Last December, a cameraman shadowed Josh Flagg as he wandered about his most recent purchase, a Mid-Century Modern home.
It was the early afternoon and the Compass agent had been up since about 7:30 a.m. He’d had social calls with a few famous friends, plus a steady stream of Zooms about: the latest real estate acquisition by his family’s business, an event he was hosting, his two-year-old real estate media firm and a bagel venture he’d helped finance. Then, Flagg drove himself (he typically has a driver) to Beverly Hills to meet with the jeweler designing a pin for his tuxedo. Capping a day with no real downtime, he was off to look at plans for another house he owns on Bedford Drive.
“I love it that way,” Flagg said. “I can sleep when I’m dead.”
That he shared the busy day with a reporter and a tour of his home with the 3 million followers across his Estate Media’s social channels can help explain what propelled Flagg onto a stage well beyond real estate.
He spent 15 seasons on “Million Dollar Listing Los Angeles,” where fans liked him as the Beverly Hills agent with a quick wit, exacting taste and encyclopedic knowledge of Los Angeles’ most historically significant homes. The renown yielded opportunities beyond real estate — the events, the media company, the friendships with locals like Candy Spelling and Melissa Rivers.
But with the show now on pause, Flagg is ramping up his run at the helm of his family’s business, Flagg Family Capital, a commercial real estate portfolio built by his parents and grandparents. His next act is upon him: proving he can carry on the legacy and expand into luxury markets.
Yet he comes to the job with baggage. Within the industry, he is a polarizing figure. Some scoff he’s just another reality TV celebrity who can hardly be considered a market leader when it comes to selling high-end real estate. There’s also the matter of the made-for-TV drama that’s followed Flagg over the years: arrested for allegedly stealing art from clients (the issue was reportedly dropped due to lack of evidence), leaving Douglas Elliman on contentious grounds and accusing his former boss in a lawsuit of hacking his computer (the suit later dropped the executive as a defendant in July).
The spotlight has also captured moments such as Flagg’s marriage to Bobby Boyd and their divorce in 2023.
Though he has lived so much in the public eye, Flagg still seeks to guard his image. The slightest whiff of controversy can spark a swift demand letter, such as the one threatening a defamation suit sent to The Real Deal by Flagg’s attorney in relation to a mention of the alleged 2008 art theft.
“Within days of the allegations being made against my client in 2008, the Los Angeles District Attorney determined that it would not pursue any charges against my client,” the letter said.
Still, it’s hard to deny that Flagg, already a well-connected Angeleno, saw an early opportunity in reality TV, and leveraged it into a career that’s made him a household name with a long business runway.
“One could look down on reality television but at the end of the day, my highest-net-worth clients watch [“Million Dollar Listing”],” he said. “You go on American Airlines or Delta, it’s on the plane. It’s not a reality show that’s drama-based with housewives throwing wineglasses in people’s faces. Everyone loves high-end houses, and everyone likes real estate porn and Los Angeles properties.”
While Flagg is not at the top of the heap in sales volume-based rankings, such as TRD’s annual list, his name is often heard in connection with local trophy properties.
He was one of the listing agents on Casa Encantada at 10644 Bellagio Road, which was at one time asking $250 million before going off and on the market at reduced pricing. Earlier this year, he sold the Gloria Vanderbilt Estate in the Beverly Hills Flats for $16.1 million. He co-listed with Douglas Elliman’s Matt Altman, his former “Million Dollar Listing Los Angeles” co-star, the Beverly Hills home of “Real Housewives of Orange County” cast members Heather and Terry Dubrow. The property, at 1501 Tower Grove, sold for $16.5 million. Last month he nabbed the listing for 1436 Bella Drive, known as Falcon Lair which was originally built and owned by silent film actor Rudolph Valentino and later home to tobacco heiress Doris Duke.
Family business
For all the high-profile estates attached to his name, residential real estate is not the family business; that’s Flagg Family Capital, where he has big shoes to fill.
Flagg’s paternal grandmother was Edith Flagg, who started the ready-to-wear label Edith Flagg Inc., which is credited with being the first to import polyester to the U.S. in 1967.
After apparel, Edith and Josh’s father, Michael Flagg, turned their focus to real estate, purchasing a 46,000-square-foot office at 400 South Beverly Drive in Beverly Hills. On the roof was a neon “Flagg” sign, “so large, you could see it from the moon,” Michael remembered. It became known as the Flagg Building and embarrassed everyone except Michael’s father, who liked the attention grabber.
Josh’s mother, Cindy Flagg, is from the Platt family, one of Los Angeles’ oldest Jewish families, and is also involved in real estate. Within the family’s real estate portfolio were multiple properties on Broadway in Downtown Los Angeles, including the Platt Fine Arts Building. Josh’s great-grandfather, Benjamin Platt, was also one of the founding board members of City of Hope.
“We talk about things no one bothers with anymore — China patterns, menu sequences, whether French service is more elegant than English service.”
In 2023, Michael shifted business responsibilities to Josh, who is now looking to move the focus from shopping centers and offices into the high-end spaces of New York, Miami and Palm Beach real estate.
For many scions, the heat would be on to make a mark on the family business, become a part of the history. Despite this switch in the business model, Josh doesn’t feel it.
“I don’t have any pressure because I don’t have any kids yet and, you know, I’m the only son,” he said. “So, I’m doing what I think is best and what I know how to do.”
In doing things his way, he is reshaping the family firm’s strategy.
“There are two schools of thought: long-term appreciation versus cash flow. I have always believed in cash flow, and it took a long time for me to understand [Josh’s] mentality,” Michael, who declined a phone interview with TRD, wrote in an email. “But when I saw him purchase for us a few things that were worth two times or even three times what we paid within a short time, I effectively changed my mind.”
What Michael saw flipped the script on what he viewed as Josh’s core trade competency as a “residential guy” and instead showed that he had the “Midas touch” on real estate, period. With Michael, at over 80 years old, no longer interested in expanding the portfolio, Josh’s increased responsibility was a natural transition.
“Josh is more than half my age; I had him when I was 42,” Michael said. “This is where Josh comes in. It’s Josh’s future and he has clearly proven himself to be very smart when it comes to real estate. When I turned 80, I am not sure if it was a conscious decision or whether I was just ready to turn things over unconsciously, but now Josh is in charge of everything.”
Michael still has the final yay or nay, but Josh finds the deals, runs the numbers and presents opportunities to his father. Among the family’s newer real estate investments was in New York, 5,500 square feet of Soho retail space at 170 Mercer Street, which they picked up for an undisclosed amount. He’s now in the process of opening a family office in which Michael also appears to be putting his full trust in his son.
“I leave it to him,” he said. “You know, he gets it from my mother.”
Only child
For Flagg, the work comes across almost as if it’s rote, nothing to get overly excited about nor to brag about, whether looking backward or forward.
“What motivates me?” he said. “I mean, I’ve just always been driven by work. I love working. I don’t know what I would do if I didn’t work. I’d be bored out of my mind.”
At the dining room table of his Trousdale Estates home last year, he fielded questions about his plans. He doesn’t see any one of his businesses eclipsing the others, he said. Being all over the place is just how it goes for him.
Work colleagues and close friends seem to have a better handle on him. They describe Flagg as an old soul who’s different from his TV persona, which, as he described on episode 1 of season 15, is “egotistical, condescending, somewhat rude and abrasive.”
“Josh is hilarious and I don’t think on TV — he does come off as Josh — but I’m not sure that people get truly how funny he is and how smart he is,” Rivers, who considers Flagg a loyal friend, said. He was one of the first to invite her to stay after she lost her home to the Palisades Fire.
Spelling, the wife of the late TV and film producer Aaron Spelling, chats constantly with Flagg; the two travel together often.
“People love to analyze it,” she said of their friendship. “They’ll say, ‘Why are Candy and Josh so close? You’re from different generations.’ And I tell them, ‘Because we’re the same species: collectors.’”
That’s how the two met: competing against one another at a Christie’s auction in New York.
“We talk about things no one bothers with anymore — China patterns, menu sequences, whether French service is more elegant than English service,” said Spelling, who describes herself as shy and responded to questions via email rather than by phone.
Flagg was precocious as a child and always friends with adults. His favorite pastime was chatting with grown-ups at the Polo Lounge in Beverly Hills or at the Brentwood or Hillcrest country clubs — his parents or grandparents and their acquaintances. He’d play with the art or furniture in his grandmother’s penthouse, or visit with her next-door neighbors, Mattel founders Ruth and Elliot Handler.
The obsession with real estate also began when he was young.
“If I was six years old and I had a temper tantrum, the only way to calm me down, my mom would put me in her Mercedes convertible and we’d drive around the neighborhood and look at houses and gates,” he said.
Michael recalled cities built of Legos strewn about Josh’s childhood bedroom floor with model Rolls Royces parked outside buildings. Mischievous, Josh would take the house keys out of guests’ pockets at dinner parties or family gatherings, Michael remembered.
“At five years old, he had an affinity for anything that had to do with real estate,” he said. “I guess a key to him meant something even back then.”
Master of all trades?
Some say the Cheshire Cat from “Alice in Wonderland” is symbolic of the power that comes from detachment. When one cares nothing about proving oneself with industry awards or rankings, constraints no longer exist in one’s sense of self.
“There’s certain guys that are very specific — they just want to golf all day and build stuff, or you’ve got guys that stay in their own lane, whether it’s retail or multifamily or whatever. And Josh is really more opportunistic,” Richard Weintraub, president and CEO of Weintraub Real Estate Group, said. Flagg is harder to pin down, he added.
Weintraub, a fourth-generation Angeleno like Flagg, is behind some of the region’s most significant retail projects, including the Malibu Lumber Yard and Shops at Sportsmen’s Lodge in Studio City, and the two are eyeing a couple retail development possibilities in Southern California by the beach, according to the developer.
Weintraub offered his take on the duality of Flagg: “He can go from having one too many to really locking down the numbers on a deal very easily.”
And Flagg’s Estate Media, the real estate platform with original shows and podcasts, is scaling. It has $1 million in seed money raised last month from investors such as Compass’ Tracy Tutor and the Hudson Advisory team in New York, in addition to TikTok co-founder Justin Mateen and his brother Tyler Mateen.
Griff O’Brien, Estate Media co-founder and CEO, said he’s noticed that Flagg flips a switch from funny to serious when it comes to business.
“He’s much different than what the camera puts on,” he said.
Still, with all the talk about Flagg’s serious approach to business, long-term planning (much like emphasizing cash flow) is not his style. Asked where he hopes each of the businesses he’s involved with might be in, say, a decade, he declines to make projections.
Some might view that as the privilege not to have to worry about success. Others figure it’s part of the secret.
He minimizes the contrast.
“That’s not really how I think about it,” he said. “I don’t really think about the future. I just think about the present.”