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About Stephen J. Cloobeck

Most Charitable Undercover Boss

Stephen J. Cloobeck is a self-made entrepreneur with more than thirty years’ experience across every aspect of hospitality design, development, finance and operations. As the founder and former CEO and Chairman of Diamond Resorts International – a business that grew to become the second-largest vacation ownership company worldwide with more than four hundred properties across thirty-three countries in its portfolio – Cloobeck made a name for himself as an advocate for radical customer service, what he calls embracing the “Meaning of Yes.” Diamond was sold to Apollo Global Management in 2016, then sold by Apollo in 2021 to Hilton Grand Vacations. In 2021, Cloobeck was appointed as the Chairman of the State of Nevada Athletic Commission before ending his term in 2022.

For his commitment to serving the hospitality industry and expanding its economic impact nationwide, Cloobeck was appointed by former Commerce Secretary Gary Locke to serve as the inaugural chairman of the board in Brand USA Inc., a US government-formed nonprofit corporation with the sole mission of promoting travel to the United States. As Brand USA’s leading voice, Cloobeck coordinated with the Departments of Homeland Security, State, Commerce, Treasury, Interior, Congress, the White House, and leading American business in a first-ever effort to make the United States a more welcoming and accessible international travel destination efficiently, effectively, and economically for millions of would-be visitors around the globe. He was instrumental in the successful campaign to rename the Las Vegas airport after his longtime friend and mentor, the late U.S. Senator and Senate Majority Leader Harry Reid. Additionally, Cloobeck has recently joined forces with Mayor Karen Bass’ commendable initiative LA4LA. Leveraging his vast expertise in public-private partnerships and his philanthropic endeavors helping families in need, he is spearheading this collaborative effort to unlock stalled affordable housing development for the unhoused and pilot new financing solutions at speed and scale in partnership with the Mayor’s Office.

Appointed by the late former Nevada Governor, Kenny C. Guinn, to the Standing Committee on Judicial Ethics and Election Practices in 2004, Cloobeck concluded his service in August 2007. The Standing Committee was created to resolve ethical disputes that may arise over the course of campaigns for judicial office and to provide judges and aspirants to judicial office advisory opinions regarding ethical matters that may arise in the ordinary course of judicial service or in the elective or appointment process.

Cloobeck supports many charities and civic organizations, including but not limited to the Prostate Cancer Foundation, FasterCures, Keep Memory Alive, the Barack Obama Foundation, the Brent Shapiro Foundation for Drug Prevention, the Los Angeles Dodgers Foundation, the Los Angeles Dream Center, and various educational initiatives. In personal efforts to assist Diamond Resorts team members dealing with unexpected life events, Cloobeck founded the Diamond Resorts International Team Member Crisis Fund (now the Diamond Resorts International Foundation) in 2012, an unprecedented initiative that continues to offer aid to Diamond team members worldwide struggling with personal challenges.

Cloobeck received a degree in psychology from Brandeis University in 1983, only to learn after graduation that he had been grappling with undiagnosed dyslexia all that time. He is the author of the 2018 book, “Checking In: Hospitality-Driven Thinking, Business, and You.”

He grew up in Encino, California and went to public and private schools. Cloobeck spent his summers in Simi Valley, Visalia, and Willits, California. He created his first business in real estate, after deciding not to become a heart surgeon and after working as a volunteer researcher at Cedars Sinai doing heart research. Cloobeck built his first shopping center in the 1980’s in Burbank, California, and others in Bakersfield, Hanford, Hemet, Buena Park, and Mission Viejo to name a few. He currently resides in Beverly Hills, California.