Events and Networking for Boston Startups

It’s been over two years since we discovered WebInno and were subsequently invited by David Beisel to be a sidedish. Among other notable Boston area events, WebInno was probably the most exciting for us, and it really gave us the shot in the arm that we needed. We also met some fantastic people that evening, many of whom we stay in close contact with. In fact, we met one of our advisory board members at that first WebInno. Each time I attend a WebInno, I’m not only shocked by the spike in attendees each event seems to have but also by the genuinely good vibe in the room that lasts for hours.

My point here is that as a startup company, and as an untested business seeking an identity and a place in the Boston entrepreneurial and startup scene, WebInno was really just one of many pivotal networking events for us. As this blog continues to be about entrepreneurship, and my perspective from the trenches, I don’t want to forget about these events and opportunities. Furthermore, I really encourage other entrepreneurs to be sure they get out there – hit the streets, attend events, network, don’t be shy. It’s like anything, once you get some momentum and get into a rhythm it just gets easier.

Here are some events that I’ve either attended or would like to attend in the Boston area:

  • WebInno – Cambridge, MA, about once every 3 months or so. Well worth it! And if you’re in the Internet space, check with David to see if you can a shot at a side dish or main dish. David’s very accommodating and open minded.
  • MIT Enterprise Forum – Cambridge, MA. Hey, it’s MIT man, you know it’s gonna be interesting! I’ve been a member of the MIT Enterprise Forum for about two years now. While not all their events interest me, specifically the bio-tech stuff, they do host many very helpful and relevant events and networking opportunities. From big, globally broadcasted panels on angel investing and venture funding, to small networking opportunities where David Weinberger shares his perspective on the digital world, MIT Enterprise Forum is well worth your attention.
  • MIT Entrepreneurship Center – Cambridge, MA. Are you an entrepreneur? Doesn’t really matter what industry you’re in – go to these events! Get involved! There’s a ton of value to be gained at this event. If you’re in the Boston area – don’t be a schmuck, take advantage of all the MIT has to offer!
  • The Capital Network – Waltham, MA. An organization for entrepreneurs seeking funding. I had the honor of being on one of their recent panels and I thoroughly enjoyed myself. TCN offers some really powerful resources for entrepreneurs, and they really take their time to make sure you’re absorbing all that you can. It’s very much a dialogue at TCN.
  • TechTuesday – An event hosted by the Mass Technology Leadership Council and growing in strength and numbers.

Here’s a bunch more (write-ups courtesy of Don Dodge, thanks Don!):

New England Angel Capital Conference – The Angel Investor groups of greater Boston meet once a quarter to review their best companies. Each group nominates companies to present. They are all looking for a round of funding that is bigger than any one Angel Group can handle. This meeting lets all the groups get a look at promising companies and pool their investment dollars.

Entrepreneurial Team Building – a panel of entrepreneurs that have built companies from the ground up and know the ins and outs of building great teams. What really makes a team come together? How can you be sure that you are bringing in the right folks? Who should be hired first, second, next? We’ll talk about teams at the senior management level and at the BOD level.

Entrepreneurial Series – Plain English Term Sheets – This is a webinar for startup entrepreneurs who want to understand the details of financing term sheets. What to ask for…and what to avoid.

MITX – Mass Innovation & Technology Exchange have lots of great events for technology based startups. The next session is “Building Social Applications and Widgets“.

The 128 Innovation Capital Group – The regular meetings are held on the second Thursday of every month at the Best Western Hotel on Totten Pond Road in Waltham. Every month an investor provides our formal program. After Q&A, our speaker generally remains to speak with audience members, one on one. After the meeting, a roster with the contact information of all attendees is made available to those who came to the meeting.

Nantucket Conference – The 2008 Nantucket Conference audience will consist of approximately 150 of New England’s top entrepreneurs, investors, and tech executives. Rather than sitting through a series of speeches and PowerPoint presentations, the audience will be engaged in a dialogue – and sometimes a heated debate – with Conference presenters.

Get out there! Spring is here, so you’re out of excuses! Part 1

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

As I mentioned in a previous post, I had been a loyal 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 and they’d become loyal users. Eventually was gone, and replaced by Citysearch. I was never able to get the same enjoyment from Citysearch. 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 I worked at 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,, 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 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 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 Laughing). I knew there was at least one barbershop in Davis Square, but it was 7am – were they open? Yes – the same problem folks. The phone book was no help to me because I didn’t know the name of the barber shop I was looking for. I only knew it was on Highland Ave. But what number Highland Ave? Was it 16 Highland Ave or 1600 Highland Ave? Thankfully I wasn’t dealing with a violent stomach illness – only a massacred hairdo. I knew I’d survive this. So I put a hat on, and walked into the square. Guess what? The barber shop was closed. So I went and got a coffee, and soon had a repaired hairdo. The barber had a good laugh.

On Sunday, August 14th, my wife and I were talking, once again, about just how frustrating it was to find any truly local information about the businesses in our neighborhood. What is wrong with the world!? Why is this so difficult? And there it was – square between the eyes – I’m going to do this. Finally. I’m going to create this! No more 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 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: Nah, that’s gone. Nah, that’s gone. Countless others. Ali said, “” 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 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 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 – 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 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 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!

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