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.

Natali had some trouble choosing her worst, as she’s had so many challenges. One story she can’t really talk about because it is the subject of an active FBI investigation into some funds that were in her IRA. This investment was particularly heartbreaking because she had her children’s investments tied up in that situation, as well hers and her husband’s.

In 2016, Venkatesh acquired what he thought would be a good long-term investment – and the company’s profile showed it had good potential based on its statistics and then-current standing. It was a large, generic-pharmaceutical manufacturer, one of the top three in India and 20th in the world.