Citysquares.com: Part 1

Today I had a meeting with the founders of Spot Story, Aron and Matthew. I briefly met them at WebInno last week. It was at the end of the evening and the room was clearing out, they were still fielding questions and performing demos. We spoke for a couple minutes, exchanged business cards and promised each other we’d speak over the coming days. Today we did that, at Diesel Cafe in Davis Square. During our long, and caffeinated, conversation they asked me about the back story to Citysquares. It was the first time I’d heard that question in a few weeks. As I was telling the story I thought to myself how I hadn’t really told the story on Your Suspect. So, here goes it…

As I mentioned in a previous post, I had been a loyal Sidewalk.com user in the mid/late 90s. I found it exceptionally useful and more readily available than some of the local rags in town. Sometimes I’d find a great event or restaurant on Sidewalk and I’d head out with some friends for a night out on the town. I would tell friends about Sidewalk.com and they’d become loyal users. Eventually Sidewalk.com was gone, and replaced by Citysearch. I was never able to get the same enjoyment from Citysearch. Sidewalk.com was my first experience with what is now coined ‘local search.’

Well, as the years went by and I established roots in Somerville, mainly in and around the Davis Square neighborhood, I longed for something like Sidewalk.com. I worked at Delphi.com and Prospero Technologies starting in 1999 and ending in 2001 (after surviving 3 rounds of layoffs). Those were the dot-com boom days. Even then, with all the hype around this whole Internet thing, I grew exceeding frustrated with the lack of localized content. I still couldn’t adapt to Citysearch. Other local sites like The Boston Phoenix, Boston.com, and maybe a couple others, just didn’t do it for me. I still couldn’t find truly local content.

So this continued throughout the next few years. At times, I’d voice my frustration about this to my wife and she’d agree with me – why can’t we find the hours for her hair salon down the street? Doing a web search (now called “googling” by many) would yield very little, if any, local information about her hair salon. This was frustrating. So we’d pull down, from atop our refrigerator, an old, dusty copy of the Verizon Yellow Pages. It may have done the trick, it may have not. The frustrations remained with us.

In the winter of 2003, it was late at night and I was sick with a really bad stomach bug. I was very ill. I needed some medicine – just something over-the-counter to help me get through the night. Ali was at her sister’s house in New Hampshire for the night. Just down the street from us, here in Davis Square, there’s a pharmacy. For the life of me, I can never remember which pharmacy it is. Is it a CVS? A Walgreen’s? Brooks? I can never recall. Ali laughs at me for this a lot – and I laugh too. But at the time, it wasn’t funny. I’m not exaggerating when I say that it was winter, it was Boston, and it was very cold and even snowing. The circumstances couldn’t have been worse. The problem I was faced with was this: I don’t know which pharmacy it is, I can’t find anything online, I don’t have a phone book anywhere (that I knew of) and I either tough it out and be sick all night long, or I brave the elements and walk into the square to see if the pharmacy was open. That’s it – I just needed to know if the pharmacy was open. If it was open, ok, great, I can find some medicine. If not, I’m in a jam. Ali has the car. What to do, what to do. If this information was available to me online, I could make an easy decision. So, I bundled up and walked into the square only to find out that Brooks Pharmacy was closed. Needless to say, my night only worsened.

It wasn’t long after this event that I’d contemplated building a very basic website with a listing of all the businesses in Davis Square. Davis Square has a vibrant and moderately young demographic. Back in the day, Davis Square was a little seedy, but up and coming. In the 90s Davis had blossomed into a vibrant somewhat trendy community but still with a truly local and Boston kind of feel to it. And Tufts University is right down the street so surely a more transient crowd would dig something like a free online resource listing the businesses and other local resources. (Interesting side note, in 1997 Davis Square was called the hippest place to live in the US by UTNE Reader)

I decided to pursue this idea. I set out to buy davissquare.com. It was already owned by someone (still is), and my negotiations with him went nowhere fast. When I briefly explained to him what I wanted to do, he wanted to be my partner. But I wasn’t looking for a partner, I wasn’t even looking to make this a business. I was just looking to build a really simple, even bland, web based directory of all the businesses in Davis Square. That’s it. No business model, no purpose other than scratching an itch. I didn’t get far with buying davissquare.com. Discouraged, and preoccupied with life, I let the idea slip away. It never quite left me though. From time to time over the coming weeks, months, years I’d become momentarily inspired to do it again – but it never went anywhere.

Fast forward over many less significant but similar moments and experiences trying to find local businesses online, but ultimately resulting in frustrations, to the summer of 2005, August 13th to be exact. I’d been shaving my head for several years, by myself, at home, with a Braun clipper. It was a Saturday morning around 7am, and I was going at it in the kitchen. Standing up, facing the floor, with the clipper shaving the back of my head, watching the short hairs fall to the floor in neat clumps. Just then, the clipper started making noises – scary noises. The kind of noises that make you think holding an electric tool to your skull is a really bad idea. It started vibrating in an odd way. My head was barely shaved! It can’t break now! But it did. After several convulsive vibrations and erratic movements and frightening noises, it stopped working. I unplugged it and just stood there in the kitchen, staring at the clipper, and thinking how I must look like a total freak with only the back of my head shaved. Now what was I to do? I had to find a barber.

Now, mind you, the biggest reason I started shaving my head several years ago was because I’d grown frustrated with the local barbershops. No matter where I’d gone, they all did a lousy job. I’d even gone so far as to go to a couple salons. But I don’t like the salon experience. I grew up with barbers all my life. As a kid, my father and I would go to the same barber every two weeks, for years and years. Now, I was in a situation where I’d desperately needed a barber or a salon – anything to help me.

Here we go again: I “googled” (sorry Google lawyers) “barbers davis square” only to be presented with basically nothing (note that now, when you google “barbers davis square” the first result is for Citysquares.com Laughing). I knew there was at least one barbershop in Davis Square, but it was 7am – were they open? Yes – the same problem folks. The phone book was no help to me because I didn’t know the name of the barber shop I was looking for. I only knew it was on Highland Ave. But what number Highland Ave? Was it 16 Highland Ave or 1600 Highland Ave? Thankfully I wasn’t dealing with a violent stomach illness – only a massacred hairdo. I knew I’d survive this. So I put a hat on, and walked into the square. Guess what? The barber shop was closed. So I went and got a coffee, and soon had a repaired hairdo. The barber had a good laugh.

On Sunday, August 14th, my wife and I were talking, once again, about just how frustrating it was to find any truly local information about the businesses in our neighborhood. What is wrong with the world!? Why is this so difficult? And there it was – square between the eyes – I’m going to do this. Finally. I’m going to create this! No more davissquare.com negotiations, no more frustrations. It’s time for me to do this.

I sat in the same chair I’m sitting in right now, in my living room, and just let the ideas flood my brain. They kept coming. I just started writing the ideas down. I started thinking of brand ideas, domain names, content and feature ideas. Then it hit me again – open source. It’s so easy to build websites now, to build online applications, content management, whatever it was I wanted to do it was nothing like the old days of the web. It wouldn’t cost $500,000 and half an army to build it, and still take a year.

As I became more excited about the idea, I still had the vision of this being a free service to consumers like myself. I didn’t have a business model in mind, I wasn’t thinking about making money with tobedefined.com. I started to tell Ali about my brainstorm. She really is my better half and she has a very good instinct for things – be it people, ideas, just about anything. As soon as she let me explain the idea, she went nuts – she loved it. That was when I knew I had something. It wasn’t because of anything other than Ali’s enthusiasm that really got me moving. I started tossing out domain names to her: Neighborhoods.com? Nah, that’s gone. Cityblocks.com? Nah, that’s gone. Countless others. Ali said, “Citysquares.com?” I said, “I thought of that but I’m sure it’s taken. It’s gotta be taken.” Sure enough, there it was – available. I wasted no time. Nine dollars later the domain was mine.

More ideas flooded my brain, and I couldn’t write them down fast enough. Then I saw the business opportunity. Local businesses, merchants, moms-and-pops, whatever you want to call them – they had to agree, right? They had to see the light too! I mean, they advertise in newspapers, and in the phone book, and a small number even do online stuff, and I already knew for a fact that 60% of all small, local merchants didn’t have a website, and those that did only had brochure-sites. Even those brochure-sites aren’t updated often, if at all. So there was the real heart of it – a lack of an easy way for a business, like a barbershop or a local apothecary, to advertise online and just make their relevant business information available in a single, online, consolidated format. The idea was getting legs, very quickly. It was growing by the minute, but also getting more complex. Just the thing I was looking for.

My next step was to make a call. Bob Leland, my good friend and a colleague of mine at the time, was a brilliant UI and UX guy. He was as good as they get, and more importantly, we’d worked together for quite a while, though thick and thin, and he was my go-to guy for creative visionary type stuff, for online product positioning, for bringing an idea from my mind’s eye to a presentation format. I spent the next two hours on the phone with him, while pacing around my porch, sipping a beer. We just went nuts dissecting the concept and really asking ourselves if this made any sense. He could totally identify with my frustrations with Citysearch and Yellow Pages, and the lack of this kind of information in general, online. Bob loved it, truly loved it. After more than two hours on the phone, we agreed that we’d let the idea sit for a couple days and think about it further and let it all sink in. So, we did.

Over the next two days the idea grew and grew, and the notepads piled up. Ali’s enthusiasm grew as much as my own. On Tuesday, Bob called me and told me he had something he wanted me to see. He sent me five jpeg files with instructions on the order I should open them. They were comps – static graphics for his vision of Citysquares.com. I was floored – absolutely floored. Stunned and floored. I remember the energy and adrenaline swelling inside me when I saw his graphics bring my vision to life.

Over the coming days we had the early makings of a real business. I managed to pull my father into this, and my good friend Chris Miller. On October 13, after 6 weeks of non stop meetings, development, design, planning, and campaigning we had the first iteration of Citysquares.com up online and we kicked it off with an official launch party in Davis Square.

Bob is now my co-founder and VP of Product Development. Chris is our Sales Manager. Fifteen months later we’re still having as much fun as we were in August of 2005. The challenges are totally different now of course. We’re running an Internet startup. But we’re on a mission, and we’re here to stay. Make no mistake about that either – Citysquares.com is here to stay.

Looking back at all the incidents and motivations behind Citysquares, before it was really a concept, I’m really glad that I didn’t do it sooner. Any sooner and it could have been a real mess. The market is ready now, it wasn’t back a few years ago. The technology is available, and only keeps getting more exciting. Users weren’t totally there yet either. Now, in 2007, we’re in great shape to do what we envision.

As Citysquares.com stands today, as a website, a consumer-facing service, and a platform for local merchants to market themselves, we recognize that there’s so much more work to do. It’s not quite there yet. This is the infancy of Citysquares.com. We’ve got lots planned for the next few months, for 2007, 2008, and beyond.

I’ve made this long enough. I’ll follow up with more at a later time. There’s so much more to tell and I look forward to it!