My Experience at 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 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 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 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. 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! Another great software that I have found is the SalonTouch Studio Software, it has everything I need.
  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. Wink

Fond memories of

John Kelsey has a nice piece on The Kelsey Group blog about, 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. was a fantastic site back in the day. In the mid/late 90’s I used quite a bit. I used it to find music shows in Boston and Cambridge, to find restaurants, and so much more. I really think 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 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 I don’t think so. It was the Model T – the first of its kind.

Gadget Disease, Part II

Well folks, I said I wasn’t going to do it, but I did it. I did it and so far I’m not regretting it. In reference to my Gadget Disease post, I am, in fact, now a T-Mobile customer. After years and years of being a loyal customer of Verizon Wireless, and after years and years of shamelessly promoting them, I’ve jumped ship. I will confess that I feel like a mutineer. It’s like I told my barber of 20 years to go take a hike, and went to the salon down the street. That’s really what I feel like, especially with Verizon’s great commercials, superior CDMA network, EVDO, strong brand, good customer service, and cool brand versus T-Mobile’s rather unimpressive position in the US cellular market, their pink brand, sheek commercials with the lovely Catherine Zeta Jones, and their inferior EDGE network. Ah, but alas, I am now one of those guys – a ship jumper, a traitor, a pinko. And ya know what? I don’t care! I’m happy so far! It will take a few days for me to get over my shame and adjust to the new reality of my daily mobile life, but I’ll get by.

Here’s how it went down:

After my Gadget Disease post I saw Mike Orren’s comments and suddenly I thought – hey, there’s a guy who’s happy with is choice and is saving a bundle of Washingtons. That, my friends, was compelling. Upon further research and investigation, about 6 hours worth, I quickly deduced that Verizon is ridiculously expensive. But here’s the kicker: I called Verizon. Explained how long I’ve been a customer (umm… Bell Atlantic Mobile anyone? Circa 1997?). I told them how shocked I am at the competitions rates and selection of phones. I went on about a few other details that I shall forgo here, and their answer (twice) was “I’m sorry sir, I wish there was something we could do.” Now, keep this in mind too: this is a corporate account, with a few lines on it, not just me. So they basically told me I’m free to leave and they won’t try to stop me. Wow!

So, I did. After looking into T-Mobile’s packages and pricing, and going online to read what the masses had to say about EDGE, about the BlackBerry Pearl, etc etc, I contacted a local T-Mobile store, in Cambridge (at the Galleria Mall – ask for Ralph or Christina). Ralph spoke to me on the phone, and put up with my fast talking, my fumbling of plan configurations, and my many call backs. He was patient, kind, easy-going, and most of all – no b/s. He gave me the best possible price for our new account, and gave me an unbelievable deal on the phones. I was very very pleased. That evening Chris and I went there, and spent a good hour with Christina, who took very very good care of us.

Long story short, I’m now about 20 hours into my T-Mobile contract (as are Chris and Bob) and not only are we paying less with T-Mobile, but we’re paying less money per month for a whole bunch more! Unlimited this, unlimited that, MyFaves, great deal on the phones, no activation fees, a credit on our account, yada yada yada. Just a no-brainer!

Onto the Pearl – I’m thrilled. I can’t believe all the emotional abuse I put up with using Windows Mobile for so long. All three of us have the Pearl now, and we’re like kids on Halloween. I couldn’t be more pleased with the performance of the phone and the availability of software, information, tips, etc. However, two things I’m annoyed by right now:

  1. User Interface. I rather like the Windows Mobile UI. BlackBerry is nice… it’s lightweight – I like that a lot. But for messaging, the UI is a little clunky. Sort of like looking at lines of code or something. Takes getting used to, that’s for sure. Not too clean, at first anyway.
  2. Email syncing. This is, after all, BlackBerry’s thing isn’t it? Yes, well, it’s a piece of cake if you have BlackBerry Enterprise Server running. But come on! We’re a small company, we can’t shell out $1500 for that baby. We have Exchange, but we use that for mailbox redundancy and for basic calendar and contact sharing. We actually POP our emails into our Exchange mailbox. I like that approach. But without BES, you’re left with three options:
    1. Just use your BB to pop your email. Problem: Must have outlook closed, or not popping at the same time (sure sure, have Outlook leave mail on the server – no thanks.) Plus, I want emailed PUSHED to me, not popped. That’s the point!
    2. Use BlackBerry Desktop Redirector. Well, I would if I could – it won’t work for me. I’ve spent too much time reading forums and reading whitepapers and still can’t get it to work. Keeps saying “Disabled” and “Verifying forwarding address” Ay yay yay.
    3. Use Mail Connector. Got that working nicely. Very nicely. Got it going through the T-Mobile website (which, by the way, is amazingly sophisticated. Very impressed with It was working last night, then it stopped. I restart it and it works for a little bit, then stops.So, I arrived at the following solution:We use for our hosted email, for many reasons. Anyway, I just have a copy of each email forwarding to my blackberry email address. So, it comes to my Outlook InBox, and my BB. That’s fine. Works fine. Minor concerns about that, but so far, whatever – it’s doing just that.

Oh, and one last thing – EDGE? Highly under-rated. I’m quite impressed. Sure it’s only 144 kb/s, but ya know what? EVDO is very VERY fast – but what does it matter if you can’t use it? Any Windows Mobile phone I had, whether I was using IE or Opera Mini, it would either crash my phone, freeze it, or just take too damn long. The BlackBerry browser and Opera Mini work exceptionally well with the EDGE network. I’m both shocked and in awe!

All things considered – very pleased. A smart choice. Mike, if you read this – thank you!

All things considered, I’m happy with my choice. Laughing

Newspapers and Local Search – what’s wrong??

A validating little piece on The Praized Blog today and Don Dodge’s blog about the Local Search space and if/why newspapers get-it. I could not agree more with this, as some of my previous posts might indicate (in more or less words).

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 – 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! – 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. Surprised I’m glad, too. Because there’s a market for me and 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.

Gadget Disease

Thanks in part to this year’s annual CES and all the Apple iPhone hype, I’ve got the phone bug. I must I must get a new mobile phone and if I don’t get one now I’m going to suffocate. How can I keep functioning with my $500 Treo 700w? I simply cannot. I’m stuck in the dark ages. And with all the damn hype around this silly iPhone (pending Apple’s arrogant but unsurprising Cisco trademark infringement matters), and with the problems I’m having with my Treo, I simply must have a Blackberry Pearl. Problem is, Verizon doesn’t offer the Pearl yet and I’m not willing to switch providers.

So what’s going on here you ask? Aside from my neurotic must-have-new-gadget syndrome? Nothing. I’m simply neurotic and I must have a new gadget. I could just as easily be in the market for a new Luxury PC or this flat screen monitor, or an Infinity M. But at this very moment in time, I’m totally and utterly fed up with my Treo.

Ok, I’ll get totally real for a moment – it’s not that I hate my Treo, it’s just that I really dislike it. Ultimately, I’m really sick and tired of Microsoft’s mobile software. I first experienced Microsoft on a mobile device back in like 1997 when I had my first iPaq. At the time it was a really great calculator on steroids and it displayed Word documents, Excel spreadsheets on a really tiny screen which was like, so cool. But then I said to myself, holy moly – this will be integrated with a phone some day! Well, cell phones were still the size of tug boats then, but sure enough I soon had a … a SMARTPHONE. And WOW was it cool. Yes, I could finally make calls AND sync my calendar and Outlook contacts. But then I said, wait, I want to surf the web too. Oh, Verizon offers that? Oh I gotta have that. So $40/month later and I had my smartphone browser surfing Verizon’s limited selection of websites (cuz others would not work on this device – but at least I could check Sox scores in the middle of a wedding). Money very well spent of course. Well, as time went on, and EVDO came to Boston, and smartphones kept coming, and Microsoft kept updating their UI, I kept upgrading. I last had a Samsung i730 – I hated it with a passion. What a clunky piece of hardware. Who needs a phone that has a processor that rivals some small laptops, with an expanding keyboard that’s more like a kitchen drawer in your pocket? You look like you have a brick in your pocket with this ridiculous monster! So, 6 months later I had the Treo. My first Palm in several years, and I loved it – but it runs Windows Mobile. Like all my other Windows Mobile devices, it freezes at least once per day, and right when I need it most – like when I need to answer a call. Or like, when I need to make a call. Or when I’m driving and need to read an email. There’s nothing like having to pull the back cover off this sexy looking, but poor performing, device, pull out it’s, eh hem, stylus, and insert it into the, um, reset button. Yes, a hard reset is what it needs, often in fact. Oh but I can write Word documents on it! I can take pictures! Review Excel files! Watch videos! I can surf the web – wait no, that freezes my phone too. I sound like this device is evil, it’s not. It’s much much better than the Samsung, but still – what’s with all these bugs man? I mean come on! Every single time I have to reset this baby I curse Microsoft. Finally – I’ve had it. I’m done with it. I WANT THE PEARL AND I WANT IT NOW! Because I can do all those things without the stress – right? I will be able to do all those things without the stress right? And it’s a cool device, right? (cool people should not answer that)

Ah, but alas, I will have to wait. Apparently Verizon is not talking about the Pearl, but rumors say it’ll be just a little while longer (sorry, no link – took me an hour just find something online that gave me hope). And when that happens, I’ll find something else to fall in love with. But if the Pearl was available today in CDMA, I’d buy it right this second. I would not even be here typing – I’d be on my couch reading every word of fine print in the various documents and wondering why it took me so long to become enlightened and becoming amazed by the backlight settings that are some how better than any other backlight I’ve ever seen. Then I’d be customizing my theme, and wallpaper, and then I’d be looking for new ways to enhance the device like buying software I don’t need and will never really use, and installing blackjack or tetris, and then I’ll screw the device up and have to reset it and start all over. Ah, you see – but now I’ve learned it’s weaknesses. AH HAH! It was strategy! I learned, now I start anew and better – and soon I will be in control of my life again.

But, now I must wait, in frustration and sadness, while Verizon takes it’s time figuring out how best to release the Pearl – and surely with some limitations that will leave me salivating for the next new phone that can tell me when my milk is expiring (cuz my fridge can’t yet). Hey, it’s nice having a new toy to look forward to.

Lastly, mark my words right now friends and observers: I will never – NEVER – buy the iPhone. I won’t, I simply won’t. Why? So I can experience the proprietary purgatory that is Apple, Inc.? (watch, they’ll probably sue me now for saying disparaging things about them. But hey, it’s not like I’m creating an iPhone theme for my Treo or something! I mean sheesh!)

Ok, I’m done. Maybe I can find some cool accessories while I wait for Verizon.

Local Merchants and Adapting to Change

A very interesting post by John Kelsey at The Kelsey Group. Very outspoken and candid reality check for small businesses, and I happen to think he’s right on the money here. I’m reminded of a conversation I had a couple weeks ago with a gentleman in New Hampshire, who was referred to me by a mutual contact. This gentleman was shopping for a Christmas gift for his wife and was at a locally owned jewelry store in the seacoast region of NH. He went in looking for a watch and didn’t quite find what he was looking for.
<!–break–> He still purchased a watch anyway, because it was a matter of convenience. He had an idea, which he shared with me, about an inventory management and distribution system for which a business, such as this jewelry store, could access their distributors’ inventory and special order items. It was more complex than that, but that’s the gist of it. He was aware of my involvement with Citysquares and wanted my opinion on whether or not he thought there was a market for this sort of thing. I explained that while I thought there was certainly a market for it, the reality is that getting local merchants to conform to the requirements of the new technology is a tough sell. Local merchants have their own ways and methods for running their business. Surely there are some standards, like Quickbooks, or Peachtree, and some standard POS and inventory systems, but at the end of the day, they use what’s easiest and most convenient. Asking a local merchant to adapt to the pace of technology and changes around them is like asking a third world nation to adopt environmentalism – it’s a stretch. Unless you can really point out the benefits and make the proposition that they can justify a quick and measurable ROI, it’s really an uphill battle. Unless it directly affects their bottom line, they will resist change. So while I agree with John’s reality check, reality is relative. There are movements all across our country, to prevent the invasion of big box retailers and the homogenization of our communities. Ones that comes to mind is Local First and BALLE. These are not fleeting ideas run by hippies, these are serious and business minded individuals who are doing it, and doing it well (to quote LL Cool J).

Creating the next Google?

Another interesting little piece in the NY Times. So they’re going to go head to head against Google eh? OK, even with the punches Google has been taking lately I think going toe to toe with them is futile. It’s like the Swiss Army going up against the US Army – it’s laughable. However, after the laughter, one must also acknowledge the balls these companies have going up against Google. I admire it. Google, like Microsoft and like IBM, cannot maintain it’s position at the top forever – it’s not natural and it’s not realistic to think that any company can be #1 for ever (on the Internet anyway) – other industries is a different story (e.g., GE, Wal-Mart). So at some point, someone will take Google down from the perch, even if briefly. I don’t see it happening for many years. And when it does happen, I don’t think search will be like it is today (text based, search engine websites, etc). The Internet is still in its infancy, or it’s a toddler, I’m not sure. But at 13 years old (out of the womb), it’s still very immature. I just think that any company that really wants to compete with Google, and their visions of artificial intelligence better step WAY out of the box, think WAY long term, and start to plant those seeds. Google has a big leg up on the competition.

Google – love ’em or hate ’em – they’re like the moon, pulling and pushing the tides of the Internet and they have the power, and will continue to have the power, to shape what tomorrow’s Internet has to offer.

Hyper-Local Going Mainstream

I’m a loyal New York Times reader, both online but also their Sunday paper. It shows up on my doorstep every Sunday morning and I often look forward to sitting in the kitchen and reading the paper, while my wife makes our Sunday breakfast. Long after we’ve eaten I’m still sitting at the kitchen island sipping a mug of cooling coffee (freshly pressed) and reading the Times.

The NY Times had a notable little piece in their Sunday edition this weekend (12/31/06), titled Seeking to Cash In On the ‘Hyperlocal’. While Manly refers to “Hyperlocal” as all news things that are hyperlocal, I can’t help but smile knowing that the term is getting more mainstream attention. Lorne Manly refers to the Rob Curley breed of hyperlocal: news oriented hyperlocal content (whether user generated or editorial). This model of hyperlocal, as the article points out, is what Backfence is doing. Another example of this is what Mike Orren is doing at Pegasus News in Texas. All of these are hyperlocal news based sites. Rob Curley’s done a heck of job in some of his markets (notably, Naples and Bonita Daily News, and the Lawrence Journal before he went to the Washington Post), and in doing so helping to shape what has has become “hyperlocal.” I look forward to a fusion of hyperlocal journalism and local search in the coming months and years.