Dave Portnoy has had a lot of success — and some bumps in the road — when building his financial empire.
Portnoy founded Barstool Sports in 2003 as a weekly print publication. One year after forming the company, Portnoy filed for bankruptcy protection in 2004 after large gambling losses, per The New York Times.
Years later, Barstool Sports expanded online and ceased its print operation in 2010. After focusing primarily on the digital aspect, Portnoy saw…
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