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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Monique Ivan Woodruf

Diamond Resorts has a class action lawsuit just from their activities at Point of Poipu in Hawaii. The maintenance fees have tripled, they've illegally installed DRI employees on the board and are not trying to push through a "water assessment" that is so expensive it defies logic. They have known about the water damage for years and then give owners ninety days to pay thousands of dollars or threaten them with bad credit and liens.

My timeshare week was cancelled less than two months before we are to leave for vacation, even though we've paid our maintenance fees, and now my three children won't get to have the only vacation they get with their parents together this year.

No wonder this guy can afford everything, including a bodyguard... he monetarily rapes the middle and lower classes!

June 24 2012 at 8:49 PM Report abuse rate up rate down Reply

I don't understand how anyone can still be fooled by the "Undercover Boss" trick anymore. I mean this show has been on television long enough that you think people would be wise to the deal. Okay, for the first couple episodes years ago, it might be understandable that people got fooled, but after that, how could you NOT be suspicious of the bumbling middle-aged "new guy" with the fake glasses and moustache showing up one day and it's your job to train him? Put it this way: If Sacha Baron Cohen came to your city tomorrow doing his "Borat" act and other crazy stuff, would you really fall for it, even after having seen the movie? Of course not. Now that the cat is out of the bag, he can't really do Borat anymore with people figuring it out immediately. Same thing with this Undercover Boss. How could these employees be so stupid to fall for it?

April 23 2012 at 6:41 PM Report abuse rate up rate down Reply
1 reply to whatsupjay's comment

I've actually run into the CEO of the bank I used to work for, and I had no idea who she was. I worked in a call center for a gigantic bank doing loans... never saw the person before in my life. Not everyone that works for every company is going to know what their CEO's look like. not to mention, I have had to train plenty of people whom I never had the pleasure of seeing again... mostly because the job was too much for them.

Plus... this show has been on for a few years I gather.. however I've just started watching it. I doubt everyone who has a job has bothered to watch this show.

November 30 2013 at 2:13 PM Report abuse rate up rate down Reply

they should have a under cover boss at pep boys her in bensalem pa...wholesale end of this store they are the best..john simpson is the man...customers love him.he works very hard and he has had part of his lung removed and back to work in 4 this time pep boys took alot of his time and time means are still struggling catching up with the bills .our house has falling apart and u know what..he still earns you money for no bounes...that would help us out alot...i have him..he is my hero

April 22 2012 at 9:32 PM Report abuse rate up rate down Reply

Love the show, it is real, and I really like that the CEO shows his employees the appreciation they deserve!

April 22 2012 at 1:20 PM Report abuse rate up rate down Reply

Very informative. A lot of companies look at .upfront sales, not the sustaining of these accounts long term.

January 23 2012 at 4:14 PM Report abuse rate up rate down Reply

Steven Cloobeck is just wonderful. Apparently company makes alot of money but he is more than willing to share. Kudoos to him. Wish I had boss like him!!!

January 18 2012 at 6:02 PM Report abuse rate up rate down Reply

I really don't understand this 1% war going on against the 99%. We are all humans. If it's about money. get a job and save your money. If you are 20 years old and save $5000 a year for ten years, you will have saved $50,000 after 10 years. You would have enough to start a small business by the time that you are 30. You can't do it? Well, don't! But don't crybaby about those who do.

January 16 2012 at 11:28 PM Report abuse rate up rate down Reply

One Word

January 16 2012 at 11:04 PM Report abuse rate up rate down Reply

It's about time bosses really helped employees with what they need. Not just quarter raises...LOL Good for him!

January 16 2012 at 10:52 PM Report abuse rate up rate down Reply
ed prochaska

I wouldnt go to this guys place of business just because he talked to both those women! there are better ways of talking to people than teh way he did.

January 16 2012 at 10:25 PM Report abuse rate up rate down Reply

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