Diamond Resorts Exposed on "Undercover Boss"

We just became aware of something very interesting for the timeshare world. Diamond Resorts, an international timeshare giant, will be the subject of the latest episode of the CBS Hit Show "Undercover Boss". Here at TimeshareJuice not only are we fans of both the show and Diamond Resorts but the topic of going undercover in a timeshare company sounds absolutely JUICY to us (yes, the pun was intended!)

We are shocked!...and happy.

At TimeshareJuice we've never shied away from the fact that "Timeshare" has a..well, "dicey" reputation (let's leave it at that). And for some companies that is a well-deserved reputation. We've openly discussed timeshare scams on our website (that guy's blog post has been viewed over 2,600 times!) But that is not the "timeshare" we know and love. Timeshare has been a wonderful and flexible way for us and millions to experience luxurious vacations by staying at their home resort, using timeshare exchange or using timeshare rentals. The market wouldn't be this big if timeshares were not awesome.

We think having Diamond Resorts as the subject of Undercover Boss is provacative for 2 reasons:

1. Diamond Resorts is like Apollo Creed. They have everything to lose and that fascinates us. If you've ever seen "Undercover Boss", you know that it is a fair and balanced depiction of the company. Yes, there's some added drama (we like the drama too - get tissues ready) but they do show the company the way it is, blemishes and all. So if Diamond Resorts has blemishes, they will air to millions. Diamond Resorts has a lot to lose. If they show Diamond Resorts operating in a shady manor or their salespeople deceiving customers, they will feel the wrath of consumers all over the world and the demise of their Brand.

2. Timeshare is taboo. There are 8 million timeshares at over 5,000 resorts in over 100 countries around the world and yet rarely do you ever hear of the mainstream press cover anything about timeshares. For the most part, it's off limits. With an average sales price of $25,000, that's a total market value of $200,000,000,000 or $200 billion! That's almost as much as the CEOs of Big Banks made last year (don't get me started). All kidding aside, that's a big number. If each owner spends $5,000 each vacation (airfare, meals, day trips etc) that's $40 billion spent each year on vacations using their timeshare. And yet when was the last time you read about timeshares in the newspaper or on your iPad? Exactly.

We applaud Undercover Boss for addressing this topic and Diamond Resorts for putting themselves out there to be exposed. Hey Stephen Cloobeck (CEO of Diamond Resorts) we give you major props (woot, woot!) for putting your feet to the fire. As for us, we'll be watching in the office, ice-cold beer and popcorn in hand, to see how hot it gets :)

What do think of Diamond Resorts being on Undercover Boss? Did Mr. Cloobeck make a bad move?
We want to hear your comments

After the show: "Diamond Resorts Falls Flat on Undercover Boss: Timeshare Needs a Hero"


We'll be watching. Going undercover on timeshares? That we have to see. And love the Apollo Creed reference.

January 12, 2012 01:04


"If they show Diamond Resorts operating in a shady manor or their salespeople deceiving customers, they will feel the wrath of consumers all over the world and the demise of their Brand" ..... i don't think it will show!

Diamond has had some problems but they do have a good reputation.
It will be interesting and the show itself is good TV. Can't wait to see it!

January 12, 2012 16:20
Texas on the Poipu

Cloobeck isn't worth doing a puff piece on. What Cloobeck and Diamond Resorts needs is an in depth investigation into his high handed, illegal and unethical treatment of timeshare owners around the globe. Britain BBC has done an investigative piece on him, St Martin Timeshare owners won a court battle against Diamond Resorts. Pretty soon, he is going to has his head handed to him on a platter regarding the Point at/of Poipu owners. Search the internet and you will find thousands of complaints against Diamond Resorts. Check out facebook and put in pointatpoipu in the search box at top middle of page. If you own a timeshare with DRI as the management company, Get rid of them. If you have points with DRI, I feel sorry for you. If they try to sell you a timeshare or points to their "The Club", run for the hills. This space is far too small to detail all of Diamonds transgressions. They are nothing but shysters.

January 12, 2012 17:14

For those of you that would like a little more info about "Undecover Boss' , here it is;

CBS's UNDERCOVER BOSS Season 3 to Premiere 1/15

What an exciting week-end, Sat the Pats and Sun the Diamond Resorts Show! ... WOW

January 12, 2012 17:20

Oh wow, timeshare undercover? I find this very interesting. What's next, an investigation of RCI for selling inventory that timeshare owners deposit for exchange? How they paid a big fine and then back to business as usual. Maybe they'll dig into the RCI Class Action Lawsuit ? Or maybe they should just read Jayster's blog post on RCI and where timeshare went off the tracks

Texas on Poipu, I'm sorry to read what you went through. I hope the show brings some attention to the matter for your sake.

January 13, 2012 00:48

I just received the following from the Diamond Resorts news email on its 1/15/2012 "Undercover Boss" appearance.

-------- Cut-n-Paste below FYI ---------------

We're opening up—turning Diamond Resorts International® inside out—to make sure we deliver the ultimate hospitality experience.

And we're doing it on national television!

Watch the season premiere of UNDERCOVER BOSS on January 15 on CBS. Our Chairman and CEO, Stephen J. Cloobeck, goes undercover on the job to discover what's good, what's great, and what can get even better.

When this journey is over, you'll know everything that goes into making your vacation lifestyle a home-away-from-home. Mr. Cloobeck goes hands-on in every aspect of Diamond. It's a fascinating, entertaining look behind the scenes... and as a result, ‘The Meaning of Yes®’ will reach an even higher standard of excellence.

Remember to watch UNDERCOVER BOSS on CBS, Sunday, January 15, at 8pm/7pm CST. Please check your local listings to make sure you don't miss it.

The Diamond Resorts Hospitality Team

January 13, 2012 05:34

Thanks for sharing that release. Any chance of Mr. Cloobeck writing a blog post here about the experience and to address questions from Diamond owners around the world? Do you have contact info for Diamond Resorts corporate office?

January 14, 2012 01:33

Obviously the show didnt better the public's perception of Timeshare resorts showing the inadequate training that the employees receive. It does show a huge difference in pay between CEO's and the men and women that actually work the day-to-day operations. I didnt see any incentives for most of the day-to-day workers who werent featured on the show.

January 16, 2012 19:40

The best I can do! Try to reach the top execs> ; )
if you believe the TV "Boss" story ..... then there IS a Santa Claus!!!

About Diamond Resorts Corporation
Diamond Resorts Corporation and its subsidiaries develop, own, operate and manage vacation ownership resorts and, through resort and partner affiliation agreements, provide owners and members with access to 71 managed resorts and 137 affiliated resorts and six cruise itineraries through THE Club® at Diamond Resorts International®. To learn more, visit DiamondResorts.com.

January 16, 2012 20:37

This appeared as a comment elsewhere but seems appropriate here too.

April 22, 2012 23:30