So why don’t we start from the earliest years? Tell me about where you come from.

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.”