About the Author

Meet Stephen

Self-Made Business Leader.

A self-made business leader with over 30 years of experience across every aspect of hospitality design, development, and deployment. As the original founder and former CEO and chairman of Diamond Resorts International—a business that grew to become the second largest vacation ownership company worldwide—Cloobeck made a name for himself as the industry’s most adamant advocate for radical customer service, what he calls embracing the Meaning of Yes.

Stephen J. Cloobeck is a self-made entrepreneur with more than thirty years’ experience across every aspect of hospitality design, development, and deployment.

As the original founder and former CEO and chairman of Diamond Resorts International (NYSE:DRII) – 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 the industry’s most adamant advocate for radical customer service, what he calls embracing the Meaning of Yes.

For his commitment to serving the hospitality industry and amplifying its economic impact nationwide, Cloobeck was appointed by 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 Department of Homeland Security, the Department of State, the Department of Commerce, Congress, the White House, and leading American business in a first-ever effort to efficiently, effectively, and economically make the United States a more welcoming and accessible international travel destination for millions of would-be visitors around the globe.

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But to Cloobeck’s own amusement, he is perhaps most frequently recognized for his appearances on CBS’s hit TV show Undercover Boss. Featured on multiple episodes across multiple seasons, Cloobeck to this day ranks as the “most generous boss” who has ever participated in the unscripted program.

Cloobeck works with many charities and civic organizations, including but not limited to: the Prostate Cancer Foundation, FasterCures, Keep Memory Alive, Water.org, the Brent Shapiro Foundation for Drug Prevention, 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 difficulties.

Cloobeck received a degree in psychobiology from Brandeis University in 1983 by the seat of his pants, only to learn after graduation that he had been grappling with undiagnosed dyslexia all that time.

Cloobeck will be donating all of this book’s author proceeds to dyslexia research, education, and supportive causes.