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• Josh Flagg, an original cast member of Bravo's "Million Dollar Listing Los Angeles," is one of the most successful real-estate agents in Beverly Hills, California.
• Flagg leads Josh Flagg Estates, a division of Rodeo Realty, one of California's top-ranked real-estate teams, and says he's closed more than $300 million in sales this year alone. 
• He has a list of celebrity clients and unmistakable style and shared in an interview with Business Insider the daily routine he follows to maximize his productivity.
• Visit Business Insider's homepage for more stories.

Josh Flagg is no stranger to success. An original member of Bravo's "Million Dollar Listing Los Angeles," which is now in its 13th season, Flagg has worked in real estate for 17 years and sold homes to big names like the singer Adam Levine, the TV executive Shonda Rhimes, and the DJ Steve Aoki.

Flagg has closed more than $2 billion in sales and made his first real-estate deal at just 18 years old on a historic property in Beverly Hills, California, that once belonged to Mohammed al Fassi, a Saudi sheikh. Though he attended the prestigious Brentwood School and graduated from Beverly Hills High School, Flagg skipped college, as he was eager to focus on his career. 

Now 35, he's the founder of Josh Flagg Estates, a division of Rodeo Realty, a top-ranked California real-estate team, according to Real Trends. He told Business Insider he sold $300 million in luxury Los Angeles real estate in 2020 alone.

Flagg and his husband, Bobby Boyd, who's also an agent and former model with appearances in Vogue and GQ, are known for their style. And Flagg's powerful combination of panache and industry expertise has landed him some of the city's most prominent listings.

Flagg has a long list of celebrity clients and has sold homes to famed California families like the Gettys (of art philanthropy fame) and DeBartolos (of NFL ownership fame). His most notable deals include the sales of the socialite Betsy Bloomingdale's $40 million estate in LA's exclusive Holmby Hills enclave and the similarly priced 1001 North Roxbury Drive property in Beverly Hills earlier this year. A design buff, he's repped several homes by architects to the stars like John Woolf (who built homes for Cary Grant, Katharine Hepburn, and Bob Hope), Hal Levitt (commissioned by the likes of Steven Spielberg, Dean Martin, and Lionel Richie), and Ed Fickett (clients included Irene Dunne, Dick Clark, and Diana Ross). 

Flagg leads a team of 10, of whom six are agents and four are support staff. He said no two days were the same but credited much of his success to his rigorous schedule, which runs from 7:30 a.m. to 2 a.m.

He let Business Insider follow along for a day in early November.

7:30 a.m.

Wake up.

Breakfast is a slice of smoked salmon from Beverly Hills' landmark Jewish deli Nate 'n Al's. It's the only place his grandmother Edith Flagg used to buy smoked salmon, so he keeps the tradition alive.

Flagg eats the salmon on a thin piece of rye toast in bed. One of his three assistants, Claire Jenkins, goes over his schedule for the day at his bedside.

The pair discuss filming for "Million Dollar Listing," listings he's representing, and plans for Flagg's third book, which he just started working on. After 45 minutes of watching CNN, he gets dressed. 

He calls one of his best friends, Carrie Brillstein, for a chat. She, the widow of the powerhouse American film producer Bernie Brillstein of "The Sopranos" and "Ghostbusters," Flagg, and their mutual friend Amy Weiss — a Brillstein talent manager who tells Business Insider Flagg sends the best text messages she's ever received, alluding to his humor — talk ideas for Flagg's upcoming book. It's set to talk about Flagg's trajectory in real estate, as well as his best career advice, and is a follow-up to 2009's "A Simple Girl: Stories My Grandmother Told Me" and 2011's "Brokering The Dream."

Then it's time for a shower, where Flagg keeps a waterproof notepad. His mind is constantly running, he said, so he'll often jot a thought down so he won't forget it.

8:15 a.m.

Daily phone calls kick off with East Coast clients, buyers, and sellers — in case some of his West Coast regulars are still sleeping.

He takes some time to chat with his entrepreneurial partner Adam Rubin to discuss real-estate ventures: They are looking for the perfect location to bring back the iconic Beverly Hills restaurant Chasen's. "We're all set to go," Flagg said, adding that they were working with the Chasen family to bring the project to life. "The only thing we need is the perfect location, which we're not going to sacrifice." 

Flagg, who is heavily involved in charity causes, hops on a quick call with the Guardians of the Los Angeles Jewish Home manager Jessi Cazary and his childhood friend Zach Zalben (the grandson of Stanley Black) of Black Equities to discuss fundraising. 

9:15 a.m.

Flagg and Boyd reside at the Beverly Hills home of the late Connie Wald, a hostess of Hollywood's golden age known most for her entertaining. About 9, he heads downstairs for a design meeting with Boyd and their architect William Hefner regarding the house they're building in Beverly Hills. "His enthusiasm for the project is infectious," Hefner told Business Insider.

The home will be just under 7,000 square feet in The Flats neighborhood of Beverly Hills and hold seven bedrooms and nine bathrooms. Flagg says they're hoping to construct the "highest-quality" house in The Flats and expects it to be completed in 2023.

Flagg proclaims that he's indecisively ripped the house apart twice already and brought Hefner in to "control his insanity." In four months, construction will restart for the third time. When it's finished, it will have been a two-year project. "The neighbors hate me, especially the gentlemen to the north," Flagg said, adding that one neighbor even told Flagg he'd consider putting his house up for sale if Flagg started construction again. Little do they know that the house is soon being torn down for what Flagg calls "the big one." 

After the meeting, Flagg's friend Patty Finkel — a sculptor with a line at the luxury furnisher Jean de Merry — stops by to see how one of her pieces (a recent purchase Flagg bought from Jean de Merry) looks in his home. The interior designer Roxy Sowlaty, Flagg's design partner, then comes over to discuss a furniture-line collaboration inspired by designs from Flagg's grandmother's penthouse, which was on Los Angeles's Avenue of the Stars. The line will be available for sale in several design centers across the country. 

His grandmother Edith was the prominent fashion designer known for bringing polyester to the US.

10 a.m.

Flagg is off to an inspection for an $11 million house on Shadow Hill — an exclusive street in Beverly Hills — that's closing tomorrow. 

Since the COVID-19 pandemic hit, he's been working more from home than from his Beverly Hills office. In-person meetings take place in Flagg's backyard or dining room, which has essentially been turned into a conference room, complete with a ring light.

11 a.m.

Flagg and his pal Natalie Bloomingdale, a socialite who also owns the online retailer The Stuff I Love, make a stop at Julien's Auctions to buy a pair of paintings belonging to the estate of the film producer Robert Evans. (Evans, who worked on "Rosemary's Baby," "Chinatown," and "The Godfather," died in 2019.)

Jenkins joins them to go over the guest list for a socially distanced outdoor dinner party Flagg is hosting. Guests include the TV host Melissa Rivers, the singer Charo, and the supermodel Cheryl Tiegs. "A very eclectic crowd," Flagg says.

Rivers tells Business Insider that Flagg is a "great host with a deep intellectual understanding of design," adding that every detail at one of his dinner parties is meticulously thought out and perfectly presented, from fantastic food to gorgeous flowers. 

Rivers also said she recently gifted Flagg a set of salt and pepper shakers once owned by her mother, the late comedian Joan Rivers, on the condition that he consider a donation to the Biden campaign. He loved the gift like no one else could, she said, and ended up making a generous donation.

11:50 a.m.

Flagg makes a quick stop back at his house on Beverly Drive to meet with his stylist, Sarah Salter, and go over his outfits for fall and Christmas.

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Salter catalogs all of Flagg's looks so that he doesn't have to think about what to wear, and choosing an outfit is as simple as flipping through a booklet of his favorite choices. Business Insider asked Flagg what his three favorite brands were. He replied Tom Ford, Yves Saint Laurent, and Gucci. "Tom Ford fits like a glove," Flagg said, adding that YSL is an innovative classic and Gucci is back under the leadership of Alessandro Michele. "Gucci was off the map for years and Alessandro made it relevant again." 

12 p.m.

Lunch is almost always at the Polo Lounge, a trendy eatery at the Beverly Hills Hotel. If he's not there, Flagg said, "something's wrong." Flagg is one of two guests that use a landline telephone at his table. 

He spends 20 minutes having coffee with Pepe, the maître d', before his guests arrive, and then lunch tends to last about an hour or so. (The Polo Lounge is operating under takeaway-only guidelines, per California's pandemic regulations.) 

1:30 p.m.

Flagg drives to Malibu to meet with clients. The listing he's showing them — on which he's colisted with his husband — is Matthew Perry's $13 million beach house.

On the way, Flagg has a call with the Holocaust Museum LA, where he's on the board. Both the museum and the Guardians of the Los Angeles Jewish Home honored Flagg last year for his charity work.

Listing appointments and showings happen all day long, whenever he can fit in a prospective buyer or seller. Every day is different, and his schedule is often packed. Despite his collection of classic cars — which includes a 1960 Rolls-Royce Silver Cloud Drophead convertible, among mostly other Rolls-Royces and vintage Mercedes — he doesn't spend too much of the day behind the wheel.

3 p.m.

Flagg makes a quick stop at home to oversee an art installation — two portraits of Tina Turner and Cher by the South African photographer Norman Seeff.

Then it's time for a Zoom call with the local Cultural Heritage Commission. Flagg is a commissioner in the city of Beverly Hills. The group meets regularly to recommend historic properties that should receive official designation (and, as a result, protection) and discuss other preservation issues.

4 p.m.

Back at the Polo Lounge, Flagg meets with one of his best friends, James Bloomingdale (Natalie's husband and a member of the family behind the legendary department store). They're partnering up for a commercial business deal, and the pair have invested in apartment projects together in the past.

Flagg brokered the sale the Holmby Hills home of Bloomingdale's grandmother — the socialite Betsy Bloomingdale — to the designer Tom Ford for just under $40 million in 2016.

Afterward, Flagg heads home to interview a new candidate (Michael Kagan, the head of international TV and media at ICM) for the board of governors of Cedars-Sinai, one of the area's renowned nonprofit hospitals. Flagg is on the board of governors' executive committee and has long-standing family ties to the hospital. His grandfather Herman Platt was a founder of Mount Sinai Memorial Park Cemetery, whose executive administration building bears his name. Platt was also the president of Sinai Temple, the oldest and largest Conservative Jewish congregation in Los Angeles, where his father was founder and president for 24 years. 

The Platt family is known as the oldest Jewish family in Los Angeles, Flagg said, adding that his great-grandfather Benjamin Platt (Herman's father) was considered one of the great Jewish leaders of the community as a cofounder of Sinai Temple, City of Hope, Hillcrest Country Club, and the Jewish Home for Aging. Flagg told the story of Platt's death, which was marked by the early adjournment of city hall on April 16, 1960, in memory of his passing. 

In the powder room of Flagg's home are memories of his family — among other memorabilia like items from the Titanic — where letters from Thomas Edison and his great-grandfather live next to handwritten notes from Tom May (of the May Co.) and Benjamin Platt.  

5 p.m.

Flagg is headed to Dr. Harold Lancer for a dermatological touch-up. He chitchats with Lancer, who counts many celebrities as clients, about their love of art for a few minutes before a chemical peel.

Then it's time to head home for dinner, which is being prepared by his housekeeper Olympia Gramajo, a gourmet chef who, according to Flagg, lived in Italy for many years.

Dinner tonight will be French onion soup and beef Wellington, Flagg's favorite. Boyd, who vlogs about cooking, makes dessert: peach cobbler. "He's very talented," Flagg said.

Tonight's cocktail of choice, sipped about 6:30 p.m., will be a Gibson. It's a cousin of the martini made with gin, dry vermouth, and a pickled cocktail onion.

7 p.m.

Flagg and Boyd sit down to eat, joined by Flagg's parents, Michael and Cindy, who live just a few minutes away. Flagg was born and raised in Log Angeles, and his father became involved in commercial real estate after he retired as President and Vice Chairman of the Board of Edith Flagg Inc.

Other guests around at the dinner table on this particular evening are Paula Abdul, the "Will & Grace" producer Max Mutchnick and his power-attorney husband, Erik Hyman, and the Disney executive Ricky Strauss.

Afterward, an evening nightcap via Zoom with the fitness guru and actress Suzanne Somers and her husband, the former TV host Alan Hamel, before Flagg packs to go to Mexico with the internist and frequent TV guest Drew "Dr. Drew" Pinsky and the actress Heather McDonald. "Josh is the real deal," Somers told Business Insider. "He is a gourmand hedonist, so I love cooking for him." 

9:30 p.m.

Flagg has a call with his life coach, Breck Costin. Costin is known for guiding some of the biggest names in Los Angeles, Flagg said. "I don't know what I would do without him," Flagg added.

Costin tells Business Insider that Flagg is humble, curious, and "first and foremost dedicated when something is important to him." 

10 p.m.

Time to watch CNN and work from his living room. Boyd heads to bed about 11:30 p.m., so from then on Flagg is up alone catching up on work beside their fireplace. 

Because of so many daytime phone calls, Flagg tends to tackle the leftover work, like paperwork and emails, at night.

11 p.m.

Flagg's masseuse, Victoria Flores, who was the head masseuse at the Four Seasons Mexico City for over 20 years, comes to his house to administer an evening massage every Monday. It's a tradition started by his grandmother that Flagg carries on.

Edith Flagg's masseuse, Minka, massaged her for 50 years and had no family or heirs, Josh Flagg said, and Edith Flagg took care of her financially and emotionally for her entire life. Upon Minka's death, unbeknownst to the Flagg family, she left Edith over $250,000. Josh Flagg said his grandmother had been so generous to Minka over the years but that the sum came as a shock and his grandmother donated the inheritance to the Jewish Federation of Los Angeles and other charities. 

"My grandmother was the only person that was ever there for her during her life and never expected anything in return," Flagg said. "The irony is that she left all of her money back to my grandmother, which [she] immediately gave away."

12 a.m.

Josh checks in with — or prank calls — his friends and fellow "Million Dollar Listing" castmates Tracy Tutor, Josh Altman, David Parnes, and James Harris.

He's known for ringing up folks late at night after a few glasses of wine and playing practical jokes. At this point, he said, he's lucky if a few of them even pick up.

2 a.m.

Bedtime.

Flagg falls asleep to "Ratched," a Netflix thriller starring Sarah Paulson as a psychiatric nurse based on "One Flew Over the Cuckoo's Nest." Flagg joked that he has a lot in common with the main character. "The main character reminds me of myself," Flagg said. 

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