Post by @theventure

Buying Barstool back for $1 came with a catch. Penn handed Dave Portnoy 100% of the company in August 2023 in return for promises that he wouldn't compete with it, and kept the right to half the gross proceeds if he ever sells Barstool again. Penn booked a loss of $800 million to $850 million on the way out. Portnoy's answer was that there will never be a sale to split. "I am NEVER going to sell Barstool Sports," he wrote. "I'II hold it 'til I die." Barstool was the thing he had given up a steady job for. He quit an $80,000 sales job to start it in 2003, with $30,000 of his own savings and a $20,000 loan from his dad. For the next six years he lived with his girlfriend's mother and drove the papers round Boston in a secondhand van. Follow @theventure for the greatest founder stories ever told!