An acquaintance of mine, “Jimmy,” touts his self-perceived masculinity to the point of self-parody. He once told me that his 80” TV is what “real men” have. He's a “gun nut” with a large firearms collection and an expensive pickup truck. Attached to his golf bag is a golf towel advertising, “SATURDAYS ARE FOR THE BOYS,” the most popular meme emanating from media conglomerate, Barstool Sports.
“Stoolies” believe that Saturday’s when a man leaves his family behind and hangs out with his buddies, drinking, golfing, watching sports, bantering about the “racks” on various “smokeshows,” etc.
Barstool’s swaggering frontman and owner, Dave Portnoy—who sometimes refers to himself as “El Presidente”—is as visible as media CEOs get. He's enhanced his formidable notoriety with his successful YouTube pizza reviews, which he makes all over the east coast. Comedians, sports stars, and famous actors appear in them, but Portnoy remains the focal point. His promotional skills are on full display when he says his buzz phrase before every review—”One bite, everyone knows the rules”—and then proceeds to take about six bites out of the slice. I tell myself I'm not going to click on these videos when I see them on YouTube, but I usually do. I'd never imagined watching somebody eat pizza could be so entertaining.
Portnoy's passions appear to be money, pizza—he runs the annual One Bite Pizza Festival in New York City—and sports betting. The New York Post regularly covers his betting results while reporting in headlines on his comments on a host of topics, as if he's a modern-day H.L. Mencken. He's met with Trump at the White House. Things are going well for the 48-year-old University of Michigan grad (education major) from a town just outside of Boston.
Barstool’s a digital media company Portnoy now owns outright after gradually selling Barstool Sports to Penn Entertainment in a series of deals that totaled roughly $551 million. In 2023, he bought the company back outright for $1, a deal that some have joked was better than the Louisiana Purchase. Multiple controversies haven’t slowed the firm’s success.
ESPN canceled "Barstool Van Talk" in 2017, after just one episode, because of what ESPN boss John Skipper called Barstool's toxic reputation and inflammatory content. The NFL revoked Barstool’s credentials. Old videos reveal Portnoy using the n-word, and also doing blackface, but they were just temporary speed bumps for the adversity whisperer.
Barstool’s never been popular among progressives. Media Matters has called it a “cesspool of misogyny and bigotry." Barstool used to run blog segments like “Name That Ass” and “Name That Rack” that fit its frat-house, locker-room sensibility. As the media company pursued mainstream advertisers, bigger media deals, and broader appeal beyond young males, these features quietly faded, replaced by podcasts, gambling content, and personality-driven shows.
Portnoy’s original “shock first, apologize later,” clickbait philosophy eventually yielded to his business ambitions. He started the enterprise in 2003 as a free, black and white print publication in the form of gambling-related leaflets he used to hand out in the streets and subways of Boston. The fairly tame sexual content that followed was a natural fit for the young, white male audience, but as a savvy businessman, Portnoy came to realize that podcasts, video shows, live events, and betting content generate more sustained attention than the fleeting visits that girly photos produce.
That diversification produced multiple revenue streams, one of the keys to Barstool’s success that other digital media businesses overlook. Moreover, the use of social media and emerging digital platforms to boost the business organically without having to spend on traditional media advertising allowed Barstool to scale without a large initial capital input.
Portnoy’s pioneered a brand-building effort that embodies the au courant business dictum that every company, no matter what it sells, needs to be a media company. Years ago, Bill Gates argued that in the digital future, “content” would be king for all kinds of firms. Later on, marketer Joe Pulizzi popularized the concept of companies acting like publishers first, to attract a loyal audience, and then moving on to the monetization stage. In the inchoate stages of his business, Portnoy, acting as a publisher, used content to create a tight message that worked for a very specific group of people.
The raw and unfiltered El Presidente, like Martha Stewart, Hugh Hefner and Oprah Winfrey, built that customer base around his personality. Portnoy is the Barstool brand. Anti-establishment and unconcerned with what anyone thinks about him, he gives his audience of youngish men exactly what they're looking for. With the exception of Elon Musk, Portnoy doesn't talk like other corporate bosses. Nobody can listen to Mark Zuckerberg, who has the effect of someone waiting for a software update to finish installing, and remember a thing he said 10 minutes later.
Portnoy’s Lincolnesque description of his brand when he started it was, “by the common man, for the common man.” Translation: anti-snob, grassroots, unfiltered through experts and gatekeepers. That phrase lives on, but Portnoy’s outgrown it in his luxurious personal life. His fans don't hold it against him, as he still often projects the persona of a regular guy ranting about his sports teams underperforming and his losing bets, which are sometimes as high as a million bucks. “Stoolies” aren't concerned about their guy flaunting his wealth. They see his success story as aspirational.
With a net worth upwards of $250 million, and a real estate portfolio valued at approximately $95 million, including a $42 million waterfront compound in Nantucket, Barstool’s semi-abandoned the common man persona. Portnoy's stated publicly that he's “rich as fuck,” and posts videos showing his dentist making house calls to his estate.
Like Trump, Dave Portnoy’s a Teflon leader. He doesn't avoid controversy, he metabolizes it. In a 2010 blog post, he wrote, “We don't condone rape... however if a chick passes out that's a gray area.” In a 2016 video, Portnoy joked that women in size six skinny jeans "kind of deserve to be raped." In 2017, the Barstool star known as KFC stated this about a journalist who had criticized the sexism at Barstool: “If I was Julie DiCaro, I’d be sleeping with one eye open. I’d be watching my back." Female sports reporters are wary of throwing shade on Barstool, lest the mob of overgrown Stoolie boys descend on them.
Despite such ugliness, Portnoy continues to sail above the storms. In the modern media environment, audacity can be the greatest asset of all. El Presidente has been smart enough to tone down the most egregious Barstool misogyny while retaining his outspokenness. Portnoy's prospects appear sunny. He’s built a media empire by breaking the rules his competitors are too cautious to buck, and his audience loves it.