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 was born in Brooklyn, New York to a pretty warm family. They’re predominately blue collar on both sides. My dad was born in Nigeria and lived in Sweden. My mom was born in Trinidad, an island seven miles north of Venezuela. She moved to the States when she was a teenager to continue her education. After college, she settled in Brooklyn, New York where a lot of her family lived. My father-to-be was still a continent away in Scandinavia.

My mom had a good friend who, just like her, loved to travel the world. This friend was doing her master’s in Sweden and invited my mom to visit. On her trip over, she caught a cold but mustered the strength to still go out and do things. Then one day she went to a local church and found herself sneezing a lot. A gentleman sitting behind her kept saying “bless you.” Later that day, the church had choir practice. My mom, an amazing singer, ended up practicing with them. Further into practice, she started singing a song that the “bless you” man started playing the piano along to. She turned around to who would become my dad. Obviously he got her number.

They started dating and, after some time, got married in Sweden. This was 1993. I was born September 14th the following year in Brooklyn, New York. But my dad, in need of a sponsor, wasn’t able to make it to the US in time for my birth. He was distraught. I was cool with it because I was five minutes old. My dad was still finishing up his Master’s/MD program, so the distance from his family definitely affected him. He was finally able to move to the US in 1998. In the four-year period before this, I briefly lived in Trinidad to learn about culture and be near my mother’s family. Then we lived in Sweden to be with my father. “We” was my mom, myself, and my half-brother. We have the same mother and different fathers, but my father was definitely a father to him too. I’m close to my brother. We’re 12 years apart, so growing up wasn’t your typical sibling-relationship, but it worked and still works for us.

“Maybe that’s why computers were so interesting to me. A way to “escape” into a new world, full of possibilities. Where the cure to loneliness was a Cmd+T away.”

Growing up in New York, I was surrounded by South Caribbean culture. Most of my father’s family lived in Maryland, so although I knew and occasionally visited them, I didn’t know their culture too much. However, when it was time for my brother to go to college, my father suggested we move to Baltimore, Maryland. We did, and all of a sudden I was surrounded by African culture. Stark difference.

Baltimore was a major change from Brooklyn. New York is fast-paced. Maryland is not. New York is dense. Maryland isn’t sparse, but it’s not New York level either. And we lived in Baltimore County, not the city. So it was even more laid back than my previous home. People drove more and rode the bus less. The transportation system was complete crap. I got used to all of it though. I also got used to my dad’s family’s culture. My mother has two siblings. My father has six. Four of whom also lived in Baltimore at the time. His family is very close, so I’d see my cousins more than some people saw their siblings. They all felt like brothers and sisters to me, but then I’d have to go home to no kids whereas they had their own siblings. Looking back now, I realize that I often felt alone as a child, yearning for my brother. I’d see him like twice a year when he was doing his Bachelor’s and Master’s, but I got used to it. Maybe that’s why computers were so interesting to me. A way to “escape” into a new world, full of possibilities. Where the cure to loneliness was a Cmd+T away. Still, my family’s culture taught me the value of family. I finished up elementary school in Baltimore, then attended middle and high school. Childhood was fine though. No sleepovers, culture thing. First job was cleaning our church. Oh, and I got a ton of migraines. They’re gone now. Thank God.

I remember in elementary and middle school, I used to talk a lot. I also asked “too many” questions. My parents said it was because I didn’t have a sibling around to play with, so I’d get bored. When I’d finally see another child, it was like a seeing a new species and I’d feel the sudden urge to tell them all the things. Of course this was much to the dismay of teachers, so I’d often find myself in trouble. However, one of my teachers in elementary school didn’t see my talkative nature as being a “disruptive child.” She saw boredom and sought to challenge me. She put me in a program called GT, or Gifted and Talented. It was a track for students who should probably be a grade or two above, but didn’t skip. One year into it, I was still talkative, but it was much more bearable. I also felt challenged. Looking back, I really appreciate what she did for me. Most of my teachers told my parents that I had a learning disability, or that I exhibited traits that often lead to dysfunctional people in society. This teacher just saw me for who I was. A bored child. Thanks, Ms. Gaston.

This was probably the first identification that maybe my skills and interests were not aligned with those of my classmates. I was the “draws all over his homework” kid. Of course, I learned to conform. Just like I had to conform to desks designed for right-handers when I was part of the left-handed club. Then in middle school, my attraction to web went through the roof when I stumbled upon code. I found it so intriguing to be able to do whatever you want and put up whatever you want with no teachers around to strike you seven points. It was ultimate freedom and I wanted it. So I taught myself HTML and CSS, then starting hacking around.

I started doing websites for family, then family friends, and finally strangers. I remember setting up a Paypal account to collect payments. I connected it to my checking account that my mom let me sign up for. It was a branch of Wachovia built for children. I remember taking on some projects that required Flash or some heavy JS. Instead of turning those projects down, I’d say “oh, I can do that!” Then I’ll read up tutorials or would find things around the web I could build off of, like Wix. Ugh, I used to use Wix. I would figure out what the yearly cost was for services like Wix, then would add on a premium to the project total so that I’d collect a profit at the end. It was cool getting those monthly or yearly charges from services I would use for the projects. Sometimes I’d mis-plan and go in the negative, but I was learning. Design and business. After two years of this grind, I was able to save up for my first Macbook. Third-hand off eBay.

Daytime, I was in school. I started identifying the classes that interested me the most. Math, psychology, and English. Math had systems and frameworks. Psychology broke down the way people think. English, had creative writing – freedom of expression. I found it very interesting because it was the one type of assignment where your teacher could only grade you on grammar and spelling. There was no such thing as a bad idea. These things stuck with me, and ultimately influenced my design career.

English class ended up leading to another passion – blogging. I started my first blog over a school summer. It was called mediainfive.com. The goal was to capture the top news of the day and synthesize them into a five minute digest. The site probably got 100 views per month. I’m pretty sure they were my mom and her friends showing me support. I ended up pausing the blog when I returned to school. My second blog was called trendingweb.com. It consisted of interviews I’d conduct with entrepreneurs from around the web who were building cool stuff. Their products often had little-to-no users at the time. Some of these companies turned out to be Zerply and 6Wunderkinder, makers of the todo list app, Wunderlist. These blogs also led to writing opportunities at bigger sites. I did an internship at AppAdvice, a blog that focused on Apple’s iOS store. At the time, it averaged a million views per month, so that was a big change for me.

Writing 5–8 articles a day for them taught me discipline and polish. A lot of the practices I learned there would stick with me down-the-line. Afterwards, I wrote for a blog called Macgasm, also focused on Apple. This site was incredible. It was the first time I “hit” Hacker News, Google News, and broke a site from web traffic. It also led to me visiting San Jose to attend a tech conference, where I got to meet really inspiring people who would become friends in the future. Chris Anderson, the founder of TED, and Mark Johnson, then CEO of Zite, were a couple of them. On my way back from that trip, I remember reaching out to Mark for an interview. I wanted to play around with a new format of recording an interview, transcribing it, then summarizing it into a sort of story with pull-quotes. If you saw my recording setup, you’d laugh. But it was different, and he was down for it. It spawned a series of interviews of a similar fashion that I did for Macgasm, and led to me getting my own column. I met other friends through this column like the Sparrow, Flud, and Instacast founders. Looking back, it was an evolution of TrendingWeb. I’m grateful for having had that experience. And I’m grateful to my parents for letting me pretend to be sick, so I could skip school for a few days for the San Jose trip.

By now I was in high school. I attended Overlea High. It was a big change from my middle school. Parkville Middle was in the top 10 in Maryland. Overlea High was in the bottom 10. Why did I go there? In our school system, each student had zone schools, or schools they’d attend by default based off location. Golden Ring Middle and Overlea High were my zone schools. After elementary school, I applied to Parkville for their magnet program. In it, I got to take interesting courses like Mass Communication, Visual Arts, Environmental Sciences, and Applied Engineering. When high school time came around, I applied and didn’t get into my school of choice, Eastern Technical High. The number one in the state and top 5% in the country. In the future, I learned that some parts of my application were mixed up with another student, costing my acceptance. No one thought to correct it and I ended up at Overlea. Most of my friends went to Eastern, so day one of Overlea was definitely an adjustment. It was pretty bad. First day, there were at least five fights and three suspensions. We even had metal detectors at the school’s front entrance.

“I remember students joking during my first few months that I probably got into numerous fights, or that I was a thug, etc. The theme was that I was lucky for even getting into Eastern, and that I wasn’t going to succeed at the school. I mean, during week one people would literally move out of my way in the hallways.”

But I found the good. Our school had a program called DECA – Distributive Education Clubs of America. It’s very similar to FBLA – Future Business Leaders of America. It was a business club for high school students that had competitions at the county, state, national, and international level. My club-mates and I competed our way to internationals which took place in California. We traveled for the contest, and although we didn’t place at that level, it was an amazing experience. It was a big deal for our school. It was also my first dose of California weather. I knew I’d be back one day.

Halfway through my first year of high school, Eastern Tech announced that they would do something they had never done before – allow students to apply to enroll in 10th grade. My parents were all over this. I applied and got accepted. I later learned that only two students were accepted state-wide. My mom was excited, but I didn’t care anymore. I had gotten used to Overlea, built some friendships, was top of my class, and didn’t mind the fights anymore. My mom wasn’t having it and, come the following August, I was an Eastern Tech student.

Tenth grade. I remember showing up to school on day one. People looked at my funny. Was it because I came from Overlea? Was it because I didn’t look like anyone there? Maybe both. I was coming from a school that had a very negative stereotype. I was entering a school that was probably 75% Caucasian and 2% African-American. I remember students joking during my first few months that I probably got into numerous fights, or that I was a thug, etc. The theme was that I was lucky for even getting into Eastern, and that I wasn’t going to succeed at the school. I mean, during week one people would literally move out of my way in the hallways. Like, did they think I’d shove them or something?

It took about half a year for me to settle in and for the negative sentiment to “settle down.” Like Parkville, Eastern provided magnet courses that students could major in. The options were Health, Automotive Technology, Business Management and Finance, Interactive Media Production, Construction, Culinary, Engineering, IT, Law, and Teaching. I chose IT, the closest I could find to my evening passion of coding. I later learned there was little overlap, but I still learned a lot. By graduation, I was CCNA-certified and could work entry-level for Cisco or the NSA. I didn’t do anything with that certification, but the knowledge was valuable. I remember learning how to make ethernet cables from scratch, and at least retained the knowledge for fixing my wifi when it acts up. However, I realized in 11th grade that although it was interesting, IT was too technical for me. I didn’t want to fix the Internet, I wanted to build awesome things on it.

“Online, I experienced more ageism than racism, primarily because I hid my face for a long time.”

This realization led to me noticing that my true passion lied with websites. How they looked and how they worked. Up until then, I had messed around in Photoshop and tried to design, but I didn’t consider it a skill. So I decided to change that. I started reading blogs like A List Apart and Think Vitamin. Then I’d find designs from around the web that I liked and would try to reverse engineer them in Photoshop. I did 2–3 a night. It didn’t take long for the practices to commit to memory. However, I couldn’t find much content on what it meant to a designer. Or a content that covered the developments of the design industry. Like, what tools were people using nowadays? Or what we could learn from the most recent hot app? I don’t know why I felt like I was the one to do it, but I told myself I’d create a blog for this. I met my blog co-founder, Drew Wilson, on Twitter. A couple months later we started The Industry.

This was November 2011. Our tagline was “covering design-focused startups and people.” In our first month, we had a couple thousand visits. 6 months in, we were averaging one hundred thousand. Drew handled the design, development, and promotion. I handled editorial, and sponsorships. We ended up building an editorial team of 12 people. Our first, and most loyal sponsor, was Squarespace. We started a podcast with Adam Stacoviak, and within months, it had surpassed the blog in popularity. It also represented a majority of our revenue, which I used to pay our editorial team. The team was distributed. None of us met in person until years later, but it was a true passion project. I remember writing, editing, and coordinating with the team in the evenings and weekends, then reviewing articles to publish at school during lunch time. The team is all in great places now. One’s a designer at Microsoft by way of Sunrise, another is just crushing it in New York, another is a writer at Invision, one’s VP of Design at Acorns, etc.

I didn’t know it at the time, but the podcast which we called The Industry Radio Show, would play a huge role for me. Each week, we’d have guests on to chat about design. I’d notice patterns in their background stories, what they did day-to-day, and what they were most passionate about. They were describing my job description. A lightbulb went off in my head. I told myself, “okay, this is the kind of work I want to do. The best of all worlds. Write, design, code.”

“My dad’s an optimist, but it hit him in that moment. Because he knew that something as small as someone just slightly discriminating against you could destroy your life. For him, it was something that could have kept him from his family indefinitely. For me, it was something that could have ended my chance of going to college and put in jail.”

High school was wrapping up soon. I applied to one university in Maryland, and two in Pennsylvania. UMBC, Drexel, and UPenn. I got into them and was now faced with a decision, but I couldn’t shake the feeling that I didn’t need any of them to pursue my newfound job description. I had become jaded to the whole college thing, but didn’t throw it out altogether. I knew it was important to my family, and that I would be judged by my peers if I didn’t go. After all, there was a stereotype. I opted for Drexel with a major in something design-y, and a minor in psychology.

That was the plan. Graduation came. I remember sitting down with my class and facing all the parents, thinking to myself “I wonder how many of them are doing what they love as a career?” Then I looked around to members of my class. Some had huge smiles on their faces, knowing that they got into the school of their choice, their boyfriend was coming with them, and that “everything was going to be awesome.” Some had partial smiles on their face, knowing that they were going to get the education they wanted, but at the cost of their parents savings or theirs. Some, like me, were expressionless. Were we all thinking the same thing? Were we all thinking “is the future really as simple as getting a degree and getting a job? Or must we find our own path?” I don’t know, but I know that’s what I was thinking. In that moment, while our valedictorian spoke, I decided to choose my own path. Step one was finding an alternative to college.

I started thinking about the guests from the podcast again. How did they find their path? I also started weighing the education system against this “choose your own path” model. It leaned heavily to “choose path.” I recalled the feels I’d get when I’d ship a website for someone, or publish an article on the blog. Or the fact that Drew, although years older than me, didn’t care about my age or race. He just appreciated my work. I then thought about school, and some of my teachers dating back to elementary school. My quarrels with how tests were set up for memorization and not comprehension. The racism and stereotype I felt coming from Overlea. And finally, how I nearly lost it all by an ungrounded accusation.

“I know that’s what I was thinking. In that moment, while our valedictorian spoke, I decided to choose my own path. Step one was finding an alternative to college.”

About that accusation. About 1–2 months before graduation, I woke up late for school. The night before was a long one for The Industry. My dad drove me to school. I exited the car, walked into the front office, signed the late slip, then proceeded to my homeroom. In my second class of the day, the assistant principal and another faculty member came into my class and stopped it. They asked me to come to the front office with them. The tone was anger. I was completely puzzled and remember hearing mumbles from students that I was probably in big trouble. But for what? We finally got to the assistant principal’s office and the other faculty member said in a demoralizing and assertive voice, “We were informed this morning that you have been dealing marijuana around school and that you came in this morning smelling like it.” I was shocked. I asked where they got that information from and they said they couldn’t reveal that information. I then told them to check their cameras outside and at the front-desk. “My dad drove me to school. You have a camera outside looking at everyone who walks in. If you check that camera and check the timestamp, you’ll realize that 15 seconds later I was in the front office, which also has a camera. You’ll see that I signed in and left for my homeroom. You can then talk to my substitute homeroom teacher and ask when I got in. And then you’ll know that there was no way I could possibly have done anything in between that time.”

As I was saying this, it hit me who made the accusation. My substitute homeroom teacher. When you get to school late, they’re the first person you go to before heading to your class. That day, I went from my homeroom teacher to the class I was pulled out from. It had to be her, so I asked. They froze. Without speaking, they had answered. At this point I was just trying to keep my cool. I started smelling myself out of curiosity. I wasn’t sweating or anything, and I showered that morning. I smelled normal. So I asked them to smell me. One of them asked, “what?” “Well you said that a teacher said I smelled like weed. You just pulled me out of a class. I’ve only been in school for 30 minutes. I haven’t changed my clothes. Smell me and tell me if I smell like weed.” The assistant principal did. So they leaned in and said, “Yeah, I don’t smell anything.” By this point, logic had won. I had also proven a point. Before doing the simple act of following up with the teacher, or checking the cameras, they were convinced. That was wrong. Not to mention, they threatened that I could lose my college acceptances, scholarships, and that I could be arrested right then and there by the police officer standing outside.

Even though logic had won, there was something painful in the back of my mind that I learned growing up. By being black, I was at a disadvantage by default. So when faced with such situations, I had to keep my composure and let nothing else show but my logic and reasoning. Somehow it worked. The faculty guy said I could go back to class and that they’ll talk to whomever to get to the bottom of the situation. I nodded, but before getting up I noticed something outside the front office. It was a wall of the names of students who got higher than a 2,000 on the SAT. For the mic drop, I turned and said “by the way, I notice that my name is missing from that wall. So after you get to the bottom of this, do you think I can be added?” Then left. The rest of that day was draining. I couldn’t think, eat, or talk. I went home looking like a zombie. It didn’t really hit me until I got home. I started breaking down. Why the hell was this happening to me? And so close to graduation? Could I really have lost everything in that moment? What would have happened it I didn’t react the way I did? I was afraid to tell my parents, but finally mustered it right before going to bed. They were in pain after hearing it. It reminded my parents of something that happened to my dad in Sweden that nearly put him away for a long time. Something he didn’t do, but was accused of doing because he “looked like someone who would do it.” Sad part? The thing he was accused never even occurred. By anyone. Now his son was experiencing something similar.

Holy shit.

My dad’s an optimist, but it hit him in that moment. Because he knew that something as small as someone just discriminating against you could destroy your life. For him, it was something that could have kept him from his family indefinitely. For me, it was something that could have ended my chance of going to college and put in jail.

Wow.

Needless to say, that dampened things for me. After he was told, my brother took a train from DC to Baltimore with the intention of going into my school. I wasn’t looking forward to it. I didn’t want to be “that kid.” The one who doesn’t let things die, but drags them out after a resolution had been reached. But my brother made a valid point. “It’s not a matter of settling things. They need to understand; one, what they did; two, why it’s wrong; and three, to never do it again to any student, right.” I felt confident that he’d handle the situation well. If you think I’m articulate, just meet my brother. He doesn’t lose. He didn’t. I don’t know what he said to them, but the same teachers who pulled me out of class showed up to every one of my classes that day to deliver the same message. As if from a script, “Hi. We just want to come by and let all of you know that yesterday we pulled Jared out of the classroom because he was suspected of an act. We know some rumors have spread around the class. Rumors are detrimental to students. They can hurt your reputation. We want to clarify that Jared did not do anything. He’s fine. He has not done anything wrong. We will not tolerate rumor and gossip.” I felt so warm inside. My family had my back. My brother had my front. Being his younger sibling, he felt the need to protect me at all costs. Especially from something he knew was real and out there. Obviously, students still gossiped, and to some I remained “guilty” through to graduation.

So that evening, the evening after graduation, I pondered on the podcast. I knew what I wanted. I remembered an episode with a designer who was also an advisor to a company called Treehouse. I loved Treehouse. I remembered Carsonified, the company it came out from. I use to read a blog they published called Think Vitamin. I was intrigued by Treehouse’s mission, so I reached out to its founder, Ryan Carson. I told him what got me excited every morning, what got me excited about Treehouse, and how I felt I could contribute. After a series of interviews, I got the job! I came on as editor of Treehouse Blog, a spinoff of Think Vitamin. It was a dream come true. To help shape the presence of a blog that came from something that inspired me just a couple years prior. Of course I still did The Industry nights and weekends, but we discussed and agreed on a way that the sites would not compete with each other. Our tone, content, and audiences were different.

My job involved helping on building an architecture for what would become their blog, newsletter, and marketing. It was my first time working with product designers. They were my favorite. A month or so into the job, the remote Treehouse employees were flown into Orlando for our team get-together. It was an amazing feeling seeing other people who were all part of the team, building towards the same vision. However, by the end of it reality started settling in that maybe I might still have to go to college. Although I wasn’t the most passionate about it, my parents still expected it. I remember having a conversation with Ryan telling him the possibility. At first, he was caught of guard. And of course he was. After all, part of the mission of Treehouse was to provide the education I was passionate about, so that people of all ages didn’t have to spend tens of thousands acquiring the skills. Especially if the curriculums had a high chance of being out of date. But he understood where I was coming from. Ultimately I left Treehouse after about four months, but it was an incredible summer full of lessons and confidence boosters that I wouldn’t be aware of until months later.

I met up with two guys on the Internet. Both were from Kansas, but none of us had ever met in person. We all shared a passion for emails. I became fascinated by it when I interviewed the Sparrow founders a year earlier for the Macgasm column. We also shared a passion for the potential use of iPads in the workplace. We were like, “let’s start a company.” We called it Evomail. Evolved email. In hindsight, bad name. Sounds like evil mail. We really had to enunciate the “vo” or people would look at us awkwardly. I’d like to say that we were on to something. Some of the things we built are now in products like Inbox, Outlook, and other apps. Didn’t come directly from us, but patterns make their way around eventually. Some of the things I’ve yet to see in a product. One of the things we wanted to do, was to recognize if an email came from a person, or a service. If it came from a service, was it informative or a subscription? If it was informative, could we treat it like a notification? Imagine if you got an email from UPS, that should not take up the same cognitive space as an email from a close friend.

Evomail was going well. We knew what we wanted to build and we were building it. It was an amazing experience cutting new builds everyday, and putting them in my parents hands. Although they didn’t exactly know what was going on, the builds were enough to show them that I had found my passion. Communication. Communication by words, process, and pixels. It also bought me some time off of college. I negotiated my parents into letting me take my first year off of college to work on Evomail and The Industry. On my 18th birthday, I decided to write a blog post on the blog. The target was other creatives in my age group. Those who had a burning flame of passion inside them that they were constantly afraid would be blown out. Blown out for age, race, gender, and what have you. I wanted to address the age piece, so I spent my entire birthday drafting a 6,000 word biography of my journey to finding my passion. With an undertone of “keep at it, friend.” Somehow it blew up! I woke up to it being #2 on Hacker News and the most read article on our blog! I started getting comments from others saying “I’m 17 and I love blank!” “I’m 19 and I do blank!” It was an age-coming out party, and everyone was loving it, or so I thought.

Although he never said it directly, I sensed a perspective change from one of my co-founders. It’s as if I went from being an equal to being an intern. It was ironic. I “revealed” my age for the first time because I was finally confident. And apparently lots of people were hiding it for the same reason. But who knew that my decision would hurt me in my own company?

The following January, Mailbox announced their app with an awesome product video. In one of their initial press articles, a reviewer mentioned that a big problem for the app might be their lack of labels. I felt otherwise. So I wrote an article on my blog expressing that although they were competition, I felt that they were approaching the inbox from an interesting perspective. And that I looked forward to the hustle. Without intention, the article made its way around and ended up as something Mailbox would reference on Twitter when asked by people why they didn’t support typical labels. Felt like good karma. The CEO then reached out a few weeks or so later. He mentioned the article and Evomail, having seen some of the design on Dribbble. Although nothing was said directly, he seemed interested in what we were building. Especially why we started with the iPad. I remember telling my co-founders this–expecting a positive response. Instead, the CEO reacted a bit displeased. As if I had done something wrong by it being me who interacted with Mailbox and not him. A month or so later, Mailbox was acquired by Dropbox.

“Although he never said it directly, I sensed a perspective change from one of my co-founders. It’s as if I went from being an equal to being an intern. It was ironic. I “revealed” my age for the first time because I was finally confident. And apparently lots of people were hiding it for the same reason. But who knew that my decision would hurt me in my own company?”

Around this time, I learned about a program in San Francisco called Bridge. It was a 3-month program targeted at Product Designers who wanted a dose of Silicon Valley. I was intrigued. After weeks of negotiation, I convinced my parents. The deal was “3 months in California, then you come back to start college.” Come April 2013, I moved out to San Francisco. By this point, the collaboration at Evomail had significantly broken down. We were all working hard, but not as a team. I still felt the same vibes from the “birthday article,” and other events occurred that just amplified the feels. Around three weeks into San Francisco, I got a phone call. It was my co-founder. We talked about ways for me to push the Evomail brand now that I was in San Francisco, but then the conversation started to changing to “so what if you move into more of an ambassador role?” Of course this seemed completely weird to me. Every founder is an ambassador of his or her product. We agreed that there was no need for a “role change.” A month later, I got another call. I was getting kicked out of my own company. My stake was depleted, and I was left with nothing. The product launched a few weeks later with mixed-to-positive tech press. I received no credit for my work, but I didn’t care. What pained me the most was that the product I had invested the last 10 months of my life into, deferred college for, didn’t take a paying job for, was gone. Just like that. I felt like I had lost a child. I felt so sick for the next three months. I won’t go into details, but trust me. It was not fair, it was cold, and it came back to bite the company. I learned so much from Evomail. It was the first digital product I designed from scratch. It was my first startup. It was my first termination. It was my first sense of purpose. It was my biggest sense of defeat. God, it hurt, but looking back I loved that I went through all of that. Of course, that’s how I felt in the moment. It made me feel my age and race again. How many other people would do this to me in the future? I started dressing older, forcing myself to talk deeper, and prioritizing phone calls over in-person meets.

A few weeks later, I got a call from a big tech company, public, voicing interest in Evomail. This company would have made me a millionaire… before taxes [laughs]. Although I told them that I was no longer financially invested in the company, they pushed for a conversation. They were kind of like, we still actually want this thing, so we can either hire you for our mail team, or you can reach out to your ex-founders and push for a deal… getting your stock back in the deal. I remember having to deal with that. I sought advice from close friends and my parents. The feedback I heard was either, “I don’t know what to do. It sucks to be in that position.” Or, “don’t take it.” I didn’t take it. I told the person I was in contact with that I would be passing altogether. And that if they still wanted the product, to reach out to the remaining team. I didn’t tell the team because communication had ended between us. However, I did end up making peace with the other founder, not the CEO, a year later when he visited San Francisco. I never really had issues with him. He was just too on the fence. There are certain things you’re just not on the fence about. I feel like he – and he kind of admitted this a little – just didn’t speak up. Apparently, after I was kicked out, a few months later, the CEO tried to remove him too.

“I started dressing older, forcing myself to talk deeper, and prioritizing phone calls over in-person meets.”

But the “fear your age and race” thing started to creep back up again. Was this graduation all over again? Thankfully, I didn’t experience it much at my first job in the city, Omada Health. I was hired as their first full-time product designer. I remember having a good experience there, but I did feel treated like a child at times. Especially by co-workers who had children. Some with children around my age. To some of them, I could be their child, which is true. But, I’m not. I’m your co-worker at a company that we both work for. Don’t treat me like I’m your child. People asked why I left after six months. Part of it was that I worked on an interesting project, finished it, and felt good about it.

I was only really supposed to be there for three months anyway. My parents wanted me back for college. I stayed on longer because the project was fascinating. Building a product that allowed pre-Type II Diabetic people take back control of their health. My project was over, and I felt like I had gotten a good dose of the medical field. Most of my father’s family is in it, so my tolerance was only so high [laughter]. But part of it was that I didn’t like feeling like a child amongst adults. It wasn’t that I wanted to be treated like a boss. I just wanted to do good work and be respected by my peers. I felt like I was doing one, but only getting half of the other. I still appreciated my time there and the people I had an opportunity of working with. They gave me a beautiful send off. I left the day before my 19th birthday.

My plan was to take a break, but that lasted all of one week. I joined Obvious Corp, the organization behind Branch, Medium, and Lift. Lift, the habit tracking app. I worked on that. It was great. I worked on the 2.0. I was only there for less than a year though. My parents, coming from a different generation, felt that four jobs in two years seemed weird. They wanted to know if I had a plan, or if I should just move back east and go to school. “I promise you. I’m not fickle. I have a vision, and I’m making mistakes along the way. But these mistakes are lessons and I’ll figure it out in the end. I learned, four times.” I told them that my plan was to contract, build work and social credibility, and when I’m ready, to find a role where I will be respected and do good work. They agreed.

I did some contracts. One was Nuzzel, a news app. Another was Bloomthat, an on-demand flowers product. I did some other niche products too. It was really fun! I got to work on Bulan Project, something by my friend Elle Luna, with other friends of mine. Those were creatively liberating and fun. Then a really close friend of mine reached out and was like, “Hey man, if I told you there was a company that I would join, would you join?” And I’m like, “Yeah, if such a company existed.” Background on this dude. He does not full time. Period. So I asked him why he wasn’t there already. “Well, I just finished YC, I have a company, I’m about to have a child, and we’re thinking of moving to Hawaii.” Fair. So I said intro away. He introduced me to a company called Teespring. I met their co-founder, Walker. Within minutes of talking to him, I knew he hired talent and only talent. He didn’t care who you were, what your background was, your race, age, or gender. He just cared if you could do good, passionate work. I never left a meeting so passionate about a company or so trusting of its leadership. I joined a month later as Creative Director. 

The first thing I did was redesign the logo. Second was build the team to five product designers and one brand designer. By the end of 2014, I was designing and managing a team at the same time. I had to learn fast. With time I found myself less and less in Photoshop or Sketch, but in meetings working to figure out the direction of a business that, between joining and leaving, had 20x. The growth was fun to watch. We went from 30 people to 300+. But with the growth of the team and product, I had to juggle managing a team and still designing. It wasn’t easy, but I developed invaluable muscles from the grind. The lessons were numerous. From what it means to grow a team, to growing yourself, which is just as important. If not more. My time at Teespring was similar to Omada Health. Great product, culture, and growth. But people are people, and everywhere you go, you’ll meet some who are partially blinded by attributes that don’t pertain to your output. After a year and a half, I left to take a break and detox from the grind. I intentionally didn’t have a plan.

“But people are people, and everywhere you go, you’ll meet some who are partially blinded by attributes that don’t pertain to your output.”

I took about two weeks to do nothing. I read, called my parents more, caught up on some shows, and took more walks. Greylock and Fuel Capital became my home. I started working out of one, and contracting for the other’s portfolio companies. It was fun getting to work with founders again on very early product. I took up one more advisory position. One of my contracts, Copper, really intrigued me. I was introduced to its founder, Doug, by Fuel Capital months before. He was on an ambitious agenda to “kill passwords for people.” We built a close working relationship over the next few months, and he finally asked me to come on board full-time. I pondered over it for a while. I wasn’t planning to go all in that soon. I sought advice from some mentors of mine. I was torn between ramping up my contracting and possibly starting an agency, going in-house at a VC firm, or going all in with Copper. A friend of mine, Daniel Burka, made it all so clear. He asked me what I longed for the most. I said I wanted to make real impact again. I wanted to ship an idea to the world. I wanted to take a huge bet on something so ambitious, it was “destined” to fail. I realized I was describing Copper. Agency and VC life could wait a few years. So I joined. Now it’s three of us. We are trying to replace passwords. I think we have a fair shot. Keep an eye out in the coming months.

And that’s 1994 to 2016. Online I experienced more ageism than racism, primarily because I hid my face for a long time. On Twitter, my last name is Nigerian, but you can’t tell. And when I say, “hid my face,” I mean it. My avatar has evolved over the years. It stared as a silhouette, then evolved to a half-shot of the side of my face, to the entire side of my face, to my face. I’d like to think that it mirrored my evolution of my self-identity. I’ve always been self-aware, but now I know myself too. I know my strengths, my weaknesses, and my faults. I know where I’ve come from, and I have a plan for where I’m going. I’ll be dammed if I let people kill my vibe because I look a little different to them. I could care less.

“Online I experienced more ageism than racism, primarily because I hid my face for a long time. On Twitter, my last name is Nigerian, but you can’t tell. And when I say, “hid my face,” I mean it. My avatar has evolved over the years. It stared as a silhouette, then evolved to a half-shot of the side of my face, to the entire side of my face, to my face. I’d like to think that it mirrored my evolution of my self-identity.”

I still experience the “symptoms” of being black in a predominantly white city. Walking down a street, it’s not uncommon to see a woman pull her purse a little closer in, or cross the street before we cross paths. It’s not strange to notice an Uber driver eyeing me through the rear-view mirror. On buses, it’s not weird to see someone stand instead of sitting in the only empty seat that’s next to me. I’ve sadly desensitized myself to these micro-interactions over the years. So that’s why when people ask if I experience racism, I don’t immediately recall these interactions to memory. For me, racism and ageism had to smack me in my face to get a reaction, and everything else was just “how life is.”

But I don’t want the people I work with to ever feel this way. Copper understands this. Yes, it’s only three of us right now, but it’s already part of our identity. We want diversity of people, backgrounds, and thinking. Not to meet quotas, or to look good in Medium articles, but because it’s critical to a company. And because we care. Why would you only want one point of view?

All right. Okay, four main questions I want to dig into. You’ve touched on this, but what do you look for in a job now? What is important to you in your job now vs in the beginning?

One – companies that understand the roles they’re hiring for and how those roles may bleed into others. When you start a company, especially in Silicon Valley, there are things you just do—like setup Heroku, use Stripe for payments, and AWS for file storage. Then when it gets to people, you’re like, “Okay. I need a technical co-founder. I need two engineers. I’m going to contract some designer. At some point, I’m gonna need someone in customer service.” Instead of asking yourself, “What in particular, do I need for my business?” It may not be the same as the company across the street from you. Maybe your co-founder should have a background in customer experience because of the type of product you’re building. Such people don’t hire because a blog told them to. I think there’s a strong correlation between people who hire without understanding the roles they’re filling, and the people they hired leaving. If you don’t know, find out. Your hire will appreciate it. It sets up accurate and attainable exceptions. Alignment is good.

Two – empathy. People who understand that people are people. When you hire someone, you are entering a relationship. There’s this understanding when it comes to co-founders that you’re finding your partner. You’re marrying this person for the next 5+ years. I think the same applies to employees. They’re not just headcount, they’re people, family. The marriage and family correlation is interesting because it also implies that you’re no longer just thinking about yourself. You think about them and their needs. You try to uncover their problems, blockers, and fears. Then you try, to the best of your ability, to mitigate them. This is empathy. Companies that understand this are in a much better position than those that don’t. Their employees feel valued and empowered to do good and to do more.

Three – a plan, or at least a shadow of one. Yes, the future is the future, but if you’re just shooting in the dark believing you’ll eventually hit something, I’ll pass. I’m also curious to see how much of a plan a company is willing to reveal to me. Little reveal is a red flag. This also includes mission. I’ve got to be excited about what we’re working towards, or else what’s the point?

Four – the people. Are we compatible? Sometimes we’re not, and that’s okay. Just so the non-compatibility isn’t a result of you being assholes. That’s not okay.

How do you feel like your background: where you’re from, the places that you’ve lived, your family, the culmination of that and your life experiences, how do you think that that has made you a better designer and even manager?

My dad’s culture is proud, but they are very hard-working people. Recently, a colleague of mine traveled to Nigeria for a project. She came back enlightened. Going, she knew about 419, something that’s synonymous with Nigerians. But she was surprised to learn that 419 represented probably half a percent of the Nigerian population. Yet somehow, it’s something the entire nation is stigmatized for. Being half Nigerian and working in tech, I remember sometimes being wary about revealing that detail. It was the fear of “he got in?” Or “you’re contracting him? He’s 419, man! You can’t trust those people!” Interesting, that never even crossed my mind, until this moment.

They are so proud and so hard-working because they have to fight that stigma every day. That they’re not corrupt people, but that they are people just like anyone else. But also people who have to work a lot harder than their peer to fight a stigma that pertains to such a small percentage of their people. This impacted me in two ways. It taught me to work hard and be proud of my work. Looking at my family, it always impresses me how much harder they had to fight to get to where they were. And as for pride, it was less ego and more knowing when you did good work, then defending it. I’m not the person to defend disproved work, but I am the person to defend good work. My work, my team’s work, etc. Especially when “good” could be backed up with data. Quantitative or qualitative. I’m the person who says “I will go to war with you. It’s not that I’m right, but that this is right. So if you want to fight me, that’s completely fine. But don’t fight something that is actually going to benefit the company or product.” That’s my family’s type of “proud.”

“Being half Nigerian and working in tech, I remember sometimes being wary about revealing that detail. It was the fear of he got in?’ Or ‘you’re contracting him He’s 419, man! You can’t trust those people!”

On my mother’s side, I learned empathy and the power of giving. If you needed $700 and my mom had $699, she would transfer a dollar from her savings and wire you the $700. I’ve done that before. I remember in my first months in San Francisco, a friend was in need of $500 and I had $510. I just sent it. I stretched that $10 a week until payday that Friday. To stretch $10 for a week in San Francisco is hard [chuckles]. Not easy, we’re talking buying a pack of Top Ramen, and breaking the squares into halves to double it. Then trying to get the water to ramen ration just right so it doesn’t taste like flavored hot water, but “soup.” Nowadays I mentor when I can. Andreessen Horowitz does this program where they pair professionals with college students interested in the same line of work. Its a great way to give back. To impart some of the things I’ve learned over the years, in hopes of having that student replicate my successes and avoid my failures. I try to respond to every email I get. If that person took the time to message me directly, it’s only fair I take the time to respond. We’ll see how far that scales though [chuckles]. Inboxes are dangerous. And I still relearn these traits, empathy and giving, everyday from my girlfriend. She’s the most caring person I know outside of my parents. I love her for this. It’s funny, she’s probably the true designer in our relationship.

Empathy is the number one thing for a designer. By definition our job is to remove friction for our customers so the best way to do that is to, in a sense, become the customer and go through your own product. I remember when there was this big renaissance of design thinking a some years back where everyone started saying, “designers, talk to customers!” It’s funny to me, because that sort of thinking should have never been forgotten. If you’re not talking to your customers, what kind of empathy are you employing?

Being exposed to different cultures at a young age also impacted me. Seeing different cultures quickly taught me the power of diversity. The thing about being a minority is, if you grow up in an area where you are the majority, your tendency is to stay there because it’s the one place you feel at home. If you look at areas in the US where African-Americans are dominant, you’ll notice that most don’t leave. And why would they? Most of them are taught from young that the world sees them as second-class citizens. That they are at a disadvantage by default. So that it would in their best interest to “settle in and call this home.” The Brooklyn neighborhood I was born in was such a neighborhood. My neighbors are all still there. Same street, same home, same floor. But I was forced out of that reality from a young age. Now, as a designer, I seek diversity to supercharge my solutions.

Okay, macro now. How do you feel about the state of tech in 2016, like what excites you, what frustrates you?

I’m excited about the evolution of interfaces. Messaging is becoming a new interface, but I doubt it’s going to be the only one. And it’s not going to be that simple. That tends to be the case in tech anyway. We jump into new territory, explore, identify the patterns that emerge, and then turn them into new platforms. For example, I don’t think Slack is the future; I think the essence of Slack is part of the future. I’m excited for these new platforms. They reduce the cost to start something new, and they expand your reach.

Copper, I hope, will one day be such a platform. Every company is trying to build their identification layer. It’s time consuming. We want to eliminate that overhead for them. Then you have companies like Uber and Airbnb where there’s so much contingent upon you knowing that the people on your services are real and trustworthy that they have to invest millions into their systems. Why couldn’t we solve that for them and their customers? Imagine if you just walk up to any service or any door; there’s one simple protocol by which to identify yourself and it’s free to you, convenient, and secure. More businesses are coming up like that. We’re doing it for passwords and identification but there are people doing it for all sorts of stuff. I’m really excited about that.

“I’d like to believe that the companies that rise up from this correction will be stronger in the longterm because they had to work a little harder to raise, make a profit, make an impact, and make a return. It kind of parallels my life.”

I’m also excited for the correction that’s going on in the tech sector right now. People are calling it a bubble; I don’t think it’s a bubble. Let’s use balloon as a metaphor. What happened in the Dot Com era was like someone who blew a balloon too big and it just popped. Then a few years ago when we had another correction, that was like someone who blew a balloon kinda big and someone else poked it with a needle before it popped on its own. I think what’s going on now is like someone blowing a balloon and someone else saying, “ah, I’ve seen this shit before,” then just squeezing the air right out of it; so there’s no pop. Just deflation. That’s our current correction. I’d like to believe that the companies that rise up from this correction will be stronger in the longterm because they had to work a little harder to raise, make a profit, make an impact, and make a return. It kind of parallels my life.

True.

One thing I’d like to see change is our transparency as an industry. When I started out, we were very open with each other. Especially the design community. I attribute that openness to us being able to “level up” in the eyes of businesses so quickly. Or what others call our “seat at the table.” However, in the past year or two, we’ve become more secretive. We’ve switched out that open collaborative-ness for bickering and petty bantering. We talk just as much, if not more via mediums like Medium. But I fear we’re moving forward, slower. Nowadays, the people who are the most transparent with me are my closest friends, and even with them there’s still a filter.

I understand confidentiality and competitiveness, but the opaqueness leads to slower progression as a community due to a lack of knowledge sharing. We’re more on the sharing of Sketch tips than topics we’re all thinking about, but avoiding. Things like diversity at work, women in tech, and processes to advance the sector as a whole, not just our immediate companies. I don’t know how we get back to the good ol’ days. I don’t know, maybe it’s just nostalgia. Maybe it’s just me. But we’ve been thinking about this a lot at The Industry. We’re building a resource for the design community to help. It’s called Playbook and I hope to put it live in the next few months.

One of the biggest things that hurts a business or people is miscommunication. What causes miscommunication is people not being transparent or clear. And I think that good communication unearths topics that need to be discussed. I’m rooting for Techies Project, Helena.

My last question would be, based on the lessons that you’ve learned over time, what advice would you have for other young designers who are hoping to get in tech or are in tech, and are feeling some of the same challenges that you faced?

Let me break the fourth wall here. If you have impostor syndrome, don’t feel like you’re all alone. Everyone has imposter syndrome about something. Anyone who says otherwise is either a narcissist or just lying. Impostor syndrome is different for everyone. For some, it’s weight. For some, it’s height. For some, it’s accent. For some, it’s hairiness. For some, it’s not having a college degree. For others, it’s having a college degree. For me, it’s age and race. I don’t think that will ever change. But the point is to know this. It introduces you to empathy. Just as how you want people to be empathetic to your insecurities, be empathetic to theirs.

Another thing – if you work somewhere that’s eating you from the inside-out, leave. It’s not worth it. I know other industries say to stay for ten years, but you’re in an industry that’s barely 30 years old. We’re blessed in the sense that we can leave a company after a year, and get a job the next day. Most people leave, because they got a new job. We’re one of the few communities where, when you hear someone say, “I quit,” you say, “Congratulations.” In any other industry, it’s like, “Oh, shit, what are you going to do now? That sucks. Do you need a place to stay?” Of course, if you think you can change your situation, persevere and sort it out. Don’t just bounce. But when you can’t deal with it anymore, kill it, before it kills you. If you’re in an industry that you love, don’t let anyone drive you away from it. You’re a techie, stand tall.

“If you’re in an industry that you love, don’t let anyone drive you away from it. You’re a techie, stand tall.”

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.”

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

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

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

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

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

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

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

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

How was your experience as a female entrepreneur?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

We can talk about that.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Hugely.

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

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

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

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

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

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

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

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

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

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

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

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

I grew up in a multicultural working class community, consisting mostly of immigrant families, right outside of Boston, Massachusetts. It wasn’t the safest or nicest neighborhood, but for my parents it was a step up from the situation back home on the Cape Verde Islands.

“I love it when people tell me I can’t do something and then proving them wrong. I get a kick out of that.”


After the birth of my youngest brother, my mother made two key decisions that would significantly impact our lives and futures. First, she decided to move her family from a troubled neighborhood in Boston to a much safer community. And second; she sent us to a private Catholic school in said community. These events limited our exposure to drugs and gang violence, and got us access to quality education.

My high school was funded by the Bill & Melinda Gates Foundation to supports its innovative model where students would attend regular classes for four days. The fifth day was reserved for a full time job shared amongst five students. We learned valuable, real life skills and could put away the earnings towards our tuition. This is where I was exposed to technology for the first time. I worked with engineers and was quickly captivated by all its potential.

“One of my biggest insecurities is language. English is not my first language, and because of that, I don’t feel like I have the vocabulary to be as persuasive as I’d like to be. Immigrant parents combined with marginalized, low-quality education doesn’t really build a ton self-confidence.
”

Despite the proximity of universities like Harvard, MIT, and Tufts to my home, I never really thought about college until my cousin invited me to spend a weekend with her at Boston College. That experience was transformative for me because suddenly college felt like an obtainable goal. If my cousin could make it, so could I.

My college experience was, like it is for many people who look like me, very challenging. I had to balance lectures and exams with jobs, but that’s how I ended up working for Karmaloop. And at Karmaloop I got exposed to design, art, streetwear brands, marketing – brands like Supreme and Married to the Mob – all of which had strong foundations in graphic design. After I got my degree in neuroscience, I decided to do something for myself. I bought a one way ticket to San Francisco and left everything behind. In San Francisco I found design, technology, art, and myself.

For the first three years I worked as a user research lead for a startup that allowed me to travel all over the world. I got exposed to the long hours and high pressure of tech, but was able to tap deeply into my passion for design.

I worked in tech as interaction designer for a few years now. Those years gave me enough insights into the treatment of women. But one of my biggest issues with the whole diversity conversation is that is it’s often too much conversation. As a designer, I wanted to build and test something that could actually be shipped.

“I fondly remember Ben Horowitz telling me, ‘There’s offense, and there’s defense. And what you’re telling me right now is that you’re taking people of color, who are naturally creative. People of color invented hip-hop, jazz, blues, and rock ‘n’ roll, and you’re putting them in an arena where they’re positioned to win. I think it’s a great idea. Let’s go tell Kanye about it.'”

I quit my job in early 2015 and founded Front & Center. I wanted to expose creative young adults from underrepresented communities to non-engineering roles in tech. I researched and worked with design leaders from Facebook, Google, KPCB, Vice and many others to define a basic set of required skills for product designers that don’t pursue a traditional academic path. That research resulted in a design training program consisting of basic design, communication and presentation skills. Today, I mostly mentor through Front & Center, consult as a designer.



What has your experience been building Front & Center?

I’m very lucky because my partner has been an entrepreneur for years; he helped me out by coaching me on how to avoid typical first time founder mistakes. But even with his help, there is a lot of falling on my face. I saw a problem, but had no solution. So I started building what I thought was right, but while speaking with investors I figured out it’s very hard to find a model for something that usually fits within the non-profit mold. So I had to do a lot of catching up on how to run an actual business, so I wouldn’t look like a fool. And one of my biggest insecurities is language. English is not my first language, and because of that, I don’t feel like I have the vocabulary to be as persuasive as I’d like to be. Immigrant parents combined with marginalized, low-quality education doesn’t really build a ton self-confidence.


“You know when they say, ‘just fake it till you make it,’ right? Well–it’s super hard for me to fake anything because I have no reference points. Getting help from someone that’s gone through similar hurdles is practically impossible because there are very few people who look like me that do what I do. Finding people you can look up to and model your progress after is so important to individual development. Even today I struggle to find role models. There are very few successful black women who made it as designers.”

I’ve been able to expand my network with some amazing people. I fondly remember Ben Horowitz telling me, “There’s offense, and there’s defense. And what you’re telling me right now is that you’re taking people of color, who are naturally creative. People of color invented hip-hop, jazz, blues, and rock ‘n’ roll, and you’re putting them in an arena where they’re positioned to win. I think it’s a great idea. Let’s go tell Kanye about it.” Now these kinds of things happen in Silicon Valley, but all I could think of was “Oh my god, I get to meet Kanye West.” Moments like these don’t come often when you’re a founder. They definitely don’t come when you’re a founder from a marginalized community. But moments like these keep you going, wherever you’re from as a founder.

Tell me more about just the struggles you’ve overall had in your time of tech. What are the roadblocks you’ve had to overcome?

You know when they say, “just fake it till you make it”, right? Well – it’s super hard for me to fake anything because I have no reference points. Getting help from someone that’s gone through similar hurdles is practically impossible because there are very few people who look like me that do what I do. Finding people you can look up to and model your progress after is so important to individual development. Even today I struggle to find role models. There are very few successful black women who made it as designers. So you have to look beyond your appearance, One person that has inspired my way of thinking about the world is Elle Luna. She’s a person that lives her truth, and I’m thankful to have learned that it’s enough to be inspired. Having role models that look like you is great. But when there aren’t any out there, you need to learn to look up to individuals that don’t necessarily look like you.


I can’t stress enough how important role models are. And I want to be that role model for the community that I’m from. When I hear celebrities say, “I’m not a role model, I’m an artist, I can do whatever I want”, I say no: You’re one of the few that made it out. You can show others how to do that. Passing on information is so important to break the cycles of division and separation. I’m in a unique position to set the example for future generations.   


I’ve been thinking a lot about tech-debt in communities of color lately. Access to technology in communities like the one I’m from is incomparable to the access to technology that most people who become successful in Silicon Valley have. Most Black schools have pretty abysmal computer science labs. Students don’t have computers at home, let alone an internet connection. So next to figuring out what stock options mean, a lot of people who are trying to break into technology need to catch up on people who’ve been exposed to tech for much, much longer. I had the privilege to get my first personal computer when I was 14 years old. And I didn’t really know what code was until I was 19. But most of my peers in tech have had access to technology for all their lives, and role models that encouraged them to explore. For people who come from communities like mine, a career in tech is like a pipe dream. There is nobody around you who’s made it in tech, and no parents of family members who can tell you about the career opportunities. Sure, leadership skills come somewhat naturally, but communication can be a challenge when you haven’t been exposed to tech culture like so many of the people around me have.

“I’ve been thinking a lot about tech-debt in communities of color lately. Access to technology in communities like the one I’m from is incomparable to the access to technology that most people who become successful in Silicon Valley have. Most Black schools have pretty abysmal computer science labs. Students don’t have computers at home, let alone an internet connection. So next to figuring out what stock options mean, a lot of people who are trying to break into technology need to catch up on people who’ve been exposed to tech for much, much longer.”

How do you think your background in behavioral science helps you in your work? Both as a product designer and as an entrepreneur.

Having an academic background has mostly triggered a thirst to keep learning. I like watching things and studying their patterns, which is another side to this inclusion discussion that I find remarkable. When people stop learning and stop questioning the way the world works around them, things like bias, discrimination and racism come into play. I’ve been trying to fix that conversation by prototyping solutions that can actually be implemented, and found that in order to work in tech – an academic path is very beneficial but in most cases, not an absolute necessity. Especially in the field of design.

What would you say are your big motivators?

I love it when people tell me I can’t do something and then proving them wrong. I get a kick out of that. I decided to speak out more because I want kids to know how to deal with similar situations. I want them to say, “I want to be like Melanie when I grow up.” I didn’t have anyone I could be like growing up. So I collected all this advice; some of it I can use, some of it I can’t. Bits and pieces of people that have inspired me along the way, and I try to keep improving myself like that.

Okay, let’s just go macro real quick. How do you feel about the state of tech in 2016? What excites you, what frustrates you, and what would you like to see change?

I’m most excited about  companies that exist to do good and challenge the way we think about the world, so I’m really in love with Honor. I love what they’re doing, I love the problem that they’re solving. It’s really exciting because it’s a human problem and everyone benefits from it. The workforce, the families, even the way they run the company.


The things that frustrate me? There are still too many non-problems being solved. Things that are only accessible by a very controlled, homogenous audience. I’m worried about the accessibility of technology. Many processes continue to optimize and drive down prices, making things more affordable – but there very few processes that focus on making life more enjoyable.

What advice would you have for folks coming from similar backgrounds as yours who are hoping to get into tech?

You need that hustle. A strong will to succeed because you will hear “no” more often than people will tell you “yes.” Shit will get hard. But if it’d be easy, anybody would be doing it. We experience racism and other difficulties every single day. Use that sadness and anger to lift yourself up in the right direction. If people don’t believe you, build whatever you can and try to prove them wrong. With Front & Center I’ve tried to hack a system that I found didn’t make sense. So I decided to make a change. I measure my success by the opportunities I create for other people. I want people to join me in designing a more inclusive future.

“You need that hustle. A strong will to succeed because you will hear “no” more often than people will tell you ‘yes.’ Shit will get hard. But if it’d be easy, anybody would be doing it. We experience racism and other difficulties every single day. Use that sadness and anger to lift yourself up in the right direction. If people don’t believe you, build whatever you can and try to prove them wrong.”

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Expand on that.

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

What did you work on while at Google?

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

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

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

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

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

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

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

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

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

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

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

Yes absolutely.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Can you expand on what’s been lost?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

How did you first discover tech and get into tech?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

How do feel like you fit into Silicon Valley culture?

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

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

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

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

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

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

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

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

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

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

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

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

Where do you see yourself in the future?

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

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

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

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

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

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

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

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

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

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

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

Full disclosure: I basically have handlers who will make sure I don’t say anything too off-color. But generally, the only things I avoid saying are partisan things because I run a non-partisan organization. Talking about being a woman in technology, or a gay woman in technology in San Francisco, is not partisan.

Or a “loud-mouth lady gay,” as you called yourself in your application?

Yeah. Being a loud-mouth lady gay led to me realizing that, “Oh my God, I’m no longer suited to work for other people.” The last boss I ever had said that she thought I would do much better working by myself. She was correct.

Okay. So let’s start from the beginning, Tell me a bit about your early years and where you come from.

I am from Brooklyn. I’m a fifth generation Brooklynite. My family has been there since 1890 on the maternal side and since 1910 or so on the paternal side. So we’re pretty run-of-the-mill Eastern European Jews who left Europe when Europe became less-hospitable. I’m from the part of the Brooklyn where the accent is from and where hipsters still don’t live. So when you think artisanal crafts, do not think of the Brooklyn that I grew up in or the Brooklyn that my mother currently lives in. My mother would have no idea by what you meant by “artisanal soap,” “artisanal candles,” “artisanal gefilte fish.” She just wouldn’t know what any of that means.

I respect that. What part?

Bensonhurst.

Bensonhurst, I do not know Bensonhurst.

Bensonhurst is where the “Honeymooners” took place, where “Welcome Back, Kotter” took place, and where “Saturday Night Fever” took place.

Wow, that’s really amazing. No, you don’t have an accent, but you have the East coast swagger, which I appreciate as a fellow-East coaster.

Thank you.

When did you first get interested in tech, and separately, when did you become interested in politics?

Those actually overlap a bit. I’m older than I look, so the first time that I used the internet was my first week of college. This was 1995 and I was definitely an early adopter. I was one of the first people in my circle to learn HTML, and I took some entry level design courses in college.

I first became strongly interested in politics the night of the 2000 Presidential election. I was with a group of friends in North Hampton, Massachusetts, and we were watching the returns. When Florida went blue my friends were like, “Okay, great, Gore’s president,” and went to sleep. I was like, “I’m just going to stay awake and watch the rest of the returns.” This meant I was awake and alone when Florida was suddenly red.

“Being a loud-mouth lady gay led to me realizing that, ‘Oh my God, I’m no longer suited to work for other people.’ The last boss I ever had said that she thought I would do much better working by myself. She was correct.”

Keep in mind it was the middle of the night in Florida when this happened. First the state was declared for Gore and then — what was the story? — they found a truck filled with ballots for the Republican candidate, George W. Bush. This was a very surprising thing to happen in the middle of the night, and a very surprising thing to happen in what was an overwhelmingly Jewish section of Florida. And then the recount dragged on forever and wound up at the Supreme Court.

I think that night was the first time I became cognizant of how important voter turnout is. The presidential election should never come down to multiple recounts of ballots in a single county in America. At the same time, I was young and doing other things with my life. In 2004, I decided it was time to get more involved in politics. I met Sharif, a man who was staring a project called Swing the State. People would register as volunteer online with Swing the State, and Sharif would help them travel into swing states to do voter registration and get out the vote work. I told Sharif I wanted to help, and that was that. I was somewhat technical at that point, and this was a highly technical project. It was really just Swing the State and MoveOn.org that were organizing volunteers online and then deploying them on the ground back then. Swing the State was my first political tech project. I just kept going from there.

So, at first, you were working in tech, and politics was a hobby?

No, actually, I was investigating police misconduct for the City of New York.

Okay, walk me through this whole thing. I’m going to stop talking. You take me from the beginning.

My career path makes absolutely no sense. Let’s set the stage. It’s 2000 and I lived in Western Mass, because that’s where I thought young lesbians lived. In 2001, I came to my senses and moved back to New York, because it turned out that Western Mass is actually where middle-aged lesbians live. So, I moved back to New York, and puttered around for a bit. In 2004 I got a job investigating police misconduct for the City of New York. This was an awesome job: I had a badge, and cops had to answer to me, and that was great. I met Sharif that year and started running Swing the State in my spare time with Sharif and about ten of our friends. This was a fiercely partisan project. We were like, “We do not want George W. Bush to win re-election. That would be terrible, we must put an immediate end to this.”

The 2004 election did not work out the way we wanted the 2004 election to work out. I continued investigating police misconduct until 2007. Then I got a phone call from a friend from college and he offered me a job at MySpace.com. I literally hadn’t heard from this guy in years. Do you remember MySpace?

I was very active on MySpace. It took me a long time to get it out of my top Google results.

Oh, that’s really funny. I was active on Friendster and then someone I worked with investigating police misconduct literally said to me, “Oh that’s right, you’re old. You people are all still on Friendster. Young people are on MySpace.” And I was like, “I’m young too!” So I created a MySpace profile that I literally never checked. I never really used MySpace until my friend from college called to offer me this job. I was wholly unqualified for this job —I feel like this is a key part of this story. But he knew that I had been running a civic tech project, and as far as he was concerned this meant i worked in technology. I was like, “No, no, no, I have passion projects in technology.” But, you know, this was 2007 and you could accept jobs that you weren’t remotely qualified for. So in 2007 I stopped investigating police misconduct, moved from New York City to Los Angeles, and started working at MySpace.com when MySpace was pretty much the center of the online universe.

I got to LA and realized I didn’t actually have any friends in LA. This meant I had a lot of downtime and decided it was time to start another election project. And that’s where Long Distance Voter comes from. From me not having any friends in Los Angeles.

“This was 2007 and you could accept jobs that you weren’t remotely qualified for. So in 2007 I stopped investigating police misconduct, moved from New York City to Los Angeles, and started working at MySpace.com when MySpace was pretty much the center of the online universe.”

That’s beautiful.

It’s amazing what not having friends will do for your spare time and your creative drive. So backing up a bit, in 2004 I thought that the best way to increase voter turnout was to register more voters. This was a very common thought back then. So Swing the State and our partner groups, like Acorn and America Coming Together (rest in peace both groups), were part of this massive, nationwide, voter registration effort. At the end of the day, it didn’t seem to have much of an impact on turnout. Progressives were out registering conservatives four to one, but we certainly weren’t winning elections.

By 2006, I started to wonder if voter registration was related to voter turnout in any way. I’m not an academic, I didn’t have an actual funds to study this, but my gut told me to focus on something other than voter registration. I decided that my next project was going to focus on some group of people who were already registered to vote, who were highly motivated to vote, and who had some sort of roadblock that I could clear using the internet. If we’re being honest, I mostly wanted to stop doing door-to-door voter registration. I’d done a ton of that in 2004 and 2006 and it was just terrible. So late in 2006 I decided I would never again carry a clipboard.

Anyway, so now it’s 2006 and I’m in Vegas—where all great ideas are born—at a brand new political conference called Yearly Kos. A group of us were sitting around, and my friend John wanted to go ride a mechanical bull. Everyone was drunk, and I was like, “Do not go ride a mechanical bull. This is a terrible idea. Instead of riding a mechanical bull, I need you to help me figure out something.” And John was like, “What?” I was like, “I need to come up with a group of people who are already registered to vote, who are highly motivated to vote, have some sort of roadblock that we can clear using the Internet, because I really, really do not want to have to go door-to-door every again.” And he was like, “What about absentee voters?” And I was like, “What?” And he was like, “When I did absentee in college, it was really confusing and I’m still not sure if my absentee ballot was counted. Is anyone running an absentee ballot project?” And I was like, “I don’t think so.” And he was like, “Great, we should do that,” and then went off to ride this mechanical bull. And that is Long Distance Voter’s origin story.

“I’m working at Myspace during the day as a product manager. So during the day I’m identifying what people need from the internet, and what sort of tools we should build, and how you could run an engineering team. At night, I’m working with my friends, and we’re doing our nerdy voting project. I continued this pattern of having working as a product manager during the day, and volunteering with my friends to save democracy at night, through several jobs.”

I don’t remember how riding the mechanical bull worked out for John. He obviously lived to the morning, because we were all fine the next day. Anyway, that conversation happened in 2006. In 2007, I moved to Los Angeles, had no friends, and reached back out to John about his absentee ballot website. John and I recruited a bunch of our former coworkers (we had all investigated police misconduct together for the City of New York) and we started building the Long Distance Voter website. We had $5,000. I think there were ten of us—there were ten of us. Everyone took five states. We called the Secretaries of State, we asked them to walk us through it. We called every Secretary of State in America, and we asked them how you voted absentee in their state. (This is incredibly boring, I realize. Just picture us all investigating police misconduct, that makes it more exciting.) We built what was essentially a Wiki, with one page per state, and we had our first half million visitors within six months. So, we were like, “Alright, let’s keep doing this. We’re awesome.” And so we kept working on the site. Everyone was a volunteer.

We added more features to the site because users asked us to. People asked, “Hey, how come you don’t have a voter registration tool?” So we threw the Rock the Vote voter registration tool into the site, and quickly became Rock the Vote’s number one partner — in terms of registrations — out of 500 groups using their tool. People started asking us when early voting happens, so we created early voting page which is still the first hit on Google. So we just kept going with the site.

Meanwhile, I’m working at Myspace during the day as a product manager. So during the day I’m identifying what people need from the internet, and what sort of tools we should build, and how you could run an engineering team. At night, I’m working with my friends, and we’re doing our nerdy voting project. I continued this pattern of having working as a product manager during the day, and volunteering with my friends to save democracy at night, through several jobs.

That’s amazing.

Thank you. It makes no sense though. Everyone in voting assumed this was my full-time job. I’ve been Debra Cleaver from Long Distance Voters since 2008. At the same exact time, I was Debra Cleaver from Myspace, then Debra Cleaver from Truecar.com, and then Debra Cleaver from Change.org. It’s like I was Batman, but less cool. I had an election alter ego who did not get to wear a mask and a suit.

I feel like we’ve I’ve heard a lot of exciting things you’ve worked on, have we missed any of the really proud and exciting things?

No. Honestly, spending my twenties investigating police misconduct for the City of New York was awesome. I would also say—and this is a fact—that the New York City Police Department is the best trained, most heavily regulated, police department in the world. The fact that New York City has civilian oversight is really meaningful. A lot of the nonsense that happens in other places does not happen in New York, or doesn’t happen without immediate repercussion. New York City’s Internal Affairs Bureau is the model for Internal Affairs departments throughout the country. Living outside of New York, I’m astonished that there are police departments with no civilian oversight. If the police are only accountable to themselves, and not to civilians, then we are living in a police state. That is the literal definition of a police state: one where the police are only accountable to themselves. In New York City, the police are ultimately accountable to the civilians that they police. That doesn’t seem to to be the case outside of New York. New York City is certainly not without its racial and systemic biases, obviously, but it never felt like the wild west. Outside of New York, things seem nuts right now in terms of police misconduct.

What have been your biggest struggles over your career path, be it directly related to work or even personal? What have been the hardships you’ve had to overcome?

I loved investigating police misconduct. It was just awesome. I was also our union shop steward. In addition to investigating police misconduct and running Swing the State with my friends, I also engaged in a three-year battle with management. I filed all these large group grievances against management, and won them all, and that was just amazing. So I had this really amazing time, investigating police misconduct, and being a bad-ass, and driving the management nuts, and being a union shop steward. And then one day I realized, “I need to get the hell out of government.” Once you win massive group grievances, your career is pretty much over, you’re black-balled.

“Working at MySpace was amazing. If you saw a woman in the engineering department, there was a very good chance she was in charge of her team. The MySpace technical team was run by women. So my introduction to working in tech was to have all these bad-ass, fierce, unapologetic women running the show.”

So, MySpace came at the exact right time. Working at MySpace was amazing. If you saw a woman in the engineering department, there was a very good chance she was in charge of her team. The MySpace technical team was run by women. So my introduction to working in tech was to have all these bad-ass, fierce, unapologetic women running the show. The women were incredibly smart and really scary, and they’ve accepted me as one of their own, and I always had a great time at work. The guys at work would tell me that that wasn’t the case at other tech companies and that their wives and girlfriends had a much harder time working in tech. And, I said, “Oh, that’s weird, because I feel like MySpace is female dominated.” And they were like, “Well, MySpace is the exception to the rule.”

And then, I went to work at TrueCar.com, which was an automotive tech company. It was male dominated, but still a really wonderful professional experience. It wasn’t fun, the way MySpace was fun, but everyone was a professional. We came in, we did our work, and we were all paid well, so we were motivated by money, not necessarily our love for the automotive industry. Even though it was a predominantly male staff, I never thought it was a boy’s club. And then I moved to San Francisco, and the San Francisco tech scene was unlike anything I’d ever seen.

Tell me more.

I came to San Francisco tech companies and I suddenly was surrounded by people who had never heard of professionalism. Everything from “please show up to work on time” to “please do not tell jokes during the day, this is inappropriate”. I’ve never considered professionalism and fun to be at odds. I was like, “Professionalism is what enables a diverse group of people to together.” My team at Myspace was widely regarded as one of the happiest teams in the company, and Myspace was a big company. My team was 50% loudmouth white homosexual, and 50% somewhat quiet engineer who had grown up in India. So this was not a group of people that you would expect would really gel, but we did. The quieter coworkers kept the loudmouths from being bonkers and off the wall. And the loudmouth homosexuals made things light hearted and fun. And we were absolutely the happiest team in the company, and professionalism was why we could work together. Ken, my lead developer, is a wonderful person, also a devout Christian. So just during the day I didn’t make off-color comments about religion, because that would inappropriate. We just didn’t make off-color race or gender jokes in general, cause that would be inappropriate. So we had this team at Myspace that was diverse in terms, and race, and religion, and country of origin, and still managed to laugh all day, every day.

Then I moved to San Francisco, and suddenly things were just not funny. It’s not funny when you’re in HipChat, and someone is literally telling dick jokes. And it’s not funny when you’re the only woman on a team of 35. I’m used to having more men than women on a team, but I’m certainly not used to having 35 men and one woman. And I’ve found that when you build a homogenous team, people forget all about professionalism because they don’t have to moderate their behavior to accommodate people who aren’t exactly like them.

“Then I moved to San Francisco, and suddenly things were just not funny. It’s not funny when you’re in HipChat, and someone is literally telling dick jokes. And it’s not funny when you’re the only woman on a team of 35.”

I’d never actually articulated to myself, ‘I work in a boys’ club’ until I started working in SF. I’m a short-haired, loud-mouthed dyke and I’m very comfortable with predominantly male environments. But a boys’ club is very different beast entirely.

You might need to pepper me with some questions now because good Lord, do I have stories. So many stories.

What have some of your experiences been like?

Okay, some of the stories are just kind of hilarious. I had one software engineer who would groom at his desk. He’d trim his nails and comb his very long beard and it was just kind of weird. And his hygiene just wasn’t great. Really sweet guy, but terrible hygiene. And he would take off his shoes and his feet smelled terrible. I just pulled his boss aside and was like, “You got to deal with this. We have to have a shoes on policy at work.” His boss looked pretty uncomfortable, but there was no way I was going to deal with that mess. I told the boss, “Maybe you can talk to the boys about hygiene. You don’t need to say any of us have brought it up but it would be great if people could bathe once a week. That would really be great.” That’s a funny story: you don’t expect to have to tell a 40-year old man to bathe, but not the end of the world.

“I’ve found that when you build a homogenous team, people forget all about professionalism because they don’t have to moderate their behavior to accommodate people who aren’t exactly like them.”

Less funny story. At one job a software engineer punched another software engineer in the face at the holiday Christmas party. Boys will be boys, I guess. One of the boys was mouthing off at another one of the boys, and the second boy had enough of it and punched the first boy in the face. On one hand, I would say a lot of us had wanted to punch this guy in the face. On the other hand, but you may fantasize about punching a co-worker in the face but you don’t actually do it. And they weren’t boys—they were grown men and we were at the company Christmas party. There was an open bar, and everybody was drunk and dancing, and out of the corner of my eye, I see people who look like bouncers and I think, “Those look like bouncers.” And then I immediately realize those are actual bouncers because one of the engineers just punched another engineer in the face. So that wasn’t great [chuckles].

I was like great, “I’m getting out of here.” And the CEO literally catches me as I’m leaving and he’s like, “Hey, what just happened?” And I was like, “Well, one of your engineers just punched another one of your engineers in the face.” And he was like, “Why?” And I was like, “I don’t know. I haven’t ever punched anyone in the face so I can’t really imagine.” And he’s like, “But you have to have some idea.” And I’m like, “Well, first, your engineers are a bunch of man children, and second of all the one who was punched in the face is really objectively very annoying, so he probably mouthed off to someone who’s much bigger than him and got hit in the face.”

At this point I’m just trying to leave because I was pretty drunk—there had been an open bar—and I’m like, “I just cannot be talking to this jackass CEO right now.” And he’s like still talking to me, and I was like, “Hey, I’m not trying to tell you how to run your business but you need to call the company attorney, like right now.” And he’s like, “No, no, I don’t think it’s a big deal. I don’t think we need an attorney.” And I’m like, “One of your employees just punched another employee in the face at a company-sponsored event. You need an attorney.” And he’s like, “No, no.” And I was like, “Oh my God, how can I make this clearer to you?” I said, “You need the other gay Jew. I am your product manager, the other gay Jew is your attorney. You need that gay Jew. I cannot help you with this situation. I don’t know why one of them punched another one in the face, but I do know that you need an attorney.” And, of course, the next day the attorney was like, “Thank you for having him call me.”

“I would also routinely wind up the only woman in a room of company leaders. This was a global company so we had 20 country directors at least 50%, maybe 60%, were women. But if we had a meeting of the country leaders, we would only fly men in.”

This situation was ironic because just a few hours before the Christmas party another product manager and I had gone to the CEO to the lack of professionalism with the engineers. He was like, “What do you mean?” And I was like, Well, in the past week, one of them stood up and yelled at another one for no apparent reason. Another decided that he’d had enough of a meeting that we were in, so he slammed the table and announced that he was “done talking about this.” And what he was done talking about was literally his team’s plan to finish a project, so he stormed out. We had another male engineer—I should stop saying male engineers, actually, they were all men—throw something in a meeting because he also didn’t feel like he should keep answering questions. And the questions were always about work, like, “When will this be done?”, or, “Can you help us understand why this project is four weeks late because we have outside partners who are waiting.”

So anyway, the day of the holiday party I went to the CEO to talk about the lack of professionalism, and several hours later one of the engineers punched another one in the face. Way to underscore my point.

God that was a long-winded story. I would also routinely wind up the only woman in a room of company leaders. This was a global company so we had 20 country directors at least 50%, maybe 60%, were women. But if we had a meeting of the country leaders, we would only fly men in.

What??

Right? So I started talking to the CEO about this, calling him out. The first time I walked into his office and said, “Hey, I think we need to talk. I just left a meeting of 15 people and I was the only woman in the room. And the only reasons I was there is that I happen to be based out of San Francisco, and the meeting was here, and I couldn’t help but notice that you didn’t fly any women in.” And he was like, “What do you mean?” And I was like, “More than 50% of the country directors are women. So when you were choosing who to fly in, why didn’t you choose to fly any of them in?” And he was like, “Oh, I hadn’t thought about that.” And I told him, point blank, “Listen, it’s pretty uncomfortable for me to say this, but I think you’re running like a boys’ club here. I don’t think this is conscious, but when you personally picture leadership, you seem to only be picturing men, and we need to think about what that means for our company.”

“There would be these meetings with say me, and the CEO, and say two other men. And I would just pitch an idea at CEO, and he’d say, ‘Well, that’s a terrible idea.’ And one of the other guys would repeat verbatim what I had maybe five minutes later (because we would have all agreed going into the meeting like that was the best plan), and the CEO would be say ‘That’s a great idea! Debra, why don’t you come up with ideas like this?'”

And at first he seemed pretty responsive to this, but nothing actually changed. I was good friends with the head of HR and we started to have unofficial conversations about this. Then then they became official conversations. And, oh my god, there would be these meetings with say me, and the CEO, and say two other men. And I would just pitch an idea at CEO, and he’d say, “Well, that’s a terrible idea.” And one of the other guys would repeat verbatim what I had maybe five minutes later (because we would have all agreed going into the meeting like that was the best plan), and the CEO would be say “That’s a great idea! Debra, why don’t you come up with ideas like this?”

The first time it happened everyone laughed because we all thought the CEO was kidding. And the CEO asks us why we’re laughing and one of the guys says, “Well, I mean this is Debra’s exact idea. She just said this five minutes ago.” And I was like, “Yeah, that’s my exact idea.” And the CEO was honestly confused. It was like he hadn’t been in the room at all. That was the first time I had encountered sexism that was like cartoonish in nature.

“It started to feel like a comical exercise in gender stereotyping, only it wasn’t actually funny.”

I was at that company for about a year and a half. It reached the point where the conversations with HR were no longer unofficial, and the CEO and I would get into it regularly. I would say things to him like, “Hey, your revenue projections are nonsensical. I can’t even imagine where you’re getting these numbers from, but based on our actual revenue patterns, we’re going to have layoffs.” And he would say, “Well, you’re just not being optimistic.” And I was say, “No, I’m just being realistic. We have a huge staff, so I think this is a problem.” Other times he would say that I wasn’t metric-driven, which was really bizarre to me since I was always trying to talk to him about revenue. Once after he told me that I wasn’t “metric driven” I said, “I don’t know ‘metric driven’ means what you think it means, but the metric that I want to discuss with you is revenue. Revenue is a fancy way to say the money we need to operate our company. Whenever I try to talk to you about revenue, you shoot down the conversation, but then you want to spend literally hours every day second guessing every minor decision I make because you’re worried that it will have only a .4% increase in conversions instead of .6%.”

This became a constant refrain with him. He would routinely say, “Well, you’re just not numbers driven,” or “Debra, you don’t have good ideas.” Because money clearly wasn’t an important metric . And it started to feel like a comical exercise in gender stereotyping, only it wasn’t actually funny.

I was going to leave, but then we got this new female president. I decided to stick around, and see if things improved. Things got really shitty, and literally I would get criticized for the tone of voice that I used in email. As if emails have a tone. During the last two months the president started telling me—I am not making this up—that I needed to smile more during the day. But the reason I stopped smiling was that it was just not fun to come into work. My guys—my team—actually noticed and asked if I was mad at them. And I was like, “What do you mean?” And they were like, “You used to joke around with us every morning and now you don’t joke around at all. You just put your headphones on and you work.” And I was like, “No, no, I’m not mad at you guys. I have things going on in life.” I was amazed that they’d noticed because, like lots of straight men who work in engineering, they were just completely oblivious to what was going on around them.

Oh, and the one performance review I had read like that that article that was going on around on Facebook that highlighted the phrases and that are only used in women’s performance reviews. Like “abrasive.” I was “abrasive.” We did 360 reviews and this feedback came from from male colleagues who hadn’t been pulling their weight at all until I was on staff. I would say to them things like, “Hey, we pay you six figures and in return for that we expect you to do the work that you’re assigned during the day in a reasonable timeframe.”

I’m trying to think of funny stories for you, but none of this was funny. My life was a parody of stereotypical sexist behavior.

Man, you worked at a comical extreme it sounds like.

The amazing thing about this is I had just left this automotive tech company, which was just not like that at all. It was professional, it was fine and sometimes I was the only woman in a room, but only because it’s tends to be men who are jazzed at the thought of working at an automotive tech company. The company where I had the most negative experience was a social enterprise where people really prided themselves on how aware they were of systemic racism and sexism and things like that. Irony alert.

Major.

Do you want to know how that ended? This is the only good part about this entire situation. There was this project that the CEO was really stoked on even though it was a really stupid idea. It was a clusterfuck of a project but my team took it on because we’d been working on something else forever and needed a change. I spoke to the heads of every major division in the company and we figured out literally the only path forward. I got buy off from everyone before talking to the CEO. Then someone’s assistant scheduled like seven hours of meetings, and I was like, “We don’t need seven hours of meetings, but whatever.”

We start the very first meeting, there was a room full of people, and I said to the CEO “Hey listen, everyone in the company has agreed there’s only one path forward, so all we really need right now from you, CEO, is for you to sign off on this path forward so everyone can get started.” And he spends the next seven hours laying into me as a person. How it’s clear I “haven’t really thought about the project” and “I’m not taking it seriously”. After a few hours I pulled the other product managers into the meetings as well because I needed backup. Both of them repeatedly told the CEO that we all agreed that there was only one path forward. So the CEO starts saying how it’s clear (somehow) that I’m “not thinking about the metrics and blah, blah, blah.”

So seven hours later, it’s time to leave for the day, and someone has scheduled some dinner that I’m supposed to go to. But I’m in tears, which has never happened to be before at work (don’t worry, no one saw). And I called a friend from New York. This guy has known me for two decades, and assumes someone has died because I’m crying. And I tell him, ”I’m crying because I have feelings. And I’m not used to having feelings. And I don’t know what to do about this.” My friend tells me, ”Go home, get a pint of ice cream, and watch Scandal or something.” And I’m telling him I can’t just go home because there’s some fucking dinner I have to attend. And he was like, ”Okay. You know how to handle this. Do not talk during the dinner. Just sit at the edge of the table and drink your wine and don’t talk to anyone.” And I was like, ”Okay. Got it. Just drink quietly.”

“So finally I say, ‘You wanna know what’s going on?’ And I held up my fork and said, ‘I would rather stab out my own eyes with this motherfucking fork than talk about our goddamn job or our goddamn misogynistic prick of a CEO.'”

So I get there and no one’s there, and I start drinking. Everyone else was a full 30 minutes late. And then we sit down and I’m like at the very end of the table, and someone’s like, “Hey, Debra, come sit at the head of the table.” Because normally I’m the funny one. And I’m like, ”Oh, fuck.” But I tell myself, ”Just keep drinking. Just keep drinking. You have this plan.” And everyone keeps trying to engage me in conversations, but I’m not willing to talk. And none of these people have ever seen me not say a word for 90 minutes, so it’s starting to get weird that I’m not talking.

Someone, I can’t remember who, just wouldn’t let it go and kept trying to engage me in conversation. And at this point I had probably a bottle of wine on my own, and I was like, “I just don’t really want to talk right now.” And someone’s like, “No, for real. You’ve never been quiet this long. What’s going on? Blah blah blah.” And they just kept trying to talk to me about work and about the meetings we’d just had and whatnot. So finally I say, “You wanna know what’s going on?” And I held up my fork and said, “I would rather stab out my own eyes with this motherfucking fork than talk about our goddamn job or our goddamn misogynistic prick of a CEO.”

And then I went back to eating my food while everyone else sat there stunned and quiet. I ate my food, finished my bottle of wine, went home, the next day took a sick day, and the next day was told to come into work at 8AM (which is two hours before I get to work) to be fired. And so ended my illustrious career working for someone else. Misogynistic prick in question did not fire me himself, he had a woman do it. And while she was firing me, she was said, “I am really sorry about his behavior the other day.” Because she had been there in the all-day meetings.

I still think that the fork incident was my finest professional moment. I can see how calling calling someone a misogynistic prick would be a problem, if it wasn’t objectively true. But in my defense, he was a misogynistic prick. This was just a statement of fact.

As an aside, the guy who punched the other guy in the face—not fired. The guy who’s throwing things in meetings—not fired. The guy who posted a bunch of swastikas on Facebook publicly while identifying the company he worked for—not fired. None of these people were fired. Me—a bottle of wine in, state objective truth about our boss—fired. So, I don’t know. I still think it was a good way to go out.

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

I’ve never been interested in technology for technology’s sake. I’m not like, “Look at this awesome app that I downloaded that lets me throw angry birds at something.” I’ve always been interested in technology as a way to solve other problems. In 2004 when I first started wading into this political work it my question was, “How can we use the internet to organize volunteers?” Now, I look at the internet as a whole and think, “this is the most powerful and least expensive information distribution system we have ever seen.” The internet is the single most important advancement in human communication and information distribution since the printing press. Only it’s cheap It’s accessible for everyone. You could host a website for seven bucks a month at DreamHost and the whole world can see it.

“I’ve never been interested in technology for technology’s sake. I’ve always been interested in technology as a way to solve other problems.”

For me it’s not that we’re going to solve the issues plaguing American democracy with technology, it’s that we can use technology to amplify the solutions we’ve already identified. I’ve focused on education—how can we educate all Americans about voting without spending a bajillion dollars? We can use the internet. Every day I see so many examples of people using technology in creative ways to solve problems that are much bigger than “how am I going to get my laundry done” or “where can I find a taxi.” I love what we can do with technology, but I don’t necessarily love technology itself. I will use the most boring, established, non-sparkly technology to solve really big problems.

“For me it’s not that we’re going to solve the issues plaguing American democracy with technology, it’s that we can use technology to amplify the solutions we’ve already identified. I’ve focused on education—how can we educate all Americans about voting without spending a bajillion dollars? We can use the internet.”

In terms of culture there interesting things afoot in the tech world and in the valley. The younger women entering the field now have mentors that women my age didn’t necessarily have. And these mentors have had enough of this weird, sexist bullshit. There are a number of women in tech groups, and lesbians in tech, and a consistent topic of conversation is how do we protect these younger women? How can we make sure that sexism doesn’t thrive in the valley? And what do you do when your team is off the wall bonkers and out of control? A lot of us also think about how lack of diversity affects not just the companies, but the world. Who has access to technology and therefore who has access to information. There is so much thoughtful conversation going on around access issues.

I’ve personally come to believe that your user base will resemble your staff. If you have a staff that is 90% white men, you might wind up with user base that is 90% white men because your team will build a product that meets the needs of the people they know. You have these companies that are hegemonist and therefore the solutions they come out with are pretty defined and not very creative. In my field the way that plays out is through the techniques we use to reach underrepresented voters. We’re talking about low income voters, voters of color, young voters, urban voters. Basically people who aren’t straight white men. Traditional voter outreach tactics don’t seem to reach these groups, likely because elections and campaigns are generally run by straight white men. So these men run campaigns that speak to other straight white men, and a significant percentage of potential voters are left out of the fold. If we want to have an electorate that isn’t just straight white men, and we want to have candidates that aren’t just straight white men, we need to bring people who aren’t straight white men into the fold. I want to reach the people who are not being reached, and therefore I will not build a team of all straight white men, even if I live in San Francisco. If we all look the same, we’re going to reach the people who are already being reached.

“I’ve personally come to believe that your user base will resemble your staff. If you have a staff that is 90% white men, you might wind up with user base that is 90% white men because your team will build a product that meets the needs of the people they know.”

I think that’s true for every tech company. And just see right now in 2016, there is some sort of shift going on, and people are calling out the lack of diversity, they’re calling out the VCs, they’re calling out the CEOs.

Yeah, it could be why we’ve hit a wall with a lot of these unicorns, of like—you had all the potential to globalize, but at some point you hit a wall.

Yeah, you somehow were unable to reach people who didn’t look exactly like you. And it turns out there’s only so many users who look exactly like your team.

Oh, i just read a quote the other day on Facebook that was great. “When the lights come on, a unicorn is just a horse in a party hat with a fake horn.”

These unicorns, when you remove the VC funding, they’re often just failed companies.

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

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

Wow!

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

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

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

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

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

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

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

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

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

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

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

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

I remember that.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Right. I know the feeling.

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

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

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

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

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

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

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

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