Stephen Cloobeck Net Worth: How the Timeshare Mogul Built His $500 Million Fortune

Founder of Diamond Resorts International, Stephen J. Cloobeck reportedly has a net worth of $500 million. Renowned in the timeshare market, Cloobeck became well-known for his commercial sense and Undercover Boss appearances. From real estate development to political aspirant, his path reveals his drive and financial ability.

Early Life and Career

DetailInformation
NameStephen J. Cloobeck
Date of BirthOctober 26, 1961
EducationBrandeis University, Psychobiology (1983)
Early CareerReal Estate Developer
Notable AchievementFounder of Diamond Resorts International

Born in 1961, Cloobeck studied psychobiology at Brandeis University. Originally hoping to be a doctor or lawyer, he turned to real estate development and built Southern California shopping centres. After his travels brought him to Las Vegas, he built the 21-story Polo Towers on the Strip.

Resorts International Diamond: Creating a Legacy

Stephen Cloobeck started Diamond Resorts International in 1992, and it expanded to run more than 370,000 members yearly across 35 countries.

Key MilestonesDetails
Founded1992
Acquired Sunterra2007
Sold to Apollo Global2016, for $2.2 billion
Owner’s EquityCloobeck held 22%, earning $500 million

Under Cloobeck’s direction, Diamond Resorts became a worldwide timeshare powerhouse. He sold the business to Apollo Global Management for $2.2 billion in 2016, therefore generating a $500 million pre-tax gain.

An Expensive Way of Life

Cloobeck’s riches is clear from his opulent way of living, which comprises several high-value homes:

  • Beverly Hills boasts a $100 million house.
  • A 45 million dollar villa in Cabo San Lucas, Mexico.
  • Given to his ex-wife during their divorce, Laguna Beach once housed a $40 million home.
PropertyValue
Beverly Hills Mansion$100 million
Cabo San Lucas Villa$45 million
Laguna Beach Estate$40 million (divorce)

Although Cloobeck is rather wealthy, his claim to be a billionaire is still under dispute since investments and divorces have affected most of his riches.

Personal Life: Obstacles and Relationships

Personal life of Stephen Cloobeck has seen ups and downs, especially in relation to his marriages:

  • Married 13 years, Heather Cloobeck is first wife.
  • Model and former Star Search winner Chantal Leduc married from 1997 to 2018.
  1. Chantal Leduc, a model and former Star Search winner, married from 1997 to 2018.
Personal DetailInformation
Number of Children3
Divorces2
Notable Settlements$40 million Laguna Beach estate

His second divorce came at the time Diamond Resorts was sold, which drastically changed his net worth.

Political Objectives

Cloobeck declared his intention to run for California Governor in 2024. His campaign centres on using his accomplishments as an entrepreneur to solve state-wide issues.

His political activity is probably going to draw more attention to his financial claims, maybe necessitating the provision of comprehensive documentation.

Media Awareness and “Undercover Boss”

Cloobeck became somewhat well-known in 2012 when he appeared on the reality show Undercover Boss.

ShowAppearance Details
Undercover BossSeason 3, Episodes 1 & 2
ImpactHighlighted employee welfare improvements

The program enhanced his reputation by highlighting his commitment to raise standards of working conditions throughout Diamond Resorts.

Corporate Gifts and Philanthropy

Notable philanthropist and supporter of many organisations is Stephen Cloobeck.

InitiativeContribution
Brent Shapiro FoundationFocus on drug awareness and prevention
Brandeis UniversitySignificant endowment for business education
Travel Promotion BoardChairman, promoting US tourism

Cloobeck has also backed other community projects as well as the Nevada Cancer Institute.

Difficulties and Net Worth Discussion

Cloobeck claims to be a billionaire most of the time, yet his financial situation is usually under doubt. Even if the sale of the Diamond Resorts brought in $500 million, divorce settlements and extravagant spending could have lessened his overall riches.

Claimed Net Worth$1 Billion
Verified Net Worth$500 Million (as of 2023)
Debated PointsDivorce impacts, property valuations, taxes

Final Thoughts

The $500 million net worth of Stephen Cloobeck emphasises his hotel sector influence and entrepreneurial achievement. Whether via his political aspirations, Diamond Resorts, or celebrity on reality TV, Cloobeck’s path is evidence of resiliency and creativity.

His financial legacy will surely remain of public interest as he enters the political scene.

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