As some of you likely know, it was announced in early December that CitySquares was sold to Backyard, a west coast based startup with funding from Google CEO Eric Schmidt, celebrity entrepreneur and investor Jason Calacanis, and self described greedy, blood-sucking venture capitalist Dave McClure. It’s not the investors that make Backyard exciting, to me anyway (although it certainly has a nice ring to it), it’s the founder and CEO Steve Espinosa. I’ve known Steve for a few years now, and at 22 he’s already a very well admired veteran of the Local space and I’d bet on him any day of the week. So it’s an honor to have sold CitySquares to such a great guy with an equally great vision.

Now that CitySquares is largely behind me (I will still be involved as an advisor), I’m moving on from Local. Plainly put, 2010 kicked my ass, and CitySquares’ prospects for regaining its edge wasn’t getting any brighter as this year passed for reasons I won’t get into right now (but I will once the dust settles). As Greg Sterling penned on his site announcing the acquisition of CitySquares,

Given the noise and competition now in local Saren is not unahppy about exiting the segment for now…When CitySquares launched, for example, there was no Google Places, no Facebook Deals, no Groupon and no Foursquare (et al).

There’s a whole lot of truth in those two sentences. More truth than you know. I can proudly say that CitySquares pioneered hyper-local search. No one was doing local search at the neighborhood level until CitySquares came along – and I mean really doing it at the neighborhood level. And to this day, I will boldly state that still, no one has the mashup of hyper-local geospatial data and local business listings that CitySquares.com has. Alas, the mobile platform is the future of local search, of hyper-local search. OK, it’s not the future, it’s the now! So of the many things I can hang my hat on as I close the door on my CitySquares.com chapter, this is one of them.

Another thing I can hang my hat on are my relationships with countless people, of so many background, cultures, and talents. I’m proud to call many entrepreneurs, investors, employees, associates, vendors, partners, across the country and in many corners of the globe colleagues, acquaintances, even friends. CitySquares took me places I never imagined going, both literally and figuratively. I’m most proud of this.

So it’s with both excitement and with sadness that I say goodbye to 2010, and with open arms that I welcome 2011. I will be making an announcement about my next step within the next week or two. In short, it’s a big change for me, and a change I’m thrilled about.

Before I sign off for the year, I’d like to wish you a very healthy, happy, prosperous 2011. See you on the other side!

Au revoir

I was asked to speak at the Marketplaces show alongside Colin Pape with ShopCity and David Vazdauskas of Local Thunder. The panel will be moderated by Steve Marshall, who I always enjoy. He doesnt pull punches and he adds a certain kind of intensity to the panels. I’m looking forward to it.

I’ll be at the show from Sunday through Wednesday with my colleague and VP National Sales Todd Salerno. We have a few meetings teed up but if you’d like to catch up with one of us just email me, tweet me or send smoke signals, whatever works for ya!

If anyone wants to go, but does not yet have tickets, please get in touch with me, I have a discount code for you to save a little.

Looking forward to seeing a whole lotta people! See you there!

“You stay classy San Diego” – Ron Burgundy

Related articles by Zemanta

• BIA/Kelsey Analysts Identify Key Local Media Trends to Watch in 2010 ()
• Marketplaces Conference: Mobile Sessions Slated ()
• CitySquares Acquires Online Retail Directory Yokel.com ()
• Figures Show that Going Local may be The Best Business Model ()
• Class action launched against Yelp ()
• BIA/Kelsey: More Than Half of All Ad Spending Is ‘Local” ()
• At The BIA/Kelsey Conference Next Week in San Diego ()

I believe that this local search thing is quite early, and to keep up with the Jones’ I’ve started to refer to it as Local 1.0. Hear me out here, because I’m diving deep.

Web 1.0 was a passive web, about adoption and about moving to an interconnected digital medium, and Web 2.0 is very much about participation, creation, and transforming that interconnected digital medium into a platform. Just as Web 1.0 was static, passive, and largely about adoption, so is local, today, and as we’ve come to know it.

Resourceful Idiot does a pretty decent job of explaining the iterations of the Internet. He starts by saying:

“You can group each of the ‘Web x.x’ as a different movement when it comes to internet usage. Web 1.0 is the movement that took place during the beginning of the internet.”

Web 1.0 was about adoption, and about the movement of media, business, and commerce, to the digital medium that is the World Wide Web. Everyone was moving online to reach a larger audience and achieve better efficiencies. The first to move was big media like newspapers, news stations, music, magazines, etc. Everyday services and resources went online, like the post office, libraries, phone books, the dictionary, the encyclopedia, public transportation services, travel agencies, shipping services, mortgage companies, banks, day trading. Consumer services, business services, B2C, B2B, all of them were moving their data and content to the web. All of this content was mostly static, and that was fine.

Lots of everyday people got online, mostly through dial-up. They got online with their brand spanking new Macs and PCs, they tied up their home phone lines, they even planned their evenings around it. Most people, in mainstream America that is, went to chat rooms, which was about the coolest thing going at the time, before anyone ever heard of “social networking” or “social media.” The web was new and there was so much to be discovered and explored. People struggled with actually getting value though, in their daily lives. What was there to do on the web but conduct research and join chat rooms and maybe pirate some music? I’m oversimplifying it a bit, but to mainstream America, this was the reality.

If you were entrepreneurial and had an idea for a business, like lots of the companies I helped out in the mid-late 90s, meant that you also had to host your own website. To do that meant you had to have a domain name, you had to host the site, hire an HTML programmer, maybe even an application developer to do ASP, a database administrator if you wanted to have dynamic content, hire a graphic designer, even an IT person to make sure you’re site was hosted properly. Want your own server? Pay up and collocate it somewhere. Next thing you know, you’re into this website thing for a budget busting amount, with more overhead than you know how to pay for, and human resources coming out of the woodwork. Moving your business to the Internet seemed like a mad dash to the finish line – either you get there now or you’ll be lost in someone else’s dust and live to regret it. if you didn’t get online, you were going to die. It was simple. Move or die.

So, over time, lots of industries did this. Big companies, small companies, new companies, old companies. But not all companies went the way of the web. Small businesses, mom-and-pops, brick-and-mortars, Main Street USA businesses – they didn’t. They didn’t care and mostly couldn’t afford it. To a lot of them it was a flash-in-the-pan, a fad that would pass like so many other things over the years and decades that supposedly challenged their businesses. Construction on the street is about as bad as it gets, same with recessions. This Internet thing was a joke. And the return on their investments were practically negative too. They’d spend money on these websites, and for what? Just to have a web page? So what.

In those days there was a lot of hype about e-commerce, which was probably the most exciting and radical thing facing consumers and retail cash registers, depending on how you looked at it. E-Commerce was going to destroy mom-and-pops! It was to be the apocalypse of brick-and-mortars, of retail, of traditional commerce, and we’d all be transformed because of it.

Then, along came a company called Sidewalk.com. Started in 1997, Sidewalk was a city guide – the first of its kind. There were a couple of other city guides, notably Digital Cities, owned by AOL, but Sidewalk was different. Microsoft owned Sidewalk and quickly turned into a top destination site. The popular website featured businesses, events, and activities for your city, and they even showed some of the content in a neighborhood context. You could find lots of local businesses on Sidewalk.com too. I remember using Sidewalk regularly in the late 90s, looking for things to do in Boston, shows to catch, clubs to check out, and places to go on a date.

Some argued that Sidewalk was arrogant and attempting to put city weeklies out of business. Some thought that Sidewalk was a glorified database of listings. In 1999 Microsoft sold Sidewalk to Citysearch. In my opinion, this was a mistake. Apparently Microsoft CEO Steve Ballmer agrees, as he recently stated,

“Sidewalk was really aimed at what we now call local search” and “Sidewalk is one we should not have gotten out of.”

In my opinion, this was the opening salvo of the Local 1.0 era. Everything until that point was irrelevant. Sidewalk made the first real impact and most people who know the local space, know Sidewalk’s story.

The burst of the bubble was in March of 2000 and the American economy entered a recession shortly after. If small businesses ever bought into this whole Internet thing to begin with, they certainly weren’t going to make the plunge now. Too many fortunes had been lost as a result of the crash. Too much hype around e-commerce destroying traditional retail. Too much hype, too much nonsense, not enough value. Business went on as usual for these guys. “Just a fad,” they all told themselves, “just a flash in the pan.”

For the next couple of years no one challenged CitySearch in the city guide space. The phone companies weren’t making much progress either, but they had traffic and they had the brand recognition. Yellowpages.com, Superpages.com, Bigyellow.com, they all had a huge opportunity in front of them. So did the newspapers. They all had a massive opportunity right in front of them and based on branding and market share and clout alone, they should have been able to do make moves. But they didn’t. They all stayed still and thought that print was the medium to stick with. When they did make the right moves, and started selling online ads to small businesses, they mostly sold them as add-ons to their print advertising products, which was their primary revenue stream for previous several decades.

So here you are – Local 1.0 at full steam now. The IYPs had a market to grab, the newspapers had a market to grab, and Citysearch had their piece. Right? No one could stop get in their way! Wrong! Out of left field, like a bat outta hell, came this new company called Google.

Google had been around for a couple of years already but it mostly appealed to techies who were plugged-in. The growth of Google usage was nearly entirely organic, through word-of-mouth. It was simply a better search engine, and soon, even soccer moms were using it.

By 2003, everyone was Googling. If you weren’t using Google, than you really weren’t using the Internet properly. Google simply provided a better experience when you wanted to find information on the Internet. The relevance of the search results was paralleled and the user experience was uncluttered. Suddenly, Google.com was the de facto search engine and if you were using something else you were just behind the curve.

Google then started monetizing by way of Adsense, and almost everyone jumped on board. Now, Google wasn’t the first to do this. Many folks used Overture long before Google was a household name, but through Google’s popularity, and through some differences in their approach, Google simply kicked ass. And ya know what else, they even started to penetrate the SMB advertising market. This meant the war was on!

Google also gave birth to entire industries, or, if those industries were already there, they were now exploding. Notable examples of this are Search Engine Optimization and Search Engine Marketing is another. SEO and SEM businesses are sprouting up all the time, mainly to help business get exposure on Google, lots of them are helping SMBs. Those very same businesses who didn’t want to get online.

Here we are now, in 2004, and we start hearing “Web 2.0″ being uttered from the lips of industry gurus, specifically Tim O’Reilly and John Battelle. Web 2.0 is still with us today, in late 2008, and it’s redefined our perceptions of what the Internet is, and shaped our ideas of what it could be. Web 2.0 has certain attributes that we could debate about, but mainly the core characteristics of Web 2.0 are participation, web based applications, community, lighter user interfaces, richer user experiences, openness in technology, and using the Internet as a platform, among other things. All of these things have lent themselves to new verticals on the Internet, like Social Networking (MySpace, Facebook), or the transition from static personal websites to blogs, or Software as a Service (SaaS, Salesforce.com), folksonomy oriented content and data sharing sites like Flickr and del.icio.us, and many more. But where are the small businesses? Everything in Web 1.0 and in Web 2.0 seemed to leave the small businesses behind. Why? Because they weren’t ready for an online identity, and they didn’t see a reason for it.

Like most people, you have some sort of online identity now. This is due mostly to broadband Internet access and affordable computers. The days of dial-up are behind us, and nearly everyone has a computer. To have a computer, to have broadband access, is to be a node on the Internet. Got an email? You’ve got an identity. Email is the linchpin of your online identity. Sign into any websites? You’re on the Internet. You’re only one small step away from joining a larger community, perhaps it’s MySpace, perhaps its Facebook, or Eons, or Jdate. You have an identity online, and more likely than not, you’re connecting with your friends there too, real world and virtual world friends.

All of this is appealing to some almost primal need that we all have as humans, and that’s a need to connect with each other in meaningful ways. It’s not enough for me to know that you exist, I want to know more about you, I want to learn about your attributes and characteristics that make you distinctly you. What makes Ben, Ben? Where are you? Where do you live? Where do you eat and hang out? All that is conducted locally. You life is conducted where you live, where you work, where you play. Your life is not conducted on the Internet. It’s conducted at home on the couch and at your kitchen table, but also at the subway station, at the local convenience store, at the library, at the farmers market, the bar, the ballpark, your cousin’s house. This is your life, your local life. Your local life is also, and greatly, where you spend your dollars, take your dry cleaning, find your plumber, and so much more.

So you have an online identity. Who’s left? Let’s see, users are online, and have been. Governments are online, newspapers, pornography – all online. More music is purchased online than any other method, thanks to iTunes. Even movies are online now, and if they’re not, you just add add a DVD to your Netflix queue. Enterprises, real estate companies, hospitals, libraries, everyone is online, well, that is, everyone except mom-and-pop.

What’s going on with mom-and-pop? The whole world is moving without them! Even the people who run these businesses, mom and pop, have online identities. You can find them on LinkedIn, on Facebook, but what about their businesses? What’s going on here?!

Here we are in late 2008, and Web 1.0 still feels like yesterday. Web 2.0 is moving fast, so fast that it’s simply leaving most people and most businesses in the dust. It’s hard to keep up with all this stuff unless your in the industry or just have a lot of spare time.

And SMBs are finally, finally starting to move online, but not on their own. They, like so many businesses in the 1990′s, need help, and they know that their customers use Google to find things. They, too, use Google to find things. They don’t have websites for their local businesses, yet 30% of all online searches (or ‘Googles’) are local searches – that is, consumers seeking local goods and services. I’ll say that again: 30% of all online searches are local searches!

This local search thing is very young. It’s still in its first iteration, not even close to a local 2.0. And just like with the early web companies, the early search engines, the early travel sites, there isn’t going to be just one winner. Citysearch has paved the way for folks like CitySquares. So have the traditional yellow pages, and the newspapers. This small business sector is always behind the curve, always behind the changes in the market. And for good reason.  But they’re moving now, they’re adopting the Internet because it makes sense for them now. Their customers are there, all of them. The extent of this today is limited to SEM (through various firms or direct with the search engines), their own website despite that only 55% of SMBs don’t have websites (and those that do are largely brochure sites, built long ago, and not SEO’d), and local search sites, city-guides, and directories.

Greg Sterling says it best,

“One of the most challenging aspects of local search is small business (SMB) advertiser acquisition. Everyone is aware, especially Google, Yahoo and Microsoft, that the US SMB market is where the advertiser volume is: almost 99% of US businesses qualify as small businesses (here defined as < 100 employees).

According to the US Small Business Administration (SBA), more than 20 million firms qualify under the definition above, with almost 19 million of those having no employees at all”

Greg even makes the argument that we’ll soon see the end of SMB websites. And I agree. As I’ve stated, these businesses can’t be bothered. The value does not match the expense. And ROI? Most SMBs don’t even know what that means.

Local search is so young, it’s Local 1.0. The shift to a Local 2.0 will only happen with the help, the encouragement, and the efforts of the IYPs, the city-guides, and local search players. No question the SMBs get it, no doubt about it, they’re just afraid. They understand the value of the Internet, and research is showing a dramatic shift in where they put their ad dollars. And it seems to be happening faster and faster, it’s really picking up  momentum. It only takes a few drips to start melting a glacier, and we’re seeing that drip become a steady stream now.

Circling back to my lengthy take on Web 1.0 and Web 2.0, what we saw then was adoption. That’s all it was about, adoption, and going digital, surfing the Internet, exploring the web. Web 2.0 is about engaging, participating, collaborating, building, platforms. Local 1.0 is no different, it’s about adoption, going digital, getting online in an affordable way, and in a way that provides value. Local 2.0 will be about engaging and participating, and openness, and most importantly, mobile, the next and most inherently natural medium for local.

This is local 1.0. The tectonic plates are moving, and opportunities are opening up. The plates are moving faster now, and giant masses of land are revealing themselves above sea level. CitySquares is positioned to plant our flag. Move or die!

Five years from now I hope to look back on this blog and some of the various entries I’ve made on local search, some of the speculating I’ve done, and some of the research that I point to, and that I subscribe to in RSS daily, and remind myself how wild local 1.0 was. How I was a part of it, how CitySquares was a part of it.

Local 1.0 is here and now.

• DDC2007: The Future of Yellow Pages
• SMX Local & Mobile
• SES Local

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!

It’s also about the future. By that I mean that it’s about the future of our communities, my children’s future, the future of local commerce, of America, and the future of the Internet. That’s right – the Internet, that big monstrosity that’s you can’t touch, you can’t totally make sense of, that is so full of opportunity and promise that the opportunity for danger and destruction is just as frightening. The future of the Internet is about what’s right across the street from you. What’s local to you? Well, that’s the future of the Internet.

Humans need humans. Humans need interaction with each other. It’s not good enough to blog, to instant message, to SMS, to send pictures, share documents, post videos on YouTube, add another widget to your Myspace page, fly through the sky in Second Life. We, like much of the animal kingdom, are hardwired to need each other in an offline forum. The Internet, for the most part, does not help us feel more connected – it largely makes us feel more isolated. Call it existentialism, call it what you will. But these are my theories and these are my beliefs. The Internet is a great way to supplant the connections we lack in today’s society – a bandage, not a cure. We’re seeking something, as people, a greater understanding, enlightenment, a higher power maybe, human interaction, so many things. The Internet is a result of this, and will become more of an instrument for these puzzles just as much as praying is to some people, or just as the Hubble telescope or SETI is to other people.

I’ll stop myself there before I get too philosophical and ultimately keep myself awake tonight wondering if I articulated myself properly.

The funny coincidence is within a blog post that I stumbled upon yesterday. Here’s a small taste for you:

“Key to the development of a local online ad market is the identification of the local web, and this offers a remarkable opportunity for those willing to explore this territory today. In the not-too-distant future, everyone will have access to the local web, but this access is unavailable today, because the database hasn’t been created. It exists in bits and pieces, but no technology can replace the human research necessary to build the initial database. This is a task that will pay huge dividends to the one who creates it, market-by-market, and there’s no reason this can’t be done by a local media company.”

and

“The local web is where the web itself will find its real value propositions, and that’s enough to make a guy want to stick around for awhile.”

That’s enough for me. It does a great job of making the case better than I could’ve even after 5 more cups of coffee.

If you’re interested in local, community, the Internet, the future, advertising, all or one of the above, than I highly recommend you read this.

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

Ultimately I think this comes down to two major issues with the papers. And by papers I’m referring to the top dogs like The New York Times, and small community papers and TownOnline (here in New England). In fact, I had the opportunity to interact with an exec at TownOnline/Herald Interactive and there was a sort of arrogance there – like they’re so far ahead of the rest of us that we should be so lucky. And looking at them a year + later, nothing’s changed. So actually, let me make this 3 major issues:

1. Arrogance: Just through my experience with Herald Interactive/TownOnline, and even some indirect communications with The Boston Globe and Boston.com – there’s a very old-school, conservative mentality. I have a contact at a large IBank who deals with these folks and he and I talk often about the hard-headedness of these folks. I’ve been introduced to a few people at these papers and they just can’t be bothered. At the risk of sounding bitter (maybe I’m too late), I’ll stop there.
2. Stodgy: I think there’s a lack of innovative and forward thinking leadership at a lot of these companies. Folks, it’s 2007. If you’re a newspaper and you haven’t made a big Internet play yet – you’re in deep doo-doo. I commend the NYT for making some big big changes over the past year or so. I love what they’ve done and I find myself using those features and logging in more often every week. Great job NYT! Boston.com – wish I could say the same for you. I don’t think this has as much to do with #1 and #3 as much as it simply has to do with an old-school, stodgy, good ol’ boys club mentality.
3. Techno what? Yes, no doubt there is a lack of technological initiative and strategy. But you can’t expect a newspaper with the first and second characteristics to embrace technology, can you? I haven’t really seen any major paper embrace technology in a meaningful way with a few exceptions (NYT, WSJ). Those exceptions have not only embraced technology, but they’ve also integrated into their business model – they’ve made adjustments. And as time goes on, things seems to working out fairly well.

All of this circles back to why they haven’t made a significant local-search play. The reasons for me are obvious, but I’m not a newspaper industry expert – no really, I’m not. I’m glad, too. Because there’s a market for me and Citysquares.com that allows us to make a big move. Question is, how long will it take for them to make another adjustment? I’m not too concerned, but my antennas are definitely up and tuned in.