Stephen Cloobeck Net Worth

What is Stephen Cloobeck's net worth?

Stephen J. Cloobeck is an American businessman who has a net worth of $500 million. Stephen Cloobeck earned his fortune as the founder of the timeshare company Diamond Resorts International. He became more widely known after being featured on the reality series "Undercover Boss" in 2012. Unfortunately, in recent years, he has become known for his association with several controversial figures, including former congressman Eric Swalwell. In May 2026, Cloobeck was arrested in Los Angeles on a felony charge of attempting to prevent or dissuade a victim from testifying. More details on his arrest later in this article.

Stephen earned a huge fortune thanks to Diamond Resorts International. The exact size of the fortune is not known. What is known is that in 2016, Stephen sold Diamond Resorts for $2.2 billion in cash. At the time of the sale, he owned around 22% of the company's equity, which translated into a $500 million pre-tax windfall.

Stephen has claimed in various interviews to be a billionaire. That is certainly possible. He owns a home in Beverly Hills that he claims to be worth $100 million and a home in Cabo that he claims to be worth $45 million. He has also been divorced twice. He and his first wife, Heather, were married for 13 years. He was then married to a model named Chantal Leduc from 1997 to 2018. Chantal received their former $40 million mansion in Laguna Beach in the divorce, and presumably other assets, especially considering the divorce occurred AFTER the sale of his company and AFTER 20+ years of marriage. In 2024, Stephen announced his candidacy for the 2026 California Governor's race. Hopefully, he'll release a detailed financial statement to confirm or deny his billionaire status.

Early Life and Career Beginnings

Stephen Cloobeck was born on October 26, 1961. He graduated from Brandeis University in 1983 with a degree in Psychobiology. He initially intended to become a surgeon or a lawyer and was accepted into both medical and law school. It's unclear how or when his path changed, but he soon found himself building shopping centers in Southern California. His first shopping center project was in Burbank. He went on to build shopping centers in a half dozen other SoCal cities before moving on to Las Vegas. In 1991, he began construction on a hotel in Las Vegas. In 1992, the 21-story Polo Towers hotel opened on the Strip.

Diamond Resorts International

In 1992, Stephen founded Diamond Resorts International. He grew the company to a point where it operated more than 370 resorts around the world that specialize in timeshares. The company's resorts are located in 35 different countries, and more than 400,000 people use Diamond's hotels each year for their vacations. In April of 2007, he acquired the publicly traded Sunterra Corporation.

In June 2016, Stephen sold his timeshare assets to Apollo Global Management for $2.2 billion in cash, a 26% premium to its previous closing price. Cloobeck, the majority owner, walked away with $500 million in cash. Today, Diamond Resorts is owned by Hilton.

(Photo by Leonard Ortiz/MediaNews Group/Orange County Register via Getty Images)

Undercover Boss

Stephen became more well-known after appearing on the reality series "Undercover Boss." He first appeared on the series in January 2012 on season 3, episodes 1 and 2. He has gone on to make numerous appearances on the series.

Personal Life

Stephen and his first wife, Heather, were married for 13 years. In 1997, he married Chantal Leduc, a Canadian model who won Star Search in 1993. They divorced in 2018. They have three children together.

By 2026, Cloobeck was engaged to 28-year-old Adva Lavie, an Israeli OnlyFans creator and former Penthouse Pet. In April 2026, Lavie made headlines when she was arraigned on felony burglary charges, accused of allegedly stealing from the homes of other wealthy older men.

Politics and The 2026 California Governor's Race

In addition to his business ventures, Cloobeck is highly politically active. He explored a run for Nevada Governor in 2007, and in November 2024, he officially launched a campaign for Governor of California as a Democrat. He poured millions into his campaign before dropping out in November 2025 to endorse Rep. Eric Swalwell. However, in April 2026, Swalwell's campaign imploded amid a slew of sexual misconduct allegations. Cloobeck quickly withdrew his endorsement, publicly rebuked Swalwell, and announced he was leaving the Democratic Party altogether to become a "Libertarian-Republican."

OnlyFans Girlfriend + Lawsuit

In 2020, Stephen began dating an OnlyFans model named Stefanie Gurzanski. They met through a matchmaker. In December 2020, he reportedly spent $130,000 throwing Stefanie a 36th birthday party at his Cabo San Lucas house with five of her girlfriends. Stephen, who would have been 59 years old on the day of his girlfriend's 26th birthday, flew the group to Cabo on his Bombardier Global Express private jet. As a birthday present, he reportedly gifted her $200,000.

Stephen reportedly spent $1.3 million on Stefanie during the FIVE months they dated. It was later alleged by Cloobeck that Stefanie demanded $2 million in cash and a $7 million house in exchange for giving up her OnlyFans account.

In January 2021, Stephen sued Stefanie, claiming various offenses, notably fraud and trespassing. A few weeks later, he filed an amended complaint that demanded the return of his money and property. At one point, Stefanie requested a temporary restraining order against Stephen, claiming she was "in fear for my life and well-being." The restraining order was granted. For his part, Stephen was upset upon learning that Stefanie took nude photos without his permission in various rooms of his various mansions, his private jet, his private suite at a hotel in Las Vegas, and more. She would then post those photos on OnlyFans. In September 2020, she allegedly took a nude photo wearing a yarmulke from his son's bar mitzvah and posted it on Rosh Hashanah, a significant Jewish holiday.

Adva Lavie Relationship

Cloobeck's relationship with model and social media influencer Adva Lavie, also known as Mia Ventura, became the subject of significant media attention in 2026 after Lavie was accused of targeting wealthy victims in an alleged theft scheme. According to prosecutors, Lavie allegedly used dating apps and social media from 2023 to 2025 to cultivate relationships with affluent older men and younger women in the Los Angeles area. Authorities alleged that she posed as a girlfriend or travel companion to gain access to victims' homes before stealing cash, gold, and high-end designer items.

In March 2026, the Los Angeles County District Attorney announced that Lavie had been held to answer on six felony charges: two counts of unauthorized use of personal identifying information, two counts of grand theft, one count of first-degree residential burglary with a person present, and one count of first-degree residential burglary. Lavie pleaded not guilty to all charges. Prosecutors said that if convicted on all counts, she faced up to 11 years and eight months in state prison.

Lavie had previously appeared in "Playboy" and "Penthouse" and claimed to be Israel's first top OnlyFans model. By the time the case became public, she was out of custody on an ankle monitor and had been ordered to stay away from the named victims. Cloobeck was later identified as Lavie's fiancé, connecting him directly to the case that led to his own separate arrest in May 2026.

2026 Arrest

In May 2026, Cloobeck was arrested in Los Angeles County on felony allegations that he attempted to prevent or dissuade witnesses from testifying in the criminal case against his fiancée, Adva Lavie. Lavie had previously been charged with multiple felonies after prosecutors accused her of burglarizing and stealing from wealthy men and women she allegedly met online. Authorities alleged that Cloobeck attempted to interfere with three male victims in Lavie's case, with prosecutors claiming the offenses involved "force and an express and implied threat of force and violence upon a victim."

Cloobeck was booked at the West Hollywood sheriff's station and released the same day after posting $300,000 bail. In addition to the felony witness-related charges, he was also accused of making annoying phone calls after allegedly contacting Lavie's attorney, swearing at him, and threatening him, his property, and members of his family. Cloobeck's attorney denied the allegations, calling the charges false and saying they looked forward to fighting the case in court.

Real Estate

Upon their divorce, Chantal took ownership of a $40 million mansion in Laguna Beach. They bought the home in 2007 for $10.5 million. Stephen owns homes in Los Angeles, Las Vegas, and Cabo San Lucas. His Cabo home is reportedly worth more than $45 million.

After paying $19 million for his Beverly Hills mansion, Cloobeck spent years waiting for city approval to construct his 16,000-square-foot dream mansion. He finally won approval in February 2017. He named the finished product "Papillon," which means "butterfly" in French. Cloobeck has claimed this house is worth $100 million.

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