Was it just entertainment though? I recall hearing years ago that he was making a not-insignificant amount of money via EVE, whether through legitimate (e.g. themittani.com news site) or illegitimate (e.g. selling ISK or supercaps) means.
He was previously a DC lawyer who FIREed and moved out to WI. I think he made a little money but I don’t think it was anything other than toy money.
"Yeah, being an attorney wasn't cut throat enough so I decided to become a Space Pirate King..."