Jack Dorsey – $21.9 Million, San Francisco

Jack Dorsey is among the four founders of one of the world’s largest Social Media platforms—Twitter. While the said social networking site made Dorsey billions of dollars richer, he didn’t stop there. He also went on to create a mobile payments company named Square.

The now 43-year-old spent an inkling of his money on a 3,588-square-foot mansion in San Francisco. It was not just any house, but one that belonged to his neighbor. Built back in 1962, the $21.9 million residence holds five bedrooms and three bathrooms. Since it sits on top of a cliff, the house is exclusive and allows some breathtaking views of the ocean.