It seems you had a very early start in the world of programming, particularly mobile app programing. How did it begin?
We got a family computer when I was 7 or so, so I grew up using it all the time. I was also really into podcasting really early. In 2003 or so, I was one of the first teenagers to start podcasting. In order for me to do that, I needed to figure out so many things like installing MovableType, running MySQLs, those sorts of things. And those skills started to build on top of another. I was also following so many programmers and designers. I was really impressed by these people who built the systems I was using to run my podcast, and I wanted to try building things myself. So I took two classes in high school, which brought me together with a bunch of other kids who were also trying to get into software development.
I got the first iPhone on the day it came out. The summer after, the App Store was live, and I was dying to build something for it. I knew I couldn’t do it by myself because it was too scary, too big. So I recruited my friend Brian Capps, who was one of the smartest kids in my high school. I said, “Hey Brian, I have an idea for an app.”
It was an app that showed Broadway showtimes. I was a theater kid, a Broadway nerd. I wanted to build a simple app that would show me what shows were playing. And that’s what Brian and I built.
I was amazed by the technology that suddenly became accessible to me. I thought in our lifetime, this is one of the pieces of technology that will be seen as a turning point, that everyone has this incredibly capable and useful thing in their pocket all the time. It was a powerful communication device at the same time as a powerful computation device, and that was just so incredible and inspiring. There was nothing else that I wanted to do other than make stuff for this new thing. I knew very quickly that everyone would fall in love with it.
And that lead to your software studio, Lickability. Tell us about the team and the products you guys have built.
Brian and I started the company a few years ago, and then later brought in one of my college roommates, Andrew. We all started out having a day job, but Brian is now full-time. All three of us have worked for the New York Times. It was my first real job as an engineer and I stayed there and made many friends until I moved to Tumblr. Andrew still works there. These people I work with are my two best friends in the entire world.
At Lickability, we have shipped three apps so far. Quotebook is an app for collecting quotes that matter to you, and Accelerator is an app for speed reading. We just released our third app, Pinpoint, which lets you mark up screenshots. It’s actually a remake of an app we ‘rescued’—an app called Bugshot by Marco Arment (who built Instapaper app), which had to be taken out from the App Store because it wasn’t supporting larger screen sizes.
Our values as a company are to build things that delight people, make them more productive, and make money. (As a small company with no investor, revenue is really important to us.) We think that we can still make a living by charging for software, which is considered a radical idea these days. We’re always asking ourselves, will someone pay for this? Is this going to make their lives better enough for them to be willing to part with a dollar or five to have it?
How did you get to work at Tumblr, and what do you like about it?
I’d always wanted to work at Tumblr. I admired David [Karp]’s product leadership as well as his design team from the point the product first came out. I think among the employees at Tumblr, I have one of the oldest blogs. I’ve been always looking for an opportunity to be a part of their team, but the right timing came a bit later. After some time, I’d had some experience working for the New York Times and Tumblr had an iOS team that was ready to bring on a new member, I jumped at the opportunity. I didn’t even have to think about it.
At Tumblr, so many people have these creative impulses. They are photographers, GIF artists, and fashion enthusiasts. For me, I mostly do the same thing I do at Tumblr—which is craft applications and mobile apps—in my spare time. I see others who are like me at Tumblr, too. Some of the designers at Tumblr do design all the time whether or not they’re at work. Because if you are really, really passionate about a field and about a specific practice, you can’t stop.
Right now, I’m super excited because I’m moving to a new role at Tumblr as a product manager, which will give me the opportunity to zoom out a little bit and worry not just about how we build our iOS app, but more about how we build the whole thing. It’s exciting because I want to be where I’m the most useful, and I’m all about trying to be wherever I can be within an organization where I can be of the most use. It’s not about being a rock star, it’s about contributing the most.
You’re talking about roles and parts and stars—did your theater experience inform the way you think about these things?
Absolutely. I did theater all through middle school and high school, so it’s definitely been a huge part of my life. In theater, I really, really wanted to be ‘the show.’ I really wanted the show to be great, and I wanted to control every aspect of it. But I learned in a somewhat painful way that that’s not the job of an actor, nor is it the job of a sound designer. (Those were the two roles I played.) It’s humbling to learn that your role is really what’s your role. If you’re not the director, don’t direct. Even though you might have great ideas about how the show should look overall, there are other concerns that you are not aware of. So if there is another role that you should be in, you’d better make sure that your role is going to be covered. Because the whole team is necessary to create a complete piece.
Software and theater are so close together in my mind. The ’show must go on’ spirit of the rehearsal process very much influenced my testing process. The celebration of the opening night cast party really influenced how I take my team out to celebrate releases. It informs how I think about everything.
In addition to the theater, I know you also have a passion for cocktails. Does that also factor into how you think about what you create?
Yes. In very general terms, I enjoy thinking about systems. Any systems: large ones like theater production or theme park construction, or small ones like a cocktail. I’ve always been fascinated by the system of creating a piece of art. The process is a lot more interesting, or at least as interesting, as the end result. That’s why I like listening to director’s commentaries, being in the dressing room of a Broadway actor, or talking to a great bartender. Because you are seeing things when they aren’t fully prepared, but you’re seeing the elements that are crucial to the production of something.
Making cocktails is me wanting to do something with my hands that’s not in front of a screen. It’s very expressive. I can create an experience for somebody that will make them feel something, in such a short amount of time. Creating software feels like it takes forever. I want to make software that makes people feel things, but that will happen in six months from now. But with cocktail, it’s five minutes.
When we’re making drinks or software, we are creating an experience. It’s not just cranking out widgets. The more times you make something and the more you develop your taste, the better suited you are to make something better next time. I think my taste in food and cocktails have been developed by not just tasting them but also trying to make them myself, seeing what’s hard, seeing what’s easy.
Can you see what you’ll be doing in five years from today?
I’ll probably be building something small. I think so many people are caught up in a dream of building the next Facebook or the next Tumblr, dreaming about that winning lottery ticket. But that’s not something that gets done because someone just woke up and decided to do. My focus is on building things that are beautiful and small. There is this musical called Title of Show. And there is a song in it called Nine People’s Favorite Thing. It has this line that’s stuck with me—“I’d rather be nine people’s favorite thing than a hundred people’s ninth favorite thing.” That’s how I feel. I want to make things that people really, really love, and it’s okay if that’s a small number of people.
What does New York City mean to you?
For me, New York is one of the few cities in the world that makes sense. It’s a home base, the place to be. I have reconnected with so many people from my past just by being here; everyone ends up in New York at some point. That’s not a thing that happens everywhere.
New York is a truly cosmopolitan city in a way that I feel San Francisco has maybe stopped being. In San Francisco, it’s hard to escape hearing people talking about valuation of startups, no matter what. But here, you can escape the bubble. It allows companies like Tumblr, companies that are on the border of creativity and technology, to thrive. I think that might be much tougher in SF.
I think it could be a harsh city for young people in some ways. When I was managing the iOS team at Tumblr, I had a couple of kids who just joined from out of the city. Things would get tough for them—bikes get stolen, roommates disappear, all sorts of things. If you are not used to the craziness you see everyday here, on the streets and on the subway, it could be a shock.
I grew up in Jersey yearning for that craziness. For me, it was a natural progression. I think it’s also a great city for empathizing. It’s a great place to see people of all races and classes and occupations, to really feel like you belong to a population. This is really helpful when I work on a product. You need the reminder to think about the users who aren’t you or the industry insiders. You have to think about users who don’t have hundreds of thousands of followers. The users who don’t have the same life experience as you. Does the product make sense to them? Is this feature going to matter to them? Being inside the completely heterogeneous population of New York just boosts you in this sense.
Matthew, what would you offer or ask from the readers who might be interested in working with you?
Lickability is very available for contracting, especially with Brian running it full time now. Regarding any stage of an iOS app, talk to us! We are also looking for people who really understand the marketing side of things, people with insights on getting apps in front of the right people. We work with designers (especially icon designers) all the time as well. They make our products way more beautiful than we could ever do on our own.