'Undercover Boss': Stephen Cloobeck, Diamond Resorts' 'Explosive' CEO, Outs Himself Again And Again
Stephen J. Cloobeck just can't get enough of "Undercover Boss."
Less than a year ago, the CEO of Diamond Resorts International LLC appeared on the CBS show to kick off the series' third season. During that episode, the high-energy boss distinguished himself by storming off the set, saying the failure of the staff to carry out his policies was "insanity."
On Friday's episode, Cloobeck appeared on the show again -- the first time that any boss had made a return appearance. And Cloobeck -- described by the show's narrator as "the most explosive boss" in the history of the series -- made it clear that his high-octane approach was still his lodestar. As in his first run, Cloobeck couldn't stop from outing himself as the boss -- twice, in fact, after being disappointed by his workers' performance. He also showed extraordinary generosity at the end of the show.
Veronica also told Cloobeck how she and her husband have to work two jobs as they try to save money for their daughter's surgery. Daniela, who was born prematurely, has two hernias. At the end of the show, when Cloobeck's identity already had been revealed (more on that in a moment), he showed some Oprah-size generosity: He told Veronica that he'd pick up the tab for Daniela's surgery.
And buy her a new car.
And a house. (Her reaction is in the video above.)
The first time Cloobeck outed himself in this episode, though, he did so calmly. It took place during the regular taping of the show, well ahead of the reveal. He was working with RK, who works in housekeeping at Cedar Breaks Lodge in Brian Head, Utah, one of the 220 Diamond properties in 28 countries that service 600,000 guests a year.
Immediately upon arriving on the site, Cloobeck was unhappy with what he saw at Cedar Breaks. The resort's landscaping was unkempt and rooms had mold.
It also became clear that Cedar Breaks' managers weren't on top of the situation. RK, a member of the housekeeping staff, told Cloobeck that he alerted the management of on-site problems, but nothing had come of it. And RK said that he'd yet to receive a properly spelled nametag, two years into his job. (The one he wore said "RJ.")
After hearing how RK was also raising a daughter on his own after his wife cheated on him, Cloobeck revealed himself. Very calmly, he then informed RK that he would provide him $25,000 for daycare, and a trust fund for his daughter's schooling that will grow to $50,000.
He was less cool while manning the front desk at Cabo Azul. Working with Stephanie, Cloobeck encountered a series of snafus. He found out that the workers at the front desk take down credit card numbers for reservation authorization, even though, according to Cloobeck, that's a violation of both privacy laws and his company's rules.
Cloobeck initially was curt, however, with Stephanie and the other workers handling the issues at the front desk. "That's a problem for me," was Cloobeck's stern reaction to the shortcomings at Cabo Azul. Very shortly thereafter, though, he assured those employees that he knew it wasn't their fault, that they are just trying to do their job. Speaking to the camera, Cloobeck said that he learned "you can't just throw money at a new resort" and expect results.
Cloobeck showed his more playful side while visiting with Monique, an activities coordinator at one of his resorts in Palm Springs. Before arriving, he'd told the show's TV audience that he hoped his activities coordinator was "bubbly" because the job description is "making sure everyone has a good time."
He was pleased with the way Monique quickly pushed him to lead a dance lesson for guests. It turned out be a rare moment of shyness for Cloobeck. (After dancing, Cloobeck said that he'd felt like a "moron," given his struggles keeping up with the moves that he was supposed to be teaching.) Monique also demonstrated her authority on style and design in giving Cloobeck unvarnished feedback -- telling him that the location's uniforms are dull. And she showed that she had no problem in keeping all the kids in her class in control while handing out ice cream after the dancing session.
And he went even further. He announced to a meeting of his entire staff that he plans to start a crisis fund for them. He will put in $1 million of his own money, and the company with match it.
It was a departure from the usual storyline of the series, in that the only workers who normally have benefited from the boss's generosity were those who actually appeared on the show.
But the question remains: Just how will Cloobeck top himself during his third appearance?
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Dan Fastenberg was most recently a reporter with TIME Magazine. Previously, he was a writer for the Thomson Reuters news service's Latin America desk. He was also a reporter and associate editor for the Buenos Aires Herald while living in South America.
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