Boston And Silicon Valley: Three Years of Experience Later

Posted on May 20, 2013
Filed Under Critical Thinking |

When I moved Backupify to Boston in 2010, I did it because I thought it was a much better place than Silicon Valley. And I still love Boston tremendously. It’s a city of ideas. I have interests outside of technology, and the Boston is more diverse in its intellectual interests as a city than any place I have ever been. But over the past 3 years, I’ve traveled to the Valley 6-10 times a year each year. Over the past 3 years, I feel like I have better come to understand the differences between New England and Silicon Valley for startups, and I think it can be summed up in one sentence:

Nowhere else in the world is unconventional thinking as admired and encouraged as it is in Silicon Valley

I haven’t seen the statistics on this, but my guess is that Boston hits singles and doubles, on a percentage basis, much better than the Valley. The Valley, on the other hand, probably has more strikeouts, but also more home runs. As I’ve talked to more and more people about this, I’ve come up with a good example than illustrates the differences in thinking pretty well.

Say you wanted to build a Gmail competitor. You walked into the office of a VC and said, “Gmail is broken, I am building something better. I want to take out Gmail. Boston and Valley VCs would both say the same thing. They would say, “That’s crazy. Gmail has 200 million users.” But, they would mean very different things.

The Boston VCs would think “that’s crazy” as in “that’s stupid,” and they would think “Gmail has 200 million users” as proof that it’s a waste of time, you can’t do it, they already have too big of a hold on the market.

Valley VCs would think “that’s crazy” as in “it’s aggressive and unconventional, so yeah, we like it.” They would think “Gmail has 200 million users” means it is a worthy market to go after, not a waste of time.

Obviously, there are some West Coast style VCs in Boston, and some East Coast style VCs in Silicon Valley, but I’m talking about general attitudes. And it’s not just VCs, I think the same thing can be said of the talent pool in each place respectively. The talent in the Valley is more unconventional, which is both good and bad. But in the end, it’s the unconventional ideas that bring the mega home runs, which is why the world changing companies are in the Valley.


3 Responses to “Boston And Silicon Valley: Three Years of Experience Later”

  1. Keith Ringer on May 20th, 2013 2:52 am

    Rob, I think you nailed it. When are you heading left coast? Plutos’ salad with tri tip, garbanzo beans and blue cheese… It goes well with innovation.

  2. P Singh on May 20th, 2013 3:36 am

    I’m running both an unsexy business and one that I’d like to build here in Boston, so have been following your blog with interest. This post is decidedly a glum perspective on the landscape here. Do you see any hope on the horizon; for example when you or others like you start investing? If you’ve watched or read it, wasn’t Moneyball about how stringing together singles and doubles could actually be a winning strategy? (And don’t you think it could be unconventional now NOT to go to SV?)

  3. Smit Patel on May 20th, 2013 3:41 am

    I think the gmail example describes it perfectly.

    Both places have its pros and cons.

    At the end of the day, talented folks will succeed anywhere is what my thought process says.


  • About Rob

    Rob is co-founder of He likes value investing, the Rolling Stones, college basketball, artificial intelligence, economic history and people who think independently.