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Diamond Resorts CEO Gets His Hands Dirty on “Undercover Boss”

Undercover Boss

Stephen Cloobeck makes a speech just before the world premiere of his episode of Undercover Boss.

How do you get a big-time hospitality CEO to repair an air conditioner (with his own hands), scrape paint off the ceiling, work the booking center and man the front desk? Put him on the CBS reality show “Undercover Boss,” in which the boss poses as a trainee who’s new to the field.

Stephen J. Cloobeck, CEO of Diamond Resorts International, a large timeshare group (200 branded and affiliated resorts with over 27,000 guest beds in 28 countries), invited some of the travel media to watch the world premiere of his “Undercover Boss” episode, which kicks off the 2012 season.

Cloobeck, who said he put up $5.5 million of his own money when he acquired the publicly traded Sunterra Corporation to turn it into the privately-held Diamond Resorts International, was willing to do manual labor to get a different perspective on how his properties are operating.

Central Casting couldn’t have come up with a better CEO. Cloobeck is as intense, driven and passionate as they come — he told us that he wants to be “the greatest hotelier ever” and that “the sky is the limit worldwide.” But this polished, charismatic and somewhat intimidating personality still has enough quirks to make for great TV. One of the most entertaining scenes occurs early on, when his bodyguard places a flashlight and a panic alarm on Cloobeck’s night table right before he rests up for his first assignment: a maintenance man at a newly acquired Sedona resort.

Cloobeck confirmed that the show is completely unscripted and that he made all of his own decisions. The latter is especially easy to believe because I don’t think there’s anyone who could tell this man what to do. The employees do seem very well vetted, as they’re articulate, hard-working-but-down-on-their-luck folks. In this economy, finding people who are struggling isn’t too hard. But these employees open up about their hardships and really tug at the viewers’ — and Cloobeck’s — heartstrings.

The episode will air on Sunday, January 15, 8pm ET, on CBS. I don’t want to give too much away, but I will say that the end was very heartwarming. At the end of each show, the CEO meets with the employees he worked with and reveals who he is. (Cloobeck succeeds in not blowing his cover despite the fact that a photo of him with an explanation of “The Meaning of Yes” is at every front desk within the entire chain.) Then he rewards each person for being so nice to him and so committed to their jobs. He even pays off one guy’s entire mortgage! That, in my opinion, puts him one step closer to his goal of being the greatest hotelier ever.

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