There was a great story in the NY Times about the craziness around taxi medallions in New York - the things that let you own a cab - and some of the trouble it got drivers into. The medallion system among NYC taxis put a sharp divide between those who drove taxis and who owned them, which lead to people making some bad decisions to get on the other side of that line, aided by intermediaries who were neither buyers or sellers, but profited off the transaction. The ridehailing apps came along and basically removed the barrier, but the scheme was so shaky it was destined to fail.