© Michele Eve Sandberg/Corbis
The investment: While figure skater Dorothy Hamill became America's sweetheart by winning a gold medal at the 1976 Olympics, it was the "Ice Capades" that made her rich, giving her the first $1-million-per-year contract ever given to an American female athlete.
So when the company went bankrupt in the early '90s, it was only logical that Hamill try to save the veteran institution. Along with her husband at the time and another investor, Hamill purchased the "Ice Capades" in 1993 for an undisclosed sum.
The dive: Ironically, Hamill had contributed to a change in how the public perceived ice skating, emphasizing the sport's intensity and athleticism. As such, the frivolity of the cartoonish "Ice Capades" no longer held widespread appeal. Hamill unloaded the "Ice Capades" in 1995 and filed for bankruptcy the following year, telling one press outlet, "money is evil." The skating star has since put her talents to work in a stint on "Dancing With the Stars" and no doubt hopes her New York Times best-selling book, "A Skating Life," as well as her eponymous figure skating fantasy camps, will continue to bring in revenue.