Dave Portnoy wants Barstool Sports to run like Saturday Night Live

Dave Portnoy wants Barstool Sports to operate more like Saturday Night Live, with the company bigger than any single personality and a rotating cast of voices under one roof. That shift is about more than style. It is a bid to turn a creator-led media brand into something scalable without letting any one volatile star define its value.

Portnoy started Barstool in 2003 after leaving Yankee Group in Boston, where he had been earning about $80,000 a year. He has said he began with about $30,000 in savings and a $20,000 loan from his father, then launched a free four-page sports newspaper that he handed out on Boston subway platforms and street corners. Early editions later showed up around Boston T stops, Fenway Park and the Garden, a grind-it-out distribution strategy that helped build a following long before Barstool became a digital brand.

The company grew from those print roots into a nationally recognized digital media business built on sports, pop culture and personality-driven content. Portnoy has long described Barstool as a place for misfits and outspoken voices, and that formula helped the brand scale fast. It also created the central problem he is now confronting: when the personalities are the product, the brand can rise with them and be dragged down by them.

That tension sharpened in 2023, when PENN Entertainment completed its acquisition of Barstool Sports in February. Later that year, Portnoy bought Barstool back for $1 after PENN said the brand created conflicts with its regulated gambling business. The sale and repurchase underscored how difficult it can be for a creator-led company to fit inside a larger corporate structure when its identity depends on controversy, loyalty and the independence of its on-air talent.

Portnoy’s new memoir, Cancel Me If You Can, revisits those origins and his view of how he built the company against doubters. It also fits the logic behind his SNL comparison: keep the brand larger than the individual stars, keep the lineup changing, and make the machine outlive the people inside it.