The media magnate, who has an estimated net worth of $118 million, turned his love of sports (and sports betting) into a business venture after striking out on a college athletic career. He grew up in Massachusetts playing baseball and football, and now his sports and pop culture blog is a moneymaker that's branched out to podcasts, videos and merchandise.
Portnoy, 43, started Barstool Sports when he noticed there was a void in the market for analysis to inform his sports betting in the 2000s. It was the early days of the internet, but Portnoy opted to make Barstool Sports a local Boston paper, not the website it is today. Portnoy wrote the first issues himself and passed them out to commuters taking the T.
“I always wanted to do my own thing,” he said in a Barstool Sports profile. “I don’t know why; that was just how my brain worked. I always wanted to start my own business.”
He began finding writers to fill out the paper, including his childhood friend Todd McShay, who's now an ESPN commentator.
Bartstool Sports went digital around 2008, although Portnoy continued to distribute print issues until 2013. As the website's audience grew, so did Barstool's value, especially as Portnoy placed emphasis on creating personalities at Barstool.
“We were always early to things,” Portnoy said in the profile. “When I started doing this, you could write a story, and there was no real rush. As time went on, it became a competitive industry and other blogs would write the same stories as us. Everyone could have a similar take on something on the internet. But nobody – and still to this day – nobody has the personalities that we have here.”
The site made headlines in January when it reached an agreement to sell a 36 percent stake to Penn National Gaming Inc. for about $163 million. Media company The Chernin Group owns a 36 percent stake in Barstool Sports and the rest is controlled by Portnoy, Barstool Sports CEO Erika Nardini and employees.
“I'm trading my own money and lots of it,” Portnoy told FOX Business' Jonathan Garber. “I'm having fun. As long as we're still kind of with nothing else to do, I'll keep day trading.”