You have no formal design training. Have you always thought of yourself as a designer?
I consider myself a designer but an interesting kind because I deal half with technology and half with traditional design. I kind of bridge between the technology of a product and how people will actually use the technology. Like what do people actually want out of a book when they sit down to read it on their iPad or when they use book management software on their computer? I’m figuring out how to see it from a normal person’s point of view rather than a technology point of view.
That’s a design approach, to be empathetic and look at the need of the person. You came to that way of thinking naturally?
I like coming up with ideas and looking at things and thinking, “How can you make that better?” Or like in sci-fi movies there are these really cool, kind of crazy user interfaces, and sometimes it’s like, “Wait, why don’t our computers actually work like that?” I guess a lot of my motivation comes from my own passion for technology and creating things. Another way of looking at it is that I’m motivated by my own frustration with using technology. Lots of what we have to deal with everyday pushes me into it a little bit.
How did you get into design?
When I was 15 or 16 I started working at this software company called The Omni Group that was a few blocks from where I grew up in Seattle. They built OmniWeb, also OmniGraffle and OmniOutliner, and were one of the first developers to build a Web browser and on Mac OS X. I sent them an email and asked for a job.
So you knew what design was at that age?
Sort of. I was interested in design even though at the time I don’t think I really knew it. It was a path that I naturally ended up taking. I was into drawing stuff in Photoshop, but not like user interface design or anything really practical. The closest I got was drawing icons and stuff for personal purposes. I was just interested in software and thought that Omni was pretty cool.
I was hired in as technical support but after a couple weeks I just started helping design the products. I helped them make a new version of OmniGraffle that looked a little bit better and drew some icons. I spent a few years of working there in my free time, night and weekends, after school. Then after that I did consulting drawing icons or designing a little piece of a user interface. A friend of mine was working on this program called Library, which was an app where you could type in the name of a book that you had on your bookshelf and it would download a bunch of information about it from Amazon and put it into a little database on your computer. He hired me to redesign the interface for the next version. It turned out to be a more interesting project than I anticipated. I got more and more into it, to the point where I wanted to be more than a consultant—I wanted to own it a little bit more. It became more my project than his project at that point. That’s right around the time that Wil Shipley left Omni and we needed a more senior engineer to build what I was designing. So Wil and I teamed up and started Delicious Monster and paid the guy who hired me to let us take his stuff and build it as our own app.
At that point, you’re still 17. Did you know anything about business or equity?
Not at all, but we were starting a really small, tiny company. There weren’t a lot of books to keep or people to manage. Our company was run out of a coffee shop. Basically we would just come in in the morning and buy a bunch of coffee and sit around the same table every day, and that was our rent for the entire time we ran the company.
At the beginning it was interesting because not only was I really young and not very experienced, but Wil was an engineer and I was a designer. We spent about 8 months developing it. Wil had this idea of using a webcam as a barcode scanner so you could scan the book barcodes instead of manually entering in titles. We released Delicious Monster and it was fairly successful. At that time I was still in high school but quickly losing interest, so at some point during my senior year I stopped going. I left and focused on Delicious Monster and ran that for a while.
What gave you the balls to drop out?
A combination of a couple things. Number one, I never liked school in the first place. What I was doing a lot of things outside of school that were much more interesting to me—school was always an afterthought. About halfway through high school it dawned on me that I didn’t want to go to college because working at a company or starting my own I’d learn just as much as I would at a university. So that removed the element of needing a high school degree in order to go to college. That combined with releasing a piece of software that was mildly successful just made it not really necessary to finish high school or go to college, so I just didn’t.
What happened after Delicious Monster?
At some point I started talking to Apple’s human interface design team, which at the time was responsible for Mac OS X and all its apps. I moved to Palo Alto and started working at Apple when I was 19. It was exciting. While I was interviewing, all the discussions with the team were about Mac OS X and Safari and Address Book and Finder. But on my first day they told me about the phone project, so I started working on that pretty much when I got there. I worked at Apple for 4 years almost exactly. After a while I got a little tired of working at a large company. There are obviously benefits and drawbacks, the drawbacks being you don’t have the freedom to come up with something and follow through with it without asking for permission.
So I left Apple and took six months off. During that time I got a call from someone working with Al Gore to make a book that was the sequel to his movie, An Inconvenient Truth. They were about halfway done doing a printed version and were really interested in doing a digital version and asked me to help figure out what that might look like. At the time I wasn’t really interested in starting a company or getting too wrapped up in a project, but I agreed to do it because it was interesting. I gave them some ideas, met up with them, brainstormed some stuff, and did a few demos of what it might look like. But the more I worked on it, the more interested I became and the more I realized that this was a larger problem than just this one book. So when we started building some of our designs, my friend Kimon [Tsinteris] who was working at Apple decided to leave and start Push Pop Press with me.
Can you talk more about the thinking behind starting Push Pop Press?
Before Kimon left Apple, our thinking was “let’s piecemeal build an app for Al Gore and then move on.” But as we looked at the problem, we realized that 1) lots of other people wanted to build books like this, and 2) it was impossible to build the book we wanted without building a larger platform first. So we decided to build a tool that allow lots of people to create books and to turn that into a company.
We ended up selling to Facebook before we were able to do more than one book, but the tool was really powerful in enabling it. There’s still no other books like it because no one else has taken the approach of building a tool the way we did. There are many digital books out there, but they get made by a publisher sitting down with an engineer and telling him to move this image from this page to that page. It’s just not a very creative process because the publisher has to move at the pace of an engineer. We built the tool to allow publishers to independently create a book without engineers, so they can work with their own team and their own software on their own time. Then they’re able to try different things and see what works and what doesn’t and move stuff around and not be hindered by the technology.
Twice you were what we call a designer founder. Do you have a sense of what makes for a good designer founder?
A good designer that also understands the bigger picture of a product—that there’s a lot more components to it than just the face of it. At the end of the day what the product does for people is ultimately what you need to be optimizing for while you’re designing it.
You’re talking about going beyond the visual design?
Yeah, designing more holistically. Design of the actual product ideas and how something functions and which features you include and which features you don’t. And how you market them and present them to people from the first time they see it until they’re actually using it.
Does your role as a designer ever conflict with the entrepreneurial part of you?
Definitely, all the time. As a designer you get to work in the creative realm and to come up with new ideas and to perfect stuff. As an entrepreneur you have to balance that with actually shipping a product, and it can’t just look good, it also has to function in a way that people need it to function. So as a designer founder you need to look at your product from not only a design point of view but also from a requirements and functionality point of view.
As a designer do you usually not want to take those into account?
If you’re thinking clearly, you do. But lots of designers, including myself, have a tendency to want to design certain things for other designers, if that makes any sense. User interface design is its own world with its own trends. Designers have stronger views on the way stuff should work than the average person who is using them do. So you need to balance your desire to create something really crazy and amazing with your users’ tolerance for new stuff.
Who should start their own company?
You have to be really passionate about the product idea that you’re starting and have a vision of why it needs to exist and why the approach you’re taking doesn’t exist currently. You have to love it on a really deep level because it’s a long-term commitment. I’ve found that it’s easy to have days where you forget what the goal is that you set out to achieve. If you’re not working on something that you really care about, it’s hard to stay motivated and really passionate about doing your startup and getting it out there.
Having started two companies, I’ve seen the ups and downs, and after the first one you know that there’s a light at the end of the tunnel when you’re working on a long project for a long time. At both companies, we hit a point in the middle of development where morale was very low. It was because we were working in the dark without any positive reinforcement from the outside world that lots of people would love what we were building. When you’re working in isolation, you can lose sight of how cool what you’re working on actually is. That leads people to second guess their work and to think that they are moving too slow or that one person isn’t pulling his or her weight enough or that we’re wasting time doing this and we should have done it this other way. In both startups, we powered through that segment of the development process and things worked out for the better.
It’s just important to know that that’s part of the process and that there’s a good chance that at some point you will hate each other and have arguments and second guess what you’re doing and think that you should have done something else, but it is so important to keep going and keep your eye on the prize of what you’re building. That’s why it’s important to be really passionate about what you’re building and to want it yourself. Otherwise it will be really tough to pick up and move on when you hit segments like that .
Do you think that pattern of low morale in the middle of development is due to you being a designer founder working with technical cofounders?
The way designers and engineers work is usually designers spend a few months coming up with ideas and wireframing and building out prototypes and coming up with a spec. At that point, a few months into the process, a developer starts building. So it’s sort of two sine waves of work. The designer starts, ramps up, and their amount of work peaks. Then once they finish the general spec, they have less work at the same time that an engineer’s work is picking up. So where those two sine waves cross over you have this dip where the designer doesn’t have a whole lot of work to do and the engineer has a lot of work to do. And in both companies, that was where the tension started. The engineer is just trying to catch up to the design and those two waves of workload are not aligned.
So I think it’s really important to understand that cycle so you know what to expect and that things will balance out in the end.
Any advice for designers who are thinking of taking the path of entrepreneurship?
Depending on what your background is as a designer, really try to understand where engineers are coming from—the differences in the way an engineer and a designer approach things. It’s important to respect their point of view and vice versa, also to balance the two. Every project I’ve worked on with an engineer, there has been some sort of unspoken tension between designer and engineer. Through working with engineers I’ve really grown a huge amount of respect for them and can see how their work is very similar to the design process. It’s really important to nurture that relationship between engineer and designer.