Boston Chauffeur Driven Show
Tuesday, December 10, 2019

BY MADELEINE MACCAR

Windy City Limousine President George Jacobs with two of his minibuses with Chicago's sklyine in the background. Photography by Chris Weiss. George Jacobs is a firm believer in second chances. After all, his life has been peppered with them, and he even credits one in particular—stumbling upon the livery industry—with giving his life purpose.

Though his nearly decade-old Windy City Limousine is a staple in the Chicago-area transportation scene and beyond, Jacobs “just fell in love with the industry” almost as soon as he discovered it more than 35 years ago. A self-confessed action junkie, he admits that the constant activity of chauffeured ground transportation is a healthy, constructive way to quell that insatiable need to keep moving.

In 1979, five years after he put a tenacious gambling addiction behind him and joined Gambler’s Anonymous, Jacobs was selling forklift trucks to the Midwestern department store Goldblatt’s when a fortuitous encounter with the company’s purchasing agent had Jacobs himself buying the store’s 1978 Cadillac limousine.

“It was the craziest thing,” Jacobs recalls. “He was just screaming at somebody on the phone about the trade-in value that he was getting for the company limousine, and he was so mad when he hung up phone. Then he looked at me and he said, ‘George, you’re crazy: How about buying our company limousine?’ Those were his exact words.”

The two ultimately split the cost of the vehicle —$5,500—and called the nearby American Limousine to put their new acquisition in the established company’s fleet.

In another five years, Jacobs was an employee at American and poised to buy half of the company but his partner—the same purchasing agent from Goldblatt’s—backed out three days before the deal was set to close. After some scrambling, Jacobs bought the business, which “just took off like a rocket”—making it a very attractive asset to Carey International when he sold it to them in 1998 for a record sum.

“In 1984, when I bought American, we were at $2 million; when I sold it 14 years later, we were doing $20 million—to this day, it’s the biggest deal that has ever transpired in the limousine industry,” Jacobs says.

The Windy City management team (L to R): Vice President Kathy Kahne, Operations Manager Dave Lahr, Office Manager Jennifer Sypien, Controller Craig Gardner, Chauffeur Manager Jeff Arnold, Dispatch Manager Brian Heneghan, Reservations Manager Allison Kubiak, Director of Groups and Special Events Jerold Bean, Fleet Manager Piotr Rog, Human Resources Director Mary Heraty, and Lead Chauffeur Bill Moses Jacobs stayed with the company for another seven years before finally retiring. But what began as a final act was destined to be merely an intermission, thanks to the encouraging combination of industry cohorts clamoring for his return, the reappearance of an investor who had once vied with Jacobs to buy American now offering to help him fund a new venture, and a wife who was gently nudging her pent-up husband toward focusing his energy on something outside their home.

“So I’ve got my wife telling me to get out of the house, somebody throwing money at me, and former coworkers saying that they missed me and that they really wanted to do something special together—so we did,” says Jacobs.

And so, in the early months of 2006, Jacobs shook off six months of retirement to start Windy City Limousine with the coworkers who have been by his side for years—and with nary a car, chauffeur, customer, or “even an office or a pad of paper” to their name. But those behind the nascent company were determined to succeed despite a seemingly disadvantageous starting point.

“I knew we could do this: It’s something that all of us were really good at,” says Jacobs. “Without taking business from anyone else, we just went out and started finding customers. Once we opened our doors, a lot of people from around the country came to me and said, ‘Hey, I understand you’re back: Do you want to handle our work in Chicago?’ And I was thrilled to death to do it! It gave us a good place to start.”

That affiliate work bolstering the early days of Windy City began with Neil Goodman of Aventura Worldwide, which Jacobs says is “a little bit of kindness” on his and other longtime industry friends’ parts, and is a testament to the industry’s best nature and the relationships that Jacobs nurtured over the course of his career.

“It’s like a lot of people said, ‘Hey, George is back, let’s help him out,’” he says. “I think people in this industry have always valued good operators and people they can trust on a personal level. They know that’s what I am.”

For all the good things that have remained a constant in the industry, Jacobs is pleased with the positive changes he has not only witnessed but also helped bring about in more than three decades as an operator, many of which he observed during nearly 20 years as a board member for the National Limousine Association, as well as its president from 1990-1992 and again in 1994. Chief among those was helping the industry boost its image as a professional one.

“It’s gotten much more professional, and I worked really hard to get people into suits,” he says. “You can’t be accepted as legitimate if you don’t look the part. So we got people to look like professionals, which was a very important thing.”

Once we opened our doors, a lot of people from around the country came to me and said, ‘Hey, I understand you’re back: Do you want to handle our work in Chicago?’” – George Jacobs, president of Windy City Limousine

Jacobs has infused Windy City with that same heightened regard for professionalism, with much success and with many thanks to a hard-working staff. As the company does about 20 percent retail work and 80 percent corporate, it’s important to maintain a world-class image to ensure that “we continue to be all things for all clients,” even beyond the well-traveled businessmen and women, corporate outings, and destination management companies Windy City typically serves most often.

Windy City Vice President Kathy Kahne with Chicago’s Navy Pier behind her A varied fleet is a crucial component in meeting any customer’s need, and Windy City has found an effective balance with roughly 100 buses and 150 cars comprising “everything you can imagine”: sedans, SUVs, limousines, hybrids, minibuses, executive vans (the industry’s first Ford Transit, courtesy of Battisti Customs in nearby Indiana, has found its home with Windy City), motorcoaches, ADA vehicles, and party buses that can accommodate anywhere from 14 to 56 passengers are all represented in the Chicago-based company’s stable of vehicles. Jacobs says that while he has far more sedans than SUVs in his fleet, it’s the latter vehicle that is constantly in demand.

Windy City’s buses certainly hit the road in droves, too, as the company is the official transportation provider for Chicago’s many sports teams. The White Sox, Bears, Cubs, and Bulls all rely on Windy City to get them to and from games both home and away—and Lord Stanley’s Cup is a frequent VIP traveler, too. The impassioned sports fans who call the area home also account for a considerable percentage of Windy City’s business, often relying on its in-demand Transit to get them to any number of games.

But Chicago derives its unique flavor from far more than professional sports teams and their fans. A downtown rich in cultural mainstays—natural history, scientific, and art museums, the museum campus, instantly recognizable architecture, and, of course, the ballparks—is a must-see for anyone stopping by the city that’s home to the busiest airport in the world, O’Hare International. Windy City chauffeurs’ daily routes also include niche tours that bring tourists face to face with the city’s most notable structures, the abandoned and haunted buildings on Weird Chicago’s circuit, or by working with Chicago Crime Scene Tours to revisit the city’s past as a hotbed for criminal activity during Al Capone’s reign—complete with crime-scene tape wrapped around the touring vehicle.

The city, like Jacobs, was given its own second chance, albeit following the Great Chicago Fire of 1871. The two-day disaster left more than three miles of devastation in its wake and tore through the predominately wooden structures dotting the urban landscape; however, from the ashes rose one of American history’s largest rebuilding efforts, resulting in the densely iconic skyline of modern architectural feats by which Chicago is immediately identifiable.

Jacobs wears his iconic M&M’S jacket at U.S. Cellular Field, home of the White Sox with Windy City’s vehicles and logo in the background Blending an internationally vivid composite of both visitors and city-dwellers (Chicago claims the fifth-largest foreign-born population in the United States) has led to a vibrant tapestry of global representation within a comparatively condensed 234 miles. This commingling of cultures demands deft tongues, which is why Windy City Limousine keeps multilingual tour guides on retainer who can converse in at least a dozen languages—and employs chauffeurs who are fluent in everything from German and Spanish to Japanese and Hebrew.

The company’s international flair doesn’t end there, though, as its affiliate network keeps Windy City’s clients on the move in the likes of such far-flung locales as India, China, Hong King, Mozambique, India, and “virtually every country in Europe.”

More locally, Windy City has recently moved to what Jacobs calls its “final home” all contained under one roof, a sprawling campus that offers 15,000 square feet of office space (which can be expanded to a whopping 40,000 square feet), a 35,000-square-foot shop that can also spread beyond its current boundaries, and more than two acres of parking.

This move has been in the works for three years and is the result of finally finding an office that perfectly blends sufficient space with a convenient location. Boasting the third-highest population in the country, Chicago’s 2.7 million residents make it the most populous city in the Midwest—and present a certain logistical challenge to an industry that knows arriving on time is never good enough.

“We’re only about eight miles from our old facility but in time, it’s forever: Instead of being behind the bottleneck on the highway, now we’re in front of it so that during rush hour, we’re probably about half an hour closer to everything,” Jacobs says. “Plus, we’re at the intersection of three major highways: We’re exactly at the junction of everything. About 75 percent of our bus trips either start or end downtown, so the chauffeurs have a much easier way to get there—it was really important to us to take care of the chauffeurs here.”

Indeed, looking after Windy City’s 450-person staff is of utmost concern to Jacobs, and he takes pride in the team he has diligently surrounded himself with, many of whom have been with him since his days at American—and of Windy City’s original six-person staff, one has since retired but three are still with the company. His own struggles before stumbling upon the ground transportation industry left Jacobs determined to position his business as a way of helping others; that respect for his employees is why he believes so many have stayed with him over the years.

“I wanted to employ people who needed a second chance, and I did that: I employed lots of people from Gambler’s Anonymous, for instance, to give them that opportunity,” he says. “Giving people stability, a place they’re proud of, a place to work—that’s important to me. There are some people who work for me today who have been with me for 25 years. I’ve employed thousands and thousands over the years: I would guess there have been 40 to 50 marriages that have taken place between people who’ve met by working with us.”

Director of Affiliate Relations Tricia Wilcoxen And it is the opportunity to help people by giving them a steady, respectable job that is the most rewarding aspect of owning a company for Jacobs.

“It sounds corny, but seeing them put their kids through college, be able to retire, and have better lives—that’s what it’s all about,” he says.

In addition to treating Windy City’s employees with “respect and dignity,” Jacobs wants his office staff to feel empowered to make decisions on the fly and has cultivated an office staff of quick thinkers who can anticipate and creatively resolve issues before they become full-blown problems.

“If they have to make a decision, they have to feel that it’s okay for them to make that decision,” he says. “I want them to be able to make customers happy right at that time rather than waiting for later. The people here are super smart, they understand the business, and they make it work. So I trust them.”

As Chicago’s roads include underground passageways, deceptive shortcuts that a seasoned driver knows to avoid, and hotels with different entrances for different purposes—to say nothing of the inherent difficulty in maneuvering a bus through tricky tight, densely populated areas—Jacobs is well aware that driving experience doesn’t always translate into an ability to navigate the city’s unique landscape. All of Windy City’s chauffeurs receive four or five days of classroom training before they take to the road for a hands-on education in Chicago driving. And Jacobs emphatically hires chauffeurs—not just drivers.

While he says that it’s hard to call out the individuals who comprise a staff of high-performers, Jacobs identifies a number of Windy City’s team members as particularly stand-out employees: Vice President and founding partner Kathy Kahne, an 18-year industry veteran Jacobs says is “extremely knowledgeable and indispensable to us”; Operations Manager and founding member Dave Lahr, who has spent 18 of his 23 years in the industry with Jacobs; Director of Groups and Special Events Jerold Bean; Director of Affiliate Relations Tricia Wilcoxen; Reservations Manager Allison Kubiak; Human Resources Mary Heraty; Office Manager Jennifer Sypien; Chauffeur Managers Jamie Smith and Jeff Arnold; Dispatch Manager Brian Heneghan; IT Manager and Windy City’s first employee Ryan Kaczmarski; Chief Financial Officer Craig Gardner; Director of Business Affairs Anuj Patel; Accounting Manager Lisa Wilinski; Sales Manager Sarah Gomez; Greeter Manager Tom Durr; and Fleet and Shop Manager Piotr Rog.

Jacobs wholeheartedly believes that it takes a certain kind of personality to succeed in this industry, and that a willingness to work long hours and make personal sacrifices are second only to the innate drive to be the best that he feels any entrepreneur needs. But there’s a fine line between following the fire in your belly and burning yourself out, and personal pursuits are a surefire way to ward off that latter danger.

With his gambling days safely in the past, Jacobs has become a first-rate bridge player. He has 15 national championships to his name, has come in second and third at various tournaments, and played in 2007’s world championship in Shanghai, China. Like the industry he loves, bridge championships have kept him on the go and in the middle of where the action is. He also is actively involved with both the United States Bridge Federation and Gambler’s Anonymous Worldwide, having served as president of both organizations.

Nightly display of Windy City’s banner at U.S. Cellular Field, where it remains for half an inning In the late ’90s, Jacobs met his future wife, Stacy, who he says doesn’t physically spend much time with his business—“if she comes to the office once a year, that’s a lot”—but has contributed significantly to Windy City in her own way.

“She has some really good ideas and is a great ear,” Jacobs says. “She talks to me about theories all the time: There are a lot of things I’ve done over the years because she’s suggested them. She’s really smart and has gotten to understand this business. She rarely comes around but she knows that this is what I love to do and she is very, very super supportive.”

Their two children are Joanna, who’s 18 and a college student currently attending culinary school, and Kate, 14, a freshman in high school. Despite his busy schedule, Jacobs makes it a point to be home if either of his daughters have something important going on. And while his oldest daughter has helped out at Windy City by working with its human resources director, it’s his youngest who has already expressed interest in following her father’s footsteps—though Jacobs says that she shouldn’t be expecting an ounce of preferential treatment.

“When she was 8, Kate said to me, ‘Daddy, you can never sell the company until I’m 14 so I can take it over,’” he says with a laugh. “She hasn’t spent time working here yet but she will, I’m sure, at some point. She would be very interested in doing things here, but I’d have her start off by getting her hands dirty.”

In the meantime, Jacobs considers himself lucky to be immersed in an industry he loves—and loves giving back to it by offering his advice to anyone who asks. He remains active in the NLA and has recently gotten re-involved with the Illinois Limousine Association, which he helped start, because he so fervently believes in the benefit of power in numbers, especially as the fight against TNCs calls for industry unity.

“Associations are mandatory,” Jacobs says. “If everybody had to fight every problem on their own, they’d go broke. But associations accumulate data and resources and information and knowledge—and they fight things together. They work really hard to make things better for everybody, not just one person.”

Jacobs, too, works to improve the industry as a whole, and will freely use his decades’ worth of learning experiences to help anyone from an industry newcomer to an established operator in the midst of a difficult period. (He recently served as a mentor at the Chauffeur Driven Show.) The most important tidbit he can offer, though, is to be ready for anything, position your company to be capitalized advantageously, and prepare to work harder than you ever have.

“Be ready to make some sacrifices and put in that effort—but be smart because you can’t just go into it blindly and hope,” Jacobs says. “There’s no golden goose: You just have to work hard and realize that luck is a byproduct of that hard work.” [CD1115]