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Stephen Cloobeck

Stephen J. Cloobeck is an American entrepreneur, investor and author who founded Diamond Resorts International and served as its chairman and CEO. He was the inaugural chairman of Brand USA and chaired the Nevada Athletic Commission, appeared on Undercover Boss and previously ran for governor of California.

Contents31 sections
Key facts

Early Life: Growing Up in California

Cloobeck grew up in Encino, California, initially aspiring to surgery before entering property development.⁠[1]

Graduating from Brandeis University

He graduated from Brandeis University after studying biopsychology. His undergraduate thesis advisers were Eve Marder and Arthur Wingfield, and his research concerned Alzheimer’s disease.⁠[2]

Shopping-centre Development and Setbacks

His website recalls starting shopping-centre development at twenty-five. After his Lake Forest contractor and lender failed in the late 1980s, he handled construction, leasing and debt problems.⁠[3]

Polo Towers Opens

Polo Towers opened in Las Vegas. His website credits his father with financing and himself with design, construction and operations.⁠[3]

Diamond Resorts LLC

Securities filings date the formation of Diamond Resorts LLC and its affiliated companies to 1999, describing Cloobeck’s involvement through these businesses in Polo Towers development and the design of Marriott’s Grand Chateau vacation-ownership resort.⁠[4]

Nevada Cancer Institute Board Service

He served on the Nevada Cancer Institute’s board and chaired it during his final year on the board.⁠[4]

Judicial Ethics and Election Practices

He was appointed to Nevada’s Standing Committee on Judicial Ethics and Election Practices in 2004 and served until August 2007.⁠[1]

Acquiring Sunterra

The Diamond Resorts group led by Cloobeck completed its acquisition and merger with Sunterra. Securities filings record cancellation of Sunterra’s common shares at $16 each; the transaction established a major base for expansion of the vacation-ownership business.⁠[5][4]

Chairing the Tourism-promotion Organisation

Commerce Secretary Gary Locke appointed him a director of the Corporation for Travel Promotion in September, and he was elected chairman in October. The organisation subsequently promoted travel to the United States as Brand USA.⁠[4][2]

Two Undercover Boss Appearances

CBS aired his first Undercover Boss episode on January 15 and his return to work undercover at his resorts on November 30. The broadcaster described the second episode as the show’s first returning-boss appearance and announced more than $1 million in employee rewards.⁠[6]

Employee Crisis Fund

He established the Diamond Resorts Team Member Crisis Fund for struggling employees; it later became a foundation.⁠[1]

Stepping Down as CEO

David F. Palmer succeeded him as CEO of Diamond Resorts Parent and its subsidiaries, while Cloobeck remained chairman. The company announced the management change on January 7.⁠[7]

Company IPO

Diamond Resorts International conducted its initial public offering, with the relevant registration statements becoming effective on July 18. Cloobeck continued as chairman.⁠[8]

Apollo Completes the Acquisition

Affiliates of Apollo-managed funds completed the acquisition of all outstanding Diamond Resorts common shares through a $30.25-per-share cash tender offer followed by a merger. This was a corporate equity transaction price, not a measure of Cloobeck’s personal wealth.⁠[9]

Merger-disclosure Litigation Ruling

In Appel v. Berkman, the Delaware Supreme Court reversed dismissal of a shareholder suit and remanded it. The court found disclosures materially incomplete because they omitted Cloobeck’s reasons for abstaining, including dissatisfaction with price and timing; defendants had argued such opinions were immaterial. The ruling addressed disclosure and whether the case could proceed.⁠[10]

Publication of Checking In

He published Checking In: Hospitality-Driven Thinking, Business, and You, drawing on his business experience to discuss leadership and customer service. Brandeis later reported that he donated proceeds to dyslexia research and education.⁠[11][2]

Gift to Brandeis University

The university announced his $1 million gift supporting brain research by Marder and Wingfield, with part intended to help undergraduates attend academic conferences.⁠[2]

Nevada Athletic Commission Chair

Governor Steve Sisolak appointed him chairman of the Nevada Athletic Commission for an intended two-year term.⁠[12]

Federal Copyright Case Dismissed

The federal copyright action he filed against Stefanie Gurzanski in March was dismissed with prejudice by stipulation, with each side bearing its own costs and legal fees. This disposition concerns only copyright case 2:21-cv-02306.⁠[13]

Nathan’s Law Emergency Regulation

Following student Nathan Valencia’s death after a boxing event, the commission adopted an emergency regulation signed by the governor, clarifying supervision and exemption checks for certain collegiate and amateur combat events. Cloobeck announced its implementation as chairman, emphasising participant safety.⁠[14]

Resigning from the Commission

He resigned, stating that he could not work with incoming governor Joe Lombardo. The resignation followed Sisolak’s defeat in his reelection campaign.⁠[12]

Announcing a California Gubernatorial Bid

He announced a bid for California governor in the 2026 election. His campaign release then described him as a lifelong Democrat and emphasised affordability, the business environment and public safety.⁠[15]

School of Hard Knocks Interview

The channel released a home interview titled How I Turned –$20 Million Into $3.3 Billion, discussing early hotel ventures, mentorship, negotiation and his reasons for running for governor. Its description calls him a billionaire but supplies no independently verifiable personal-net-worth calculation.⁠[16]

Publication of Facing Hard Truths

Disruption Books published Facing Hard Truths: How Americans Can Get Real, Pull Together, and Turn Our Country Around. It discusses immigration, crime, living costs and political discourse, advocating cooperation and public trust in addressing policy problems.⁠[17]

Withdrawing and Endorsing Swalwell

He ended his gubernatorial campaign and endorsed Eric Swalwell.⁠[18][19]

Withdrawing Political Support

On April 12, he told NBC Los Angeles that he no longer supported Swalwell following sexual-misconduct allegations, which Swalwell denied. In reporting dated April 14, Cloobeck also publicly stated that he was no longer a Democrat.⁠[19][20]

Surrender in Witness-interference Case

He surrendered in West Hollywood and was released on $300,000 bail. Citing the complaint, NBC reported allegations that he tried to dissuade witnesses in the case of his then-fiancée Adva Lavie, involving three felony counts and one misdemeanor telephone-harassment count. Attorney Elias Dabaie denied the allegations.⁠[21]

Not-guilty Pleas

He pleaded not guilty to all charges. FOX 11 specified two felony counts involving force or threats, one felony count concerning attendance or testimony, and one misdemeanor phone-call count. It also reported that he had ended his engagement to Lavie. These were allegations and procedural developments, not convictions.⁠[22]

Investments and Business Ideas: Customer Service

His website lists a post-sale investment in CLEAR and describes his proactive customer-service approach as The Meaning of Yes.⁠[3]

Official Website and Public Accounts: Verified Links

Sources

  1. About Stephen J. Cloobeck (opens in a new window)
  2. Entrepreneur Gives $1M for Research Into the Workings of the Mind (opens in a new window)
  3. Business (opens in a new window)
  4. Diamond Resorts Corporation — 2012 Form 10-K (opens in a new window)
  5. Diamond Resorts Corporation — First Quarter 2012 Form 10-Q (opens in a new window)
  6. Undercover Boss Features the Return of a Boss (opens in a new window)
  7. Diamond Resorts — Management Changes (opens in a new window)
  8. Diamond Resorts International — 2014 Form 10-K (opens in a new window)
  9. Diamond Resorts International and Apollo Funds Announce Closing (opens in a new window)
  10. Appel v. Berkman — Supreme Court Opinion (opens in a new window)
  11. Checking In: Hospitality-Driven Thinking, Business, and You (opens in a new window)
  12. Stephen Cloobeck Quits Athletic Commission, Slams Lombardo (opens in a new window)
  13. Stephen J. Cloobeck v. Stefanie Gurzanski, 2:21-cv-02306 (opens in a new window)
  14. Nathan’s Law Unanimously Passed by Nevada Athletic Commission (opens in a new window)
  15. Stephen J. Cloobeck Announces Candidacy for California Governor (opens in a new window)
  16. How I Turned –$20 Million Into $3.3 Billion (opens in a new window)
  17. Facing Hard Truths (opens in a new window)
  18. Stephen Cloobeck Ends Bid for California Governor, Endorses Eric Swalwell (opens in a new window)
  19. Stephen Cloobeck Cuts Ties with Eric Swalwell (opens in a new window)
  20. California Billionaire Swaps Party Affiliation to Libertarian-Republican (opens in a new window)
  21. LA-area Billionaire and Eric Swalwell Donor Stephen Cloobeck Arrested on Felony Charges (opens in a new window)
  22. Stephen Cloobeck Pleads Not Guilty to Witness Tampering (opens in a new window)
  23. Stephen J. Cloobeck — YouTube (opens in a new window)
  24. Stephen J. Cloobeck — Historical X Link (opens in a new window)