More bosses go 'Undercover'
"It was unbelievably rewarding," Cloobeck recalls of undertaking tasks from working a front desk -- where his photo was displayed, making him fear his charade wouldn't last long -- to doing engineering chores. "For me to be able to go under cover at any of my hotels worldwide was a treat. And I actually got away with it.
"The show put together a great makeup package that took me about an hour every morning to get on. The first day, I have to say, was a little uncomfortable. I wasn't used to wearing a wig."
Cloobeck knew of "Undercover Boss" from some friends having done the program previously, but his experience was preordained not to be the same.
"I think the bosses are being given slightly more challenging jobs this season," says executive producer Stephen Lambert, who has additional "Undercover Boss" franchises running in locales from Britain (where the show originated) to Australia.
"The challenge for many shows is to give the feeling that it's getting better all the time, and I think we've found really strong characters in our bosses this season. And we've encouraged them to do quite dramatic things."
Indeed, without revealing what happens at the end of the first new episode, Lambert cites Cloobeck as "one of the most generous bosses we've had." For as much as he may have given, Cloobeck maintains he got a lot back, including getting insight into beneficial changes.
"It was an emotional, bizarre, cathartic experience that I wouldn't trade for anything," he says. "I created this company, these philosophies are mine, and I live them every day, and it's nice to see that all my team members really embrace them, too."