Dave Portnoy quit an $80K sales job to start Barstool—he hand-delivered papers in a secondhand van while living with his girlfriend’s mom for 6 years

Before Dave Portnoy was running Barstool Sports, stirring the pot on social media, or even reviewing pizza slices—he was just another recent college graduate with no clear career path. “I was essentially like every other white middle-class dude in the world with a liberal arts degree,” he described in a new book, Cancel Me If You Can. “I had no real skills.” After graduating in 1999, Portnoy moved to Boston and landed a sales job at Yankee Group, a technology research and consulting firm, earning about $80,000 a year—a cushy salary at the time that offered stability, if not much excitement. His two main interests—sports and gambling—were calling, and he decided to walk away from his 9-to-5 to launch Barstool as a free Boston sports newspaper. It was a gamble that initially looked anything but lucrative, with the early years being a constant grind. Portnoy personally delivered newspapers in a secondhand van, occasionally cleaned dog waste out of his newspaper boxes, and, six years after launching the business, was still living with his girlfriend’s mother while trying to make ends meet, according to The Wall Street Journal. “No vacation days. No nothing for probably about a decade. It was a grind,” he told Bloomberg Radio’s Masters in Business podcast. “It was delivering newspaper, writing the newspaper, selling ads, pretty much a one-man show.” But sticking with his dream, even when times were tough, helped Portnoy meet the moment with the shift to digital. Over the last decade, the company has rapidly expanded into social media, blogs, podcasts, merchandise, sports betting, and even consumer products—and become a hit especially among young audiences. It also became the original home of the hit podcast Call Her Daddy, hosted by Alex Cooper, before she departed and later signed a deal with Spotify for over $60 million. Barstool was valued at $606 million in 2023, but its time has not been without controversy. The company and Portnoy have repeatedly come under f