Will Boston succeed in a Web 2.0 world?

To understand the Boston-based high-tech community, it seems you must understand baseball: Bostonians’ signature neurosis over being second-best flowers in both arenas. And when financiers and technology executives met recently to talk about creating a climate for Web 2.0 startup success here, they used the language of the operatically accursed, beloved Red Sox, invoking RBI more often than ROI.

It was clear at the MIT Enterprise Forum Wednesday that whatever game they’re playing here, they’re not used to winning. Even the eclipse of the homegrown minicomputer giants like Digital Equipment Corp. still rankles.

“There’s a cultural challenge here; we perceive ourselves as the lesser, smaller coast,” said Michael Skok, partner with North Bridge Venture Partners. “We live in the shadow of DEC, but there’s no reason for it.”

While Skok counseled Boston-area entrepreneurs to be power-hitters who can rack up home runs, Fox Interactive Media’s Adam Bain said he looks for steady players who reliably get on base.

Bain invoked the strategy followed by Billy Beane, general manager of the Oakland Athletics, who couldn’t compete with the big-spending Yankees to hire star players, so instead concentrated on what had been an overlooked statistic — players’ on-base percentage — to build a winning team made up of unglamorous but strong players.

“If the goal is to swing for the fences, you’ll have a lot of strike-outs,” Bain said. “Guys like us look for on-base statistics.”

Jeff Taylor is certainly a local home-run hitter: He co-founded job-listings site Monster.com and boasted that he was able to retire in August of 2005 and start a new company. His new venture, Eons, is a Boston-based Web venture targeting the 50-and-older demographic. Eons’ first round of funding was bicoastal, with $10 million raised between Silicon Valley’s Sequoia Capital and Cambridge’s General Catalyst Partners. But Taylor notes that the tech giants are no longer based in the Northeast.

“We’re missing the companies that will buy us and keep us here,” Taylor said — no doubt mindful that the most realistic exit strategy for Web 2.0 era entrepreneurs and investors is the acquisition, not the blockbuster IPO of the last decade.

Taylor thinks Boston firms need to do a better job of promoting their strengths, particularly in what he called “deep technology” — even though the glamour these days is not in technology as much as in the services that ride on top, such as those provided by Google and Yahoo, he acknowledged.

North Bridge Venture Partners’ Skok also thinks Web 2.0 can let area entrepreneurs play to Boston’s traditional advantage. “There’s a phenomenal amount of infrastructure under Web 2.0,” he said, adding that it is “very much happening on the East coast.”

And despite the local inferiority complex, Boston’s cultural values do give it an edge in some respects, Skok said. If he were a CEO choosing a company location, he would pick Boston “in a heartbeat,” he said, because employees are more loyal and hardworking. While denizens of Silicon Valley drive themselves hard, Bostonians are less motivated by money and more by love of the work itself.

So it’s not whether you win or lose, but how you play the game?