A number of well-considered choices, most notably the purchase and conversion of the timeshare company into a high-end leisure brand, contributed to Stephen Cloobeck’s net worth, which is frequently estimated to be around $500 million. He carefully combined ownership, service, and branding into a single, incredibly successful hospitality model, creating an ecosystem rather than merely a business. When he bought Sunterra Corporation in 2007 and transformed it into Diamond Resorts International, an organization that soon served over 400,000 members and operated in more than 35 countries, it was his most revolutionary move.
He sold Diamond Resorts to Apollo Global Management in 2016 for $2.2 billion in cash, following years of growth and brand development. Cloobeck personally took home about $500 million, pre-tax, as the biggest shareholder. By itself, this deal greatly improved his financial situation and established him as one of America’s most prosperous independent hospitality leaders. A change from active entrepreneur to donor, investor, and public figure was also marked by the sale.
Stephen Cloobeck – Personal and Professional Overview
| Attribute | Detail |
|---|---|
| Full Name | Stephen J. Cloobeck |
| Date of Birth | October 26, 1961 |
| Nationality | American |
| Education | Brandeis University, B.S. in Psychobiology (1983) |
| Profession | Entrepreneur, Philanthropist, Former CEO of Diamond Resorts |
| Estimated Net Worth | Approximately $500 million |
| Primary Business | Founder and Former Chairman, Diamond Resorts International |
| Major Asset Sale | Sold Diamond Resorts to Apollo Global Management for $2.2 billion |
| Public Appearance | Featured on Undercover Boss (multiple episodes) |
| Political Aspiration | Running for Governor of California in 2026 |
| Notable Properties | Homes in Beverly Hills, Cabo San Lucas, and Las Vegas |
Cloobeck has made an impact in almost every setting he has visited in the last ten years thanks to his wealth. In real estate, he created “Papillon,” a mansion in Beverly Hills that took years to approve and construct and is said to be worth $100 million. In addition, he owns an estimated $45 million worth of real estate in Cabo San Lucas and houses in Las Vegas. His signature style—personal yet stylized, expansive yet clearly functional—is evident in every home.
Working with top architects and urban planners, he has produced not only residences but also manifestations of his aspirations. His real estate strategy embodies a transformational mindset: taking potential and transforming it into permanence.
In recent years, Cloobeck’s philanthropic profile has significantly improved. In addition to pledging $1 million to rename McCarran Airport after Senator Harry Reid and contributing $400,000 to the victims of the 2017 Las Vegas shooting, he also continues to support charities focused on education and health. Of particular significance is his $1 million endowment at Brandeis University, where he graduated with a degree in psychobiology. It signifies a return to his roots by recognizing the organization that influenced him prior to starting his business endeavors.
He further demonstrated his dedication to social impact by establishing the Brent Shapiro Foundation for Drug Prevention through strategic partnerships. Create, structure, and scale is a strategy he has used here that is remarkably similar to his business style.
His most well-known public appearances may have been on Undercover Boss, where he wore disguises to assess Diamond Resorts’ employee experience. These nationally televised episodes gave viewers a unique glimpse of a CEO who was prepared to fully commit to the business. His responses, which were frequently emotional and surprisingly candid, strengthened his reputation as a leader who was incredibly open about his beliefs and had a strong bond with his employees.
His aspirations for politics have solidified. Cloobeck declared in November 2024 that he would run for governor of California in 2026 as a Democrat. He had previously contemplated running for office in Nevada, so this wasn’t his first time dabbling in politics. In a 2017 MSNBC interview, he made headlines by expressing his displeasure with class-based political rhetoric by threatening to cut off funding for Democrats who disparaged wealthy Americans. Although contentious, it established him as a fearless, vociferous donor who was not hesitant to stand up for capitalism in its most acerbic form.
Despite all of his honors, his private life has occasionally made news in ways he probably did not expect. His brief liaison with Stefanie Gurzanski, an OnlyFans model, resulted in restraining orders, media attention, and legal complications. In just five months, he reportedly spent $1.3 million on her, including gifts, airfare, and a $200,000 birthday celebration. He had felt coerced, according to a later lawsuit, especially after learning that Gurzanski had taken explicit pictures on his properties without his permission. Despite being extremely personal, this episode highlighted the difficulties that can occur when personal relationships collide with public awareness.
Even so, Cloobeck has utilized his failures to strengthen his story. He openly acknowledged in a 2025 interview that he was “naive to the dating scene,” displaying an unusually candid tone uncommon among executives of his caliber. He set himself apart from others who hide behind PR walls during controversy by admitting his vulnerability.
His ability to expand his influence beyond business and philanthropy into politics will probably be put to the test during his gubernatorial campaign in the upcoming years. His perseverance in switching from science to real estate, then to hospitality, media, and public service, is the true lesson for aspiring business owners looking at his trajectory. His career hasn’t been linear; rather, it shows a highly adaptable mindset that can adapt to changing circumstances and reinvent itself.
