From the November 2013 issue of Entrepreneur

David Portnoy's Barstool Sports is the bible of bro culture. Rude, crude, sexist and often mean-spirited--even Howard Stern has complaints--the site has become a go-to for young men who say they are disenfranchised by the mainstream media. With legions of fans, Barstool is expanding its original content offerings and even eyeing a move into broadcasting. Is this take-no-prisoners style of entertainment the future? And can Portnoy continue to cash in on controversy?

The natives are growing restless. "We want Pres!" they chant. "We want Pres!"

Barstool Sports' Blackout electronic dance music party is approaching critical mass, but the site's founder, David Portnoy--the self-appointed El Presidente, aka The Mogul, aka Davey Pageviews--is unfazed by the controlled chaos erupting around him. Ignoring the entreaties of the capacity crowd assembled here at Boston's House of Blues, Portnoy sits inside the club's greenroom hunched over a borrowed laptop, his attention focused on blogging photos of a shirt-less fat guy in a Lucha Libre wrestling mask and cape, captured just moments ago at that night's Boston Red Sox/Baltimore Orioles game and sent in by a member of Barstool's rabid fan base.

An hour later, it's showtime. Several junior members of the Barstool staff squeeze into ill-fitting, sweat-encrusted Smurfs and Star Wars costumes, arming themselves with confetti cannons, fire extinguishers and other tools of the Blackout trade. When they begin dancing and cavorting across the black-light-illuminated stage, the audience--teens and twentysomethings uniformly decked out in neon tank tops, surfer shorts and flip-flops--explodes in appreciation, uncorking the kinds of shrieks and shouts typically reserved for rock stars, not bloggers and interns.

Portnoy surveys the spectacle from offstage, then returns to the greenroom. The Blackout audience may want Pres, but it isn't going to get him tonight. "I don't even want to be here," he grumbles. "I should be at home catching up on The Newsroom with a bowl of popcorn in my lap." Instead he goes home and bangs out another blog, this one posted to the site just after 1 a.m.

David Portnoy of Barstool Sports
David Portnoy of Barstool Sports

Portnoy is a man who does what he wants, when he wants, and his haters-gonna-hate attitude, tireless work ethic and uncanny understanding of the elusive 18- to 35-year-old male demographic have built Barstool Sports from a weekly sports-betting-theme print publication distributed for free at Boston transit stops to a digital multimedia juggernaut: a wide-ranging, unabashedly profane men's lifestyle blog bolstered by flourishing live events and merchandise businesses. A much-imitated, never-duplicated resource for the latest on sports, entertainment and women--the tent poles of the dude zeitgeist--the site is must-reading for a growing legion of high-profile male athletes and sports-media personalities, many of whom have appeared on the Barstool-produced online video series "The Bro Show" and podcast "KFC Radio," hosted by blogger Kevin Clancy, who heads Barstool's New York City efforts.

"If you polled all the players in the [National Hockey League], I'd say 25 percent of them read Barstool," says San Jose Sharks all-star center Logan Couture, a "KFC Radio" guest in February. "I started reading it about five years ago. It made me laugh, and I've been reading it ever since."

Fanning the Flames of Controversy

Not everyone finds Barstool Sports hilarious, however. Feminist groups have rallied against the site, which boasts daily features such as "Guess That Ass" and "Local Smokeshow of the Day," a spotlight of female college students from around the country. Portnoy has appeared on the TV newsmagazine Inside Edition to defend charges that the Blackout parties promote binge drinking and misogyny.

Portnoy's decision to post a nude photo of New England Patriots quarterback Tom Brady's 20-month-old son also earned him a visit from Massachusetts state police, got him banned from Boston sports radio station WEEI and even led to an on-air scolding from Howard Stern.

Portnoy is unrepentant. "We don't back down from controversy--we fan the fires," he says. "People think we go out of our way to create it, but we don't. We're not trying to gain new readers by being crazy-outrageous. Our readers get what we do, and I don't think about what it's going to look like to the outside world. I don't really care."

What Portnoy does care about is building a website liberated from the seriousness and self-indulgence of the sports-media establishment, a site unwaveringly faithful to its credo, "For the common man, by the common man"--critics be damned.

"Dave is hellbent on proving everything in the mainstream wrong," Clancy says. "He wants to prove all the advertising agencies are wrong, all the media agencies are wrong and all the PR agencies are wrong. He is fighting against everyone who says you have to play by the same cookie-cutter rules, and he won't stop until he proves he's right. It's his crusade."

Portnoy's ardent fans, the Stoolies, are right there with him. When students at Boston's Northeastern University launched the grassroots organization Knockout Barstool to protest what they call the site's "cycle of misogyny and rape culture," the Stoolies rushed to Portnoy's defense across all corners of the social media landscape. (Knockout Barstool representatives did not respond to requests for comment; as of this writing, the group's Facebook page and Tumblr site had not been updated since February 2012.)

The Stoolies are a complex and often contradictory bunch. Barstool Sports' comment sections are unconscionably mean-spirited, embodying the worst excesses of internet anonymity. Portnoy, himself, is the target of many insults, which run the gamut from blog syntax issues to his physique--and those are some of the milder remarks. The most extreme comments cross the line into outright hate speech.

"I wish they didn't do it. It reflects poorly on readers and poorly on us," Portnoy admits. "We've gone through periods of banning people. We don't have the manpower or the technology to accurately do it, so we do it the best we can. It's the nature of the internet, and it's something we have to live with, but it sucks."

Yet Stoolies are capable of genuine acts of kindness as well. On Veterans Day 2012, they donated $15,000 in less than 24 hours to purchase a new wheelchair for Zachary Parker, a U.S. Army medic who lost both legs and an arm while on patrol in Afghanistan. And in the wake of April's Boston Marathon bombing, Barstool produced and sold three Boston Strong charity T-shirts, donating proceeds of close to $250,000 to victims of the attack.

And for all those women who oppose Barstool Sports, there appear to be as many supporters. "I know there are people who don't want to go on the site because there are girls in thongs and their asses are everywhere, but who cares? Get over it. There's a lot more content there," says Jaimie, a 28-year-old digital project manager based in Boston and an avowed Stoolie.

Barstool Sports even has champions in the same sports-media establishment the site rails against. "Barstool makes me laugh on a daily basis," says Scott Van Pelt, an Emmy Award-nominated anchor on ESPN's flagship news program SportsCenter and the co-host of ESPN Radio's afternoon talk show SVP & Russillo. "It's not a bastion of great taste. But I'm an adult, and if I want to laugh at things I think are politically incorrect, I'm allowed to. You don't have to like it."

Rough and Tumble

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."

Unpolished Influence

There have been other crossover celebrity bloggers, of course--gossip gurus Perez Hilton and Harvey Levin of TMZ spring to mind--but Portnoy's entrepreneurial ambitions and everyman accessibility set him apart. Arguably the closest point of comparison is his Brady-gate nemesis Howard Stern: Both are provocateurs celebrating and satirizing the male id run amok. And like Stern, Portnoy has a fervent cult following among blue-collar, Joe Sixpack-types alienated by the polish and platitudes of the media powers that be. Also like Stern, Portnoy is a master at generating memes--at this year's PGA Championship, "Viva La Stool!" joined Stern fan staple "Baba Booey!" among the shouts originating from spectators lining the gallery.

Portnoy's Stern-like capacity for identifying and nurturing raw talent is evident. In addition to star protégés like KFC and Big Cat, the fan-favorite blogger who spearheads Barstool Chicago, Portnoy in 2010 discovered Jenna Mourey, aka Jenna Marbles--a Boston University sports-psychology student juggling a handful of odd jobs--and put her in charge of StoolLaLa, a short-lived spinoff site targeting female readers. Marbles and Portnoy parted ways in spring 2011, less than a year after her YouTube video "How to trick people into thinking you're good looking" went viral. Fast-forward to mid-2013, and Marbles' YouTube channel boasts more than 1.2 billion views and a subscriber base eclipsing 10 million, making it the fifth most-subscribed channel across the YouTube platform.

Portnoy's complaint: Marbles has not given Barstool Sports proper credit for launching her career. An April New York Times profile titled "The Woman with 1 Billion Clicks, Jenna Marbles" did not even cite Barstool by name.

"She told People magazine she fell into making YouTubes. Actually, no, you were working at a tanning salon and I hired you. That's how you started," Portnoy vents. "She thanked me once. She made a YouTube that explained her life. She said she was doing basically nothing, and I hired her and taught her everything about what she's doing now. I've hired one girl in 10 years, and it was her. She had something, but I wasn't able to harness it properly. I couldn't get her to understand it's a business. We never could get eye-to-eye." (Marbles did not respond to requests for comment.)

Another Portnoy find: Boston rapper Sammy Adams--the headlining act on the first Barstool campus concert tour, 2010's Stoolapalooza--who subsequently signed to RCA Records, scored a top 40 hit with the single "Only One" and appeared as himself on the CW Network prime-time soap 90210.

"The college tour was one of the first eye-opening moments," Portnoy says. "We had never been to a college campus before, and it was like the Beatles showed up. People had Barstool signs in the windows, and they were rushing at the buses. That's when I knew we had another way to make money."

Barstool Sports' Purple Starfish Productions offshoot, led by longtime staffer Paul Gulczynski (better known to readers as "Sales Guy"), now books branded concerts at clubs across the U.S., targeting off-campus sites near universities where inbound e-mail traffic indicates strongholds of Barstool fandom. At Purple Starfish's Blackout parties, audiences are encouraged to wear white to complement the signature black-light effects, while Foam events drop foam and froth onto the crowds below. A nationwide toga party tour is on tap for this fall and will keep some staffers on the road for close to 100 consecutive days.

During the academic year, Purple Starfish mounts a minimum of two concerts per week, routinely selling out venues up to 5,000 capacity. "The concerts sell themselves. They're as much about the crowd as they are the talent playing--it's like the world's biggest house party," Gulczynski says. "My biggest hurdle is getting venues to sign off. Once they have us, it's unanimously, 'Come back. You guys are a delight to work with, and the kids were all great.'"

Sales of concert tickets and branded merchandise--T-shirts, hats, stickers and flags--run roughly equivalent to advertising proceeds, a testament to the popularity of the Barstool brand but also a byproduct of the company's ongoing struggle to communicate its appeal to marketers.

"The greatest thing that Barstool has is influence," says Louis Roberts, a Barstool sales representative. "If Dave or one of the writers write something, the readers listen. That's what I sell: I tell [advertisers], 'You're not just buying the digital space. You're buying a branding deal. You're getting the best of both worlds.' It's just tough trying to explain that to people. I don't know why no one's figured it out. In my opinion, we should be making a lot more money than we are."

(Portnoy declined to disclose revenue: "I think revealing how well we do or how well we don't do can only hurt," he explains. "People see my lifestyle and know it's changing for the better, but I've never revealed real numbers.")

Portnoy refuses to jump through any hoops. "We do not play nice with media agencies. We will not do it. I am not going to buy you lunch to help you do your job," he insists. "The best way we'd work is having five to seven advertisers who get us and give us the majority of their budget, whether it's Axe or Trojan--people who are wasting money all over the place. We'd kill it for them. We'd murder it. But they don't want to talk about it. So we run our business with me not depending on ads. If we get them, it's additional revenue. If not, we make money directly from the people who read us, by selling shirts and doing concerts and events."

If and when the situation changes, it will be because advertisers have finally come around to Barstool Sports, not vice versa. "I have always said I'll walk away before compromising the brand. Unless I sell it for a billion dollars or enough where I never have to work again--then you can do what you want," Portnoy laughs. "But until that happens, we're going to run it the way people expect and the way that's gotten us to this point."

More Brogramming

With Barstool poised to enter its second decade, Portnoy is plotting his own move into broadcasting:

The company is mulling an offer from an unnamed local Boston TV station to launch a Barstool-branded series. Portnoy, however, is concerned about signing away his rights to any future Barstool TV efforts, and as of this writing, the contract remained unsigned.

The proposed Barstool series would essentially expand on "The Bro Show," documenting the blogger team's exploits as they travel across the country, mixing it up with celebrities and exploring America's bizarro underbelly. Previous "Bro Show" webisodes have featured Portnoy visiting the annual American Gerbil Society show, fielding kicks from former New England Patriots punter Zoltan Mesko and tending goal against Toronto Maple Leafs left winger James van Riemsdyk. ("El Pres definitely doesn't have a problem shooting off his mouth," van Riemsdyk says.)

Video segments like "The Bro Show" signal the future of Barstool Sports, Portnoy says. A July episode pitting Barstool against Red Sox slugger David Ortiz in a Wiffle-ball home-run derby generated 40,000 views in its first week online--not a huge number, Portnoy admits, but Stoolies spent more than 400,000 minutes watching the episode. "That's 63 percent audience retention for a 20-minute video," he boasts. "Our people watch everything. The time people spend on the site and the time they spend watching videos is what separates us. That's the Barstool difference."

With copycat sites like BroBible and Guyism aping Barstool's attitude and subject matter, video will continue to keep the competition at bay, Portnoy believes. "When we started there weren't any other 'bro blogs.' It was just us. Now there's so many people doing what we do--the same exact thing," he says. "We want to stay ahead of everybody else, and video is a natural. You don't see other blogs or people making the videos we're making, because I don't think they can. No one can do what we do."

Regardless of whether cable networks and advertisers ever come calling, Barstool Sports will continue evolving. But Portnoy is adamant that it will never change.

"If for whatever reason we needed money, we have two choices: We gotta conform, or readers gotta start giving us money. Our readers would say, 'You're not conforming. Stay how you are.' And we'd make more [money] than ever," Portnoy says. "Everything has an agenda, but we're totally unfiltered. It's the real thing--and people love it."