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Former West Rogers Park Resident to Star on 'Undercover Boss'

By Benjamin Woodard | December 6, 2012 1:11pm

WEST ROGERS PARK — A Chicago native who runs an international business services company returned to his blue collar roots — after disguising himself in a long-haired wig and dyed mutton chops — to star in an episode of CBS's "Undercover Boss."

Steve Greenbaum who runs PostNet, which resembles FedEx and UPS with a small business focus, will be featured on the network's reality show at 7 p.m. Friday night.

"I thought that guy [on "Undercover Boss"] was very much who I am," said Greenbaum, who was born at the now-closed Edgewater Hospital and later graduated from Philip Rogers Elementary School.

After dropping out of Sullivan High School at 16, he moved to Las Vegas with his father and brothers to find work.

He was a ditch-digger and a plumber before he and his friend, Brian Spindel founded a mailbox rental company in Las Vegas that developed into a packing and shipping company in the 1980s. Now it boasts 700 franchised stores worldwide.

The TV show pits company bosses against their employees in a video-taped arena of an ordinary work day. The unknowing employees tend to have a few things to say about how the company is run, and the bosses tend to learn what life's like on the company's front lines.

Greenbaum, who now lives near Denver, still has a soft spot for the neighborhood and the townhome behind the High Ridge YMCA on West Jarvis Avenue, where his mother raised him.

"You could take the boy out of Rogers Park, but you can’t take Rogers Park out of the boy," he said.

He and his family still visit Chicago once a year. He runs on the lakefront and reminisces with a slice of pizza at Gulliver's on Howard Street. In 1996, he spread his brother's ashes over the grass at Rogers Park.

"He was one of the original tough guys from the area," he said.

The 51-year-old finished filming with a CBS production crew earlier this year for the episode, which features Greenbaum disguised as an ordinary worker, interacting with his franchisees.

Greenbaum couldn't give much away before the show airs, but said the experience was "powerful," and learned he needed to "do a much better job about connecting with my employees and customers."

Mike Blair, a childhood friend of Greenbaum's, said he can't wait to watch the episode.

"I already got it set up on a DVR so I can tape it and rewatch it," said Blair, who grew up a few doors away from Greenbaum, and now lives in Arlington Heights. He's quick to point out that he wouldn't have been fooled by Greenbaum's grungy getup in the show.

"I've known him my whole life and know what's behind the makeup," he said. "I’d recognize him right away."