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! 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.