The 30 for 30 documentary on how many athletes fall into bankruptcy and financial distress convinced me that no one is immune.
That said, Bryan has a solid head on his shoulders, seems to enjoy a modest lifestyle, and, most importantly, it's not like he can't work.
Based on Monday night, we know he still has enormous earning potential with the WWE alone, so it's not like that spigot will get shut off anytime soon. How many would eat up a storyline where DB emerges to reignite the RAW GM who somehow comes to power and acts as a check on the authority?
Will things be more difficult with his retirement? Certainly. But, he has plenty of opportunities be they within or without the industry that will allow him to generate income. Given Brie's similar earning power, they'll be fine.