Getting it Done

This week ADP stated that 693,000 jobs had been lost in the month of December, and the U.S. Department of Labor stated this morning that unemployment has reached 7.2%, a 15-year high. Those are some gigantic numbers – terrifying actually. And the Fed says it’s only going to get worse this quarter, and potentially longer. Is it any surprise? Americans have been spending spending spending for years now, piling up debt, and living their lives on a credit score. Is it because of deregulation? Who knows. The fact of the matter now is that we’re now paying dearly for this recklessness in the form of job losses, bankruptcies, foreclosures, homelessness, and much more to come.

Everyone needs to smarten up, fast. Individuals, companies, no one is excluded fro this. If you weren’t aware of this a few months ago, in late Q3, you better damn well wake up! I was shocked the other day to learn that a friend of mine is actually quite clueless about all this. He’s a bit insulated from it where he lives and in his line of work, but no one is really insulated from this. My wife works at Harvard University, which recently saw its endowment cut substantially, losing 8% or $12B. For the first time in a long time, people are losing their jobs at Harvard, seeing their pay cut, seeing bonuses and scheduled raises off the schedule. Harvard, one of the most stable employers in Massachusetts, is having these kinds of problems. Again – no one is insulated.

This applies to startups too, of course. In fact, I’d say it hits us harder and faster than most other businesses. And that brings me to my point. CitySquares has been hit by all this. Sales are down as small businesses were reacting to the news in September and October, and as they refocused their energies and also smartened up. Sales are down, cash flow is down, some of our customers have gone under, some have been unable to pay their bills. Nevertheless, we’re seeing our way through this. We have an amazing tribe here at CitySquares – some extremely dedicated and passionate people. These qualities were demonstrated this week when I asked everyone to take a pay cut. The result? Some people took bigger pay cuts than they were asked to! And another thing – everyone stayed. Attitudes are great, everyone is as committed as ever. It’s just amazing to me.

I learned so much this week, as a CEO and as a Founder. I learned about employee psychology, I learned about my own abilities as a leader, as a CEO, as a founder. I learned even more about buy-in, about the difference between a decision and a choice.

So, CitySquares underwent pay cuts this week and I can honestly say that on this blog with pride, and with my head held high. Because I know that our team is prepared to do what it takes to weather this storm. Because they understand that paycuts for everyone means no one gets let go, everyone stays. And this tribe is aware of the same goal we’ve had for the past two years – the goal that’s now within 5-6 months from happening – the goal of cash flow positivity. The only way we can make that happen is if everybody here is on the same page, and that has not changed. Everyone here must work towards the same goal! Cash flow breakeven, in this market? In this economy? Outstanding! Show me a business that’s within 12 months of cash flow positivity, and I’ll show you a business that gets it. But show me a business that’s not making changes, not making the necessary cost reductions, not doing everything to ramp revenues and I’ll show you a business that’s in a lot of trouble.

Another thing, we wouldn’t even be here talking about this right, nor ever even arrived at this moment in time, if it weren’t for our investors, our angel investors from eCoast Angel Network and other outside investors like Jonathan Kraft, Mark Cuban, even my own father, among several others. We’re truly fortunate to have such fantastic individuals behind this company. Angel investors are special and its easy to forget how important they are to the economy, to the capital systems, and to the world of entrepreneurship. Angels make it happen.

So, there you have it folks. The truth as bare as it comes! And that’s what my blog entry from earlier this week was about – the difference between decisions and choices. Decisions I had to make, and choices that I had to give to the staff. There were difficult, very difficult, decisions that I had to make, along with our board of directors. These decisions lead to other decisions, and choices, for the tribe – and this week they all chose to help each other, to make the necessary personal investment, to protect each other.

Monday was one of the hardest days I’ve ever had at CitySquares. Today is one my proudest.

Doing What You’re Good At

Seth Godin posted a nice little piece today, as he frequently does, about passion and expertise in whatever you do. Very timely, as I’ve been facing this very question in the past few weeks.

CitySquares has a tribe member who’s been with us for about a year now. She’s a rock star in so many ways. She also really enjoys her job and is proud to work at CitySquares. This is partly what makes her a true member of the tribe.

For the last year she has filled some big shoes, and performed in a job that was not well defined for her. She kicked ass at it, like I never thought possible. And over the course of time she’s naturally filled a role within the company that not only has been a bit of a vacancy within the organization, but is something she’s simply really good at.

No one asked her to do these things, no one pointed her in that direction. Instead, she saw a need in the company, and then filled that need. She’s done so with poise, enthusiasm, with total ease. Today, she was formally moved into that role.

What she did over the course of time, perhaps unknowingly, is what she’s good at, and what she enjoysvoluntarilyon her own. She did so because she has a natural expertise with it, and because she has a passion for it. You just can’t buy that.  The result, and hopefully the result of good observation by management, is a permanent move into that role. This will result in even better performance in this role, it addresses a need within the company, in a happier, more efficient, effective successful company, it results in happier customers and better retention rates, and best of all – a member of the tribe who’s even happier and more successful.

Founders and Leaders

Entrepreneurs come in different flavors, different sizes, different languages, and different abilities. Some entrepreneurs are brilliant engineers, some are opportunists, some are really good at sales and marketing. One thing is for sure though – not all entrepreneurs are leaders.

There are countless books on leadership. I’ve read a few, from Jack Welch to Rudy Guiliani, to Seth Godin. In this entrepreneurial age we’re living in, leadership has taken on a new meaning. Leadership is a bit more scientific too, than say entrepreneurship. Yet leadership can also be as enigmatic as entrepreneurship.

I’ve been thinking about these things lately, thinking about the essence of leadership in an entrepreneurial setting.

Fred Wilson, on his blog, said the following the other day:

I’ve heard people say, “If you want to know about a company, all you need to do is look at the leader” and it certainly is true that companies exhibit the traits of their leaders. But it’s also true that companies exhibit the traits of their founders. In fact, I’d argue that founders leave a longer and more indelible imprint on the DNA of companies than the person who is currently running them.

There are a host of reasons for why that is. To start, the business that the company is in is more often than not determined by the founder. And companies can move into different businesses over time, but most stay fairly rooted in the initial business that they started in. It’s also true that the culture of a company is defined early on and it’s hard to change it. Some companies are technology driven, some are product driven, others are marketing driven, and others are sales driven. That most often comes from the founder and it’s hard for a new leader to change that mindset. Another important reason that the founders often have the greatest impact on the DNA of a company is the entire initial management team is most often built by the founder. That initial selection of people is a critical determinant in the way companies evolve and behave and new management will always struggle to change the behaviors a company exhibits.

Founders are entrepreneurs, whether they like it or not. That’s just inherent in founding a company. It’s like giving birth to a child, you are a mother. However, just because you’re a founder, or just because you’re an entrepreneur, doesn’t mean you’re a leader.

I recently read Tribal Leadership, by various others, and Tribes, by Seth Godin. I’m trying to better understand my own style of leadership, the qualities and the characteristics of it. I’m trying to be a better leader, and know where my weaknesses as a leader may lie in order to do so.

What I enjoy most about doing what I do every day here at CitySquares is not closing deals, analyzing Excel workbooks, or conducting board meetings. I don’t particularly enjoy any of those duties and tasks, or many of the countless other responsibilities that come with being the CEO. And none of those things actually make me a leader. What I do enjoy doing is working with the people within CitySquares, as well as the customers and the advisors. I enjoy affecting change, helping the company move forward as a single unit, as a tribe, who actually enjoy their jobs. I enjoy protecting them from the noise outside these walls, and from those who may try to stop them from succeeding. I enjoy achieving our goals, collectively. I enjoy inspiring. I enjoy seeing them smile at our holiday party, as if they’re actually happy to be there because they like the company, they like who they work for, they like who they work with. I enjoy working with my team to find new ways of accomplishing the greater mission of CitySquares. I enjoy inspiring and affecting change then watching them execute, and learn, and get even better at it.

Is this leadership? I don’t know. It’s me, I know that. It’s who I am and it’s what I do best, I think.

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!