David Portnoy made his money as the creator of Barstool Sports, a digital sports empire.

Over the course of two trades, he sold pieces of Barstool. In 2016, he sold a majority share to The Chernin Group for the first time.

Penn Gaming paid $163 million to the founders for a 36 percent ownership in the company in January 2020.

Penn National Acquisition

Penn National Gaming purchased a 36 percent share in Barstool Sports for $450 million in January 2020.

Penn National has the option to pay an extra $62 million over the next three years to increase its ownership to 50%.

Stock Holdings

According to a Penn Gaming 10-Q SEC report for the first quarter of 2020, of the $163 million in cash.

A total of $23 million in convertible preferred shares was distributed, with $3 million set aside for "forward arrangements."

Penn Gaming has a market capitalization of $10 billion as of this writing. At such price, a 0.5 percent ownership would be worth $50 million.

Dave is said to possess 1/3 of that stock, which is worth roughly $16 million today, and he has an estimated net worth of $80 million.