The Houses That Entrepreneurship Built

Dupont Group Listing
5 of 18

Jack Dorsey, Co-Founder of Twitter & Square

Location: San Francisco's Seacliff neighborhood

Price: $10 million

An unwanted abode?: The home was listed and withdrawn 17 times without selling since 1998.

Jack Dorsey, the design-obsessed founder of Square, purchased the two bedroom home with a view of the South Bay and the Golden Gate Bridge in 2012 for $10 million--making it the most expensive two-bedroom home in Seacliff. According to Curbed SF, Dorsey had plenty of work cut out for him when designing the new interior. "Inside, well, a bad moment from the 'eighties," the blog noted. "It doesn't look like anyone's had a really good time there in a while."