2010 Startup Moves from Boston to San Francisco Offer Insights to the Perennial Coast vs. Coast Debate

The debate over the merits of Boston and the San Francisco Bay Area as startup hubs isn’t a new one, but looking back over 2010 has given us new food for thought on the subject. At least four Boston-area startups packed their bags for Silicon Valley, working on technology related to errand exchanging, used clothing swaps, person-to-person car sharing, and e-mail organization.

The startups were attracted by San Francisco’s vibrant community of related companies, a friendly environment for business, investors willing to take a risk, or a mix of all three. “Companies have always moved to SF now and then,” says Boston-based angel investor Roy Rodenstein. “But I think it’s a reminder that, as far as we have come in making Boston’s scene more vibrant, inviting to new entrepreneurs, [becoming] richer in financing options, et cetera, we still have a way to go for some consumer startups to feel as solid staying here.”

One of the splashier moves came from formerly Cambridge, MA-based Baydin, whose founder Alex Moore gave a ride to Bay Area angel investor Dave McClure, pitched him, and nabbed a $100,000 investment as a result. The startup, which develops tools for managing e-mail inboxes, was already considering a move West to be closer to big names in e-mail, but the check from McClure and the opportunity to work alongside other companies in his 500 Startups fund sealed the deal, Moore says. “San Francisco has been everything we hoped it would be—vibrant, passionate about new technologies and startup companies, and focused on opportunity over risk,” he says. “Having spent a month out here, I would encourage any Boston startup founder to pay the Valley a visit.”

TaskRabbit, a Web-based community (formerly known as RunMyErrand) for swapping errand services, raised money from Bay Area investors in October 2009, shortly after participating in Facebook’s fbFund incubator program. This past June the previously Boston-based company kicked off its service in San Francisco and relocated its operations there. But the move isn’t “an indictment of Boston as a city where startups thrive,” says R. Ann Miura-Ko, partner of Floodgate Fund, which backs TaskRabbit. The company moved because it was expanding its errand-running services to San Francisco and the principals wanted to be on hand there, she says.

RelayRides and thredUP, both of which moved from Cambridge, also attracted investments from out West and relocated. But neither necessarily saw the Boston area as unfit to fuel their company.

“We started off in Boston because it was a great environment for a car-sharing startup—it still is,” says RelayRides chief operating officer Desmond Pieri. “However, as we raised … Next Page »

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