Dave Portnoy, the founder and owner of the Barstool Sports media empire, epitomizes today’s digital celebrities. He is charismatically brash, unapologetically self-promoting, a bit rough around the edges, and a genius for generating provocative tweets and videos.
At the same time, Portnoy is a throwback to an earlier age when larger-than-life media moguls shared the same name recognition as the companies they ran. And like many of his industry predecessors, he harvested admirers and detractors.
An Unlikely Entrepreneur
Portnoy snagged an $80,000-a-year sales job after graduating from college in 1999, but quickly grew bored and wanted to run his own company.
In 2003, he launched a Boston sports-focused newspaper, despite having no publishing experience and a too-tight $50,000 start-up budget. His Barstool Sports was a free four-page broadsheet staffed with eager volunteer writers and backed by a few advertisers, including a Jamaican-based gambling website.
Attracting an Audience
Portnoy grew a loyal following among Boston sports fans, and one reader offered to build a free website for him. Dubbing himself “El Presidente,” Portnoy quickly found an online fanbase through opinionated blogging and freewheeling videos that included his reviews of pizza parlors.Barstool’s raw and unpolished style, which included some admittedly sophomoric humor, stood in contrast to the too-serious offerings of legacy sports media. Wacky publicity stunts, such as Portnoy trying to run for mayor of Boston, complemented his media endeavors.
The book’s best segment recalls Barstool’s hilarious disapproval of the four-day suspension of New England Patriots quarterback Tom Brady in the 2015 “Deflategate” scandal. Portnoy and three Barstool colleagues protested the NFL’s punishment of their beloved player by handcuffing themselves to each other and sitting on the lobby floor at the league’s Manhattan headquarters.
Knives Are Out
“Cancel Me If You Can” becomes less rollicking after Portnoy relocates to New York City and is established as a media power player. This opened him to scurrilous personal attacks from rival outlets.He bitterly cites vice reporter Marisa Ingemi’s claim that he denigrated Denna Laing, a National Women’s Hockey League player who was paralyzed during a game. Portnoy states that Barstool Sports supported her by selling merchandise that raised money for her medical care. Portnoy later produced a documentary about Laing, which she loved.
The author angrily recalls two articles from late 2021 and early 2022 by Business Insider accusing him of sexual misconduct with young women.
He blames Business Insider founder Henry Blodget for timing both pieces to disrupt Penn Gaming’s earnings announcements; Blodget was later banned from Wall Street for securities fraud. Penn Gaming purchased a 36 percent stake in Barstool for $163 million in 2020.
“Not only that but somebody had shorted Penn stock both times right before the hit pieces dropped because they had inside information,” he writes. “They knew what was coming and they knew how to profit from it. It appeared that someone may have been up to his old Wall Street tricks again.”
For the record, none of the alleged complaints cited by Business Insider ever resulted in Portnoy being arrested or sued. Portnoy filed a defamation lawsuit against Business Insider, which a judge dismissed; he later dropped the action.
Portnoy provides his take on the highly-publicized brouhaha involving creative difficulties with Alex Cooper and Sofia Franklyn, the hosts of Barstool’s popular women-oriented comedy talk podcast “Call Her Daddy.”
He also details the anxiety involved in buying back his company in 2023 from the private equity firm Chermin Investment Group after selling them a majority stake seven years earlier.
Doing Good Deeds
For all his brashness and tough talk, Portnoy displays a sensitive and altruistic aspect to his personality.He coordinated the fundraising of more than $250,000 for a man who lost a leg in the 2013 Boston Marathon bombing. During the COVID-19 pandemic, his Barstool Fund raised nearly $50 million that was allocated to over 400 small businesses impacted by the pandemic’s disruption.
Portnoy’s philanthropy has also helped veterans and first responders in financial risk, as well as animal rescue endeavors. Perhaps his most unlikely act of generosity involved his wife, Renee. Although the couple divorced in 2017, he states she has free access to his bank accounts because she supported him during his struggling years.
“Cancel Me If You Can” reveals a complex personality who has made life more interesting for many people. Portnoy can be called many things, but “boring” is one word that won’t stick to him or his entertaining new book.
