Recalculating His Risks Once at the center of the VC-backed dot-com universe, a former Flatiron Partners golden boy takes some personal stock.
(FORTUNE Small Business) – We're at sold-out, beer-drenched Fenway Park, sitting pretty in a pair of $55 seats hard behind the Seattle dugout. "Feels like a birthday present," says Seth Goldstein, a citizen of Red Sox Nation (now an expat living in Manhattan) who turned 31 the day before the game. He's wearing Abercrombie cargos that fall to his shins, a short-sleeved madras shirt, white canvas sneakers with no socks, a vintage Red Sox cap, and one of those WE'RE NUMBER ONE! foam finger mitts. "It's liberating to be a fan at Fenway," he says as the noise in the crowd rises. "I've been feeling very repressed."
Last year at this time, Goldstein was a poster child for the new economy, a self described "boy wonder" with two Web ventures under his belt and a fantasy job that put him "not at the center of the universe," he says, correcting me, but "at the top." At Flatiron Partners, Silicon Alley's hottest VC firm, he was entrepreneur in residence, guiding the deployment of more than $50 million of the firm's capital. Today Flatiron is a trivial subset of Chase Capital Partners and Goldstein, sad to say, had a hand in its rapid decline. Among the spectacular failures with which he was closely identified: Kozmo, the hip and speedy bicycle delivery service that we always knew was too good to last.
Goldstein bristles at my suggestion that maybe VCs like him, with their outsized expectations, were somehow responsible for the collapse of the Internet economy. "That's bulls--t," he says. "The entrepreneurs asked for the money. They can't have it both ways." But two minutes later he's admitting, "I definitely feel a sense of blame." He's hopeful that the experience will pay off for everyone involved "at some time, in some form," but then he adds softly, "Maybe that's just a stoic response to failure."
Goldstein is working on a screenplay and building some "personal equity" with courses in photography, cooking, and kung fu. He's still doing deals--he has angel money in Libida, "a women's adult entertainment and e-commerce site"--but it's not the same. "Nobody's hustling now," he says.
Before all this started, Goldstein was designing Websites at night and sleeping on his best friend's couch. Now he has a wife, a 2-year-old son (plus a baby on the way), a paid-for co-op on the Upper West Side, and a savings account that gives him ample time to plot his next move. But sometimes he wonders if, now that the pixie dust has settled, we're not just facing 20 years of making things better without really innovating. "That," he says, "scares the f--k out of me."