I was born and raised in the Boston area so the most recent dust up about Boston vs Silicon Valley has me comparing it to Beantown’s previous long-lived case of self-flagellation - The Curse of the Bambino.
For the Red Sox it was the trading of Babe Ruth, while for Boston web startups, it was the loss of Zuckerberg and Facebook to Palo Alto. That sin has cast loads of self-doubt on whether Boston can ever truly compete, often with those in the Boston tech scene being the most critical of its shortcomings. Like Red Sox Nation living under The Curse, those in the Boston startup community can often feel like losers despite being in the 2nd (or perhaps 3rd) best market to start a company. Compare this to the confidence of those from Boulder who have the Moneyball-era Athletics’ knowledge that they are punching above their weight for a city of 100,000.
The good news is that we’re no longer in our Mo Vaughn / Mike Greenwell era of frequent disappointments. During my five years around the Boston startup community I’ve seen things improve considerably to where I think we’re assembling our “2004” roster:
- Like David Ortiz, HubSpot is swinging for the fences with their recent $32M raise, and Dharmesh "Big Papi" Shah has shown how to remain a hacker while dominating marketing and growing a company filled with talented folks.
- Long-time leaders like Bill Warner have been the squad's Jason Varitek, teaching younger teammates how the game should be played.
- SCVNGR and WHERE resemble a certain Manny Ramírez - not always well-understood but looking to hit it deep. SCVNGR's Seth Priebatsch keynoting SXSW and building LevelUp to challenge Groupon and LivingSocial has a certain air of "Manny Being Manny" to it.
- Companies like Gemvara, CSN Stores and Viximo remain modest while consistently putting up numbers over .300 like my favorite unsung hero, Bill Mueller.
- Folks like Greenhorn's Jason Evanish, Victoria Song and the DartBoston crew have that Kevin Millar "why not us?" attitude that sparks others to do more. (Just avoid the Bronson Arroyo cornrows, please.)
- Lean startup devotees Performable and Blueleaf have the iteration speed of bearded Johnny Damon.
- The gaming startup scene is showing Curt Schilling resilience, despite his own 38 Studio moving across the border to Rhode Island. While a tough year for some companies and frustrations at not extending a tax credit to game makers, there is increased focus on gaming companies and PAX East in Boston was the largest PAX to date.
- More smart, strategic Theo Epstein brains like Eric Paley at Founder Collective, Lee Hower at NextView, and Antonio Rodriquez. And I can only imagine investors like Bijan Sabet and David Skok must have a John Henry-sized yacht to sail while making deals.
- Finally, the pipeline of talent coming through TechStars and MassChallenge in companies like Localytics, SocialSci and Locately is producing Jacoby Ellsbury-esque up-and-coming stars.
This is not to imply there aren’t real improvements to be made — there most definitely are — but the trend line is heading in the right direction, even if we lose a Nomar along the way. We’ll never change Boston’s weather and many will remain immune to the areas charms that include bright folks galore, (entrepreneur-friendly) health care reform, gay marriage and the nation’s best sports city. So let’s take a lesson from the “Idiots of 2004” to set aside all that baggage and get ready to play ball.
 Yes, Ellsbury didn't join Pawtucket until 2007. It's just an (perhaps over-extended) analogy.