I wasn’t one of those kids who grew up sailing. My experience navigating the high seas was limited to a rowboat on my aunt’s quiet lake and a whale watching ship on a trip to Cape Cod in the 5th grade. Truth be told, I’m not much for getting flipped around by waves and churned-up sand. I’d rather not wage pointless war against the ocean in my spare time.

That said, I saw a documentary late last year about sailing and I could appreciate the effort. I watched as a group of men and women learned the ins and outs of a sailboat. They fumbled around with the mast, learned a bit of sailing vocabulary, and found that the hardest struggle of all was in balancing and timing the sail. Sailboats are tragic objects: so glorious with a bit of wind, so skeletal in its absence. I think that software can be tragic too: so glorious when it’s done right, so skeletal when it’s not.

I get to do a lot of forward thinking at Arc90, which is fortunate for me because that’s my favorite kind. From time to time, we discover a need to step back from the immediate projects we’re working on and ask larger questions about where a client is headed. Often this requires us to touch base with our client to gather more information about the needs and wants of the companies we work with. And once the information is gathered, we set a meeting.

My most favorite meetings at Arc90 are these, the ones that result in raising a sail.

We sit around a table and draw on a whiteboard. Sometimes this takes hours. Ok, often this takes hours. Everyone in the room has a different expertise, a specific constituency to lobby for, and there is always a fair amount of balancing. Once in a while we get to a point in the process when we don’t know where else to go. Everyone’s eyes glaze over and we get punchy. It seems that we’re too tangled up to see the solution.

But then there comes a moment when we begin making ground. You can almost sense it coming, as if a slight breeze has started in the room. Though they’re tired, people’s voices get faster and a little louder and all of a sudden the sail catches wind and we’re coasting. The feeling is the same whether we’ve successfully found a name for an effort or solved a tricky issue about integration- our collective thinking has seen liftoff.

The ironic thing is that the liftoff moment doesn’t signal an ending, but rather a beginning. Much of the hard work is still ahead. We must organize new meetings to decide resources, define requirements of this new effort, and get sign-off from the clients themselves. But in its most basic sense, we have found a graceful moment of agreement and we are ready to move forward.

There are both storms and beautiful blue days of clear software building ahead, but in that moment – at the end of that meeting- we’ve managed liftoff. And damn, it always feels good.

When a company blossoms from six to 36 employees—and you are present for almost every step—there are certain memories that remain with you. I was the fifth hire and joined Arc90 in April 2005. Back then, the company was run out of a sweatshop-style apartment in Brooklyn. We were a start-up in a walk-up, located on a very different Third Avenue.

While most of the working world commuted to Manhattan, I was taking two trains to the one-bedroom apartment/office. I had a 45-minute reverse commute on the D and R subways, traveling from West 4th Street in the West Village to 95th Street in Bay Ridge. I never had to fight for a seat, caught up on my reading and often tried to analyze the peculiar breakfast choices of people getting on in Chinatown.

Location, Location

Bay Ridge, Brooklyn is an entirely different environment when compared to Midtown Manhattan. My co-workers and I encountered kids in silver chains instead of men in business suits. The closest—and at that time, the only Starbucks in Bay Ridge—was two blocks away. We didn’t have lunch options where sandwiches and salads cost approximately $10. Bay Ridge’s large immigrant population spoiled the staff with the neighborhood’s various ethnic restaurants.

Our Manhattan building once housed Playboy magazine and we currently share an elevator bank with the BBC. In Brooklyn, we didn’t have a doorman or high-tech security cameras. We didn’t even have an elevator! There weren’t too many bragging rights about the Bay Ridge office—we were across the street from a car repair shop and above a family-run restaurant.

The “corner office” was a bedroom with a white board (and plenty of closet space); the window had a fire escape and provided a view of the corner deli. The programmer/developer/designer churned in the apartment’s common area while the business analyst/technical writer holed up in the bedroom. We all used one bathroom and I will refrain from telling stories about sharing a bathroom with four guys.

Interviewing Techniques 101

When I first interviewed with Arc90, I was living on the Upper East Side and almost packed my passport for the trip to Bay Ridge. During the journey, I figured that I was prepared to leave a lasting impression.

• Business suit. Check.
• Resume and writing sample. Check.
• Not rolling into the interviewer/company founder/your future boss. Umm…check?

The Brooklyn office’s slanted floor made it just a bit difficult to remain professional while trying not to slide around in a rolling chair. I didn’t run over anybody or crash into anything but it was also impossible to keep a straight face. I still like to think that I was being tested on my ability to adapt to change and my methods for avoiding conflict.

Boss Man

Rich Ziade, the founder of Arc90, lived on the top floor of the building. Most of our meetings were held after his morning run, while he was still in shorts and sneakers. Rich often discussed work while stretching on the kitchen floor. On several occasions, his mother would come into the office and demand a hug or kiss—even if he was in the middle of a meeting.

Rich often greeted us with muffins and it is a tradition that he has kept alive at the midtown office. During the summer months, he shared blender concoctions from his kitchen.

There was an unwritten Arc90 rule that you had to instant message Rich before going up to his apartment—merely knocking on the door might result in finding Rich having cereal in his boxers.

Although Rich currently lives very close to the Manhattan office, I doubt many employees know that he once kept a collection of *NSYNC bobble head dolls. FYI: Justin Timberlake and company are enjoying retirement in the basement of his family home.

Expansion!

The original crew came together like a band: Rich and Bobby are brothers, Bobby and Matt actually played in a band, Alex responded to a Craig’s List ad, I met Bobby at a mutual friend’s bar and Bobby and Joel worked at another start-up. Our drummer moved on to other things but the rest of group won’t be splitting up anytime soon.

The company expanded its recruiting guidelines over time. Current employees hail from outside of tri-state area and are from far-away places such as Arizona, California and Texas. For unknown reasons, we often receive resumes from Sweden. The female to male ratio has also steadily increased, compared from 1-6 in November 2005 to 9-27 in November 2008.

While we are all interested in seeing how much bigger (and better) Arc90 gets in the future, I always find it humbling to remember the journey that brought us to where we are now.