“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 fire for content and comments described as sexist, racist, and offensive.

Portnoy, meanwhile, has an estimated $250 million net worth, including a $95 million real estate portfolio with properties in New York, Massachusetts and Florida.

The path to success starts with years of unglamorous work—just ask Mark Cuban and Sara Blakely

Portnoy’s path to global fame through years of unglamorous work is hardly unique. For many entrepreneurs, the early years look less like success stories and more like stretches of instability, rejection, and unremarkable jobs that quietly shape how they think about risk and reward.

Mark Cuban, for example, has pointed to those kinds of formative years as central to his own trajectory. Before becoming a billionaire investor, Cuban sold trash bags door-to-door as a kid and later worked in tech sales after graduating from Indiana University. He shared a cramped apartment in Dallas with five other men, sleeping on the floor when no bed was available.

“It was nasty as can be,” Cuban told the San Francisco Standard’s Life in Seven Songs podcast. “I slept on the floor, and if somebody was out of town, I got a bed. I didn’t have my own closet, didn’t have my own drawers. Nothing.”

That stretch of scrappy living eventually led Cuban to start MicroSolutions, a software company he sold for $6 million in 1990—his first major exit on the way to becoming a billionaire investor.

Sara Blakely followed a similarly nonlinear path. Before founding Spanx, she spent years selling fax machines door-to-door, a job she has credit with teaching her resilience in the face of constant rejection. With $5,000 in savings and no outside investors, she eventually built Spanx into a company now valued in the billions.

Blakely has said the hardest part of starting something new is protecting it in its earliest stages, when doubt comes from every direction.

“In today’s world, ideas are the most vulnerable in the moment you have them,” she said.

For Jake Miller, now the founder and CEO of coffee and kitchenware brand Fellow, entrepreneurship began with small, scrappy bets long before retail success. As a teenager, he sold T-shirts and bootleg CDs to make money, later facing repeated rejection as he tried to break into the crowded coffee industry and build a multimillion-dollar business.

“Nothing was going to stop me,” Miller told Fortune last year. “Each no was simply one step closer to the eventual yes, and if it would have only been no’s, like, I would have figured out how to sell a kidney.”

For many founders, the odds are long and the path uncertain—but persistence is often what separates the breakthrough stories from the rest.