From Mental Floss:
Starting a legitimate business is hard, boring work. There’s paperwork to fill out, employees to hire, and all sorts of other drudgery, not to mention the biggest hurdle of all: providing a product or service for which customers are willing to pay. In all likelihood, it would be much easier to just stumble upon some clever scam to line your pockets. Or so it would seem. As many aspiring scam artists quickly learn, when a business scam fails, it tends to fail in rather grand fashion. Just ask any of these four teams of not-so-smooth operators.
A Corny Sea Story
Xenothemis and Hegestratos may not have been the world’s first white-collar criminals, but they were certainly noteworthy for their incompetence. In 360 B.C, the pair stumbled upon what seemed like a killer plan to make some quick cash. Shipping was extremely risky at the time, and boats went down at sea with alarming frequency. To exploit this uncertainty, Xenothemis and Hegestratos devised a plan in which they would receive a cash advance to ship a load of corn from Syracuse to Athens. Due to the dangers associated with shipping, the buyer would take on full risk if the shipment didn’t make it to Athens, so if the boat sank Xenothemis and Hegestratos could keep their cash.