Hotelier Becomes Benefactor For Medical Bills On 'Undercover Boss' Premiere

Undercover Boss Stephen Clobeck Diamond ResortsMovies, novels and television shows are often at their most poignant when they take on contemporary subjects. Over the course of the current financial crisis, few versions of commercial entertainment have been as pitch-perfect as the CBS reality series "Undercover Boss." By sending corporate executives to work incognito as common employees "Undercover Boss" succeeds in spreading the pain. With no fancy connections to rely upon, the boss is forced to get his hands dirty just like you and me.

The massively popular series returned for its third season on Sunday, January 15. ("Undercover Boss" was the most popular new series on television during its first year.) Taking center stage to kick off 2012 was the CEO of Diamond Resorts International, Stephen J. Cloobeck.

From the outset, if there's anything that's clear about Cloobeck, it's his high-energy, restless demeanor. Determined as a young man to shed the baby fat, he became so enthused about physical fitness he trained as a body builder. The Encino, California, native also decided that his initial plan to become a surgeon wouldn't provide him with enough money.

Instead, he entered the hospitality business. Early successes allowed Cloobeck in 2006 to buy the time-share company he would rename as Diamond. The original price tag of $5 million has since grown into a half billion dollar company with 205 worldwide resorts, offering 27,000 guest beds in 28 countries.

Donning a shaggy wig, the man now known as James Fisher visited four Diamond resorts to check in on his staff and lend a hand during the season premiere. His wife, the former beauty queen Chantal Leduc-Cloobeck, is initially skeptical, and says she's not sure whether Cloobeck has ever changed a light bulb in their house. Indeed, his staff is also dubious of his technical capabilities. On his first assignment, Cloobeck is sent in to work as a maintenance worker in a hotel branch in Sedona, Arizona. Helping to fix an overheating air conditioning unit, Cloobeck doesn't prove to be of much help. "Man up," his supervisor, Randy, says.

Next up is a task that falls entirely within Cloobeck's wheelhouse. Visiting the Diamond call center in Miami, Cloobeck is able to see whether his company philosophy is being put into practice. He calls it the "meaning of yes" doctrine, which dictates that hotel workers never say "no" when dealing with the customers. So when call center worker Sarah allows a slew of potential clients to hang up without offering alternatives in the face of an undesired result, Cloobeck loses it. "Insanity," he says during a confessional with the television. He also finds Sarah unable to properly use his company's computer system. He then reveals himself to Sarah, but quickly lets her know the fault lies with management. He proceeds to sit down with floor manager Tori. But before giving her a full grilling, he tells her she has to fix the problem before it spreads to other workers. Then he storms off.

An apprenticeship with a Diamond painter in Williamsburg, Virginia, exposes Cloobeck to the inefficiency of his operation. By his own account, the team is woefully understaffed and sent into battle with an insufficient toolkit. Electric sanders in the place of the paper version could cut down the work time. The use of a basic plastic goggles isn't enough in protecting the painters. But Cloobeck never reveals his ability as CEO to change the workplace conditions. Rather, he calls the painting job "boring."

His solidarity with his workers is brought into starker relief at his next visit to a front desk in Scottsdale, Arizona. A friendly conversation over lunch with Amanda quickly turns personal. It's soon revealed that the young lady, just 22 years old, uses her paychecks to help pay off her mother's medical bills for her multiple sclerosis.

But Cloobeck doesn't just take an interest in his workers' lives. During the post workday reveal, he alerts the workers back at his beach home of his plans to arrange for the purchasing of a hybrid truck and a subscription to a meat-of-the month club. These tailored gifts are supplemented by bonuses, European relocations, and, yes, the tab for certain medical bills.

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