Cloobeck ’83 Endowed Fellowship at the Brandeis University International Business School. He acquired the publicly-traded Sunterra Corporation in April 2007, and he converted this into the multi-million dollar vacation ownership company now known as Diamond Resorts International.Click to see full answer. Also know, how much is Stephen Cloobeck worth?Stephen Cloobeck net worth: Stephen Cloobeck is the Chairman and CEO of the Las Vegas corporation Diamond Resorts Holdings Inc who has a net worth of $100 million.One may also ask, who owns Diamond Resorts now? Apollo Global Management Beside above, who gave the most money on Undercover Boss? Cloobeck — the only boss to undergo the ” ‘Undercover’ journey” twice — has contributed $2 million to his workers, $1 million of which came from his own pocket. He’s paid for a worker’s life-saving cancer treatments, as seen in the video above. And he’s also created a special crisis fund for all his 5,600 employees.How do I sell my diamond timeshare?With SellMyTimeshareNow.com, you can purchase a timeshare resale for up to 70% off retail prices and become part of the exclusive Diamond Resorts International® network. Our Diamond specialists can help you with any questions you might have about renting or purchasing Diamond timeshares on the resale market.