In Rocky V (1990), Okay his attorney screwed him over but he could have written an autobiography even if he didn't want to do that because of being ashamed of his past or maybe he was a private person, became a fight commentator or even do commercial's we seen in Rocky 3 he was doing plenty of them, he could even have done cameos in a few films. Sure they might have had to move into a smaller home but in reality there was ways where he didn't need to end up back where he started.