The $23 Million Boa

Despite her huge payday, Mediabistro mastermind Laurel Touby still stands outside the press-gang elite

Laurel Touby's feathers are floating everywhere. They land in glasses of wine, dot expensive suits worn by square-jawed TV newscasters, and catch on the glossed lips of girls spackled with pancake makeup.

The feathers come from a white boa, a fashion signature that has made Touby, a former so-called "desperate freelancer," instantly recognizable—and instantly mockable. When she sold her company, Mediabistro—part–job board, part–workshop hub, part–media-gossip center—for $23 million in July, people wondered how a cheap feather boa could be worth so much. She doesn't remember how it caught on—someone suggested she wear a boa so people could easily recognize her at Mediabistro parties. Now there's an assortment of them in her office: purple, orange, red, green, pink, and white. "Men love boas," she explains. "It makes a woman seem more approachable—tactile, even." Mostly she buys them from House of Feathers on 40th Street for $7 apiece, though one prize boa, an ostrich number, cost her $250. Suddenly, that doesn't seem like such a splurge.

Unlike her peers, Touby isn't considered a media insider. She doesn't rub shoulders with New York Times honcho Bill Keller or her Internet rival, Gawker's Nick Denton. She has only been to the industry's current power center, the Waverly Inn (owned by Vanity Fair editor Graydon Carter), twice— and even then it was the chef who invited her. Yet here at Michael's—another favorite of media navel-gazers, where Media- bistro conducts its Wednesday head-count column, "Lunch at Michael's"—Touby holds court in a room swelling with big shots (media writers, TV network presidents), who are there to send off her popular blogger, Brian Stelter (a/k/a TVNewser), who the Times poached just in time for his college graduation. People line up to congratulate Touby on her windfall. Regardless, "I still feel like an outsider," she says. "Absolutely."

photo: Stacy Kranitz

Though only five-foot-one, she has what a psychic would call a big aura. Her laugh— another reason people love to make fun of her— is part-chortle, part-snort, part-cackle. Tonight, though she's dressed up, she's not really put together. She doesn't wear much makeup—her reddish tortoiseshell glasses do much of the decorating. The 44-year-old's blond hair has streaks of gray in it; though it's straightened, the humidity makes it a bit frizzy. Her Pucci dress doesn't hang elegantly, because Touby, a former athlete and daily gym rat with a lithe, toned figure, stands with her legs apart, like a jock. (She still boasts that in fifth grade, she could run faster than all the boys.) At Michael's, she swaps her orange flat sandals for gold Gucci heels.

Even glammed up, Touby is still a bit geeky. "She's not cool, she's not removed, she's not studied," says her friend and former employee Greg Lindsay. "She's not snarky, she's not bitterly ironic. Laurel is an extremely earnest person."

In her new role as senior vice president, she still oversees Mediabistro but reports to the company's new overlords, the Connecticut firm Jupitermedia. And though the sale netted her an estimated $12.4 million personally (she held 62 percent of the stock) and stands to generate another $1.9 million over the next three years, Touby still longs for acceptance. "When they want to promote their book, the media elite don't mind my call," she says bitterly. "There is a media elite, and don't fool yourself into thinking there's not. I've met them."

Thirteen years ago, Mediabistro was just a nameless, informal, semi-regular party started by Touby and former Voice investigative reporter Russ Baker, whom she'd met at a cafe in the East Village. He suggested media salons. She had a handful of friends; he had a few more. They convened at Jules Bistro on St. Mark's, Touby handling the invites when Baker got too busy. After a few calls, she realized most of Baker's contacts were only casual acquaintances. "That's when I realized I can invite people I didn't know and make it better," she says. "I started inviting people I wanted to meet or write for."

In those pre–e-mail days, Touby, then an unknown writer, cold-called some of the biggest names in the business. Anthony DeCurtis at Rolling Stone. Alan Light, Spin's then editor in chief. "I thought maybe the cool kids would come—high-level cool kids," she says. "And they did!"

Others weren't so nice: "Some people were so full of attitude, they literally hung up on me, and some people were like, 'What is this? Is this a PR person?' They were baffled." It was humiliating, but she doggedly kept at it. "I felt like I was a salesperson," she admits.

The first parties were small—maybe 10 people. Within a few months, the list swelled to 100, and the crowd, now unofficially known as "Laurel's Press Club," moved to Flamingo East. Touby started an e-mail newsletter around 1996, announcing readings, apartment listings, events, and most importantly, jobs. Someone suggested she put it online. But Touby wasn't Internet-savvy herself, so the listings started on someone else's site. As she hammered away at her own writing career, the business grew. By 1999, the HR people posting job listings on her directory started paying—Touby picked $100 because it was a nice, round number. That month, eight checks rolled in, then 16, 25, 35, 45.

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