It Ain't Easy Being Queen

Tim Gunn is trying to keep his cool. He’s sitting on a faded loveseat in a stifling apartment on Manhattan’s Upper West Side, his white-gray hair shellacked into a helmet of efficient sophistication. Best known as Heidi Klum’s academic majordomo on Project Runway, Gunn recently graduated to his own show, Tim Gunn’s Guide to Style, which is taping in the unit next door. You could say he’s arrived, Hollywood-style—his mannered voice and "Make it work" catch phrase have earned him cavalcades of devotees—and you could assume that amid the sweaty hive of stylists, publicists, and producers, Gunn is the brightest star in this room. (It is, after all, his show.)

He is not.

That spotlight belongs to Gretchen Monahan, an elfin brunette in a green Theory dress. As Gunn’s new onscreen partner, she is the antifreeze to icy season-one cohost Veronica Webb, who paralyzed makeover candidates with her supermodel hauteur. By contrast, Monahan exudes nothing but perky accessibility. She’s come a long way to sit in hair and makeup in this prewar apartment; it wasn’t so long ago that the college dropout was standing on the other side of the chair, coiffing and coloring well-to-do ladies in her Wellesley salon, Grettacole. Yet as she’s cooed-over here, a team of image-makers brushing and blushing and powdering her face, she seems entirely at home. "I have no days off now, no breaks," she says between fake-eyelash applications. The grin she wears is the giveaway that it’s not a complaint.

Over the course of her career, Monahan has frequently reinvented herself: as hairdresser, retailer, designer, Dove spokeswoman, would-be author, talk-show extra, and celebrity stylist. Still, it’s as the Gretta behind Boston-based Gretta Enterprises, which pulls in what Monahan says is upward of $10 million a year, that she’s mostly been known. To the casual observer or salon client, Monahan has it all—a quick mind, a pretty face, a successful company. To those who know her better, there’s also the way she seems unhampered by her own flaws. "That girl could fall in a mud puddle," says Grettacole lead colorist Julie Deane, "and come out with a clean white dress on."

But as Monahan debuts alongside Gunn this month, her 13-year-old business is at a critical juncture, where the traits she’s used to fuel its rise—charm, chutzpah, superhuman determination—have become the ones that could lead to its demise. Her jet-setting lifestyle leaves scant time to supervise her salons, let alone stop in to beguile clients. Her staff is split between those loyal to a fault and those resentful of her rise. And, as always, competitors are circling, eager to fill her niche should she, as rumored, leave Boston for good. "She’s at the point where she’s trying to grow a brand," says one former employee. "But that brand was founded on her person. What will happen when she’s not around?"

It would be easy to dismiss Monahan as just another Kelly Ripa, petite and bubbly with "sidekick" practically stamped on her forehead. But unlike Ripa, who traded on her soap-star role to get ahead, Monahan overcame a Lifetime special of a childhood. She bounced among relatives’ homes (her mother, a schizophrenic, was hospitalized when Gretchen was four; her father left not long after) before finding permanent refuge at age 13 with her aunt and uncle, Kathy and Eddie Priest, a receptionist and barber, in Waltham.

Money was tight in the Priest household. While the rest of her friends at Waltham High spent their weekends cheering for the football team, Monahan was sweeping floors at bridal emporium Yolanda’s, where she was first seduced by the glamour of the fashion industry. "Even after work, I used to press my nose up against the glass for hours," she says. "For as long as I can remember, I wanted to be part of that world."

After graduation, Monahan enrolled at the Fashion Institute of Technology in Manhattan. She lasted less than a year. "I was thoroughly embarrassed and disappointed and depressed," Monahan says. "I thought I had talent." The shame of this failure seems to haunt her even now, pushing her to work longer, do more. And so she went from standing on the threshold of the glossy world of high style to selling cosmetics at the Watertown Mall. "I knew I wasn’t going to work in that mall forever," she says. "There had to be a better fucking way." (It’s always startling to hear raunchy language emanate from someone as button-cute as Monahan—but swear she does, regularly and with gusto.) Frustrated, she signed up for classes at the Nocera Group School of Hair Design. There, she learned she did have talent, albeit in another medium. The beauty industry is based on the selling of self-esteem, and Monahan discovered she had an uncanny gift for it.

By the time she founded Grettacole in Wellesley in 1995, Monahan, then just 24, had transformed herself into a hardened businesswoman. "I went to work with her and thought, This was not the same shy, cute Gretchen we used to know," says Lisa Hanson, her cousin and bookkeeper. Boss Monahan was ballsy, ribald, and demanding. She could also be generous and charming and instantly convincing. Most of all, she was magnetic. "She’ll stroke the ego of the person she’s talking to, whether it’s a flower seller or a high-powered executive," says a former employee. And while the services were good—Grettacole was one of the first local salons to split stylists into specialties—it was the Monahan charm that clients came back for. They’d line up for chair time, then put up with her chronic tardiness. (Which persists: In the course of my reporting this story, Monahan missed three interviews, was late for several others, and arrived at her cover shoot nearly an hour behind schedule—then proceeded to somehow earn the instant forgiveness of everyone on set.) She has that rare knack for laying it on thick without crossing the line into smarminess: When she heaps praise on your $30 H & M dress, you find yourself believing her.

In the 10 years after she launched Grettacole, Monahan went on to open two more Boston-area salons, the beauty shop G Spa, and two Gretta Luxe fashion boutiques, where she sold $3,000 handbags and designer dresses with her now-signature ease. Expanding into retail was always part of the plan—flourish as a hairstylist, then use that to take another crack at fashion—but there was another motivation, too. More than anything, Monahan seems driven by a need to prove she can make it on her own—and make it more than once. "[Success is] making people proud of you and being independent," she says. "I look at my mother, who couldn’t help being dependent, and I say, How dare people who have choices not regroup and go back smarter, tougher?