For those readers who aren’t familiar with your stories, would you each share your background and how you got to what you’re doing now?
Russ [R]: I went to NYU to study fine art and was really into photography, installation, and performance art. Near the end of college, I made a portfolio site for myself, which was the first website I ever made. This was around 2005—prime Flash territory—and I used Flash and Dreamweaver to make the site; it was awful, but I became super obsessed with Flash. I made a Flash website for the band I joined in my senior year at college and that led to making sites for other bands and recording studios, which rolled into a short career in advertising.
Meanwhile, I was still playing in the band and we were touring and playing gigs. Making Flash websites on the side was a great way to earn money while pursuing music. That went on for a couple years until the band peaked and then lost its momentum.
Near the end of 2008, Liz Danzico was starting the MFA in Interaction Design at the School of Visual Arts. I heard the description for the program and suddenly realized it was everything I ever wanted to do with design. I had been unsatisfied with the ad work for a long time, but it was such an easy way to make money while I had been touring and recording. I decided to drop everything and apply for the MFA program; I ended up being in the inaugural class. After two years at SVA, I popped out on the other side and started working at Facebook.
Jessica [J]: I grew up in Pennsylvania and went to college to study art and at that point, I didn’t actually know what graphic design was. I found my way into the design program at Tyler School of Art, which I got into by the skin of my teeth. I was rejected from community college based on my portfolio (laughing), but the admissions counselor from Tyler recruited a lot from my high school and after my art teacher went to bat for me and gave a really strong recommendation, they accepted my portfolio. It was awesome because I didn’t realize how creative of a school Tyler was when I got accepted. It’s structured so that the first year is all foundation and the second year is experimental; I got to try glass-blowing, ceramics, sculpture, and other things.
At the end of my sophomore year, I had to declare a major. Earlier that year, I had taken a design class and discovered that that was what I wanted to do. I had felt like an idiot for not being able to do self-expressive artwork because I didn’t feel like my opinions mattered—I was only 19. Design allowed me to express other people’s opinions and problem solve, which made so much sense for me. I threw myself into the program, did a shit-ton of design work, and ended up graduating with the top portfolio.
After college, I worked for Headcase Design in Philly and then for Louise Fili in New York. It was there that I discovered my love of lettering. I didn’t realize that lettering was an entirely different industry that is very much aligned to illustration. I was doing a lot of lettering for Louise, but wanted to do more. I worked on incorporating it into my freelance illustration work and before long, clients started to take notice. I started getting a lot more freelance lettering work and once I became overloaded with freelance work and had a lot of side projects I wanted to work on, I gave notice and left my job with Louise.
I started Daily Drop Cap right after that because I knew that not all of my client work would be glamorous and fun—I wanted to have something that pushed me to better my lettering skills and gave me a reason to practice daily. I had no idea that the project would completely change my career by shining a spotlight on my lettering work. I had already been getting consistent freelance work, but I was just another illustrator. That project really made a difference and I started doing a ton of lettering work, which is now the primary kind of work I do for clients.
Since doing Daily Drop Cap, I’ve been totally geared about starting more side projects and have created about 12 or 13. Side projects have become a great way to flex my muscles in realms that I don’t get to enter for client work.
Ryan: You guys have worked on some projects together, right?
J: We’ve worked on two projects together. One was our wedding invitation, which was a huge project. Russ did most of the build; I did a lot of the design work and recruited friends to make artwork for it. I was essentially the designer and project manager and Russ was the architect.
The other big project we work on together is Don’t Fear the Internet—I sort of strong-armed Russ into doing that one with me.
R: It’s true. And now I’m the one that strong-arms her into keeping it up.
J: Yeah, now I’m dragging my feet. It takes a lot of time to do.
Ryan: Do you guys enjoy working on stuff together?
J: We do. What’s good is that we’re really different people in terms of our processes and how we work, so when we work together, we’re really good at editing each other. If we weren’t working together on Don’t Fear the Internet, it would be a totally different project. Russ is so good about making sure everything is precise and simple; but at the same time, Russ will say, “Let’s jump into responsive design,” and I’ll reply, “Dude, let’s make the links not blue and underlined first.” He’s so far down the line that he forgets about the little eureka moments when you’re first learning web development. I’m earlier in the process of learning how to do HTML and CSS and remember those moments a little more vividly.
Was creativity a part of your childhoods?
J: Definitely. My parents are not art people at all. My dad is a dentist and my mom went to school for chemistry. When I was growing up, my mom knew how much I loved to draw and she bought me endless art supplies. Ever since I was two or three years old, I would spent six hours a day drawing—I was just a super well-behaved little kid because I was always preoccupied with art.
R: My childhood was also pretty creative. My older brother was really good at drawing. Then I came along and was also good at it. We always drew together—comic book characters, animals. I also took art classes as a kid and went to camp for acting because I was into performance. I did some acting in high school and college and being in the band was an extension of my desire to perform.
I was always pretty good at drawing, but never great at being an artist. I didn’t know that such a thing existed that was a cross between science, engineering, invention, and art. I always assumed I should try to become an artist because I could draw well and that I wouldn’t use my interest in science and technology. I’ve finally found a very happy place between those two extremes and I feel very at home with what I’m doing now.
“When I was growing up, my mom knew how much I loved to draw and she bought me endless art supplies…I was always preoccupied with art.” / Jessica
Ryan: What about music? Is that something you did when you were younger as well?
R: Yeah, it’s a little embarrassing to say, but I was very into the Dave Matthews Band when I was in high school.
J: Who wasn’t!?
R: A Dave Matthews and Tim Reynolds acoustic album came out and I was so blown away by what they were doing with acoustic guitars that, of course, I went and picked up an acoustic guitar and started learning to play. So, yeah, music was a big part of my adolescent life and beyond.
Did either of you have an “aha” moment when you knew you wanted to pursue your particular career path?
J: Mine was when I was in college. There wasn’t necessarily one “aha” moment, but I found that I kept procrastinating and dragging my feet on painting and drawing assignments. I enjoyed them once I was actually doing them, but it took me so long to start. I would end up procrastinating on fine art assignments to work on design projects. For example, I would make six posters instead of one or do a ton of unnecessary iterations because I was having more fun doing design work. It was an “aha” moment for me to realize I should probably pay attention to the stuff I enjoy working on and guide my major in that direction. Now when I find myself procrastinating on something, I try to take note of it and use whatever work that I was procrastinating with to guide what I want to do next.
R: I had a similar experience. When I got out of college, I decided to devote myself to the band, but I was treating it as a design exercise. Being in the band scratched a lot of itches for me in terms of being able to perform, to write and play music, and to do all of this design work at the same time. One of the most exciting parts of being in the band was the prospect of designing a bunch of album covers and show posters, making t-shirts, and doing videos—all of the design collateral that goes along with being in a band. I was far more dedicated to staying up until 4am to design a new website or posters for the band than I was to rehearsing the songs or improving my ability to play the guitar or keyboard. I was far more interested in rehearsing design than I was in rehearsing music.
Did either of you have a mentor along the way?
J: I’ve had mentors every step of the way. Louise Fili was a huge mentor and I had teachers in college who were very influential. Over the years, I’ve relied on “design moms and dads” to help me, to answer my questions, and to give me guidance and advice. I’ve always been a small group or best friend kind of person—I find a connection to one or two people and then just spend all my time with them and that’s sort of how my college and employment situations have ended up.
R: Mostly no. I did read a lot—I would go to Strand bookstores in New York and read books about design—and I followed along with online communities, but it took me a long time to meet anyone in the design field. I studied fine art in undergrad and didn’t even know what design was when I graduated, nor did I realize that it was a profession with so many varied sub-disciplines. It was well into grad school before I felt like I actually belonged to a community of designers who were doing things I was interested in.
J: Yeah, Russ didn’t have any design friends before we were dating and even after we started dating, most of my friends were illustrators. Russ always treated them like my friends who he was getting to know, but he didn’t feel an immediate connection with them like the folks he went to grad school with. Also, I didn’t get hyper-involved with the web field until we had been dating for some time. Our web friends are our first group of mutual friends.
R: Yeah, and I didn’t have any ins to any of these very strong, very connected web and tech communities. They always felt so remote to me. It never crossed my mind that I’d have a chance to meet Jason Santa Maria or Jeffrey Zeldman or any of these other people I followed. When I read the syllabus for the SVA interaction program, I was flabbergasted by the talent coming in to teach and more than anything, I was excited by the possibility of being able to learn from them and be in community with them because they cared about the same things I cared about.
Was there a point in either of your lives when you decided you had to take a big risk to move forward?
J: There were a couple for me. Choosing to go completely freelance was really scary even though I knew it was totally possible.
Another one was when I started to work for Louise in New York. I was living in Philly and had no plans to move. I had sent Louise one of my illustration promos just because I thought she was awesome. She called me for an interview, hired me that day, and I had to move to NY in three weeks. I hardly knew anyone in NY and I was absolutely miserable for the first six or eight months. I knew it would be amazing and beneficial to work for her, so it wasn’t a risk in that way, but it did put me hugely outside of my comfort zone. There were a lot of moments where I said to myself, “Man, why did I do this? Why don’t I just go back to Philadelphia where I have friends, where things are easy, where everything’s not so expensive, and I’m not sick all the time?” But I stayed and it ended up being so worth it.
“I didn’t know that such a thing existed that was a cross between science, engineering, invention, and art…I’ve finally found a very happy place between those two extremes and I feel very at home with what I’m doing now.” / Russ
Russ, did you take any risks?
R: For almost two years, I worked as a web designer for a small, Brooklyn based startup called Neighborhoodies. Then the band reached a point where we had just released a full-length album and made a music video with some Nickelodeon TV stars from the 90s. The video started to go viral on Youtube and the band was in a position where we needed to get out there and tour. In order to do that, I had to quit my job with only $1,000 in the bank and become a freelancer.
J: You’ve had a whole bunch of moments like that. Even when you started grad school—when Russ first started grad school, he would say over and over again, “Well, if something happens with the band, I’m just gonna have to quit school and go with the band.” And that changed over time to, “What was I thinking? Of course I wouldn’t leave grad school.” Then when he graduated, he got job offers at all these different places and it was fucking terrifying to make a decision because everything felt like a risk—it was his first big job in a completely new field—and the offers were so varied. He was trying to choose which environment would be the best for learning and what would make sense financially.
R: Yeah, I have had some crazy moments. The last few weeks of grad school were wild for me. Not only was I on the verge of presenting my thesis, which I had worked on for a year and a half, but three days before I gave my presentation, Facebook wanted to interview me. I flew out to San Francisco to do a full day of interviewing and then flew back to NY the same day. A few days before that, I had actually proposed to Jessica, which was a big, nerve-wracking thing for me because I’m totally neurotic—
J: And because you knew I would say, “No.”
R: But it was funny because I wasn’t able to reach my parents after I proposed to Jess, so we couldn’t announce it on the Internet yet. Then I flew out to San Francisco for the Facebook interview and was sitting in the Facebook parking lot in my rental car, five days after I had proposed to Jess, when my dad finally called me back. I said, “Hey Dad. Yup, I’m in the parking lot of Facebook getting ready to do an interview; I have my thesis presentation in a few days; and oh, by the way, I’m getting married.” There was a 20 second period of silence before my dad responded.
Jess had planned this short getaway to Paris for us, so after I did my thesis presentation, we went there for a few days to celebrate graduation and our engagement. I essentially had three job offers on the table to choose from: Google, Facebook, and a startup that I had done freelance work with over the past year. We spent more than half of the trip totally freaking out about my decision. What’s funny is that I made the wrong decision and joined the startup.
J: We were in New York, so we had no idea that when you come to San Francisco, literally every human being is in a startup. It seemed like such an opportunity, but really, Russ could’ve come out here, walked into a coffee shop and said, “Who’s hiring?”
R: Yeah, so I chose the startup and said no to Google and Facebook. I flew out to meet the team and realized almost immediately that I had made the wrong decision. The most important thing is that you care about the products you’re building, not the lifestyle or how many employees the company has.
J: And also, your only experience with the product world had been at grad school. Being the only designer at a startup, you wouldn’t have mentorship and you still wanted to learn a lot more.
R: Yeah, there was a lot more I wanted to learn about creating products. I knew that I could learn so much more from the design team at Facebook than I could going it alone as a sole designer. Most importantly, I cared about Facebook as a product. So I very quickly changed direction, apologized profusely to the startup, and ended up at Facebook. There was definitely a crisis moment when I misjudged my priorities, but I managed to bail myself out.
Tina: You two have been dating for a few years, right?
J: Almost four years.
Tina: Would the move to San Francisco be the biggest risk the two of you have taken together?
J: That was a huge ordeal.
R: I thought Jess was going to kill me.
J: I had a meltdown on the street, actually. We were going out to brunch and I had been super passive-aggressive toward Russ for the past two weeks. He had three job offers and all of them were in San Francisco, but Russ didn’t want to jinx it by saying we were moving there. I was in this weird limbo where I knew that we were moving, but Russ wouldn’t tell me we were moving. So, we were walking to brunch and I was being really silent and Russ was like, “You have to stop. Talk to me about what you’re feeling,” and I just started bawling immediately.
R: Right in the middle of the sidewalk—tears streaming down her face. We talked it through and for her, it was more that she felt like she couldn’t express that she was unhappy about it.
J: Well, yeah, the biggest thing was that I felt like I couldn’t have an opinion because I knew how good it was for Russ’ future that we move. I can work from anywhere because I’m a freelancer—my clients aren’t location specific. I felt like I didn’t have a say because any sharing of my opinion of wanting to stay in New York was entirely selfish. I also felt selfish because I knew it was so good for him, but I didn’t want it to happen. I couldn’t make him stay and I couldn’t choose NY over our relationship, so it was a very conflicting time.
When Russ had interned at Apple the year before, I had went out to visit him and had a really funky opinion about San Francisco. We just didn’t know anyone there and I have such a huge posse of friends in NY. I had 15 friends who worked in the same building as me and I liked my commute to the studio. In 2008, I bought an apartment in NY and hadn’t planned on moving anytime soon. It was a major life switcheroo.
Once we got out here and I realized what San Francisco was really like, seeing it not just from my perspective as a visitor, it was totally different. I think it would have been super scary moving if we hadn’t had the apartment in Brooklyn. I made Russ promise that if I absolutely hated it, we would move back, but that hasn’t happened yet.
Read part two of our interview with Jessica and Russ.