Last week, I was asked to do a question and answer session with Erin from Sprouter. She wrote an article based on the interview, but I thought it would be interesting to also publish the questions and answers in full. On Friday at 11a PST, I'll be answering questions live on the Sprouter site on my profile. Hope to see you there.
- Q: Did you always know you wanted to be an entrepreneur?
A: I'm not sure I really thought about an entrepreneur as a distinctive type of person. My parents encouraged my siblings and I to do business-type endeavors from a young age, but always with a focus on the craft as opposed to the economics. So, we ran lemonade stands when we were little, baked bread for a nearby campground in middle school, and grew flowers and melons one summer in high school. In all of these things, the goal was to produce something of quality that people would want to purchase. Then in eleventh grade (1996, I think), some friends and I started a web business in the attic of my parents' century-old farmhouse. With no small amount of struggle, that business eventually morphed into a company called silverorange. But, back to the original question, I'm not sure I'd even call myself an entrepreneur first and foremost ? I'm a designer who helped start a few companies.
- Q: What led you to start Silverorange, and how involved are you with the company today?
A: Back in 1996, some friends and I started a little company called Whitelands Studio. We had figured out that the Canadian government was offering grants for teams to digitize museums' collections. So, for several summers we secured grants and worked with a local museum to create websites showcasing their exhibits. This was great work (and it paid better than flipping burgers!) and we learned a great deal about building websites and running a team, which was the reason the grants existed in the first place. After a few years, another local company contracted us to work on a fairly ambitious e-commerce system. Ultimately, that system turned out to be to be ahead of its time, but our teams worked well together and we merged teams to form silverorange in 1999. Since 2007, I've played a more back-seat role in the team. The other founders and I meet occasionally to discuss broad strategy.
- Q: PEI and Silicon Valley are two very different places to start a business. What are the pros and cons of starting a business in each community?
A: Great question, but a big one. Prince Edward Island has a population of ~120,000 people and is a two hour flight from large cities like Montreal and Toronto. There are only a few web companies that operate from Charlottetown, so you can be both physically and intellectually isolated in many ways. But! It's a beautiful place and the lifestyle there is very relaxed and extremely affordable. Recruiting talent is surprisingly easy with good computer science programs. It's absolutely possible to start a world-class company there, as silverorange has proven, but there are some challenges.
San Francisco, on the other hand, has obvious benefits such as strong networks, ready cash, and a culture where risks are encouraged. However! It's very expensive, it's much easier to get distracted from your core work (building products!), it's easy to get sucked into a fishbowl mentality, recruiting is much more competitive, and peer pressure can push you to take stupid risks.
- Q: You were the 4th employee at Digg - would you recommend any first-time entrepreneur spend time as an early startup employee to get experience?
A: Maybe. Digg was my first experience in a small startup and also my first time leading a design team. I benefited greatly from having deep experience in many types of projects before joining Digg. So, if a first-time entrepreneur already has experience building and shipping products, I'd say wholeheartedly that they should join a small startup. However, someone who has little real-world experience would do well to work with more senior people, perhaps. Just don't go to a huge corp where you risk being ignored ? find someone you greatly respect and convince them to take you on as an apprentice.
- Q: What did your time as Creative Director at Digg teach you about running a successful company?
A: I learned a great deal at Digg as the company grew from just four of us to almost 100 when I left. I learned the value of hiring great teams and how difficult they are to create. I now put much greater emphasis on recruiting, even when I feel too busy to put the time into it. I also learned a lot about decision-making with larger teams. When you're less than 10-14 people, making decisions by fiat is very efficient, but as teams grow it becomes immensely more difficult to still make decisions efficiently without alienating people whose opinions should be heard.
- Q: What were the main lessons you learned from building Pownce, selling it, and subsequently seeing it shut down? Do you look at Pownce as a success?
A: We built Pownce with just three people and two of us had demanding full-time jobs. So! The primary thing I learned is... don't start a company when two thirds of you have full-time gigs. It was a demanding couple of years and when I look back, it's incredible how much we actually got built with our small over-worked team. We also learned a lot about community engagement at Pownce. We had a wonderful, passionate, and occasionally rancorous group of users and we had a great relationship with them. From early on, we put emphasis on staying engaged with the community and we brought in a great part-time community manager to help us stay on top of things. This attention made a great deal of difference for the company. Do I think Pownce was a success? Well, I think the product had a great deal of unrealized potential. But! It was a good ride and we all learned a lot from it, which we've exercised in projects since.
- Q: What prompted you to start Milk?
A: Starting Milk was a pretty easy decision. Kevin and I had been discussing creating this kind of company for several years and suddenly things aligned where it was possible to go ahead and do it. We've both wanted to work with a small group to execute on several ideas that we've had percolating. Milk gives the ability to focus on several challenges at once with the kind of nimble team that can build kick-ass products.
- Q: How do you recommend non-technical founders find great technical talent?
A: Make friends. I frequently hear from people who have the 'greatest' idea ever and they want to know how to get it built. Ideas really are cheap, building is hard. So, build it yourself or become friends with people who can build it with you. Hiring people to build your product is exactly the wrong approach ? it's expensive and you'll end up with an inferior product. Don't know how to build an app or don't have any friends who can build it with you? Then you're doing it wrong. Quit running around trying to raise VC cash so you can hire that dream team. Go hang out with product builders until you're friends with them and you've learned some technical skills as well. And more thing. Don't 'network' to find technical people ? go out and make real honest-to-goodness friends.
- Q: What's your #1 piece of advice for new entrepreneurs?
A: Build things. Coming up with the 'greatest' idea isn't as magical as you think it is. Writing up a business plan isn't very helpful. Go out and make a product. Maybe that product won't be your big thing, but you'll learn a ton and each successive product will get continuously better.
- Q: What's next for you and Milk?
A: We're going to take our own advice and build! We have one large idea well into production, another smaller idea three quarters complete, and a few more large ideas in the hopper. Milk doesn't have a five year plan or even a two year plan. We're going to make several projects. When one of them is a success, we'll cross that bridge when we get there. Seriously, we're unabashedly figuring it out as we go along, which I think it's the only rational approach.
