Stephen Cloobeck Biography: Age, Wife, Family, Diamond Resorts, Undercover Boss, California Governor Campaign
Stephen Cloobeck is a self-made American entrepreneur, philanthropist, and former timeshare mogul best known as the founder, chairman, and CEO of Diamond Resorts International, the global vacation ownership company he built into a major hospitality brand with hundreds of resorts before its $2.2 billion sale in 2016. The 64-year-old businessman gained widespread public attention through multiple appearances on CBS’s Undercover Boss, where he anonymously worked entry-level jobs and rewarded dedicated employees with generous gifts. After stepping away from daily operations, Cloobeck turned to philanthropy, public service, and politics—briefly running for California governor in the 2026 race as a Democrat before dropping out, endorsing then distancing himself from Rep. Eric Swalwell, and identifying as libertarian-leaning. His high-profile personal life, including two divorces and a 2026 engagement amid legal headlines, has kept him in the spotlight.
Quick Facts
| Full Name | Stephen J. Cloobeck |
| Nick Name | Steve |
| Profession | Entrepreneur, Businessman, Philanthropist, Political Activist |
| Birth Date | October 26, 1961 |
| Age | 64 (turning 65 in October 2026) |
| Birth Place | Encino, Los Angeles, California, USA |
| Nationality | American |
| Known For | Founder of Diamond Resorts International; multiple Undercover Boss appearances; 2016 company sale; philanthropy; brief 2026 California gubernatorial campaign |
| Ethnicity | Jewish-American |
| Zodiac Sign | Scorpio |
| Height & Weight | Not publicly disclosed |
| Hair Color | Graying |
| Eye Color | Not publicly disclosed |
| Qualification | B.S. in Psychobiology (Biopsychology), Brandeis University (1983) |
| Religion | Jewish |
| Marital Status | Divorced twice; engaged to Adva Lavie (as of early 2026, with wedding plans reportedly in jeopardy due to legal issues) |
| Previous Spouses | Heather Cloobeck (first marriage, lasted 13 years); Chantal Leduc (Canadian model and Star Search winner, 1997–2018) |
| Children | Three (with Chantal Leduc) |
| Family Tree | Son of Sheldon H. Cloobeck (1918–2016), a prominent Jewish community leader and mentor |
| Hobbies | Philanthropy, family time, real estate investment, public speaking, hospitality innovation |
| Current Work | Investor, philanthropist, activist, and speaker |
| Years Active | 1980s–present |
| Net Worth (est. 2026) | Approximately $500 million |
Early Life & Education
Stephen J. Cloobeck was born on October 26, 1961, and raised in Encino, California, in a Jewish family that stressed community involvement, personal accountability, and hard work. His father, Sheldon H. Cloobeck, served as president of Stephen Wise Temple in Los Angeles and remained a lifelong hero and mentor to Stephen. Growing up, Cloobeck attended both public and private schools and spent summers in Simi Valley, Sanger, and Willits, California.
Initially dreaming of becoming a heart surgeon, he volunteered as a researcher at Cedars-Sinai Medical Center. He later discovered he had undiagnosed dyslexia, which shaped his creative problem-solving style. Cloobeck graduated from Brandeis University in 1983 with a B.S. in Psychobiology (biopsychology). He credits his neuroscience and psychology studies with influencing his leadership and understanding of people—skills he later applied in building large teams in hospitality.
Career Journey
Early Real Estate Ventures
After college, Cloobeck entered real estate development in Southern California during the 1980s. He built shopping centers in areas including Burbank, Bakersfield, Hanford, Hemet, Buena Park, and Mission Viejo. These early projects gave him hands-on experience in design, development, finance, and operations. He has openly discussed starting some ventures “negative $20 million” due to bold risks that eventually paid off.
Founding Diamond Resorts International
In the early 1990s, Cloobeck moved into hospitality, opening the Polo Towers on the Las Vegas Strip. In 2007, he acquired the publicly traded Sunterra Corporation and transformed it into Diamond Resorts International. Under his leadership as founder, chairman, and CEO, the company expanded rapidly to include more than 370 resorts across over 30 countries, serving hundreds of thousands of vacation owners. It emphasized member experiences and became one of the world’s largest vacation ownership companies.
Cloobeck also served as the inaugural chairman of Brand USA (promoting U.S. tourism) and chaired the Nevada Athletic Commission. He created the Diamond Resorts employee crisis fund (later a foundation) to support team members in hardship—an initiative featured on Undercover Boss.
Undercover Boss and Public Recognition
Starting in 2012, Cloobeck appeared multiple times on CBS’s Undercover Boss, working disguised in entry-level roles at his properties. He awarded more financial support to employees than any other boss in the show’s history, funding education, debt relief, and family needs. These episodes highlighted his hands-on style and generosity.
Company Sale and Later Activities
In 2016, Cloobeck stepped down as Diamond Resorts was sold to Apollo Global Management for $2.2 billion in cash (some reports reference related enterprise values around $3.3 billion). As majority stakeholder with roughly 22% equity, he received approximately $500 million. The company later became associated with Hilton Grand Vacations.
Post-sale, Cloobeck focused on philanthropy, investing, speaking, and public service. He advised during the Obama Administration on economic growth and small business. He has authored or contributed to discussions on hospitality-driven leadership.
Career Highlights
- Built Diamond Resorts into a global leader with 370+ resorts in 30+ countries
- Multiple Undercover Boss appearances with record employee giving
- Founded employee support foundation
- Real estate developments across California
- Roles in tourism promotion and Nevada Athletic Commission
Personal Life
Stephen Cloobeck has been married twice. His first marriage to Heather Cloobeck lasted 13 years. In 1997, he married Canadian model Chantal Leduc (a 1993 Star Search winner); they had three children together before divorcing in 2018 amid custody matters. Cloobeck speaks warmly about fatherhood and the influence of his late father’s lessons on family and integrity.
As of early 2026, he became engaged to Adva Lavie (also known as Mia Ventura or Shoshana), a former Israeli OnlyFans model and Penthouse Pet. Their planned June 2026 wedding near the Western Wall in Jerusalem has faced significant challenges due to legal proceedings against Lavie involving allegations of theft and burglary targeting wealthy individuals. Reports indicate house arrest, an ankle monitor, passport restrictions, and a not-guilty plea, putting the wedding in jeopardy. Cloobeck has maintained a high-profile lifestyle with luxury properties, including a Beverly Hills mansion called “Papillon,” a Cabo San Lucas home, and former residences in Laguna Beach.
He remains close to his three grown children and emphasizes family as a core value.
Dating History / Affairs
Public attention centers on his two marriages and the 2026 engagement to Adva Lavie. Divorce proceedings with Chantal Leduc were noted in media, but no other major public relationships are widely documented outside these.
Controversies
Cloobeck has faced scrutiny over personal and political matters. His 2018 divorce involved custody issues. In 2026, his engagement to Adva Lavie drew extensive coverage due to her legal troubles, including accusations of burglarizing or scamming wealthy older men. Politically, he made headlines in 2017 for warning Democratic leaders he would “cut your money off” if they criticized billionaires. He briefly ran for California governor in 2025–2025 as a Democrat, dropped out in November 2025 to endorse Eric Swalwell, then publicly cut ties in April 2026 after sexual misconduct allegations against Swalwell surfaced, calling himself libertarian-leaning and expressing frustration with the party. He also sought to recover a $1 million donation in related reports.
Awards & Achievements
- Transformed Diamond Resorts into a global hospitality leader sold for billions
- Record employee support through Undercover Boss and the crisis foundation
- Founding chairman of Brand USA for U.S. tourism promotion
- Recognized for job creation, philanthropy, and real estate development
- Speaker and author on hospitality-driven leadership and business thinking
Physical Statistics
Stephen Cloobeck presents as fit and energetic in his mid-60s. Exact height and weight are not publicly detailed, but he appears active in public appearances and maintains a polished, professional image.
Quotes
“If you’re chasing money… Money won’t buy you happiness. I have crazy f*ck you money.” — reflecting on wealth after the Diamond Resorts sale
“I started with negative $20 million… Try that party trick.” — on early business risks
“Human capital is the greatest asset in any organization.” — on the importance of people in business
Favorites
- Core Value: Integrity, hard work, and giving back
- Focus: Family, employee support, and practical solutions to big problems
- Pastime: Sharing entrepreneurial lessons and supporting community causes
Earnings
Stephen Cloobeck’s estimated net worth in 2026 is approximately $500 million, primarily from his roughly 22% stake in the 2016 $2.2 billion sale of Diamond Resorts to Apollo Global Management. Additional wealth comes from real estate holdings (including high-value properties in Beverly Hills and Cabo San Lucas), prior ventures, investments, and speaking engagements. Some sources note he claims billionaire status, though $500 million remains the most consistently cited figure tied to the landmark transaction.
Interesting Facts
- He discovered his dyslexia after graduating college, crediting it with fostering unique thinking that aided his success.
- He once aspired to be a heart surgeon and volunteered in research at Cedars-Sinai.
- On Undercover Boss, he gave more financial help to employees than any other featured boss.
- He helped rename Las Vegas airport in honor of Sen. Harry Reid.
- Briefly entered the crowded 2026 California governor’s race with a pro-business message before withdrawing.
Did You Know Already?
Stephen Cloobeck started his career building shopping centers in California and once described beginning some ventures deeply in debt—yet turned that into a multi-billion-dollar hospitality empire.
Social Media Links
- Instagram: @stephenjcloobeck – shares family moments, business insights, and activism
- Official Website: stephenjcloobeck.com – details on his career, philanthropy, and initiatives
Frequently Asked Questions
How old is Stephen Cloobeck in 2026?
He is 64 years old, born on October 26, 1961, and will turn 65 later in the year.
What is Stephen Cloobeck’s net worth?
His net worth is estimated at around $500 million, largely from the 2016 sale of Diamond Resorts International.
Who is Stephen Cloobeck engaged to in 2026?
He is engaged to Adva Lavie, a former model, though their planned June 2026 wedding has faced significant legal and media challenges.
What happened with Stephen Cloobeck’s California governor campaign?
He announced his candidacy in late 2024/early 2025 as a Democrat, dropped out in November 2025 to endorse Eric Swalwell, and later distanced himself from Swalwell and the Democratic Party, describing himself as libertarian-leaning.
Why is Stephen Cloobeck famous?
He is recognized for founding and growing Diamond Resorts before its billion-dollar sale, his generous Undercover Boss moments, philanthropy, and involvement in California politics.
Conclusion
From real estate roots in California to building a global timeshare empire and a high-profile post-business life, Stephen Cloobeck embodies bold entrepreneurship mixed with public generosity and political engagement. Whether through employee support initiatives, family devotion, or outspoken commentary on business and politics, he continues to draw attention as a self-made leader navigating success, challenges, and public scrutiny. If you found this biography insightful, feel free to share it with others interested in business success stories, hospitality history, or California politics.
