28. Rihanna

Rihanna used to sell hats and clothes on the streets of Barbados. Her family came from humble beginnings and when she was a child her father sold clothes from the trunk of his car on the street. She quickly learned the ropes and began setting up her own rack, selling anything from hats to belts to even scarves.

She also used to package up candy that she bought on her own and sell them at her school for more than she paid. It wasn’t until years later that she would sign with Jay Z and Def Jam records. The rest is history.