Josh Flagg

Vice President, Flagg Family Capital

Broker, Compass

Josh Flagg has a waterproof notepad in his shower. With the “Million Dollar Listing Los Angeles” agent juggling multiple businesses, it helps to be able to jot down a thought wherever one might strike him. 

Keeping busy is just the way he likes it. “I love working. I don’t know what I would do if I didn’t work. I’d be bored out of my mind,” he told TRD in 2025. While Flagg, who grew up in Los Angeles, is known to many from the reality TV show and his high-end residential business locally, his latest challenge is taking the lead on his family’s commercial real estate business, Flagg Family Capital. He’s steering a ship now that’s long focused on a portfolio of shopping centers, offices and high-end commercial and residential buildings in markets such as New York, Miami and Palm Beach. 

Even with the family business, a growing real estate platform in Estate Media and other consumer-facing investments, Flagg still loves residential real estate. Although Flagg’s 2024 exit from Douglas Elliman was reportedly contentious, he appears to have navigated away from any controversy while at Compass. In 2025, he sold the Gloria Vanderbilt Estate in the Beverly Hills Flats for $16.1 million. He also co-listed, along with Josh Altman, 1501 Tower Grove in Beverly Hills, which sold in August for $16.5 million and was the home of “Real Housewives of Orange County” stars Heather and Terry Dubrow.

 — Kari Hamanaka