Him working for an employer stopped around the time Hanky Sr passed away. He probably got his inheritance, quit working and started living the rock star life whilst managed his own accounts (inheritance)
He must have blown up his accounts though making risky trades and chasing loses, which is also probably why his ex wife accuses him of being a gambling addict.
Lost most of his money/inheritance so now he's back on the 9 to5 grind out of necessity.
Yes clearly 2010 was a turning point, inheritance makes sense on that front
Got lucky with the timing as well given the extended post-GFC bull market, so a tailwind extension on the $ before recently
That being said, recent financial circumstances necessitating a return to work may be for the best, a Mr Toad existence doesn't nourish the soul long term