Stephen J. Cloobeck

Business Visionary | Philanthropist | Activist

Stephen J. Cloobeck earned a reputation as a successful businessman when he built Diamond International Resorts into one of world’s top vacation-ownership companies. Since the company’s sale in 2016, he has pursued other business and philanthropic ventures, and is the former Chairman of the State of Nevada Athletic Commission.

Los Angeles Dream Center thanks entrepreneur and philanthropist Stephen J. Cloobeck for generous donation to help support the Family Floor

LOS ANGELES, June 14, 2023 — The Los Angeles Dream Center, a faith-based nonprofit organization dedicated to transforming lives and the underserved communities of Los Angeles, is pleased to report a second generous donation of $250,000 from entrepreneur and philanthropist Stephen J. Cloobeck. Cloobeck has now donated a total of a half million dollars to the Dream Center over the past two years. Cloobeck has contributed these funds to help support the Family Floor again at the Dream Center campus in Echo Park. The Family Floor is dedicated to helping families overcome chronic homelessness and poverty and ensure they remain together.

Stephen J. Cloobeck Sponsors Crenshaw Family YMCA’s Inaugural ‘Crenshaw Classic’ Track Meet

Entrepreneur and philanthropist Stephen J. Cloobeck was honored to support the Crenshaw Family YMCA’s inaugural “Crenshaw Classic” Track Meet at Crenshaw High School on June 3rd, 2023. The “Classic” continued the YMCA’s historic mission of strengthening individuals and communities across the country through youth development, healthy living and social responsibility. Students who attended the classic participated in sprints for the 50-, 100-, and 200-meter dash and the 400-meter relay, jumped in the long jump, and threw in the softball throw. The Crenshaw Family YMCA has a rich tradition of providing a home for young athletes, including Allyson Felix, the most decorated track and field athlete in Olympic history. Stephen was pleased to join Los Angeles County Supervisor Holly J. Mitchell, Los Angeles City Councilmember Marqueece Harris-Dawson, Assemblymember Isaac G. Bryan, and others in supporting the Crenshaw Family YMCA in this outstanding community event.


Stephen Cloobeck is a real estate developer, vacation ownership entrepreneur, resort operator, and proven investor with a track record of multiple successful business ventures around the world. His best-known creation, Diamond Resorts International, was sold in 2016 for $2.2 billion to Apollo Global Management.


Motivated by a commitment to purpose-driven philanthropy, Stephen Cloobeck believes in supporting programs and organizations with a proven track record in serving their communities.

Government Service & Activism

Stephen Cloobeck doesn’t just back a movement, he fights for it. Whether it’s fighting to rename the Las Vegas Airport after his mentor and friend, the late US Senator Harry Reid, or speaking out about gun control, Stephen gets directly involved in bringing change where it’s needed.
“Stephen is a master communicator with a rare knack for understanding and working with individuals across a wide range of functions . . . (To get a sense of this, go watch him on Undercover Boss.) This is the secret sauce of Stephen’s success - and thereby the source of Diamond Resorts’ success. Stephen cares about his workers and empowers them to take ownership and pride in their efforts. He makes sure they find meaning in their work.”
-Michael Milken

- Recent News -

Checking In:

Hospitality-Driven Thinking, Business, and You

In Checking In, Stephen J. Cloobeck–entrepreneur, investor, philanthropist, and the founder and former CEO and chairman of Diamond Resorts International–invites you to check in with yourself to take stock of where you are, where you want to go, and, most importantly, how to actually get there. (more info»)