Is This Really Boston’s Next Media Mogul?

Yet the bulk — and the heart — of Barstool isn’t about the sports or girls. “It’s the stuff you don’t find anywhere else,” Portnoy explains. About half of the blog posts come from reader e-mails containing viral videos or photos; the other half are found by scouring the Web for anything funny, bizarre, or outrageous. “There are a million stories to cover every day,” says Keith Markovich, one of Portnoy’s writers in New York City. “It’s just a matter of picking the right one.”

Take, for instance, the recently posted photo of an 800-pound grizzly bear chasing after a 1,600-pound injured buffalo on a road in Yellowstone National Park. Barstool’s treatment? “This Bison Is a Gigantic Pussy.” The photo itself is arresting: an image of two beasts hauling ass down a stretch of pavement — with the smaller animal chasing after the larger. But in the hands of Barstool readers, it becomes something else. One reader offered analysis: “Bison never standed [sic] a chance. No lateral mobility, no quickness to the attack.” Another commenter had a recommendation: “Save this for when the B’s play the Sabres.” Within 48 hours, the item had garnered 120 Facebook shares and two dozen comments.

Ultimately, though, the key to Barstool’s success has been its willingness to evolve. In a span of seven years, Portnoy has built a website, dropped the gambling coverage, run more and more galleries of women, sold merchandise, and organized events such as concerts and contests. “There isn’t something we won’t try or do. We’ve always had money to do stuff — but it’s always, like, Where do you put it? How do you spend it?” he says. “We see where the tide is going and we try to go there quickly.”

Which explains how he figured out how to monetize a website, too. One of the worst-kept secrets in the media world is that many advertisers are desperate to be online-but have no idea what they want from online advertising. Part of the problem is that when it comes to the Web, the most effective ads aren’t ads; they’re pop-culture phenomena that just so happen to sell a product (think: Old Spice guy, E*Trade baby, Budweiser’s best commercials). Portnoy intuitively understands this, which is why Barstool’s promotions can be as entertaining as its posts. These campaigns help advertisers, sure, but they are also conspicuously in line with the ‘Stoolie ethos. That’s how Narragansett Beer’s “Search for New England’s Best ‘Can'” came to be, for example, or Miltons department stores’ “Pimp My Look” contest.

The revenue from those campaigns allowed Portnoy to launch a Barstool Sports.com last year in New York City, and he’d someday like to have outposts in Philadelphia, Pittsburgh, and Chicago. The only thing holding him back, he says, is time and talent. When he was looking for writers for the New York version of Barstool Sports, he decided to hold a contest: 500 people applied for two jobs, and Portnoy ultimately hired 25-year-old Kevin Clancy, who left a desk job in finance, and Markovich, who passed up going to journalism grad school because “blogging for El Prez sounded like way more fun.” Barstool New York’s traffic is about half of Boston’s. “We knew New York City would be a much bigger challenge, but it’s also a much bigger opportunity,” says Clancy. “If we can conquer New York, it’s going to be 10 times as big as Boston’s.”