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THE ART OF THE ASK “The worst that can happen is someone says no, but he or she won’t say anything if you don’t ask,” says Zucker, in his Gold Coast office.You see the photos, too many to count. Beautifully framed photos line every horizontal surface; digital displays change faces every few minutes. This is the office of Neal Zucker, a 45-year-old businessman and philanthropist who has hundreds, if not thousands, of friends, and at first glance it seems the room might hold a picture of everyone he knows. Some of the faces are immediately recognizable: Michelle Obama, Richard and Maggie Daley, Desirée Rogers, Valerie Jarrett. And some of the pictures tell a story: a summer party at the 230-acre Wisconsin horse farm of the venture capitalists M. K. and J. B. Pritzker; a dinner at the Palm Springs winter home of Johnson Publishing’s chairwoman, Linda Johnson Rice; the British-style wedding of the Chicago printing heiress Shawn Donnelley to the English author Christopher Kelly.
“I know, there are a lot of pictures,” Zucker says in his signature slightly overcaffeinated style. “But what can I do? People keep giving me photos.” And it just wouldn’t be friendly not to display them.
The room is homey, anyway, more like a man’s study or a parlor in a traditional English country house than an office. It is a tailored and tweedy place, where tattersall wool chesterfield sofas flank the big-screen TV, the leather is burnished, and the floor-to-ceiling drapes are tied back by golden ropes with oversize tassels. No shabby, all chic. This is where Zucker works as president and CEO of Corporate Cleaning Services, Chicago’s largest all-union window-washing company.
Zucker started the business in 1994, when he opened a small first-floor office on Elm Street in the Gold Coast neighborhood. Now the company commands the whole building, including the warehouse section in back. Trucks and crews venture out from there to wash the windows of some of the finest residential and commercial properties in the city: the John Hancock Center, the Willis Tower, the Four Seasons, the United Center, Northwestern Memorial Hospital, most of the condo buildings along Lake Shore Drive—1,200 buildings in all.
He built this business himself (along with a partner for the first ten years), although he does get support from his friends. And while the photographic images are stunning, all the details—and Zucker is totally about details—can be found on his Microsoft Outlook calendar. “I refused to give up my Filofax until about a year ago,” he says, moving to a large computer monitor. “I just didn’t think I wanted to go electronic, you know what I mean? But now I can keep track of everything.” When he says “everything,” he means it. A knife-thin man overflowing with energy, he brings up a color-coded screen of weeks, with every day action packed and coordinated down to the minute. It is the hyperannotated calendar of a dashing bachelor about town who has never been married, eats 21 meals a week at restaurants, attends almost every party, remembers everyone’s birthday (and mails a card), and always picks out the perfect hostess gift.
Zucker has become a go-to guy in Chicago’s social and business worlds, a highly praised entrepreneur as well as a sought-after dinner party guest or travel companion. He is best friends with a number of prominent women in town, including two who have spent a lot of time recently at the Obama White House. In the local philanthropic world, he is a quiet leader, particularly when it comes to mobilizing the talents and the wallets of the 40-something crowd. He has fashioned a life for himself that is almost a throwback to another time, a time when everyone had polished manners, dashed off handwritten notes on real stationery, and imbued the simplest acts of bonhomie with a certain elegance.
His own story is often lost in the klieg-light glow of those around him. But the answers to who he is and why he is so popular can be discovered. It helps that there are less than six degrees between Zucker and everyone else.
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Photograph: Anna Knott