Living out loud

She’s tough but transparent – a hard-driving executive and sensitive soul. Christy Webber opens up so others can learn.

Christy Webber started mowing lawns to help pay for college at the University of Denver. In the photo at top, she spends some time at the White House with her life partner, Jennifer Rule.

If you’re looking for a sweet fairy tale about a landscape company’s birth and coming of age, don’t call Christy Webber. She’s got a grittier story to tell – one that grabs you like a smutty tabloid, teaches you hard-knocks lessons and encourages you to push yourself to the limit – and then push harder.

“I don’t talk about these great things like flowers or winning designs,” says Webber, founder and CEO of one of Chicago’s largest firms, Christy Webber Landscapes. “I talk about my life. And once people meet me, they are either really disappointed … or I come off as who I am, and that’s someone who can encourage others to think, ‘If she can do it, I can do it.’”

Webber lets it all hang out. “Christy models that permissive professionalism that has a stronger punch than trying to behave all the time,” says Angelia Woodside Beckstrom, national board president for the National Association of Professional Women in Landscape. “There’s some point when you just have to say, ‘Dump it – dump it all and just be yourself. Be authentic.’ Christy does that.”

Webber will tell you about being lesbian, a mother of toddlers, a recovering addict, a struggling startup, a hungry entrepreneur in acquisition mode, a good leader, a tough manager, a business junkie, a partner supporting a young family, a hard worker who needs more sleep. In short, someone who “wants to be better, just like the rest of us.”

Webber is a mentor who wishes more landscapers would study business – a hospitable nurturer who invites industry peers to see what she has built and shows them how they can have the same rewards.

“She’s transparent and warm, and the demeanor that she has is just so rare,” Beckstrom says. “I really believe that’s because she’s a gal, and she’s running her business with feeling.”

Webber started mowing lawns to help pay for college at the University of Denver, a “fancy school … even though I wasn’t fancy at all,” she says. A country girl from Montrose, Mich., Webber grew up in a working class family. Her father owned a local tavern. Her uncles worked on the General Motors assembly line. She went to church, played sports and took a basketball scholarship after high school. She earned a college degree in physical education.

Sounds pretty neat and clean, but as Webber tells it, “the eighties got a hold of me … cocaine” and she was in and out of recovery. She returned to Chicago after the death of her father in 1983 and worked odd jobs.

“I was cleaning houses and the gal asked me to cut the grass,” Webber says. “I said to her, ‘If you have a mower, I’ll do it.’ As a country girl, I knew how to cut the grass and fix the mower.”

So Webber started mowing grass, then launched a business from her kitchen table that grew to about $7 million by the late 1990s when her partner left the firm and “the business really jumped off the page.” They split the company in 1999 and it went from $2.2 to $4.2 million in one year.

Today, Webber’s client portfolio includes heavy hitters like Millennium Park, Grant Park, Soldier Field, the United Center, Trump Tower, and all of the police and fire stations and libraries in Chicago. More than 250 people work for her company, and she has acquired some of the Midwest’s most prominent firms.

Webber started her company at a kitchen table. The business, at one point, grew to $7 million in revenue.

Webber attributes her success to a lot of sweat and a team she trusts. She hired her best friend, Robert Post, to be CFO – he was running his own landscape/snow business before joining Webber in 2002. “I trusted him and gave him the keys to the house and he took control,” she says.

Webber has acquired four companies since 2006, adding on a materials business, growing homeowners association work, building the snow business, adding construction and continuing to bid on high-profile municipal contracts.

During all of this, she built a tight-knit team of people she trusts. People like her, and people who are different than the demographic norm for landscape executives. “I have more women and blacks and Hispanics in upper management, which is a blast – it’s easier to work with those you like. I have six lesbians who work for me. To have that percentage of dykes is rare,” she says.

That’s the type of unpolished candor that wins the hearts of Webber’s staff, clients and industry peers. She is perfectly comfortable marketing why she’s not your typical landscape professional.

“I have taken advantage of everything,” she says. “My status as a minority, my sexual preference – if I was female, I was going to get what I could get out of that. Being a lesbian who lived in the city and rode a Harley was appealing to customers. They thought it was cute, or cool, something to talk about at cocktail parties.”

Webber’s organization has been recognized as such. Her firm was included on Inc. magazine’s Inner City 100 list of America’s fastest-growing urban businesses, and Webber was inducted into the University of Illinois at Chicago’s Entrepreneurship Hall of Fame. She’s successful, she says, because she listens. And she lets people help her, and she genuinely works to help others in return. Meanwhile, her life partner calls her “Christy Webber, the Golden Goose.” Webber says this is because, “If I need something, I listen and if I get quiet enough to let God help me, or whatever you believe in … if I keep my mouth shut and I don’t get in the way of it, it comes.”

“It” can be a valuable manager. Like when the woman who designed Webber’s kitchen cabinets closed her business and asked Webber for work. “She said, ‘I’m smart in business, and I’m a good manager … I could help you,’” she says. Webber brought her on board, and now that friend is her vice president of construction. Another one of Webber’s key managers came to her from Chicago’s Morton Arboretum. “No landscaping experience,” Webber says.

Actually, Webber admits she’s a good leader, but a turbulent manager. Every one of her key mangers has submitted a resignation letter at some point (though they still work for the company).

“I’ve had to practically go through therapy to work with my own staff,” she jokes. “I’ve had to learn how to be quiet and understand what I should be pushing.”


Bolder, and always better

“My whole life, I was always trying to be better,” Webber says. “Better at sports, and better at everything. I was an achiever, and I was always addicted to something – sports, church, drugs, and now it’s my business. It’s a pattern of my life. It might not be good.”

In spite of her addictions, Webber has served as a valuable business counselor to others – perfect strangers she meets at conferences, actually. “She has personally gotten involved in peoples’ lives to help them grow as professionals for no personal gain,” says Angelia Woodside Beckstrom, national board president for the National Association of Professional Women in Landscape. “That is such a model of servant leadership that transcends an award.”

Webber has entertained two sets of landscaping pros at her home, allowing them to tour her sites and meet with management. Why do this? “People helped me and believed in me … and I’m also superstitious that if I don’t help others, God won’t help me or watch out for me,” she says. “They say they learn a lot when they leave … and they also get me super nice gifts for the free housing like a huge load of deer meat they shot and had cut up by a butcher!” she says.

Really, Webber says she just wants more landscape professionals to: “Pay attention.Pay attention. Pay attention.” She’s referring to landscape business owners who overpaid themselves during the recession and ignored unprofitable jobs. She’s talking about the guys who are out of business, and the companies she has acquired (and perhaps those she has eyes on.)

“In the acquisitions I have done, they (former owners) say the same thing: I dropped the ball. I stopped doing the things Christy does. I just let the company run itself,” she says. Webber doesn’t feel threatened by people in the industry who are bigger and stronger than she. “I will listen to them,” she says. “I let people help me grow my business.” She has been known to call ValleyCrest managers to ask for their insight on matters, and she visited their headquarters to tell them about her business goals given their desire to move into the Chicago market.

And how does she balance all of this? “I don’t sleep,” she says. “I have a great life – you know, I’m driven. I think that’s the thing. I’m passionate.”


March 2013
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