The DC Nightowl: How A Federal Contractor Turned Entrepreneur

Rarely have I used the word “entrepreneur” in my conversations.  To me, it is a word that represents a certain type of person who has earned it with more than one successful business venture. It lacks a certain sincerity for us first timers.  It is even recommended in a lot of circles to “fake it until you make it.” To describe individuals who want to create a project, product, or service from scratch, regardless of their entrepreneurial track record, we go by “self-starters”.  We do it for market opportunity and reward, but also because its who we are. Over the past 3 years, I’ve explored what this means in community discussions at the DC Nightowls meetup group, and the newly created DC Earlybirds meetup.

In late 2011, I was a federal contractor with CGI, largely focused on the DOJ’s many accounting systems.  It was a 10 year integration project in which I had joined around year 2.  It was in execution stage, with little creativity to express and apply.  I enjoyed working there for a while, but I learned I wanted to start things.  As a software engineer, it wasn’t easy to duck out for creative coffee conversations with people working on other ventures, and even harder to connect with an “entrepreneur”. I was paid to be at my keyboard and work culture demanded a watchful eye over my gov email inbox that was not available on my smartphone. I also felt like an outside consumer, not a student, at various entrepreneurial conferences and events.
I ran the very first DC Nightowls coworking session with 6 attendees as an opportunity to explore creative side projects, during time I had available in the late evenings.  What I had discovered, was an emerging creative culture in the DC area, where go-getters and do-ers were eager to connect with each other, learn from each other, and produce in a practical setting.  I started to feel like I was a part of the entrepreneurial community.

DC Nightowls grew up with the emerging coworking market.  We started in a conference room at Radio Free Asia, but we quickly began running events at startups of that time, like LivingSocial, Opower and iStrategyLabs. We then shifted more into coworking spaces like Dupont Circle Business Incubator, Canvas Coworking, and Affinity Lab. This lead us to the newer players like UberOffices, WeWork, Cove, and others.  3 years and 200 events later, we’re 1800+ self-starters. We’ve hosted a Congressman, participated in a White House Innovation Summit, and coworked in the Capitol Complex.  

During this timeframe, I gained the boldness to leave Federal contracting, and start my own business with a colleague whom I was meeting regularly at Nightowls.  The community itself, showed me the power of peers, creativity, and pursuing a path more compelling for my life than the one I was on.  I saved money, reduced leisurely social time, increased productive time, and prepared for a disruption to income.  After leaving, I fought the emotions of leaving comfort behind and the wins and losses that equate to learning milestones within a new venture.

Today, Routeam, my business, has growing traction in the Health and Fitness industry as a software-as-a-service provider for club and client management.  We are bootstrapped to this day, because the more successful it becomes pre-funding, the more equity we get to keep.  We’re planning to raise in 2015.  Its been an exciting ride so far, getting a startup going, while balancing occasional temp consulting projects for new skills and supplemental income.

If you are looking to gain practical experience and insight on starting a product, service, or hobby project for your employer or yourself, try this group out.  You will encounter developers, designers, lawyers, accountants, marketers, teachers, rookies, and veterans. It takes creativity and drive to start something. Hone your self-starter skills with us:

By Andrew Conklin


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