Honestly, I can't see Jeff as a successful prostitute. I can't imagine him being customer oriented.
But, I can see him as a really bitchy man-pimp.
Once Donny runs out of the $157 he gets for his assorted rusted rubbish that he calls his truck, boats and jet skis, I can see Jeffy Jay working him hard on the streets of Whereeverthefuck, Nevada and taking "the oranges" to him for holding out on the extra cash he got for swallowing.