Startups are Families

CitySquares isn’t the first startup company I’ve been a part of, but it’s certainly the most special, because it’s my creation. This company has taken on a life of its own. It took some time for it to develop this heartbeat and to get this personality. No doubt it’s is an entity all to itself, more so than just a tax ID with the government. From the very beginning in August 2005, a culture was starting to take shape. We’d sit at my kitchen table in Davis Square and talk about what this could be, how it would work, what kind of future should we plan for, what kind of company do we want this to be. Even when it was just three of us, and even when we had sales people making minimum wage out on the streets all day, every day, it was forming a personality. It was largely out of my control too. I could influence the culture a bit, just by being a part of the business, and setting the vision. But the personality, the culture that the company takes on is essentially a manifestation of the personalities and cultures brought into it by its staff, even those that come and go.

Startup companies are families. If you’re part of a startup, you know what I mean. If you’re not, ask someone, and join a startup. It’s special. There are some people who were with CitySquares for only a few months, going back to 2005, some I think of very fondly, others not so much. Those people, no matter how short or long a period of time they were with the CitySquares, influenced its personality, shaped its culture, impacted today’s family members. Once the company received financing it was inevitable that the culture was going to change, and perhaps a bit radically, and quickly. Sure enough, it did, but again, in positive ways. I’ve always kept company culture in our sights, ensuring that CitySquares was a place that people wanted to be, enjoyed coming in. There’s simply nothing worse than not looking forward to going to work because of its people, or because of its culture, or because you don’t fit in. That was unacceptable to me from the beginning. Good attitudes have been, and still are, essential to being here. As our job descriptions always indicate, guts and passion are requirements. If you don’t got the guts to jump into the deep end, in the shallow end you’ll stay, forever. If you don’t have a passion for what you do, or for CitySquares, stay home.

We’ve also always had a diverse group of people working for us. White, black, Hispanic, man, woman, gay, lesbian, it doesn’t matter. Can you do the job? Do you have something to offer this company? Will you add some new flavor to the dish, in a good way? Will you last? Do you have goals? Passions? Do you have a life outside of work? That’s what we have today, a diverse, fun, whip-smart, ambitious, and real people at CitySquares. They’re my family, and I’m theirs. We see each other more than we see our own families, spouses, children!

The hardest part, however, is having to see one of these brothers and sisters leave us, whether on their own accord, which hasn’t happened much, or because we ask them to leave, which happens more often than I can stomach (once is enough). There’s nothing harder, nothing more difficulty for me and for the others, than to see someone leave. To have to clean up their desk, forward their email, redirect their phone calls, pick up where they left off, sucks. It totally sucks. There’s something almost macabre about it. I have a certain affection for everyone here at CitySquares. I have an affection for most of those who’ve left the company, on good terms anyway. I’m still in touch with many of them. I think we all have that affection.

There are the good times, and there are the bad times, especially in a startup company. Change is inevitable. It’s not predictable either. Can everyone adapt? Can everyone accept the changes? Everyone has to have a certain amount of faith in a startup. If someone doesn’t buy-in, it can jeopardize momentum. If someone’s not performing as needed, the tolerance is low. We’re only as strong as our weakest link. No matter how much it hurts, change can come at will, or it can be forced. It’s our choice. I’d rather choose my own change than have it forced on me.

The best is yet to come, and I keep reminding myself how so many others here at CitySquares have never been a part of the next phase of a startup, the growth phase. I have fond memories of my days at Delphi and Prospero, when the company ballooned from 12 employees in a crappy office on Mass Ave in Cambridge, to a much larger, sunnier, more vibrant place in Kendall Square. I remember the growth, the excitement, the thrill in the air. Everyday was so exciting! CitySquares is close to that feeling. My family is about to experience such excitement, thrill, anticipation, and that makes it all worth the heartache and pain.