How I Got Here

In 1997, when I was 24, I started an Internet software consulting company. To be frank, I started it mostly out of frustration of the way that other companies (mostly prominent “interactive agencies”) I’d worked for treated people. While I knew that it’d be fun to create software in the early days of the Internet, my primary goal when starting the company was to create a fun atmosphere — a clubhouse if you will — that people would love coming to every day. And I assumed that if that were the case, we’d be able to find cool clients and do some good work and make a good living at it. What started as a 1-man company organically grew to a 6-person organization that operated out of the living room of my apartment, to a group of 15 amazing folks in a “proper” loft-style office in downtown Boston.

We had a successful business for four years. We didn’t break any records, but we were profitable, provided very competitive salaries, great benefits, and a really fun atmosphere. And we worked on projects that, for the most part, we all found interesting and challenging. In many ways, even from a “standard business perspective”, I’d say we were more successful than the company across the street from ours, whose business was similar in scope to ours, that raised over $100MM, had some massive clients, and still managed to go out of business because they couldn’t make a profit.

After four years, our biggest client, because their promised second round of funding didn’t materialize, went out of business. As a result, they weren’t able to pay us a huge amount of money they owed us — for work we’d already completed. Being the idealist that I am, I was shocked and clearly disappointed, but knew that within a year or so, we could recover from that hit. But, within a week of that happening, all of our other, smaller yet consistent and substantive clients, called and told us that “because of the economy” (it was just before 9/11/2001), they were “reevaluating”, and as a result, had no more projects for us.

It was at that point that I “knew” that our business was no longer viable.

With no money in the company bank account, less than $500 to my name, and payroll of $40,000 due in 2 days, it was clearly time to shutter the doors.  I summoned the team (of 10 guys at the time) to our conference room, and with tears, told them that I loved them, that we’d had a great run, but it was time to go home.  There was no other option.  I told them that the paycheck I owed them wouldn’t be forthcoming and that that their health insurance and other benefits were canceled, effective immediately.  I told them that I’d do whatever I could to help them find another job (which was tough at the time), that I hoped we could all stay tight as friends, but there was just no more viability for our company.

It took a while for anyone to say anything, but eventually Jim — who had a bit of a reputation as a wise-ass — said, “I’ll stay.” I wasn’t sure if he was being sincere or sarcastic, so I acknowledged his kindness, yet completely dismissed the comment.

A few seconds — that seemed like minutes — later, Mark, piped up with, “Me too. I’ll stay.” Then Thomas, with his deep voice, “Me too. You’ll come up with something, you always do.”

One at a time, around the smallish dark wood conference table (which I still, to this day, use as my desk), each of them said they’d stay. I had no idea where this amazingly generous gesture came from, nor what they really meant by it, but I had (and still have) no words to express my feeling at that moment.

I told them that I had no idea what they meant, but I was willing to “run with it” and see what happened. I suspected that the adrenaline of the moment might wear off by the next morning. But, sure enough, the next day, and every day for 2 months, they all came to work, on time, and did whatever I asked them to do. To be honest, I’m not really sure what they worked on. We had a light trickle of client work but not enough to keep any one of them busy.

They all stayed for 2 months, without pay (more or less), until we landed a new client — the largest one we’d ever gotten! Soon thereafter, were able to sell the company. In the sale of the company, I only negotiated 2 points — a) that the entire staff would be hired by the new company (they had wanted to cherry pick); and b) that everyone would get a raise. This was definitely pushing my luck, since so many people, even programmers, we being laid off left and right at the time. We merged with the other company, and while that experience came with its own set of challenges, it was so amazing to feel that together we’d made something that looked a lot like lemonade.

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