The flip side of this is "How long was Winthorpe homeless and destitute?" From looking at the movie it looks like a couple of days,but that's hardly enough time for Billy Ray to build a reputation ...
In episode 6 of Unbreakable Kimmy there is a scene where the rich daughter's friends are sat around a fountain (at about 18:30 into the episode) and a girl says 'and she stepped on the ball' ...
Near the end of Trading Places, Winthorpe and Valentine concoct a plan to get back at the Dukes while making themselves rich. I understand they used insider trading; but what exactly is Billy Ray ...