Diamond Resorts' Stephen Cloobeck

By Danny King
Stephen CloobeckDiamond Resorts International CEO Stephen Cloobeck runs a vacation timeshare company that has more than 220 resorts in almost 30 countries and 490,000 members. But Cloobeck has recently become better known as one of the "bosses" in the CBS reality series "Undercover Boss." He appeared on the show last January and became the first "boss" to reappear on the show on Nov. 30. He spoke with hotels editor Danny King.

Q: Why did you agree to appear on "Undercover Boss" the first time?

A:
They approached me, and I said no because I was worried about my brand. But my president, David Palmer, said, "You have to do this." It was the greatest journey I ever took. I've become a better CEO, and we're much more in touch with our team and our guests.

I realized that the most important thing I needed to do was not be behind my desk. I needed to be at my resorts all the time. And there's the "'Undercover' effect."

Q: I'm assuming you're referring to a bump in business from the exposure. How much did the show help business?

A:
I can't comment on that, but it was demonstrative.

Q: You donned a wig and various uniforms to go undercover, but you blew your own cover with one of your employees. How did you keep your cover for the second show?

A
: It's 100% unscripted. And when you see the second show, you're going to see some pretty unique things. We did something called "undercover guest," where I had cameras in my eyeglasses.

Q: Any concern that there'd be backlash in the form of employees fearing a "Big Brother" sort of effect?

A:
No. Everyone knows I'm always at the resorts. I'm always in the team dining room having lunch with busboys and valet parking workers. I own the company, and I'm in charge.

Q: Diamond Resorts recently acquired Aegean Blue Holdings and its five resorts in the Greek Isles. Any concerns about the state of the Greek economy and the European debt situation?

A:
My philosophy is that the Acropolis is still standing after 2,500 years, the sun still shines and the food's still fantastic, so I'm bullish on Greece. I would buy more properties there.

Q: How does your company cater to travel agents?

A:
We have a very robust FIT department. We run a robust business. We get tremendous viewership through our website, and we are at all of the travel shows.

I bought Sunterra when it was a crazy, busted, polluted brand with no service, so it's taken me time to rebrand it. But we're now aggressively going out to the travel agency market.

Q: How'd you go from getting a degree in psychobiology to running a hospitality company?

A:
I studied psychobiology with the idea of becoming a thoracic surgeon, but when I was a kid, I was a busboy, dishwasher, assistant cook, and I loved it. I eventually went into real estate. I built my first hotel at 29: the Polo Towers in the early '90s. It was on time and on budget.

Q: You were chairman of the tourism partnership Brand USA upon its launch. What are your thoughts on that effort?

A:
It was tremendously overdue, and it's a no-brainer. The tourism sector is the greatest export the United States has. It's larger than agriculture and larger than the automotive industry. And it requires no capital expenditures. The Grand Canyon's already built.

Follow Danny King on Twitter @dktravelweekly. 
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