I made a mistake this weekend – I forgot about balance and paid the price. Actually, it’s not so much that I forgot about it, rather that I neglected to enforce it for myself and I know now that it’s been happening for a while. If there’s one thing that’s certain about these stressful times, with the economy and, for me, with CitySquares being at such an exciting precipice, it’s more important than ever that we all keep a healthy balance in our daily lives. Everyone is a bit more on edge these days than normal. People are inevitably going to be a little short-fused, or edgy. Myself included.

As an entrepreneur, my work tends to take over everything in my life – literally everything. When I hop out of bed in the morning, it’s game time. In fact, I don’t sleep much, because in between sleep phases I’m still gaming. When I sleep, I often dream of work. When I’m in the shower, I’m thinking about CitySquares. My iPhone is only an arm’s length away, always. Throughout the day I’m full-on. When I get home to see my wife, I’m full-on. When I eat dinner, when I watch TV or a movie, when I’m out and about, my mind is spinning about CitySquares. I may fake it well, but I’m constantly working. It takes a lot to bring me back down. Like, horse tranquilizer strength to bring me down.

Now, this is mostly expected from an entrepreneur and founder of a company – it’s actually normal in the world I live in every day. But as it pertains being a human and living out my life, it’s not normal – it’s harmful. It hurts. It hurts my relationships with others, my mental health, emotional and physical health. It’s literally caused me health problems – some I’m watching closely. In very rare circumstances it can affect others, even hurt them.

This weekend I had an eye-opening and very plainly realized that I’m on a path to self-destruction if I don’t correct this right now. I must get back to balance. I have some hobbies that I’ve neglected lately, some friends and family that I’ve neglected, some passions that I’ve ignored. Maybe I need a long weekend away on a beach somewhere. I’m not sure, but I’m going to figure it out fast.

As with everything in life, there must be moderation. And that goes for entrepreneurs too! In this fast-paced, web 2.0, always-connected, get-ahead entrepreneurial way of life it’s so easy to get lost in it all.

I believe it was Buddha who said, “everything in moderation, even moderation.”

‘Nuff said.

Happy Birthday CitySquares!

This weekend is CitySquares’ 3rd birthday! It was October 15th, 2005 and Bob and I had been working extremely long days getting the website ready for its unveiling, but it was entirely on Bob’s shoulders! For the previous eight weeks or so, while Bob and a contractor worked long days and nights to build that first version of the site, my time was spent mobilizing a grass roots sales effort with the help of some freelance sales people, as well as some marketing efforts with the help of Chris. We all worked tirelessly in anticipation of this day – October 15th, 2005. We planned a big party in Davis Square where we’d celebrate the launch of the website but also the underlying principles that CitySquares hoped to embody – principles of neighborly living, of community, of small business, and of friendship and we’d hoped that we could draw out the local residents of the greater Davis Square community in Somerville. Finally, when October 15th arrived, it was cold and extremely wet – it was pouring, downpours, and ferociously windy. There was no way we could hold our party. But we still launched the website (see it here on Wayback Machine).

When the site launched, it launched with only seven neighborhoods on it – Davis, Porter, Harvard, Central, Kendall, Union, and Inman Squares, a barely a thousand businesses listed. When the site launched that Saturday, there was also no traffic – no unique visitors, no page views. There was barely a business model, there were no salaries, no employees. There were a handful of customers who believed in us, and a few people who were eager to see us succeed, and others who were eager to see us fail. There was very little more than a tax ID number, a domain name, a clunky website, and a few pie-eyed believers behind the business that included not just me and Bob, but Chris, my wife Ali, my father, mother, sister, some freelancers like my friend Rahkeen and a couple others. And there were the local businesses, like Carla at Johnny D’s, Heather at Square Nail Studio, Lynn at Chinook, Richard at Massage Therapy Works, Deborah Mason and her dancers. There was Jason Burrell, a talented artist, Lo Galluccio a talented singer and songwriter, and Jack Connolly the Alderman of the Davis Square district, and good friend to CitySquares. There were others too.

The next day, October 16th we held our party in Davis Square. It was sunny, very nice out, but it was still extremely windy. The party was attended by so many people of the neighborhood. We had artists there, musicians, dancers, family, friends, and Cookie Monster (played by my mother). My sister Alison and wife Ali did some face painting, small businesses came out and participated. All when CitySquares was barely more than an idea, and a dream. It was a magical weekend for us, one that Bob and I reflected on this week.


The odds of a business idea materializing into an actual business, with a heartbeat and with people propelling it forward are extremely low. Once off the ground, the odds of the business making it through its first year in business, its second, and its third are also very low. I won’t spout of those statistics because it’s just not important. They’re numbers, and if I paid attention to all the numbers that were stacked up against me in life I probably wouldn’t get out of bed. Ignorance is bliss when your a startup entrepreneur!

What’s really drives this company’s successes and it’s growth are the people. We’re not just a company, just a business, just a startup. We are a tribe! CitySquares is a peaceful tribe, we mind our business, but we’re fierce and our spears are sharp. Our warpaint is ready and we are warriors at heart. It’s that heart, that passion, those guts that drives this company. It started on October 15th 2005, and it continues today, three years later.


This week marks the 3rd birthday of‘s launch, but it also marks a day when Bob and I made a decision that would change our lives forever, and lives of others to come. Today, we have some very special people involved with the company, both on staff, as well as customers, people who use the site, but also on its board of directors, its board of advisers, and among its investors. Our families all support us, our friends, our spouses. CitySquares is three years old, but 100 times more powerful. The future on October 15th, 2005 was so foggy – so massive and overwhelming. Today, the future is more clear than ever, and remains so full of potential and opportunity.

The tribe is as united as ever, the company as lean and mean as ever. We’re powerful, we’re proud, we’re competitive. And we have more heart and passion than any other company I’ve ever been involved with. More people will join our tribe in the days, weeks, months, years to come. Other milestones will be reached, birthdays celebrated. I can’t wait.

Happy birthday CitySquares!