Curiosity Makes The Entrepreneur
Interview with Kelly Smith, an entrepreneur, designer, and investor.
Kelly Smith is a well known Seattle entrepreneur and designer, he is also an early angel investor in Scoutzie, our advisor and a good friend. He is a relaxed and life-loving guy. If you met Kelly, you would immediately want to be friends with him. Currently the CEO/product designer of Zapd, Kelly was also a designer/founder of three venture backed start-ups. Paying his way through college by fixing cars and then working on the early internet products, Kelly eventually got in a habit of starting and selling awesome companies. Today we sat down with Kelly to ask him some questions about entrepreneurship, design and life. Read on, it is all true and there are some real gems here.
Your twitter handle is @curiousoffice and so is your email address. What is it? A design agency?
Back in 2004 my good friend Adrian Hanauer and I started this little opportunistic affair called Curious Office. We saw a lot of great entrepreneurs in the Seattle area and we thought that in a handful of cases we could perhaps offer a small amount of seed financing to help get them started. These days, there are a lot bigger ventures and a lot more access to seed investment but we were lucky enough to have found a few great companies to be a small part of.
Over the years, it also became pretty apparent that we could help out in other ways too. Most often that tended to be as sounding boards on the product and the product design. Whatever I can do to help ship is what I like to do. When I meet with people it is usually about the state of the product and how we can make for a better, more usable design. And, we also use our own office (which I've shard with other developers and designers who run freelance businesses) to explore our own ideas. Some of these have "graduated" into real companies which we go on to raise venture financing for.
Much of the work that we do has some foothold in design. For example, we started Imagekind which was the first marketplace for buying and selling art prints. We also started a little company called Inkd which was a similar marketplace for buying and selling graphic design templates. We also designed most of the new templates for Microsoft Office which was a multi-year affair. As I mentioned, we value curiosity as a key tenant.
For his part, our partner Adrian was curious as to whether or not Seattle could support a major league soccer team. Very courageously, he set out to try to prove it could happen and it's no secret that today it is a huge success. As such, he spends all his time working as the General Manager of Sounders, but we still occasionally find time to kick around more start-up ideas together. I think that will never change.
You’re a designer who turned a startup founder and CEO. Tell us how you started in this business?
Actually, I'm a start-up founder turned designer. And to tell you the truth, I never really set out to be a designer. And for the most part I still don't really think of myself as a designer. As a result, I often find it hard to describe what it is that I actually do. So, I like to joke that I'm probably totally unemployable because nobody can figure out what bucket to put me in. But I strongly believe that if you're going to be the most effective entrepreneur then you are differentiated from everyone else for precisely these reasons. It's important to know how to be more than one thing. Your knowledge has to be deep AND wide if you want to be a good entrepreneur candidate. But more on that later.
To get back to your question, I was one of those guys that graduated from college and I wasn't entirely sure what I wanted to do with my life. I moved to Seattle for no particular reason other than having a lot of friends here. It was only happenstance that I came into this line of work. A friend of mine knew I was looking for work. He introduced me to someone that was a technical recruiter. I had no idea what that meant but I had a technical propensity I blame on a few years of engineering studies in college and a higher than average curiosity for things in general. I soon found out that technical recruiters help companies find engineers. After about 6 months of that, I began to develop a suspicion that I might like to work in the industry I served.
My clients were interesting and the work they were doing was very intriguing. I managed to get an interview with a company that had licensed the original Mosaic browser source code from the University of Illinois. We packaged that on CDROM along with an email client and some other software and sold it in a box at retail. In fact, it was called Internet in a Box. That was early 1994. That's how you got on the web back then. You couldn't even download the software you needed.
What prompted you to start your first company?
I had spent 5 years working for a company based here in Seattle called RealNetworks. Actually it was called Progressive Networks the year I started. If you've heard of the company you might associate them as original developers of the technology that lets us stream audio and video over the web. During that time, I had the pleasure of working with a lot of really smart people and the company was clearly in it's heyday. I'd been exposed to all the industry disciplines, from sales to marketing to development and design. Towards the end of my time there, I simply recall thinking that I wanted to be closer to the actual things we sold to our customers. The software. I knew I could sell or market whatever we developed. But there were always things that bugged me about how we presented the software or how the interface worked or why things worked the way they did. I never felt that we shipped highly polished experiences. I felt powerless to do anything about it and that bothered me.
I felt powerless for a few reasons. One, I didn't have the skills to add enough value to change things. Two, the company had grown to the point where it does what many mid-sized companies start to do. The infrastructure starts to categorize people into buckets and I knew I'd never be given an opportunity to work on product in a meaningful way. So, I decided to leave and explore an idea of my own.
I knew very well that it would take me time to develop the skills but my first venture required a lot of business development effort to get off the ground. My goal was to aggregate special interest video (cooking, travel, pets etc) from all the production companies who had invested millions of dollars and decades of their time to distribute content the old-fashioned way. My plan was to acquire rights to that content and specialize in internet distribution of that video. A fairly new concept at the time but it wasn't something that any of these companies were doing at the time. Remember, there was no concept of a YouTube in 1999. Anyway, we sold that company to a Seattle software company who is today owned by Comcast.
I learned a lot and I felt prepared to take another step towards my new "career." I had spent enough time on the product that I not only developed more confidence but I also finally discovered my true passion and what it was that I wanted to do with my life career-wise.
There has been a lot of talk about “design thinking” lately. Did you find that helps you along the way?
I have always naturally gravitated towards this way of thinking. I tend to function reasonably well in situations where there is an above average amount of ambiguity. When looking for solutions in these types of environments you often first start with the "building up" of many ideas at once. I put a lot of emphasis on ideation and the importance of out of the box thinking and in fact we called our company Curious Office because we believe that the word "curious" really sums up what makes great designers and entrepreneurs. They are more curious than other people. They tend to seek analogies and have an unusual ability to visualize and find that A-Ha Moment. Finding that clear path forward at that mysterious intersection between analysis and convergent thinking and then prototyping around that moment is what defines creative, design minded thinkers over purely analytical thinkers. Purely analytical thinking discourages experimental thought processes which breeds fear and asks for proof points prematurely in a creative pursuit. Curious people who aren't afraid to throw things against the wall without fear of judgement and then iterate around those ideas tend to be the ones who are able to synthesize where others cannot or will not.
What do you wish you knew 20 years ago?
I wished that I had an even better grasp on the concept and importance of being curious and courageous. The most successful people I know (both in a personal and professional sense) have those two qualities in spades. Fear can be an important guide in some situations but most of the time it holds people back from being the best they can be. I'm not sure you can be too curious or too courageous. 20 years ago I would have liked to have worked on those attributes even more and I'd have exercised them in a more practiced way. When people are holding themselves back, they usually don't know it. Being present to courage or the lack of courage is crucial. And exercising your curious nature as you would a muscle is also very important.
What’s your view on work-life balance? Do you go all out?
I used to go all out. I'm a bit older now and I don't see every airplane flight as an opportunity to do emails for hours. Focusing on mental and physical health has become much more important for me lately. Getting outside, being in nature, being in the woods or on the beach or whatever...there were some years where I had forgotten how therapeutic that is. I'm sure my mental health suffered as a result. Today I'm much more sensitive to these things and I try to listen to my body and take care of it when it's trying to tell me something. On the other hand, I'm sure I still work harder than a lot of people but I don't think about it as work. I enjoy what I do and I don't dread these activities that pay the bills.
How do you have fun? Any hobbies?
I paid a lot of my way through college buying and selling cars. I'd go to auctions and buy cars that needed a little work and I'd fix them up after class. For whatever reason, our family has always been a group of petrol heads and I've had a lot of fun with my two brothers riding motorcycles and tinkering with cars while growing up. For the last 10 years I've mostly become fixated on older, air-cooled Porsches and I spend a lot of time trying to maintain these older cars. And, as a visual person I find these cars really beautiful. The design has lasted for decades. I also paint a fair amount and I find that to be a good juxtaposition to the many hours I spend staring at pixels all day. Finally, I'm susceptible to anything else adrenaline related which includes skiing, biking etc. And I wished I were a better surfer so I could join my friends when they go on surf trips.
How are the dynamics different between working at a company and being in charge of one?
When you work at a company, you'll probably note that they will primarily encourage you to be very good at the job description for which you were hired. I don't diminish the importance of this. But I sometimes feel there isn't enough emphasis on thoroughly understanding the other disciplines so you can be a more effective contributor.
When you run a company, it becomes immediately evident that you can't do everything yourself. If, as a founder you're the primary product designer then you'll need to spend most of your day doing that. But it is important to delegate effectively based on your accumulated knowledge of sales, marketing, business development, software development and so forth. You no longer have the luxury of thinking those things will sort themselves by others without your guidance. Your way of thinking needs to be the full 360 degrees so that you understand what everyone is doing and why. You may not do the work yourself but you need to become an expert or close to it so you can manage the entire business and not just the product design.
To be really good at understanding everything, you need to cast aside notions that commonly plague employees in companies. Thoughts like "I don't know how to do that" or "that isn't my area of expertise" or "I'm not a technical person" all need to be expired in favor of courage and curiosity. Lastly, you need to realize that you're always recruiting when you run your own company. At the end of the day, everything about everything is about the people. Finding talented people to work alongside you is probably the biggest job you have as a CEO.
What is one typical mistake that all new designers make, in your opinion?
This is an easy one. We've hired a lot of designers over the years. And the common shortfall is that graphic designers most often want to make things "look pretty" without really understanding the platforms for which they are designing. For example, I see so many iPhone or Android app designs that look great but you can see little clues all over the place that the designer never took the time to read the Human Interface Guidelines documents provided by Apple or Google. It's fine to deviate from recommended patterns but most designers don't even know they are doing it. Deviations are encouraged as long as they are thoughtful, sensible and most importantly, practical! If you live in a world where budgets, technical complexity and time to ship aren't important then feel free to design things however you want. But great designers balance their work against all of these things and they have a solid knowledge of the platforms and what would really be required to implement their designs. My advice is to put the Photoshop down and go learn more about the platforms and the other details that makes product design really come to life. In large part, this is why I was so fixated on Scoutzie in the first place. Good "mobile" designers are very different than good print designers. And it was hard to figure out which designers had any experience working on mobile.
What are some easy tricks for improving product design (for designers and non-designers)?
The best interactive designers develop a broader way of thinking. By that I mean, they either conscientiously or subconsciously consider a range of factors while doing their work. For example, there is no point in doing a page design that wouldn't lend itself well to the Bootstrap framework if you know that's what your company or client uses. Of course you can make anything work but it's important to be aware of the exceptions you create. Same for things like SEO. Does your design factor it in? What about calls to action? Does your page design help your company or your client conduct more transactions?
What I see a lot on Dribbble are some very talented visual designers but a great number of fairly impractical proposals for the real world. You'll see mobile designs that suggest alternatives to standard iOS or Android controls or views that aren't improvements over controls already provided by the platforms. As I said earlier, it's important to be aware of the platforms for which you're designing and then make very thoughtful choices when proposing totally custom interfaces. And don't misuse controls in your designs which were meant for different purposes.
Finally, my advice for all interactive designers is to spend more time with developers and work on becoming more technical. Learning basic CSS, iOS, Android etc will shed a lot of light on how you think about design. Understand the chasm between the button you made in Photoshop and what is required to actually implement that button in xCode. It doesn't mean you have to be a coder necessarily. But increasing the empathy we have for actual implementation will result in better, more thoughtful designs. The goal is to not just be great stylists but also to help raise the performance bar within the teams you work with and to help realize better products and user experiences.
Who (or what) has been inspiring you the most all these years?
Mostly it's the Seattle area entreprenuers I've been surrounded by. Friends Adrian Hanauer, his brother Nick, Mika Salmi, Rich Barton, Jonathon Sposato, and Jeff Bezos. There are so many people. These are guys who work hard, take chances, make thoughtful choices, have incredible track records, and are always willing to share what they've learned. Obviously, there are a lot of very accomplished and successful people in the Bay Area. That goes without saying. But with the exception of Jeff Bezos whom I've never met, I can say that these people have all achieved a level of success most never will and their curiosity and drive has never diminished. It's inspiring and it pushes me to do better. Other than that, I look to designers, artists, musicians, and industrials in other fields who have left a mark on society. Frank Lloyd Wright, Renzo Piano, Andy Warhol, Ferdinand Porsche, and Johnny Cash might be examples.
What’s your definition of success?
Being happy with yourself.
What’s the one advice you would give to aspiring startup founders?
On some days I feel like being a start-up CEO is the trendy thing and it would seem lot of glamour and fervor is associated with the aspiration of starting your own company. On the whole, I think it's a fine thing because we should encourage people to follow their dreams. Where things seem to feel disconnected for me is when I see people going through the motions of starting a company and really over-rotating on the process of starting and operating a start-up company versus having the true passion for the thing that prompted them to do so in the first place. I sometimes wonder how people find the time to go to all these start-up events, cocktail mixers, coffee meet-ups etc.
For me, I'd encourage aspiring founders to deeply fall in love with the thing they are actually trying to do. And if that isn't going to happen then stop and find another project that you are in love with. I have made this mistake myself. Running your own company isn't glamorous. It doesn't mean you no longer have a boss. It doesn't mean you have more freedom. It doesn't mean you'll make more money. What are you trying to change? Why? What's your motivation? Is it a burning passion or did you really just trade one "corporate" job for a self-imposed "start-up" job?
When you are working on something you aren't passionate about and you raise money for it then you'll potentially find yourself in a situation that feels an awful lot like being in the job you left to come start a company in the first place. Again, these are mistakes I've made in the past. It's not about going through the motions. It's about really believing you're doing all this because you're pretty sure your product perspective is what the world deeply needs.
Kelly Smith, pushing a young entrepreneur forward.