Over the last three weeks I’ve had numerous people ask me how my trip to Boston has been going. For a while I corrected them and said “I’m mostly in Cambridge” but gave up. Tonight, after hanging out at the TechStars Boston Mentor evening and program kickoff, I got into a long discussion with a Bill Warner and Ken Zolot about Cambridge, Boston, and startup communities. At some point in the conversation I blurted out “I have no idea why we call this program TechStars Boston instead of TechStars Cambridge.” And then something that I thought was important dawned on me.

My entire entrepreneurial view of “Boston” is centered around Cambridge. I’ve been here for two of the last three weeks (I spent four days in New York). I’m staying in a hotel in Kendall Square across from Google and next to MIT. I’ve spent my days walking to meetings at MIT, Kendall Square, Tech Square, Central Square, and East Cambridge including what I refer to as “the old Lotus building”. I’ve had all of my meals in Kendall Square or Central Square. Other than running, I’ve only been physically in Boston four times – first when I arrived at the airport, then when I took the train to New York, then when I returned on the train from New York, and finally when I spent the morning at Fidelity’s FCAT offices at Summer Street.

Now, I know there is plenty of startup activity in Boston. My old neighborhood near Fort Point Channel (I used to live on Sleeper Street in a condo at Dockside Place) is bustling with startup activity. There’s plenty of stuff on 128 and 495. There’s are other entrepreneurs tucked around the city. But that’s not the interesting story, at least in my mind.

The few square miles in Cambridge around MIT is the white hot center of startup activity in the region. One of my basic principles of startup communities is the need for what I call entrepreneurial population density (EPD) which I calculate as the total number of entrepreneurs and employees of entrepreneurial companies divided by the total number of all employees in a region. Then an even more powerful metric is entrepreneurial density, which is EPD / size of region. A large EPD in a small physical region wins.

Part of the magic of Boulder is the entrepreneurial density of the place. And as I wander from meeting to meeting in Cambridge, running into people on the street who I know, or who I met with the day before, or I who I want to know, reminds me of the dynamic in Boulder. For example, I ran into Matt Cutler on my way to Rich Levandov’s office and we walked over together. I bumped into the StartLabs organizers when going to a meeting with Will Crawford. I saw Joe Chung while hanging around StartLabs. I saw 50+ mentors who I knew last night at TechStars and expect to see more today when I’m there. While having breakfast with Michael Schrage at the Cambridge Marriott Joost Bonsen came over and said hello. At Dogpatch meeting with Yesware I saw Dave Greenstein and gave him a hug for his new kid. And the list of moments like this, which happened with 10 square blocks, go on and on. But when I hop on the red line and travel to South Station, the magic disperses.

I remember when the Boston VC community moved from downtown Boston to Waltham. I understood it was an effort to create a “Sand Hill Road” like venture community but the big miss was that an MIT student couldn’t hop on a bike and ride to Waltham like a Stanford student could with Sand Hill Road. And it’s no surprise that downtown Palo Alto, which is even closer to Stanford, is an attractive place for VCs to hang out. The snarky message when the VCs moved to Waltham was that they wanted to be close to their fancy houses and their private golf clubs and the entrepreneurs could come to them. It’s no surprise that many of these firms have relocated to Cambridge, recognizing that they should be in the middle of the entrepreneurial energy.

I’d suggest to the Cambridge and Boston startup communities that they should think of themselves as two separate but related communities. Even within Boston, it seems like there are different startup communities in downtown, 125, and even 495. I think that thinking of it “Boston” is a mistake.

In my world view, the entrepreneurs drive the startup community. Focus on entrepreneurial population density and entrepreneurial density – and make sure your geographic region is small. Over time, linking the critical mass together in a larger region (e.g. Silicon Valley or Boston) is fine, but the real power comes from the startup communities with the largest EPD in small physical regions which are big enough to have critical mass.

If you want to go to TechStars for a Day in Boston, today is the last day to apply for the Boston program early application deadline. If you haven’t heard of TechStars for a Day, it’s a one day event that immerses you in the TechStars program, exposes you to the mentors, and increases your visibility with the selection committee. Why wouldn’t you do this? I have no clue.

If you are contemplating applying to Techstars Boston, stop procrastinating and apply now. If you are curious about how some of the TechStars Boston class of 2011 have done, take a look at the post titled 2011 Funding: Boston. And yes, I plan to be in Boston for the second half of January so I’ll be at the first few days of the program for everyone who gets in.

I’ve been spending some time with the current TechStars Boston class. This feels to me like the strongest class we’ve had in Boston so far and might be the one of the strongest TechStars classes overall. This class of companies in Boston is thinking big and is very diverse.

It’s been incredibly energizing watching each of the four TechStars cities (Boulder, NYC, Seattle, and Boston) up their game every single year. In Boston in particular, Katie Rae has done a great job engaging many great new mentors. I was lucky enough to have the chance to meet many of them on my last trip to Boston, and they all seemed very excited to be involved. They were feeding off of the energy of the companies in the program, just as it should be.

If you’re an angel investor or would like to become one, there’s a great two-for-one coming in Boston soon. June 15th is TechStars Demo Day, where the new crop of companies there will show their stuff for the first time in front of several hundred investors. If you’re an angel investor or a VC and you’d like an invitation, just drop TechStars a note. If you’ve never been to a TechStars Demo Day event before, you’re really missing out on something special. The day before, on June 14, Jon Pierce has put together a great event called Angel Boot Camp where those interested in learning more about angel investing can spend the day learning from those who do it well. It’s a great opportunity to learn and then see some great new TechStars companies the next day as well. Oh, and just in case you want to be really cool, don’t miss Coolio at the TechStars after-party on June 15th.

If I’ve learned one thing in my life, it’s that nothing is static.

Periodically the meme surfaces that “the only place you can create a great software / Internet company is in the bay area.” While I think the bay area is a special place, anyone that knows me knows that I strongly believe there are several great entrepreneurial communities throughout the US and the potential for many more.

Boston has always been a great entrepreneurial community. Sure – it’s had it’s ups and downs, but when I lived here from 1983 to 1995 the entrepreneurial vector was awesome. I started my first company (Feld Technologies) here in 1987 and made my first angel investment (NetGenesis) here in 1994.

When TechStars opened a Boston program in 2009 there was definitely new energy around the software / Internet startup scene in Boston and TechStars was excited to be part of. When I say “Boston”, I actually mean “Boston/Cambridge” where the center of mass is really near MIT in Cambridge. The venture capital community has finally realized this (again) and much of the physical location of the VCs is shifting to the Cambridge / Kendall Square area with a little in Harvard Square (a 10 minute cab or train ride from Kendall Square.)

I spent the day at TechStars Boston yesterday meeting with all of the TechStars Boston 2011 companies. They are halfway through the program and are stunning. Three months ago I was super psyched about the quality of the TechStars NY 2011 companies as they were halfway through the program. The Boston program, under the leadership of Katie Rae, has taken it up another notch!

Last night at dinner I met a bunch of the TechStars Boston mentors. Katie has recruited some folks I’ve never met before and I asked her to put together a dinner with the people I didn’t know. It was just awesome – super food at Evoo, great conversation, and really impressive people. Tonight we have a TechStars Boston mentor happy hour so I’ll get to see a bunch of old friends and the rest of the TechStars Boston mentors.

At the end of dinner, Matt Lauzon, the founder/CEO of Gemvara, told me about this thing he and some friends had created called #RubyRiot. It’s a “pay-it-forward” event where everyone that comes asks for an introduction to one person (anyone on the planet) and everyone in attendance works together to make the introduction happen. Matt asked me if I’d sponsor the event – Fred Destin piled on and said he’d put up $1k if I did, then Reed Sturtevant did also, and Gus Weber from Dogpatch finished us off. I’m an easy mark so I jumped in the boat.

As I walked back to my hotel, I was buzzing from the day. I believe to my core that the entrepreneurs create and sustain entrepreneurial communities. Everyone else, including VC’s like me, are participants. And it’s just awesome to see the next generation of Internet entrepreneurs reignite the fire in Boston (well – Cambridge) and drag the last generation back into it.

The TechStars Boston application deadline is 1/31/11.  However, the early application deadline is actually 1/13/11 – anyone that applies by this date is eligible to come to TechStars for a Day in Boston on 1/19/2011.

Katie Rae, the new TechStars Managing Director is doing an awesome job.  I just got a note that we’ve already gotten more applications this year than we had last year.  Even more excitingly, they are covering a wide range of companies – some deep tech, social media, health care informatics, robotics, and ecommerce.

Boston has always had a wide range of early stage companies with unique characteristics, most notably robotics and network and system layer software, so it’s great to entrepreneurs from these segments show up.  We’ve also got some fun surprises on new mentors for 2011 in Boston that match up with these segments that we’ll be announcing soon.

So – don’t wait – apply to TechStars Boston now!  TechStars Year 3 in Boston is shaping up to be the best yet.

Jon Pierce of BetaHouse has decided to organize an Angel Boot Camp in Boston on June 1st. The idea is that anyone interested in learning more about how to get started with angel investing can attend and learn from some people who’ve been there and done that.

David Cohen at TechStars wrote about why he thinks it’s important.  Jon Pierce also wrote about why he’s doing Angel Boot Camp as well as listing some of Boston’s Best Angel Investors.

While June 1 is still several months away, sign up and put Angel Boot Camp on your calendar now.

My long time friend Warren Katz pointed me out to an event on March 3, 2010 called EO Boston Accelerator Shark Bowl 2010.  It’s a competition for entrepreneurs under 40 with businesses between $100k / year and $1m / year in revenue.  You present to a group of judges including Warren (MAK Technologies), Rich Farrell (Full Armor), Clark Waterfall (Boston Search Group), and Michael Hackel (DiningIN) who are all EO Boston members.

In 1993 I was the founder of the Young Entrepreneurs Organization Boston Chapter and member #1.  My forum group, “Forum Group 1” is apparently still meeting monthly.  And while YEO changed its name to EO, my friend Warren who has been a member from the very beginning tells me the group is still going very strong (the stats look like 88 members with total sales of $427m and 2,231 employees across all of the companies.)

If you fit the qualifications, I’d encourage you to participate.  It’s free, you’ll get some great practice and advice, and meet a bunch of new entrepreneurial peers.  To participate, you must register and to present you must sent your presentation to Caryn Saitz by March 1st. 

Go Boston (and Cambridge) – you are making me proud these days!

Scott Kirsner had a fun article in Boston.com today titled The Red Line Tour of Innovation in Boston. Several of the stops were regularly hang outs of mine between 1983 and 1995 most notably #10 (Miracle of Science) and #11 (Toscanini’s) but also including #5 (MIT Media Lab), #6 (Muddy Charles Pub), #7 (MIT Lobby 7), and #8 (Central Square and the Necco Factory – back when they made Necco wafers.)

I lived at ADP at 351 Massachusetts Avenue for four years as an undergraduate at MIT.  It was the first frat I went to when the freshman picnic ended (Mark Dodson grabbed me, shoved me in a white van, and said “you are coming with me.”)  I stayed the first night and never left.  Yes – it was a fraternity.

But we were also nerds.  There was something in the water and a lot of companies were created.  Scott got a few of them such as Colin Angle of iRobot, Jeet Singh and Joe Chung of ATG, and Frank van Mierlo of Bluefin Robotics, but I thought I’d add a few more.  While the founders of Harmonix (the guys that brought us Rock Band and Guitar Hero) came from the Media Lab, one of them (Eran Egozy) also lived at ADP.  As did my first business partner Dave Jilk, who is now CEO of Standing Cloud.  And two of the founders of Oblong – John Underkoffler and Kevin Parent.  Let’s not forget two well known VCs – Sameer Gandhi (Accel) and Mark Siegel (Menlo).  Oh – and Carl Dietrich’s flying car from Terrafugia.  We also lived next door (WILG – 355 Mass Ave) to some other impressive entrepreneurs including Megan Smith (Google and PlanetOut).  There have been plenty of others through the years – these are just the ones I can remember off the top of my head.  If you should be on the ADP entrepreneur list, please comment on this blog and add your name for posterity (and Google searches).

My first company (Feld Technologies) used 351 Massachusetts Avenue, Cambridge, MA  02139 as my office address for the first few years of its life (I officially started the company as a sophomore, although my partner Dave Jilk joined me shortly after I got my undergraduate degree.)  But Feld Technologies wasn’t the first company I started at 351 Massachusetts Avenue – that honor went to Martingale Software and my partners Dave Jilk, Sameer Gandhi, Andy Mina, and Jeff Pierick.  We raised $10k, bought a Lisa and a Compaq luggable, earned about $7k, and eventually folded the company and sent the $7k back to our investors.

During the four years I lived there and the two years I had an office at 875 Main Street, I ate an enormous amount of ice cream at Toscanini’s. To this day, Cocoa Pudding with chocolate fudge syrup on top rates as the best ice cream choice I’ve ever had on planet Earth.

One fall, after Feld Technologies had moved to Boston, we hired a recent graduate from Brown named Jonathan Lutes.  While interviewing him I asked what he had done over the summer.  He mumbled something like “screwed around a lot and built a bar called Miracle of Science with my brother Eric.”  Yup – same bar – this was 1990-ish – and it was at 321 Massachusetts Avenue.

Sometimes I actually miss the smell of Necco wafers in the morning.  It smells like ADP.

Last week while I was off the grid for my Q1 vacation, TechStars announced that we are doing a Boston program this summer.  Applications for both the Boston and the Boulder programs are open until March 21, 2009 at 11:59:59 PM MDT, but apply before 3/1/09 and be eligible to attend TechStars for a Day.

We launched the original TechStars program in January 2007.  We’ve now run TechStars in Boulder for two years and have had a dynamite time, helped create some super companies (we’ve had 20 companies go through the program, 2 have been profitably acquired, 2 are profitable, and 12 have been funded), and have been able to contribute meaningfully to the Boulder entrepreneurial scene.

In October, I spent a few days in Boston with Amy.  Among other things, I arranged a “nerd dinner” for some of my old Boston friends, including Shawn Broderick, Warren Katz, Colin Angle, Eran Egozy, and Steve Munroe.  While I have regular contact with each of them, they hadn’t been together in a gang for a while so we enjoyed a rambunctious meal at Sel de la Terre (thanks Warren for dinner) and ended up talking about entrepreneurship in Boston for a while.  There was a lot of discussion about how to energize the community more, what we had been doing in Boulder, and who was doing what to whom.  As part of the discussion, Eran told me I had to get together with Bill Warner, who had been thinking of some of the same things.

Coincidentally I’d been connected with Bill a few weeks earlier by David Cohen.  Bill was considering investing in EventVue (one of the TechStars 2007 companies), was interested in talking more about it, TechStars, and Boston.  We had lunch scheduled for the next day.  I’d never met Bill, but I knew of him from MIT and his experience as the founder of Avid and Wildfire, and had seen him speak about his experiences (I think at an MIT Enterprise Forum event) when I was living in Boston.

We had an awesome lunch and hit it off immediately.  Bill totally got TechStars and our mentor driven approach and said, in short “we’ve got to do this in Boston.”  A logical next step was to have Bill come out to Boulder, spend a day really immersed in things with David, and figure out if it made sense.  We did this and the three of us got more excited about the idea of doing TechStars in Boston, but realized we needed to find “a David” to run things on a daily basis.

We made our list of potential David’s, checked it twice, and started calling.  Shawn Broderick was at the top of the list.  I’ve known and worked with Shawn since 1988 – he was the third employee at Feld Technologies, I was the lead angel investor in Genetic Anomalies which had a very successful acquisition by THQ, and am an investor in TrustPlus.  Shawn was a perfect fit, spent time with David in Boulder, and voila, we decided to do TechStars Boston.

Wade Roush at Xconomy Boston has a thorough interview up with David Cohen titled TechStars “Entrepreneurship Boot Camp” Comes to Boston: An Interview with Co-founder David Cohen that goes deeper in to the why and how.  Shawn has hit the ground running and we are totally psyched with how the Boston program is coming together.

Having spent 1983 to 1995 in Boston, this is a wonderful “going full circle moment” for me.  I’m planning on spending some chunks of time in Boston this summer both with our investments (we’ve got two in Boston), TechStars, MIT, and old friends.  Bill – thanks for being the spark that got this started!