David Portnoy

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. 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. The site made headlines in January 2020 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. Portnoy has trended on social media for his antics during coronavirus, including his profanity-laced rants while day trading. He 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.