I don't think he should be worried about squeezing every cent out of his pay per view fights, but simply being smarter with the money he does earn. The Tysons and Flairs could have made twice as much money as they did and they would probably figure out a way to squander it regardless.
Thinking about savings and investing and being around people who won't rip you off, not spending stupidly and acting stupidly (ahem, buying fancy cars and driving recklessly) are signs of being smart. If he was being smart about his future he wouldnt have put himself in a position in which he could be sued into impecuniousness, or simply have been crippled or killed. Thinking prudently isn't about making sure the meat in front of you is as big as it can be, though that can play a part, but about acting wisely on every aspect of your life.
I would have much more respected Jone Jones as a fighter if he simply said the prospect of fighting Machida bored him, instead he clearly showed his reluctance to fighting a man who has given him the most trouble. That being said, its Jones putting his body and health on the line, so its up to him really.