Would you share your story about how you got started in design and development?
I think I’ve always been interested in design. Early on in my life, I didn’t really know what that meant. As I look back now, I was always interested in brands, logos, and the way people portray themselves visually. To preface all of this, I don’t have formal training in design; I didn’t go to school for it.
I came about this in a weird way. I was a musician and that’s all I wanted to do for a long time. I played drums and guitar in a few bands toward the end of my early twenties. Back in 1997, I was making minimum wage working at a record label called Rounder Records in Cambridge. I didn’t even have a computer at home because I just couldn’t afford it. I was packing CDs in the warehouse most of the time and then I finally got a desk job and a computer with Windows 3.1, which connected to the web.
It was amazing to discover this whole world out there and I was immediately taken with it. I loved that the web connected all these different things and interests and pulled them together. I mentioned earlier that I’d always been interested in design, but didn’t know that I was. It was the web that exposed me to design—out of necessity—because I was trying to teach myself to build websites and when you design your own site, you’re the creative director. It doesn’t matter if it’s a one page site that nobody’s going to look at.
Eventually, I got a computer at home and spent many late nights learning HTML. That’s how I got into it. Everything clicked at that point. It wasn’t like music; I knew I wasn’t going to be a rock star and I had to come to terms with that. I thought that maybe I could enjoy design and make a living doing it; I was sick of packing CDs at that point.
Ryan: Do you think music influenced you? I have a music background and a lot of the designers we’ve talked with have also been involved with music.
Yeah. I think so. It does seem like there are a lot of musicians who have gravitated toward design, especially web design. Why that is—that’s a good question. For me, music was sometimes frustrating; it was hard to be creatively satisfied without getting others involved. I was so driven to do music for a long time, yet it was a difficult process. With design, you have more individuality and control over the creative process and I think I took to that immediately once I realized I could see something through from start to finish by myself.
I still love playing music and I always will play it, but in terms of being happy with a creative process, it’s easier for me to be fulfilled creatively with design. I love that about it.
Once you started teaching yourself, did you immediately start your own business doing freelance work or did you work for others first?
It took a while. I left the record company and went to work for an internet service provider doing support. (laughing) I was as low on the totem pole as I could be. I felt like I didn’t know what I was doing and I had a lot to learn about how the web works—I mean, really basic stuff. Working at an ISP was good for that because I got to learn the basics of how things work down to a connection level. Eventually, we did start doing a little bit of web design there and I got to work with a few clients.
That led to another job at a dot com called MyWay in Boston. It was right before the dot com bust. I got in at the last second and was probably their last hire. A month after I started, the CEO was fired to “spend more time with his family”. My boss there went on to work at a place called Fast Company—they’re still kicking and doing some pretty good stuff.
I was one of the last people out of MyWay.com and my old boss recruited me to come work on the web team with her at Fast Company. That was the best thing that ever happened to me. It was the beginning of the web standards movement. Right after the wired.com redesign, which was a watershed time for CSS, I told my boss, “We gotta do this. We have a lot of similarities. We’re both magazines; we’re both in publishing. We have to go into this web standards stuff.” I had been dabbling in it on the side and luckily I had a boss who was great and said, “You’re right; we’ve got to do it. You go for it and lead the charge.” Man, it was such an opportunity. We did it. We did a CSS redesign for the Fast Company site.
I was also writing on my blog, SimpleBits, at the time and I was documenting the process there. That helped me out and propelled me career-wise to have something very public at a time when there was a lot of experimenting going on.
After that job ended, I started freelancing. The company moved to New York and although I love NY, I didn’t want to move there. That was about nine years ago. At the time, I didn’t want to freelance, but since I didn’t take the job in NY, I was laid off. A month went by and I got a client and then another month went by and I got a few more. ESPN was one of my first clients, thanks to Mike Davidson—I was ridiculously lucky. That contract lasted for six months, which got me into freelancing. From there, I haven’t looked back. I’m probably unemployable right now. (laughing)
Tina: Are you originally from the Salem area?
I’m New England born and bred. I was born in Massachusetts and grew up in Vermont. My family moved to Needham, MA when I was a freshman in high school—it’s a suburb right outside of Boston. I lived in Boston and the surrounding area for a long time. My wife and I moved to the Salem area twelve years ago because it was too expensive to live in Boston, but now we love it here. It’s on the ocean and close enough to the city, but it has its own downtown area. We’re happy here.
Was creativity a part of your childhood?
Always. It’s funny looking back on the things I was interested in—first, it was The Muppets. This is going to be a weird interview. I was into performance and my cousins and I would put on shows with puppets. Then, I was really into breakdancing for a while, which is absurd because I grew up in Vermont where there was no breakdancing. We’d have to bust out the cardboard.
I was talking earlier about being interested in design, but not knowing it. With anything I was interested in, I was always into the packaging of things, both physical and non-physical. Like with breakdancing, it was graffiti and we’d practice drawing bubble letters on cardboard. Then I started getting into music and had a little band when I was in 7th grade. We tried to design our own covers and cassettes. Another interest was skateboarding, which is a huge design thing—all the brands, the graphic designs on the boards and shirts and stickers. I loved all that stuff. I wish I’d realized sooner that you didn’t have to pretend to be in a band to design something.
Both sides of my family are very musical and there was always music playing. That was also a big part of my childhood.
Did you have a real specific “aha” moment when you knew design was what you wanted to focus on?
Yeah. I’m trying to think if I can define that moment. It might have been on that Windows 3.1 computer at the record label. Seeing the web and how design can play a role in that—I think that’s when it clicked. From that point on, I focused on it and did as much as I could to learn about not only building websites, but design as well. I got into typography and all the stuff that goes along with design.
You said you were self-taught, but did you have any mentors along the way?
I did. There was a guy at the ISP I worked at—I’ve never mentioned this before. The ISP was called Galaxy Internet Services; they might still be around. The guy’s name was Paul Yasi and he was the web master at the ISP. I thought he was incredible. I remember seeing him use the command line to FTP files and thinking, “Oh my god, he’s talking to the computer! He can type something and tell it what to do and it’ll say something back.” I had no idea how any of this stuff worked and I decided I had to learn everything I could from him. He taught me a ton about computers. He probably doesn’t know this, but he was definitely a big influence on me.
Jeffrey Zeldman has long been a mentor as well. He’s been an inspiration and encouragement in my writing and speaking over the years. For that, I am deeply grateful. I wouldn’t be where I am without his web standards trailblazing.
There was also a guy named Davo—his full name is David Searson—at Fast Company. He was an Australian and was the head of the web team. He was a real mentor to me in regards to his philosophy, which was to stay as simple as possible. He loved Perl and wrote a lot of things with it. He was more of a programmer and I learned a lot from him about how systems should work. For me, he helped take a lot of the mystery out of the way web applications work. I realized anyone can get in there and duct tape something together that works.
Ryan: Was he the one that gave you the go-ahead to redesign the Fast Company website according to web standards?
Davo was behind it for sure, but it was more my boss, Rob Roesler, who I credit with giving us the okay to do it. I’m still friends with Rob. I owe him a lot; that was a pivotal moment for me to do something that so many people were going to see at a time when there weren’t a lot of large sites being designed that way.
Was there a point in your life when you decided you had to take a big risk to move forward?
Design-wise, it would be when I got laid off from Fast Company and started freelancing. It wasn’t intentional, but I had to pay some bills and thought I should take on some projects. It wasn’t that one day I decided to take a leap and do that—it was more of a gradual thing.
Another one would be the first time I had to speak about web design. I was terrified and still get terrified. It’s not something I ever thought I would do, but because of the stuff I was writing about, I got asked to speak. The first time I spoke was on a panel at SXSW. Christopher Schmitt put it together and it was Dave Shea, Doug Bowman, and I. It turned out okay and I made it through without collapsing onstage. It was just bizarre to me because I hate public speaking—did I just say that? (laughing) But I’ve learned to be okay with getting up in front of people and talking. Long story short, that was another pivotal leap. I think that was more of a risk than anything else.
“There was so much knowledge sharing going on and people were building on each other’s work. We helped each other out. I didn’t think of myself individually as contributing all this stuff; it was more about helping the greater cause of web standards…”
Tina: This isn’t on our usual list of questions, but I have to ask—when you were doing all of this work and documenting it on your blog, did you realize the impact it would have?
That’s a good question. I think I did a little bit, only because there wasn’t a lot happening on a very visible level regarding commercial websites. There was Wired, which was the first big one; Doug Bowman was the reason for that. ESPN was also doing some stuff with web standards.
Back then, it was especially fun because it was really new territory. I kinda miss that. People were starting to blog about it and were discovering and sharing different techniques every day. On that level, I thought we were doing some cool stuff, but it felt like more of a community effort. There was so much knowledge sharing going on and people were building on each other’s work. We helped each other out. I didn’t think of myself individually as contributing all this stuff; it was more about helping the greater cause of web standards and proving a point of how things could be done better moving forward.
Are your family and friends supportive of what you do?
Definitely. I was fortunate that my parents have always been supportive of anything—almost to a fault, in a way. It was like, “Oh, you’re going to be a musician? Sure. Oh? You’re going to drop out of college and go to music recording school? Okay.” My parents have always been so supportive and I really appreciate that.
Now, my wife and my kids are the focus and they’ve been supportive as well. A lot of this weird career path stuff has happened over the last ten years or so, which is the time when I’ve been married and had kids. To be able to balance those two things, you have to have a supportive family. When I have to go speak somewhere and Kerry has to be home with the kids by herself, it’s difficult. It’s getting easier now that the kids are older, but I’m thankful to her for allowing me to do this.
Ryan: Now, you’re doing Dribbble full-time right? Do you get more time with the family now that you’re focused on one thing?
Yes. That’s been great. It’s funny—when you’re freelancing people say it must be great being your own boss, but really, you have five bosses because maybe you have five different projects going on. Those people are bosses, but usually there’s no personal connection. Whereas, if you’re working at a single job and have one boss, you get to know them and they get to know you. You can tell them you have to leave work to go to a doctor’s appointment with your kid and they understand that. With freelancing, it’s difficult to do that. You’re the business hired to do the job and there’s a lack of personal connection. That’s one of the things I didn’t like about freelancing.
While we’re talking about Dribbble and that creative community, is being part of a creative community something that’s important to you?
Definitely. Like I was saying about the early CSS days, I owe everything to the community as far as being where I am. Before, it was blogging. That was the only way to communicate with web people. I’m still friends with people who I connected with through blogging back in those days.
Seeing a community form around Dribbble has been awesome. One of the things I love the most about it is that it has shown me people I didn’t know about before. In a way, I feel like a little bit of an outsider because the talent is so incredible.
Community is great for building confidence, peer review, critique, and knowledge sharing. All of that is important, no matter what you’re doing or what community you’re a part of.
Do you have a community in Salem that you’re a part of?
Yeah. It’s not a tech-hub here, but there is a web scene. There’s a group that meets once a month called the Build Guild, which I don’t go to enough. I also occasionally go to events in Boston. Salem has just enough to feel like I’m tapped into something, but not too much so that I feel overwhelmed and can’t focus. I’m a little bit of an introvert, so it’s helpful to be in a place that isn’t so bustling with activity.
Do you feel a responsibility to contribute to something bigger than yourself?
I think I was scared of this question because it made me ask, “What am I contributing?” I want the answer to be yes.
One of the things I feel good about is when I go to a conference and meet people from different parts of the world and they say how Dribbble helped them get a job. That’s a specific example, but it’s cool because, yes, Dribbble is a site that you put screenshots on, but it’s helping people in small ways. It’s not putting a dent in the universe, but it’s creating a ripple.
I don’t know if that’s the end game. I’d like to think there’s something I can contribute that’s even more substantial, but I don’t know what that is yet. I enjoy helping people understand things. I wouldn’t say teaching, but I guess through writing and speaking, it is sort of like teaching. I also enjoy helping people get excited about things and I guess Dribbble does that in a way. I do hope there’s something larger looming. I’m glad you asked because it makes me think there’s got to be something more. I’ll keep you posted.
Are you satisfied creatively?
I’m getting there. I think it’s interesting because I’ve been full-time on Dribbble for five or six months and I feel closer to being satisfied because of that focus. I loved parts of freelancing, but at the same time, there are cons. Even though Dribbble is only one site, there are so many outlets attached to it. There are a lot of other things we could do with it. That’s fun to think about. It’s like having a brand to play around and experiment with. To answer your question, I’d say I’m sort of satisfied. I think I’m on the right path.
That said, is there anything you’d like to see yourself doing in the next 5 to 10 years?
I’m pretty happy with what I’m doing day-to-day. This is going to sound corny, but I think maybe I’d like to not be working as much. I’d like to be able to spend even more time with my family. Going back to my freelance era, there was a lot of stress involved. I’d like to be satisfied creatively, but also not have work take up 18 hours of my day. I’d like to have the best work and life balance possible.
If you could give a piece of advice to another designer starting out, what would it be?
Don’t be afraid to be what you want to be. If someone had told me twenty years ago that I was going to be doing all these things, I would have said, “You’re kidding me. That’s not me. Other people write books; other people speak; other people design things.”
Maybe it goes back to not being formally trained, but I always had this inferiority complex. I thought I was going to be outed as a non-designer and that someone would say, “Wait, he’s not really a designer. He’s not part of this club.” That isn’t true. The difference between someone who is a designer and someone who isn’t is simply that a person who is a designer has done it. My advice is don’t get hung up on labels or position or titles. It doesn’t just happen; it’s a gradual process. You can’t be afraid to jump in there and start doing it.
What does a typical day look like for you?
I get up at 6:30 or 7am when our kids wake us up. Unfortunately, I have to grab my phone to check in and see if there are any fires that need to be put out on Dribbble. That’s the downside to being a small operation, but having a large site that people are using while you’re sleeping. Actually, Rich, our co-founder, has it worse because he gets these alerts when something goes down.
Anyway, I wake up, check my phone, get some breakfast, and take my son, Jack, to school. If it’s nice enough, he’ll ride his bike and I’ll ride my scooter. Then I’ll go home, get ready for work, maybe play a little banjo, and walk five minutes to the office. I work for a couple hours, get a burrito for lunch, then work for a few more hours—this is actually pretty boring. (laughing) I end work about 5:30pm so I can go home and have dinner with the family and get the kids to bed. Depending on how that goes, I’ll have a little Scotch and some TV time with my wife. Man, that’s pretty uninspiring, really.
Tina: We just want to make sure that other people aren’t having more fun than us. That’s why we ask this question. If someone else is having more fun, we’re going to change professions.
So it’s research? I see. Yeah, that’s it. I tried to think of things to make my day sound more interesting, but I’m not going to embellish it.
(This is where Ryan and Dan have a side conversation about Scotch)
Any favorite TV shows or movies?
Like everyone else these days, we’ve been getting into TV more. It seems like it’s hitting a renaissance. There’s so much to watch. It’s the usual suspects: Downton Abbey is good; I love the Battlestar Galactica series; Breaking Bad; Mad Men. That’s pretty typical, isn’t it?
The last movie I saw was a documentary called The King of Kong. It’s about the Donkey Kong world record and the guy who has held the title since the early 1980’s. This normal guy buys the game, puts it in his garage, and sets out to beat the record while driving his wife crazy. I don’t want to give it away, but it becomes this tragic tale. It’s incredible.
There’s a similar documentary that has some of the same people in it. It’s called Chasing Ghosts: Beyond the Arcade.
Any favorite albums?
I’ve been listening to this band called Best Coast. It’s really retro and the vocals are awesome.
I’ve also been learning banjo recently, so I’ve had banjo stuff on repeat—mostly this one album by Reed Martin. He’s in his sixties and played banjo his whole life while flying under the radar. He’s incredible, but never became famous. Then, ten years ago, he recorded an album of all the songs he knew and it became this highly revered work because of his style on the banjo.
Do you have any favorite books?
I have not been reading books enough recently.
How about books you read to your kids?
That’s what I would have to say. It’s hard to find time to sit quietly these days. By the end of the day after the kids are in bed, we’re spent and just want to watch something on TV.
I could try to sound cool and make something up? I’m thinking of kid’s book. Oh, Elephant and Piggy is a hilarious series of children’s books. I don’t know if that counts.
That would be burritos for sure—a burrito of any kind. There’s a place that opened near the office a year ago, which was a big deal because Salem isn’t burrito country. It’s a real taqueria and it’s dangerous because I go there all the time.
“The difference between someone who is a designer and someone who isn’t is simply that a person who is a designer has done it. My advice is don’t get hung up on labels or position or titles.”
We’ve got one last question for you. What kind of legacy do you hope to leave?
Oh, yeah. That one. Dammit.
Maybe it’s not a bad thing to say that I don’t have a giant grand plan. I tend not to look too far ahead. It’s hard for me to project that far into the future. I guess the easy answer is that I hope to have helped people be creative. I think that could mean something larger later on; I just don’t know what that is yet.
Of course, that would be a professional legacy. I guess, in terms of legacy, my kids would be the most important. Having kids has changed the way I think. Before, I would have said something like, I want to be successful and do something giant. Now, the focus is on my kids and making sure they do what they want to do. If they’re happy, then I’ll be happy. I want to make sure they can be creative, not necessarily in a design sense, but in a life sense. I think if you’re able to be creative, you’re usually happy. If I can help people, including my children, to be creative, then I know that in some way, they must be happy. I think the two go hand-in-hand.