The Golden Age of the Boston Internet Entrepreneur

There are a couple classic archetypes of internet/software founders, including the genius college student cooking up something quirky but ultimately disruptive in his dorm room who launches his company straight out of undergrad. But the other archetype is a thirty-something entrepreneur who, taking his experience seeing the playbook of success at larger growing startups or even “established” companies, utilizes that domain and functional expertise as unique insight into founding a company. This latter persona is still hungry, but is able to really leverage that experience-set.

While a year ago there was much ado in the blogosphere about the peak/best age of an internet entrepreneur – whether it’s someone under 30 with fresh de novo thinking – there is some statistical support that the successful thirty-something entrepreneur is actually more prevalent. Anecdotally, you can point to examples here as well (Zenstrom / Skype, deWolfe My Space, Hoffman / LinkedIn, Williams / Twitter were all in their thirties). In reality, there is no “best” age to start a company, but rather different cohorts produce different profiles of entrepreneurs and resulting companies. (And at NextView Ventures, we’ve funded both young entrepreneurs out of college as well as veteran executives in their forties, along with a range in between.)

One historical challenge with the Boston entrepreneurial scene is that while we have a continually refreshing supply of the nation’s brightest coming out of our local prestigious educational institutions, for the better half of a decade in the 2000’s we were both losing people coming out of school, plus we had fewer of the second set of thirty-something internet entrepreneurs referenced above. Two years ago Jeff Bussgang lamented about “Lost Generation” of entrepreneurs which I think is especially acute here in Boston.

My own personal story fits in with this narrative. I was in my early 20’s just barely out of school when four of us (peers) started Sombasa Media (aka BargainDog) here in Boston beginning in 1998. We rode the bubble wave to a successful outcome in 2000, and after moving away for a few years which included a stint at business school, I returned back to Boston in 2004, and it felt like the web entrepreneurial community had almost entirely scattered after the crash.  Reactions when I told people I was an “internet entrepreneur” ranged from smirks to blank stares.

In only a few short years, the strong pillars of the local Internet scene, like Lycos & CMGI (+ affiliated companies), had fallen away and been rendered irrelevant.  Along with their demise came a dismissive attitude about most entrepreneurial web-related endeavors.  It surprises me how little this fact is talked about in Boston, but there was a vacuum left behind with these potential powerhouses withering away.   If you had a few ounces of entrepreneurial blood in the late 90’s, of course you started an internet company (for better or for worse). But from the middle of the last decade onward very few peers of mine were starting companies because they hadn’t had the opportunity gain that valuable experience like they would have had at Yahoo then Google on the west coast -or- they were dissuaded from negative experiences during the crash and a challenging atmosphere after. Instead, they had fled to other industries and those other geographies. My own motivations for starting the Web Innovators Group in 2005, and the reason I believe it took off so quickly, is that there were relatively few people in the community, but those who were all yearned to congregate and find a similar network of like-minded individuals.

Today the landscape is very different from 2004. First, there is an organized community net which is better (although certainly not perfect) at “catching” raw entrepreneurial talent out of the universities and keeping people here in their 20’s. Recent initiatives like Startup School are easy examples to cite, but there are numerous programs including the proliferation of networking events which have laid an infrastructure support to help keep the next Zuckerberg from slipping through the cracks. But second, we’ve also had a number of internet successes which have trained and developed people (e.g. TripAdvisor, Brightcove, Constant Contact, Wayfair) over the past few years where employees are beginning to roll out to start new ventures. And the larger imports (Microsoft, Google, eBay… recent challenges not withstanding) have now been established for a time that people have had at least a few years to formally train in internet software product development areas. And so that second cohort of thirty-something entrepreneurs is just now emerging as a solid group because there have been places for the internet skillset to develop. For example, it’s much more prevalent today in 2012 to have been a tactical internet marketer for the past five years whereas in in 2007 is just wasn’t. There is also now a third cohort, though still rare, of awesome people who have had entrepreneurial success experience during the 90’s boom now building truly transformative companies later in their careers who had moved away & returned, who eschewed a venture capital role after a brief stint, or who had been doing it all along. Plus, on top of it all, with accelerator programs we’re net importing kick-ass founders from all over the world.  But last of all, attitudes have changed – you CAN build a great internet company here in Boston, and we have a community which sincerely believes it.

So in Boston, it’s essentially taken a decade, but we’re finally overcoming the crater that the failed local internet giants left behind after the 90’s bubble. There are now three strong cohorts of internet entrepreneurs ripe with ideas & passion who are deliberate about staying here & building the center of the universe for emerging platforms. And that certainly wasn’t the case when I moved back here in 2004. With real clusters of strength in areas like mobile, marketing, and consumerized B2B SaaS – Boston is entering a golden age of internet entrepreneurs positioned for the future.


David Beisel

David Beisel is a co-founder and Partner at NextView Ventures. He has been focused on early stage Internet startups his entire career, both as an entrepreneur and venture capitalist. As an investor in the digital media space, David was most recently a Vice President at Venrock and previously a Principal at Masthead Venture Partners. Prior to becoming a venture capitalist, David co-founded Sombasa Media, an e-mail marketing company best known for its flagship product BargainDog. Sombasa was successfully acquired by About.com where David served as Vice President of Marketing. David holds an MBA from the Stanford Graduate School of Business and an AB in Economics, magna cum laude and Phi Beta Kappa, from Duke University. He also founded and leads the Boston Innovators Group, an organization which holds quarterly entrepreneur events drawing a thousand attendees.

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