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.

At the age of 10, Dave Portnoy was introduced to gambling by his father. As he shared on the "Spittin' Chiclets" podcast, the duo would often visit the horse-racing track, Rockingham Park, together, and easily picked up the habit and continued to gamble on sports throughout his childhood. When he was a student at the University of Michigan, he gained notoriety for writing about his bets on his website.

In 2019, Portnoy was whisked out of the New England Patriots versus Los Angeles Rams Super Bowl game by security due to his previous ban from NFL games. Speaking of the moment on Barstool Gambling, he described it as nerve-wracking, since he'd laid down a whopping $250,000 in favor of the Patriots. "That was the rush of my life though, when they took my phone away and walked me out in handcuffs," he recollected. "I had no idea what the score was." Luckily for Portnoy, he got out of the stadium jail richer after the Patriots' win.

Portnoy has had some major losses too. In November 2023, he lost $500,000 on one bet when the Philadelphia Eagles were defeated by the Buffalo Bills. "I quit gambling. F*** Buffalo, " an irate Portnoy tweeted then, but his decision to do away with betting didn't last long. A week later, he tweeted that he would place a $1 million bet on the Michigan Wolverines against the Alabama Crimson Tide.

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.

After he left the University of Michigan, Dave Portnoy had an $80,000-a-year sales job, which he detested even though he was good at it. He wanted something he could call his own. In 2003, Portnoy's parents fished money from his graduate school fund to help with the launch of Barstool Sports, the free newspaper.

Early on, Portnoy had no staff other than himself, and he concealed his lack of a proper workforce by using multiple pen names. "I didn't want people knowing that it was just me doing the company," Portnoy recalled on the Barstool Sports documentary series. "It was like, 'How can I make it seem bigger than it actually is?'" Portnoy presented the non-existent team at Barstool Sports as a group of average guys with a passion for sports, placing bets, and an equally strong appetite for women.

His inflation of Barstool Sports' success also extended to the search for advertising revenue. "I wanted Morton's Steakhouse to advertise ... So I just take a picture of Fleming's Steakhouse and I would stick it in the newspaper," he explained in the series. "I'd call Morton's and be like 'Hey, your competitor's advertising, man...you better get on this.'" Portnoy's persistence paid off since he eventually made enough money to hire writers.

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."

Dave Portnoy has made several smart business decisions in the past to keep his paper in business, but the idea that birthed the most success was altering the cover of Barstool Sports. From a simple introductory layout with just the newspaper title and logo on the cover page, the winning idea  — having full-sized pictures of models on the front page — came from the camp of photographer Eric Levin.

"A buddy of mine and I were driving through Faneuil Hall, and he mentioned Barstool Sports ... and he said, 'Dude, you should, like, put some pictures on the cover,'" Levin recounted on the Barstool documentary series. "There was a little picture of a girl and I was like 'We should do this like Maxim.' So, I think that night I emailed Dave. He emailed me right back and said, 'Yeah, we'd love to do that.'"

In November 2004, the first copy of Barstool Sports featuring a local cover girl was published. Subsequent issues of the newspaper featured the same formula until the publication of the physical copies was seized.

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."

In February 2020, PENN Entertainment first bought into Barstool Sports. Two years later, the sports betting powerhouse took complete ownership of the company for a figure in the neighborhood of $388 million. "The closing of the acquisition marks a major milestone for Barstool Sports as it celebrates its 20th anniversary," PENN Entertainment wrote in a press release.

Although PENN Entertainment hailed praises at the massive growth Barstool Sports had recorded in the betting space, seven months hardly went by before they parted ways in August 2023. In a post on X, formerly known as Twitter, Portnoy announced the end of their partnership and further blamed the split on attacks on Barstool Sports' nonconformist nature.

"We did this deal about three years ago, and I think both parties were like, 'We're gonna take this thing to the moon,'" Portnoy noted. "We underestimated just how tough it is for myself and Barstool to operate in a regulated world where gambling regulators, The New York Times, [and] Business Insider hit pieces [were] f***ing with the stock price every time we did something." In a 10-Q filing, PENN Entertainment indicated that Portnoy had only paid $1 to re-acquire full ownership of Barstool Sports.

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."

In an April 2022 post on TikTok, Dave Portnoy posted a long list of people, companies, and things he loathed. At the very top, and in all caps, Portnoy placed Business Insider's senior features correspondent Julia Black, who first blew the whistle on the sexual impropriety claims against him. Coming in second was the same publication's former CEO, Henry Blodget, whose exit he celebrated more than a year later in a November 2023 tweet. Business Insider's global editor-in-chief Nicholas Carlson, NFL Commissioner Roger Goodell, and former ESPN president John Skipper rounded out Portnoy's top five.

Dallas Mavericks shooting guard Kyrie Irving made it to Portnoy's list, but the latter admittedly liked him before he came to play in Boston. "I was actually pro Kyrie when he left Cleveland and came to the Celtics ... but he's just the worst athlete," Portnoy opined on his YouTube channel. "I hated him when he was on the Celtics ... He wouldn't shut up talking about how he's gonna go other places, and then the media would be like, 'Are you leaving?' He'd be like, 'How dare you ask me that?'"

The list of 41 people and institutions also included publications, like N Magazine and The Daily Beast, and surprisingly, the Empire State Building. "How lame is the Empire State Building?" Portnoy tweeted in January 2023 when the building lit up in his football rivals' colors. "What an absolute piece of s*** building. I'd be embarrassed to have it in my city."

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.

"One bite, everybody knows the rules," is Dave Portnoy's famous tagline on his popular pizza reviewing channel, "One Bite Pizza Review." "You may ask, how did he get started as one of the world's most famous pizza reviewers? In classic Portnoy fashion, there was a heated argument.

"I got in a debate with somebody ... 'If you could only eat one food the rest of your life, what would it be?'" Portnoy chronicled in an interview with Benzinga. "He said 'Burritos,' and then we did it." Portnoy went on a pizza-only diet for a month, then the thought struck him to give the slices a rating. "One Bite" turned into a pizza festival in 2023 and the rest is history, but one question still lingers: Which brand is his favorite?

"I love Sally's [Apizza] in New Haven and John's of Bleecker here in Manhattan," Portnoy declared of his top two in his conversation with Benzinga. When he first had a slice from John's of Bleecker Street on "One Bite," Portnoy was impressed. "This is the best pizza I've had so far in New York City," he said. And when he reviewed Sally's Apizza for the first time, he gave the joint a 9.2 rating.

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.

In a January 2017 blog post, Dave Portnoy announced his split from Renee Portnoy, popularly known by his fan base as the "First Lady." "No shady s*** on either side. I love her. I will always love her," Portnoy wrote. "We both needed a break to figure our s*** out. Nothing that is happening is behind the other person's back. She's f***ing awesome and we both love each other. " 

He further revealed that he had since moved on, and afterward, Portnoy's love life got messier. Barely two months later, he called out fitness instructor Jordyn Hamilton through a tweet in 2017. Two years later, a sexual video featuring Portnoy and model Sydney Raines was leaked. In a statement, shared via Instagram, Raines assured the public the clip was recorded consensually, and there was no bad blood between herself and Portnoy.

Portnoy's love life seemed promising when he was spotted getting cozy with internet personality Silvana Mojica back in March 2021. The duo became a couple, and when Adam's Apple caught up with Portnoy later that year, he revealed that he was open to tying the knot one more time. "I mean, I'm old as s***," Portnoy said. "So, it's like, I wouldn't be dating somebody if I didn't think there's a chance [to get married]." Sadly, Portnoy revealed that he and Mojica called it quits in a November 2023 episode of the "BFFs" podcast.