My theory is that after losing all his money thanks to Bernie Madoff he had to consider going back to work. At his age though he had few options except perhaps Wal Mart greeter, crossing guard, or night watchmen at some strip mall driving a golf cart.
He defiantly said 'fuck that bullshit' and then went out looking for something that might take his mind off his problems and have some fun in the process.
This is what he came up with and it quite obviously was a good decision.