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Posts Tagged ‘CitySquares’

Sixth Photo Meme

December 16th, 2008

My friend Sooz tagged me in a little Interweb game called Sixth Photo Meme. Basically, Sooz went to her Flickr account, to her 6th page of pictures, and to the 6th picture on that page and then tagged me in the picture. Now although I’m not actually in the picture isn’t the point - the point is that this viral game spreads like wildfire. It’s fun! The one caveat is that you need to have a Flickr account to participate, but even still you need to have at least 6 pages of photos.

So here’s my Sixth Photo Meme! This is a picture of the best game of baseball I’ve ever had the pleasure to attend - October 17, 2004. It was the 2004 American League Championship Series, game 4 at Fenway Park - Boston vs New York. This was the game 4. The one that resulted in the best comeback in sports history, the comeback that ended the Red Sox’s 86 year championship drought. I had the great fortune of attending this pivotal game, this pivotal moment in baseball history. I watched Dave Roberts steal second base - the single moment, the single play that changed it all. This is a picture of Mariano Rivera, perhaps the best closer in baseball history, on the mound in the midst of this game as it unravelled for the Bombers. Anyway, here’s my 6th photo from page 6:
IMG_0947

So it’s my turn to pick 6 people to play this game. Here we go:

Ryan Sarver, Sean Coon, Nate Aune, Tara Hunt, Dana Zemack, CitySquares

New Media and Web 2.0, Pop Culture, Social Networking , , , , , , , , , , , , , , , , , , ,

Two Simple Statements

November 22nd, 2008

610xAs I was leaving the ILM:08 conference Friday afternoon I made my way around the various rooms and hallways to say goodbye and shake the hands of the many people I met with over the last few days. As I neared the lobby of the hotel I bumped into the Localeze crew hanging out and waiting for a cab to the airport. I walked over to thank them for the dinner and drinks from the previous evening. We joked around about a few things, as we usually do, and when I thanked Brian Wool, Vice President at Localeze, he responded “No Ben, thank you, we really appreciate your business.” I didn’t think much of it, we chatted for a minute longer and then I left the hotel for the airport.

Coincidentally, when I arrived my airport terminal I bumped into Geoff Jeff Beard, President of Localeze. We chatted a bit while until it was time to board the plane. I turned, shook his hand, and said “thanks again for the great time last night, really” and his response was “It was our pleasure, and thank you, we really appreciate your business.”

That’s when it hit me - “Thank you” and “we really appreciate your business” - two very simple statements, but so powerful. And sadly enough, as consumers and customers we just don’t hear it enough. Instead, we see a generic sign from the hardware store hanging in a window, or on the back of a cash register, that reads “Thank you, come again!” or “We value your business” but so rarely is it actually spoken.

When I sat on the plane I started to realize something - I’ve heard these statements many times from Localeze. In fact, I’ve heard it from each and every one of them either oh the phone or in person. I found myself rather dumbstruck by this, as simple as it is. All of this translates into something else, something vital in business - loyalty.

Like all companies there are a number of service providers, partners, and vendors that we work with at CitySquares. Nearly all of these relationships have lasted because, well obviously they provide value, but also because they appreciate our business and they make sure I know that. They make us feel like we’re valued. If I don’t feel like they appreciate my business, I’ll continue doing business with them but if someone else comes along and makes me a better offer, I’d give it serious consideration.

CitySquares’ relationships with our customers are our biggest asset. We have a high customer renewal rate because we take care of them, we provide them with value, and we appreciate their business. In fact, every month we have what we call Customer Love Day. Yeah I know, it sounds a little corny but that’s what it is; Customer Appreciation Day sounds so corporate and cliche. The point is that we make a concerted effort to make the time and we go out of our way to check in with our customers, provide them with additional value and to thank them and let them know that we appreciate their business. This is a process that’s simply in CitySquares’ DNA.

In these tough economic times, as businesses struggle in various ways it’s never ever too late to tell your partners and customers that you appreciate their business, to thank them. You can’t build loyalty in one phone call though, it takes time - but you can start today.

Clear a few minutes off your calendar and call just one of your customers today, or one more. Thank them, do something for them, go the extra mile. It only takes a moment and the worst you get out of it is a happy customer.

CitySquares, Entrepreneurship, Networking , , ,

Happy Birthday CitySquares!

October 18th, 2008

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.

[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.

IMG_1173

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!

CitySquares , ,

Startups are Families

August 28th, 2008

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. Read more…

CitySquares, Entrepreneurship, startups , ,

Poking Fun at Print Media

June 21st, 2008

At CitySquares we had an idea to put a Flash video together that properly conveys our feelings on traditional print media like phone directories and the newspaper. We couldn’t think of a better way to demonstrate our feelings than by killing a fly with a rolled up newspaper (which begs the question, where did the paper come from?) and by phone books stacked up outside apartment buidings. Of course this video also had to be a shameless self promotion for CitySquares! Well, yeah! That’s the point… :)
So without further ado, here is the final product:

[wpvideo 3QjgpTmO]

You can find the original Flash version of the movie here on CitySquares.com. We also threw it up on YouTube and the CitySquares Facebook page.

What do you think?

CitySquares, Local Search, New Media and Web 2.0 , , , , ,

CitySquares at NY Venture Summit

June 5th, 2008

CitySquares was lucky enough to be invited to the NY Venture Summit June 24th and 25th. This is our first NY Venture Summit and we’re really excited to be a part of it. We’ll be one of about 40 exhibitors there. It’ll be myself, Bob Leland (Co-Founder and VP Product), and our Sales Manager Kim Hillis. If you’ll be there please be sure to stop by our table and say hello!

As a side note, please pardon the lack of blogging lately. I’ve moved much of the CitySquares specific blogging to the CitySquares Blog, and frankly, on a personal and professional front, I just haven’t had much to blog about. I’ve been getting fired up about a few things lately, so it won’t be long until I get something up. Also, I hope you like the look and feel and organization of the new blog, on Wordpress.

CitySquares, Networking ,

Choose Your Weapons Wisely

May 24th, 2008

Thursday evening Bob and I attended a networking event in Waltham hosted by TCN, at Foley Hoag’s Emerging Enterprise Center. As usual, it was well worth our time. We met some great folks who are doing some cool new things in a variety of innovative industries. We also got a chance to catch up with some folks we haven’t seen in a while. After all this I started to reflect on how instrumental some of our service provider choices have been for CitySquares. Choosing the right vendors is critical for a startup and I firmly believe that it can make the difference between being a startup and a relevant startup.

Find the right law firm. When we started out in 2005 I actually made it a point, and a time consuming process, to go out and interview law firms. Being that we’d be interfacing with consumers as well as small businesses, hopefully in high volume, I knew we’d need good representation and especially if we were going to raise funding. First, I wanted a firm that could provide a full suite of services to us. Having worked with boutique, or home based lawyers, I knew what they could provide and I knew very well what they couldn’t provide. At my previous company a home based attorney was OK, but not for CitySquares. Secondly, I wanted a firm that had extensive experience with high tech startups and Internet startups. That was very important to me. Lastly, I needed a firm that could provide a deferment. So I set out on a two month project to find the right firm for CitySquares. I literally conducted interviews. I had lawyers from small firms and large firms coming to our old office to meet with me and sell me. Most of them were pretty darn good. They were about as good a salesperson as I am, and that concerned me a lot of times. Other times I’d go to firms and they’d show off their view of Boston, or impress me with meetings with senior partners in the firm. At times I was flattered, because, who were we? We were nobody yet, and we didn’t have two nickels to offer. But I think they were all selling me just as much as I was selling them.

One evening I went to an entrepreneurial event at Foley Hoag called “Negotiating Term Sheets.” The attorney from Foley Hoag who lead the event seemed like a nice enough guy, and he put up with me during the event. I was a little outspoken at times about some of the terms and even about raising money at all. He tolerated this. After the event I asked for his card, told him that we were looking for a firm to help us with various corporate matters, funding, and then building the business etc. Long story short, Foley Hoag is now our law firm.

Now, I have to say that despite the fact that, yes, we’re talking about lawyers here, there is no substitute for a good lawyer. What I like about our firm and about our guy, is that a) he’s not your typical lawyer, he’s a pretty regular guy - salt of the earth, b) they treat us extremely fairly in any number of ways, and c) they have this EEC thing I mentioned in the first paragraph - the Emerging Enterprise Center. I can’t say I’ve attended all that much there, but when I have it’s been well worth it. It’s all about value-add right? I hate that expression, but it’s so true.

Find the right bank. Also along these same lines is picking the right bank. When we were on the hunt for financing we knew we’d need a good bank. And some might say that Citi or Bank of America can do just as good a job as any, or that the community bank around the corner can. And ya know, that may be true but it’ll be a long time until I find out because we chose Silicon Valley Bank based on numerous recommendations by numerous trusted folks, from our advisers, our CFO, to our attorneys and prospective investors. If it’s good enough for them, it’s good enough for me. I don’t quite know what I’m really looking for in a bank anyway, aside from lower fees, good rates, and a strong relationship. What you get with SVB is the later, strong relationships that hinge on the very fact that you are a funded startup company and that they understand your needs unlike any other bank. They also have relationships with your investors, as well as countless others, and that makes for some very good treatment. They know that if they treat you well, that they’re also treating your investors well, and in doing so, building relationships. Silicon Valley Bank was able to get us started on some basic banking services very fast, but also with some nice value-added services, like an unsecured credit card with a very reasonable rate and limit. Despite their name and that they’re headquartered in California’s Silicon Valley they are here in Boston. They have an office in Newton, not a branch, but they are able to handle deposits there, which they also offer via a free courier service. At SVB’s Newton office is where you can find one or two of Boston’s more well known angel investor groups meeting once a month. Those relationships can start with SVB. I bumped into our rep from SVB at the Foley event Thursday, and he was full of good information about a great many things going on in the Boston startup arena. Again, this is a key relationship that you just can’t find with your standard, every day bank.

Find the right accountant and CFO. There simply is no substitute for the right people handling your books and financial strategies. I’ve been using the same bookkeeper for about 8 years now, and I trust him with my personal finances as well as my business’ finances. He’s handled my taxes, my wife’s taxes, and my businesses’ taxes. This long lasting relationship will continue for a long long time. Why would I ever consider changing? He has never let me down, he’s been with me through the tough times and the good times, and he works very well with our financial strategist, our CFO. If the three of us couldn’t work well together, I’d be in a lot of trouble. I met our CFO a little less than a year ago, he was referred by one of our advisers. He’s got a ton of experience in the Boston startup community, specifically with technology and Internet ventures. Let me repeat that… He’s got a ton of experience in the Boston startup community, specifically with technology and Internet ventures. The more I work with him, the more I appreciate his experience and wisdom and the more I realize how critical a good CFO is. Keep in mind that we don’t employ him on a full time basis, he’s a consulting CFO. Financial strategy, projections, etc., is one area that I’m not savvy in, so having a CFO who can work with me to layout the financial plan, who can work with the board of directors, who can work with my bookkeeper, and office manager, and who understands the scene is just absolutely mission critical. We made a mistake a couple years ago, working with a “CFO” who wasn’t up to par. Well, that’s a mistake I won’t make ever again.

Obviously there are other key relationships that need to be built and cultivated in a startup, but also over the longer term for an entrepreneur. I’ve talked about the importance of good advisers previously, and how hard it is to find them, but I’ve neglected to talk about these service providers. Having good service providers, and top-tier service providers like those I’ve mentioned, brings a certain amount of credibility and respect to the business just as much as having the right management team or the right investors. These folks need to believe in you just like a good investor or employee would. That is the basis of the relationship - trust, and believing in the entrepreneur(s) and in the plan. With that trust comes a relationship, and with that relationship comes top-tier services, credibility, and it puts you in a leading class in the entrepreneurial community. Lastly, I believe that if I do a good job with CitySquares, and if I decide to build another business afterwards, that I’ll be able to count on these folks to go for another ride with me - at their own risk of course!

CitySquares, Entrepreneurship, Networking , , , , , ,

Introducing The CitySquares Company Blog!

March 11th, 2008

Your Suspect has always been about my experiences and perspectives as an entrepreneur running CitySquares.com. I started this blog in the early days of CitySquares, the sweat equity days. I’ve tried to hold back from doing too much of a PR spin on things and just try to give it to you raw and real. In doing so I feel like I’ve also a bit of a disservice to my company by not talking about certain CitySquares specific things like new products, features, campaigns, traffic, sales, other stuff - stuff that can only be reported from the battlefield. This blog here, at Your Suspect, is my blog, and my opinions are not those of CitySquares. And now we have a place for that - at The CitySquares Blog!

A quote from the first post on The CitySquares Blog:

This is the start of something new. I’ve been blogging for quite a while on my own personal blog, Your Suspect, which is both about CitySquares and local search but really more about my perspectives and experiences as an entrepreneur. I’ve been blogging about such things since the earliest days of CitySquares but I’ve always wanted to give Bob, my cofounder, and other coworkers with a place to let their voices be heard from a company perspective, within the trenches.

Rest assured though that this blog here, at Your Suspect, will continue to be as it is - honest, a little brash at times, opinionated, and authentic. I hope you will enjoy both blogs!

So without further ado I invite you to jump over to and subscribe to The CitySquares Blog.

CitySquares ,

Evolution in the Startup

February 22nd, 2008

As CitySquares has grown over the past 9 months or so, from 3 people in my basement to 14 people in a South End office space, we’ve all had to grow and evolve. I believe the expression is, “A rising tide lifts all boats.” Unfortunately I don’t think that’s 100% true in a startup company. Just because the company is growing and is achieving measurable success doesn’t mean that everyone is going to be able to grow and adapt to the changes. And in a startup things can change daily. It’s survival of the fittest and that includes me.

Much of my job as the founder and CEO, among other things, is to make sure that we, as a company, are adapting to change, learning lessons, and applying today’s lessons to tomorrow. But that applies to me, individually, too - I must adapt to change. I must learn lessons. I must apply those lessons to tomorrow.

I could give many examples, from changes in the market place, to changes in the economy, to changes in the company. I’ll use morale as a specific example though. It’s a constant issue, always needing monitoring and attention - like a delicate plant that needs just the right combination of water and sunlight. If you overwater it, you’ll drown it. Too much sunlight and you’ll dry it out. Too much attention to morale in a company and you set a precident and shit doesn’t get done. Too little attention to morale and you risk a coup! Morale doesn’t just mean fun either. Morale is many things, and first and foremost it’s spirit. It’s like being an athlete and not being what you wear. If you’re a Boston Red Sox player - you’re part of something bigger - you represent the Red Sox. You better believe in it. You better buy-in to it. And that’s a challenge - getting your teammates to also buy-in. Without buy-in, you don’t have spirit. Without spirit, you don’t have people that care. And it’s all downhill from there. So before you can have fun, you gotta generate buy-in.

If evolving isn’t simply adapting to change, for the better, than I don’t know what it is. The only way to know is to wait and see the results. Evolution is a slow process, but the results can be seen quite clearly. I can confidently say that everyone is evolving and therefore, CitySquares is evolving.

CitySquares, Entrepreneurship , , ,

The Importance of Good Advisers

January 15th, 2008

Being that CitySquares is my second business I understand how important it is to have advisors - good advisors - and good advisors are hard to come by.

In my first business, which I started with a technician’s mindset (See E-Myth), I brought on some “advisors” and paid the price - in more ways than one. I brought in people who I thought I could learn from, who I thought I could grow my business with and in return provide them with some real interest in the company’s growth. What I ended up with was whiteboard sessions that went nowhere too often, overly complicated product ideas, and more messes to clean up. After giving it a good solid shot for a year I had to end it. It was painful, very painful, and cost a lot of money and time. It was a good decision and I learned some extremely valuable lessons from that experience.

When Bob and I started CitySquares not a day later did we decide to build an advisory board made up of people we could a) trust and b) who didn’t immediately want something from us in return. Those two qualities ruled out a whole bunch of people over the course of a few months. We quite literally interviewed people! I remember some of them read about us in the paper when we were just starting out, and they were very eager to “work with us.” Well, what that really meant was they wanted to do any number/combination of these things:

  1. draw pretty pictures on a whiteboard and show off how smart they are
  2. convince themselves of how valuable that MBA is
  3. carve a notch into their belt - like its another credential
  4. get-in with any board members/investors for their own selfish reasons

And in return they wanted equity, a seat on our board of directors, introductions to investors, even cold hard cash.

When it was all said and done what we ended up with was a small advisory board made up of a few people who came to us in very unexpected ways, and who …

  1. totally bought into our vision
  2. totally bought into our business model
  3. totally bought into our mission for locally owned business and real world community

These advisers wanted nothing in return for their time and for their brainpower - and I’m not exaggerating. I’d press the issue with them over coffee, lunch, whatever, and I’d insist that we put something in writing - and they’d insist “what’s the rush, Ben?” and “there will be plenty of time for that, Ben.” and “let’s just get Citysquares to [milestone] first.”

These folks are my most trusted advisers today. I have the utmost respect for them in so many ways and they continue to provide immense value to me and to the company, from referring us to others/others to us, to attending various meetings, to taking calls from me at various hours and in some instances working with some of my staff on things. The value is immeasurable. And yeah, now they’re all under formal agreements with the company and I sleep better at night because of it.

The point here is …

  1. Finding good advisers is extremely hard
  2. Bad advisers can be costly - even devastating
  3. they likely end up coming to you in unexpected ways
  4. they don’t want anything in return (within reason of course - I do suggest picking up the tab on lunches, coffees, beers, whatever, and going to meet them where it’s convenient for them - always)
  5. when you got one, you’ll know it
  6. when the time is right, be sure you know it!
  7. offer them your best deal
  8. Thank them often - you’ll need them when times are good and when times aren’t good.

CitySquares, Entrepreneurship , ,