Flagg began working as a real estate agent at the age of 18 when he started making residential sales in high end neighborhoods such as Beverly Hills and the
Sunset Strip. Flagg began his career while still in high school under real estate broker Bruce Nelson with the John Bruce Nelson firm in
Bel Air, followed by a brief stint at the
Coldwell Banker Beverly Hills East office in 2007. Throughout his career as a real estate agent, Flagg has had many record sales, He has also sold homes to various celebrities including
Adam Levine,
Steve Aoki,
Shonda Rhymes and
Tom Ford,
Robert Lamm,
Gavin Palone,
Jody Gerson,
Suzanne Somers,
Justin Mateen,
Matthew Perry. In 2009, he started "Josh Flagg Estates." According to
Forbes, Flagg has sold over $1 billion worth of property during his career.
Million Dollar Listing Los Angeles In 2006, Flagg, along with two other agents,
Madison Hildebrand and
Chad Rogers, were picked to star in a reality TV series following their careers in the real estate industry. They started filming for the show,
Million Dollar Listing Los Angeles, and it aired on
Bravo in August 2006. The show continued with the original cast until Season 4 when
Josh Altman co-starred along with Flagg and Hildebrand. After Season 6 concluded in 2013, Hildebrand left the show, making Flagg the only remaining original cast member. Flagg and Altman were joined by James Harris and David Parnes for Season 7. The series aired its 10th Season in 2017, with Flagg, Harris, Hildebrand and Parnes returning and realtor
Tracy Tutor joining its cast. ==Other activities==