On ‘Undercover Boss,’ a Hotelie Gets His Hands Dirty—Literally

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The show puts CEO Andrew Simon ’92 on the front lines with his workers at Las Vegas’s Fremont Street Experience

By Beth Saulnier

It was hardly how Andrew Simon ’92 imagined spending his 51st birthday: on his hands and knees in 110-degree heat, scraping wads of used chewing gum off the floor of a busy pedestrian mall. And for Simon, who heads a famed Las Vegas tourist attraction, the day only got worse. He was also tasked with mopping up, er … puddles that some visitors, impatient for a restroom, had left on the pavement.

The toil was part of Simon’s stint on a custodial crew for an episode of the CBS series “Undercover Boss.” President and CEO of Vegas’s Fremont Street Experience, Simon went incognito on the reality TV show, which disguises corporate leaders and puts them to work on the front lines with their employees—not only offering a hands-on taste of what it takes to keep their organizations running, but giving them a peer-to-peer look at the people who hold down those jobs.

For the episode, which aired in late January (and is available for streaming on Paramount+, Hulu, and elsewhere), the show’s makeup artists transformed the normally clean-cut Hotelie into a character vaguely resembling Shaggy of “Scooby Doo” fame—dubbing him “Ken Masters” and concealing his identity under a tousled wig and a longish mustache and goatee, plus a pair of heavy-framed black eyeglasses.

“My girlfriend was there, with a friend I've known for 31 years,” Simon says of the moment when—as in all episodes of the show—his new look was unveiled. “I think I could have walked right by them on the street, and they wouldn't have known me.”

As head of the popular tourist attraction, Simon oversees what’s touted as the second-busiest street in America, after NYC’s Times Square. Drawing some 25 million visitors a year, it comprises five blocks in downtown Vegas covered by a multimedia canopy that boasts nearly 50 million LED lights and a 600,000-watt sound system.

Requiring no admission fee (except on New Year’s Eve), Fremont Street offers sound-and-light shows, live music on three stages, and proximity to a variety of casinos, bars, restaurants, and shops. Its primary source of revenue is two zipline attractions—a lower one ridden in a seated position, and a higher one where guests “fly,” Superman style—that allow visitors to soar down the street above the crowds.

In addition to Simon’s stint on the custodial crew, the program put him to work on both the canopy and the zipline. (“They didn't tell me in advance,” he notes. “I had no idea what jobs I was doing until I showed up that day.”)

For the former, he donned a safety harness and joined an overnight shift 150 feet above the pavement, gingerly picking up trash tossed into the canopy from the windows of an adjacent hotel. And yes: he’s a tad afraid of heights.

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“Frankly, nobody wants to see a CEO do the jobs perfectly—that doesn't make very good TV, and it would seem kind of obnoxious,” Simon observes with a chuckle, contemplating the program’s appeal. “And the reality is that I wasn't very good at these jobs. They didn't have to do much editing to prove that.”

Frankly, nobody wants to see a CEO do the jobs perfectly—that doesn't make very good TV.

Working on the upper zipline—the lower level was closed due to staffing shortages, an ongoing challenge for Simon’s firm and so many others—he had to schlep multiple sets of 25-pound riding “trolleys” at a time down five flights of stairs, among other duties.

As he tells the camera: “I have never done a job this taxing on your body.”

When Simon filmed “Undercover Boss” in mid-2021, he was a relatively recent hire: he’d joined Fremont Street the previous fall after more than a decade as an executive at AXS TV under chairman Mark Cuban.

“It was a great opportunity to see the operations in a way that maybe you wouldn't when you come in at a CEO level; sometimes people don't tell you the truth, or they're afraid to come to you with ideas,” he says of appearing on the show. “It gave me a chance to see what it's really like. I always knew the jobs were tough, but doing them gives you a different perspective.”

Asked if he thought that his workers had really fallen for his cover story—the show always needs to explain the presence of its cameras—that “Ken” was being filmed for a documentary about people looking for new careers, he says that his particular locale made it less of a stretch.

“We shoot so many shows on Fremont Street,” Simon says. “‘CSI: Las Vegas,’ ‘Good Morning America,’ ‘Real Housewives’—you name it, we have different show here every week. So I don't think people are as blown away that there's a TV camera following someone around.”

Top image: Simon, incognito as "Ken Masters," works with a crew cleaning Fremont Street's canopy, high above the ground. (Photo by CBS)

Published March 24, 2022

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