Written By: Robert Cocuzzo | Photography By: Kit Noble

Barstool Sports founder and Nantucket summer resident Dave Portnoy is on a mission to save small businesses.

Dave Portnoy is known to rant. The self-styled “El Presidente” of Barstool Sports—a media empire now valued at more than half a billion dollars—Portnoy readily turns to his millions of followers on social media to air his frustrations, throw jabs at his enemies and dish out opinions that can ruffle more feathers than a My Pillow factory.

On December 11th, Portnoy directed his ire toward politicians in New York City who had just reinstated harsh COVID-19 restrictions on restaurants that Portnoy argued would do more to destroy small businesses than destroy the coronavirus. Like many of his social media posts, the three-and-a-half-minute video went viral, reaching more than five million people, including businessman and CNBC host Marcus Lemonis, who shot back: “Put your money where your mouth is…”

There’s a lot you can say about Portnoy, but one thing is for certain: He does not back down from a challenge. The very next day, he pledged $500,000 of his own money to launch the Barstool Fund, which would be directed toward supporting small businesses. This wasn’t the first time Barstool has done charitable work—the company has spearheaded a number of causes over its seventeen-year history, from backing Pete Frates’ campaign against ALS to supporting victims of the Boston Marathon bombings—but the plight of the small business community seemed personal for Portnoy.

“In many respects I still view Barstool as a small business,” Portnoy told me earlier this spring. “Obviously we’ve grown, but it took me ten years or so to start making any money. Every cent I earned went back into the business. It was a 24/7 grind. I just couldn’t imagine the pandemic hitting around year-ten of Barstool, because I would have lost everything.”

Portnoy’s allegiances to small businesses, particularly restaurants, likely also stem from his wildly popular “One Bite” pizza reviews, a regular video feature on Barstool where Portnoy judges a single slice of pizza from parlors around the country, including several on Nantucket, where he’s owned a summer home since 2016. Since starting them over a decade ago, the One Bite reviews have earned a cult following and can change the fate of a pizza joint overnight. Though he doesn’t shy away from giving critical scores right in front of the shop owners, Portnoy undoubtedly identifies with the hardworking pizza shop owners who like him built their businesses “brick by brick.”

After establishing the Barstool Fund, Portnoy began soliciting donations from both his readers as well as big names in his network. The fundraising effort quickly snowballed, amassing more than 200,000 individual donors including some significant contributors like car czar Ernie Boch Jr. who donated an unsolicited $1 million. Soon a call came from Green Bay Packers quarterback Aaron Rodgers who not only donated $500,000, but also became an advocate for the fund. Tom Brady kicked in next, followed by restaurateur and television host Guy Fieri. “There was a day that I was on the phone with Kid Rock and then Sylvester Stallone in a ten-minute span,” Portnoy said. “I was just thinking, ‘What is going on in my life right now?’”

Perhaps more memorable than the calls with donors are the calls Portnoy makes to the small business recipients. Dialing them up on Facetime, Portnoy delivers the news personally that the Barstool Fund is coming to their rescue. Once the business owners realize who they’re talking to, the look of relief in their beleaguered faces is undeniable.

“It’s certainly gratifying, but in a weird way I’m almost embarrassed,” Portnoy said of the calls, “because they’re thanking me, but it’s really the 200,000 people who donated that made it possible.” At press time, the Barstool Fund had raised more than $37 million and supported over 332 small businesses, everything from a sports bar in Michigan, to a tattoo parlor in California, to a daycare center in Ohio, to a pharmacy in Texas, to a restaurant in Boston.

Portnoy’s exchanges with the tearful small business owners cast the media mogul in a very different light than what he typically garners from his El Presidente persona. Controversy and outrage have never been far from the Barstool brand. Even the fund itself has detractors, some claiming that it’s little more than a vanity project for its founder. “They’re the same exact people who have a problem with everything I do,” Portnoy said. “The same people who have always had issues with Barstool continue to find issues with Barstool regardless of what we do.”

Indeed, for all his fans, there are likely just as many critics who take issue with controversial remarks Portnoy has said or written in the past. “The things that people who don’t like me say about me makes me sound really bad,” he insisted. “The people who don’t like me say ‘he’s sexist, he’s racist, he’s this, he’s that…’ It’s just garbage. People who don’t like me don’t have any clue of who I actually am.”

Portnoy, now forty-four, grew up in Swampscott, Massachusetts, where he attended high school before heading to the University of Michigan to study education. After a stint working for an IT firm in Boston, Portnoy launched Barstool Sports as a flimsy newspaper dedicated to fantasy sports whose lifeblood was mostly sports gambling advertising. The paper lived in relative obscurity for four years until debuting on the internet in 2007. Over the course of the next decade, Portnoy and his growing band of bloggers built Barstool into an enormously popular sports entertainment site that sold a majority stake to the Chernin Group in 2017. At the time, many sneered that the $25 million deal with Chernin was shortsighted, but the partnership supercharged Barstool. Three years later, Penn National Gaming purchased Barstool for nearly half a billion dollars, catapulting Portnoy to a level of fame and fortune unimaginable when he started.

When it comes to public figures, Portnoy is particularly public. There’s very little about his life that doesn’t get broadcasted to the world by way of his blog, podcasts, social media or frequent appearances on FOX News, CNBC, CNN or TMZ. Portnoy has achieved a rare level of fame, transcending multiple industries to become something of an everyman icon where his familiarity with his fan base makes him approachable. Portnoy says he rarely goes anywhere without being swarmed for selfies. “It is getting a little bit, I won’t say challenging, but it takes some time getting used to,” he said.

When asked what most people don’t know about him, he explains that he’s actually far more subdued than his El Presidente persona might suggest: “If you see me at a bar, I’m not the guy dancing around. I’m sitting in a corner.” Politically speaking, Portnoy insists that he’s “super socially liberal.” This might come as a surprise to the many people who watched his chummy interview with President Trump at the White House last June and assumed his political affiliations were right leaning.

“Sitting down with Donald Trump doesn’t make me some crazy conservative,” he said. “Trump asked me to do an interview, I said yes because he was the president of the United States. We invited Biden to do an interview; he didn’t accept it.” This hasn’t stopped pundits from speculating that Portnoy, even if unintentionally, is leading a whole new face of the Republican Party dubbed “Barstool conservatives.”

“Regardless of Portnoy’s own ambitions, I fully expect the future of the Republican Party to belong to Barstool conservatives, which is to say, to a growing but so far almost invisible coalition that could very well carry the White House,” wrote Matthew Walther in The Week this past February. “The Barstool conservative movement will not have institutions in any recognizable sense, certainly not think tanks or highbrow magazines, but it will be larger, more geographically disparate, younger, and probably more male. It will also, I suspect, be more racially diverse, much like the portion of the electorate that gave Trump 74 million votes in 2020.”

Despite running for mayor of Boston as a Libertarian in 2013, Portnoy says he has no plans of leveraging his vast following for a political career anytime soon. Still the very speculation around his political ambitions illustrates just how far-reaching his influence has become. Whether it’s launching a new sports gambling platform with his partner Penn National, signing Hall of Fame legends like Deion Sanders as Barstool employees or marketing any number of products from clothing to his own pizza line, Portnoy’s influence is a hot commodity.

Beyond the Barstool Fund, his most conspicuous foray over the last year has been in finance where he’s helped galvanize a whole new demographic of stock market traders. Portnoy started day trading at the beginning of the pandemic and quickly gained national attention from live-streaming his buying and selling. Soon he was talking stocks on CNBC, which gave rise to yet another Portnoy alter-ego he dubbed Davey Day Trader.

Under his banner of DDTG— Davey Day Trader Global—Portnoy activated flocks of new retail traders during the pandemic who had never bought a stock before. The might of this new breed of trader came into full view during the GameStop phenomenon this winter, when thousands of retail traders coordinated online to buy up failing stocks that large hedge funds had shorted. The surge in stocks like GameStop and AMC brought a number of hedge funds to their knees and eventually prompted the trading platform Robinhood to take the unprecedented action of temporarily halting the trading on these stocks.

Portnoy, who said he lost $700,000 because of Robinhood’s actions, blew a gasket, calling the actions of the trading platform’s CEO Vladimir Tenev utterly criminal. “Vlad and company stole it from me and should be in jail,” he tweeted. After Tenev appeared before Congress to explain his actions, Portnoy managed to get the billionaire CEO to answer his pointed questions during a live broadcast aired on his social media accounts. Portnoy lambasted Tenev, grabbing headlines like that of the New York Post, which gushed: “Congress is nothing compared to Davey Day Trader.”

Two weeks later, Portnoy announced that he was backing an exchange-traded fund called BUZZ ETF, which uses an algorithm to poll the positive sentiment regarding stocks across social media for inclusion into its index. After a robust promotion campaign over Portnoy’s social media, the BUZZ ETF debuted on the New York Stock Exchange in early March and ultimately garnered $280 million in inflows during its first day of trading. Barron’s called it the twelfth best debut on record, “making a bigger splash than Black Rock.” Clearly Portnoy’s promotional power was still intact.

Come summertime, Portnoy can regularly be seen around Nantucket, where he started visiting twenty years ago before buying a home of his own. “It’s truly my favorite spot in the world—bar none,” he said. As for Barstool itself, Portnoy is riding this rocket for as long and as far as it can go. “Barstool has already done more than I would have ever dreamed in a gazillion years,” he said. “I started Barstool to make $50,000 a year and like what I am doing. It wasn’t to create a media empire, it just happened. We’re so far beyond what I would have ever imagined in my wildest dreams.” And armed with his Barstool Fund, Portnoy is on a mission to help keep the dreams alive for many other small business owners across the country.

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