Jason Oppenheim’s job is to sell a good sunset — but, when he’s not putting in the hours as president of the Oppenheim Group, the 45-year-old also enjoys his fair share of sunrises. Logging in at 1 p.m. from his West Hollywood office, Jason tells Tudum that he was out late party-hopping after the ESPYs. “I just dragged myself out of bed,” he groans. “Steph Curry had an after-party. LeBron James had an after-party. I met Steph, who’s a legend — he’s my favorite athlete, so that was supercool. It was just an awesome night.”
While Oppenheim’s agents count Marvel superhero Simu Liu and rapper French Montana among their clients, Jason doesn’t often get starstruck. “I don’t geek out over meeting anyone other than athletes. I just have so much respect for them,” he says.
Selling Sunset viewers might know Jason best as one of the Oppenheim brothers who lead the luxury real estate brokerage whose team of agents are, in some cases, more famous than their clients. But it’s sports, not real estate, that was his original love. Jason proudly shows off his stash of “inexpensive” baseball, soccer and football cards in his office (“All my best cards are in a safe deposit box”), and happily details an adolescence playing nearly every sport under the sun with his twin brother, co-star and business partner Brett Oppenheim. The brothers plan to go watch European fútbol team Real Madrid practice at UCLA later that day.
As Jason grows the Selling marquee with Selling the OC’s bustling Newport Beach office, he approaches real estate the same way he approaches sports: “I’m loyal. I don’t miss a game. I know everything. I don’t really know how to engage at a mid level. If I engage, I engage 100%.”
Make that 200%. On Aug. 24, Jason and the rest of the Oppenheim Group will launch seaside Selling Sunset spin-off Selling the OC. The show follows a new squad of glamorous real estate agents as they close deals, hit the beach and squabble at work parties. Although Jason is excited to open the Oppenheim Group’s Orange County office to viewers, he’s quick to stress that the business isn’t a made-for-TV choice. “I didn’t know we would have a show about the [OC] office when I was building it out and hiring some of my agents. But I was hopeful,” he explains.
“In Selling the OC, I’m working with a lot of the agents more because they’re just newer. I don’t know them as well. So I’m also developing a friendship and a professional relationship with them at the same time,” Jason says. It’s a very different dynamic than the one he shares with his Sunset co-stars, some of whom he’s known for decades. Mary Fitzgerald met Jason when he was still a lawyer. The pair would go on to date, break up and become colleagues and best friends at the Oppenheim Group. They each refer to the other as “family.”
“My ex-girlfriends are my closest friends in my life. Chrishell is certainly included in that too. Like Mary, I love her and I have so much respect for her,” he says.
During Selling Sunset’s Season 5 reunion, Jason showed a side rarely captured by cameras: the emotional one. He became visibly choked up reflecting on his relationship with co-star Chrishell Stause, which unfolds over the latest season, calling the mere suggestion of their courtship as a fake showmance “stupid.” Three months later, Jason remains real.
“I appreciate the love and the support, but I [have] a little bit of guilt over letting down the people,” he tells Tudum. The guilty feelings apply to Chrishell, but also to the fans. “People were so engaged and, to this day, are still so supportive,” he says.
But back to today, and Jason’s big night out. It’s rubbing elbows with basketball legends — not overseeing a brokerage empire — that’s his childhood dream come true. His mother, Deborah Stern (who made a memorable cameo in the fifth season of Selling Sunset ) tells Tudum that when Jason was 11, his teacher asked him to imagine where he would be in 15 years. One of his eight tweenage goals was to win an Olympic medal (along with “marrying an athletic, beautiful, kind-hearted woman” and having a “fast, dependable car”), so partying with decorated greats like LeBron is the next best thing.
“When they said they were approached to do a reality show, I said, ‘Don’t do it,’ ” Deborah recalls. “Their business was going well, and, at that point, Jason and Brett fought so much that I was afraid. But they did it. It’s kind of surreal.”
“I wanted to be the mother that got called to school for the gold star or the award, but I was called to school because homework wasn’t being done, there was misbehavior,” she admits. Jason even gave a March 2021 TEDx Talk referencing teenage brushes with the law. “We were screw-ups when we were younger. That’s not a secret,” Brett tells Tudum.
But then the twins followed in the footsteps of both their parents and attended UC Berkeley, where Brett says they did “really well” in school and changed their path. The boys who were once cuffed for fighting became lawyers. “He always downplays his attorney career — but he did the Enron trial. He’s a badass,” says Mary of the 2001 accounting scandal in which executives at Enron, a now-bankrupt American energy company, hid billions of dollars of debt. (Jason was part of the defense team.)
“We were [law students]. We were not that seasoned, so the fact that he was on the Enron team was crazy,” says friend and lawyer Natasha Chesler. “They let him handle a witness on his own and be at the counsel table when the witnesses took the stand. There may be a misconception that he’s just a partier and things come easily to him. But he works his ass off.”
“I don’t want to make him look bad, but the summer before we took the bar exam, [Jason] was partying with Brett,” she continues. “I’m like, ‘Dude, you’re not going to pass this thing. You cannot study for the bar exam in three or four days. It’s not going to happen.’ ” But sure enough, the twins studied for three days and passed “with flying colors.”
Still, something was missing. By 2007, Jason had put in five years at his “prestigious” law firm, O’Melveny & Myers LLP, while Brett had left law altogether. “My brother really was the catalyst for me quitting. I would argue that day when I put in my two weeks, that changed everything,” Jason says. He calls the moment the most meaningful decision of his life, placing it above starting the Oppenheim Group.
“I vividly remember sitting at a cafe and not having to use my BlackBerry — not having this stress of any work. It was just shocking,” Jason continues. After the sprint from college to law school to O’Melveny & Myers, his time was truly his own for the first time in a decade. “I didn’t even know what that felt like. The idea of not having responsibility was so overwhelmingly peaceful,” he says. He left LA and traveled around the world for a few years.
But the life of a globetrotting vagabond would never stick. In 2010, he returned to LA and entered the real estate business. He helped Natasha buy her first home and liked it so much he told her he planned to start his own brokerage. In 2013, he and his brother opened the Oppenheim Group. “I got my real estate license first, but he executed real estate better than me,” Brett jokes. (“I also think I lost my virginity first. I quit law first. But he came out of the womb first.”)
“With [real estate], there’s not really a cap on your success. If you’re really smart and you work hard, no one’s going to hold you down as far as how much you can make,” Brett explains.
“It’s very self-motivating because it’s kind of do-or-die every day,” Jason says. His workweek went from endless hours behind a desk, to a perpetually shifting agenda of lunches (“Din Tai Fung, LAVO, Catch Steak, Melroseplace, Olivetta — that’s my top five”), property showings, penthouse visits and the managing of “hundreds of clients and dozens of agents.” He wakes up to Dua Lipa and Elton John’s “Cold Heart,” enjoys a morning cup of coffee, and takes his beloved dogs — his ”kiddos” Niko and Zelda — to the office. (“You can’t bring dogs to the law office,” he says.)
For those who might question Jason’s commitment to real estate over reality show stardom, Jason says his loyalties haven’t changed. For him, real estate has come to “engulf” his life — “in a positive way,” he promises. “The land, the location, the scale, furniture, artwork, all the finishes. Anything that even remotely pertains to real estate, I’m obsessed with,” he says. That obsession extends to the aspects of the job some might find boring, such as financing and accounting.
“I was a well-known real estate agent before the show. So it really just started so gradually over the last 10 years,” Jason says. “It’s not like a switch flipped. It feels completely normal to me at this point.”
What hasn’t been as normal has been the public scrutiny surrounding the (lack of) boundaries between his professional and personal life — especially when it comes to his romantic partners. But, for all intents and purposes, Jason says his relationships have mostly gotten healthier since Selling Sunset. The show has even improved Jason’s formerly antagonistic relationship with Brett, who describes the physical confrontations and arguments they used to have as “ridiculous — [a] seriously low bar.” Today, Brett sees Jason as much more than an opponent: “We have each other to fall back on. You never really feel like you’re alone in the universe.”
Says Mary, “He is the most loyal guy I think I’ve ever met. [Some] people truly deserve to be fired, [but] he has such a big heart. I don’t think that comes across as much on the show because he’s a boss. But he’s the most generous and loving person.”
But is it smart to harbor so much love and loyalty for co-workers? For now, the strategy has worked out. Jason turns introspective while pondering what those rules are. “Don’t ever wrong the person that you love,” he says. “At some point you get over the breakup and then you’re left with the friendship and the love that you had in a relationship. What I don’t get is how people tell their significant other they love them, are actually in love with them, and then aren’t. Then all of a sudden, that person is a bad person.” This behavior does not compute with Jason. “That to me is the weird thing: Not being friends with someone that you woke up next to and told that you loved.”
He credits his experiences on Selling Sunset with Chrishell as a springboard into the future. Continuing to film the Selling universe is the “biggest endeavor” in life. “I was so comfortable filming with Chrishell that, at this point, I feel very good in front of the camera and I don’t really hold back,” he says. “I’m as happy and confident in my life and in front of the camera now, as ever.”
