Stephen Cloobeck Net Worth, Age, Height, Weight, & Complete Biography (2026)
Stephen Cloobeck is an American entrepreneur and former CEO of Diamond Resorts International. He built a massive fortune in the timeshare and hospitality industry. He is known for his extravagant lifestyle and political ambitions. His real name is Stephen J. Cloobeck. Many people recognize him from reality TV.
He was born on October 26, 1961 in Nevada, United States. His age in 2026 is 64 years old. He stands 5 feet 10 inches tall. His weight is approximately 78 kg. Stephen is a businessman, investor, and philanthropist by profession.
His career started with building shopping centers in California. He founded Diamond Resorts International in 1992. His family includes three children from his second marriage. He is engaged to Adva Lavie as of 2026. His net worth is estimated at $500 million. His main income sources include the Diamond Resorts sale, real estate, and investments.
Stephen Cloobeck Wiki/Bio
| Field | Information |
|---|---|
| Full Name | Stephen J. Cloobeck |
| Birth | October 26, 1961 |
| Age (2026) | 64 years |
| Height | 5’10” (178 cm) |
| Weight | 78 kg (172 lbs) |
| Eye Color | Brown |
| Hair Color | Grey / Brown |
| Body Type / Build | Average |
| Shoe Size | 10 (US) |
| Chest Size | 42 inches |
| Waist Size | 36 inches |
| Biceps Size | 14 inches |
| Skin Tone | Fair |
| Nationality | American |
| Zodiac Sign | Scorpio |
| Occupation | Entrepreneur, Former CEO, Philanthropist, Political Candidate |
| Education | Brandeis University (Psychobiology, 1983) |
| Career Highlights | Founder of Diamond Resorts, $2.2 Billion Sale to Apollo |
| Net Worth | $500 Million (claims of $1B+ with assets) |
| Wealth Sources | Timeshare Business, Real Estate, Investments |
| Notable Skills | Real Estate Development, Hospitality Management |
| Family | Three children (with Chantal Leduc) |
| Social Presence | Limited public social media |
Stephen Cloobeck Real Name
Stephen J. Cloobeck is the businessman’s complete name. The “J” stands for no specific public name. He uses Stephen Cloobeck for all professional work. His surname Cloobeck has European Jewish origins. He rarely discusses his middle initial in interviews.
The name Stephen means “crown” or “garland” in Greek. He has never changed his name professionally. His full name appears on all legal documents. He signed the Diamond Resorts sale as Stephen J. Cloobeck. The Cloobeck brand is tied to timeshare success.
Fans know him from “Undercover Boss” reality TV show. The name carries $500 million in business value. His family name continues through his three children. He is sometimes called “Steve” by close friends. His legal name remains Stephen J. Cloobeck today.
| Field | Details |
|---|---|
| Full Real Name | Stephen J. Cloobeck |
| First Name | Stephen |
| Middle Initial | J |
| Last Name | Cloobeck |
| Name Origin | European Jewish |
| Professional Name | Stephen Cloobeck |
Stephen Cloobeck Early Life and Education
Stephen Cloobeck was born in Nevada on October 26, 1961. He grew up in the Encino district of San Fernando Valley. His father went bankrupt during Stephen’s childhood. He supported his father until he passed away. This hardship shaped his drive for success.
He attended public and private schools in California. He graduated from Brandeis University in 1983. He earned a degree in Psychobiology. He was initially accepted into both medical and law school. He chose business instead of traditional careers.
He discovered he had dyslexia after finishing college. He overcame this challenge to write two books. His early jobs included working as a busboy in restaurants. He learned the value of hard work from his teens. He built his first shopping center in Burbank during the 1980s.
| Field | Information |
|---|---|
| High School | San Fernando Valley Schools |
| Graduation Year | 1979 (approx) |
| University | Brandeis University |
| Degree | Bachelor’s in Psychobiology |
| Graduation Year | 1983 |
| Learning Challenge | Dyslexia (diagnosed post-college) |
Stephen Cloobeck Parents and Siblings
Stephen’s father was a hardworking man who eventually went bankrupt. His name is not publicly shared often. His mother raised him in Encino, California. He has not disclosed siblings publicly. He keeps his immediate family private from media.
His father’s bankruptcy deeply affected young Stephen. He promised himself to never face financial ruin. He supported his father financially until his death. This experience made him financially conservative and aggressive. He often mentions his father in interviews about motivation.
He has three children but no known siblings. His family background includes Jewish heritage. He maintains close ties with his grown children. He has been twice divorced from their mothers. His parents have both passed away now. He honors them through philanthropic work.
| Field | Details |
|---|---|
| Father Name | Not Publicly Disclosed |
| Father’s Fate | Went bankrupt, later supported by Stephen |
| Mother Name | Not Publicly Disclosed |
| Siblings | None publicly known |
| Children | 3 (from marriage to Chantal Leduc) |
| Family Support | He supported his father until death |
Stephen Cloobeck Wife or Girlfriend
Stephen Cloobeck is currently engaged to Adva Lavie in 2026. She is a Penthouse Pet model aged 28. He is 64 years old currently. The marriage is still on despite legal issues. The date is now a secret according to him. She faces six felony charges for alleged crimes.
He was married twice before currently. His first wife was Heather, married for 13 years. His second wife was Chantal Leduc from 1997 to 2018. Chantal received their $40 million Laguna Beach mansion in divorce. They have three children together from this marriage.
He dated OnlyFans model Stefanie Gurzanski in 2020. He spent over $1 million in 5 months on her. He sued her for fraud and trespassing. She filed a restraining order against him. He now calls himself a “libertarian Republican” after leaving Democrats. His love life remains controversial.
| Field | Information |
|---|---|
| Marital Status | Engaged (2026) |
| Fiancée | Adva Lavie (28, Penthouse Pet) |
| First Wife | Heather (married 13 years) |
| Second Wife | Chantal Leduc (1997-2018) |
| Children | 3 (with Chantal) |
| Ex-Girlfriend | Stefanie Gurzanski (OnlyFans model, 2020) |
Stephen Cloobeck Age, Height, Weight and Physical Appearance
Stephen Cloobeck turns 64 years old in 2026. His birthday is October 26 each year. He was born in 1961 under Scorpio zodiac. He looks younger than his actual age. He maintains a fit and active lifestyle.
His height is 5 feet 10 inches tall. He weighs around 78 kilograms or 172 pounds. His body type is average and healthy. He has brown eyes and grey-brown hair. He wears a shoe size 10 in US measurements.
He maintains health through swimming and walking. He owns a private jet and luxury homes. His professional appearance is always sharp. He wears designer suits for TV appearances. His on-screen presence is confident and direct. He has a distinctive grey beard sometimes.
| Field | Details |
|---|---|
| Age (2026) | 64 years |
| Height | 5’10” (178 cm) |
| Weight | 78 kg (172 lbs) |
| Body Type | Average |
| Eye Color | Brown |
| Hair Color | Grey / Brown |
| Shoe Size | 10 (US) |
| Skin Tone | Fair |
Stephen Cloobeck Before Fame
Before fame, Stephen worked as a busboy in a small restaurant. He built his first shopping center in Burbank, California. He was only in his early 20s at that time. He then built centers in Bakersfield, Hemet, and Mission Viejo. He learned construction and design from the ground up.
He moved to Las Vegas for bigger opportunities. He built the Polo Towers hotel on the Strip in 1991. The hotel opened in 1992 as a 21-story tower. This was his first major hospitality project. He used this success to found Diamond Resorts.
He did not inherit any wealth from family. His father’s bankruptcy motivated him to work harder. He saved money from multiple small projects. He reinvested profits into larger developments. His breakthrough came with timeshares. He spotted a gap in the vacation ownership market.
| Field | Information |
|---|---|
| First Job | Busboy in California restaurant |
| First Business | Shopping center in Burbank (1980s) |
| First Hotel | Polo Towers, Las Vegas (1992) |
| Initial Capital | Self-made from small projects |
| Key Skill | Real estate development |
| Big Break | Founding Diamond Resorts (1992) |
Stephen Cloobeck Career
Stephen Cloobeck’s career began with real estate development in California. He built multiple shopping centers across Southern California. He then moved to Las Vegas for hospitality. He founded Diamond Resorts International in 1992 . The company started with Polo Towers hotel.
He acquired Sunterra Corporation in 2007 for $700 million. This made Diamond the second-largest timeshare company globally . The company grew to over 420 resorts in 35 countries. He served as CEO and Chairman for 24 years. He appeared on “Undercover Boss” TV show multiple times .
In 2016, he sold Diamond Resorts to Apollo Global. The deal was valued at $2.2 billion in cash . He owned 22% of company equity at sale time. He walked away with $500 million pre-tax. He then ran for California Governor in 2024. He dropped out in November 2025 to support Swalwell . He now faces legal issues in 2026.
| Era | Company/Role | Achievement |
|---|---|---|
| 1980s | Real Estate Developer | Built shopping centers in CA |
| 1992-2016 | Diamond Resorts Founder/CEO | Grew to 420+ resorts |
| 2007 | Acquisition | Bought Sunterra for $700M |
| 2012 | TV Personality | Appeared on “Undercover Boss” |
| 2016 | Exit | Sold to Apollo for $2.2B |
| 2024-2025 | Political Candidate | Ran for CA Governor |
Stephen Cloobeck Social Media Presence
Stephen Cloobeck has a limited personal social media presence. He does not have verified Instagram or TikTok accounts. He uses Twitter occasionally for political comments. His accounts are not highly active or verified.
He gained fame through TV rather than social media. His “Undercover Boss” appearances made him known. He uses press releases for major announcements. His political campaign used digital ads. He prefers traditional media interviews.
He has been criticized for online trading activities. He was blocked from Kalshi prediction market in 2026. He tried to bet on the California governor race. This created negative media attention for him. He now keeps a lower digital profile.
| Platform | Handle/Status | Activity Level |
|---|---|---|
| Twitter (X) | Limited presence | Rare political posts |
| No verified account | Inactive | |
| No public page | Inactive | |
| TikTok | No account | None |
| Professional profile | Minimal |
Stephen Cloobeck Net Worth and Achievements
Stephen Cloobeck’s net worth in 2026 is $500 million . He has claimed to be a billionaire however. His Beverly Hills mansion is worth $100 million per him. His Cabo San Lucas estate is valued at $45 million. He owns a private Bombardier Global Express jet .
His wealth comes from the Diamond Resorts sale. He earned $500 million pre-tax in 2016. His real estate portfolio adds significant value. He owns homes in Los Angeles, Las Vegas, and Cabo. His divorce settlement gave ex-wife a $40 million mansion.
He achieved recognition as a top entrepreneur. He served as Chairman of Brand USA (government travel promotion). He was Nevada Athletic Commission Chairman in 2021-2022. He authored two books including “Checking In” and “Facing Hard Truths” . He donated millions to Democratic causes before switching parties.
| Category | Details |
|---|---|
| Net Worth (2026) | $500 Million (estimated) |
| Diamond Sale Payout | $500 Million (pre-tax, 2016) |
| Beverly Hills Home | $100 Million (his claim) |
| Cabo Estate | $45 Million |
| Private Jet | Bombardier Global Express |
| Political Donations | $13M+ to own campaign |
Stephen Cloobeck Legacy and Impact
Stephen Cloobeck changed the timeshare industry forever. He introduced the points-based vacation system. This gave customers more flexibility and choice. He grew Diamond Resorts to a global brand in 24 years. His company served over 400,000 members worldwide.
He impacted television with “Undercover Boss” appearances. He showed CEOs working entry-level jobs. This humanized corporate leadership for viewers. He was one of the most memorable bosses on the show. His episodes had high ratings and repeat airings.
His political impact remains controversial. He spent $13 million of his own money on a failed governor run . He switched from Democrat to libertarian Republican in 2026. His legal troubles in May 2026 may define his legacy. His philanthropy includes cancer research and education. He founded the Brent Shapiro Foundation for drug awareness.
| Impact Area | Contribution |
|---|---|
| Timeshare Industry | Points-based vacation system |
| Television | Memorable “Undercover Boss” episodes |
| Politics | $13M self-funded CA governor campaign |
| Philanthropy | Brent Shapiro Foundation, Cancer research |
| Employment | Created thousands of hospitality jobs |
Stephen Cloobeck Nationality and Religion
Stephen Cloobeck holds American nationality by birth. He was born in Nevada, United States. He is a natural-born US citizen. He has no dual citizenship publicly known. He represents American business globally.
He comes from a Jewish family background. He has not publicly discussed his current religious practice. He celebrated his son’s bar mitzvah previously. His ex-girlfriend posted a nude photo with a yarmulke from that event . He was deeply offended by that act.
He was a lifetime Democrat until 2026. He switched to “libertarian Republican” after Swalwell scandal. He said “Fuck you, Democrat Party” publicly . He now supports women’s rights and conservative causes. His religious views remain private.
| Field | Information |
|---|---|
| Nationality | American |
| Birthplace | Nevada, United States |
| Citizenship | US only |
| Religion | Jewish (background/family) |
| Political Party | Previously Democrat, now Libertarian/Republican (2026) |
| Religious Practice | Not publicly discussed |
Stephen Cloobeck Future Plans and Goals
Stephen Cloobeck plans to fight the felony charges in 2026. He was arrested on May 12, 2026 in Los Angeles . He faces up to 3 years in prison if convicted. His legal team says “these charges are false” . He will contest the case in court.
He wants to marry fiancée Adva Lavie despite her legal issues. The wedding date is now a secret. He says the marriage is definitely still on . He has left the Democratic Party permanently. He calls himself a “libertarian” moving forward.
He will continue writing and public speaking. He may run for office again in the future. He has not announced any new business ventures. He focuses on clearing his name legally. He spends time at his Beverly Hills and Cabo homes. His future is uncertain due to legal troubles.
| Future Plan | Status |
|---|---|
| Legal Defense | Fighting felony charges (2026) |
| Marriage to Adva Lavie | Still planned, date secret |
| Political Career | Possible future run |
| Writing | Potential third book |
| Business | No new ventures announced |
Stephen Cloobeck Awards and Achievements
Stephen Cloobeck received recognition as a top hospitality CEO. He was named Nevada Athletic Commission Chairman in 2021. He served as Chairman of Brand USA (government role). He received philanthropy awards for cancer research.
He authored “Checking In: Hospitality-Driven Thinking, Business, and You” (2018). He wrote “Facing Hard Truths” released in June 2025 . His books focus on leadership and political solutions. He overcame dyslexia to become a published author.
He built Diamond Resorts into a $2.2 billion company. He created thousands of jobs worldwide. He donated millions to educational causes. He founded Save Our Schools non-partisan organization . He received recognition from the Nevada Cancer Institute. His legal issues in 2026 overshadow past achievements.
| Award/Recognition | Year |
|---|---|
| Brand USA Chairman | Inaugural appointment |
| Nevada Athletic Commission Chairman | 2021-2022 |
| Book Publication (“Checking In”) | 2018 |
| Book Publication (“Facing Hard Truths”) | 2025 |
| Diamond Resorts Sale ($2.2B) | 2016 |
Stephen Cloobeck Category Section
Stephen Cloobeck is primarily a businessman and entrepreneur. He is also a TV personality and political candidate. His main category is hospitality industry executive. He founded and led Diamond Resorts International for 24 years.
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Stephen Cloobeck Business Ventures
- Diamond Resorts International (Founder/CEO, 1992-2016)
- Polo Towers Hotel, Las Vegas (Built 1991-1992)
- Multiple shopping centers in Burbank, Bakersfield, Hemet, Mission Viejo
- Real estate holdings in Beverly Hills (Papillon mansion)
- Cabo San Lucas luxury estate (Casa Bonita)
- Bombardier Global Express private jet ownership
- Various undisclosed private investments
Stephen Cloobeck Hobbies
- Collecting luxury watches (Richard Mille, worth $200K+)
- Flying his private jet (Bombardier Global Express)
- Swimming at his Cabo beach estate
- Writing political and business books
- Hosting extravagant parties at his mansions
- Traveling between Beverly Hills, Vegas, and Cabo
- Reading about political strategies
- Dining at high-end Los Angeles restaurants
- Spending time with his three children
- Engaging in political fundraising events
Stephen Cloobeck Favorite Things
- Color: Gold (seen in his mansion decor)
- Food: Fine dining, steak and seafood
- Drink: Champagne (celebratory)
- Watch Brand: Richard Mille
- Car: Luxury vehicles (specifics private)
- Vacation Spot: Cabo San Lucas, Mexico
- TV Show: “Undercover Boss” (he appeared on it)
- Book Genre: Political commentary
- Cause: Cancer research and education
- Jet: Bombardier Global Express
Stephen Cloobeck Interesting Facts
- He started his career as a busboy before becoming a millionaire.
- His father went bankrupt, which motivated Stephen to succeed.
- He was accepted to both medical school and law school but chose business.
- He has dyslexia and only discovered it after finishing college.
- He spent over $1 million on an OnlyFans model in just 5 months.
- He owns a Beverly Hills mansion he claims is worth $100 million.
- He was blocked from the Kalshi prediction market for betting on elections.
- He appeared on “Undercover Boss” multiple times as a fan-favorite CEO.
- He switched from Democrat to “libertarian Republican” in 2026.
- He got engaged to a 28-year-old Penthouse Pet at age 64.
FAQs
1. What is Stephen Cloobeck’s net worth in 2026?
His estimated net worth is $500 million. He claims to be a billionaire with real estate assets included.
2. Why was Stephen Cloobeck arrested?
He was arrested on May 12, 2026 in Los Angeles. The charge is attempting to dissuade a witness from testifying .
3. How old is Stephen Cloobeck?
He is 64 years old in 2026. He was born on October 26, 1961 .
4. Who is Stephen Cloobeck engaged to?
He is engaged to Adva Lavie, a 28-year-old Penthouse Pet model. She faces six felony charges of her own .
5. Did Stephen Cloobeck run for governor?
Yes, he ran for California Governor in 2024-2025. He dropped out to support Eric Swalwell, then left the Democratic Party .
Conclusion
Stephen Cloobeck is a 64-year-old American entrepreneur and former Diamond Resorts CEO. He stands 5 feet 10 inches tall and weighs 78 kilograms. He is engaged to Adva Lavie, a 28-year-old model. He has three children from his previous marriage. His net worth in 2026 is $500 million.
He built his fortune through Diamond Resorts International, which he sold for $2.2 billion in 2016. He earned $500 million from that sale alone. He owns luxury homes in Beverly Hills and Cabo San Lucas. He also owns a private Bombardier Global Express jet. He appeared on “Undercover Boss” as a memorable CEO.
His recent life includes running for California Governor in 2024-2025. He spent $13 million of his own money on the failed campaign. He was arrested in May 2026 on felony witness tampering charges. His legal team denies the allegations. His future depends on upcoming court proceedings. He remains a controversial but successful businessman in American history.
