5. Stan Lee
Everyone must have heard of Stan Lee, especially if you are a fan of superhero movies and comic books. Lee is known as the co-creator of The X-Men, Spider-Man, The Fantastic Four, and The Incredible Hulk. However, his superheroes as well as his creativity were not able to save him from bankruptcy. Lee started an organization that mainly dealt in Internet comic books. Unfortunately, the person with whom he ran this company was accused of security frauds and scams. The organization exhausted its entire capital pretty quickly and his professional partner escaped from the nation. Then, it was the dot-com bust. His own organization, Stan Lee Media, also fell apart.