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

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

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

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

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

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

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

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

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

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

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

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

How did you first get interested in tech?

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

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

How’d you end up in SF and in tech?

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

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

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

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

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

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

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

What were your first impressions of Silicon Valley?

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

Walk me through your experience working in tech.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

What has your experience been like transitioning into investing?

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

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

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

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

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

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

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

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

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

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

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

What have been your biggest struggles?

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

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

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

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

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

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

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

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

What are your biggest motivators?

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

Where have you found support networks?

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

What would you like to see change?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

I was born at home in San Leandro, in the East Bay, just south of Oakland, so I’m a Bay Area native. I have three sisters who were also born at home, one older and two younger. I soon moved to Hayward where my parents still live now, and grew up going to the New Haven Unified School District because my mom taught there. And she taught everything from performing arts to working with kids at risk and is now doing dropout prevention. My dad is a doctor and his practice is in Fremont, so we’d commute from Hayward not too far to Union City.

I would say looking back now one of my formative things about my upbringing is that I’m mixed. I’m part Native American. San Carlos Apache from Arizona, Eastern Band Cherokee from the Carolinas, Hawaiian a couple generations but originally from Cebu, which are islands off the Philippines and Japanese from Osaka. And English, hence my last name. Apparently some bastard blood from King Henry V or something crazy like that. My aunt, I think, did a bunch of family trees but at some point, everyone connects back.

I think given that ethnically diverse background, my parents’ approach to raising us was grounded more in a common indigenousity, a common indigenous approach to simply having a connection to this earth and to this land. So we grew up farming our whole hillside. Everything from beans and corn that are way taller than me. Tomatoes and kale and all sorts of greens and squash. All different types of flowers and succulents. It’s still thriving to this day. Growing up, it was really annoying to go into the backyard and do all of our compost and create our own soil, but I got a chance to help build that little organic garden.

It was frustrating being out there in the backyard watering, when other kids are playing and I was always out there working. Though I think it did ground me and I still have a deep connection and sense of place on this earth. It also reinforced a farmer’s work ethic from my dad and his father who farmed on the eastern shore of Maryland. So there was definitely some influence from my dad and influence from my mom. She’s a performing artist so I have the analytical side from my dad and the creative side from my mom. While I was a baby, she took me around on tour and she would do different types of modern performances. Integrating dance, poetry, theater, and native influenced stories. My mom was just so generous with everyone. I remember growing up being so annoyed that we’d have people over to our house all the time. Staying at our place or coming over for brunch. She’d really try to take care of people and give as much to the local communities as possible. To this day she’s dropping off car loads of food, clothes and gifts for people all the time. When I was a kid I think I was annoyed but now I realize it had a much bigger impact on me in terms of my perspective on giving, even when you don’t think you have anything to give.

Where we lived was also interesting in the sense that we were in the foothills so our area really felt quite safe and unique. Every home was uniquely built. In one sense I felt secure in our middle-class lifestyle. But then on the other hand, near us or below us in the surrounding areas of where I went to school and other parts of Hayward and Oakland there was much more disparity.

So I felt like I got to see a pretty big spectrum growing up and then going into school in Union City. The elementary school I went to was in Decoto which had some notorious gangs and unfortunately some violence. So I think I was also exposed to that just walking around from daycare to school or staying after school.

I think I was super lucky as a kid. My parents put me in a Chinese preschool. I have a few vague memories of making Chinese symbols. So that was interesting. And then with kindergarten, there was a morning session and an afternoon session but my Mom was working at school so I just stuck around for both sessions. I think as early as first grade I started staying after school in math club with Mr. Fogel who was able to make a lot of things, even algebra, super accessible and fun. Using tactile blocks and objects. I think those things probably were also formative early on. It’s silly to me to even think about that because for most kids who go to amazing schools now that’s probably the norm. But for a public school with a big population of immigrants and English as a second language and super diverse minority school, I think those kind of after-school programs were unique.

Eventually I took a GATE test that put me onto a whole other track from elementary school all the way through high school. It’s pretty crazy to me to think that probably fundamentally altered my whole course. I was in 2nd grade but then I got moved to a 3rd grade class. And so, it just started accelerating from there to the honors track all the way through high school. The environment of those classes is very different than the other classes that were probably more chaotic. A lot crazier. With diversity of levels of knowledge and access. So, it’s crazy to me to think that things like that exist and hopefully they’re still getting funding. A lot of those kids went onto Berkeley. I was the only kid to go to Stanford out of a high school class of maybe 4000 plus students, which is unfortunate. I think more folks should have the ability to go there.

The other thing that probably shaped my perspective on how I operate now is that my parents didn’t take care of everything for me and hover. I don’t know what these things are called, hoverboard parents or helicopter parents [laughter].

Hoverboard parents!! It’s the 2016 version.

Yeah exactly. Rather than my mom making me lunch in the morning, I would make lunch for me and my mom and I don’t know if they were intentionally doing that or not, but that principle of empowering me, or putting the responsibility on me to take action extended throughout my life. So, for example, as there were a lot of Latino kids and a big Hispanic community in this Decoto area, I remember going out for the first time at recess and somehow being invited to play this ball game. I still have a couple of memories of how exhilarating that was and just cutting and kicking and having a great time. So that naturally inspired me to want to play more soccer. I went to my parents and told them I’d really love to play in a league. I was probably around seven or eight years old. They just told me to go and make it happen. And I’m like, uh, okay. So I remember being so annoyed as a kid that I would always have to fill out the release forms and apply for these things on my own. Not to say that they weren’t supportive once I started doing it because then they would come to all of my games and obviously drive me around and buy me gear. But they really wanted me to take that initiative and once I took that initiative they were super supportive.

The recess soccer games were another small thing that fundamentally changed my trajectory because from that point on, I just started playing more and more soccer. First with a local club, called the Patriots. That was my first team. Very patriotic. And then I just excelled and got invited to play with a select team. That coach was from Germany. Coach Burnett. And because he came from Germany he had such a better understanding of the fundamentals of the game than any American coach. The types of drills and discipline that we would have was just so much better than a lot of the other teams and we did pretty well for not having much in the way of resources. Eventually I was noticed by a wealthier club, Lamorinda, which is a club in Lafayette over the hills of Oakland as you go into Walnut Creek. It’s a very affluent area. I got noticed by that coach and they recruited me to play with them as Coach Burnett was beginning to wind down his team. So that also then exposed me to a whole other world of wealth. Just a whole other extreme than some of the kids that I went to school with. So I felt like I really got to see a pretty big spectrum of socio-economic status.

With that team we traveled to many places around the world. To Europe. To Barcelona in Spain multiple times. To Sweden multiple times. That wasn’t always easy. I remember having to fundraise from my parents’ friends and family. It wasn’t easy compared to the other teammates whose parents would just pay for them to go on these trips. But nevertheless, I think it really opened my eyes to different cultures, whether in South America or in Europe. I think that also fundamentally shifted my perspective. I remember being in Sweden, just amazed about how clean and how easy the public transportation system was and how friendly everybody was. I was just like, “Wow!” How beautiful the people were. It was amazing. I had such a good time there and continue to go back when I can.

The next big shift was playing in these tournaments like the Dallas Cup, that got me noticed by some coaches from Stanford. I started developing relationships with those folks. I got hurt in my senior year of high school. I hurt my lateral meniscus in a tournament. And so, that was right at the time when I was in conversations with recruiting, who encouraged me to apply. I had exceptional grades like most kids who first get into Stanford but what I could get from financial aid was actually bigger than what I could get from a scholarship to play soccer. I think soccer influenced me getting into Stanford, but I think that the academic merit also equally contributed to getting in, so that was a cool to start another trajectory.

It’s so interesting to me, how much exposure you had to both the lowest socioeconomic status in school and the highest socioeconomic status through soccer.

Yeah. Like some of the mansions, and private this and private that, [chuckles] to other people immigrating from Central America, or elsewhere and really having to struggle. And you have to learn how to hang with both.

I think I went through different phases in school. Wanting to be more cool and rebellious and wear baggy clothes and get into rap music. I definitely went through that phase. I definitely had my fair share of getting into trouble, whether it was pranks or doing things that we weren’t of age to be doing. There was a point before actually going to high school where I did get into a little trouble and I remember my parents picking me up at school and just crying and bawling. This is all while I’m getting straight A’s but I had this kind of dual personality of being exceptional in the classroom but also wanting to be cool with the cool kids and the influence of gangs and other sorts of stuff in schools. Anyways, I remember my parents just bawling and being so upset with me. It was the first time I realized that my actions have an impact on other people. So I think that was the big sort of ah-ha moment before going into high school. I just felt so grateful that I had that experience before it was too late. I thought, “Hey, I’ve got to be more responsible. I can’t just go along with some of these bad crowds. I’ve got to make decisions for myself and recognize that I have to take responsibility for my actions.” That was a huge turning point that helped keep me straight through high school because I didn’t want to have that type of experience again. I felt really lucky that it wasn’t anything that affected my record.

“There was a point before actually going to high school where I did get into a little trouble and I remember my parents picking me up at school and just crying and bawling. This is all while I’m getting straight A’s but I had this kind of dual personality of being exceptional in the classroom but also wanting to be cool with the cool kids and the influence of gangs and other sorts of stuff in schools. Anyways, I remember my parents just bawling and being so upset with me. It was the first time I realized that my actions have an impact on other people.”

Did you have any idea at that point what you wanted to be? Was there a specific point you became interested in design or technology?

It’s pretty crazy. I’d go to Stanford for occasional events like Native American Pow Wows. I’d been on the campus, but for whatever reason I thought that Stanford was just all doctors, lawyers, and business people. I was totally unaware of engineering or design as a track. I don’t even recall using the word design. I was definitely exposed to art and performing arts because of my sisters and my mom. But yeah, even today, to just realize that when you’re in the Valley and you think everyone knows about all this shit. Many kids around this area and in east bay probably don’t.

I would say also one other thing that influenced me and my three sisters was that my mom came from a lineage of really strong, independent women. My grandmother on my mom’s side, was a nurse and she raised them by herself single-handedly. With my great-grandmother, it’s kind of the same thing. In Arizona, she had her own home and was really independent. Horses and cattle and riding around. I think that matriarchy and having three sisters also shaped my values and perspective on gender. It has continued to play into some of the work that we do to this day. Investing in diversity. I think just having more respect for women. My dad was just more reserved and calm and zen-like. My mom was much more of the fiery one that would really take the initiative on things. So I think that’s also had an influence, but yeah, back to the question on how I got interested in design.

“I’d go to Stanford for occasional events like Native American Pow Wows. I’d been on the campus, but for whatever reason I thought that Stanford was just all doctors, lawyers, and business people. I was totally unaware of engineering or design as a track. I don’t even recall using the word design.”

So getting to Stanford was amazing. And with influence from my dad, I thought maybe I should go down the pre-med track. I started off with Human Biology, which is a really great major at Stanford that’s pretty interdisciplinary and I finished most of my pre-med requirements. From stuff in the lab to all the fundamentals. I also took a lot of courses at the medical school and that was when I started to realize that I wasn’t sure I wanted to be in these lab settings. It didn’t resonate as much with me.

At the same time too, that shit was kind of hard. I went from not studying ever to being with some of the best students in the world. So, I definitely remember being kind of shocked like, “Oh, wow!” I actually need to do some work here and at the same time playing division one soccer. That was challenging. I remember waking up super early for practice and after that I’d go to class. I would just be so tired. So sleepy and that was really challenging.

One of my teammates, Bronson McDonald was volunteering at this local non-profit called Mural Music & Arts Project in East Palo Alto. He was helping start their History Through Hip Hop program. He invited me to come out to some of the mural making that was going on at that time. That was the first time that I experienced research process like primary research, trying to figure out the local stories related to the theme like immigration which was a controversial theme at that time. Interviewing experts and local folks, and synthesizing all that. Getting everybody’s ideas out, and then visualizing it. That was the first time that I got exposed to the word design because that was a mural design process. So from the research to the design, to scale it on the wall, to unveiling it and having a big celebration.

That was when I first started having an awareness of the design process. It was just so powerful for me to spend time with local at risk youth which again is this conundrum in one of the wealthiest cities. All these resources and then to have a place so nearby where there’s so much disparity. It continued on this theme of having access to the folks at Stanford who are like princes and other crazy stuff, to folks that just don’t have the same level of privilege at all. Through the mural project I started to continue to volunteer and I started to realize, as they were applying for grants, there was this Community Technology Foundation of California (CTFC).

I looked around at my friends at Stanford. A lot of my friends didn’t go to East Palo Alto. They had no exposure to these stories. I’m like, is anybody actually going to come walk into the “ghetto” to look at some of these beautiful mural art pieces? And even if they do walk up to the wall, they’re not going to have a sense of all the stories and the meaning behind the wall. I thought what if we start putting these murals online? And started to think about a virtual mural tour. That’s when I started trying to apply the design process more to the web in software. I started hacking Google Maps which wasn’t open at the time and using different tools along with a couple of folks at the Mural Music and Arts Project like Zach Pogue and others. We pitched and got a grant to develop a project and document, digitally, many of the murals in the local Ravenswood City school district and up the peninsula to try to be able to expose these stories more digitally. That was the first web project that started to get me excited about the power of technology and power of software.

Concurrently I’d say one of my good friends from Stanford, Dan Greenberg, introduced me to Professor BJ Fogg at Stanford who’s done a lot around persuasive technology and how you can use technology for good. I ended up taking a Facebook class which is where I started to cross paths with Ben Blumenfeld, my co-founder at Designer Fund. That class was the first time that Facebook had opened up their platform for third party developers. Our objective was to build applications from scratch and launch them on the Facebook platform. We formed a small team. I basically worked on a status message app that has all the features that we kind of take for granted now, like embedding photos, linking, replies; that kind of stuff. Collectively with classmates who worked on a bunch of other projects, we got something like 10 million users in 10 weeks. Mainly making these spammy apps like hugs and kisses, but I think that had a huge impact on me because it was the first time I realized that we could have this mass interpersonal impact. I can’t think of another class in history that has reached that many people.

With the help of BJ, I started to do research in his lab on these mechanisms of how can you use social applications to get people to do good things. So, it really started to open my eyes to the power of software and that’s when I began to shift my courses into human computer interaction. I started to meet other people that were part of this small major at the time. It was inter-disciplinary between CS, linguistics, psychology and I started to take as many classes as I could in that track. That’s when I started to get more formal training in usability and user research. Around the same time at the end of that Facebook class, I presented my project and I got noticed by Chris O’Malley, who was at Venrock. Venrock is one of the oldest VC firms. They’ve invested in Apple. They’re from the lineage of Rockefeller money. He invited me to come on over, have lunch and meet the team. I didn’t have any awareness about venture capital, or really much about startups. Even though we did these kind of social apps. This is probably around 2008 or so. I worked in-house at Venrock with the senior designer and a couple of developers, and we would basically help build product for some of the companies that they were incubating. I spent most of my time with AskMeGo, which is a live questions and answer site. It was great. I got to help acquire a few hundred thousand users, similar to Aardvark which was acquired by Google. I worked on helping people get their questions answered and how to surface really good questions. That was a great first experience in tech.

So you joined Facebook Fund during college as well?

I then went back to grad school because I wanted to play for one more year. I got hurt one year at Stanford, so I wanted to play a 5th year of soccer, and I also wanted to keep going deeper into design. I lived off-campus and was biking down Lytton Ave in Palo Alto, near the old Techcrunch office and I ran into Dave McClure on the street, who I knew from the Facebook class. He was like, “Hey, what are you up to? Want to help work on this thing, Facebook Fund?” I was like, “That sounds cool,” but I just brushed it off. On top of everything that I was doing, playing soccer, taking super intense classes, then getting more into HCI, and doing research in the lab, I also worked most of the time, and paid my way through school.

One of the side jobs I had was at a high-end catering company that would do a lot of on-campus events. There was actually a VC related event that I was catering and I was learning about some of the start-ups and then I ran into Dave McClure again, and he was like, “Hey, man, you should probably come over and learn more and help out on Facebook Fund.” At that point I finally followed up, but I think it’s just crazy to me to think that you could have those kinds of serendipitous opportunities that are connections from class and you run into people on the street. The density of awesome people that you have access to is so easy to take for granted.

Then I joined Dave to help run design for “fbFund,” which was a joint venture between Facebook, Accel and Founders Fund. There were around 22 companies we invested in and I was responsible for running a small in-house design team to do short sprints with the portfolio companies around user acquisition, retention and revenue. It was amazing because I got to see all these companies in their infancy, when it was just a couple people around the table. Little companies like Zimride with Logan and John before they turned into the multi billion dollar company Lyft. Little companies like Run My Errand with Leah before she turned it into TaskRabbit. Alain and the Wildfire team before they grew it and sold it to Google for hundreds of millions. It’s crazy to see those companies form from the ground up.

“One of the side jobs I had was at a high-end catering company that would do a lot of on-campus events. There was actually a VC related event that I was catering and I was learning about some of the start-ups and then I ran into Dave McClure again, and he was like, ‘Hey, man, you should probably come over and learn more and help out on Facebook Fund.’ At that point I finally followed up, but I think it’s just crazy to me to think that you could have those kinds of serendipitous opportunities that are connections from class and you run into people on the street. The density of awesome people that you have access to is so easy to take for granted.”

Facebook wanted to have these companies build their products with “social” built into the product. Facebook Connect, the little button that you see around to log-in everywhere was new at the time, so they wanted more companies to showcase that. This is also when I started to realize that I needed to scale myself. I couldn’t serve all 22 companies. It wasn’t possible. So I started to think how could I take a lot of the learnings from the design school. How could I take a lot of that design thinking and prove that it works in the context of early stage start-ups. That includes office hours, talks, workshops, etc. I brought over whiteboards that I borrowed from the d.school. Scott Doorley who is now the Creative Director was so gracious to literally let me come with a truck and pick up a bunch of their equipment and take it over to Facebook. I had to figure out how to scale design and with the success of Facebook Fund, Dave went on to start his own fund.

As I was finishing up grad school, I was also starting to go deeper into design. I took a course, entrepreneurial design for extreme affordability. On one hand, I’m exposed to of all these social apps that are scaling and on the other end of the extreme, I’m working on low-cost water pumps, storage, and irrigation for rural farmers in Burma (Myanmar). It was a year long course where we did a lot of research, prototyping, testing, and went out to Burma during spring break. Being out in the field trying to empathize with people rather than just trying to push our solution onto them. Really trying to understand their needs. I remember sitting there in the field, observing this young girl, who was probably the same age as my sister at the time, a young teen, or maybe even younger, squat down and pick up gallons and gallons of water on her shoulder. She would go back and forth with tons of water over the course of a day. That’s one of the big things keeping her from going to school. I just had empathy for her. Especially given that I had a sister too, around her age. That again informed my perspective on what is meaningful impact. What’s the power of these technologies to really fundamentally affect people’s lives. I continued to do projects like that through grad school. For example in South Africa with FrontlineSMS:Medic. I worked on mobile texting apps to help virtual health workers report infectious diseases. Another amazing experience. That was another thing that opened my eyes to the power of technology to help. Walking into some of those hospitals and seeing people on stretchers. I think it grounded me in terms of technology that actually matters, that makes a difference, versus technology that just plays at our egos and our vices.

After finishing up grad school, I remember working harder during that time period, than ever. Of course, not sleeping, and all of the classic things. Anyway, 500 Startups didn’t have a brand, or even a name. We didn’t have a logo mark, or a typeface, or a website, or any money in the bank, or any space, or anything. The job, really, was just to do everything that I could, to help get 500 Startups off the ground. Launching our site, designing and helping close on 10,000 square feet in Mountain View, and doing that buildout. I really credit Dave, to just empower me. During my time there, I focused on our accelerator program and the problem of how to scale design services. How to scale great design, to dozens of companies at a time.

“I worked on mobile texting apps to help virtual health workers report infectious diseases. Another amazing experience. That was another thing that opened my eyes to the power of technology to help. Walking into some of those hospitals and seeing people on stretchers. I think it grounded me in terms of technology that actually matters, that makes a difference, versus technology that just plays at our egos and our vices.”

I experimented with everything. Design Sprints, talks, workshops, pattern libraries, UI kits, all sorts of things. It was great. I got to work with companies like Punchd, that was acquired by Google, and invested in Bēhance, which was acquired by Adobe. I worked with Tiny Post, acquired by Trip Advisor. I got a chance to not only help hands-on with companies, but also start to invest. One day while meditating at my place in Palo Alto, I just had this a-ha moment, which was like, shit, am I having long term impact with these companies? If I follow up, three, six months or a year down the road, how many of these companies will still be practicing these human-centered methods? What I noticed was that it was exponential decay. You would improve someone’s design sense, or their awareness of customers, but then if no one on the team was there to help sustain it, and to continue modeling and practicing these design behaviors, it’s not sustainable. People would just revert back to whatever they’re comfortable with. If you have an engineering background, you’re probably just going to focus more on solving problems from an engineering perspective, or a business perspective. It really bummed me out, that as I started to look back, I’m like, man, I’ve been working on all these companies over the past few years, but am I having long term impact with them?

In one of the books that I was reading at the time, Disrupt, or one of the conversations with John Lilly, the lesson was to do the opposite of what you’ve been doing. I was like, okay, I’ve been spending all of this time trying to make startups more design oriented. What if I do the opposite and help designers take the path of entrepreneurship with the thesis being if they get involved earlier on with great engineers and business people, they’ll increase the probability that they could make better designed products and services in the long run. That would also make my job a lot easier rather than trying to parachute in and solve people’s design problems. They would build that core competency in-house.

Simultaneously, Ben’s and my path crossed multiple times, at the Facebook class, Facebook Fund and we even collaborated on projects like peace.facebook.com. We kept in touch felt similar challenges and started to interview over 60 designers that we really respected and tried to understand why aren’t more designers taking this path of entrepreneurship. It kind of boiled down to lack of education, role models and capital. If you look at most of the most of the sources of capital, even going into schools, it’s primarily engineering based. When you look at professors and programs, they weren’t really preparing designers to start companies or to join companies early on. Or to be designers in the way that we expect them to be now. Every designer we spoke to was like, “Hey, if you try to solve this challenge, I’ll help you with time and/or money.” That was really encouraging. All these early conversations with influencers like Scott Belsky and others who said, “Yes, I’ll help.” I just remember thinking back, like, “Wow.” If those people didn’t say, “Yes I’ll help,” and want to pay it forward and give back to the design community, I don’t think that we would have continued on. That eventually led to Ben to take a sabbatical because he was maybe the fifth or sixth designer there and had been there for five or six years. He wanted to take a little break. We started going on hikes like Hidden Villa in Los Altos and then maybe working one day a week and then two days a week and then three, and it turned into all of our time trying to figure out how we can help more designers build businesses with meaningful impact.

Walk me through the decision to officially start Designer Fund.

It was around 2011 that we were doing the designer interviews. We felt like there was a real need to create a community of designers who were in tech who were building these companies from the ground up or joining early. At the same time, I felt, philosophically, that I wanted to work with less companies. I wanted to have more impact. That means, inherently, there’s just less companies that I can work with. With Dave’s blessing, I wanted to start to focus on Designer Fund full time. Over the course of 2011, I started to progressively decrease my time at 500 Startups and increase my time working on Designer Fund as an independent entity. I’m super lucky that Dave along with a number of other awesome investors were early supporters of Designer Fund. I’m super grateful to Dave McClure, Vinod Khosla, Jonathan Heiliger, Marc Andreessen, Eric Thomas, Shannon Callahan, Dave Morin, Chi-Hua Chien, Brandon Zeuner, Ryan Swagar, Marcus and Andrew Ogawa, John Lilly, Alex Diehl and many others. Folks that, I think, really just believed in the importance of creating an ecosystem and they saw the importance of design and were willing to support different educational events.

We then started giving grants to designers who were starting companies. For us it was an awesome way to give back to design community through free events, resources like our Designer Founders ebook, and through grants. As we moved into 2012, we started to formalize some of those things like writing larger grant check sizes and developing a better system for running different types of events. I think that’s when we even started with our first Women in Design event that Maria Molfino hosted. We went from mentorship programming to helping set up designers with formal advisorship positions with an equity stake. And also starting to operate as a band of angels where we’d help get our friends to co-invest in companies started by designers. We built on that momentum and then by 2013, we started to realize, “Wow, there’s a huge need need here.” Our inboxes were full of all these designers who are coming to us seeking support in one way or another, from funding, to transitioning to a new opportunity, to improving their career, and then all these companies were coming to us wanting to build their design teams, and so that led to the genesis of Bridge. We had all these great people coming to us but it was just Ben and I. We had to create some better way, a more scalable way of doing this. Previously I had built some internal tools with Kevin Xu, who’s now at Stripe, and the first version of a way for us to help process applications. We had all these applications for designers who wanted grants and so we thought maybe we can repurpose some of this technology to help us process all these applications from designers and all these applications from companies. That was also another big lesson for me, that some of the technology that you build early on, even if it’s scrappy MVP, really could accrue value over time and really magnify and scale your ability to serve people rather than just trying to do everything manually. That is obvious in retrospect. So we went from experiments in 2011 to formalizing events and grants in 2012 and then we launched Bridge and started angel investing in 2013.

Given our mission is to help designers build businesses with meaningful impact, one way of doing that is by helping designers build companies from the ground up as co-founders. What we soon realized was not every designer should be a co-founder, and actually, starting a company from scratch is hard as fuck. It’s so hard. At the same time there’s another path. Designers join existing companies that are doing well and on a growth trajectory. The next Facebook, the next Uber, etc. Joining one of those companies early on, arguably you could have just as much impact and you’re going to have a great experience learning. You’re going to meet a bunch of awesome designers and engineers. You might have a life-changing economic outcome, and just be in a better position to start a company yourself in the future.

On one hand, investing is great to help designers who are ready to be founders. Bridge, on the other hand, is about investing in future design leaders. It also related to our thesis that we believe that companies need to build design at their core. They can’t outsource it. It’s just like you don’t want to outsource your engineering, and great engineers attract other great engineers and so great designers attract other great designers. We felt strongly that helping build and educate design teams would bring a lot of value to companies and help accelerate the growth of designers.

When we launched Bridge, it was an experiment. We didn’t really know what was going to happen, so I just quickly worked with another designer and mocked up a site and worked on the positioning, but I didn’t spend a ton of time on it. I didn’t know if this was actually going to actually going to work. We partnered with some amazing photographers like you (Helena Price) and with the help of Laura Brunow-Miner and others to try to get perspective of a day in the life and what it’s like to be a designer at some of these top companies. Like Pinterest, Airbnb and Dropbox. Places that we felt truly value design. We’d meet the founders, we’d meet the design team. We’d check out the product. We’d make sure it’s a place where we would want to work ourselves because there’s just so much noise out there.

“We believe that companies need to build design at their core. They can’t outsource it. It’s just like you don’t want to outsource your engineering, and great engineers attract other great engineers and so great designers attract other great designers. We felt strongly that helping build and educate design teams would bring a lot of value to companies and help accelerate the growth of designers.”

And when we launched, it just got an overwhelmingly positive response. Way more demand from companies and designers than we could possibly fulfill. It was profitable since day one and we wanted to see if we could do it again. We ended up running another program that same year in 2013, in the Fall. Again we had amazing results of tons of designers applying, tons of companies wanting to participate. So then we realized that it wasn’t a fluke. Again in 2014 when we launched it again, Bridge 3, there was an amazing response. Our acceptance rate was tougher than Stanford or Harvard. We were really solving a need here for companies to help build and educate the design teams, to help designers accelerate their careers and hopefully become better designers and leaders.

And at the same time too, we started to get more and more companies coming to us seeking funding. They knew that we could actually add value and help build and educate design teams. There’s only so much that Ben and I can do as angel investors. There’s only so much we can do by calling up our friends to try to pool our money together to invest in them, so we thought, “Okay, I think we have enough data here that we’re ready to raise our first fund.” That was in 2014. We raised primarily from individual designers, great folks from some of the top companies around the valley, entrepreneurs, a couple of families, our own money and a few institutional funds. Now we’re managing over 20 million and we have a much clearer value proposition for people when they come knocking at our, we can say, “Hey, we can invest between $100K and a million dollars. Our average check size is $250K.” Ultimately we wanted to create a better experience for designer founders and designer entrepreneurs we wanted to partner with.

That was 2014. I think looking back, I don’t think we looked like anything else at the time. I don’t think there was any fund that was focused on design. There was no fund that also had this professional development program that was generating revenue and being profitable and had this community of designers. We just looked very unique, I think. Very different compared to the classic fund approaches. We wanted to build this ecosystem. Ben and I aren’t MBAs or coming from stereotypical investors wearing khakis and a button up shirt every day and vests and stuff. I think people were pretty surprised. I don’t think I was aware at the time, so it’s only looking back that I realize there’s not many diverse investors out there. Certainly not at the time from these different design backgrounds. Not at the time from an ethnicity perspective. I just met with a friend recently who told me that he’s been doing some research and there’s only about 30 general partners out there who are Hispanic and I was like, “Uhhhh, oh, okay.’ I didn’t even know that at the time. So if I factor that stuff in, probably the odds weren’t in our favor. We just didn’t have a long investment track record. We didn’t have a traditional background. Didn’t have what people who invest in funds would traditionally look for so thinking back I’m super grateful for all the folks like our advisor, Steve Vassallo, who took a chance on us and believed in our mission and believed in our approach.

“Ben and I aren’t MBAs or coming from stereotypical investors wearing khakis and a button up shirt every day and vests and stuff. I think people were pretty surprised. I don’t think I was aware at the time, so it’s only looking back that I realize there’s not many diverse investors out there. Certainly not at the time from these different design backgrounds. Not at the time from an ethnicity perspective.”

I guess what I’m trying to say is, each of those steps along the way from Venrock, to Facebook Fund, to 500 Startups to Designer Fund was uncomfortable. It was a stretch. It was almost that beginners naïvety. Looking back I don’t even know if I would do it again. Looking back it just doesn’t line up with what the norms at the time.

There were a lot of sacrifices too. Ben and I didn’t really pay ourselves. So many nights just working at our dinner table and doing all the classic stuff that I think any start up needs to do. Being super frugal, doing everything that we can to find alternative streams of revenue, engaging our community and a volunteer base. So scrappy. Doing events and getting sponsors and if it wasn’t for them I don’t know if I would pay rent that month. Just all the things that I think any entrepreneur would have to do. Seeing your bank account at zero or negative. In that way I think it was really great for Ben and I to have that deep empathy with all the companies that we invest in. I think it’s important never to lose sight of the struggle.

There’s all this hype that’s going right now and all these folks flocking to Silicon Valley maybe for the wrong reasons. It’s not a lottery ticket. Whereas for us, I don’t think we really ever wanted to be investors just for the sake of being investors. We felt that by investing, we could have a long-term impact with these companies. We could have an equity stake and be long term partners versus just consulting and parachuting in.

“There were a lot of sacrifices too. Ben and I didn’t really pay ourselves. So many nights just working at our dinner table and doing all the classic stuff that I think any start up needs to do. Being super frugal, doing everything that we can to find alternative streams of revenue, engaging our community and a volunteer base. So scrappy. Doing events and getting sponsors and if it wasn’t for them I don’t know if I would pay rent that month. Just all the things that I think any entrepreneur would have to do. Seeing your bank account at zero or negative. In that way I think it was really great for Ben and I to have that deep empathy with all the companies that we invest in. I think it’s important never to lose sight of the struggle.”

For example we have a poster from Facebook’s hacker way. “We don’t build products to make money, we make money so that we can build better products.” I think that’s always resonated with us. Where investing is not an end for us. It’s a means for, again, having meaningful impact and ultimately we want better designed products and services in the world. When we say better design, I think of that in a holistic sense. I think of that as an opportunity to impact someone’s life at a really deep level, and the opportunity to have breadth and scale across their life and across the globe. Of course we want to make a ton of money and generate great returns, but we think we can do that in a way that is aligned with our values.

“we have a poster from Facebook’s hacker way. “We don’t build products to make money, we make money so that we can build better products.” I think that’s always resonated with us. Where investing is not an end for us. It’s a means for, again, having meaningful impact and ultimately we want better designed products and services in the world. When we say better design, I think of that in a holistic sense. I think of that as an opportunity to impact someone’s life at a really deep level, and the opportunity to have breadth and scale across their life and across the globe. Of course we want to make a ton of money and generate great returns, but we think we can do that in a way that is aligned with our values.”

Since closing our first fund in 2014, we’ve been able to invest into some really great companies. Our largest investment is in Stripe, the global payments platform that’s really empowering commerce and online payments around the world. They’re now allowing anyone to set up US businesses and get that off the ground, it’s just amazing. Another one of our portfolio companies, ZenPayroll which is now re-branded as Gusto, is helping all these small business owners across the country, many not in tech, run their payroll. That’s really the backbone of the American economy, small businesses. We’re also investors in companies like Omada Health, which spun out of IDEO’s health practice. They help prevent people from getting diabetes, which then saves employers money and makes health plans more efficient. It’s like everybody wins. Individuals, the company, society. I just wish I could find ten more of those types of companies in all these different sectors that have, traditionally, been underserved from a user experience standpoint like financial services, education, health, business tools, creative tools. Over time I think we’ve been really blessed and fortunate to have lots of great people around the table to support Ben and I. An approach that we’ve always taken is that we’ve always surrounded ourselves with people that are amazing at what they do. When we first closed our fund, before even starting to invest, I think we interviewed maybe two dozen top investors that we respected and got perspective on what they thought worked and what didn’t work. We’re constantly practicing our own design process on ourselves and on our own business. We’re not just preaching design. We’re actually being hands-on and making our own tools, making our own site, doing a lot of our own stuff. Branding for example. I think it’s important to not lose sight of that. We primarily have been focused on just building, helping our companies and letting the work speak for itself, because I think you just see how there’s so much noise out there. We prefer to focus on the fundamentals of building a product that really solves a consumer’s pain point and need.

So, I have a question. In another interview, the idea was brought up that people tend to invest in what they know, and the problems that they can relate to. From your perspective, with your upbringing and being exposed to so many different socioeconomic backgrounds and cultures and not coming from the Silicon Valley pedigree—how does that affect you and what you choose to invest your time and money in?

I think there’s a number of companies that we’ve invested, for example ZenPayroll, which is now Gusto. We felt the pain of trying set up our own payroll, and file taxes, and all this back end office stuff. It’s like the last thing that we want to do with, especially when you’re really small. So I think in those cases, we felt that pain. Even creating our free resources like our Designer Founder’s e-book. We used Stripe to process payments. We used some of those tools ourselves as users and that’s one of the things whenever we look at a company—whether or not we’re the target user or not—we really try to use the product, and really dig into all the interactions. Which I think it’s pretty surprising how often most investors don’t do that.

Most investors aren’t really product focused and don’t really use the product which continues to surprise us. That’s okay, everyone has a different approach. When you start to dig into a product and start to put yourselves in the shoes of the user, even if we’re not deeply familiar with the problem, we can still try to put ourselves in their shoes and experience what that company is building. I think our ability to empathize with folks who are different than us allows us to imagine how a product or service could really impact someone’s life, hopefully for good.

“Most investors aren’t really product focused and don’t really use the product which continues to surprise us.”

Of course there’s some things like design tools, for example, like Framer Studio. We invested in them, and it’s like, “Yeah, we totally understand the need to prototype mobile web apps with code. With live data where you can make one change really easily and propagate that to a bunch of other things versus static mockups. We totally get that we’re moving towards a world where we need to build interactive prototypes. Some things like that, it’s really obvious for us to be able to have a point of view on. But then there’s other things where we’re actively looking for things that are outside our comfort zone. What are those areas that are traditionally underserved from a user experience standpoint? What are the industries with old, dinosaur incumbents that don’t really care about the user and just take advantage of them? Insurance, for example. They win based off of advertising campaigns, not on product and not by the user experience. I think there’s so many opportunities like that where because we are naturally curious, we’re going to go explore those spaces even if we don’t intimately know them or have experienced them.

“We’re actively looking for things that are outside our comfort zone. What are those areas that are traditionally underserved from a user experience standpoint? What are the industries with old, dinosaur incumbents that don’t really care about the user and just take advantage of them?”

I think in that sense, we actually like when we come across something that we don’t know a lot about initially, and then we have a whole research process. We bring in experts to help us. I’m actually looking for those opportunities where it’s going to be outside of my comfort zone because that’s where design could have the biggest delta or the biggest impact. Of course I’m going to look for the stuff that I know already is obvious. But the non-obvious things are going to be the most exciting things for us. Back to the example with Omada Health. My grandmother and great-grandmother have diabetes. So I remember seeing those needles, and just how horrible that process is. I know that my mom and others are at risk of being diabetic and that I actually was able to get her to go through the Prevent program at Omada, and lose ten pounds so I could see the impact that it was having in my personal life. That being said, we’re still open to finding more opportunities, whether it’s in mental health or other chronic illnesses, that just are totally preventable and with the help of technology we can accelerate prevention. I hope that in the future, we’ll be able to have more alignment with the health industry and the government to be able to even prescribe some of these digital therapeutic technologies.

My last question for you would be, just based on the lessons that you’ve learned, what advice would you have for young entrepreneurs or designers just getting started out in this industry?

One lesson is finding the right partner with complementary skills. Ben and I have really complementary paths. Me going through more of a Stanford HCI and research approach and Ben coming from UCLA with a formalized visual and graphic design approach. Me coming from early stage startups through venture capital firms and Ben coming through the rocket ship of Facebook, one of the most successful tech companies of our time. Another lesson is don’t underestimate the importance of finding a great opportunity. Just finding a company, a brand where you can learn a ton at, make a bunch of relationships with great engineers, designers, expand your network, and get exposed to what it takes to build a great product and scale it. If you get exposure to that early on it’s going to set you up for so much more in the future.

I want more designers to start companies. But I don’t think that’s always the right path for a lot of people. I think by joining an existing company right before that inflection point of growth, I think there’s a lot of benefit to doing that and I think you’re going to set yourself up to be in better position if you want to start a company in the future. There’s going to be exceptions and people like Joe and Brian who started Airbnb. They came from a very non-traditional route. Joe being an entrepreneur and Brian working at a design consultancy. It’s totally possible to start something when you don’t look qualified. You don’t look like any of the other teams that most investors look at. That’s totally possible but I think those guys were naturally entrepreneurial. If you are going to go that path to entrepreneurship, then I think it’s so important that you find a partner. For me I found Ben. Using the example of Joe and Brian, Airbnb wouldn’t be possible without their technical founder Nate. It’s so important to find both a design and engineering partner in that early team. I think that’s arguably more important than anything else at those early stages. To summarize, join a successful brand while it’s on its upward trajectory and learn everything you can while you’re there. Or if you are going to start something, really make sure you’re partnering with someone that you can make a long-term commitment to. Like Ben and I have made a minimum 10 year commitment to our mission and to each other. If you can’t make that type of commitment to someone, then maybe reconsider whether or not you want to get married and start a company together. [chuckles]

“Don’t underestimate the importance of finding a great opportunity. Just finding a company, a brand where you can learn a ton at, make a bunch of relationships with great engineers, designers, expand your network, and get exposed to what it takes to build a great product and scale it. If you get exposure to that early on it’s going to set you up for so much more in the future.”

I was born in Virginia, but I was raised outside of Philadelphia, in the suburbs—like really, really suburban. I was kind of shy as a kid. It wasn’t that I didn’t want to socialize, I just couldn’t seem to figure out how to do it. Or how everyone else was doing it. I went to a small private elementary school, there were about 35 kids in my whole grade, and everyone there was nice, like there wasn’t any bullying or anything, but it was just an incredibly homogeneous school.

I got this label of being the “smart kid.” But the reason people thought I was smart was because I got good grades. And also because I had started kindergarten early, ‘cause I started reading really young, so I was a year younger than everyone in my class. When you’re like 8 years old, that one year makes a big difference. And I didn’t think getting good grades was interesting at all, and reading was just like, something that happened. Like I literally found a book on the side of the road and I took it home and it was this book of animal poems and that’s how I learned to read. Getting good grades was just what was expected of me by my parents, you get straight A’s in school, like that’s what you do. I didn’t feel intellectually challenged in school at all. And so I kind of hated that label, I hated being “the smart kid,” it was like because I got good grades in school, that was all anybody knew me for. Because everybody gets a label, right. There was one girl who liked to draw, so she was the “artsy kid.” But if you were the “smart kid” you couldn’t also be the “artsy kid” because you can only have one label at a time. And I hated being reduced to something so one-dimensional just because I’d done what was expected of me.

I found a lot of the people and the kind of stimulation I was looking for online. We got AOL when I was 8, and I would play a lot of RPGs through chat rooms and mailing lists on there. I loved MUDs, which are these text-based RPGs, no visuals, everything is a written description. They’re still my favorite kind of game. Especially the smaller ones, where the people who made the game were just other characters you hang out with in the game, and there was such a strong sense of community that was built by the players themselves, not handed to you by some big game company or whatever, and the makers were always building new areas for you to explore and doing silly things, because it was just text, right, so it was easy to make more stuff. But those games became my world, like my whole social world.

“We got AOL when I was 8, and I would play a lot of RPGs through chat rooms and mailing lists on there. I loved MUDs, which are these text-based RPGs, no visuals, everything is a written description. Those games became my world, like my whole social world.”

I’m really old school about games, I like where people just sort of agree on a set of rules and then the rest is left to your imagination. I love how you can turn those worlds into anything you want. I think at some point in real life, like way into my adult life, I realized “fuck it,” like you can do that in real life too. Everything is malleable. It’s this really beautiful thing, like games are actually just reality and vice versa.

I kind of stopped playing games in high school but then I ended up spending a lot of time on random online forums and making friends on there. It was the same sort of thing where you had to figure out all these social norms and learn how to make friends and politic a bit. And that felt more natural to me, reading and typing and making friends that way, than doing it in real life, where in real life people kind of look at you and tell you who you are based on something that’s sort of out of your control. Like I didn’t know my dad had an accent until I was in junior high. I didn’t know I didn’t look white until somebody told me. I didn’t know I was like, a woman, until I started getting that kind of attention.

I think I just got along better with people online because nobody knew who anyone was in real life and it didn’t really matter. Like I was in this guild for awhile and they finally figured out I was 9 years old and then it got awkward. It was a big deal if you even knew someone’s first name in real life instead of their character name or username. I mean this was all pre-Facebook or whatever. And I remember people would have, like, one photo they would upload to the game website and be like “This is me! This is what I look like!” So yeah it was just very detached from the real world and I liked that I could just be me and not be this flat “smart kid” character, where like, any time you had an original thought people were like “oh, it’s ‘cause she’s smart!” which seemed incredibly reductive and boring and not interesting to me in real life.

“I think I just got along better with people online because nobody knew who anyone was in real life and it didn’t really matter. Like I was in this guild for awhile and they finally figured out I was 9 years old and then it got awkward.”

Anyway. So then I went to a Quaker high school, which was super impactful in the way I was brought up. It was much more challenging and interesting. It just kind of like—it just gave me really good framework on the rest of life. Quakers are sort of like the hippy branch of Christians that are all about equality, and everything was about sitting in a circle and talking out your feelings. They believe everyone has this same sort of “that of God” inside them, everyone has something worth sharing, and that’s what brings us together. So it was just really influential for me.

Let’s see, what else? My dad is Persian, but he grew up in Germany, and my mom is Chinese-Indonesian, but she grew up in Indonesia. I was in suburban Pennsylvania so there was a lot of culture mixing and everything. My mom lived in Indonesia when I was younger and my dad was in Pennsylvania. I spent a lot of time in Indonesia and a lot of time in Pennsylvania. I’ve always just kind of felt in between everything. Everything is kind of the same, it’s all a matter of perspective and I think that’s carried with me throughout the rest of my life.

I went to college at Tufts in Boston, came out of college, wanted to move to San Francisco because it was warm and different. I had been on the East Coast—North East—my whole life. San Francisco was like a whole other world for me. Being in a super suburban environment was—I just kind of felt like I never really belonged. It was not a great place for creativity to thrive. I even felt like being in Boston or D.C. or wherever, there was just such an East Coast way of doing things, and on the West Coast it was like, “Be free! Be yourself, whatever.” I was really overwhelmed when I first moved to San Francisco because I was like ,”Oh my god! There are other people my age that are doing things that are crazier than me, and like, how did I miss out on this? My life is over. I’m 21.” Not true, of course—and I sort of learned to get into the flow and the balance of things. Everyone here is so, so introspective and there is always something you can fix and change about yourself. And that appeals to such a big part of my brain and is very exciting. But then, I think especially in recent years it’s kind of been around managing, like, alright, there’s a point where you can be happy and where you can decide what you do and you don’t want to do. So, yeah.

“I was really overwhelmed when I first moved to San Francisco because I was like ,’Oh my god! There are other people my age that are doing things that are crazier than me, and like, how did I miss out on this? My life is over. I’m 21.'”

When did you first get interested in tech as a career?

Kind of by accident. So I was—I thought I was going to go into environmental policy after Tufts. And then I ended up doing stuff around impact investing and working with foundations and university endowments to invest their money into more socially conscious things. That ended up giving me a little bit of a detour. I ended up going to San Francisco and working with a strategy consulting firm that specialized in nonprofits. And so I got placed with an education nonprofit. And that education nonprofit happened to also be a website—it was called GreatSchools. And so they provide free K to 12 data for parents and teachers and students and whatever to help them choose a school. I just thought that was really cool because they were just offering this information for free. They were just doing it because they thought it made sense. That was my first introduction to technology, through the nonprofit site. I saw technology as kind of a way to influence ideas more quickly than I was able to in nonprofit roles. I still felt like I had the same sort of goals and objectives as I did in nonprofit world. There are a lot of things that are so slow-moving when it comes to nonprofits, and with tech it’s just like, “You have an idea? You can get implemented. You can do it.” So that really appealed to me.

“Sometimes I feel like playing around in venture, and sometimes I feel like playing around in startups or whatever. But I want to be wherever the best place is for ideas to happen.”

Walk me through your next steps. You’ve done entrepreneurship. You ended up in VC. You’re working in open source world. Walk me through all of that.

I don’t really know how I ended up doing all sort of different things [chuckles]. I think after being at the education nonprofit, I left to start a company with my roommate at the time, because that’s what you do. It was sort of like me wanting to try my hand at something fun. I don’t think there is really anything deeper to it. I was learning how to code at the time and teaching myself how to code. It was fun and we kind of made something. I was super inexperienced. I remember when we made the website. I was like, “I think I can put a website together, maybe,” and my co-founder was like, “Sure. Whatever.” So it was just kind of like a fun project for us, that started growing into a business. And that was really exciting.

We went through the 500 Startups accelerator. We went into raising money, and kind of seeing how well-supported startups and venture were—and how well the ecosystem works. Basically, if you have an idea, there’s going to be capital out there to support you. No one is saying that startups don’t get funded enough. I think, fundamentally, it was just really creatively enabling to realize that you can do that. I kind of wanted to be able to provide that to other people too, right?

“I love the idea of being able to enable other people to be creative. I love the, just the idea of helping people be the most ‘them’ that they are, and just pulling out whatever is unique and special about people and really encouraging it. And so funding can be a really great mechanism for that because you’re enabling somebody to do something.”

So being on the venture side afterwards—we ended up selling our company to a food brand—because we realized cooking was not our lifelong passion. But it was fun.

So I ended up joining this venture capital firm. It was a lot of fun. I just started feeling really sucked into [chuckles] the machine of it all. And that’s not a knock against funders, it’s not even a knock against venture capital.

I think I’ve moved around a lot of different sectors because I actually didn’t really grow up thinking of myself as a creative person, but now people keep telling me I am, so maybe I am. In just the sense of I kind of want to do whatever I feel like doing. And so sometimes I feel like playing around in venture, and sometimes I feel like playing around in startups or whatever. But I want to be wherever the best place is for ideas to happen. And I felt like, with venture—and I think that’s why I’ve been drawn to the funding side, even with impact investing stuff before. I love the idea of being able to enable other people to be creative. I love the, just the idea of helping people be the most “them” that they are, and just pulling out whatever is unique and special about people and really encouraging it. And so funding can be a really great mechanism for that because you’re enabling somebody to do something. But, I think they’re—it sounds like that on paper with venture, but it doesn’t always work out that way.

And right now, working in open source and basically I’m trying to help people understand a lot of the risks and problems in supporting open source infrastructure right now. And the best part about it right now is being able to work with really, really creative people all the time. I love hearing people’s crazy stories. I love hearing how they’ve had to grapple with other people. I think the coolest thing about open source right now is that it is just—it all comes down to community and working with people and there’s nothing you can really automate about it, it would just never work. So you have to learn how to talk to people, you have to learn how to get along with lots of people and make it all come together somehow. So I feel really happy just being around creativity and feeling enabled and validated and all that.

“I think the coolest thing about open source right now is that it is just—it all comes down to community and working with people and there’s nothing you can really automate about it, it would just never work. So you have to learn how to talk to people, you have to learn how to get along with lots of people and make it all come together somehow.”

Let’s back up. Tell me more about what it was like being a lady entrepreneur. Being part of that world, fundraising, eventually selling. What was that experience like?

I wasn’t doing most of the fundraising so that made that part easier. [laughter] It was actually kind of funny. I was the person building the products and people would always go, “Oh, you’re a female coder!” or whatever, which was sort of funny, but I guess worked to our advantage because it was a positive expectation for people. The thing that bothered me about being a founder was that if I told people that we had a food company, they would always assume my co-founder was female and they would just be like, “Oh, women, food. Makes perfect sense. Women do fashion companies and food companies and stuff,” and I never thought of myself as that—it was just something that we wanted to do at the time and it was just like, “You’re my roommate,” you know.

“I was the person building the products and people would always go, ‘Oh, you’re a female coder!’ or whatever, which was sort of funny, but I guess worked to our advantage because it was a positive expectation for people. The thing that bothered me about being a founder was that if I told people that we had a food company, they would always assume my co-founder was female and they would just be like, ‘Oh, women, food. Makes perfect sense. Women do fashion companies and food companies and stuff.“‘

I felt like I was being forced into some sort of weird stereotype that I didn’t really identify with. Yeah, actually, I really love cooking, personally. I still do, but it doesn’t make me womanly, that I like to cook. There are plenty of guys who like to cook. It was just this weird pushback against my gender. The same thing happened in venture, where everyone calls you a woman VC. I was like, I don’t want to be a woman VC. I just want to be an investor, like anybody else.

It definitely has its advantages. I have no way of proving this, but I felt like it was easier for people to open up to women in a one-on-one conversation. At least, I found that I would learn things very quickly, like really personal stories, about founders that I talked to. That was cool. Then on the other hand, there would be boundary crossing with other investors in other firms, or with founders I talked to, where it suddenly gets a little too close, and it’s like, “I don’t know how to manage this.” I feel like there’s always this adjective being attached to everything I’m doing, that’s like, “You’re the female.” Like, “So cool. You’re a woman.” I’m like, “Yep, I’m a woman. I don’t really know what else you want me to say.” I only want to do things that feel really natural to me, so this stuff feels really natural, and so that’s why I do it. It feels awkward when somebody retroactively puts this adjective on me that I don’t even feel like I identify that strongly with.

“I don’t want to be a woman VC. I just want to be an investor, like anybody else.”

You brought up that you downplay your gender in the workplace, which I could totally relate to when I worked in tech. I am so much more feminine—I’m still not super-feminine, but I’m so much more feminine now as a photographer who works for myself than when I was in tech.

It’s odd because sometimes I don’t know whether I feel like I don’t identify that strongly with the woman label because identifying with it would downplay my own power and influence, or whether because I truly don’t identify with it. So it’s like a really odd thing to manage. I make a point to wear basically the same thing all the time.

“It’s odd because sometimes I don’t know whether I feel like I don’t identify that strongly with the woman label because identifying with it would downplay my own power and influence, or whether because I truly don’t identify with it.”

All black? Yeah me too. [laughter]

Just dress down, like don’t wear anything that’s too form-fitting, err on the side of pants and sneakers and stuff. People joke around with me about it. I’m like, “Honestly it makes a difference.” It makes me feel like when I talk to people they’re at least not looking at my body or something. It’s sort of weird that we have to do it. But I hate being looked at. I think that’s why I prefer writing to speaking, honestly. Or just being behind a screen. Because then I feel like people are paying attention to my ideas instead of my face or what I’m wearing or whatever.

“I hate being looked at. I think that’s why I prefer writing to speaking, honestly. Or just being behind a screen. Because then I feel like people are paying attention to my ideas instead of my face or what I’m wearing or whatever.”

I totally get it.  Have you experienced in the same way that I did, people making assumptions about why you were even around, in a networking sense, at events or things like that?

I haven’t had anyone say that to my face, thank goodness. But definitely a lot of the—I’m standing in the circle with a bunch of people, and all the guys get asked what they do, and the woman is just assumed to be, “Oh, she’s probably someone’s girlfriend.” Even if the conversation is highly relevant to what I’m doing, I jump in and make comments about the ideas like anyone else would. And they kind of just look at you like, “Oh, that’s cute,” and keep talking. The most validating time, I have to say, to have this happen was being in VC. Because when you say the word VC, the mic drops and everybody’s like, “Oh my God, you have money.” Which I thought was just funny because people’s tones would just change completely when they realize that. And I’m like, “Yep. You probably shouldn’t do that.”

“I’m standing in the circle with a bunch of people, and all the guys get asked what they do, and the woman is just assumed to be, ‘Oh, she’s probably someone’s girlfriend.’ Even if the conversation is highly relevant to what I’m doing, I jump in and make comments about the ideas like anyone else would. And they kind of just look at you like, ‘Oh, that’s cute,’ and keep talking. The most validating time to have this happen was being in VC. Because when you say the word VC, the mic drops and everybody’s like, ‘Oh my God, you have money.’ Which I thought was just funny because people’s tones would just change completely when they realize that. And I’m like, ‘Yep. You probably shouldn’t do that.'”

What was the impetus for turning your attention to open source and giving back to the industry in a way?

There were a lot of things. My story changes a little bit every time, because it honestly was a lot of different reasons. I think that, honestly, I was feeling a little bit burned out by venture. It was truly the most fun and the most hard job I’ve had so far, but after I left I really thought about, “Do I even want to be in tech any more? Like, I should just go.” Like, “Fuck this place.” And really thought about moving out of San Francisco. Really thought about whether I just want to do something completely different. And even experimented and talked to people about it and really gave it some serious exploration, and in the end I realized, “I actually love technology.” Like, there’s a reason why I came into this sector. I really, really, really, really love it. I could not picture myself anywhere else. And that comes with all these other strings attached, but I love being here. And so I kind of had to find, “What is it that I still love about it that can make me happy?” And I realized that chasing after the next unicorn or trying to get into the next hot deal is just not fulfilling for me. And I think it required a lot of mental adjustment, too, because you get told—when you’re in the startup-venture binary—being in venture is like you hold the purse strings; you have all this cachet and people invite you to things and people think you’re important and whatever, and so you get this false sense of status which is kind of ridiculous. And it felt weird to be like, “Why don’t I want this”, or like “Why doesn’t this make me happy?” It took awhile to just let that go and say this is not where I want to be and if I do this I’m going to be really unhappy and I want to be around things that make me happy and so it just started with like, “What can I do that makes me happy?'” and like “Where do I want to be?” and that’s how I ended up here because once I started talking to people in the open source world, I just felt really happy. I felt really at home. I felt like people understood me and my mindset and I wasn’t feeling like I had to defend this core sense of identity all the time so, yeah, that’s why I’m here.

“There’s a reason why I came into this sector. I really, really, really, really love it. I could not picture myself anywhere else. And that comes with all these other strings attached, but I love being here. And so I kind of had to find, ‘What is it that I still love about it that can make me happy?’ And I realized that chasing after the next unicorn or trying to get into the next hot deal is just not fulfilling for me.”

What fatigued you on the industry during your time either as an entrepreneur or a VC?

Many trends over time, and there was plenty of good stuff too. I still feel like I have great friends in the industry. I just felt fundamentally not like me, which was like this gut feeling. I felt like there were constantly people around me telling me I had to be a certain way that I wasn’t and I guess I actually didn’t really realize how feminine my outlook is, if you can call it feminine.

In VC for example, people talk about, “Are there enough women in venture”, and they talk about discrimination. I actually don’t think the discrimination is that obvious. It’s not really about, did someone make a sexist remark at you or something, but it’s more of, I feel like my point of view was just not compatible with venture. Where venture is highly, highly competitive, and it’s about bravado, and I don’t know, just posturing, being something you’re not, whatever. And this is true with founders too, I think. I’m super, super cooperative, I like finding ways to bring everyone together, and let’s work towards a solution. I’m really inspired by multiple sectors, and how do nonprofits and for- profits work together. Like venture and foundations. And so I love just thinking across a lot of different things, and I felt like that was just not a point of view that was appreciated. Even with startups, it’s like, “execute execute,” “hustle hustle.” And then just, aaahh, I just want to—it was so binary for me to think that way, and I think very fluidly. And there’s trade-offs for both, but it’s just I think I felt burnt out over time, because I felt I was being forced to be this binary supercharged hustler. It’s like, “That is not who I am, and is that okay world, if I’m not?”

Did you have early support networks when you came here, and where do you find those now?

Yeah, that’s a good question. Nobody has asked me that.

I did not really know anybody when I moved here. I had one friend from Tufts who I didn’t know super well but we’re now really close friends. I had a couple people that I knew through this fellowship that I was doing when I moved out here, and cobbled together a friend network from that. Those people ended up becoming my closest friends, so I felt supported in that way. And my partner, who’s my biggest source of support and positive influence in my life, he came out of that circle of friends, too.

In terms of support network for tech, it happened slowly and over time. I’m trying to think back. There were a couple people that were really, really useful and supportive early on. Literally, a couple. Anything I knew that I wanted to do, probably came from popping into a network of sorts. When I learned how to code, there weren’t a whole lot of bootcamps or courses. It was still a fairly opaque process. I joined the Women Who Code group in the meetup here, and it just gave me such a safe space to do something that was so intimidating. I’m so thankful for Women Who Code. Just having people around you who are willing to be helpful, and sharing resources, that was just very helpful, to tap into something where by tapping into one thing, you’re connected to a whole bunch more stuff. Then with being a founder, 500 Startups helped tap into a certain network as well. I think that’s probably the benefit of accelerators for a lot of people. It’s like, “Oh, now you’re part of this network and part of this family,” or whatever. Then with doing VC, I think being at a fund that already had a great reputation was so, so helpful. People would just be like, “Oh, I know your partner,” or, “I know your investments.” And like, “You guys are a great fund,” and whatever. That’s like the ultimate tapping into a network. VCs are everywhere. That probably expanded my network the most.

I’ve never been great at asking people for individual support, like one-on-one support. People will make fun of me for it. I kind of suck at finding mentors and whatever. But I just try to be nice and make friends. Trying to give as much as I can is—I know it sounds like everybody says it, but—when you do that a little bit, it ends up coming back and helping you. I just try to take a really—and there have been some friends of mine who have really influenced my thinking on that, of just being like, “Give, give, give! Be super, super, super fucking nice,” and like, “Never give anybody a reason to hate you.” That works really well. I guess I never really thought of myself as a super social person or like a networky kind of person. I think of myself as actually sort of antisocial, but then all my friends are always like, “You are the most calendered antisocial person I know.” So, I don’t know. It sort of happens, I guess. I try to be nice and friendly, and stuff just sort of comes my way that way. I wish I were better at asking for help though.

“I’ve never been great at asking people for individual support, like one-on-one support. People will make fun of me for it. I kind of suck at finding mentors and whatever. But I just try to be nice and make friends. Trying to give as much as I can is—I know it sounds like everybody says it, but—when you do that a little bit, it ends up coming back and helping you.”

No, I’m exactly the same. You can probably relate. I had no money or power in tech, so my currency was social.

Yeah, totally.

I would intro people to people, or I do favors for people, or whatever. I would do anything for people because it was free, and that’s like literally how I built my value in tech.

It’s actually a funny mindset. I used to, like, literally—“I will help you with whatever, just let me help you.” Now I have to think about, “All right, what do I actually need to say no to, to manage my time better”, and it’s been a funny mindset to transition out of, or like, scale out of. Because I really want to be helpful to everyone. But, oh yeah, I can’t just go and do 20 different projects. I need to do the one that I want to do. But I think it’s like—it has felt that easy to just sort of be helpful wherever I can. But to look back at it, I feel like, “I don’t know how all that worked out.”

Yeah, if you haven’t read Essentialism yet, it’s probably a good time in your life to read it.

Oooh.

It talks about the paradox of success and how we became successful because we had this vision, and we work super, super hard and we’re opportunistic. So you get to this level of success and then you suddenly have a million inbound options and opportunities to choose from. You have people who want to work with you, people who have cool projects for you, job offers, people who want to get coffee with you. An you’re an opportunistic person, and you want to be helpful so you want to do all those things, but then you end up stuck at this plateau because you’re busy, your energy’s now distributed towards addressing all of these options and opportunities and then you forget what you’re even going for in the first place. It’s a great book, would recommend.

That actually describes my life right now. I need to read this.

I always have a copy at my house, so when you come and take your picture I’m probably just going to send it away with you.

Yay. [chuckle]

What are your biggest motivators? What drives you?

What drives me? I really believe strongly on the power of creativity in individuals and to unlock that underlying ability. I know that’s super cheesy but it’s just so true. When I think about everything even in my personal life, like my personal interests, friendships, relationships, everything—it’s all about enabling some personal weirdness about myself and other people. If people feel like they can’t be really them, how can we make it so that people feel comfortable? I love one-on-one conversations with people because it’s just a matter of kinda drawing all their stories and, how do you do that to hopefully get them to open up? It makes me happier than anything else in the world. I’m very story driven. I just love hearing things that are different about other people, getting other people’s perspectives. Its why I love doing what I’m doing right now, because it’s tons of weird stories and you have to talk to people and earn their trust and then they might open up to you. Everything I do, I want it to be around that.

That’s awesome. It’s like what I tweeted like a week ago or something. “There are extroverts and introverts, but there’s need to be a word for people who get their energy exclusively from one-on-ones.”

Yes.

I am that person [chuckle].

That’s a word that’s really hard to scale a time to, because I love meeting people even if it’s somebody that in the end there’s no real way for us to work together or whatever. I just love sitting there and listening to them. Like, “That’s awesome, tell me more” [chuckle]

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

My mom has been actually super awesome and supportive. Both my parents have been really supportive. I wouldn’t have thought they were going to be when I first graduated and everything. My dad is always super, super encouraging—motivating me to “do what you need to do.” He’s always supported all my weird travel adventures and everything.

I remember when I first told them I wanted to start a company with my roommate. They didn’t know what was going to happen, but they were so, so, so supportive. Then I went to VC and they were really supportive. They’ll send me articles, right, because they’re my parents. The articles will change depending on whatever I’m doing and they’re researching all the time, which is so nice of them. My mom—when I told her I wanted to do open source stuff she’s like, “I don’t know what this is, but I’m reading about it all the time.” I was like, “Oh my God. You’re reading about open source? What? Do you even—even my friends here don’t know what it is.” It’s been really, really awesome to have that level of support from my parents. And with friends—I think the friends I keep over time are friends who understand my kookiness a little bit. Even within tech and stuff. So they’ve all been really great and supportive. I think that’s one of the most important things is: just having people around you who believe in you.

Yeah, for sure. How do you feel about the state of tech in 2016? What excites you, even particularly in open source? What frustrates you?

I’m so curious what is going to happen in the future [chuckles]. Everyone is obviously talking about—I don’t want to say the word, but—bubbles. But it’s kind of funny, so the short time that I was in venture, was apparently, now looking at the charts, one of the peak times in spending, so no wonder I thought it was fucking nuts, and last quarter, spending dropped like crazy. So, I can’t tell from the outside necessarily what is going on, but my friends I’ve talked to have said yeah, we’re investing way less, we’re examining things a lot more carefully, and so it’s kind of like, man, I wonder what it’s like to be in venture now. So, yeah, but I think, my theory is, it’s very hard to think long term about an industry that has a short history. My theory is the world has periods of high high growth and periods of figuring out how to sustain that growth, like grappling with whatever we’ve done. And so maybe right now we’ve passed through the hyper hyper growth periods and now we’re thinking about how to sustain things, and so, I mean, there’s plenty of politics around all this stuff, but there’s more talk about nonprofits and funding long term research and partnerships and initiatives that are reaching across certain sectors, and we’re talking about basic income and it’s not a joke anymore. That’s so cool.

“It’s very hard to think long term about an industry that has a short history.”

I’m really excited about maybe potentially we’re entering this time where people are thinking a little bit more around sustainability and ensuring these long-term things are around, that we can help fund creativity. I feel like creativity itself has been so validated as the power of the individual to make significant contributions which is why stuff like basic income doesn’t seem crazy. I mean it should be crazy. I think it’s just so funny that people are into basic income because other things sound like socialism or communism to them but then it’s like, “Oh, no, basic income is great,” and it’s partially because we believe in people. I think it’s a really cool time right now because that’s what I believe and I really hope that more people invest in it and care about it.

The one thing that bothers me right now or feels weird is just all politics and conversations getting more polarized than it was before, and I’ve definitely noticed this about diversity conversations in tech, where I can’t even take part in them. It’s just really frustrating because I think that there’s two philosophies around diversity. One is around hyper-polarization and separation into different shells, like, “I’m black and you’re not,” or, “I’m a woman and you’re not. You can’t understand me. You can’t possibly understand me.” That’s one school of thought and the other school of thought is more around things like unconscious bias where it’s like, “We’re all sexist. We’re all racist.”  We’re all scared and vulnerable and know what it feels like to be rejected on whatever level, and so use that as a uniting, empathic connection. Obviously, I resonate more strongly with that camp, and I feel like it’s missing from the conversation around diversity, because diversity can be all about highlighting what makes you different from others, or it could be all about highlighting what’s common between us. I really hope that is part of the conversation. I’m not very optimistic that it is and that makes me kind of sad.

“I think that there’s two philosophies around diversity. One is around hyper-polarization and separation into different shells, like, ‘I’m black and you’re not,’ or, ‘I’m a woman and you’re not. You can’t understand me. You can’t possibly understand me.’ That’s one school of thought and the other school of thought is more around things like unconscious bias where it’s like, ‘We’re all sexist. We’re all racist.” We’re all scared and vulnerable and know what it feels like to be rejected on whatever level, and so use that as a uniting, empathic connection. Obviously, I resonate more strongly with that camp, and I feel like it’s missing from the conversation around diversity, because diversity can be all about highlighting what makes you different from others, or it could be all about highlighting what’s common between us. I really hope that is part of the conversation. I’m not very optimistic that it is and that makes me kind of sad.”

How do you think your background and life experiences impact the way that you approach your work and what you want in work?

Hyper-collaboration [chuckles]. I just believe that positive communication is the key to everything. Or people just being able to trust each other and be vulnerable with each other is the key to everything. I think that maybe is why building support networks and stuff doesn’t feel unusual to me, because it is just a natural part of that—of building trust with somebody else. You honor them and their willingness to trust you, and you expect likewise. I think that’s just a really powerful currency and a way of just communicating with people and making people happy. It’s the most, most important thing of anything I do with work. Making sure that I have other people’s trust and confidence and that I don’t ever violate that. That people feel welcome and included and no one ever feels shitty because I think those emotions are so universal. Everything we do can kind of be boiled down to, “Do I feel shitty and rejected for who I am, or not?” I’ve felt that in so many different ways growing up and I never want to inflict that on anybody else.

“Everything we do can kind of be boiled down to, ‘Do I feel shitty and rejected for who I am, or not?’ I’ve felt that in so many different ways growing up and I never want to inflict that on anybody else.”

Sounds like a very good quality for a founder or VC to have.

Yes, or a person.

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

Maybe. It’s hard to plan that far ahead. I’d like to be a little more flexible, and travel. But this still feels like my home for sure. I don’t know. I really suck at thinking far ahead for anything. [chuckles] I kind of just think ahead to like the next year. As long as my bills get paid, and I’m having fun every day, then I know I’m in a good place.

What about this year? What are you like working on either yourself or for work?

Right now it’s kind of a funny—I never really know how to explain what I’m doing right now, because I’m basically being supported by a foundation to bring more transparency to an issue that’s really important to technology. So I see sort of like the first half of this year just kind of being around getting people together, getting them talking, writing about open source so that it’s accessible. That helps bring some of those stories out of just within their communities and more to other people who might not have heard them. So that’s like a really important part of it. The reaction has been so much stronger than I expected. That’s a really positive thing. I feel like now it’s kind of time to also start thinking towards how can I help support that stuff long-term. So thinking through like what would an organization look like that can help support and sustain, or just be a resource to people in those communities who need support or need help and there’s nowhere really like that right now. I think that’s the fun part that happens next as people get excited and engaged. The question is, “What do we actually do about it?”

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

I’d say, “People are just your best resource.” I think that’s especially true in tech. And it’s especially true in Silicon Valley tech more than anywhere else.

Where people are just so willing to help in this industry maybe more than anywhere else. I haven’t worked much in other industries but it just seems like it here. So if you don’t know how to do something or you want to learn how to do something, just cold email people and say hey. Or go attend an event and introduce yourself to people. Don’t be afraid to ask for help and then also give as freely as you receive. Honestly like 90% of the work is just be nice and help people.

“So if you don’t know how to do something or you want to learn how to do something, just cold email people and say hey. Or go attend an event and introduce yourself to people. Don’t be afraid to ask for help and then also give as freely as you receive. Honestly like 90% of the work is just be nice and help people.”

I was born in South Africa. I was born in Soweto, which is a township in the Johannesburg area. And I was born there in the ’80s which was a very tumultuous time to be born there. The height of the armed resistance against Apartheid. My mom went to Soweto to have me from Botswana, which was where she was living with my father. My father was in exile at the time and so he couldn’t come in to South Africa. So the first couple of weeks of my life it was just me, mom and the grandparents. But then ended up going back to Botswana and was there for a little bit. But the circumstances worsened quite precipitously and it got very violent and a number of people were killed in our immediate circle, and my parents decided that we needed to leave, so we came to the United States.

Wow. Where’d you land?

New York City. JFK [chuckles].

What was that like for you?

I don’t know.

You were still tiny?

I was tiny. But it was a rough-and-tumble couple of months there. It was a thousand bucks, and the Hebrew International Aid Society was an organization that took us. They and New York Association for New Americans had been taking refuges obviously for quite some time, and they were just great to us. They saved us. We lived in the Latham Hotel, which was a homeless shelter. We were on food stamps, and jobless and penniless, and all that. My mom ended up getting a job as an ESL teacher at Fashion Institute of Technology, and my dad got a job as a cashier and coat checker at the Museum of Natural History. That was actually 30 years ago. 30 years ago in April is when we landed. Then my dad eventually became a teacher at a public school in Queens. And my mom became a permanent substitute at an elementary school. They were both teachers, and we eventually got an apartment in south Bronx near Jerome Avenue. You could hear Yankee stadium. Dad didn’t know what a baseball was, but he loved cricket, so we ultimately ended up going to some baseball games. We even saw the Yankees coming out of the stadium once, when  after a game and my dad met Reggie Jackson was the Yankee at the time. He ended up getting the tickets, so he’s a lifelong very big Yankees fan.

What was it like being raised in New York but in a family that’s not from New York or not from America?

That’s a good question, but it makes me realize I should tell more of the story. My parents were both trained as educators and they’ve been teachers in Botswana and in South Africa with my mom. They ultimately had heard from a fellow teacher at Maru-A-Pula in Botswana about a school called Milton Academy in Boston. My dad was doing some research and he ended up applying for a job at a school called Phillips Academy in Andover, Massachusetts. We drove up together, the whole family. They offered him the job, and we made the move. So I grow up in Andover, on an idyllic tree lined, prep-school campus as the son of a chemistry teacher.

Wow. That’s a change.

So maybe the question that you haven’t asked that is the interesting one to answer is, What’s it like going to and growing up on a fancy prep school campus while being eminently unfancy?

Yes.

I don’t know what it would be like not doing that. So I can’t really answer the counterfactual to it. But it was really wonderful. I learned English in preschool and I had learned Spanish in New York. Spanish was actually my first language. And then Xhosa, which is my sort of family language, was my second language. So I was speaking this very odd mix of the three when I got to preschool. The teachers were like, “Wow, it sounds like Spanish but he’s clicking.” It was funny. It was wonderful. I was the only black person in my class often. Sometimes there were two. So I learned to translate. I got really used to people wanting to play with my hair. Wanting me to, “Say your last name. Say it again. Say it again. Say it again.” And and I became fluent in the language of suburban affluent white America, but fluent in it knowing that I was never part of it. So I remember there was a moment when I was probably six or seven, where I was thinking about Ronald Reagan, because he had just been President. I had a panic moment because I was like, “Ronald Reagan was President and I don’t think I can be President because I’m black and because I wasn’t born here and because I have a funny name [chuckles].”Two out of those three are no longer thoughts that a six-year-old would have in those circumstances, which is pretty great. I had numbers of moments like that where I was just like, “Wow, I’m really not one of them.” And so it was always a little bit disorientated, especially because my parents being activists and civil rights activists particularly, always instilled in us a very, very strong sense of self and a very acute and intimate sensitivity to racism. So it was something I was always thinking about, and it was ever present. When I got to college and people like, “Oh. You went to Andover?” And it’s like, I’m a lot preppier than you think because I actually grew up on the campus but I’m a lot less preppy than you could ever understand, because of all the other stuff. And so, it’s just weird to be a third rail kid. To have a foot on both sides of the ocean.

Yeah. That’s interesting. What did you think you were going to be when you grew up? And did you have family pointing you in any particular direction?

I thought I was going to be the president until I was six. And then I thought, “You know what? I might still be able to.”

And then, later, I wanted to be a lawyer. And then I wanted to be a diplomat because my—I have diplomats in my family. So, I knew about it—I learned about it early. And they’re like, “Speaking multiple languages helps.” And I went, “Okay. Great.”

When I got to college, however, I wanted to be a chemical engineer. My dad was a chemistry teacher. I was his student in chemistry. I was a very disciplined and conscientious chemistry student. And so, when I—and I even weighed the quality of the chemical engineering as part of the decision matrix for choosing my college. So, I really wanted to be a chemical engineer, or so I thought.

Yeah. When did that turn?

When I hated college passionately.

Me too.

Really? Hooray! I hated college so much. There were a couple of reasons. One thing I always say somewhat jokingly is if you are a drop out of Harvard or Stanford you must be a genius, but if you’re a drop out of a community college you must be emotionally compromised somehow. I was actually just emotionally compromised, not a genius. I hated college because it was very lonely. I was black but not black American in the sense that I didn’t have the shared history and I didn’t grow up in a black American home. I grew up in a black home in a America. So that was a very strange thing that I couldn’t navigate and so finding my people was a little disorienting on that basis. I was preppy but not wealthy. I was African but not Nigerian. That was just from the social side I was very isolated. Academically, I hated engineering and I had gotten about half way through it and then I just stopped. I switched to philosophy, and thought that philosophy would be a very purely intellectually stimulating pursuit, and I was sorely disappointed by that too. I ended up dropping out and it was a pretty shameful dropout, but I remember that—I realized that most of the people who were at school were highly intrinsically motivated self-starters with working parents with graduate degrees and per capita incomes of $250K and greater, and so they needed Stanford degrees. The notion of it being the best school was really that they selected people who were already going to be okay, and I found that also to be really distasteful – like it was such a—it felt like it was finishing school for the already successful, which  got me really depressed.

So, I dropped out.

What happened after that?

We did a startup, naturally. That’s the thing about Stanford. I will say, 2003, four, five, startups were, compared to now, they weren’t on anybody’s radar. But a guy at the business school was working on a project out of this class, Formation of New Ventures, which was taught by a VC and, you know? And he and I crossed paths and he was like, “You should come work for me on this.” And he asked me to do it because I had a lot of Facebook friends and, at that time, that actually meant something [laughter].

And so, and he was working on a product that was oriented towards the demographic that I had the connection to which is the young professional types. And so, I agreed to work for him. And so, I came on as a very early employee and in very short order we raised some capital and I was launched into the tech world.

I’m curious what your impressions were, or maybe even preconceptions of Silicon Valley, and whether or not they lived up to your expectations.

I didn’t have a ton because I was interested in science and engineering, so not really in technology per say. Certainly not in business innovation, and so I didn’t come in with any sort of presumptions particularly. What I will say I was surprised by, and only recently I was stopped being surprised by the fact that it’s a human capital business. It’s a people business and people tend to have insular networks. It’s very much a people business with a lot of instinct and gut and those types of things tied to people. It’s not that accessible surprisingly. I would have thought, and there was a brief period where I did think it was ridiculously accessible. It’s funny because it should be the most accessible place in the world. That is, I think, a preconception that I was disabused of. The other piece is venture is even more intensely that way… Times a thousand

Walk me through the startup chapter of your life when you were in it as an employee.

Oh, boy. I think we accidentally picked up the anti-startup handbook [chuckles]. We were building in PHP. I think we were building in PHP because Facebook was but no other real reason. All of the engineers we knew wanted to build on the Ruby framework or rails framework and we hired a series of executives and we outsourced to Russia non-thoughtfully. We had a hierarchical culture that emerged relatively quickly. We’re dealing with some intense cultural stuff. It was chaotic. It was intensely chaotic. In retrospect we were on the verge of going out of business for six months and I was naive and didn’t quite realize it at the time because it is a momentum thing. When the momentum was good you feel awesome even though you’re spending other people’s money and you’re lighting it on fire, basically. That was intense. The high highs and frequent lows were also a feature in that chapter of startup life. In part because I was also just not in a very good state. It felt like I had failed, in fact. I think it’s safe to say I had failed, in the sense that my parents were deeply disappointed and concerned about my state of being, and my peer group didn’t really understand me, and they thought I was sort of flailing in the wind, and I felt a little bit like I was. And this cult of failure that people celebrate here is  because failure just sucks a lot.

There’s plenty of failure out there. It’s not hard to find. And when people here talk about failure, they’re actually talking about success, and they’re talking about overcoming failure, which is all well and good but celebrating failure is something that is a pet peeve of mine because of having felt like I was fully failed. And we were able to sort of land the plane on the startup and get an outcome for it, and exit the business in a way that we were licking our wounds a bit, but it’s still alive. But it felt like a failure, and these outcomes feel so binary here, where if you’re not on the, “Oh, my god, this is it crushing it” track, you have failed. And that just really hurts. It’s so defeating. It’s so de-motivating. And the piece that I find motivating is not when I’ve failed, but it’s believing that there’s a chance that I can eventually succeed [chuckles]. A promise of success is what’s motivating me. So that period I try not to think about that much, and I’ve managed just like we all have to retroactively tell the story very neatly. Like, “Oh, like 300,000 users and a Series A!” But the truth is the matter is I was just sort of lost and confused, and we were making not excellent decisions with this startup, and I didn’t know my ass from my elbow, and so it’s been clear to me, if I even was value add, even though the founder kept me on—so it was not recommended. People have asked me. It’s like, “Oh, should I drop out of school, because you did?” “Don’t. Please don’t.” It sucks. It’s so lonely, and it’s discouraging and it’s so embarrassing and shameful. Don’t do it, you know? And not enough people, I think, are talking about that, so.

You touched on otherness growing up. Not feeling like you fit in with white kids. Not feeling like you fit in with American black kids. Did you feel that otherness when you worked in startup land?

Oh, yeah. The otherness–if I had to characterize the feeling in one word, it would be poor [laughter]. And I hear people say, “Just boot strap it.” It’s like what does that mean, you know? My credit score got crushed because I wasn’t sophisticated about that and my parents, they didn’t know a ton about that stuff. And so, they hadn’t really given me all the lessons. I didn’t have a nest egg. I didn’t have savings to speak of. I didn’t have aunts and uncles who could float me five, ten K to say nothing of the 50, hundred K’s that people get. And yes, of course, there’s cultural stuff. And there is gas lighting and feelings of invisible racism and other isms that are manifesting in conversations and manifesting in the challenges I encounter when I access certain networks but when the truth—when push comes to shove, not having as much money as everybody else around me was by far the biggest feeling of othering or otherness.

Me too. Yeah. I remember going—and no one knew this but going to all of my friends’ millionaire houses and partying with them and then going home and eating my pocket ramen like every night and being like, “Fuck. Am I the only one in tech living like this?” 

And poverty’s expensive, you know? It kicks you—it has a cognitive toll and a physical toll and it’s really hard to keep pace in a fast-moving environment when you’re also trying to navigate your personal finances. And it’s hard to do that I remember, I said to somebody that I’ve never been to SXSW, because when I was a broke, startup person, whether I was an early employee, or later a founder, I just didn’t have the money to fly there. That’s why I didn’t go. Now it’s like, “I didn’t go, because I’m way too cool for it.” No, I just was poor, and you were not, because your aunt gave you money. People might be surprised by how often people outside of the dominant demographic just don’t have financial access. Just disproportionately, don’t have financial access, and therefore, our risk calculus and the way we navigate this world, and how we spend our time, has to be different, because there’s some stuff we can’t afford to do. Ski week? Fuck off.

Yeah. That tweet storm that went around yesterday, the YC guy, I was looking at the replies, and I saw one guy’s reply just be like, “Did you ever consider not taking funding?” I’m like, what a silly assumption. To assume that it’s possible for him to just bootstrap it. With what money?

Now that I’m on this side of the table, I’m guilty of this too. Come back to us when you have some traction. Why don’t you raise a friends or family or an angel round. a.k.a I assume that you are in your first degree connections, in a world of millionaires. Which is a horrible and stupid assumption, and is incorrect and is wrong.

I make the same assumptions, even as someone who wasn’t a rich person here. I still assume that everybody else is.

There’s also this weird duck syndrome thing too, where we’re part of your credibility and your ability to make moves in this network is fundamentally tied to a money thing. You have to hang and so you have to fake it. There are plenty of people I know, and I was one of these who were furiously paddling under the surface just to cruise. Just to have the right clothes, just to have the right gadgets. I was on a dumb phone for too long because I couldn’t afford a smartphone because my parents weren’t rich. We came here with nothing. In America, where people of color are disproportionately in less wealthy networks, that just means that money is a barrier. Period.

If you want to touch on being a founder, we can do that, but walk me through, from that first experience, to getting into VC. Did you have any idea that that would be the path?

No, I’m on record all over the place, saying I’d never be in a VC. I had a view of VC, that they were just … Also deep down, I felt too poor to ever become a VC, so that was also driving it. I also just had a view of VC as Menlo Park, khakis, Princeton, MBA. I didn’t feel like that was the person I was growing into. Turns out, that’s what VC’s are, which is fine. At some point, I worked for Obama’s campaign. He was my people obviously and I was so drawn to him spiritually and then politically and culturally. That was a defining experience for me, maybe the defining professional experience for me because I remembered that I came from a line of people who were very politically motivated, not in the sense of ambitious in elected office, but who were civil rights activists and from my father to my mom’s father and my father’s grandfather and it’s all an investment in the future — in mine and my generation’s lives. I felt like that was something that was important to me that I had forgotten in the rat race of Churn and MRR and valuations and tech conferences and shit and so it reminded me that the only work that I really felt was worth doing over the very long term had to have some political point of view and had to be positive social results and that stuck with me since and has changed the way I felt about business. And that deepens the more I learn about our economy and my view of capitalism. So that was awesome, like, introducing Michelle Obama on election eve, which was just wild. Then, after working on some startups, I realized that I wanted to repair the relationship with my parents and then went back to school.

At this point, were they super stressed about you?

Yeah, they were used to it, but there was a constant hum of stress that had been following them for years. I knew it, and I could hear it, too, so I had it, too.

What was it like, going back to school?

Best decision of my life. I met my wife. I met my wife, and I also got involved with the d. school, and started really enjoying some of the philosophy work I was doing —actually continued into graduate classes and began a thesis on the theory of intention, which I still find fascinating.  But instead of finishing a Master’s, I ended up dropping out again to join Collaborative Fund. But it was great to be, you know, learning environment, having lived, having done a couple startups, and been in different parts of the world, and been around poverty, and been around extreme wealth, and just seeing stuff, you know?

What have been some of the toughest parts of your work?

Toughest parts of the work. Well, VC is not–being a VC is one of the best jobs in the world so it’s hard to complain about it. I truly love it. And, on some level, it doesn’t feel right to complain about it but if I see fifteen hundred companies in a year I usually make six investments. And so, I’m in the business of saying no. And I’m a dream crusher. That’s my job. And “you are what you repeatedly do”, it’s been said, right? And so I crush dreams. And that is trying. It never gets easier. And because somebody will have such an amazing story. You can just see blood, sweat, and tears all over their product and you can see that they’re just hungry – physically and spiritually – and you have to say, “I don’t like your brand. it’s just so crappy. The hardest part about that, too, at the earliest stage, because there’s no data, is, I can’t say it’s not personal. It’s personal. That’s all it is. It’s not just, really hurt the people. I totally understand it, and some people get really offended, and take it personally, as they rightfully should. Doing that every day, just doesn’t feel good. Having to find a way to do that while also maintaining one’s reputation, because as a VC, your personal belief in your firm’s brand is all you have. If we have to disappoint people all day every day, and still maintain a good reputation, that’s a tough nut to crack. Finding ways to say no to people, such that they’ll say nice things, is a weird thing to have to do every day.

In this project the idea has come up that VCs are interested in investing only in problems that they can relate to. What are your thoughts?

Yeah, well, one of the things that I’ve caught myself doing, and I’m ashamed of, and I don’t do it anymore, or at least I try not to do it anymore is I’ll see a feminine hygeine product, and I’ll think, oh I don’t know anything about that market. But then I’ll see a construction management software, and I’ll think oh, that’s interesting. Which is crazy behavior and is deeply sexist behavior. And probably misogynistic behavior because tied to that is: I don’t want to know anything about X, Y, or Z. And that is dark. And I’ve caught myself doing that. And I’ve caught myself, also, meeting with an entrepreneur from Paducah, Kentucky and, on the basis of that person’s accent, making judgments about their likelihood of being an effective engineer. I’ve caught myself evaluating somebody’s watch or effective—maybe Spanish was their first language and they have slightly darker skin and then discounting the quality of the design of their product. Just stuff like that. And–

Interesting considering Spanish was your first language.

I know, right? Yeah [laughter]. And I am somebody who’s trying my hardest to actively avoid these unconscious biases. And so, Lord help the rest of the industry. And yeah. Lord help the rest of the industry. It’s so tough. And there’s so many companies that, if you are a 26-year-old heterosexual white male living in a city, you are their target customer. And one thing that’s funny about VC is most VCs are old, too, and don’t live in cities. And so, that’s not even their experience.

And I think it’s we invest in people who we recognize. And because ultimately this is a human capital business and the signals are instinct and gut driven and your networks are insular and stuff. So, if somebody uses the right language or communication—body language, physical language, et cetera, and makes you feel like you’re in home space, then, I think, that is a criteria that loosens the strings. And so, I think that means that I, conceivably, have an advantage investing in people of color, and that a woman should have an advantage investing in products that serve half of the population that has been underserved – in theory. In practice it’s hard because—this author Richard Wright talks about this phenomenon called the beast in the skull, where he says that the effect of racism—racism twists the psychology and the consciousness of the racist, and of the receiver of said racism. So I’m as awful as a so-called racist is,and so I don’t trust my instincts sometimes because I’m wracked with my own level of guilt about my own biases, and about stuff that I’ve internalized that I know has been fed to me and I really don’t want, but that I have. I get all twisted up about it myself, and that is tragic. I don’t really know what to do about that.

Let’s come back here for a second. How do you—we touched on this quite a bit, but how do you feel about the state of Tech in 2016? Like what is really exciting to you? What frustrates you?

What’s really exciting to me is the unrelenting optimism. I really do feel like Tech as an industry is a very supportive culture once you’re on the inside of it. And it’s a very collaborative culture and some people are always co-conspirators and stuff. And even though there are—yeah, so there’s that. And then the piece that troubles me a little bit is this thread, or this belief in the hero culture and the cult of the founder and these sycophants, you know? You know, Jobs didn’t change the world alone, obviously. And so it’s scary to think about that because I think of that makes it harder to build, really inclusive and ultimately resilient culture – that hero culture thing. And it’s also not true of the best of tech. The best of tech is very collaborative, and it’s very open to criticism and is constantly adjusting and is swim or die, and so it’s always moving, and the best of tech feels like a hip hop world – you’re only as good as your last hit, and you’re always trying to get on somebody else’s single, and there’s beefs, but you’re all in this together and ultimately you’re trying to lift—you’re trying to push the whole culture forward, and you’re remixing the past and you’re constantly sampling and you know your history and you’re tied to this optimism through generations. And I think these are really wonderful features of this industry and they’re poorly understood by people outside of it, and then a lot of newcomers, which scares me a little bit. I’m cautiously optimistic now.

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

Yes. A VC said something beautiful the day before yesterday. She was talking about feedback cycles and how some are longer and some are shorter. And in VC, the feedback cycle is so long that it looks like a straight line because it just takes forever to—it takes six, seven years to learn because that’s when whatever comes to fruition when you seeded the company. When it’s outcome has started to play out. And so, I don’t even know if I’m good at this yet. I know, now, that I can have a career in it but I don’t know if I’m going to get in it yet. And so, I think I need another three to five years to just know that. So, maybe ask me in three to five years but I suspect I’ll be doing this for 20 years.

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

Number one would be to save money. Because if you have personal runway then you are structurally more like most of the people who have succeeded. That’s one and that’s not an easy thing to do, but save money. The second would be to try and divide the world of startups, especially in early stage setups, into two functions that constitute a startup. One is building the product. The other one is selling the product. And so figure out if you’re a builder or a seller and don’t be afraid of sales if you are a seller. Choose the one that you have the best chance at. By keeping it simple that way you can maybe orient and organize your activities around one of those two frameworks. Then, the third would be that who you know can be the difference maker, who you know is not whose cellphone and email address you have. It’s who is going to go into bat for you. A lot of people wrongly think that collecting a Rolodex is productive networking, and I think but that’s only 1% of it and I think that probably 60% of it is effective follow-up so I can’t tell you the number of times I’ve said, reach out to me and somebody reaches out. We have a nice first conversation. I don’t hear from them for a while and they reach out asking for something. At that point you’re like asking a stranger for something. What’s that going to do for you? Add value before you extract it. Be thoughtful and followup. Treat people well, meet them where they’re at. Be curious about other’s lives and learn about them. Listen to others and then use that to build your network.