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," which was 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, the popularity of Barstool Sports has skyrocketed, and 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.

Still, there's more to the controversial entrepreneur than meets the eye. 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.

Dave Portnoy was introduced to gambling by his father when he was 10 years old. Dave and his dad, Mike Portnoy, would often visit the horse-racing track, Rockingham Park. As a result, the entrepreneur picked up the habit and continued to gamble on sports throughout his childhood. Dave eventually attended the University of Michigan, where he gained notoriety for writing about his bets on his website.

Dave's love for gambling extended well into adulthood, and he has unsurprisingly had some major wins. In 2019, he was whisked out of the New England Patriots versus Los Angeles Rams Super Bowl game due to his previous ban from NFL games, even though he'd laid down a whopping $250,000 in favor of the Patriots. Speaking of the moment on Barstool Gambling, Dave said, "That was the rush of my life though, when they took my phone away and walked me out in handcuffs...I had $250,000. I had no idea what the score was." Luckily for Dave, he got out of the stadium jail richer after the Patriots' win.

Dave has had some major gambling losses too. In November 2023, he lost $500,000 on one bet when the Philadelphia Eagles were defeated by the Buffalo Bills and tweeted, "I quit gambling. F*** Buffalo," only to tweet that he would place a $1 million bet on a Michigan Wolverines vs. Alabama Crimson Tide game a week later.

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. "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.

Dave Portnoy earned a bachelor's degree in education from the University of Michigan in 1998. Afterward, he landed a sales job that paid $80,000 annually. Although Portnoy was a skilled salesman, he detested his job and 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 in 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 founded Barstool Sports, Dave Portnoy sought the most inexpensive methods of getting things done. The company's famous logo, for instance, was made using clip art because the original design was too complex to print. Similarly, Portnoy was Barstool Sports' only distributor and would make morning deliveries himself. The daily task proved to be laborious, so Portnoy sought the services of "an army of homeless people," as he told the Barstool Sports blog. The decision turned out to be as chaotic a choice as it sounds. "They didn't show up, they were drunk, and my parents and I couldn't control them," Portnoy recalled, and added that he axed the rogue team and hired models to do the work.

Portnoy still faced financial constraints and was unable to pay his staff. He eventually purchased a minivan, which he used to ply different routes in Boston. That, too, wasn't an easy task, since van had its own set of problems. "It got booted by city hall while I was in a bar," Portnoy recounted in the Barstool Sports documentary, "It got stolen, and then it just reappeared. They just drove it until it ran out of gas. And they smashed it with a screwdriver to start it. I could never use the keys to start the thing again, I'd use my seatbelt, like, to turn it on."

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.

The story of how Levin began working with Barstool Sports is a serendipitous one, as the photographer recounted in the Barstool documentary. "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 narrated. "There was a little picture of a girl and I was like 'We should do this like Maxim [magazine].' 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 more seductive cover stars until the company seized the publication of physical copies.

When Barstool Sports became popular online, 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, the "Barstool Blackout Tour," became a huge success. "It was a party you did in, like, your house, but it was just in a professional venue," Portnoy explained in a 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."

Dave Portnoy and his ex-girlfriend, model Silvana Mojica, first sparked dating rumors in 2021, had a three-year romance, and broke up in November 2023. When the pair was still an item, they attended numerous events, including the March 2023 showcase of Louis Vuitton's Spring/Summer 2023 collection in Miami.

Portnoy had a sour history with the luxury brand, as he explained on a July 2022 episode of "The Dave Portnoy Show with Eddie & Co." "These new fancy stores, they make you wait in line to shop there, I won't do it," Portnoy said, and continued, "I got into it at Louis Vuitton ... I just needed a bag. They're like ... '[It'll take] 20 minutes, come back. We'll text you.' 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, who was in the company of Mojica at the time, eventually left. Mojica then went to a Chanel store on her own, where she had to wait for 45 minutes for her turn in line. She still couldn't make a purchase because she was using Portnoy's credit card in his absence. Portnoy opted to talk to Chanel's customer service, but he was put "on hold for an hour."

"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 revealed he went on a pizza-only diet for a month, then the thought struck him to give the slices a rating.

In his first "One Bite" review, Portnoy visited Town Spa Pizza in Stoughton, Massachusetts, and gave it a 10.0 rating. The entrepreneur quickly retracted its rating to 9.0, only because he thought a pizza joint he grew up around, Monte's, deserved the top spot. The rest is history, but one question lingers: Which pizza brand is Portnoy's 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. During his reviews of Sally's Appiza and John's Pizzeria, Portnoy gave the joints ratings of 9.2 and 9.3 respectively.

Taylor Swift and Travis Kelce's relationship sent the internet into a frenzy when it was first made public. Once the NFL intensified its coverage of the power couple, Dave Portnoy wasn't impressed. Portnoy took to "Varney & Co." to express his disapproval, although he insisted he was a fan of the "Bad Blood" singer. "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."

True to his word, Portnoy has been consistent in supporting Swift. When the singer released "Speak Now (Taylor's Version)" in July 2023, Portnoy said he was bewildered by the singer's musicality in an Instagram review. He 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 whose stage presence could keep her loyal fan base engaged for three hours.

Furthermore, Portnoy's hate list included Kanye West because of the rapper and his ex-wife, Kim Kardashian's feud with Swift. Finally, to stamp his role as a staunch Swiftie, Portnoy made an Eras Tour jacket which traveled from fan to fan during its United States leg. In October 2024, Swift finally acknowledged Portnoy with a personalized note.

Dave Portnoy and his ex-wife, Renee Portnoy, formerly known to Dave's fan base as the "First Lady," walked down the aisle in 2009. Eight years later, Dave announced their split in a January 2017 blog post. "I love her. I will always love her," the entrepreneur 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."

Afterward, Dave's love life only got messier. In 2017, he called out his ex-girlfriend, Jordyn Hamilton, through several tweets for allegedly being unfaithful. Two years later, a sex tape featuring Dave and model Sydney Raines 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 Dave.

Dave's love life took a turn when he began dating Silvana Mojica. After their split, he was linked to Camryn D' Aloia, with whom he attended a Boston Celtics vs. Miami Heat game in April 2024. While Dave has yet to pop the big question again, he's not entirely opposed to a second marriage. He told Adam's Apple in 2021, "I mean, I'm old as s***. So, it's like, I wouldn't be dating somebody if I didn't think there's a chance [to get married]."

Dave Portnoy had a preferred candidate during the 2024 U.S. presidential run, and it clearly wasn't Vice President Kamala Harris. Portnoy, who revealed that he would be voting for ex-POTUS Donald Trump ahead of the polls, had issues with Harris, which he voiced on social media.

The entrepreneur dismissed Harris' campaign message—America's need for change and new leadership—in a video posted to X in October 2024. "She is the worst candidate to ever run for president ever," Portnoy said. "She's like 'We need change. We need this. We need that.' But at the same time, when she's on her media tour ... and she's being asked ... 'Hey Kamala, how are you different from Joe Biden? What will be different, since you are the sitting vice president of the United States now and you're out saying you're the candidate for change?' She cannot answer it."

Safe to say, Portnoy was over the moon when Donald Trump was elected president. In his post-election Instagram analysis of the presidential race, he opined that Trump's win was surreal. Portnoy further disapproved of Harris and her running mate, Tim Walz's campaign strategy and blamed it on the loss of votes, saying, "The Democrats gave us no choice. That was the worst campaign. And their pure arrogance and their moral superiority have driven people away."

Following Dave and Renee Portnoy's separation, the latter moved on with John Clarke, the founder of Broadway Jiu-Jitsu and Fitness in South Boston, Massachusetts. However, as of 2024, Renee and Dave aren't formally divorced. Dave considers Renee his best friend and still shares a joint bank account with her.

"We met when Barstool was nothing. So, you know, she rode the grind up with us," Portnoy disclosed on "The Sage Steele Show." "She has access to, like, all my money. Like, if she just wanted to be, like, 'I'm taking it and gone,' she could." Dave explained their financial arrangement has hindered getting divorced in Massachusetts because Renee was not looking to take half of his fortune.

Portnoy's reported $150 million net worth includes a rich real estate portfolio. In September 2023, the mogul reportedly dropped an astounding $42 million to purchase an island home in Nantucket, Massachusetts, which he gushed over on X, writing, "I went from being able to afford renting for a day to a weekend to a week to a month to renting for the entire summer to buying a house to now buying a house beyond even my wildest imaginations. This is now my view. #DreamBig."

Brianna "Chickenfry" LaPaglia first worked as an intern at Barstool Sports before co-hosting the "BFFs" podcast alongside Dave Portnoy and Josh Richards. She formed such a good friendship with her boss, he even teased her when she was trolled for dating singer Zach Bryan. The couple first crossed paths in May 2023, dated, and called it quits in October 2024. Following the messy breakup, Portnoy and his co-host, Richards, released a diss track aimed at Bryan, titled "Smallest Man." 

On a November 2024 episode of the "BFFs" podcast, Portnoy revealed that he "ended up, like, more in the middle of this" than expected. He was aware that LaPaglia had been asked to sign an alleged $12 million non-disclosure agreement. When Portnoy discovered that LaPaglia's deal was at a standstill because of his diss track, he contacted Bryan's lawyer. He called him out in a text, writing in part, "Pay Bri ASAP, I'm coming for Zach's throat ... pay her or shut the f**k up."

The text prompted Bryan's camp to accuse Portnoy of blackmail, as the entrepreneur shared: "They tried to turn around and say I'm extorting Zach. They're like, 'That's a crime.'" Ultimately, LaPaglia didn't sign the agreement, which was meant to bar her from discussing details about her relationship with Bryan.