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

He has been busy this winter season. His close friend Desirée Rogers rejoined the regular Saturday luncheon he had been sharing with Linda Johnson Rice. This standing date dropped to Zucker and Rice when half of the original four-person group left for Washington: Rogers to be the social secretary for the Obama White House and Valerie Jarrett to become a senior adviser to the president. But now that Rogers is back in Chicago, working as CEO for Johnson Publishing, the lunch, which Zucker describes as “just a freewheeling, talk-about-whatever-is-on-your-mind time,” is back on.

Not that he ever lost touch with the two women. During Rogers’s tenure in the White House, Zucker and Marko Iglendza, a friend who heads an airport spa company based in Charlotte, North Carolina, hosted an intimate Washington birthday party for her at Wolfgang Puck’s restaurant The Source. Michelle Obama attended. Zucker has been to several events at the White House, and he has been able to see Jarrett in Chicago, as her schedule allows. Once this past fall, she and her security entourage came to his office for a visit. And on December 29th, he and Jarrett dined privately at Chicago Cut Steakhouse, one of Zucker’s new favorite restaurants. Two days later, he toasted in the new year at Gibsons with a small circle, which included Rogers, Iglendza, the real-estate developer Jerry Lasky and his wife, Whitney (a former soap opera actress), the interior designer Julie Latsko, and the Sun-Times entertainment columnist Bill Zwecker.

Then there are Zucker’s frequent lunches and dinners at RL, the swank Ralph Lauren restaurant on Chicago Avenue, where his regular table is number 42 and the staff is happy to serve him broiled perch over a bed of chopped Brussels sprouts, even though the dish isn’t on the menu. (Last year, Zucker returned the favor by doing a citizen’s review of RL on WTTW’s show Check, Please!) He also arranged a dinner in honor of Ikram and Josh Goldman—she owns the fashion boutique that bears her name, he is an attorney and contemporary art collector—which was a thank-you to Ikram for cooking a special meal in her home to entertain some of Zucker’s friends. And there were organized movie nights with friends, shopping for the luxe look he favors (his idea of dressing down is wearing a sports coat—from Ermenegildo Zegna or Ralph Lauren and tailored on Oak Street—and a tie, Hermès being his favorite brand), Bulls games, plays, charity events, and board meetings.

He is a trustee for the Museum of Science and Industry and the Goodman Theatre and a board member for After School Matters, the educational program founded by Maggie Daley. “If I make a commitment to an organization, I have to follow through,” he says. As part of a committee that has pledged to raise $1 million for the museum in the next five years, Zucker recently hit his Filofax, sending a letter to friends asking them to remember the fun they had visiting the museum as children and offering to personally show them around the current exhibits. It’s how he operates. “In business or in philanthropy, you have to pick up the phone and ask. The worst that can happen is someone says no, but he or she won’t say anything if you don’t ask. I am a risk-averse person, but I’m not afraid to ask for something.”

And there was extensive planning for his birthday party. For the last decade, Zucker has tossed spectacular birthday parties for himself every February: Cocktails and dinner are served, music is played, and the mayor and 300 other friends come to celebrate. One year the party was held in the John Hancock Observatory; another time it was at the Casino Club. As this story was being reported, Zucker was organizing this year’s party, to be held at Macy’s Walnut Room, sending out the invitations in little boxes of Frango mints. The event was to be followed by a weekend trip to Palm Springs and an intimate dinner for 50 close friends at Rice’s house there. “Neal is the perfect person to travel with,” says Rice. Four years ago, she, her daughter Alexa, and Zucker took an extended trip to Hong Kong and Tokyo. “Before the wheels of the plane ever leave the ground, Neal knows the best breakfast place, the most fun excursion we can take, and the perfect place for cocktails.”

He lives by two mantras: “Trust but verify” and what he calls the seven Ps (“Prior proper planning prevents piss-poor performance”). They are his touchstones in every aspect of life. “I apply them constantly,” he says, and then pauses. “I mean, all the time.”

“He does everything right,” says Ikram Goldman, who is known for her own very high standards. “I’ve never known anyone who is so”—here she snaps her fingers with the words—“precise, timely, perfect, right.”

“I don’t know another person who has so many friends from so many different walks of life,” says Robin Berger, president of NNP Residential, which handles high-end apartment rentals. “And everyone is on the same level playing field.”

The most popular words used to describe Zucker by those who know him are “loyal” and “discreet.” Often he is called “the best listener.” He also has an engaging way of talking, ending his sentences with the questions “right?” or “don’t you think?”—thus throwing the conversational ball back to someone else. “I can’t think of anyone in town who is better connected who isn’t an elected politician,” says Bill Zwecker.

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Zucker can’t explain exactly how he met so many people. He just knows them, and it seems like his life has always included them. Sometimes that is truly the case. He and Linda Johnson Rice spent their early years living in the same Gold Coast building; he and J. B. Pritzker have been friends since seventh grade.

He was born to Michele Young Scher and her husband Monty, who owns a large auto dealership on South Michigan Avenue. But the two divorced when Neal was very young, and his mother eventually married Steve Zucker, the sports management juggernaut. Neal’s last name was changed, and “Steve became my day-to-day father, the one I call Dad,” he says. “But I have a good relationship with Monty, too.” The oldest of four—brother Herbie works in sports management and sisters Jennifer Healy and Tory Boyer are both attorneys living on the North Shore—Zucker started at the Latin School of Chicago. When he was in third grade, the family moved to Winnetka, and he began attending school there. He dates many friendships back to his school days at both places. He attended New Trier High, where he was an active social planner, and then the University of Michigan, where he studied business and economics.

 After graduation, Zucker returned to Chicago and became a bond broker for Exchange National Bank. He picked up his MBA from Northwestern University’s Kellogg School of Management and meantime embarked on charitable projects, including building a junior board for his mother’s cause, juvenile diabetes. “I had very smart, solid parents who emphasized education and giving back to society,” he says. His first big philanthropic splash came in 1988 when he helped create the Green Tie Ball for Gateway Green, a nonprofit dedicated to greening and beautifying Chicago’s expressways and neighborhoods. “Mary Cameron Frey [social columnist for the Sun-Times] came to me and asked me to help her friend Don DePorter [former vice president for Hyatt Hotels and Resorts], who had started this new organization,” recalls Zucker. “Don was looking to bring in a younger crowd, so I signed on to help organize what became the first Green Tie Ball.” Zucker worked hard on that event, calling everyone he could think of. “I would say: ‘How are you? How was college? Listen, there is going to be this great event . . .’” The first Green Tie Ball brought 500 young adults to the cause and established the party’s long-standing reputation as a hip affair. It also helped establish Zucker’s reputation as a savvy and well-connected young guy in the city, the kind of person who could bring out a new well-heeled generation for charity.

Zucker’s green profile dovetailed nicely with the eco-conscious agenda of the newly elected Richard M. Daley, providing more civic cred to Zucker. Over the years, the Green Tie Ball grew to draw, at its peak, 3,500 guests. BizBash, an event-industry trade publication, once ranked it as the number one charity gala in Chicago, based on its youthful profile and massive mix of entertainment and food. Zucker joined the Gateway Green board, and he chaired the tenth-anniversary Green Tie Ball, although after that he moved on to other missions, other boards. “It was just time to rotate off after a decade of working on that cause,” he says. (In the past several years, Gateway Green has seen its Charity Navigator rating drop from five stars to one star, and in 2010 the Green Tie was canceled.)

At the same time, he was on the prowl for an enterprise he could call his own. One day in the nineties, Zucker looked out of his high-rise apartment and thought, Wouldn’t this be much nicer if the windows were cleaned regularly? “From then on, everywhere I looked, I saw windows. I mean, every place has windows: hotels, hospitals, condo buildings.” With research, Zucker discovered that the window-washing business was complicated: It was dangerous; it needed a constant inflow of money for newer, safer equipment; and there was a workers’ union to deal with. Nonetheless, he approached his friend Elizabeth Alkon, whom he had first met in college, about starting the business. With backing from Alkon’s boyfriend at the time, the Lakeshore Entertainment producer Tom Rosenberg, Zucker and Alkon created Corporate Cleaning Services in 1994. Rosenberg owned several condo buildings, so the two partners started with a small but ready-made customer base. They both had connections and organizational minds, and, slowly, they built a business. In 2004, when Alkon and Rosenberg—by then married—moved to Beverly Hills, Zucker bought out Alkon’s share. (The two remain friends.)

Since then, Zucker has concentrated on promoting the latest safety techniques for his crews while achieving a clockwork precision in the management of the business. “Basically, it’s a service business, and he gives very, very good service,” says one real-estate insider. If you want a dead bird off your 36th-floor windowsill or remedial caulking around your 15th-level window frame, Corporate Cleaning will do it. They put methanol in the water so they can clean windows even in winter; they are also the only Chicago window-cleaning company certified by the state for spider abatement. “You don’t want to hear the stories I know about monster spiders around some of these buildings,” Zucker says. His company once washed all 54 stories at Harbor Point Tower in one day, so residents could enjoy clear views of the Fourth of July fireworks.

He has turned down offers to expand the business into other areas. “I’d rather stick with what we know,” he says. Still, he has these thoughts running through his head: How can we grow? What can I do better? and—the big one—What’s the right thing to do? The questions race through his mind so frequently that they form a rhythm to his days and nights until, like yoga poses, they sync up with his breathing.

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“Neal has created a great life for himself,” says one friend. “But is he enjoying the moment?”

He seems to be. Certainly, at times, there can be a fast-forward quality to his enthusiasm. “This is fun, isn’t it?” he will say. “When are we going to get together again? And what should we do?” But his spillover excitement is similar to that of a boisterous puppy: harmless and endearing. “I am excited because there are so many wonderful things going on,” he says. And if he can contribute to that, add a little spark to the world, get some people together—why not? Even when he’s home, in his apartment a short walking distance from work, he’s restlessly energetic. He Tivos everything and then watches the shows late at night. He reads newspapers and magazines (because he eats out all the time, restaurant reviews are of particular interest), handles e-mails on his BlackBerry, and keeps his color-coordinated closet up to snuff. (Years ago, a friend mismatched his shoes and disorganized his ties as a joke; Zucker stayed up for hours putting everything back in its rightful place.) Then he gets up early and starts a new day, handling the business, staying in touch with friends, planning his social outings. “Friendship takes a lot of work; there is a constant nurturing that has to be done,” he says. “But there are a lot of rewards. I think people appreciate one’s efforts. I really do.”