Details You Probably Didn't Know About Dave Portnoy

Dave Portnoy may be known as the founder — or "El Presidente" — of Barstool Sports, but the entrepreneur had two other major business ideas back when he was getting started. First, Portnoy thought about reselling second-hand college furniture. "We'd go pick it up, warehouse it, and sell it online for dirt cheap," he explained in a conversation with Barstool Sports. Although the plan didn't leave its infancy stage, he developed his next scheme, a platform called "Next Step Scouting" meant to help Division III college athletes get scouted. Ultimately, Portnoy went with his next idea, a sports betting blog that eventually became Barstool Sports.

Over the years, Portnoy has made headlines in both good and bad lights. In December 2020, the online tycoon turned heads when he launched The Barstool Fund to support small businesses during the COVID-19 pandemic. Nearly a year later, a report of sexual misconduct allegations published by Business Insider resulted in a defamation lawsuit by Portnoy that was eventually dismissed. 

From an early introduction to gambling, a major dream that never saw the light of day, and a rocky love life, all leading up to what is perhaps the world's most profitable acquisition, here are details about Portnoy you probably didn't know.

In high school, Dave Portnoy was an average football player, but an exceptionally good baseball outfielder. "I would describe myself as a dominant high school baseball player," Portnoy remarked in the Barstool Sports documentary series about the founder. "We probably lost like three or four games my entire high school career."

Portnoy — who got started on the Swampscott High School baseball team as a freshman — won the triple crown in his junior year and played until the end of his high school career. His teammates recalled how Portnoy managed to hit some home runs during his tenure on the team. His sophomore year in 1993, the team won the state championships, and an exhilarated Portnoy passionately dissected the events in a post-game chat with the press.

According to his head coach at the time, Frank Defelice, Portnoy possessed an enchanting sense of humor, which made him a delight to work with.[6:33]"Every coach would like to have a guy like him on your team," Defelice said in the Barstool documentary. "He kind of kept things loose ... I used to like some of the things he did. I mean, it made me laugh. He always had something to say." Despite his promising future, Portnoy's dreams of playing Division III baseball hit a wall when he incurred an unfortunate shoulder injury while playing football.

When he created Barstool Sports, Dave Portnoy sought the most inexpensive methods of getting things done. The company's logo, for instance, was made using clip art after his original logo was too expensive to reproduce. Portnoy was not just the only writer but also Barstool Sports' only distributor. He delivered the newspaper to workers on morning transit by himself, before realizing it was a laborious task if he were to reach a wider audience.

Portnoy then sought the services of "an army of homeless people." It was as chaotic a choice as it sounds. "They didn't show up, they were drunk, and my parents and I couldn't control them," he told the Barstool Sports blog. He eventually axed them and hired models to do the work. The writer would often wake up at the crack of dawn to supervise morning distribution, get back home to prepare the following week's paper, and return in time to oversee evening dispatch.

The strategy worked for some time, but the money he earned from advertisements wasn't enough to keep the system going. Portnoy purchased a minivan afterward, which he used to ply different routes in Boston. "It was horrible and exhausting," he recounted of that phase of being a business owner in the blog post. "But even though it was way more work than my sales job, I preferred it because I was doing my own thing."

After the Barstool Sports brand had found an online footing, the Dave Portnoy-led company took the college scene by storm. First came the company's concert series, Stoolapaloza, but Portnoy quickly outgrew the venues. Barstool then pumped a ton of money into its next project, the "Back to Stool" tour, which was an epic flop.

But their next party series, called the "Barstool Blackout Tour," finally hit the jackpot. "It was a party you did in, like, your house, but it was just in a professional venue," Portnoy explained in the Barstool Sports documentary about the tour. "It just had no rules ... it's something that can only exist for the short time it did." The ungoverned sold-out crowds at Portnoy's "Blackout" parties included ladies donning low-cut tops with luminous neon garments and EDM music. The tour's crew wasn't made of professionals, and instead, Portnoy and his buddies operated from a grim office in the outskirts of Boston.

In March 2012, Portnoy brought the "Blackout" parties to a steady halt, largely due to the state of Massachusetts' strict rules about alcohol. At the time, he said in a conversation with the Boston Herald, "It just doesn't seem like Boston is friendly to nightlife of our sort, at least. It goes against everything our brand is trying to do, if we're doing events where we know kids are spending money and getting turned away."

Dave Portnoy has a whole load of people and things on his hate list (details on this next) but to what extent can he go just to prove a point to someone he doesn't like? The answer to that lies in a feud Portnoy had with Boston's gambling radio station, WEEI, where he briefly worked. "I hated them," Portnoy revealed on the "BFFs" podcast. "We had a big controversy. I used to be on the air, they kicked me off."

After he left the radio station and Barstool Sports became successful, Portnoy attended a silent auction held by a clothing store that had the radio station also in attendance. The entrepreneur was determined to outshine his former workplace. "Out of spite, just to show I was doing well, I just won every auction," he narrated.

Although that particular auction had a good ending on his side, a different one had a sour aftermath. In May 2020, Portnoy was set to watch Monday Night Football with NFL Commissioner Roger Goodell — who he has trolled for years, starting when Portnoy staged a protest against Tom Brady's suspension during the "Deflategate" scandal — after putting up a $250,000 bid at an auction for COVID-19 relief, as he revealed via X. His joy was short-lived when the league canceled the appointment after an apparent investigation. Portnoy took to social media to voice his disapproval of the move in a tweet which he partly captioned, "Goodell is a coward. Hates charity. Hates kids."

Despite being a bankable businessman, there's one thing Dave Portnoy's money can't buy: skipping the waiting line at a Louis Vuitton store. Portnoy recounted a time he had to wait for his turn at the high-end retailers' in the company of his then-girlfriend and had his patience tested. "I got into it at Lous Vuitton," Portnoy narrated. According to his account, there were 15 people ahead of them in line, and the staff at the outlet asked the couple to wait for 20 minutes. 

"I looked at the guy, and it was a d***head thing to say, and I go, 'What does my net worth have to be to get in here? 100 million? 200 million?'" Portnoy continued. "I'm like, 'I'm not waiting.'"

It took around 45 minutes for Portnoy's ex-girlfriend, Silvana Mojica, to get attended to after he left. She still couldn't purchase anything because the credit card was in Portnoy's name. When she called him, Portnoy maintained that a simple Google search would have proven they were a couple. "I feel like [when] something is unjust I complain," he concluded.

Taylor Swift and Travis Kelce's relationship sent the internet and the NFL into a frenzy when it was made public, but Dave Portnoy wasn't impressed by the NFL's overexposure of the singer when she attended one of Kelce's games. Portnoy took to "Varney & Co." to express his disapproval. "Before we go further, I got to clarify. I am a Swiftie," he declared. "Let's not paint me as anti-Swift. I'm wearing the friendship bracelets right now. I love Taylor Swift."

While he may have taken shots at the NFL for its obsession with the pop star's relationship, true to his word, Portnoy has been consistent in supporting the "Blank Space" singer. When Swift released "Speak Now (Taylor's Version)" in July 2023, Portnoy said he was bewildered by the singer's musicality in an Instagram review. Portnoy also gave a nod to Swift's concert performance in a May 2023 tweet, while wearing a string of friendship bracelets. Swift, he said, was a one-of-a-kind artist who could keep her loyal fan base high-spirited for three hours.

Back when Portnoy made a hate list, he put Kanye West on it for one reason: the infamous phone call. "Him and f***ing Kardashian Kim, they edited that phone call of [Swift] when she said she agreed to be the lyric in the song, which she did not," Portnoy said on his YouTube channel. Finally, to prove his role as a staunch Swiftie, Portnoy made an Eras Tour jacket which traveled from fan to fan during its leg in the United States.