Dave Portnoy’s Barstool start began with paper routes and a used van

Dave Portnoy gave up an $80,000-a-year sales job after college to build what became Barstool Sports, Fortune reported. The decision matters because the company later grew into a major digital media brand, even as Portnoy and Barstool drew repeated criticism over offensive content and comments.

Portnoy graduated in 1999 and moved to Boston, where he worked in sales at Yankee Group, a technology research and consulting firm, according to Fortune. In his book Cancel Me If You Can, excerpted by The Free Press, Portnoy described himself as a liberal arts graduate without obvious professional skills.

Fortune reported that Portnoy’s main interests were sports and gambling, and that he left the steady job to start Barstool as a free sports newspaper in Boston. The early version of the business required Portnoy to handle much of the operation himself.

The Wall Street Journal reported that Portnoy delivered the papers in a secondhand van and at times cleaned dog waste from newspaper boxes. The Journal also reported that six years after starting Barstool, he was still living with his girlfriend’s mother while trying to keep the business going.

Portnoy described the workload in a 2020 interview on Bloomberg Radio’s Masters in Business podcast, saying he went years without vacations while writing the paper, delivering it and selling ads. He characterized Barstool’s early period as a one-person operation built through repetition and long hours.

From local paper to digital media brand

Fortune reported that Barstool expanded over the past decade into social media, blogs, podcasts, merchandise, sports betting and consumer products. The company gained a strong following among younger audiences, according to Fortune.

Barstool also served as the first home of Call Her Daddy, the podcast hosted by Alex Cooper, Fortune reported. Cooper later left and signed a Spotify deal worth more than $60 million, according to Variety.

CNBC reported that Barstool was valued at $606 million in 2023. Celebrity Net Worth estimates Portnoy’s personal fortune at $250 million, while The Wall Street Journal has reported that his real estate holdings include properties in New York, Massachusetts and Florida worth $95 million.

Barstool’s rise has also brought scrutiny. The New York Times has reported that the company and Portnoy have faced repeated criticism for material and remarks described as sexist, racist and offensive.

Other founders had rough starts

Fortune compared Portnoy’s early work to the beginnings of other entrepreneurs, including Mark Cuban and Sara Blakely. Cuban has said he sold trash bags door to door as a child and later worked in technology sales after college, according to Fortune.

Cuban told the San Francisco Standard’s Life in Seven Songs podcast that he once shared a crowded Dallas apartment with five other men and slept on the floor when no bed was available. Fortune reported that Cuban later founded MicroSolutions and sold it for $6 million in 1990.

Blakely spent years selling fax machines door to door before founding Spanx, according to Fortune. Fortune reported that she started the company with $5,000 in savings and no outside investors, and that Spanx is now valued in the billions.

Fortune also cited Jake Miller, founder and CEO of Fellow, who sold T-shirts and bootleg CDs as a teenager before building the coffee and kitchenware brand. Miller told Fortune that repeated rejection in the coffee industry did not stop him from pressing ahead.

This story draws on original reporting from Fortune.