I think there is a misconception about being "poor" post-skateboarding. If some pro retires from skateboarding and spent the last 10-20 years of their lives flying around the world playing skateboards and owns a home, but has to go work at Wendy's to keep that home and afford to do basic things, they're doing better than most of us.
I have to earn money and work at a company known for overworking its employees to afford the necessities and a few luxuries, if a former pro can work some bullshit job and easily afford nice necessities they won the race.
For example, if a couple's take home pay is 4K a month but rent is $2,500 that only leaves them with $1,500 disposable income. If some pro has a paid off house and has to pay $500 a month in upkeep and tax, but "only" earns 2K a month, they're doing just as good as the couple making twice as much.
In case you're serious, or otherwise are JRog himself, here's how I know he's broke:
A few months after retirement, Ford Motor Credit Company sued to recover losses from his Aston Martin. The amount owed was in excess of $25k so he clearly had not made payments for some time and had no savings to cover it. The sheriff was unable to collect on the judgment, so there were no wages to garnish, no savings to raid, and no property or assets to seize.
If there's any benefit to being poor, they can't take what you don't have.
a gnar for the detective work. Are there sources to back this up?