Douglas says his story was not as much a terrible investment as it was memorable. It was 1988 and he was in his late 20s and a bond trader for a mid-sized US bank. He sat on a desk with other bond traders, and bought and sold United States Treasury securities during the trading day hoping to speculate on price movements, which are relatively random on any given day.

This is the story is of an error made by a financial professional that Darryl was advising, so this is someone who should have known better. Darryl was based in Tokyo, dealing with the expat community there and many of his clients were also financial professionals.

Jason’s worst as far as amount of money lost was on a property in Memorial, Houston, one of the last houses that he and his team ever invested in during their flipping operations. It was a beautiful 3,000-square-foot 60-year-old house and it needed complete refurbishing, which they had just finished doing.

Scott invested in distressed home loans in Chicago with a group of investors. The deal went south, legal proceedings took much longer than he expected, especially for out-of-state buyers of the distressed debt. Eventually, he bought out his investors and worked to close the deal, but in the end he lost about US$250,000.

In around 2001, while Shaun was a 23-year-old a graduate student at Harvard University, he was putting some thought to the big question: “What am I going to do with my career?” What he did know was he never wanted to go the corporate route and work somewhere like McKinsey or Goldman Sachs, even though most of his classmates were headed in that direction.