The Man Behind the 'Bible of Bro Culture'

The Barstool Sports headquarters in Milton, Mass., is a dump. There's no other way to put it. A former doctor's office located nine miles south of Boston and walking distance from Portnoy's home, it's virtually anonymous, identifiable only by a slim cardboard sign emblazoned in ballpoint pen with the Barstool Sports name, affixed to the mailbox adjacent to the front door beneath layers of masking tape. The interior suggests the unholy union of a fraternity house and a crime scene: Beer advertisements featuring half-naked women adorn the walls, towers of junk wobble in every corner, and the carpet is soiled with a panoply of dark dribbles and stains.

The impish Portnoy holds court from an attic office above the fray, dressed in a "Bro Surf" T-shirt and blue jeans. The Barstool headquarters, he says, "goes with the brand. We don't try to impress everybody. Those guys don't need anything nice down there, and I certainly don't."

David Portnoy of Barstool Sports

Barstool content is similarly rough around the edges. Portnoy and his growing blogger team publish between 70 and 80 posts each weekday--everything from sports commentary to stream-of-consciousness tirades to bikini shots to coed slide shows ripped from Facebook--no finesse necessary. Spelling mistakes and punctuation errors are commonplace, and the site design is no-frills.

But don't sleep on Portnoy's uniquely acerbic wit, sly social commentary and uncommon knack for viral-friendly catchphrases. A born sloganeer, he has devised a lexicon of Barstool signatures, including "smokeshows" (i.e., beautiful women), "hardo" (an arrogant or obnoxious male) and, most famously, "Viva La Stool," the rallying cry that has spawned countless homemade signs hoisted at sporting events, live news broadcasts and even the 2011 wedding of Prince William and Kate Middleton.

"The first time I used 'Viva La Stool,' I was just bragging about something. People grabbed it, and it went viral organically," Portnoy says. "There are almost no other websites that have the type of readership we do. [Advertisers] should be like, 'That's why I need to be on that site. Because if he says something or does something, the readers react to it.'"

Portnoy didn't set out to build a cult phenomenon. Hell, the guy didn't even set out to build a website. The 36-year-old Swampscott, Mass., native launched Barstool Sports in 2004 after quitting his sales gig at IT market research firm Yankee Group. "I knew I wanted to start my own business. I was a degenerate gambler, and I also knew I wanted to be in that field," he recalls.

After a series of unsatisfying meetings with Las Vegas casino executives, Portnoy spoke with several offshore casinos. "They all said, 'Don't do a website, because they're all cluttered with gambling ads. But if you had a physical handout, we'd be interested.' I had the sales background, so I sold a year's worth of ads."

While the embryonic print edition of Barstool Sports focused on gambling tips and fantasy-sports projections, Portnoy soon began documenting his personal life and causes célèbre like reality TV and dogs, with each successive article adding new facets to the larger-than-life El Presidente persona--brash, blunt and brutish, but also refreshingly candid and scathingly self-deprecating.

"El Pres is a character Dave plays. He's one of the most regular, nondescript guys going, and I mean that as a compliment," says stand-up comic and Boston sports radio personality Jerry Thornton, a longtime Barstool contributor. "He's got a lot of 'Masshole' in him--guys here love breaking each other's balls. He isn't afraid to tell you that you suck while he's being a friend to you. That's Barstool: It's honest and it's funny, and that's what people are looking for but don't get elsewhere."

Readers responded so favorably to El Presidente's ranting and raving that Barstool Sports quickly outgrew its fantasy-gaming origins. "I was lucky people liked my writing. They really liked the off-the-wall stuff," Portnoy says. "There's two things I think I've done well: I know what funny is. I recognize it whether it's on TV or whatever. And we react quickly--we make a decision and we go. We follow what people are reacting to. And that's how Barstool changed from its original concept
to what it is today."

Barstool Sports' progression from gambling rag to lifestyle blog reached warp speed when Portnoy expanded to the web in 2007, quickly embracing the possibilities of social media sharing and posting new content around the clock. He finally shuttered the print version in 2010, a year after hiring Clancy and launching Barstool New York, the company's first major move outside of the Boston market.

"That's the first time we saw that people want their own Barstool," Clancy says. "Each city wants their own website, and having someone in that city like me who knows exactly what a [New York] Mets fan or Jets fan is thinking makes all the difference. "You can't replicate Boston. It's the crown jewel of the empire. But you can make your own version of that. It's all about the local feel."

Barstool Sports now encompasses five sites, including Philadelphia and Chicago outposts, as well as the campus-theme BarstoolU (Motto: "By the C-minus student, for the C-minus student"), each with its own editorial staff and sensibilities, operating almost completely autonomously. There's also a so-called "superblog" that consolidates content from across the network. More than 4 million unique readers visit Barstool sites each month, driving more than 80 million page views.

"The business model long-term is opening up as many of these [local sites] as we can," Portnoy says. "We have a hard time finding guys that are the right fit. It's not enough just to be a good writer--you have to have a personality that can play. That's what separates us from a lot of blogs. In Boston we're as big as any media outlet. If you can replicate that everywhere, then you have something massive."

Chicago-based writer Jason Ankeny is the executive editor of Fiercemobile content, a daily electronic newsletter dedicated to mobile media, applications and marketing.

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This article was originally published in the November 2013 print edition of Entrepreneur with the headline: Agent Provocateur.

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