smaller than the first one but still not slim and streamlined.

I anticipate some general anxiety about the tech industry because I think that we’ve already hit a bubble and we haven’t realized it yet. I fear we may see lots of companies dying and we are already seeing people leaving the city and getting laid off.  I hope this year doesn’t become as bad as I fear.

I’m also curious to see what happens with all of the contract work that people are doing because there aren’t good laws to protect contractors. A lot of tech companies have started up in the last few years that rely on contractors. I don’t know if it will happen this year or next year but it will happen sometime soon; either people will band together and unionize or they’ll start demanding higher wages or demand to be employees, or all of the above.

I believe and hope that automation and assistive robotics will become more integrated into our lives over the next 3-5 years.

“I anticipate some general anxiety about the tech industry because I think that we’ve already hit a bubble and we haven’t realized it yet. I fear we may see lots of companies dying and we are already seeing people leaving the city and getting laid off.  I hope this year doesn’t become as bad as I fear.”

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

Getting to know as many different types of people as possible will help you in any career, but it will particularly help you in tech, because tech is basically a network of people who will keep you and hold on to you if you belong to the group.

As soon as people know who you are—they know what your skills and experience are, they’ve worked with you, they’ve done something with you, they’ve enjoyed conversations with you—they will stick with you. And I think that that isn’t valued enough, and it certainly wasn’t valued by me when I was straight out of college or in my mid-20s. I just thought, “Whatever, I know everything, I can do anything, nobody will ever discriminate against me.”

Now I know it’s imminently important to show up, to get to know lots of different types of people and to be present and to talk and be true to myself. If I show up and I talk and I connect and I listen and I make conversation then I’m a whole person instead of a middle aged woman, a cute woman, a potential date, a young woman, whatever it is that you’re judged/labelled in the first couple seconds you’re seen.

“Now I know it’s imminently important to show up, to get to know lots of different types of people and to be present and to talk and be true to myself. If I show up and I talk and I connect and I listen and I make conversation then I’m a whole person instead of a middle aged woman, a cute woman, a potential date, a young woman, whatever it is that you’re judged/labelled in the first couple seconds you’re seen.”

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.”

Sure, definitely. Well, like you, I took a non-traditional path into tech.

As a child, my father ran a software company, so I was around technology a lot from a young age and really enjoyed it. I hung out at his company a lot. I remember taking a few programming classes in the ’80s – community classes with mostly adults – and it was totally unusual to find a young girl in those kinds of classes. I liked it, but it was just another hobby.

I was progressing through school, I became really interested in science and that turned into an interest in Genomics pretty early. I wanted to be a geneticist, probably a doctor, and that was the plan. So I went to Ohio State, which at the time was one of the best programs for under grads in genetics. That experience got me even more excited. From there, I went into research. My first job was at St. Jude Children’s Research Hospital, the cancer hospital in Memphis, I worked in research for four years, and my plan was to get closer to the work, find out what interested me most and go back to school to get my PhD or my MD and be a research scientist. But when I got into the work, I actually didn’t find it that interesting. I found the subject really interesting, but the day-to-day didn’t stimulate me.

The dot com boom was happening around that time, so Silicon Valley was getting a lot of attention. Programmers and computer scientists were getting a lot of attention. And I remember thinking, “I did that as a kid. It was a lot of fun, and I was good at it.” That seemed like a really exciting career to be in, where there wasn’t this ceiling.

That’s the other thing about research – it doesn’t pay very well, and that really bothered me. I wanted to be in a field where the sky’s the limit, and hearing about all of these entrepreneurs out in Silicon Valley got me really excited.

I didn’t know anyone out there. My exposure was literally from the news. I got really lucky, because this new field was emerging called bioinformatics – basically a merge of biology and computer science. A company called Celera was getting a lot of press because they were sequencing the human genome and racing to make this data available to scientists. It was the Human Genome Project. This project generated an enormous amount of data. This was big data before anyone called it big data, and that data needed to be mined. There was a need for people who could not only understand biology and the data and the science, but also write scripts and programs. That was perfect. I was already thinking about computer science, and now there’s this way I could segue from biology.

I started applying to companies in the Bay Area, Celera in particular. Celera was my target, my dream. I thought that would’ve been the most amazing thing in the world. I applied, I called, I harassed them and applied some more. After a lot of brute-force effort, they hired me, and I relocated from Tennessee to the Bay Area. It was a complete dream job – especially since, by this time, we were in the dot-com bust and not many people were traveling west. I was at Celera for around 4 years working on really interesting and high-profile projects, but I completely fell in love with computer science, so I went back to school in the evenings and got my MS in Computer Science.

Being an engineer in the Valley is a very empowering thing. You identify a problem and write code to solve that problem. It’s very gratifying. I started to become very entrepreneurial. I met my eventual co-founder at Celera, and the time was right for us to dive in head-first and start a company. And the funny thing about it is that we didn’t actually know what we were going to start. It wasn’t like, “I have an idea. I need to go start a company.” It was more, “I need to start a company, and I’ll find the right idea later.” I talk to a lot to entrepreneurs, and they always say, “I don’t know if my idea’s good enough.” And I’m like, “It doesn’t have to be, because you’re going to change your idea 10 times.”

Our first idea that really took off was a company called Spitfire Photo. It was a solution for photographers and, specifically, small, independent agencies around the world that covered global events. We were getting decent traction, but soon realized the market is relatively small and slow growing. We struggled for several years to accelerate it and eventually made the decision to pivot to an enterprise offering after seeing some adoption within organizations. So in 2010, Spitfire Photo became WebDAM. My co-founder and I actually built the first version of the product. There weren’t any other cloud solutions that could do what we doing for enterprises, and it really took off from there. We never raised outside funding, and we were eventually acquired in 2014.

That’s really amazing. So let’s step back. I’d love to hear more about your experience of fundraising and what was disenchanting to you and what fed into that idea of “let’s hold off.”

Right. Well, it was a lot of things. The first investors we approached were definitely top-tier, and we were very early stage and still refining our market fit. There were lots of learnings that came out of those conversations, but it became very clear to us that we should grow the business further before fundraising.

That was one thing, and two – and this is much more clear in hindsight – the Valley was completely male dominated and a very different experience than it is now. Today, being a female in tech is talked about and, as an investor, you have to be aware of the gender disparities and potential biases and operate with a certain level of sensitivity around the topic. But back then? Definitely not.

The other thing about it is – and this is something that I literally just started talking about in the past year, we went 10 years without ever really talked publicly about it – my co-founder is my husband. Early on, when we started the company and people knew we were married, people would say, “Can I talk to your husband?” As if I was his assistant or something! I decided at that point it was not going to define me and became very private about it. Back then, many investors were strongly opposed to investing in married couples.

I can understand that risk, but having a co-founder is like being married. You don’t need a marriage certificate to have disagreements, fights and break-ups – co-founders have fall-out all the time. Interestingly, as more women are jumping into entrepreneurship, we are seeing more and more married co-founders. It’s more accepted. But at the time it was very discouraged, so much so that the second time we started looking for funding I would seek out women investors. That was very unusual for me, because I’ve worked in male-dominated industries my entire life and I’ve never felt like it mattered much. Even when I felt bias, I was like, “Whatever. I’m excited to prove you wrong.” It just never really affected me negatively. But the second time around I said, “I really want to find women investors, because I think they’re going to be more empathetic and open minded.” And in my experience, they were. We were finally well positioned to raise when we started to get approached about acquisition and the conversations changed.

How did your life change as an entrepreneur and the head of a company once kids came into the picture?

I have two kids. My first was born right when we pivoted away from Spitfire Photo to WebDAM. Maternity leave was actually very refreshing. My mind was clearer to think creatively about other options. That’s important for any entrepreneur – to find that space to think clearly. Maternity leave was my space, my time.

I struggled to be a “normal” mom, though. I joined moms groups to meet other new moms and did baby yoga and noon stroller walks. At first it was amazing. It seemed I had a life again. But when it came time for all my “mom friends” to go back to work, I was the only one that did.

Everyone else decided to stay at home, but for me that meant shutting down the business. That was a turning point for me and I started to think differently about how I could combine my loves. Work-life balance wasn’t going to be possible, so I turned to work-life integration. I focused on teaching my son about business and software starting at a young age. I wanted him to know the company, understand it, know what I did, get excited about it, be familiar with it, know who works there. I just wanted it to be part of his life too, because it was clear it was going to be a very important part of our lives.

I have since had a second child, a daughter. And they both walk into WebDAM and know the team by their first names. We have ping pong tables and video games, and they would rather go there than anywhere else after school. Of course, it’s like any other office and we don’t have kids running around during the day, but there are late nights where the kids are having a pizza party while the team is having a hackathon. It has become an important part of their lives, too.

How do you think that experience has shaped your approach to work and your priorities? What about your management style?

It’s tough because I think, for most entrepreneurs, it’s not work. It’s a lifestyle. It’s my hobby, my passion. It’s everything. Even if I wanted to totally separate it or be like, “My kids are going to be my only priority,” it’s still my passion. That was new to me – I didn’t know that about myself. That’s why I think being able to involve them in different ways within the business has become so important.

I actually became much more empathetic to women in the workplace once I was a mom. There was a time when I found it difficult to understand how people could not be 150% invested in their careers – crazy, right? Becoming a mom changed the way I think about other people and how everyone has competing priorities, whatever they are. It’s not my job to judge what should be your priorities, but it is my job to help make it work. That changed a lot for me.

Running a business for 10 years has also increased my awareness and empathy. You come across all sorts of people from all walks of life and start to notice themes. For instance, it became very apparent that women are less inclined to participate in large meetings, always taking a back seat. As a woman CEO, this really bothered me – it’s not like they are the only women in the room? I struggled with confidence myself in the past, but didn’t realize what a systemic problem it was until I managed a large team and saw the staggering differences.

Yeah, and I’m curious to know your thoughts on how do you undo that? When that kind of damage has done over and over and over for so many of these women and other folks who have been in tack and then they come to a company like yours that is better, just because of your experience and you running it, how do you un-train them to actually believe in themself again?

It’s very hard, and I don’t think it’s just from work experience. I think it starts really, really early. At least that was the case for me. Part of the reason it took us five years to pivot was because I had some fundamental confidence issues and an inability to trust my instincts.

Not to be overly optimistic, but I do think it was a bigger issue in my generation, give or take 10 years. I was raised in a society where most moms stayed at home. Our dads were the breadwinners. Men and women held very specific roles. My kid’s generation is seeing a totally different view of women. I’m very hopeful that time will sort out a lot of the unconscious bias. This is why it’s more important than ever for women to ignore the voices of doubt in our heads and forge forward. The next generation is counting on us.

At WebDAM, we started a group called Women of WebDAM (WOW), for exactly this purpose: Come together and support one another. I don’t get a lot of face time with most of the team anymore, and I missed it, so this group provides a way for us to lean on a support network. Sometimes we just go to a wine bar and have wine and talk. Sometimes we’ll do book club, sometimes we’ll go to a networking event or a women’s film festival, whatever it is. But it’s a time for us to get together and have those conversations, and it’s been incredible. Honestly, it’s been as rewarding for me as anyone on the team.

I’m curious: as an entrepreneur, where did you get your resourcefulness from? You jumped from science to computer science to business, and you decided to start your own company and you’re planning to sell to all these clients. What was your process for learning what to do?

Resourcefulness has definitely been a critical skill over the years, as it is for any entrepreneur. I think it comes from a few places. One, I think I am just naturally a problem solver. As a child, the first database I wrote was to categorize my clothing by color and season. It sounds super neurotic now, but it seemed like a totally appropriate thing to do with the Wang business computer my dad brought home from work. I will also say that, even though my parents had traditional gender roles, they were very empowering. There was not a day that went by that I didn’t believe I could do anything I wanted to. And that meant being an astronaut, an actor – the sky was the limit.

My years as a scientist were certainly influential as well. Science teaches you perseverance – digging deeper and deeper into a problem and constantly exploring new untapped avenues.

And last, I have always been relentless in my pursuit of success. I’m not sure where this stemmed from, though I do know that my resourcefulness developed a great deal during the five-year period when we were trying every possible means to accelerate the growth of the business before eventually pivoting.

Where do you see yourself in five or 10 years? Do you think you’ll still be in tech?

No doubt. I love the tech industry. I really love it. I’ll probably either be growing a business or advising and investing in startups. Or perhaps both.

I love hearing other entrepreneur’s stories and being part of a rapidly changing landscape. It’s just a really cool place to be and, being in the Valley, it never gets old and it’s always changing. You’re always meeting someone who is doing something interesting.

Absolutely. Let’s see, if you want to dive into anything else let me know, but my last question to you would be just what major lessons have you learned and what advice would you want to give to aspiring female entrepreneurs?

I think the biggest one that took me a really long time to learn was that nobody knows what you should do. Even if someone has done it before, even if someone has done it over and over again, it doesn’t mean they’re right about what you should do with your company. Trusting our instincts became really important for us. There are so many different ways to achieve your goals in business – ask five people what you should do about a problem in your business and you’ll probably get five different opinions. Every product is different. Every market is different. Economic conditions are constantly changing. So I think it’s important to get really close to your market, really close to whomever your customer is, because that’s when you’re going to be able to develop the instincts and know what to do. You’re the one talking to the customer.