Stephen Cloobeck, 63, is a self-made businessman best known as the founder of Diamond Resorts International. With an estimated net worth of $500 million, Cloobeck has lived a life full of business wins, public controversies, and political aspirations. While he’s long claimed billionaire status, the exact size of his fortune remains speculative. His story, however, is anything but ordinary.
Early Life and Career Shift
Born on October 26, 1961, Stephen J. Cloobeck grew up with aspirations far from the hospitality industry. He graduated from Brandeis University in 1983 with a degree in psychobiology, originally intending to become either a doctor or lawyer. He was accepted into both medical and law schools but never pursued either path. Instead, he pivoted toward real estate development, beginning his career by building shopping centers across Southern California.
By 1991, he had moved to Las Vegas, where he started construction on the Polo Towers, a 21-story hotel that officially opened in 1992. This was his entry point into the hospitality world and a preview of what would become his most lucrative venture.
Building Diamond Resorts International
In 1992, Cloobeck founded Diamond Resorts International, a timeshare company that would eventually expand to over 370 resorts across 35 countries, serving more than 400,000 customers annually. The company quickly became a major player in the vacation ownership space.
In 2007, Cloobeck made a key acquisition: Sunterra Corporation, a publicly traded timeshare company. This allowed Diamond Resorts to scale rapidly and boost its global presence.
By 2016, Cloobeck struck a major deal, selling Diamond Resorts to Apollo Global Management for $2.2 billion in cash. At the time, he reportedly owned 22% of the company, earning him a $500 million pre-tax payout. Diamond Resorts would later become part of the Hilton Grand Vacations portfolio.
Despite his claims in interviews to be a billionaire, documents confirming this have not been made public. Still, he maintains a high-profile lifestyle that aligns with someone in the ultra-wealthy class.
Personal Life and Family
Stephen Cloobeck has been married twice. His first marriage to Heather lasted 13 years. In 1997, he married Chantal Leduc, a Canadian model best known for winning Star Search in 1993. They were married for over two decades before divorcing in 2018. The couple has three children.
Following the divorce, Chantal was awarded their $40 million Laguna Beach mansion, a property the couple had bought in 2007 for $10.5 million. Given that the divorce occurred after the sale of Diamond Resorts, it’s presumed she received a significant share of assets.
High-End Real Estate and Lavish Lifestyle
Cloobeck’s real estate portfolio reflects his wealth. His most talked-about property is his Beverly Hills mansion, known as Papillon—French for “butterfly.” He bought the land for $19 million and spent years securing city approvals before constructing the 16,000-square-foot estate, which he claims is worth $100 million.
He also owns a $45 million villa in Cabo San Lucas and additional homes in Las Vegas and Los Angeles. His properties have been central to both his public persona and his personal controversies.
The OnlyFans Controversy
In late 2020, Cloobeck began dating Stefanie Gurzanski, a model with a large following on OnlyFans. Their five-month relationship made headlines due to its extravagant nature. Cloobeck reportedly spent $1.3 million on her, including a $200,000 birthday gift, a luxury party in Cabo, and flights on his Bombardier Global Express jet.
The relationship soured in early 2021, resulting in a lawsuit. Cloobeck accused Gurzanski of fraud and trespassing, alleging she took explicit photos in his homes and private jet without permission and posted them online. Gurzanski later secured a temporary restraining order, claiming she feared for her safety. The legal battle made headlines, highlighting the risks of high-profile dating in the social media era.
Political Ambitions
Stephen Cloobeck has long been active in Democratic political circles. In 2007, he considered running for Nevada governor. More recently, in November 2024, he officially announced his candidacy for Governor of California in the 2026 election.
If he moves forward, Cloobeck will likely face public scrutiny regarding his wealth, business history, and personal controversies. His potential run could also reveal more about his financial standing, especially if he’s required to file a detailed financial disclosure as part of the campaign.
Philanthropy and Public Image
Outside business and politics, Cloobeck has contributed significantly to charitable causes. He chairs the board of the U.S. Corporation for Travel Promotion and the Nevada Cancer Institute. He also founded the Brent Shapiro Foundation for Drug Awareness. In 2012, he made a major endowment to the Brandeis University International Business School.
He gained wider public recognition after appearing on CBS’s “Undercover Boss” in 2012. His episodes—season 3, episodes 1 and 2—showcased a more empathetic side, helping employees and highlighting company culture. He’s since appeared on the show multiple times.
