Let’s start at the beginning. Tell me a bit about your early years and where you come from.

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.”