Immediately after finishing high school from Beverly Hills High School in 2004, Josh Flagg immediately went to work, negotiating in the high-end residential real estate market. Josh Flagg is best known for appearing on the Bravo reality show Million Dollar Listing, which follows young players in the high-end real estate business. He chose the industry over his family business, and within his first four years in the job, he made four record sales: the highest sale in the history of Brentwood Park and the highest sales on the exclusive Roxbury Foothill and Onovale Drive. More than these, Josh is known for pampering clients, sending them up in helicopters to view properties. He is also on the board of the Friends a Greystone, a non-profit organization that donates time and money to the restoration of Greystone Mansion in Beverly Hills.