October 16, 2009 marked the fourth year for CitySquares.com, a reflective milestone for co-founders Ben Saren and Bob Leland who recognize the successes and growth of CitySquares.com since its launch in 2005. CitySquares.com began as a small website with information about local businesses in seven Boston area neighborhoods to what is now a national hyperlocal resource with over 14 million businesses, tens of thousands of users, and rapidly growing traffic. Today, the CitySquares team continues the vision these two founders have spent the last four years expanding on; to ensure that neighborhood businesses get the attention they deserve.

The CitySquares.com website was founded with business profiles from only a few communities in the Boston Area. As of March 2009, CitySquares expanded across the nation and today there are over 14 million businesses on our site with over 18,000 written reviews from website users, and growing fast.

Co-founder Ben Saren says, “We both originally had a vision of helping small businesses get online exposure in a hyper-local context and now it’s not just a vision, it’s a reality.”

A little over four years ago, October 13, 2005, the CitySquares.com launch party was held in Davis Square, Somerville, MA.

There were performers from the Deborah Mason School of Dance, face painting and other activities for members of the local Davis Square community. The neighborhood warmly welcomed CitySquares into their neighborhood and lives. This assistance and the many other contributions people have made since day one for CitySquares have not gone unnoticed by either founder. Some of the first businesses to be a part of the CitySquares family include The Square Nail Studio, Massage Therapy Works and Wedgewood-Crane & Connolly Insurance Agency.

Ben Saren, co-founder and CEO, says, “The exciting thing about being a part of CitySquares is the culture, mission and approach. Everyone who has been and is a part of CitySquares helped us get to this point. I want extend a huge thank you to all of them.”

Along with the development of CitySquares, the long-lasting friendship between co-founders Bob and Ben is a model relationship for all business duos.  Bob says, “While so much has changed over the past four years, and we’ve been through so many highs and lows, our vision is being realized. We’ve come so far as a business, as a company, and Ben and I have grown so much as entrepreneurs and friends.”

Both founders are humbled by this milestone and how much CitySquares has grown over the past four years.  They are looking forward to many more years of helping small businesses get exposure, and attract the interest of their local communities and consumers.

Special thanks to Justin, Kim, Michael, and Amber, who continue to fight the good battle on behalf of Local Search and on behalf of small businesses.

Happy 4^th Anniversary CitySquares.com!

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, and 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.

[youtube=http://www.youtube.com/watch?v=qnAETZxfMVM]

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 CitySquares.com’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!

– Ben