Paris Hilton

The heiress and entrepreneur were born into quite the family fortune—her great-grandfather is Conrad Hilton, also known as the founder of the Hilton Hotel chain. However, Paris Hilton did not solely rely on her family’s wealth in order to get by. As audiences, we were first introduced to the socialite through reality-TV.

Despite her rather controversial rise to fame, few can deny the fact that Hilton is a talented businesswoman. Her investment planning has led to a lucrative licensing empire. Her businesses range from clothing, perfume, handbags, and many more. Not bad for someone who got expelled from boarding school!