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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Holy shit.

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

Wow.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

True.

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

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

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

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

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

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

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

Sure. I’m from the St. Louis, Missouri area. Technically I’m from southern Illinois, but when I say Illinois, people think Chicago, which is like six hours north of Shiloh, Illinois, where I’m from. I lived there from kindergarten until I graduated from high school.

I was always a shy kid—soft spoken, quiet, very much a bookworm. I was also into video games from an early age thanks to my dad’s influence. I also really liked the internet because it was this new, shiny thing. In Belleville, most people are like-minded—so because the Internet has so many subcultures,  I felt like I could finally find my place. I eventually taught myself how to code, HTML and CSS to start, and how to create graphics. I made random websites based on stuff I was interested in; I think I made my first website in 6th grade. It was on Geocities [laughter]. I kept doing it throughout high school and it morphed into my passion.

After high school, I went to a small school called Maryville University in St. Louis, thinking like, “I’m going to be a web designer for a living, that’s a thing people do I guess?” But my school didn’t actually have much for web design. I told them I wanted to major in web design, but they’re like “uh, we don’t have that, what are you talking about?” They did have very small graphic design program, so I decided to major in that.

“The summer before my sophomore year, my dad got laid off so my parents couldn’t help me with school anymore. I had a decent scholarship based on my strong academics from high school, but my university was so expensive that I couldn’t afford the rest of the tuition. The school wouldn’t let me continue until I paid back what owed from my freshman year, so I left school and got two jobs: first at Build a Bear and the Apple Store, and then Apple and a waitressing job.”

The summer before my sophomore year, my dad got laid off so my parents couldn’t help me with school anymore. I had a decent scholarship based on my strong academics from high school, but my university was so expensive that I couldn’t afford the rest of the tuition. The school wouldn’t let me continue until I paid back what owed from my freshman year, so I left school and got two jobs: first at Build a Bear and the Apple Store, and then Apple and a waitressing job. I was thinking, “well, I’ll work on paying them back and just figure it out as I go.” After about 2 years of working while taking a few community college classes, I finally paid back the freshman year debt. But by then I was so disillusioned with Maryville University and the Midwest in general that I was like, “well, I’m moving to California now.” So I went online and searched for design programs in California.

I found a school in San Francisco and I got interested in their animation program. Suddenly I was like “well now I’m going to be an animator.” So I saved up, transferred Apple stores, and moved to San Francisco to attend the Art Institute of California (AI). Eventually I figured out that animation wasn’t a great fit for me. I love to watch animation, but I didn’t enjoy the process of making it and the school was extremely expensive. But by that point I was already kind of in love with San Francisco. I’d been here about a year, so I was like, well I may not be going to school there anymore, but I have to figure out how I can stay here. So I left AI, then I went on Craigslist and found a second job, working as an office assistant at a startup called Socialcast in SOMA. I  eventually let them know I was into design and that I could code, so they allowed me to take on some small projects for the company while I worked as an office assistant. When my boss went on maternity leave, I quit my job at Apple and went to Socialcast full time, which kind of started me on this tech path.

“Learning how to code was very tedious for me [chuckles]. I had to follow so many tutorials. I also feel like I’m always comparing myself to developers I meet here who are extremely talented. Sometimes I don’t even want to call myself a coder or developer compared to them. I’m a designer who can code. That’s an important distinction to me.”

What was the experience like for you, teaching yourself to design and code?

It partially goes on instinct. I’ve always be attracted to visual endeavors; I’ve been drawing, painting, and things like that since I was in junior high. So I feel like design is very similar to where it really helps if you some natural instinct for things like handling visuals and being empathetic to users, but there are also many things you have to be taught. As for coding, there’s more effort involved for me. I enjoy it, but I sometimes struggle with the logic behind it. Learning how to code was very tedious for me [chuckles]. I had to follow so many tutorials. I also feel like I’m always comparing myself to developers I meet here who are extremely talented. Sometimes I don’t even want to call myself a coder or developer compared to them. I’m a designer who can code. That’s an important distinction to me. Learning how to code was challenging, but learning how to design has been fun because it’s about reading people’s emotions, designing interactions and visuals, and things like that. And I am always learning. I’ve never had a full formal design education. It’s mostly been on the job experience. Since that’s something I’m aware of, I always try to keep reading and learning.

Tell me a little bit more about your work and things that you’re proud of—things that really excite you about your work.

One thing I’m a big advocate for in my work is thinking outside the typical mold that tech people in Silicon valley seem to be designing for. Even in the most subtle ways, so many people are designing for users who are in demographics that are similar to themselves or other people in their “bubble.” By default, they are designing for someone who looks like them. And most designers in San Francisco are white guys, with some white girls mixed in here and there. So I’m often the person chiming in with things like “Wait why do all of the avatars have that kind of hair? Not everyone has that texture. Why are all the hands holding the mobile devices in these photo white” And I know details like that are such a non-issue for some people, but because I notice it I like to challenge other designers on it when I can. Lately I’m reading up on things like how to design for those with disabilities, like design for people with hearing or visual disabilities. So that’s kind of the thing I really get excited about, just thinking about audiences that aren’t as focused on.

“One thing I’m a big advocate for in my work is thinking outside the typical mold that tech people in Silicon valley seem to be designing for. Even in the most subtle ways, so many people are designing for users who are in demographics that are similar to themselves or other people in their “bubble.” By default, they are designing for someone who looks like them.”

What were your first impressions of Silicon Valley?

I didn’t really have a strong impression of it before moving here. I think I saw a movie when I was in junior high, Pirates of Silicon Valley? I really never saw myself having anything to do with it—I didn’t correlate my nerdy hobbies like web design to be related to tech. And then when I got the job at Socialcast, it was still all so new to me. There were only like 10 to 15 people in the office at the time, and I didn’t even know what a startup was. I was coming in thinking like, “Ok, I need something that’s going to pay my bills—that’s all I care about.” But when I got hired they were starting a round of funding, so I was being thrown into this fast paced startup world. And at the same time, I was still working part time at the Apple Store. So it was very different, being an hourly retail employee going into a startup world. I had no idea of what to expect but what I learned very quickly is there’s a lot of really smart people working really hard on something, and everyone’s really passionate. So that was kind of cool because that’s the kind of work ethic that I personally admire. So I was like, “Okay, so much is happening here.” So I didn’t know what I was witnessing when I first moved here, and in retrospect I’m like, “Man, I should have met more people and networked and all that!” But also, I’m terrible at networking, but it was still cool though to be a part of it.

“I would definitely say a sense of isolation. It’s a little due to my own personal insecurities because I haven’t finished school, but on top of that, it’s hard when no one looks like you or can relate to struggles you may have.”

What have been some of the tougher parts about working in tech for you?

I would definitely say a sense of isolation. It’s a little due to my own personal insecurities because I haven’t finished school, but on top of that, it’s hard when no one looks like you or can relate to struggles you may have. It’s been a challenge for me lately, especially now that I’m getting older and really wanting to explore and embrace my ethnicity. I actually did a 23andme genealogy test like two years ago to learn about my heritage and ethnicity because there’s a lot of holes in my family tree and I just had this feeling of wanting to define who I am, ethnically. Lately I’m feeling much more aware of what it means to be a Black woman than I have been ever before. I’m finally confident in proudly declaring that I’m a Black woman, but I work in an industry where I feel like I can’t let that pride be known because I don’t want to make a lot of people uncomfortable. So it’s kind of like a weird double act where outside of work, I feel very “woke” or aware of social justice and civil rights issues affecting Black Americans and other minority groups, but then at work that side of me never comes out because I’m scared that it’s not appropriate. And then I feel so frustrated that I’m even having this internal struggle where I’m so concerned about making other people uncomfortable.

“Lately I’m feeling much more aware of what it means to be a Black woman than I have been ever before. I’m finally confident in proudly declaring that I’m a Black woman, but I work in an industry where I feel like I can’t let that pride be known because I don’t want to make a lot of people uncomfortable. So it’s kind of like a weird double act where outside of work, I feel very “woke” or aware of social justice and civil rights issues affecting Black Americans and other minority groups, but then at work that side of me never comes out because I’m scared that it’s not appropriate. And then I feel so frustrated that I’m even having this internal struggle where I’m so concerned about making other people uncomfortable.”

It doesn’t help that I have had these awkward conversations where people just don’t know or care that I identify as Black so they feel comfortable saying really ridiculous or ignorant things. Like once I was in Lyft and the driver talking about Ferguson because I mentioned I’m from St. Louis. It was right around the protests that happened after Mike Brown was shot and he was totally ragging on protesters, and just being very insulting and condescending to the community as a whole. I remember thinking “Wow, would he say all of that to me if I had visibly darker skin?” Would he be comfortable saying, “These people are rioting like animals”’ or whatever he said. I think the answer is no, he wouldn’t have.

And so that’s the worry I have—although someone may seem like a great person overall, they’ll have some beliefs may be really different than mine when it comes down to it and I don’t want to cause problems at work or networking as a result. I don’t want to make people feel uncomfortable or exclude them from my life due to difference of opinion, but to me there are some ways of thinking that I can’t accept because they actively hurt people. So I end up compromising my beliefs and tolerating things that I know I shouldn’t. In the past, I would just nervously laugh along with jokes and smile when on the inside I don’t agree. Lately, in the last year or so, I’m trying harder to tactfully call people out, but it’s quite hard to do sometimes.

“I don’t want to make people feel uncomfortable or exclude them from my life due to difference of opinion, but to me there are some ways of thinking that I can’t accept because they actively hurt people. So I end up compromising my beliefs and tolerating things that I know I shouldn’t. In the past, I would just nervously laugh along with jokes and smile when on the inside I don’t agree. Lately, in the last year or so, I’m trying harder to tactfully call people out, but it’s quite hard to do sometimes.”

One star for that driver.

Yeah, but, ugh, that’s one thing I’m so embarrassed about to this day! I didn’t even rate him badly. I just was like, “Oh, he was really nice before we talked about Ferguson, and he obviously has no idea what he was talking about.” I still gave him 5 stars. I basically give everyone a 5 star, but after that, it haunted me for weeks. I feel like Tiffany today would not have been so meek, but back then I was still so mousy about issues of race and politics. I just didn’t want to talk about it, because ignoring microaggressions is what has helped me thrive in college and in my career.

And I don’t want to sound like I think I some perfect person who gets it right each time. Honestly, in the past I used to think most race issues didn’t affect me. But because I have a younger brother, I see him in all of these young black and brown men being targeted by police brutality or the justice system. So that helped wake me up, because my family isn’t totally protected from the effects of institutional racism just because we have lighter skin. It could happen to me too. And at the same time, me finally realizing that social justice issues directly affect me or those I care about shouldn’t have been what made me finally pay attention to systematic inequalities. So now I occasionally feel guilty for judging people who are ignorant about civil rights issues because I was still quite naive seven years ago when I first moved here.

“Honestly, in the past I used to think most race issues didn’t affect me. But because I have a younger brother, I see him in all of these young black and brown men being targeted by police brutality or the justice system. So that helped wake me up, because my family isn’t totally protected from the effects of institutional racism just because we have lighter skin. It could happen to me too.”

But I think most people, even the naive, now know that something is going with the race relations in this country. It’s good. I feel like it all of of this racial tension needs to come up to the surface so people can talk about it. While we may never be able to end racism, we can start acknowledging and addressing the systemic issues and begin to move forward. Because I think when Barack Obama got elected, people were like, “Well, racism is over!” I don’t think that’s been quite the case [chuckles]. It’s been a very weird thing to witness on the activism I’m seeing online and offline elsewhere versus what I’m witnessing in my real life.

Yeah, it’s so interesting. Have you found support networks here yet?

I have, and I haven’t. I follow lots of different social justice accounts on Tumblr and Twitter, where people can share their own personal stories or report on different situations happening across the globe. It’s nice to find a connection through other people’s experiences.

The one support group I have found that is local is online, a Bay Area “Women of Color in Tech” group. It’s nice to have a place where other women of color will listen to my concerns and validate my feelings. So I have found a support group in that sense, but I haven’t actually made any friends in the group.

I have friends in the Bay Area that are designers of course—other women designers and other women of color designers—mostly Asian women. And while I’m sure we could discuss the hardships of being a woman in tech, I don’t think I could approach them about issues concerning race or anti-blackness. I don’t know if they will feel comfortable talking about it, and honestly I also don’t know how much they would care. I don’t think I’d find any support in my professional network. So that’s something I do think is missing, that solidarity.

“The Bay Area is more diverse overall than my hometown, but seeing black and brown faces is so rare in tech. One of my friends from grade school had a work trip here recently, we met to catch up and talk about work and life in general. It was so nice just vibing with her. Because I hadn’t done that ever, really— talking about professional issues as a black woman with another black woman. She isn’t a designer—she works in economics. But it was still nice to have that moment.”

The Bay Area is more diverse overall than my hometown, but seeing black and brown faces is so rare in tech. One of my friends from grade school had a work trip here recently, we met to catch up and talk about work and life in general. It was so nice just vibing with her. Because I hadn’t done that ever, really— talking about professional issues as a black woman with another black woman. She isn’t a designer—she works in economics. But it was still nice to have that moment. I wish I could discuss social justice issues more and talk about these things openly, instead of me being complacent and pretending that race isn’t the issue. Unless I’m on Tumblr, and then I feel okay publicly acknowledging that it’s an issue [chuckles].

Yeah. You mentioned in your pre-interview that you hadn’t met another black woman designer in your six years here in tech?

Yeah. I feel like I’ve met maybe one or two in passing, but I’ve definitely never worked with or had a friendship with another black woman designer. Obviously I don’t want to be friends with someone just because we have a similar ethnic background—that’s shallow. But it does make me sad to knowing I have no black designer friends—male or female. That’s weird to me. I know there’s black women designers out there. There has to be. But where are they? If there are no black women designing the apps and sites that so many people use, then that voice isn’t being presented or considered in the design. Are things being designed with black women in mind? Or Latina or Hispanic women? I don’t know. I don’t think so.

Do you feel like you have role models that you can look up to?

I don’t have any black woman designers, but I do have other female designers as role models, for sure. Actually, one of my personal designer role models is one of my really good friends. She’s an amazing designer and an even better person. She’s also a woman of color too. I used to work with her at my last job. Once she left, I realized how wonderful it is to have a friend and mentor at work. Not only does she mentor me in design, but I’ve learned so much from her about workplace politics. I’ve witnessed people discriminate against her. I don’t know how much of it was race related, perhaps some of it was, but working with her I saw what it looks like when men are threatened by strong women. Confident and smart women taking taking leadership positions threatens some men, and I witnessed that happen. And it was unfortunate, but she handled it with such grace, elegance, and perseverance. I’m glad that I have someone that I can turn to not only for career and design advice, but also for help in navigating the realities of being a minority and a woman in the design world. She’s definitely someone I can go to when I feel like I’m lost.

You touched on this and you mentioned in your pre-interview that you’ve had some really unique experiences as a pale black person.

Sometimes I think that non-black people don’t really know what I am, which used to actually really surprise me. I never thought of myself as being racially ambiguous until I got to college. My school wasn’t diverse and I started getting the “what are you?” questions. Right now I have braids, I think maybe that helps. People are like “oh ok, well, she’s something…” but when I first moved here I used to straighten my hair. A common question I get is if I am part Japanese, which is amusing to me because I have 0% East Asian genetics. I just happen to love studying the language.

But from time to time, I’ll hear comments from people or they do things like casually quote a song and use the n-word, I’m just like “whoa, would you have been as comfortable saying that if I had darker skin?” I don’t think they would. Like you wouldn’t have said that if I had the same skin tone as my dad, who matches the visible spectrum of what non-black people perceive as being black. So I think sometimes people feel like more comfortable saying things that are not appropriate around me, but on the flip side I think that it’s kind of up to me to say something. But that’s also much pressure! I’m naturally not a combative or antagonistic person, but even when I’ve spoken up in the past, people are like “Oh, what are you mixed with?” So it’s always really awkward. But I’ve always felt like I have had to prove my blackness. So even today, I find myself being like “Stereotypes are gross but of course I can dance, of course I can cook soul food.”

As an adult, I have wondered how many other black people think about this stuff, but I don’t have a network of people talk about it with in the Bay Area. Growing up, I really never talked about race like this. The St. Louis area is very segregated. It’s like you’re black or you’re white—even non-black people of color seemed to “pick a side,” if you will. And I liked things that black people weren’t supposed to like, like computers, video games, and anime. I took advanced classes in junior high and high school where there were only a handful of black kids, in a school that was like 50% black. And then I had this super light skin, eyes, and hair that somehow made me a target for some black kid bullies, saying I stuff like I wasn’t even an Oreo (an insult saying someone is black on the outside, white on the inside), that I was just an other.

So, by the time I started college, I was perfectly happy being like “fine, they don’t think I’m black, whatever. I’m just my own thing.” Which was so weird, because my dad is Black, and my mom is technically mixed with White but identifies as Black. So at home, I was Black but at school I felt too intimidated to say I was Black. So that’s why I think I’ve had this epiphany in the last few years where I’m like, no I am Black too. The 23andme test was like the final bit of ammo I needed. I’m 68% African. I may be mixed with other things, but that is my proof. It’s what made feel like I can claim my blackness, even though I’m on the lighter side of the spectrum of American Blackness.

“I feel like I’ve met maybe one or two in passing, but I’ve definitely never worked with or had a friendship with another black woman designer. Obviously I don’t want to be friends with someone just because we have a similar ethnic background—that’s shallow. But it does make me sad to knowing I have no black designer friends—male or female. That’s weird to me. I know there’s black women designers out there. There has to be. But where are they? If there are no black women designing the apps and sites that so many people use, then that voice isn’t being presented or considered in the design. Are things being designed with black women in mind? Or Latina or Hispanic women? I don’t know. I don’t think so.”

I know my friends and even family aren’t aware of these internal identity struggles I have. So, I know sometimes I’m more sensitive about making people accept that I am a valid form of Blackness. Which sounds really weird because at the same time if you talked to me ten years ago I would be like, “No, I’m not black. Black people don’t accept me and so I don’t accept them.”

And I know I don’t face the same level of discrimination that comes with darker skin. I also know that light skin privilege exists. I feel like I’m in a very interesting place today and definitely this is like—I’ve never even talked about this with anybody like before. I feel so comfortable discussing this with you [chuckles], but now that you asked that question, all of the feelings that I had before about how I never really felt like I could proudly say that I’m a black person. But now, I do feel like that and sometimes I’m almost like beating that fact over people’s heads because I’m finally like comfortable saying that. But, that’s only around friends. When it comes to work, I don’t really like to talk about race because like I said, I’m always worried about the reaction I’ll get.

I’ve talked a lot with people about how like the way that they grew up and how it impacts like how they are in work environments and stuff like that. For some people, it manifests in now wanting to like minimize conflict and that sort of thing. So I’m curious how like you’re upbringing you think affects like how you deal with stuff in the workplace.

I would agree with that for sure. I think people from the Midwest tend to like be really nice up front, because that’s just how you’re supposed to be—neighborly and super accommodating. And so I definitely have that quality, but even in my own home growing up, I was always the very quiet one. But that said, I feel like as I’m getting older, finding my voice, and becoming more comfortable in myself, I definitely am getting better at speaking out when I don’t like something. But I do sometimes catch people off guard when I don’t like something because I usually am so easygoing. I naturally want people to get along and want there to be harmony and balance. But when I do have to confront someone over something I have to psyche myself into it. Like I said about the Lyft driver guy, like I could have passively given him a bad review, but I still felt bad doing that. I was thinking “Oh but he has a hard job too and maybe he had a bad day.”

I have a very similar temperament. I’m just now learning to stand up for myself too—not letting everything slide.

That’s my biggest thing. I’ve always struggled with microaggressions, even before I knew what they were called. They have happened to me my whole life and I have typically just let them slide. I felt like at some point, I’d eventually reach a breaking point over it so that’s why I felt I had to get better at not letting them go. But standing up for myself—even if it’s not confronting someone in the moment—that’s my personal goal is to be able to do that.

I honestly still can’t.

It’s hard. One of my current goals is to, especially with someone I care about, is to call them out on it if they say something that isn’t cool. For all scenarios, even when it’s not something that directly relates to me. Especially in work situations, where I’m like, “I’m cool with you and we’re friends, but you can’t say that kind of stuff about women or make jokes about someone’s body or sexuality or anything like that.” Being in the Bay Area, sometimes I feel like I’m working with a lot of immature man children. Like a designer I worked with compared an Asian interview subject, specifically her voice and laugh, to a yellowface character from a sketch tv show. This was during an interview round table session, in front of other senior people and the recruiter. No one said anything. Like, he was a senior team member and he was openly making jokes like that. I wish I had said something, you know? When I think back to stuff like that I always feel a kind of pang of regret, like “I should have said something.”

Based on all of your experiences, what would you look for in a future job?

That’s something I’m thinking about a lot now. I have separate buckets of criteria for what I’m looking for in future roles. Like is it a job where the product is  making a difference in people’s lives, helping somehow? Is it a job where I am being fulfilled personally? Is the team diverse? So far, the jobs I’ve had have been really good for personal growth and career growth, but they haven’t matched the other criteria as much. And for the second criteria bucket, for a future job I definitely would love to do something related to like my hobbies or interests. Like I have been studying Japanese for almost a decade now. So I would love to do something with Japanese in my career so it feels like it’s not just a hobby and something that I’m actually using everyday.

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

I think what’s really exciting is that the things we work on in tech are so normal for everyone, even those outside of the tech world now. Actually, I just got back from Bahrain last week. My friend is from there and I went for her wedding. In Bahrain, Instagram was everywhere. And it was so crazy think that this product that was originally created by a small team in the same city where I live is touching so many people’s lives across the world. Like storefronts had their Instagram names on the sign below the store’s name, like that’s how big it is there.

But what scares or frustrates me is like stuff like bullying, or how tech can give hatred such a prominent platform.

“Diversity and inclusion just isn’t a concern for most people in tech. For example, if you’re happy and comfortable with your design team being homogenous, then you’re probably not going to feel challenged to make it diverse unless somebody points out, ‘Hey, this is a problem.'”

Also, it seems that now people are getting so hung up on online relationships that they don’t know how to have offline relationships anymore. I just watched Master of None and all those things he’s talking about are things that I am witnessing friends go through. Like people don’t know how to have relationships. They’re so worried because there’s like 5,000 people they can date via an app. They don’t want to settle and things like that. So that kind of scares me… And I’m a technology optimist.

A lot of people are scared of the Big Brotherness Google a lot, but I’m the person who’s like, “Google, take my data. You help me get to meetings on time; you help me not get lost. You can have all my data.” But I’m always a little worried that the era of optimism and innocence with the Internet is gone. People are more nefarious and don’t have the best intentions with your data out there. So that’s another thing I think is really big for tech right now is security. Now that the internet is more mature, we’re starting to really see more standards now. From a product development standpoint, maybe you can’t move fast and break things—to quote Facebook—but now users are more aware about their data. So you have to spend more time making sure your product is safe and compliant. So I think it’s nice that we are self-regulating things, but I don’t want tech to get too regulated. The Internet has always been a special place with unlimited creativity. Overall, tech is very exciting right now. So that’s kind of the cool part, witnessing it all.

How do you think tech can be more accommodating to diverse perspectives in design?

That’s something that I think about a lot. I really think it goes down to getting people involved early. I’ve met people here who have a lot of privilege, but they don’t realize it. And it’s very much a buddy system in tech where one person gets into a company, and then they only refer their friends and others in the social bubble. And because they don’t have a diverse friend group, the company’s demographics become very uniformed. Many people seem threatened by the idea of forcing diversity, but I think it is good to have someone at an executive level who is tasked with increasing diversity and making workplaces inclusive to all kinds of people.

Diversity and inclusion just isn’t a concern for most people in tech. For example, if you’re happy and comfortable with your design team being homogenous, then you’re probably not going to feel challenged to make it diverse unless somebody points out, “Hey, this is a problem.” I do feel lucky that at my current job we do have some diversity in the sense that there we have people of color on the team, and it’s mostly women. But we’re just a small company, and no one’s looking to us as a design leader in the industry compared to places like Facebook, Twitter, Pinterest, Google. And from what I’ve seen, those teams aren’t diverse.

“Black Twitter, a lot of the young people on there, they’re hilarious and amazing and I love it, but how many of the young kids participating are going to think, “I want to get a job doing something related to this?” I don’t think many are because it’s not being presented as something that they can be apart of. These platforms need to reach out early because that’s their audience right there.”

InVision just had a documentary they did I think last year or a couple of months ago, and it was like the top designers disrupters in the industry. Not one person of color was in there, I think. Maybe there one woman on the list. Stuff like that. People aren’t doing it on purpose. I think most of the people in these companies just don’t have very diverse professional and personal groups, so they likely couldn’t seek out diverse voices even if they wanted to. But if no one’s calling it out, it’s not going to change.

We also need to go into primary and high schools and get kids involved earlier. And not just coding—I think that introducing design as career options for underrepresented groups is important too. Because the kids—Twitter, for example. Black Twitter, a lot of the young people on there, they’re hilarious and amazing and I love it, but how many of the young kids participating are going to think, “I want to get a job doing something related to this?” I don’t think many are because it’s not being presented as something that they can be apart of. These platforms need to reach out early because that’s their audience right there. If you have a diverse user base, but the people creating the product aren’t, then you’re going to have some problems eventually. Tumblr had a problem, actually, awhile ago where they censored some popular tag, flagging it as not safe for work or something? I don’t remember, but it impacted a huge chunk of Tumblr’s user base. A lot of marginalized groups that feel like they can find their place or community on Tumblr, but suddenly they’re being treated different by the app developers. So now they don’t trust the app, and it’s perceived value for the user goes down. If only there had been one person, one voice on the team that could have been like, “Hey, this isn’t such a good idea.” That could have been avoided.

That’s why you need diverse teams. My hope is that as the internet generation grows up, we start seeing more diversity. I hope that tech becomes less of a “bro club.”

“I would love to stay in San Francisco for the next five years but realistically, I can’t. And I know I am speaking of a place of total privilege, as a tech worker in San Francisco. I can’t imagine how hard it was if I was still working retail or if I was working as an artist. I worry that life in San Francisco is not sustainable, so I really don’t know where I’ll be in five years.”

Where do you see yourself in five or ten years?

Oh gosh. Well as much as I love San Francisco, it’s really different now compared to when I moved here. I moved from Lower Haight to live in the Outer Sunset by the by the beach in 2014. I love living by the beach, but we truly only moved there because it was the cheapest place to find a bigger apartment at the time. But now getting downtown for work is such a hassle. I would love the ability to live closer to downtown, but I am not comfortable with how high rents are here. I would love to stay in San Francisco for the next five years but realistically, I can’t. And I know I am speaking of a place of total privilege, as a tech worker in San Francisco. I can’t imagine how hard it was if I was still working retail or if I was working as an artist. I worry that life in San Francisco is not sustainable, so I really don’t know where I’ll be in five years. I hope I’m still working as a designer, but likely it’ll be in a different area. I’ve heard that L.A. has a “Silicon Beach,” and I know there is a “Silicon Prairie” somewhere in the Midwest, although I see myself on a coast. I just hope that wherever I am in five years, I am making user experiences that are helpful to someone.

“You really have to be very self-driven because there are times where it seems that no one’s going to help you. You really do have to be self-driven, which I know can be hard, especially when you’re young. But when you’re competing with very privileged people for highly desired jobs, you can’t afford to wait around—you have to create opportunities by showing others your talents and interests.”

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

You really have to be very self-driven because there are times where it seems that no one’s going to help you. You really do have to be self-driven, which I know can be hard, especially when you’re young. But when you’re competing with very privileged people for highly desired jobs, you can’t afford to wait around—you have to create opportunities by showing others your talents and interests. When I got that job at my first startup, if I had waited for someone to ask me, “Well what do you want want to do besides admin work?” I don’t think that day would have come. Instead, I was like, “I know how to code. You guys need someone to make these internal pages. Do you want me to do?”

Another piece of advice is, as a person of color, people may look down on you sometimes or have lowered expectations. It hurts, but you have to say, “You know what, I don’t care about you. I’m going to give it 110% and prove you wrong.”

And finally, if you’re feeling alone, go online for support! Learn very early how to efficiently use Google. Search engines are your best friend. You can learn the basics by getting on free sites like Codecademy for code or UXPin for design. There are also tons of design and code communities out there, from Twitter to StackExchange to Quora to Reddit. It can be lonely and frustrating to work in tech, and it can be a lot of hard work, but overall it’s such an interesting and exciting place to be.

“It can be lonely and frustrating to work in tech, and it can be a lot of hard work, but overall it’s such an interesting and exciting place to be.”

]]> /tiffany-taylor/feed/ 0 /dominique-deguzman/ /dominique-deguzman/#respond Mon, 28 Mar 2016 03:30:57 +0000 http://techies.wpengine.com/?p=184 Why don’t we start at the beginning? Tell me a bit about your early years and where you come from.

I am a Bay Area native. I was born and raised in San Francisco and Daly City. Then I moved to a suburb, and then moved back. Actually, moved to a suburb, then moved to Sacramento, which was terrible, and then moved directly back to San Francisco.

I went to college because I thought that’s what I was supposed to do after high school. I always prioritized my social life and my friends and fun before anything else. I would do this thing where I would just go into random classes and not really be fully participating in any. I ended up going to college for seven years, and I did three or four different major tracks. I was about ten credits short for three different majors. Then they finally just came back, one of the deans were like, “You need to graduate. You need to leave.” I made a special major out of basically a theory that I would write in a paper format for a cumulation of what I had learned over the years. My actual college degree is a  communication analysis of the performativity of lesbians in mainstream media from 2001 to 2007. So, I like to joke that I majored in the L word. That’s pretty much what I majored in.

“I went to college because I thought that’s what I was supposed to do after high school. I always prioritized my social life and my friends and fun before anything else. I would do this thing where I would just go into random classes and not really be fully participating in any. I ended up going to college for seven years, and I did three or four different major tracks. I was about ten credits short for three different majors. Then they finally just came back, one of the deans were like, ‘You need to graduate. You need to leave.'”

While majoring in the L word, I would work odd jobs to make up the gaps for my scholarships. That’s how I found my way into computers. I started out in sale at Best Buy. I moved from sales at Best Buy to sales at Geek Squad, to tinkering in Geek Squad, to independent consulting work, to working at an enterprise and fixing computers there, to provisioning computers, and then moving into Linux System administration and systems work, and then bouncing around at different areas of a start up. Which is how I’ve landed at Twilio.

When you were first entering computer land, selling computers at Best Buy, did you have any inclination that you would end up in Silicon Valley or was this more of a, “I gotta pay my bills” situation?

It was a little of both, actually. Initially I wanted to work in tech but I didn’t actually want to be a technical person. All of my friends and all of my background has been really focused on communication analysis. So, I really wanted to be in PR. I thought that by having a family friend that had worked at Google—and this was back in the day when, actually, having a family friend working at Google meant something—I thought that I would have an in after I graduated. Because I took so long [in school] and Google blew up the way that it did, that was no longer valid. So, when I first started working in tech it was just a way to pay the bills. Then when I worked at Sales Force it was mostly to pay the bills but also it was that really small foot in the door. Every position I applied for out of that consulting position, none of it was engineering focused. I applied for human resources, for marketing, for project managers, for an admin in their real estate department. I kept going for literally, again, anything other than technical.

When was the moment that you discovered coding and was like, “Oh, this is my shit.”

The part where it was “the shit” was probably not for a long time. I was on this rotating consulting gig. The team was me and less than 20 other people. We all hated it because we were paid nothing compared to what other people were paid. And by nothing, I mean, our consulting firm happened to be based in Dallas, Texas and so we were being paid Dallas, Texas wages. It just so happened that the people sitting next to me were a consulting firm based in San Francisco. We were doing the exact same thing and being paid vastly different amounts.

“I found programming as a shortcut to doing things versus falling in love with it.”

Everyone on the Dallas team were leaving. One dude was leaving and he was the only person to support Linux machines at Sales Force at the time. He turned to me and said, “Dude, I’m leaving. I’m going to Yelp. Do you want this book?” I said, “Yeah. Of course I want this book.” I ended up just filling the gap after he left. As I became the only person supporting Linux machines, I found that a lot of the same things were happening over and over again so I would just script certain things. I found programming as a shortcut to doing things versus falling in love with it. I didn’t fall in love with programming until I went to Twilio and started actually developing.

Interesting. You used the term community-taught to describe your past engineering. Tell me more about that concept.

A lot of people like to say self-taught, self-taught, and I feel like that’s a little too elitist for me. Community-taught comes from the authors who wrote the beginning books that I read to the online tutorials that were always free. I utilized a lot of people’s time. There’s two different camps of people I learned from:  people who wanted to teach and people who just got stuck teaching me. When I didn’t understand something, I would start off by tapping them on the shoulder. When I realized that wasn’t productive, I would actually just carve out time with them. I had to show that by taking two days just to teach me how to do something, it would in the end help me ramp up faster, and I would bother them less if they just took two days, two hours, whatever to teach me.

“A lot of people like to say self-taught, self-taught, and I feel like that’s a little too elitist for me. Community-taught comes from the authors who wrote the beginning books that I read to the online tutorials that were always free. I utilized a lot of people’s time.”

I really need to give credit to these people. I bugged them relentlessly when I was first starting. People who spent their free time learning how to create easier ways for people to grasp concepts. They did that in their free time, too. It’s not fair to say that I learned this all on my own because I didn’t.

What would you say are the most exciting things, to you, about working in tech? What parts of the work really activate you?

Growing up, I really wanted to be an inventor. I knew that inventing something new was going to put me on the map. It fostered creativity. Now I get to invent things, or new ways to interact with things, every day.

I think that where we are right now in tech, or in computer engineering, in general, is at a larger scope than we’ve ever had before. We have people and ideas that are solving problems that we never thought imaginable.

“Growing up, I really wanted to be an inventor. I knew that inventing something new was going to put me on the map. It fostered creativity. Now I get to invent things, or new ways to interact with things, every day.”

There’s this one project that I keep thinking of where these two students figured out a way to use Google to send Doctors Without Borders a text in when they saw outbreaks of diseases. They would map it to a Google heat map and use an algorithm to track the progression of a disease. They were able to send resources before a disease was going to have an outbreak in a certain area—just by using an algorithm. We have all of these minds! Sometimes they’ll do something silly like create new ways to say “Yo” to each other. Other times you have people who say, “Here’s a problem that I totally think that we can solve together.” Generally, the people who really, really want to solve a problem have come at it from a place of passion versus a place of greed. It’s so amazing to see what people come up with.

When did your focus turn to inclusivity in tech?

It kind of bounced around inclusivity in tech. When I was at Sales Force and I didn’t feel like I was a part of the technical community. I thought using employee interest groups would be a way for me to network. That’s kind of how I got started with inclusivity.

When I moved to a smaller company, I realized that things were way different. We had started an inclusion group about eight months after joining. A colleague and I were leading that for a while. When that person left, we started to feel a lot of the impact of having a person leave or why people were starting.

It wasn’t until someone explicitly pointed it out to me that I was the only girl in the room or that I was the only gay person on the team that I moved into the diversity inclusion work. I was constantly the spokesperson for this entire identity. At the time, I didn’t think anything of it. Someone pointed it out it was like, “You know you wouldn’t have to be that if there were more people of color in your company.” And I was like, “Oh, shit. I probably wouldn’t have to be the spokesperson.”

“It wasn’t until someone explicitly pointed it out to me that I was the only girl in the room or that I was the only gay person on the team that I moved into the diversity inclusion work. I was constantly the spokesperson for this entire identity. At the time, I didn’t think anything of it. Someone pointed it out it was like, ‘You know you wouldn’t have to be that if there were more people of color in your company.’ And I was like, ‘Oh, shit. I probably wouldn’t have to be the spokesperson.'”

It wasn’t until I  joined Lesbians Who Tech that I realized that I could have a positive lesbian role model in my life. I was like, “Holy shit. They exist.” They’re not just at home with their wives and cats, or girlfriends.

I started to ask why don’t these groups exist? Why was it hard to get into this industry? When I ask people – whether they’re people of color, or people who identify as female, or LGBT people, or someone with a disability, associating background – there are one of two camps. One: they will believe fully that they got where they are because of who they are and their skill set. And there are other people who are like, “Holy shit. I am so lucky to be here. And I worked my ass off, just like everybody else, but the system worked against me way more than it did everybody else.”

I’m in the camp where I think that the system worked against me a lot and I wouldn’t be here if it wasn’t for opportunity. It’s not fair that I’m the only person to have gotten that opportunity. That I found some random loophole or some random person to give me a shot. I owe almost everything in my tech career to two people. Two people who I interviewed for a position that I definitely was not good for. I left that thinking, “I don’t know why I went to this interview.” They gave me a shot. They did this thing where they assessed what I knew and what I knew and how long it would take me to get up to speed. That’s something I’ve never forgotten and something that I want to give as an opportunity to everyone else.

“It wasn’t until I  joined Lesbians Who Tech that I realized that I could have a positive lesbian role model in my life. I was like, ‘Holy shit. They exist.’ They’re not just at home with their wives and cats, or girlfriends.”

I’ve focused a lot on inclusivity in tech and making sure that the way that I interview a Harvard or Stanford or MIT grad is not going to be the way I interview somebody who is a person of color. The way that I approach a negotiation tactic is not going to be the same for the way that I would interact with somebody who doesn’t have my identities. I need to give these opportunities to people who never even thought these opportunities were available for them.

Let’s go to the dark side for a minute. What have been some of your biggest struggles that you’ve had to overcome during your time in tech?

I have consistent impostor syndrome. I had an interview a couple of weeks ago where they asked me a question and I felt like the answer was way too easy. So, I didn’t say it. And I was just like, “No. There’s no way that the answer is this.” It was, literally, one of those things where it was like, “Tell me one of these things is not like the other.” And it was the equivalent of all of them being blue except for red. I thought, “Nope. That’s not it. They’re tricking me.” I refused to believe that I knew the answer that quickly. I ended up second guessing myself the entire interview.

I am absolutely a workaholic and this industry has definitely helped that. It’s not uncommon to get an email at two in the morning. It’s not uncommon to see people in the office 9:00 at night. It’s generally because we like what we do. It’s not a case of having meals catered and transportation taken care of and lack of dependencies on being home at a certain time. It’s the fact that you love what you’re doing and you believe in what you’re doing. It’s so easy to just lose track of time. Especially if your days are filled with in-person meetings or interviews. By the time six o’clock rolls around, you can finally start doing your work.

“I’ve focused a lot on inclusivity in tech and making sure that the way that I interview a Harvard or Stanford or MIT grad is not going to be the way I interview somebody who is a person of color. The way that I approach a negotiation tactic is not going to be the same for the way that I would interact with somebody who doesn’t have my identities. I need to give these opportunities to people who never even thought these opportunities were available for them.”

In the past while I was fixing computers, having to continuously prove myself was exhausting. It’s compounded by having two kinds of people that you prove yourself to: the ones who have no idea they’re undercutting you and the ones who know that they’re undercutting you, and they expect you to prove something. It makes you work harder, which makes you work later. Before you know it, you’re only sleeping two-three hours a night.

What is it like being part of both the tech community and the queer community? I’m curious to know from your experience what it’s like being queer in tech and being a techie in the queer community here?

Being queer and tech is one thing. Being queer in tech, especially being a female identified queer person in tech is almost invisible. I say that because when you work in a male dominated team, especially a millennial male dominated team, a lot of people will always think, “Oh, yeah, it’s totally cool that you’re gay. Don’t worry about it.” It’s a millennial time where you’ll hear things like, “Oh, yeah, I totally dated a bi chick once.”  I don’t care about that. When I was younger and men were trying to find a common ground with me through male dominated activities. They would say things like, “Yeah, did you see the ass on her?” Or, “Would you hit that?” It’s like, “We both like women, but I like and respect them, and you don’t.” I found that it was so much easier for someone to see me as one of the guys versus someone to see me as a queer person, especially a queer woman. That was always a struggle for me and that’s why I left a previous company.

“I found that it was so much easier for someone to see me as one of the guys versus someone to see me as a queer person, especially a queer woman.”

As far as being a queer person who techs, I feel like there’s a lot of pressure on me. It’s not necessarily because I’m a queer person in tech. It’s more or less that I am a queer person in tech who is also female identified, who is also a person of color, who also came from a lower socio-economic background. Those are so many groups of oppressed people who are looking at you like, “You made it. What else can we do? How can you bring us with you?” It’s like, I can’t carry four groups of oppressed people on my back right now.

It’s also those things where a diversity company or a diversity focused initiative will come to you, and just say, “You want more diverse talent, right?” It’s like, “Yeah, I do, but I want the right talent, and I want to give equal opportunity without you forcing people that you know aren’t right for this position.”

I went to a career fair recently just to recruit people, and they were like, “We’re diversity focused, diversity focused.” I’m like, “Okay, that’s great.” I would love to hire more people that are like me, or that are in groups that I feel have been oppressed, and have more obstacles than others. The candidates that were thrown at me, just at this particular conference, had never programmed a day in their life. There are a lot of great candidates who identify with these groups but are not as entry level. People expect you to make certain changes or judgement calls because you’re a person of color and I don’t think that’s fair.

What is it like in your experience being both a techie and a local?

I have tried very, very hard to not say this and to not blow up at this. I have felt this bubbling below the surface for a quite some time now. My family was pushed out of San Francisco. It was San Francisco before the first bubble burst back in early 2000. I remember watching my family be a little devastated that they could no longer afford the place that they had lived in for decades. Moving us up to the suburbs where my dad had to commute two and a half hours to work and my mom had to commute an hour and a half. I remember not being able to be with my family because they were always working and commuting in order to pay for our house in the suburbs.

I went to school. I got a great education and I worked really hard to be where I am. That’s when I moved back. I actually moved back to the same neighborhood that I grew up in. People call me “Techie Scum” and that I’m gentrifying our neighborhood when I’m really just taking back the neighborhood I was kicked out of. It really sucks. People who have been here for six years will tell me that I’m ruining the neighborhood, or that because of my company, or the industry that I’m in, that I’m the reason that they’re being evicted.

“My family was pushed out of San Francisco. It was San Francisco before the first bubble burst back in early 2000. I remember watching my family be a little devastated that they could no longer afford the place that they had lived in for decades. Moving us up to the suburbs where my dad had to commute two and a half hours to work and my mom had to commute an hour and a half. I remember not being able to be with my family because they were always working and commuting in order to pay for our house in the suburbs. I actually moved back to the same neighborhood that I grew up in. People call me ‘Techie Scum’ and that I’m gentrifying our neighborhood when I’m really just taking back the neighborhood I was kicked out of. It really sucks.”

I understand it because I went through it for a long period of time. I moved back because I wanted to be home and I wanted to feel like I was safe again. My grandmother actually lived and has lived for a number of years, one block away from where I live or where I work now. When I was growing up, I was told never to leave my grandmother’s house and go anywhere, except for going straight to BART. Now the rent is more than she’s ever made in a year, probably. It’s so infuriating to see people who actually just fit that mold of what everybody hates, and then to be put in that same bubble. I don’t think there’s anything that I could actually do to make my voice heard in that.

There are people who complained about the homeless population in San Francisco, or the people who like to capitalize on buses, or who like to celebrate sports wins in a violent way towards the city. You know when I was growing up, they were giving out Giants tickets on the streets, begging people to go to those games before it was relevant. While I was growing up, 49ers game was something that we don’t even go to because it wasn’t in a safe neighborhood. And now, people are basically just reclaiming it, and claiming that they’re natives after six years. It’s just infuriating, really. I love San Francisco. I grew up here. It’s great. It’s changed a lot. But the hostility from six-year locals is almost enough to just not want to be here anymore.

“I love San Francisco. I grew up here. It’s great. It’s changed a lot. But the hostility from six-year locals is almost enough to just not want to be here anymore.”

We’ve touched on this but where do you find your support networks? Where did you find them earlier in your life and where do you find them now?

My support networks have been people who’ve watched my progression of change over the years. My biggest supporter is probably my brother. He’s seen me through everything. My best friends from high school because we’ve literally gone through everything together. They were there from first kiss to me coming out to somebody’s first marriage and divorce and first kids and everything. My support network are the people who I know I’ve been vulnerable with. People I know who would never judge me for that. Sometimes I know that there are friendships where people feel like they’re depleted because the friendship seems one-sided but these friendships that I have, they’re people I could not talk to for six years and come back and just say, “I need you right now.” And they’re fantastic people.

My technical support networks have been the people who have mentored me and I can, in turn, return that favor. I’ve never felt like that was a one way street. One of my seniors, I probably go to him ten times a day to ask him a question. I try to reciprocate in being like, “Hey. This is an easy request. Let me take all of the easy stuff off your plate and I will work five to ten extra hours a week because I know I took up some time of yours earlier.”

My partner, of course, has been my biggest support network. I’ve never met anybody who has been as supportive as she is. I’ve absolutely never met anybody like her.

“My technical support networks have been the people who have mentored me and I can, in turn, return that favor. I’ve never felt like that was a one way street. One of my seniors, I probably go to him ten times a day to ask him a question. I try to reciprocate in being like, ‘Hey. This is an easy request. Let me take all of the easy stuff off your plate and I will work five to ten extra hours a week because I know I took up some time of yours earlier.'”

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

When I first started looking for jobs I was looking for the right company. Once I got in the door of the company I would find out if the company had a volunteer program. Did it have employer resource groups? What was their PTO like? Did they have food catered? Did they allow dogs in the office? I was all about the perks.

Now, the first thing I think of is, “What does your company look like? What does your board look like? And how does that reflect on where I’m going to be in a couple years?” If I can look at your company and know that these engineers, who just happen to be engineers of color or women engineers, have not progressed in their career for the three years that they’ve been here, that’s going to say something to me. That’s going to either say that they were not set up to succeed or that no one is checking in and seeing what the progression of somebody’s career is. How often are they going to ask me to be their diversity advocate? How often are they going to ask me to be at a table to recruit or to speak on their behalf? Which I’m happy to do but if they means that I’m going to miss a meeting in which I’m going to miss a promotion I don’t know if I want to do that anymore.

“If I can look at your company and know that these engineers, who just happen to be engineers of color or women engineers, have not progressed in their career for the three years that they’ve been here, that’s going to say something to me. That’s going to either say that they were not set up to succeed or that no one is checking in and seeing what the progression of somebody’s career is.”

I’m really focused on what they look like when they work remotely. I have very bad ADHD and a little manic so if they have an open floor plan I can’t work productively. I have to spend one to two days just working at home or in a quiet room. If this company doesn’t know how to work remotely then I can’t be a part of this company in the way that is set up to succeed.

I like to look at where their focus is, as far as how they give back to the community. I like to look at whether they have a dot org and if I can tell that their dot org or non profit branch seems like it’s because it’s a great tax benefit or because the people actually believe in that mission. I like to look at their onboarding process; if they just throw me in the deep end and I’m on call the next day, that’s really shitty, but if they look like they have a 90 day plan to have people succeed that’s fantastic. I look at the things I love from my previous positions and hope that the next company can do better or is open to doing better.

When I worked in tech a primary feeling I had was that of isolation—I mean, there were chicks in tech at that time but it was more socioeconomic for me. I’m curious to know how your socioeconomic background contributes to the way that you feel in the industry. I’m curious if you can relate.

Yeah. Actually, a lot. That’s just something that I don’t think we talk about enough in the industry. We talk about diversity and we always talk about the visible things. As someone from a lower socioeconomic background, it is amazing the difference in ways that people see things. For instance, the first thing is you’re surrounded by people who make so much money and spend it like it’s nothing. The people that you sit with every day may not have the mounds of student loan debt that you do. Or if you are helping your family out, they don’t have to help their family out.

I recently heard a story where there were two people in a sales division at another company and, basically, they were both caught fluffing numbers, essentially. And one of them was a CIS white man who came from an affluent, affluent family. And the other one was a Latina woman who was a single mom and she had just graduated from a state school. And the Latina woman was like, “No. I didn’t do it. I didn’t do it.” And the company came back and it’s just like, “If you just tell us you’ll be fine. Just tell us that you did it.” She like, “No. I didn’t do it.” They tell the same thing to the guy and the guy’s like, “Yeah. I did it. My bad. I didn’t know.” And they ended up firing the Latina woman for lying. And somebody comes back and was like, “Do you know what you just did?” She lied because that was her only source of income and you just cut it. You rewarded an affluent person because he told the truth knowing that if he lost his job he would have his trust fund to fall back on. He would have these resources to fall back on.

“We talk about diversity and we always talk about the visible things. As someone from a lower socioeconomic background, it is amazing the difference in ways that people see things. For instance, the first thing is you’re surrounded by people who make so much money and spend it like it’s nothing. The people that you sit with every day may not have the mounds of student loan debt that you do. Or if you are helping your family out, they don’t have to help their family out.”

A lot of the people companies employ people to clean the offices or to serve food are people of color. That’s when you can really tell who came from a background where bussing their own tables is foreign to them. I will definitely see somebody cleaning off their own table or cleaning out a workstation on their own or offering to hold the door for somebody who’s in the service committee because they recognize those faces. They recognize people like that.

I remember when I got my first offer. I was so excited. My first offer was more than both my parents made combined. I was so excited for a whole month. I remember texting my partner, “I have enough for all of my bills and I can eat this week and I still have more money to put into savings than I know what to do with.” It was amazing and then someone was like, “Oh, cool. I’m so happy for you. What did you make?” I was feeling really good and I told them. They’re like, “You know that your offer was thirty thousand less than what you’re supposed to be making, right?” I was like, “Ugh. I’m an idiot. I feel like shit,” and it was also because I never learned to negotiate. People who come from a lower socioeconomic background learn to be happy with what they have got.

“I remember when I got my first offer. I was so excited. My first offer was more than both my parents made combined. I was so excited for a whole month. I remember texting my partner, ‘I have enough for all of my bills and I can eat this week and I still have more money to put into savings than I know what to do with.’ It was amazing and then someone was like, ‘Oh, cool. I’m so happy for you. What did you make?’ I was feeling really good and I told them. They’re like, ‘You know that your offer was thirty thousand less than what you’re supposed to be making, right?’ I was like, ‘Ugh. I’m an idiot.'”

I spent my college years driving an hour and a half back to my parents’ to clean office buildings from 11:00 PM until 3:00 AM, and then I would drive back to the city, and go to school from 8:00 AM until 5:00 PM, and then I would go to another job from 6:00 to 11:00, and then drive back to clean office buildings. That’s how I could afford rent and that’s how I could afford ramen – and ramen back then was ramen. Ramen was not $11 a bowl. It was like, “Hey. I spent $3 and I got six weeks of food.” There’s so many different aspects. You hang on to the things that you are so afraid to lose because you know that as much as you save, you could lose this job. And this job can be the only opportunity for you crawl out of a hole of debt that you’ve been told to invest in. The amount of times that you hit up for get rich quick schemes, for borrowing money, and everybody who’s asking to borrow money from you is your family, your homies, your best friends. You all grew up the same way and you can’t say no because you know where they’re coming from and you feel guilty for all the money that you make. I think being in tech from a low socioeconomic background is more guilt than it is ever pleasure.

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

A lot of them make fun of me. Not that I’m the one that made it or anything like that.They’re just like, “Dude. You were the class clown and you never took anything seriously.” And they’re seeing me being featured on random articles or something or being mentioned in certain things. And they’re just like, “Who are you right now? When did you grow up and become and adult?”

I think a part of that is because when you grow up in a different socioeconomic background it’s so much easier to get caught in those loops. I still know people who are at Best Buy and who it’s easier for them to climb up that corporate ladder than to take a risk and leap somewhere else.

My dad keeps giving me all these random rules to live by so that I won’t lose my job. His rules are so outdated where it’s like, “Don’t you ever check e-mail from your work computer.” It’s like, “Wait. What?” I think we got into an argument today because I sent him a Google link from my work computer and he was so afraid that I was going to get fired over it. I think that fear rules because people—whether they’re people of color, or from a different socioeconomic background, or people who’ve ever just been fired before —are in a constant level of fear to never let anybody they ever know, make the same mistakes that they did. It’s one thing to get fired if you have a safety net, but if you come from a lower economic background getting fired is not an option.

“It’s one thing to get fired if you have a safety net, but if you come from a lower economic background getting fired is not an option.”

We’ve definitely touched on this, but how do you feel about the state of tech in 2016? What is really exciting to you? What frustrates you?

Exciting, again, is that something is going to come out, that I’ve never even thought of. Whether that’s a good thing or a bad thing, I don’t know. We have all these really, really great minds that are learning to exercise a muscle in ways that they’ve never knew was possible. This big focus on pushing towards diversity.

My biggest fear is that it becomes noise, versus action. I really hope that the right people get involved, not just these companies that want to solve the problem, and not just recruiting in HR, that’s like, “No, we should totally hire more people of color, and women,” but people who are in a position to hire, or in a position to move a product forward, I hope that they will look back and say, “You know what? I can skip this product cycle, and we can really invest in our team, here.”

I’m afraid that the bubble is going to burst, and what that means for the bubble to burst, especially for the people who came out of nothing, and worked their entire asses off, just to get to the brink of it can have it burst on them. People who are entitled to get a dose of reality, if that does happen. The stereotype is just like there’s no wrangling it. There are so many emotions out there like I don’t know what to feel because it’s too much effort to try to wrangle  those emotions because it’s mainly fear.

Yeah. What advice would you give to folks from similar backgrounds to you who are getting a start in tech or are hoping to get into it? What do you wish you’d known in the beginning?

I wish I knew that I belonged here and I didn’t have to continue to try and prove myself everyday. When people give me a compliment, that they mean it. I don’t have to deconstruct it. They were happy with my work and I don’t have to find reasons that they shouldn’t be. I wish that I knew not to be so afraid of losing what I have in working here, and that a risk is worth taking. That it’s really, really, really hard to take when you know what you can lose. That’s why it’s so hard for people who come from lower socioeconomic backgrounds to start their own company. Probably people from affluent backgrounds just sitting there and judging you and the statistics the way that they are, probably people who were male, white, CIS just sitting there and judging you as I was like a person of color just asking for money. Those are the biggest things that I wish that I knew.

“I wish I knew that I belonged here and I didn’t have to continue to try and prove myself everyday. When people give me a compliment, that they mean it. I don’t have to deconstruct it. They were happy with my work and I don’t have to find reasons that they shouldn’t be. I wish that I knew not to be so afraid of losing what I have in working here, and that a risk is worth taking. That it’s really, really, really hard to take when you know what you can lose.”

I’m from Dayton, Texas.

What were your early years like?

My early years were awesome and full of fun stories. I was adopted by my Aunt and Uncle. They separated when I was 12, so through that unique family setup I have 6 sisters and 2 brothers, either half-, step-, or through adoption. My parents were Pentecostal Evangelical Preachers, so I grew up really super religious, sheltered, not that many friends. I came out when I was 13 which was pretty crazy, going through all the stuff that was related to that at a young age in the middle of nowhere in Texas.

I’m curious what it was like in your experience being a gay guy growing up in Texas.

Small town, hyper-religious Texas! I don’t know how I managed to get out unscathed. I came out in school when I was 13, and I think back to what we were talking about at the beginning: having dangerous overconfidence and doing things without thinking was just what I always did. I remember watching Queer as Folk and thinking “Oh, I like guys, they like guys… Oh, I’m gay. I get it.” And I didn’t really think about the consequences but I came out to my friends. Since I lived in backwoods Texas, I was made fun of daily by students and teachers at school, and I was really, really depressed and suicidal at times. My Mom didn’t really know what to do with me during that period but she did tell me that things will get better which was definitely true. It just required moving out of Texas as soon as I could. Some of the people that bullied me have reached out on Facebook to apologize and I always tear up when I get these types of messages and struggle with what to say back, but I always respond and thank them for reaching out.

How did you first get interested in tech? I didn’t know about tech growing up in tiny little south. How did that get on your radar?

Yeah. That’s a really good question. It involves Björk, Spice Girls, and my mom ordering a computer from one of those mail-order catalogs and AOL [laughter]. Oh and it also involves Buffy the Vampire Slayer; Spice Girls, Björk, and Buffy the Vampire Slayer.

My mom got a computer and then we also got dial-up AOL and at the time there were a lot of services like Angelfire and Geocities. My first fansite was for the Spice Girls, and that was the first year. I made an Angelfire website about how much I loved the Spice Girls. I was just like, “I’m making a Spice Girl fansite.” I was obsessed with Ginger Spice, and there were a bunch of other fan websites, too. I was just like, “How did they make these? These are so cool. I have to learn this.” I would collect all my favorite images and upload them to my fansite, and then the next year I had a total shift from pop stuff to Björk and Buffy the Vampire Slayer. Then I made a Buffy the Vampire Slayer fan site and then I got a personal website where I put up poetry that was based off Björk’s music and photographs I had taken.

That’s how I got my initial taste of digital design, and then I just always did it. In high school, I had moved to Salt Lake City my senior year and they had a lot more classes to offer, like a web design class that I took. The LGBT Center put out a note to any teens that wanted to do web design that there was a multi-media company looking for help with a website for an anti-smoking campaign targeting teens. I volunteered and ended up getting a half year long web apprenticeship from it.

Cool.

So during that, I did my first professional website where I designed and coded it for that project for the Health Department, and it won an award that year at the Utah Multimedia Arts Festival. And then after that I did some freelance design work, maybe for a Summer or two, then I collected all the stuff that I had done and printed it out and made a portfolio. A friend referred me for a position at a web development company looking for a junior designer so I applied, interviewed and got the job. I was so nervous; it paid 11 dollars an hour and to me that was so much money at the time.

So, it wasn’t anything I really thought about. I started doing it at a young age and it’s just kind of gone up from there. Now I’m at a large tech company, which is kind of crazy. And the caliber that they hire for there, I’m constantly reminded of every day, which leads to imposter syndrome, but that’s a separate topic.

Tell me more about what your experience is like being surrounded by Ivy leaguers, having never been to college?

I’ve definitely experienced Imposter syndrome and my manager has been amazing in helping me unpack that and work through it. I definitely go home and overthink everything I said or did at work. I constantly tell myself that I went through the same interview process as all the other designers at the company, and that a lot of people were involved in that process. I tell myself that I’m supposed to be here and that this wasn’t by accident. I told a co-worker who went to Princeton recently that I didn’t go to college, and he said, “I would have not known that.” That was awesome to hear. I’m starting to feel better about letting people know I didn’t go to college if it ever comes up. So with imposter syndrome I’ve come to refer to it as reverse ego and to tell myself that I’m thinking about myself way too much in a negative way right now. That’s really helped me snap out of whatever mind spiral I’m in, thinking about myself so much and thinking I’m not qualified to do this job. Framing it differently has really helped me recognize when my mind goes there, and to think the opposite.

It’s a testament too, good for you, if you were able to have that life, where you went to the Ivy Leagues. That’s awesome, but that’s not it. That’s not all it takes.

Where did you find your early support networks, when you came here?

In San Francisco? Oh, that’s a really good question. I had a childhood friend from Texas living in the Tenderloin and she was kind of like my San Francisco Sherpa. She took me to Dolores Park for the first time and she connected me to a lot of people for freelance work. And the gay community was definitely a good support network. That’s how I got all my freelance work. And that’s who connected me to a lot of jobs. I would post on Facebook that I was looking for freelance work and I would get a bunch of referrals. Actually an acquaintance in the gay community referred me to Facebook and that’s how I got my current job.

What are your biggest motivators?

This is a good question. I’ve never thought I was a good designer. I have this idea in my head of what a really good designer is and I guess my biggest motivator is trying to aspire to that. I have so much more to learn and so much room to grow. Another motivator that’s spanned over the past 10 years are the people that told me I wasn’t going to make it as a designer and also being told I wasn’t going to make it in San Francisco. I’ve learned that I love being told that I can’t do something, so that makes me try even harder and makes me even more motivated.

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

Working on traveling more! Right now I’m trying to learn French and reading some books about France and Paris, planning a trip there this summer. I have never left continental North America before so this is my first international trip. Being a contractor for a long time, you never get paid vacation, it’s always about finding the next gig or have a backup gig in case the current job ends early, there’s a lot of hustle involved. So trying to work on traveling more and taking time off work. I can easily fall into the rut of over working and never taking any vacation.

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

For the people hoping to get into tech, simply learn to learn and get into a habit of always learning something new and find opportunities to use your newly found knowledge. That opened a lot of doors for me early on. When I was 19, I taught myself CSS over the span of a weekend and then used what I learned the very next week by taking on freelance development gigs that required it. So you need to have hustle too. And also, if people tell you that you can’t do something, don’t let that defeat you; use that as your motivation. For the people in tech with similar backgrounds, hit me up, lets support each other!

Where do you see yourself in 5 or 10 years? And Is there anything you’re focusing on doing differently in the future?

That is a really good question. In 5 years, I hope I’m still at my current job. I’ve spent that last 8 years contracting, working at various places, which lead to learning a lot really really, quickly and I’m definitely grateful for those experiences. When reflecting on why I changed jobs so much in my 20s it was because there were always new opportunities,the grass always seemed greener on the other side. On a deeper level, it was mainly centered around being afraid of people getting to know the real me so I switched jobs/places a lot. I was kind of burned at my first job in the Bay Area; my manager would make fun of me to our coworkers. I would wear bowties to work, was younger and little more flamboyant. He would say things like, “did you see what the faggot was wearing today?” As someone who over thinks everything and is highly sensitive, when I learned about this, it was lighter fluid to the fire that is my anxiety. After contracting there, I was very closed off with the people I worked with from then on. When I was asked if I wanted to go with the team for dinner or drinks, I would immediately say no. I didn’t actually talk about being gay at a few of the places for fear of what happened at my first Bay Area job. I really cheated myself on becoming friends with some really cool, talented people because of this defense mechanism. When people would ask me if I had a girlfriend, I would just say I’m single. Now I’m focusing on allowing people to get to know the authentic, real me.

Instead of never talking about anything related to my personal/dating life at work, now when I go to lunch with my team I share about my awkward OkCupid dates and the crazy guys I meet, which is almost every OkCupid date.

So I’ve learned that you can’t make 10 out of 10 people like you no matter what you do, so you should just be yourself no matter what. So my plan is to stay at my current company for as long as possible, learn as much as I can and let the people I work with get to know the real me. I’m grateful to work for a company that encourages people to be their authentic selves at work. Also, learning how to stay put in an industry that has a lot of open roles and when you’re being contacted by recruiters everyday is really hard; it has become the norm to only be with a company for 10 months. What I’ve learned though is that the grass is NEVER greener on the other side and most the time when I switched jobs, I regretted it for the first couple of months. Focusing on working through whatever issues you’re having that’s making you consider changing jobs will make you grow and become a better person, versus not addressing issues and just finding a new opportunity. I’ve tested the old adage many times: “Wherever you go… there you are” and it’s totally true. As for 10 years, I’m not sure where I’ll be. A lot of my favorite mentors in my career completely switched industries halfway through their careers which I think lead to them being even more badass and creative. I’m not sure what my second career will be yet. One of my new goals is doing a project for Beyoncé at some point in the next 10 years though

I grew up in National City, about 15 miles north of the border in San Diego. It’s predominantly Mexican-Filipino neighborhood, which is great because our family is super diverse. Mexican, white, filipino, a little of everything.

I grew up poor with divorced parents, Welfare family, zero dollars. However poor we were, my family maintained strong values. Mom cared about church, the arts, and education. She wanted to see good in the world. We grew up with this contrasting view that from within a rough neighborhood people really believed the world is a beautiful place.

I moved to San Francisco for college to study industrial design. My dream was to make really cool plastic products. I knew I needed to be a maker. I had to go away to school because my sister was expecting her first child and needed space in the house to raise him. A mix of interest, affordability, and distance made SFSU the right choice. I had never visited the school or city. I just made my choices and packed my bags. That’s how my life in San Francisco got started—in totally blind faith.

What were your first years in San Francisco like? Were you at all cognizant of the Silicon Valley tech machine, or were you in your own academic world, or just trying to survive?

A little bit of everything you just said. When I first arrived, I was paying for my own education which resulted in full-time school and two jobs. I was working at Lori’s Diner serving burgers to drunk people on the night shift. During the week and on weekends I sold sequined cocktail dresses at French Connection. Looking back, I should have doubled down on school and not work. Sweat equity is all I knew. In my sophomore year of school, at the bottom of the recession, I needed to get out of the craziness that was two jobs and school, so I took a full-time product distribution job with Apple… and so it began.

Wow. So, you have gone from that to industrial design to startup land. Walk me through that whole winding course.

During the recession my school went bankrupt, cutting my program. I didn’t finish industrial design school, but I had gotten far enough to know something about the industry. I knew the different facets of the discipline and I knew I could hustle. I worked for the world’s leading industrial design firm, Apple Inc. I had a good job and school wasn’t really feeding me as much as work, so I took the path of growth and fully committed to work.

I had tunnel-vision for work. I worked as hard as I could to get promoted, get raises, and take over bigger parts of the business to the point where I was coaching new hires on how to optimize their warehouses and their workflows, how to save the company money, and how to just do smarter business.

Three years in, I got married and moved to San Diego. Within a year, I was divorced and on my way back to San Francisco. I was young and career thirsty, and didn’t want to have an ok life in San Diego. I wanted a great life in San Francisco. I’ve always been fiercely independent and felt that I had to defend that through career and identity.

Upon returning to San Francisco, I stayed with Apple two more quarters. I was going through a personal rebuild and wanted to continue to grow. I was recruited to join Tiffany & Co. by someone I admired, someone who I thought would build me up—so I took the leap. No more than a year in at Tiffany’s, an old colleague from Apple gave me a call. They had just joined the marketing team at a tiny startup called Square. I came over to the office for lunch, saw the electricity across the team, and knew I needed to join. That was the moment I got on the rocketship, so to speak.

So you were a very early employee at Square. What is it like going from little startup to IPO?

It’s kind of insane, and it’s hard to say succinctly. I was a 100th hire. I’ve worked on everything from support to product, to product marketing, growth, even HR. The company has grown from small and scrappy to a big global organization. My focus has always been to build the business, to work on undefined problems. I will say that every ounce of energy I’ve put into building the company is exactly what I’ve gotten out of it. I joined the company with the intent of building something good in the world. That’s still the goal and there is still a lot of work to do.

What in general have been the most exciting things about your work? What things were you really proud of and what activated you?

I’ve spent the past five years building tools for people who are not accounted for by standard banking systems. I’ve had the privilege of working directly with small businesses, getting to know them and their life stories, their philosophy, and their hustle and everything that they put into their business just so that we could build the right product for them. I have made connections with letterpress artists in Greenville, SC to surf shops in New York City to a family run bar in Austin, TX. It’s changed my view of what the American Dream is today. Small businesses are much like startups in the way sweat and scrappiness get the job done. It’s been such an important life experience that has colored my view of the amazing entrepreneurial world we live in.

Do you think you have some sort of quality, some sort of personality trait that has allowed you to take on, blind challenges? You just do it, and own it, and end up doing it really well. Where does that come from?

When you come from nothing, you have nothing to lose. Because I don’t have your typical pedigree, I have to maintain a constant state of learning. Beginner’s mind! I have design sensibilities, but I’m strong with business operations and strategy. I’m not an expert at anything, but I’m not allergic to anything either. If you acknowledge that, you ask the right questions, and you’re willing to learn while you’re making things happen. People around you will invest in you. People will answer the questions you have if you’re brave enough to ask them. Know that’s the hardest part, acknowledging what you don’t know and be willing to learn – it might also have something to do with the fact that I am an INTJ.

When did you turn your attention towards the community? You manage a really successful event in the tech design world. What was the impetus?

Community building, for me, is the idea that you can always build the city you want to live in. There is a lot of commentary on what’s happening in San Francisco—tech bros versus artists versus families. There are these stereotypes that the media loves to commonly use as if they’re not living in a city of diverse people with diverse problems and perspectives. I believe if you want to see more art galleries, you should open an art gallery. If you want to see more artists in San Francisco, you should definitely patronize artists. If you want to see more women in tech, hire them. If you want to build a community—a safe community where people can come and be their nerdy little selves and eat pizza and make new friends and wear name tags and talk about your ideas every month—you’ve got to kind of create that space for yourself if it’s not already there for you. Be the change! That’s what Designers + Geeks, the conferences, Room & Makers, everything I’ve had a hand in building has been in service of—building the community I want to live in.

Have you seen tech culture change since you’ve started your career, for better or worse?

There are more voices in the echo chamber than ever before. Headlines used to be about what people were doing to make the world a better place. What people were building. What people were enabling other people to do. At this point, I think tech press has taken this noisy turn to only comment on the bad, focus on gossip, and create this skewed celebrity of what people are here working on. The reality is that jobs are more exciting than ever. Technology is moving in exciting directions.

What has your experience been as a young lady in tech?

I’ve had life changing opportunities in tech. At the same time, I’ve faced outright sexism that has held me back in some ways. I went from growing up in poverty to a thriving career in fintech, and I am still pushing up against that glass ceiling. Tech has changed my worldview – I can do so much more now for the world in my career than other paths could have afforded. Building technology allows you to focus on what you value and create tools to amplify whatever that is. As a woman, sister, daughter, human, I have access to tools and intelligence that change the world—that is so powerful! We work with the world’s smartest people, which is why it is even more infuriating to see sexism and discrimination happen in the workplace.

When did you want to start investing more time in women in Tech?

When a woman invested in me! She was one of my first bosses at Square. She was someone who hired me knowing that I had no experience. There was an insane amount of work to do so she told me straight up, “You are smart, and you have a lot of potential, and if you work hard, you will succeed. But you have to work hard.” She totally took a risk on me. That was the turning point. After that, I felt that I had to pay it forward to other women with great potential.

In early 2012, we started the women’s group at Square. We hosted an event that celebrated women entrepreneurs inviting both colleagues and customers to join. We had women owned and operated businesses selling their goods, friends and family of Square shopping, champagne and cake. It was glorious! The event was particularly special because many of these women had never celebrated International Women’s day before and even fewer men had been invited to join the effort. It brought together our entire community to support and uplift women entrepreneurs. It was a small investment that would shape how collective Square celebrated diversity.

What do you think it takes to survive in tech?

It takes a sense of self. I acknowledge that the odds are stacked against me—and I use that disadvantage to fuel me and push me forward.

Survival, particularly for women, requires a desire to work really hard with a thick skin. When something unfair happens, take any disadvantage to fuel your own progress. Double down and work harder. Prove that you’re indispensable. Don’t let bias paralyze you. Constant friction is certainly exhausting, but does have a profound ability to shape strong character.

It was Maggie Mason who put it all into perspective for me. She asked ‘How local is your feminism? Is it for you? Like, do you want a raise? Are you trying to set an example for your company? Are you trying to turn the world around and really be a bleeding heart martyr for women? I think yes to all. I definitely want fair pay. I want to see change for all women. I think you can invest your energy at different levels at the right time on the right cause.

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

Excites – I’m excited about totally new technologies. VR and AR, consumer biotech, democratization of tools. There are new canvases for us all to work on. New worlds to be invented.

Frustrates – The noise and doubt in the media about technology companies. The comms industry pokes and prods at what the next ‘unicorn’ will be or who is failing or who is raking it in. None of that matters because the headlines do not push the work forward. It creates noise and distraction to those who are actually rolling their sleeves up.

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

There’s no doubt that growing up poor gave me a real sense of hustle. I have always been totally obsessed with money because we didn’t have any. When I was in elementary school I would make my dad buy me a box of candy from Costco, and then I would sell it at market price to all the kids in the neighborhood so that I could finance my own interests. That same hustle drives me today. I can wear a lot of hats at Square, I can run Designers + Geeks, I can plan cool product conferences, I have my art studio and practice, I can focus on feminist initiatives, and still build a happy home and social life. Growing up with nothing makes you want to make the most of any opportunity that presents itself.

Let’s see. How do you think women can be assets to each other in the industry?

Women have the obvious opportunity to build each other up. Investing in women is probably the highest yielding effort any of us can make. I fight twice as hard for women on my team because natural empathy doesn’t always exist amongst other leaders. I believe that men, women, grandmas, grandpas, people who are know, have ever met, or are related to women should fucking invest in women.

What are your goals for 2016? What are you working on, either for work or for yourself?

I am hoping to work on bigger problems, take bigger risks, fewer but more meaningful projects. I’ve just made the leap from leading creative strategy and operations at Square to work on poverty relief at IDEO.org. I’m moving from newly minted IPO to work with this amazing non-profit organization. I believe that we all have only so many working years, and when we can afford to, we should put those years towards the change we want to see in the world.

What advice would you give to ladies hoping to get into tech or those who are just getting started? What you wish you had known in the beginning?

I wish I had known that every skill within an organization can be learned. In the beginning, I totally worshiped my engineer friends. I saw them as next-level smart and failed to acknowledge that they were just humans with different skills. Skills that I could learn too. I went from business operations to HR to product to marketing to design—all skills learned on the job! If you’re just starting out, when you meet someone who you perceive to be smarter than you, try learning what they do and see how far you get.

My dad was in the Air Force from 1960 to 1962-ish, something like that. He was stationed overseas in England. RAF Lakenheath was where I was born. Height of the Cold War. They literally started building the Berlin Wall the day that I was born, so it was just completely crazy to be out there. Then moved back here. His people and my mom’s people are both from the Bay Area, so I grew up in Sunnyvale from 1963 on.

I got a chance to see Silicon Valley happening kind of all around us. It was literally apricot orchards when we moved in, and they were tearing down some of them behind us to build another house behind us and all that. Fast-forward all the way to where we are now, and I’ve seen—I don’t know—six generations of Silicon Valley happening around me. It’s been really fun.

How did you first get interested in tech?

Well, growing up in suburban Sunnyvale, basically everybody’s dad worked for Lockheed or Martin, or one of the other missiles-and-space contractors. When I was a kid, my dad did not. He was a psych major and he was a writer. And he had a hobby store and a bunch of other stuff. He went into tech writing when the hobby shop went belly-up, and he was really talented.

He was able to look at what people wanted to say in writing such that other engineers – and later on – end users could actually understand what it was. He wrote the basic programming manual for a bunch of the early microcomputers – first generation things that people grew up with. So I think he wrote Beneath Apple Pascal for Apple, one of the early TRS-80 books for Tandy, and the Atari 400/800 BASIC programming guide.

I was the kid that they got to type in all of the program listings for the Atari 400/800 programming book.  So I got one of the early prototypes and the draft of the manual. And I got to type it all in and make sure it worked.

I had things to say about the text, and they actually listened to me and put it in. At that point it was kind of like, “Okay, this is what I want to do.” And I’m– I don’t know. This is 1978-ish, so I might have been 16 at that point. At 16, you don’t know what you want to do. And having something like this just kind of fall into my lap was really amazing.

So I just kept working on tiny computers.  In 1984 I was the guy who swept the floor and took out the garbage for a small software company. In those days we manufactured floppy disks. We copied the disks, stick on the label, put the disks in the envelop, put the envelope in the shrink wrap, put the shrink wrap on the manual, get the manual out the door … that kind of software production.

And then their phone system crapped out, and I was put in charge of finding a new phone system. And along with the new phone system came a T1 line, and along with the T1 line came the Internet. And I got email working for everybody, and a Gopher server, which let us save a ton of money by downloading files instead of using Federal Express.

And let’s see, 94-ish, this thing called Netscape suddenly appears about a mile down the road from us in Mountain View, and we put up a Web server and I had half a T1 to just monkey around with.

Again, I was super lucky, but I guess ready to be lucky at the same time.  So I learned how to work on the internet and build Web sites. I don’t know, I had an affinity for it and I really enjoyed it and I enjoyed talking to people about it.

I’ve got no computer science degree—I have no degree of any sort.  I’ve got absolutely nothing on paper that says “you should be an engineer.” I spent almost 19 years at this tiny company that later on turned out to be a big piece of WebMD. And then I took a year, tried to go back to college, and it didn’t work out, but then Yahoo called. And I took it, because I had always loved Yahoo.

I was at Yahoo for 5 years, and I really think of it as the college experience I’d never had. I helped them open up a bunch of APIs, and we invented Hack Day while I was there, plus most of the concepts everybody now thinks of as “front-end engineering.” Along with a bunch of other people, at Yahoo I went from a webdev to an engineer.

And then after Yahoo I went to Netflix for about two years.  There I worked on the first iPhone and Android apps. Again, lucky. And in the right place at the right time, with the right kind of ignorance about how impossible it was to build Netflix on a tiny Web browser, so they let me run with it.

After Netflix a tiny startup, which was later acquired by Yahoo, and after that, Pinterest.  The recruiter called my home phone and I wasn’t really looking for work, but my stepdaughter heard me say “Pinterest,” and she started waving at me like crazy from across the room.  “Pinterest! Yes! Pinterest is awesome! You! Want! To! Work! At! Pinterest!” And they were in town so I walked down and interviewed, and got the job, first person hired to work as a full-time front-end engineer there.

And, you know– I don’t want to minimize the work. There’s a lot of work, but there’s also a lot of, I guess, just listening and being available and being open to things.        

Anyway, so I’m here. It’s a long story.

In the scope of your career what accomplishments are you the proudest of?

It’s always the thing you’re working on right now.  When I was at Yahoo, I got to work on the front page at yahoo.com which (if you were to total up the page views) was at that point the single artifact that more human beings had read since the beginning of time, the Bible included. And leaving there, I thought “I’ve peaked, that’s it. Nothing I do will ever be that big and that important, and seen by more people.”  But then you go to Netflix and oh my God, everybody loves Netflix so much. And then you go to Pinterest and oh my God everybody loves Pinterest so much.

It’s the thing that you’re working on right now, really. I love working on a product that real actual people know about. I don’t like the business-to-business stuff so much. I think that’s kind of boring. I like to work on a thing that I can show to my mom.

My mom’s 76 years old and I can say to her, “Okay, see, I made this thing that makes the words “Pin it!” appear on the New York Times website, and when you click it you’re running my code, and I’m helping you share what you found with your friends.”

Yeah, I love that. As someone who’s from a small town, no one really understands what I do now – or what I did when I was a tech – that’s nice to kind of have those brief moments where you work on something that people from home recognize.

It’s super hard to explain what you’re doing to build Web sites to people who don’t also build Web sites. And it’s really important to understand that because we live surrounded by that stuff, it’s “the industry.”  If you live in Hollywood everybody knows what you’re talking about when you say “the industry.”  And the same goes for Silicon Valley this is “the industry.” But “the industry” is a tiny little dot on the surface of a really huge planet.

Yeah. Let’s go back to the first Hack Day. What was that like?

So there’s this genius named Bradley Horowitz who is currently VP of everything social at Google.  But he was hired at Yahoo — I want to say 2004-ish, something like that — and he was in charge of the part of Yahoo Search — yes, don’t laugh, Yahoo used to have its own search, and it was groundbreaking — that found images and music and video.  And he hired this other guy Chad Dickerson (now CEO of Etsy) to come in and do this thing called Hack Day. (Chad had other duties of course, but the important thing as far as Bradley was concerned was to do Hack Day.)

Nobody had thought about what Hack Day really meant. It was totally internal, not a visible outside thing. And the first one was the sales and marketing group hack day.  Although I didn’t work in SMG, my manager at the time said “This is something you should get in on,”  because I had this  habit of making something during the week and showing it to an internal mailing list every Friday. And he said, “You should go do this thing.”

So I stole a day and I went over to Santa Clara, which is where Search used to be.  And I participated in it and I won an award and I have that award on my desk to this day. It’s a little gold bowling trophy made by Leonard Lin, with the day hack logo on it.

It’s one of the most important things that ever happened to me.  I won an award for using APIs. It’s a dumb little technical nerdy thing but– there are audiences and there are audiences. Showing something that you built in an 8 hour period with everybody else around you sweating away and working on it– that was out of this world. That was a bit more than 10 years ago, that was early December 2005. We did a quarterly Hack Day and special editions 20 or 30 times while I was there, and during that time in 2006, we did an open one on the Yahoo campus for everyone who wanted, and one later in London. Beck came to Sunnyvale, and played for maybe a thousand people, right there on the lawn.

If there’s one thing I’ve participated in that actually matters it’s the idea that making a computer program should be something that is applauded, and recognized, and shown in public. And that’s an amazing thing, it’s an art form that didn’t exist before. And we made that. Well, Bradley made that, and Chad made that.

That’s amazing. Etsy Chad?

Yes! Chad’s now the CEO of Etsy. We went out to London for the first international Hack Day in 2007 and it was just amazing walking around with him– and I must have been up fifty hours straight at that point. Didn’t sleep on the plane and got in there, and got lost, and finally found the hotel and just as I was going to fall in to bed, phone rings and it’s Chad. He’s like, “Okay we’re here, we’re going out, let’s go!” And we actually went out, and we were out for half a day more, stomping around Camden Yard and those places.  Chad’s a good guy. I wish he was having an easier time of it at Etsy, but that’s life in the big leagues.

I feel like you’re a treasure trove of stories from the earlier dot coms.

I try not to be too old and boring, and the guy who’s always talking about his stuff, but it’s important.

People have to understand that everything I did was already done before, and everything they’re doing was already done before. Things progress in a cycle.

Everybody feels like they got it first. No one’s ever had to deal with this before but you know, yeah, they have. My parents in the ’60s, when the Berlin Wall was going up, they were dealing with stressy things too.

I’m curious how that affects your work—there are young folks now who are building things that they believe that they’re building for the first time, when there was literally the same start-up with a different name, 10 or 15 years ago. That died at some point, and I’m curious just to know what it’s like, to be surrounded by that young optimism and enthusiasm, and to know that things come and go.

I love the youth and energy. I feed off it, I’m an energy vampire. It keeps me young working for these guys. I don’t know. If they suddenly said to me, “Okay, here’s a group of your fellow 55-year-olds. You have to go work with them from now on,” I don’t think I could do it. I really enjoy working with people who have fresh perspectives. It reminds me every day that I need to keep my own perspective fresh, you know?

I do my best not to teach, not to lecture. A lot of this stuff can’t be taught, only learned. If people have questions, if people want help, I like to think I can help.

I’ve seen amazing repetition. A long time ago, I want to say five, six years ago, I went and got an internet domain called Local Fu. And the idea was I was just going to build a Twitter mashup so people could tweet something important about a local venue, like “Okay, here’s how to park in Palo Alto during the day,” that kind of thing.

And like so many of my other internet domains, I got it, and I went and got the @localfu account on Twitter and I kind of messed around with it and got busy and forgot about it and let it go. The domain went out of registration.  And the day after the domain went back into the pool somebody else bought it, and they were immediately doing the exact same thing that I was going to build. And first thing I did is I went and I looked at their Twitter account, and their Twitter account was like @getLocalFu or @myLocalFu or something like that, and one of the first messages was “If anybody knows who owns the @localfu Twitter account, can you please have them reach out,” so I just gave it to them.

The other thing that – I’m hesitant to talk about it, there are a lot of people, fine up-and-coming young white boys who just got out of Stanford or Berkeley and they have bright ideas and they attract a lot of VC funding.  They have a disproportionate amount of power in the real universe because they have all this money and they have the attention of power brokers and kingmakers, and they do these really dumb things, like, did you see the billboards that AirBnB bought during the election?

Mm-hmm.

I don’t know, that particular group of people should not have that much access to power in the real world. They build a lot of the wrong things. There’s a lot of apps being built—specifically in San Francisco—and they’re catering to people who are also building apps in San Francisco.  I remember seeing a parody about an app where they would literally come to your house and put the food in your mouth. It’s like early retirement for hipsters.

Yesterday, I think, somebody published an article saying “We can fix the whole prison overcrowding and funding thing. We can take Soylent – this product that’s just all your nutrition in a bottle, so you never have to cook – we can just feed the prisoners Soylent, give them virtual-reality headsets, and pack ’em in like sardines. I don’t know if you saw that, it was this hilarious thing.

Soylent for prisoners?

Yeah. And it’s how we’re going to streamline the whole prison thing, and not question the whole idea that this many people should be in prison, or that there should be private prisons, or that prisons should actually make a profit.  None of those questions get asked; these are givens.  It’s the one thing I worry–I worry about the younger generation. You kids today. [chuckle]

Yeah. I feel similarly. And I’m, at this point, just a twenty-eight year old photographer.

Don’t get me wrong, tech is a blast. I could never do anything else. I could potentially get a job building fences, but tech is the only thing I can really do that’s worth anything. It’s the way that everybody can have maximum impact on the largest amount of people’s lives. Build something amazing that lets people communicate with each other. Let’s people find things they didn’t even know existed. It’s one of the reasons why I’m at Pinterest. (I’ve totally drunk the Pinterest Kool-Aid, by the way. I think we’re the closest thing there is to a way to easily find something you didn’t actually know you were looking for in the first place.)

I agree.

That used to be Google. And Google is not nearly accessible enough to people who don’t want to learn how to speak Googlish. We don’t want to learn how to think like a computer.

Yeah. In your experience, I love that you’re enthusiastic about what you’re working on, and I’m curious to know, as someone who’s seen so many cycles of tech, what is exciting to you in this batch?

We’ve dropped the cost of entry to nothing. If you were building Yahoo many, many years ago, you had to go to Fry’s and buy some computers and wire them together and stick in a rack, and then call up AT&T and have them plug all the stuff in. And all of that is gone now.

Now, a 13-year-old can do it. You can talk to Amazon or Heroku or whoever’s running your cloud, and pull it together and have something up and running in the space of a Hack Day.

The cost of failing used to be 100,000 dollars. The cost of failing is now under a buck. You can fail for free. You can fail as much as you want. I think the lower the cost of failure goes, the easier it will be for people who have no business doing this – people like me – to actually give it a shot. I think that’s the chief difference: this batch of tech can be made by anybody.

I love that. Slight segue: You’re one of several folks I know in tech who don’t have college degrees at all, and you’ve done really well for yourself. How has that affected your career over the years, for good and for bad?

I got laid off from WebMD after almost 19 years. We basically took over WebMD, and we gradually shut down the entire Santa Clara operation. There were 5,000 people working there when we first started talking to them. And gradually we merged and purged, and then everything got shut down. We were the last little bit left in Santa Clara.

I’d started as the guy who ran shipping and receiving and stuffed floppies into envelopes to where I was the person running the entire Web-facing front end of the practice management division of WebMD.  Going from that into “okay, now go find another job” in an industry that won’t talk to you at all if you don’t have a CS degree– that was a bath of cold water.

I looked and looked and nobody wanted to talk to me. I’m 42 years old, at the time, and at that point, in 2003, at that point the age discrimination thing hadn’t really reared its head. It didn’t really work that way at all. That’s a thing that started in about 2007, courtesy of Mark Zuckerberg, and I can go into lots of detail on that later if you want.

Yes.

What entered into it is, I was not qualified on paper to write C++, which is what people were hiring for at the time. The Web languages — HTML, CSS and JavaScript — that was not considered programming at all. That was certainly not considered computer science, and to this day there are lingering questions.

So I went back to school. I went back to school because the stuff that I worked on wasn’t considered engineering, and that didn’t happen until I was at Yahoo. (There was a small group of people that actually made the concept of front end engineering out of nothing at Yahoo. That’s another great thing that came out of Yahoo.)

And I looked, and I looked, and I looked, and I’m like, “Wow, I can sit down and write this stuff, but I didn’t qualify.” I seriously would not have been able to convince an engineering recruiting type department that I was someone that they would want to hire. Google was not existent at this point. There really wasn’t a thing called Google when I was looking. I mean, it was there, but it was four or five guys trying to do something.

So I was at San Jose State, trying to finish up a very old bachelors in psychology, and I noticed that there wasn’t a really good way to study for this stuff. They had put me into a bunch of low-level undergrad courses, you know, Psych I and statistics and things like that. I wrote a thing purely for my own benefit to help me study online, and I opened it up to some of the other people in my classes, and it’s a commuter college so there are older people in the college, and I ran into some 30, 40 year old people who were in there basically doing the same thing I was.

I said, “Hey, I made this thing to help me quiz and get ready for this stuff, so if you want to try it out, you can try it out,” and I gave it to them. What it was, was a collaborative way of generating practice tests. We would just grab questions that had been on various pop quizzes, put them together with three wrong answers and one right answer.

Then everybody would re-take these quizzes until they were getting perfect scores.  It took the questions that people were missing, and sorted them up to the top.

And what we discovered was when we got to mid-term time, the questions that had sorted up to the top over the course of the semester were all on the mid-term, and we knew all the answers.

I ran this thing for three semesters and left San Jose State with a 5.2 grade point average. It was crazy. I got As and A-plusses in everything, and everybody else who had used this thing also got a bunch of As. To the point where, I had the dean of the psych department and some professors gather me into an office and say, “We have to talk about this thing that you’ve put online, because it really feels like you might be cheating.”

I showed them exactly what it was, and they got to the end of it and they were scratching their heads, and said, “Well, you’re obviously not cheating. You’re doing very well, but everybody else who is using it is also doing really well, and it’s kind of breaking the curve for everyone else in the class who isn’t using it.  Can you do us one favor and take it down at the end of the semester?”  And I did that.

But when Yahoo called, I  actually had something to show them.  Now, keep in mind they were paying $70,000 a year or something like that, which was approximately half of what I made the last year at WebMD. But it was like, “Sure. Absolutely. I’ll jump in and do it.”

So, I think in a very real sense not having the college degree actually got me the job. Because I wouldn’t have been doing what I was doing, and I wouldn’t have something verifiably useful to show them. Does that make sense? That’s very roundabout and weird.

Yeah, no. It reminds me– I actually want to pull it up. There was a quote that I saw on Twitter that stuck with me recently. It said, “My career only makes sense in hindsight.'”

Yes. Yes, that’s exactly right.

Me, I have a career because people wrote books. I have a career because there’s a thing called O’Reilly books. They make books for people who make websites. I had a career because of the Perl Book and the PHP book, and the Javascript book. I have a career because of Douglas Crockford, who worked at Yahoo. He was there when I was there, and he wrote a book called Javascript: The Good Parts. I looked at that, and it finally started to click and make sense for me. Up until then, I was a Web monkey. I was doing what they told me to do, and I would type in the tags and see if it works. It was all very guess-and-check. I wasn’t doing original programming, at least not using Web tech, until then. It’s all those guys. It’s those guys, and it’s getting lucky, and it’s working hard, and it’s being ready for things.

I am so intrigued by the fact that you can identify the moment when ageism became the thing.

That’s easy. Ageism began when Mark Zuckerburg said the famous words, “Young people are just smarter.”  It was a large plenary lecture for a bunch of people at Stanford, plus the Y Combinator people. If you look at the people who were in the audience, there were eight companies at Y Combinator, and I believe seven of which are still in business and several of which are now public.

You can see a direct correlation between what Zuckerberg says and how they do things at companies like Dropbox. Dropbox is famous for the bro culture, and “you need to be 22, and you need to drink, and you need to be white, and you need to go, go, go, go, go, and there’s no life outside of work, and you need to live right there and you need to come drinking with them every night, and for God’s sake don’t be a woman, you won’t fit in.”

All of that stuff comes right out of that one silly lecture that he did.

And the goofy thing is, Zuckerberg (now at the ripe old age of 31) still has yet to retract it. I have never seen where he has actually said, “hey, you know, I was 22 when I said that, and maybe I didn’t have all the perspective I could have possibly had, and you know, upon reflection, I no longer believe that young people are ‘just smarter.'”

I mean, he’s massively successful. He was a 22 year old billionaire, and of course, he’s going to stand up and say what he says, but look at that.  “Young people are just smarter.” If you were to substitute the word “white” for “young” you would get rocks thrown at you, and for good reason.

Yeah. So how have you felt the ripples?

I have personally never run into ageism in the workplace, but that’s because I think I have a talent for jumping out before they’re tired of me. I have these little mini-careers. I’ll have a nine-month career. At Yahoo I had five different careers. I was always looking for something I could lateral into that might potentially get me some more money at Yahoo. At Netflix I had a couple of major things.

At Pinterest I’ve basically been doing the same sorts of things since the day that I was hired, but I think it was because we were such a tiny company, and you could basically pick out what you wanted to do and work on it. I’ve just kept working on it for the entire time that I’ve been here.

But I know lots of people who can’t get hired. If you work on Linux and Apache and MySQL and PHP, you may be labeling yourself as a dinosaur.  If you don’t have a pretty solid looking GitHub profile, if you’re not actively contributing to open source, if you’re not making something new that other people are actually working on, working with and using, that’s the kiss of death.

They’re going to find somebody who is younger and cheaper. They’re going to find somebody who does not know that he should not be working those 14, 16, 18 hour days.

I mean, you already know you shouldn’t do that, it’s terrible for you. It’s eventually terrible for the company. These guys who are 22, they’ve just been handed millions of dollars by the VCs, they’re going to find some 21-year-olds, you know, who can be counted on to just work and work and work  until the money runs out or there’s a pivot.

How do you feel that, aside from sheer experience, how your time in tech and your perspective brings something to the table in your work?

I think as we get older we become much better pattern recognizers. Your brain cells die off as you get older but the connections between the brain cells become more and more complex. Your executive function is generally more in charge and what I’ve noticed with experienced people– are you familiar with Malcolm Gladwell’s theory of Ten Thousand Hours of Practice?

Yep.

That’s actually a really good way of thinking about it. People who are experienced, especially in software, especially running big projects in software, you can explain what you want to people like this and they can immediately give you a quick yes or no, and tell you whether something like this is a good idea to even try.

The key is, you have to phrase the question in the right way to actually get an explanation that makes sense. You don’t really want a yes or no. What you want is a, “Yes and here’s how we’re going to do it.” The flat “no” is never useful, you never give a flat “no.” People hate that.

What I think older and more experienced people are better at is immediately saying, “Okay, if you insist on doing it this way, here are the pitfalls your architecture is likely to fall into.” And when you pick somebody up who’s got that kind of experience it’s exactly as if you’ve handed the problem to someone who has no experience, they’ve worked on it for six months, they’ve made all the mistakes, learned all the learnings and then they’ve gone backwards in time to the instant when you ask them to do the product and then say “here are the things we’ve learned.” You get that free with someone who actually has the experience. Does that make sense?

If you look back on the span of your career, are there any major lessons learned that just really stand out to you?

Very few regrets. I would not be sitting in this chair having this conversation with you if anything had gone differently. I like to think that I could have listened harder, been more aware that things were going bad at various points in the career. I mean making that sideways dodge into this-or-that mini-career a little bit sooner in a couple places might have been better smarter.

But I certainly don’t regret not going to college and grinding my way through a computer science degree in 1983 which would have been totally useless for anything I’m doing right now.  I’ve no regrets on that.

I don’t know.  I do wish that I had listened harder to some well-meaning people that have talked to me throughout my entire career. People have offered me great advice and I’ve just been too stupid, too busy, too old, too set in my ways to actually listen to it. I wish I had listened more.

And lastly, what advice would you give to folks who are hoping to get into tech?

First of all, be aware of what’s already happening around you—what you can do without money or a college degree. Don’t listen to anybody who says, “If you spend $10,000, I will give you the equivalent of the college degree or golden ticket,” or whatever it is. You could probably just jump in, jump in and start running at yourself.

Find the change you want to see in the world. It’s old advice, it’s the same advice. Find something that’s busted, that makes you angry, that you want to fix. Go fix it, go make it better.

Listen to people, listen up. But I guess if you want to fix ageism in technology, ageism– I don’t know, I thought for a while I was going to be the poster boy for ageism in tech– in, actually, electronic stuff, and I don’t want to do that to my personal brands. I don’t think ageism is a fixable problem, but I do think that basic diversity in tech is a fixable problem. We can easily get more women in tech. We need more women senior engineers, more women founders, more women money, more women CTAs, and underrepresented minorities as well. All of those people need better representation, and if we can fix those problems – which are fixable problems – you can hire 22-year old women, you can hire 22-year old men, and people from underrepresented segments.

This advice is especially important for people who want to build consumer products. If you’re not building a thing that 100% of the population of the world will eventually use and love, you are aiming too low.  And if the people who build your product don’t genuinely represent that population, you will never be able to reach them and your product will inevitably fail.  If your founding team is a bunch of 22-year-old white male Americans, you’re already at a huge disadvantage and you must take immediate steps to overcome it.

Yeah. I want to dig deeper in that for a second. Just based on your experience, having worked with many different teams and seeing how teams change over time, what have been the benefits that you see of incorporating diverse employees into product work, into the company?

I do the same talk at every Hack Day that I’m invited to present at.  The talk is always “How to Win at Hack Day,” and I’m usually speaking to younger people, people who are in middle school, high school, maybe college age. I give them the same piece of advice, and the advice is, “No matter what you do about the thing that you’re working on, be sure that you have women on your team. And not one. Have at least two. You’re going to work together for 8 hours, or 24 hours, or maybe 36, and you need to stay on task. You need good modeling for listening and communication, and it will be magically better if you have women on your team.”

But all I can really say is “It will be magically better.” It always gets a round of applause from the women in the room, and it works really well.  I say, “I will tell you this right now. The winning team will have at least two women on it.”  And 24 hours later, guess what?  The winning team stands up – it’s got at least two women. Every time I predict it, it happens. It’s magic.

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