American businessman Stephen Cloobeck is the Chairman and Chief Executive Officer of Diamond Resorts Holdings Inc., and has an estimated net worth of $100 million.

Stephen J. Cloobeck is a graduate of Brandeis University with a degree in Psychobiology in 1983. He acquired the publicly-traded Sunterra Corporation in April 2007, which he converted into Diamond Resorts International, a multi-million dollar vacation ownership company with more than 4,500 employees worldwide. Currently, his Diamond Resorts Holdings owns and operates more than 200 resorts around the world in 25 different countries, with a specialization in time shares. Around 400,000 people use these hotels each year for their vacations.

Mr. Cloobeck is the Chairman of the Board for the US Corporation for Travel Promotion and the Nevada Cancer Institute. He also founded the Brent Shapiro Foundation for Drug Awareness. In 2012, he gave a significant amount to the Brandeis University International Business School. He is very politically active, and has considered running for governor of Nevada in 2007. He is most widely recognized as one of the subjects of the first season of the reality television series Undercover Boss.