The guys at barstool who have been there for 10-15 years and were part of the Chernin Group/PENN acquisitions became rich once their shares vested. Big Cat was on a podcast called Failing Upwards a few years ago, and one question they would ask in a half joking/half serious manor was "How much money do you make?"
This was in 2018/2019, and Big Cat said he was wealthy "on paper", because it was a lot of stock options that had not materialized. This goes for Hank, Feitelberg, KFC, and a few others.