Jay pursued endorsements and set up tons of small revenue streams as soon as he hit the scene.
If you don't fall asleep during his videos you'll see how he constantly talks about business tidings all day long. He's the most business oriented bodybuilder ever. He's the smartest financially by leaps and bounds. He knows the "sport" has no money and that the small pittens are short lived. He's probably making just as much money as ever with his shitty new supplement line.
Jay is a lot better bodybuilder and money manager then 99% of all pros in the history of BB.
BUT, he isn't insulated from every financial pitfall.
1. The Vegas real estate market crashed badly and his home has lost aprox 40% of it's value since 2007. That hurts.
2. He had an equitable divorce with no kids, but they still had to split some of the assets.
3. His supplement line launch appeared to flop. But , ARNOLD's new line didn't seem to do that well either.
Ironically, his 3-4 NPC Jay Cutler classic contests that he promotes seem to be doing quite well.
A smart , regional promoter can clear 20-30 k, per event IF they get 300 or more entrants and know how the market the thing.
I suspect he can meet his basic living expenses off his show promotion alone.
Then, he ahs a variety of other ventures to make a few bucks off.