“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.”
