Q. What is the most valuable skill an entrepreneur should have?
A. The ability to quickly learn how to do new things. When you’re starting a new business, you need to wear a terrifying array of hats – you’ll never make it if you’re merely “the code guy”. Accompanying that, a tenacity bordering on stubbornness is vital.
What project have you’ve enjoyed building most?
Building Postling, a social media tool for small businesses, was wonderful. Our core founding team had fantastic chemistry; we could pump out new work on a daily basis and make it look easy. Unfortunately, we didn’t have the sales or marketing DNA needed to reach a wider audience and that limited our achievable scope. Given the chance, I’d work with those folks again in a heartbeat.
Do you miss working at Etsy?
No. Etsy was a fascinating community to build for and grow alongside, but the working environment was not something I’ve ever felt wistful about.
What’s difficult about creating in a collaborative environment?
Creation is almost always a difficult task, but it becomes impossible if you’re not working with the right people. If someone on the team isn’t gelling, it’s better to excise them quickly than try to muddle through a bad situation. Even when the people are right, you need to set out expectations and goals quickly to ensure you’re all working toward the same end. You need to agree upon the business model, the market, the ownership of the company, and acceptable exit strategy if applicable.
What’s your process for building a new engineering idea?
This is a subject that one could write a pretty thick book about, and in fact many have, but I’ll do my best to summarize. Everything I’ve ever built has emerged only after first considering the user’s perspective. Once a flawless, incredible user flow has been drawn out, through sketches on either Photoshop or real paper, we’ll do our best to smash it to pieces by highlighting ways that end users will get confused or stuck. This is a pretty easy job if the project is an addition to an active website; there are always more tricky variables to consider on a site people are currently using.
Once all feedback has been incorporated and “final” screens have been created, we’ll make a list of all of the database and model changes that will have to be made to facilitate the new feature. If it’s particularly complex, we’ll put these up on a mutually accessible wiki page for reference. Methods will be written to facilitate the storage, retrieval and editing of the new data, during which time the frontend development will proceed. Perhaps most importantly, developers thoroughly test out their work once it’s finished and correct any issues they find.
Chris Maguire is a software engineer, web developer, and serial entrepreneur. In 2004 he co-founded Etsy, an online marketplace for handmade and vintage goods with over 40 million members and $1 Billion in total merchandise sales. Since leaving Etsy in 2004, he has co-founded several other successful ventures including Waffl, and Postling, a social media tool that was sold to LocalVox in 2012. A Philadelphia native, Mr. Maguire graduated from NYU in 2004 with an A.B. in Art, Animation, and Computer Science.