Stephen Cloobeck Biography: Age, Wife, Family, Diamond Resorts, Net Worth, Undercover Boss, 2026 California Governor Run in 2026

Stephen Cloobeck is a self-made American entrepreneur and philanthropist best known as the founder, former chairman, and CEO of Diamond Resorts International, the global timeshare and vacation ownership company he built into a powerhouse with hundreds of properties worldwide. Born in 1961, the 64-year-old businessman turned a struggling company into a major hospitality brand before selling it in a multi-billion-dollar deal in 2016. He gained national attention through his generous appearances on the CBS reality show Undercover Boss and has since become active in politics, briefly running for California governor in 2026 while navigating high-profile personal life headlines. His story blends business success, family values, and public service with notable personal challenges.

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; Undercover Boss appearances; 2016 company sale; philanthropy and 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 reported legal issues affecting wedding plans)
Previous Spouses	Heather Cloobeck (first marriage, 13 years); Chantal Leduc (Canadian model, 1997–2018)
Children	Three (with Chantal Leduc)
Family Tree	Son of Sheldon H. Cloobeck (1918–2016), prominent Jewish community leader and mentor
Hobbies	Philanthropy, family time, real estate investment, public speaking
Current Work	Investor, philanthropist, political commentator; previously involved in hospitality and government service
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 emphasized community involvement and personal accountability. His father, Sheldon H. Cloobeck, served as president of Stephen Wise Temple in Los Angeles and became a lifelong mentor and hero to Stephen. Growing up, Cloobeck attended public and private schools and spent summers in various California locations, including Simi Valley, Sanger, and Willits.

Initially aspiring to become a heart surgeon, he volunteered as a researcher at Cedars-Sinai Medical Center. He later pivoted from medicine and law after discovering he had undiagnosed dyslexia, which forced him to develop unique problem-solving approaches. Cloobeck graduated from Brandeis University in 1983 with a B.S. in Psychobiology (also referred to as biopsychology). He credits his studies in neuroscience and psychology with shaping his leadership style and entrepreneurial mindset.

Career Journey

Early Career and Real Estate Beginnings

After college, Cloobeck entered real estate development in California during the 1980s. He built shopping centers and gained hands-on experience in design, development, finance, and operations—skills that later defined his hospitality empire. He decided against a medical career and focused on business, starting with limited resources (he has mentioned beginning “negative $20 million” in some ventures due to early risks).

Founding and Growth of Diamond Resorts International

In 1992, Cloobeck founded Diamond Resorts International, focusing on vacation ownership and timeshares. A pivotal move came in April 2007 when he acquired the publicly traded Sunterra Corporation and rebranded and transformed it into Diamond Resorts. Under his leadership as chairman and CEO, the company expanded dramatically to operate more than 370 resorts across 33+ countries, including properties in the U.S., Hawaii, Mexico, the Caribbean, Europe, Asia, and beyond. It became one of the world’s largest vacation ownership companies, employing tens of thousands and emphasizing member experiences.

Cloobeck also served as the inaugural chairman of Brand USA Inc. and chaired the Nevada Athletic Commission. In 2012, he created the Diamond Resorts International Team Member Crisis Fund (later a foundation) to support employees facing personal hardships—an initiative highlighted during his Undercover Boss episodes, where he anonymously worked entry-level jobs and rewarded dedicated staff with life-changing gifts like education funding and debt relief.

Sale of Diamond Resorts and Post-Business Life

In June 2016, Cloobeck stepped down as the company was sold to Apollo Global Management for $2.2 billion in an all-cash deal (some reports reference higher enterprise values around $3.3 billion in related discussions). As majority stakeholder with roughly 22% equity, he received approximately $500 million from the transaction. Today, Diamond Resorts is associated with Hilton ownership.

Post-sale, Cloobeck has focused on philanthropy, investing, public speaking, and politics. He served in advisory roles during the Obama Administration on economic growth and small business support. In late 2024/early 2025, he announced a bid for California governor in 2026 but later dropped out and endorsed Congressman Eric Swalwell before shifting political affiliations toward libertarian-leaning views and criticizing certain Democratic positions.

Career Highlights

Built Diamond Resorts from acquisition to global leader with 300+ properties
Featured on multiple Undercover Boss episodes, showcasing employee generosity
Founded employee crisis support foundation
Over 40 years in hospitality, real estate, and operations
Political and philanthropic contributions, including major Democratic donations (later distanced)

Personal Life

Stephen Cloobeck has been married twice. His first marriage to Heather Cloobeck lasted 13 years. In 1997, he married Canadian model and Star Search winner Chantal Leduc; they had three children together before divorcing in 2018 amid custody proceedings. He has spoken warmly about fatherhood and the influence of his own father’s lessons on family and leadership.

As of early 2026, Cloobeck was engaged to Adva Lavie, a former Israeli OnlyFans model and Penthouse Pet, though reports indicated legal issues and a “not guilty” plea in related matters created challenges for wedding plans. He maintains a high-profile lifestyle with luxury real estate holdings, including a Beverly Hills property known as “Papillon,” a Cabo San Lucas home, and former residences in Laguna Beach.

Cloobeck is a devoted father and remains involved in charitable causes. He has emphasized integrity, hard work, and giving back as core values.

Dating History / Affairs
Public records primarily highlight his two marriages and the 2026 engagement. No other major public affairs are widely documented outside divorce proceedings.

Controversies

Cloobeck has faced scrutiny over personal matters, including his 2018 divorce and 2026 engagement-related headlines involving legal allegations against his fiancée. Politically, he drew attention for threatening to withhold donations from Democrats if they criticized “billionaires” (2017 MSNBC comments) and later distancing himself from the party, cutting ties with figures like Eric Swalwell, and describing himself as libertarian-leaning. His brief 2026 gubernatorial run and subsequent dropout also generated media coverage. Business dealings, while generally praised for growth, occasionally faced typical industry critiques common in timeshares.

Awards & Achievements

Transformed a public company into a global hospitality leader sold for billions
Created employee support foundation still aiding Diamond Resorts team members
Recognized for philanthropy and job creation
Featured on Undercover Boss for hands-on leadership and generosity
Major donor to political and community causes; Brandeis University supporter (including neuroscience research donations)

Physical Statistics

Stephen Cloobeck maintains an active presence in his mid-60s. Specific height and weight details are not publicly available, but he presents as fit and energetic in public appearances and social media.

Quotes

“If you’re chasing money, listen to this… Money won’t buy you happiness. I have crazy f*ck you money.” — reflecting on wealth after his company sale

“I started with negative $20 million… Try that party trick.” — on early business risks and turnaround

“My father’s lessons have made me a better business leader, father, and community member.”

Favorites

Focus: Family, integrity in business, and helping others
Pastime: Real estate, philanthropy, and sharing lessons from entrepreneurship
Value: Human capital as the greatest asset in any organization

Earnings

Stephen Cloobeck’s estimated net worth stands at approximately $500 million as of 2026, largely derived from his roughly 22% stake in the 2016 Diamond Resorts sale to Apollo Global Management. Additional wealth comes from real estate investments, prior hospitality ventures, and speaking/philanthropic activities. Some sources occasionally reference higher enterprise values or varying estimates, but $500 million remains the most consistent figure tied to the landmark transaction.

Interesting Facts

He discovered his dyslexia after college, crediting it with fostering creative thinking that aided his entrepreneurial success.
On Undercover Boss, he personally funded education, daycare, and more for hardworking employees.
Started in real estate building shopping centers before dominating the timeshare industry.
Served on the Nevada Athletic Commission and advised on national tourism branding.
Briefly entered the 2026 California governor race as a self-described problem-solver focused on affordability and livability.

Did You Know Already?

Stephen Cloobeck once volunteered in heart research at Cedars-Sinai with dreams of becoming a surgeon before pivoting to business—and he later donated $1 million to Brandeis University for intelligence and neuroscience research.

Instagram: @stephenjcloobeck – shares on family, business insights, philanthropy, and activism (over 100K followers)
Official Website: stephenjcloobeck.com – details on his career and initiatives
No widely confirmed active personal X/Twitter or Facebook accounts prominently listed; professional updates often appear via news or his site.

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, primarily from the 2016 sale of Diamond Resorts International.

Who was Stephen Cloobeck married to?
He was previously married to Heather Cloobeck and then to model Chantal Leduc (1997–2018), with whom he has three children. In 2026, he was engaged to Adva Lavie.

What happened with Stephen Cloobeck’s California governor run?
He announced a candidacy for the 2026 race but later dropped out and endorsed Eric Swalwell before shifting toward more libertarian views and distancing from some Democratic ties.

Why is Stephen Cloobeck famous?
He is recognized for founding and selling Diamond Resorts in a major deal, his generous Undercover Boss moments, philanthropy, and high-profile business and personal life.

Conclusion

From humble California roots and overcoming dyslexia to building a global hospitality empire and cashing out in a billion-dollar exit, Stephen Cloobeck exemplifies self-made success blended with generosity and public engagement. Whether through employee support initiatives, family devotion, or political commentary, he continues to draw attention as an entrepreneur who values people and results. If you found this biography insightful, feel free to share it with others interested in business leaders, timeshare history, or California politics.