The Houses That Entrepreneurship Built

Shane Reilly, San Francisco
1 of 18

Peter Thiel, Co-Founder of PayPal

Locations: Homes in Maui, San Francisco (pictured here), and (rumored) Los Angeles

Prices, combined: $50 million

Maui mansion: Thiel purchased a home in Maui for $27 million--the most expensive real-estate sale recorded in the Hawaiian island's history.

Peter Thiel, the billionaire co-founder of PayPal and early Facebook investor, seems to be on a bit of a real-estate spending spree these days.

(Continued on next page.)