Is This Really Boston’s Next Media Mogul?

THE STATED CREDO of Barstool Sports  is “By the Common Man, for the Common Man,” and the website owes its existence to a particularly common urge: the desire to work for oneself.

After returning to Boston in 1999, Portnoy went to work for Yankee Group, a local technology market research firm, selling the company’s services to telecom customers. Even before his corporate gig, though, he knew he wanted to strike out on his own. His instinct was to find something in the gaming industry because, well, he liked to place bets. So he started cold-calling the HR and marketing departments at various Vegas casinos until a few execs agreed to meet with him. But when he finally flew out to Sin City, he was uniformly told that it was difficult to get into the business without any experience; unless he was willing spend a couple of years as a dealer, he should try something else. The job research wasn’t a total bust, though. A couple of executives from offshore casinos told Portnoy that if he ever created some sort of gaming publication, they’d advertise in it.

So that’s what he did. By August 2003, Portnoy had left Yankee Group and had published his first issue of Barstool Sports, a four-page black-and-white newspaper that featured gambling spreads, sports schedules, and fantasy-league stats. It was distributed at T stops around Greater Boston, and offered neither commentary nor cleavage. Because of the paper’s gambling-related content, PartyPoker, then the largest online card room in the world, threw enough advertising money at it to float the venture for its first year. “PartyPoker gave us our sea legs,” Portnoy says. He didn’t really have a long-term plan, but he also had almost no expenses — he had temporarily moved back in with his parents — and PartyPoker’s cash had bought him enough time to figure things out.

Unlike a lot of people in media — or at least people in old media — Portnoy doesn’t have any romantic notions about the business he’s chosen. It isn’t a calling or a passion or some sort of sacred trust. It’s a way to create something of value — while having a good time. “I always looked at it from a business perspective, like, How can this company make money?” he says.

After he launched the print version of Barstool Sports, he found that big companies weren’t willing to spend their advertising dollars on a publication devoted solely to sports, so he decided to employ the oldest sales gimmick in the universe — eye candy — by putting a picture of Jessica Biel on the cover. It worked, even if it was a blatant copyright violation. Soon after, a Boston photographer who did some work for Barstool Sports asked Portnoy if he’d ever thought about putting a local girl on the cover — a potentially buzz-creating move that would have the advantage of being legal. Portnoy took his advice, and the response was immediate. “From that day, the paper always had a local girl on the cover,” he says. And with the new packaging, advertisers both national (Bud Light, Miller Lite) and local (the Lyons Group, the Briar Group) wanted a piece.