Cancel Me If You Can

Dave Portnoy's memoir traces his two-decade journey from hawking newspapers on the streets of Boston to building Barstool Sports into one of the most recognizable, and polarizing, media brands in America. Written in Portnoy's brash, unfiltered voice, the book chronicles every major milestone, controversy, and business deal that shaped the company he founded in 2003, sold twice, and ultimately bought back for one dollar.

After graduating from the University of Michigan in 1999, Portnoy took a sales job at a Boston firm called Yankee Group. He earned $80,000 a year but found the work unfulfilling. Living with five high school friends in an Allston-Brighton apartment, he spent his evenings brainstorming business ideas. A cold call to an offshore sportsbook called BetJamaica provided an unexpected opening: They agreed to advertise in a gambling newspaper if Portnoy started one. With $50,000 in startup capital, split between personal savings and a loan from his father, he founded Barstool Sports. He chose the name because the URL was available and it captured the tone he wanted: regular guys talking sports at a bar.

Portnoy had no journalism training and no knowledge of newspaper production. He bought a hundred newsracks, a used Astrovan, and cold-called advertisers before the paper even existed. A freelance graphic designer named Erin Boyce rescued the operation when a last-minute meeting with his printer revealed Portnoy did not know how to format content for print. The first issue on August 27, 2003, was distributed by homeless workers from a staffing agency, roughly 90 percent of whom failed to show up. For the second issue, Portnoy hired attractive models to hand out papers at subway stations, and every copy was taken. Among those models was Renee, a Boston University student who told him his business would fail. She later became his wife, known to fans as "The First Lady."

With a biweekly break-even cost of $3,400, Portnoy sustained the paper through relentless sales calls, fake ad aliases to make the operation look larger, and selling leftover T-shirts. He recruited three unpaid writers, Pete Manzo, Jamie Chisholm, and Jerry Thornton, who formed the original writing staff. Viral reader submissions and a tradition of featuring local women as cover models broadened Barstool's appeal beyond sports. Revenue remained thin, and Portnoy and Renee moved in with her mother to save money.

The company's transformation began when a reader named Ian White, about to relocate to New York, offered to build a free website so he could keep reading Barstool. Portnoy shifted from biweekly print editions to writing ten to fifteen blogs per day, eliminating geographic limits on readership. Features like "Local Smokeshow of the Day," a daily post highlighting an attractive local woman with her permission, became hugely popular. New revenue streams emerged through automated online ads and an expanding T-shirt business tied to viral moments.

Portnoy hired his first full-time employee, Paul "Gaz" Gulczynski, Renee's childhood friend, who eventually became head of social media. Jenna Mourey, later known as Jenna Marbles, went massively viral on YouTube in 2010 and became one of the platform's first megastars before departing, teaching Portnoy to hire talented people and let them create freely. He expanded to New York by hiring Kevin Clancy (KFC) and Keith Markovich (KMarko), who split a single $50,000 salary. Dan Katz (Big Cat), a regular caller on Portnoy's radio show, took over the Chicago site, forming a new core team alongside Portnoy, KFC, and KMarko.

A 2010 college music tour called Stoolapalooza proved Barstool's campus reach when three thousand tickets at UMass sold in under a minute. This momentum fueled the Blackout Tour, an EDM-style party series with blacklights and CO2 cannons that began in frat basements and scaled to larger venues and festivals, clearing roughly $200,000 per night at its peak before regulatory problems forced its end. Controversy followed: A group of college women called KO Barstool organized protests, surfacing a 2010 blog in which Portnoy had written a crude joke about skinny jeans and rape. Portnoy refused to apologize, establishing a combative pattern he maintained for years. A separate blog joking about a photo of Patriots quarterback Tom Brady's toddler triggered state police involvement and a Boston radio firestorm before the Massachusetts attorney general determined no laws were broken.

Barstool's fortunes became intertwined with Boston's unprecedented sports dynasty, as the city's teams won thirteen major championships between 2001 and 2024. The company's real-time coverage of the 2013 Boston Marathon bombing cemented its role in the city's culture, and Portnoy raised $250,000 for marathon survivors through T-shirt sales. After the NFL suspended Brady over the Deflategate scandal, in which the league alleged he had deliberately used underinflated footballs, Portnoy and three employees handcuffed themselves together in the lobby of NFL headquarters, were arrested, and spent a night in jail. Portnoy distributed sixty thousand Goodell Clown Nose towels at the Patriots' home opener, and Brady later acknowledged the protest during his Hall of Fame induction speech.

In 2016, the Chernin Group, a media investment firm, acquired 51 percent of Barstool for $12.5 million. Portnoy used the investment to move the operation to New York City and hire Erika Nardini as CEO. The New York era produced an explosion of content and talent but also intensified media attacks. A podcast called Pardon My Take, hosted by Big Cat and new hire PFT Commenter (Eric Sollenberger), rocketed to the top of the iTunes charts but created internal tension as its hosts sought distance from Barstool's controversial brand. The Call Her Daddy podcast, launched in 2018 by Alex Cooper and Sofia Franklyn, became Barstool's fastest-growing property before a bitter 2020 contract dispute split the cohosts. Cooper returned solo, honored her contract, and departed for a $60 million Spotify deal.

In 2020, Portnoy engineered the sale of Barstool to Penn Gaming, a regional casino operator, for a total valuation of $650 million. COVID became the backdrop for some of his most popular content, including Davey Daytrader Global, a daily stock-trading livestream, and the Barstool Fund, which raised nearly $50 million to save over four hundred small businesses. A July 2020 interview with President Trump at the White House went viral but caused internal friction, as Big Cat feared it implied all of Barstool endorsed the president.

The Penn partnership deteriorated as Barstool's brand created persistent regulatory problems in the sports gambling industry. A leaked sex tape dropped Penn stock 5 percent, and two Business Insider articles alleging violent sexual encounters, which Portnoy calls fabricated and traces to former Call Her Daddy associates, caused a roughly 20 percent decline. Employee Ben "Mintzy" Mintz's accidental use of a racial slur on a livestream prompted Penn to demand his termination, a decision Portnoy publicly opposed but could not override. In 2023, Penn CEO Jay Snowden informed Portnoy that Penn had brokered a deal with ESPN, but Disney's nonnegotiable condition was that Portnoy could not be involved in any form. Portnoy refused to leave and negotiated to buy the entire company back for one dollar, accepting its $12 million annual losses in exchange for full ownership. ESPN Bet subsequently underperformed, and Penn exercised its exit clause by the end of 2025.

In the epilogue, Portnoy notes that Nardini departed amicably after the buyback and Big Cat assumed a day-to-day leadership role. Portnoy's first acts as sole owner were rehiring Mintzy and making the company profitable. Approaching fifty, he splits time between the Florida Keys and Nantucket, framing the full arc as a story no screenwriter could improve and closing with the refrain that has defined his career: "You don't cancel me; I cancel you" (297).