A break in the east coast rain
I think we're just about done imitating Portland with respect to a rainy season (omg 3 days of rain). The reason I bring up a small city in the upper north west is that they have a fantastic tech and startup community. If a city Portland's size (100k ish) can foster many hacker and tech conferences, why can't other areas follow their lead?
There's over 3 million people on Long Island although the people density ramps up as you get closer to Manhattan. We've got a handful of good universities (I can vouch for Stony Brook), and a number of tech companies, although not nearly enough dedicated to web development. So why is there absolutely no startup culture within 50 miles of my house?
I'm talking nothing, none, nada, zilch. There is it least one incubator that charges lower rent and provides some business guidance, but high value web tech companies aren't exactly like eggs in need of a heat lamp. I can't deny Paul Graham (YC) and Brad Feld (TS) have fostered some fantastic programs and given solid advice to would be businesses. But their secret sauce isn't them. It's the density and commingling of tech startups that attracts investors. The problem on Long Island is that most folks don't even consider the remote possibility of building a tech startup.
The first problem is Manhattan. It sucks up anyone with a startup bone in their body. Don't get me wrong I love the Big Apple, all my favorite tech/business meetups are there. But I'm a big fan of natural surroundings, peace and quiet. Silence in Manhattan is a rarity and grass is something you see only in park visits.
The second issue is no big super tech companies. We have Computer Associates instead of companies like Google, Apple, and Facebook. The churn of talented engineers that are fed up with management hierarchies organically feeds new startups which have a flat organization. If you can't challenge your CEO to a ping pong match your org chart sucks.
A lack of successful tech entrepreneurs also is a hit against the area. Successful founder exits translates into tech savvy angel investors and advisors which fuels follow on startup generations.
We do have at least one solid university (Stony Brook!), but I'm pretty sure most grads from Stony Brook aren't considering startups and business building as a way of life. It wasn't something that came up too often. I do remember one group of friends that started a dial up Internet service company.