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In 2003, he left Brentwood and joined Beverly Hills High School, where he graduated the following year.
At the age of eighteen, Flagg started working as a real estate agent.
He began his career under Bruce Nelsons, a real estate broker.
After working in the firm for a while, he later worked for Coldwell Banker East Office.
He went to Brentwood School, a private school in the Brentwood section of Los Angeles.
He pursued his career as a talented real estate broker and served for Coldwell Banker East Office.
During that time, Flagg made various records including Beverley Hills sale & the Brentwood Park, which is the highest sale in the history.
American television personality, Josh Flagg earned fame from the show, Million Dollar Listing Los Angeles which was telecast on the Bravo television network.
He is a well-known real estate agent and author too, so far published two books; A Simple Girl: Stories My Grandmother Told Me and Million Dollar Agent: Brokering the Dream.