Your Suspect

I had an appointment that got rescheduled today so I thought I’d use this time to talk about the upgrade to CitySquares.com. The best song just came on my headphones too, and it’s putting me into just the right frame of mind to type this up. The song is Underworld’s Rez/Cowgirl Live @ Glastonbury 1999. I’d just gets me going. I’d go to extreme lengths to go back in time and be at that show.

Alright, so that being said! Here goes it…

In summary, CitySquares.com version 2.0 will include more content, more communities, a much improved user interface including some very nice new colors and styles, a greatly improved user experience, better searching, more metadata, more intuitiveness, better mapping, more robust business profiles, user profiles with a bit of “social” sprinkled in, flickr photos and API stuff, super SEO, and generally speaking lots of little bells and whistles to make the user experience more intuitive and engaging.

With this upgrade CitySquares.com will be about diving deeper into our communities and neighborhoods and extracting as much metadata as we can and presenting it online to you. The first and most basic iteration of this strategy goes live on the 15th but ultimately the metadata is going to be provided and organized by you, the hardy, tax paying people of America. How? That will be revealed later next year. Businesses will be able to provide metadata, along with people young and old, dogs, pigeons, even lawyers. More meta more meta more meta! That’s my mantra! GIMME MORE META!

The user experience is going to be dramatically improved in the usual ways that you’d expect, like a new user interface, new color palette, and navigation.

In terms of user experience and navigation, I’ll try to explain it as simply as I can without a visual aid. First, Ian Wight at Urban Mapping announced our deal and that’s a big part of what we’ll be bringing to the users (reminder to self: call them “people”). So people will be able to navigate their way around the site by zooming in and out of communities. What that means is that you’ll be able to start your experience at a Regional level (metro-Boston) and drill down to a City (Somerville) and drill down to a community (Davis Square), and all along the way the content (i.e., business listings) is being filtered according to what layer you’re at in the geographic funnel. You’ll be able to move around at that layer across the categories, which are available at all levels of the funnel. You’ll be able to go even deeper and locate, say, bars within 10 blocks of a particular restaurant. Or shoe stores within 10 blocks of your home, or 5 miles from your office. Those locations, by the way, can be part of your user (people!) profile (i.e., Home, Work, Other). One more thing - if you can’t find the right business within the parameters you set, you’ll be able to look in the next closest neighborhood(s). So if you don’t find a liquor store (I must really want a drink right now) within 10 blocks of x address, we’ll show you the next closest neighborhoods in order of any proximity you set for yourself. All this is presented very intuitively (at least we think so). Oh, one more thing - Bob showed this to me today - when you type into the location box “downt” it will automatically show you locations in our site that begin with “downt” - like, downtown Boston. This will be done for all nodes in our network. Once you’ve created an account for yourself, you’re Home, Work, or Other location will be your home page. That might be a neighborhood, a city, or a region, it’s up to you.

Is this rocket science? No, but it’s pretty effen cool! And hey we’re not a technology company and we don’t need rocket science. It’s just cool and it’s sets the stage for so much more. You can make your own assumptions and draw your own conclusions about what comes next, but there’s a lot of opportunity once this groundwork is layed down. Most of this is made possible by Urban Mapping.

Each Region, City, Community will also have it’s own home page. That home page will be auto-generated, pulling in metadata from itself, pulling in flickr photos tagged appropriately, and displaying content based on its geographic filters.

All mapping on the site will be done with Microsoft Virtual Earth.

Because we’re building this on Drupal, our options for search and indexing are pretty open. Drupal’s native search engine is quite good and there are many modules that we can use to enhance it, and build upon it. A major part of our upgrade is a metadata system. That might not be that apparent at first, but it will become increasingly necessary and critical not long after. Managing so much content can only be done in one way - tagging and metadata.

When we launch the new site we’re launching not just the same ol’ ‘hoods and businesses, but we’re launching virtually all communities within route 128. This is a big step for us. We’re going from the twenty-something neighborhoods we have today, to countless neighborhoods in metro Boston. That also includes about 45,000 businesses (provided by Localeze).

All these businesses will be given free profiles, as always. Businesses that choose to enhance their profiles can do so, and those Deluxe Profiles will include a lot more than we’re providing now. That’ll be fun. Customers will also have the chance to sign up for Constant Contact newsletters, which will be a lot of fun to sell. Constant Contact has made it very easy for us. That takes us down a very interesting road, one with great potential for pushing content (newest businesses? changes to businesses? special offers from businesses?) via email based on geographical and/or categorical parameters.

User’s will have profiles too, much like any other site out there today. So People Pages will be full of all the info you’d imagine and more specifically as it would pertain their consumer tastes. Think favorite businesses, latest reviews (”Experiences”), their friends and neighbors, pictures, etc etc.

I haven’t spoken much about SEO yet, but that’s a huge part of what we’re doing in this new release. Everything from page titles, headings, code syntax (i.e., <strong> vs <bold>), URL structure, and more, has been taken into consideration and implemented very diligently. Thank you to my friends at KoMarketing Associates for their help with this.

We’re also using OpenAds for our display ad system, and we’ve created a number of ad zones within the various Drupal templates. The power of Urban Mapping and OpenAds will allow for a richer geographic advertising experience than any IP targeting crap out there today.

[brief silence]

Well, I just had Bob read this over and apparently I’m spot-on and, as he put it, “you didn’t promise the world.” Who does he take me for anyway?

So that pretty much covers it. Looking over this post it looks like we’re doing quite a bit, and rest assured, we are.

CitySquares CitySquares, citysquares.com, underworld

At the risk of sounding hasty and secretive, I need to keep this brief, but I promise more info will come shortly…

CitySquares is seeking testers. We’re about 1 month from launching the new and greatly improved Citysquares.com. It’s a huge upgrade, and a vastly improved experience for people (they’re not “users”!) and for businesses. While the new site will be ready to be previewed on an invitation basis in about 2 weeks, we’re going to need some testers. This is a great opportunity for teenagers, after school, and for college students looking for an extra buck.

We’re not totally clear on how this will work, but we envision something like this:

• Testers must have their own laptops.
• Testers come to CitySquares’ office in the South End of Boston during specific hours, each day for a few days in early October.
• Citysquares will pay testers.
• Some testers may be able to work from outside the office.

Again, there’s more info to come on the new site, and also on the testing schedule and those details. But if you are interested, please email us at testing@Citysquares.com.

CitySquares citysquares.com

So today we hired our first full time engineer. (for those of you who expressed interest in the job, thank you!) And in doing so we came to a resolution about technology, and then some actually. We decided to choose Drupal as our platform of choice for the future Citysquares.com. After much deliberation, debating, discussing, and consulting with ourselves and with others, about going with an MVC framework (e.g., CakePHP, Symfony) vs. Drupal, we finally opted for Drupal. The primary reasons are as follows:

• Body of work and knowledge. There’s a huge Drupal community, and it continues to grow and grow.
• Modules, modules, modules. Holy crap there’s a lot of modules.
• My blog is built on Drupal. Ok, that had nothing to do with our decision, but I’m just a big Drupal fan from experience.
• Scalability. Time Warner’s media sites are all built on Drupal. Sony Music sites are all built on Drupal. US magazine’s site is built on Drupal. ‘Nuff said.

There are many technical reasons too, many many many. But I won’t get into that - that’s very boring and this blog isnt meant to be boring.

What’s interesting about our decision is that by choosing Drupal, and choosing to work with the Drupal community that unavoidably comes with it, we are, in essence, choosing community. We are allowing ourselves to tap into a community, while bringing communities online, and eventually enabling other communities to bring themselves online. Argh!

This is actually deep stuff, to me anyway. In a more idealogical sense, choosing to go with Drupal is an indication of who we are as people, and as a company, and not just an indication of technical choices and skill sets.

I’m really starting to get into this whole concept of open source in business practice, in management, and almost as a mantra.

I don’t know, it’s heavy stuff and I’m really wrestling with it right now. More to come on all this, as I sort it out better in my head.

CitySquares, Computers cakephp, citysquares.com, cms, drupal, mvc, symfony

[This has been appended]

I’m not typically interested in taking the time to talk about my frustrations with companies who I’d like to work with, but this is very annoying. Over the past few months Citysquares has been working on building some nice partnerships. Some are content providers offering a unique niche offering that would fit nicely into our site, and provide the users, or businesses, with some nice value-add.

One example of this is Constant Contact, the well known eNewsletter company. I’ve had the great pleasure of getting to know one of their co-founders, Randy Parker, over the past several months. Randy has actually become an adviser to Citysquares, and an immensely helpful one at that. He put me in touch with Alec Stern, their Vice President, Strategic Market Development. Immediately, I was impressed with the care and attention Alec gave to Citysquares. Are we a massive account for them? No, not yet anyway. But see, that’s not the point and Alec understands that on many levels. That’s his job. And it’s my job to make sure these kinds of deals get done, so that we continue to provide more and more value to our audiences.

That is an example of a good partnership, already. Even though I haven’t signed the docs yet, it’s just a matter of days, and Alec and I ping each other often just to keep the momentum.

Here’s a bad example:

Citysquares is about to launch some nice new features, things we’ve been talking about for a few months but have finally invested some dollars into. These aren’t world changing features, but they’re big additions for us. The work we’re doing now is going to lay the groundwork, technically speaking, for some pretty exciting features. But we need to lay the concrete first, which is what we’re doing now. So, before we can launch, eh hem, “user generated” features like events, activities, even our own twist on citizen journalism, we need to pull in some content in the meantime, RSS feeds. Standard stuff. I happened to be doing some homework this past weekend on who’s pulling events and news feeds, and from where. Upcoming is a big one, for events. Townonline.com used to provide feeds for their many papers, but they don’t seem to anymore.

Boston.com is yanking events from a site called Zvents.com. I spent some time on Zvents this weekend and was quite impressed with the content they seemed to provide - a lot of it. They’ve got some pretty nice filtering abilities too. And best of all, I can pull that query/filter from their site in a feed. Oh, well, that’s what I should be able to do. After spending about 2 hours going through the painful process of running queries, sorting them, and noting the RSS URLs, it turns out - they don’t even work.

So ok, they don’t work. Not the end of the world. They’ll fix it, right? Won’t they? 24 hours later, not fixed yet. I send them an email. No response. Still not fixed. I send them another email. No response. Still not fixed. I send them yet another email, and test again, nope - still not working. So at this point, I honestly don’t even care if they fix it. Why would I want to use them now? No thanks. Looks like Upcoming is our choice for now. Not a bad choice, especially because at least those work.

My point? Don’t offer a service that’s broken. And if it’s a technical glitch, people will understand, but at least have the sense to respond to their emails. That’s just business 101 - talk to your customers and users.

A few days ago we had a user go on Citysquares.com who added six reviews within a very short period of time. And let me say - she is not getting paid for that (at least not by us). I made sure to send her a personal thank you email, welcoming her to Citysquares.com, thanking her for using the site, and for her content. I did not hear back from her - but that’s ok. I did what I know is the proper thing to do. Recognize that a user not a “user” - they’re a person, with a pulse. And that person can very quickly impact our brand.

Anyway, enough. I think I’m a little sleep deprived. I’m getting testy. Good night.

Update on 2007-03-06: I have been exchanging numerous emails with Tyler at Zvents. It’s been a total pleasure working with him, and I can say that I am now a happy Zvents user. Although we haven’t yet launched the Zvents features on our site, I am comfortable moving ahead with them and Tyler has given me some confidence that these technical matters, as well as the communication matters, should not resurface again

Local Search, New Media and Web 2.0 citysquares.com, constant contact, zvents

I’m going way out on a limb here, and surely many of you may disagree with me, but I feel pretty strongly about this, as a serious consumer and as a serious business person running a startup that connects consumers with local merchants.

Greg Sterling posted an interesting piece on his blog today titled “Opportunity: Online Reputation Management.” I can’t debate the logic here and the basic point that it makes, but I think that the reality of user reviews and how they may or may not influence consumerism is much deeper than indicated. I also think that the user-review value proposition for small, local merchants is not a strong one.

Citysquares.com offers users with the ability to write reviews for local merchants. An interesting example of this is for a new coffee house in Central Square Cambridge, called Andala. It’s probably the best example you’ll get in any urbanized area of the typical small business just getting off the ground. They’re not a Citysquares.com customer (yet). I’ve been there, with my wife, and Chris has been there a few times. I really enjoyed my experience there, and I posted a review. Why? For two reasons: 1, because I truly enjoyed my experience so much, I found the atmosphere, the coffee (I’m a coffee fanatic), and the pastries and so forth very good and it reminded me of my visit to Beirut Lebanon a couple years ago. My wife also really enjoyed it. That experience was, on a scale of 1 to 10, a 9. That’s how strongly I felt about Andala so I posted a review, once I returned home. The second reason is because I want their business and I genuinely want to help them succeed.

Here’s the problem. I am founder and CEO of Citysquares.com, and for better or worse, I only post reviews for local businesses when I feel strongly compelled. I think I’m a typical consumer too - discerning, choosey, but reasonable. I believe that I am like the vast majority of consumers, of all ages.

Ask your friends, ask your family - how many of them add reviews for local businesses? How many of them make a choice to shop at local merchant A vs. local merchant B because of some stranger’s review? I think you’ll find the answer, as we have found, to be not too surprising - that it plays a very insignificant role in local consumerism. But let me stipulate one very significant factors: I’m speaking about local merchants - not products! I’ll get back to that in a moment.

Here’s what I’ve concluded about reviews for local merchants: For the most part, their nice to have, their moderately helpful for a small slice of the consumer market, but by and large, most consumers don’t find reviews of local businesses really all that relevant or meaningful. However, that whole reality gets flipped over on it’s head with one simple difference, and that difference is the almighty dollar. How much cheddar do I plan on spending? That’s the critical factor here.

Whether it’s for a local shoe store, pizza pie, a bar, or for the closest Bank of America, user reviews just don’t carry much weight with the typical, and more importantly, LOCAL consumer.

Now, let’s say I was going to take Ali out for a nice dinner, perhaps within a 30 minute radius of home, somewhere we’ve never been? I plan on dropping a little more loot, having a bottle of wine, in a quiet, romantic atmosphere. Suddenly what other people have to say means more to me. Even still, for me, unless the reviews are dramatically, and powerfully positive or negative, they don’t really impact my decision that much. I can’t think of any situation that user reviews would have a really big impact on my local shopping behavior. Ultimately, I’m looking for X, and I’m looking for it here.

Additionally, part of the fun I have shopping locally is having my own experience - not basing my decision on a stranger’s opinion. Ah, now that opens up a whole new topic doesn’t it - Trust. That’s where this is going? Well, not today.

Back to products. This is interesting because here’s where user reviews take front row - here’s where they take center stage. Product reviews!

Just this weekend I had to find a new boom microphone for my digital camcorder. I didn’t want the stock Canon boom mic, I wanted something else. But I read some reviews on CNET, and sure enough, I made my buying decision.

Take my BlackBerry Pearl for example - a huge jump for me. I went from being a long time and loyal Windows Mobile user to BlackBerry. Before I spent the moolah and made the jump, I wanted to know what others had to say - many many others. I wanted a big sampling of user reviews.

Take my Creative Zen, a new refigerator, humidifier, bicycle, pair of skis, golf club - you name it. I want to know what others have to say - really badly. I bought some new golf clubs this past summer - let me tell you - I probably spent 15 hours or so reading what others had to say about a wide variety of drivers and irons. I’m not exaggerating - just ask Ali, and my brother and father.

Ok, what’s the point here? The point is this: I think user reviews are important for every form of consumerism, whether products, services, local retail, you name it. But ultimately it’s all about the mighty dollar and the impact on me or others around me. How much money I’m going to spend, and how much that decision has an impact on me or others around me. High spend? High impact? Reviews matter. Low spend, low impact, reviews don’t matter.

So if I had a formula it would be:

Total Spend $
—————— = Relevance of user reviews
Total Impact
(distance, pleasure/pain)

That looks more impressive than it really is.

Amendment: Greg and I exchanged emails after he read this blog post and he reminded me of an interesting point that I forgot to address, and that is as follows: In our many many conversations with local merchants, be them in sales calls or for other reasons, local merchants are not terribly big fans of user reviews. They don’t want bad reviews written about them. Surely, they also need to understand that they have a job to do - and that’s to please every customer. Yet some customers simply can’t be pleased, and some use the Internet or a user review platform as a sort of anonymous soap box. Ultimately, user reviews will be a big part of local search and online advertising for the foreseeable future, and certainly that is true for Citysquares.com. But we respect the needs of the local merchants, and while we allow user reviews, we do need to take an editorial approach to them sometimes. Take Andala for example. The user jlobel actually used a word that we could not approve. We did not bar his review, we merely edited the word. If a local merchant believes we’re on their side, and trust us to take user reviews and that sort of content seriously, especially if they’re a paid advertiser, than everyone is happy.

Lastly, on Greg’s point about there being an opportunity for online reputation management for local merchant reviews, I totally agree. Whoever figures that out is one clever person!

CitySquares, Local Search, Locally Owned, Social Networking andala cafe, citysquares.com, consumerism, greg sterling, local business, local merchants, product reviews, reputation management, reviews, user reviews

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 ). 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!

CitySquares, Entrepreneurship, Local Search, Locally Owned bootstrapping, business model, citysearch, CitySquares, citysquares.com, davis square, delphi.com, diesel cafe, Entrepreneurship, frustration, history, launch party, Local Search, motivation, prospero technologies, sidewalk.com, somerville, spot story, story, webinno

So back on November 29th, we at Citysquares had the pleasure of being a ’side-dish’ at WebInno. Run by David Biesel, the event is, in my opinion, a hugely needed event for beantown. With all the amazing technology companies here in Boston, and the schools and the massive amount of brainpower here, it’s amazing to me that WebInno is really the only one of its kind here. I don’t know if there were other events like this in years past, but man oh man, this was long overdue!

When were were a side-dish at WebInno in November, I really didn’t know what to expect. We were fortunate to have been given the opportunity by David, on the phone, about 2 weeks before the event. We knew we’d have a side table (along with 3 other local startups) and would not be one of the main presenters. But that was fine, we were just glad to have the opportunity to strut our stuff. We wore our Citysquares.com polo shirts, had our tchotchkes all lined up on the table, plenty of computing power and some signage from past events. We were also lucky enough to be located next to the bar, which has its own innate benefits. Not 20 minutes into the event, we barely had the laptops powered up, were we getting hammered by the arriving attendees. We didn’t miss a beat though. As the night progressed, and the main presenters did their thing, I found that out of all the side-dishes, we had the most traffic and it was pretty steady all night. I don’t know why, but I can assume it was because a) we were next to the bar, b) we had our Citysquares.com attire on, c) we were on our toes, hopped up on coffee, and ready for anything, and d) we could answer every question that was tossed our way, with little or no hesitation. Hey, we’re very well put together!

The crowd was largely made up of local techies, but not the IT kind, not the biotech kind, the dot-com kind - and more so, the web 2.0 kind. Hipsters young and older, big thinkers, new entrepreneurs, veteran entrepreneurs, and yes, there were a small handful of service providers (buy they behaved themselves). Having “CEO” clearly printed on my name tag brought an overwhelming amount of attention and quizzing from all of the above. I was peppered long and hard with questions ranging from “what is your business model?” or “how many cities are you in?” or “how many advertisers do you have?” or “so how to you get to critical mass?” to “are you funded?” All questions I enjoyed fielding. Chris and Bob were busy doing the same thing - fielding questions and suggestions from everyone. They were cool, calm and collected, and having a ball.

At about 9:30pm, I was engaged in a conversation with Nabeel Hyatt and a friend of his from Yahoo!, and I looked around and noticed the hotel staff had begun cleaning up the room and we were the only company left! I was shocked! Three straight hours of talking, selling Citysquares.com to the crowd, and no dinner. I was exhausted but also exhilarated.

After the event Chris, Bob and I went to grab a burger and a beer to wind down and try to reflect on the experience. The word “whirlwind” was used many times.

Of all the intensity and excitement of the evening, we walked away with two valuable and intangible results:

1. We received an unbelievable amount of positive feedback and energy from virtually every single person who came by. Across the board, everyone was impressed with what we’ve accomplished with what little we’ve had to work with, and we were reminded just how far we’ve come in the 13 months since we launched. It’s hard to explain how thankless sometimes running a startup can feel - how grueling, and stressful it can be for us as professionals, and in our personal lives. The WebInno reminded us what it’s all about, and just how far we’ve come and how important our mission and vision really is. That is so valuable.
2. Connections connections connections. We met so many people and made so many powerful and valuable connections. I met CEO’s of companies that have been on my radar for many months, investors, service providers, and many entrepreneurs who are confused or struggling to get out of the gates, and entrepreneurs who’ve been-there-and-done-that. Now, two months later, I’ve been able to further many of those relationships along. One of them is blossoming into a new adviser to Citysquares, another is looking like a potential business development partnership, and many others are turning into early friendships based on mutual interests.

Last night I had the pleasure of returning to WebInno, but not as a presenter or side-dish, rather as an attendee. I met up with a few people I had planned to meet there, and with little delay, the whirlwind began again. Prior to the first presentation by GuildCafe, I met up with our PR consultant Matt Ellis. I told him about the event a few weeks ago and he seemed very glad to be in on the secret. After the presentations I was swept back up in the energy of the room and was approached by people I’d met at the last event, and, overwhelmingly, people I hadn’t met at the last event but who’d heard of Citysquares and had questions or comments about the site. Again, the energy was palpable and fun. Last night, the crowd was about 30% more than last time!

The “Main Dish” presenters were as follows:

1. GuildCafe. Presented by Jon Radoff. A very well designed, seemingly very infectious social networking platform for online game players. What I love about GuildCafe is the immensity of the market! No doubt, online gaming is big, and getting bigger. I strongly believe that in 2007 online gaming, especially MMORPGs, will capitivate a worldwide audience and, much like MySpace did two years ago, really shake things up. GuildCafe is poised to leverage this momentum and build a very large, sticky, social network for gamers. I look forward to seeing them blossom! Jon Radoff did a great job presenting - very charismatic and good humored.
2. Punchbowl Software. Presented by Matt Douglas. Mypunchbowl.com is a new web application that provides an easy, comprehensive, and personal way to plan an at-home party. Matt did a nice job presenting this (pardon the comparison) evite on steroids. That’s the only brief way I can word it. It’s a unique twist on the online invitation model, in that it provides quite literally everything you might need at your finger tips to plan a party. I have to say that the use of AJAX was a bit over the top. I like punchbowl, but I wonder if it’s just a little too much? evite did what they did (and continue to) because it’s simple - its easy and it doesn’t require too much thought or time. I have to plan a graduation party for my wife soon, and hey - I just may use punchbowl! So we’ll see if I can deal!
3. Goombah. Presented by Diane Sammer. Goombah is an exciting new product for music discovery, music, promotion, and social networking based on music taste similarities. Goombah is cool, but the first thing that jumps out at me is the word “goombah” - the offensive use of the word. That aside, right now Goombah is entirely dependant on iTunes. I, for one, am not a fan of iTunes and the iPod - for many reasons. Goombah is onto something here though - I like the idea of being able to look at music that other people are listening to, who share my music tastes. I have 18 GB of music on my server here, and sometimes, believe it or not, I get bored. That’s when I use Rhapsody and tune into some channels. I’d love the ability to find others who like the same music that I do and check out some stuff they have that I don’t. If Goombah works with Rhapsody someday, I’ll give it a shot.

The side-dishes were DoodleBoard, Geezeo, MobaTalk, SpotStory, and TrustPlus. As I mentioned earlier in this post, I got swept up in the whirlwind and just didn’t have a chance to talk to any of the side-dishes with the exception of a brief chat with SpotStory at the end of the evening.

Anyway, that’s my long (very long) review of the WebInno event. I definitely plan to keep attending these events. But don’t think I’m going to be this verbose after each event.

Entrepreneurship, Networking, New Media and Web 2.0 boston, cambridge, CitySquares, citysquares.com, geezeo, goombah, guildcafe, matt ellis, punchbowl software, spotstory, startups, webinno

John Kelsey has a nice piece on The Kelsey Group blog about Sidewalk.com, and Steve Ballmer’s regrets of dumping it. I have to admit that it’s nice to finally see some acknowledgment by Microsoft that this was a mistake. Because that’s ultimately what it is. Sidewalk.com was a fantastic site back in the day. In the mid/late 90’s I used Sidewalk.com quite a bit. I used it to find music shows in Boston and Cambridge, to find restaurants, and so much more. I really think Sidewalk.com was one of the best “local search” sites that’s ever existed - and mind you, that’s before the term “local search” was ever in our vocabularies. Every since Citysearch purchased Sidewalk from Microsoft in 1999, I think it’s fair to say a lot of people were disappointed. I remember just a few months ago I was presenting Citysquares.com to a group at Babson and I fondly mentioned Sidewalk. A couple people in the audience quite exuberantly nodded their heads as if they knew exactly what I was fondly recollecting. Over the past year or so, fans of Citysquares, or just about anyone that I’ve mentioned Sidewalk to, also have fond memories of Sidewalk. Anyway, suffice to say Sidewalk left a very good impression with a lot of people.

Can there ever be another Sidewalk.com? I don’t think so. It was the Model T - the first of its kind.

CitySquares, Entrepreneurship, Local Search citysearch, CitySquares, citysquares.com, Kelsey Group, Local Search, sidewalk.com