I don't know Reggie, but from interviews over the decades, he has always claimed to be very wealthy from his real estate holdings and other investments.
While real estate is down relative to the top of the bubble, its way, way up from the 70's when Reggie got going.
The debt is owed by the company (really, the family of companies): Reggie did not declare bankruptcy.
Also, he did get a salary, and most of us are able to save money from our salaries. Nothing "hidden" there.
While Regions Bank might be a bit hesitant to loan Reggie more money for Fountain Powerboats et al, there is that old saying: "Owe someone a little, its your problem. Owe someone a LOT, and its their problem." So Reggie does have some obvious leverage over the bank at this point. The bank doesn't know how to build boats. What can they do with the plant, equipment, top-of-mind awareness of the brand name? But Reggie can easily make a case that HE can monetize those assets better than anyone.