The $23 Million Boa

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.”

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.

“That’s when I knew: ‘Wow, this is real money,’ ” she says. “I went to bed a writer. The next day I envisioned myself as a company owner.”

Ironically, all the personal contacts she’d made at her parties had started paying off—she’d written stories for New York magazine, with other major glossy pieces in the works. She was finally cracking her coveted media elite.

She called her editors and canceled those assignments.

She bought business books, asked CEOs for advice, and set about getting funding. She approached Dan Kunitz, a writer, because he seemed like a guy who knew the right people: “I ran into him at an event, and I said, ‘Hey, do you know any rich people?’ ” She splurged and took him to lunch at Balthazar. “It was the best $50 I ever invested.”

Kunitz introduced her to New Republic founder Martin Peretz, who along with the hedge-fund company Gotham Partners, became Mediabistro’s principle investors. In March of 2000, the stock market crashed, and Touby fell short of her initial three-year projection of $25 million in gross sales. She was working in shifts out of her bedroom with two low-paid jacks-of-all-trades before eventually getting a real office on 17th Street. After 9/11, the publishing industry took a hit, and the job listings dwindled. Allen Salkin, a Times reporter, gave her the idea to start classes. It saved the company. By 2004, Mediabistro was profitable.

While she often works off other people’s suggestions, Touby is the one who takes action. Former editor Elizabeth Spiers had suggested the “Lunch at Michael’s” column, which had been suggested to her in turn by Spy magazine founder Kurt Andersen, who said he’d read the site if it simply listed the people who appeared at the media haunt daily. Months passed, until Touby herself finally went to the restaurant, pad in hand, boldly asking people who they were. Eventually, the participants began to call in their names themselves.

Touby recalls her first meeting with Baker: “I’ll never forget it. He looks at me and says, ‘You’re not one of those people who says they’re gonna do something and doesn’t follow through with it, are you?’ And I was like, ‘No. If I said I’m gonna do it, I’m gonna do it.’ ”

Mediabistro sells hope—some might even call it false hope. In a collapsing industry—Jane magazine closing, the Los Angeles Times cutting nearly 150 jobs—Touby’s workshops have a consoling effect. An unknown writer in a backwater town can learn how to pitch The Fader, Glamour, or Blender. Take “Breaking into Freelancing,” “Breaking into Narrative Journalism,” or “Ace Your Edit Test,” and you too can succeed in the publishing world. The company placed its first-ever ad in Time Out this month, headlined “Be a Media Star.”

But more than a few people actually got a foot in the door, got agents, got book deals. Huffington Post blogger Rachel Sklar, who started as an ex-lawyer from Toronto looking for a journalism break, found her first jobs on the site; she took the classes, went to the parties, and even briefly blogged for FishbowlNY, the site’s media blog.

“I was totally sold,” says Sklar. “Everything happened through Mediabistro—that was the source of all my journalism knowledge, awareness, and contacts. It was a full package deal.”

A lot of people—600,000 unique subscribers, to be specific— are buying into Mediabistro’s dream. An additional 12,000 Avant Guild members pay $49 a year for access to the useful “How to Pitch” series, Lexis Nexis search-engine access, and health care, while 15,000 students choose from 410 classes at $499 each, with more options available online. The job listings alone cost $279 a pop, with around 1,800 running at a time, about 85 percent of those new additions month to month. It’s understandable why someone would pay $23 million dollars for all this.

Breaking up cliques, hoping to start up new ones photo: Isabelle Mills-Tannenbaum

Touby shopped Mediabistro for a few years; Jupitermedia, a relatively new company, finally bought it. CEO Alan Meckler marvels that the deal only took three months from the original meeting to the final sale—impressively, even in that short a time, he’d watched the site’s numbers grow exponentially. He also liked all the original content driving recurring traffic—something not so prevalent on similar sites like Monster.com. He plans to expand Mediabistro’s listings and classes (especially within photography and graphic design, Jupitermedia’s specialties), while adding live webcasts and “webinars.”

Peers reacted to Touby’s big payday with derision and disbelief. Even the most positive piece of press, Simon Dumenco’s New York article about the sale, was littered with backhanded compliments: Touby is a “secret genius.” She started out a “desperate freelancer.” Her early events were “anti-loneliness cocktail parties.” Such descriptions burn her. “I don’t like it when people always put ‘desperate’ in front of ‘freelance,’ ” she says. “The word ‘lonely’— I didn’t have an office. That I didn’t have people to hang out with didn’t mean I was a desperate, lonely freelancer.”

The irony of Mediabistro’s success is that its guiding light notoriously lacks certain skills you’d expect a professional party hostess to possess: the ability to remember faces and names, for one thing. “That’s what pisses people off,” notes Kyle Crafton, who served as her chief financial officer from 2002 to 2007. Numerous employees at the small company say Touby didn’t know who they were when they met at events. She frequently doesn’t recognize boldface-name media personalities, and she even blanks on celebrities. “Occasionally, she’ll be looking at Britney Spears on 80 magazine covers,” says her husband Jon Fine, a
Business Week reporter. “And she’ll be like, ‘Who is that?’ ”

Her most famous gaffe, though, came at Time editor Jim Kelly’s house in October 2005, when a short, older man introduced himself around the room. Touby asked him to say his name again.

He politely reintroduced himself: “Mike Bloomberg.”

Touby groans at the memory. “I was horrified—especially since it was in front of a room full of journalists. You know that disease called prosopagnosia? I am convinced I have that.”

Her hostessing technique is practical, but brusque: She forcefully moves people around, interrupting happily flowing conversations to start new ones. “She really focused on making people meet and saying, ‘You need to talk to this person,’ and making sure people weren’t standing alone,” Crafton says. “That shows a pretty compassionate side. If she feels a group is getting clique-ish, she’ll break that up.”

“I have these social antennae that work in a different way than most people,” Touby says. “It’s more about what are the big needs of the room, and how can I help hook those up. My job is to connect the job titles.”

Though she frequently plays 20 questions with strangers, “I’m not really a people person,” she insists. “I’m actually kind of a misanthrope. That is the irony.” As a boss, she fears she’s not good at setting boundaries, often mixing the personal and the professional. When she got married in the midst of a move, she listed Mediabistro as the return address on her invite, paying her employees extra to help run her wedding. “I’ve never sent anyone to get my laundry,” she says. Though she cheekily signs memos “She who must be obeyed,” you get the sense that Touby wants to bend the world to her will. Crafton recalls that Touby demanded that a cabbie drive in reverse against oncoming traffic on Broadway because he’d missed a turn.

Jesse Oxfeld, a former Mediabistro employee who publicly feuded with Touby after moving on to Gawker, was one of the few who took the stock option upon exiting. (“I knew it would drive Laurel crazy to have to write me a check,” he says.) He got a low five-figure cut from the sale; he recalls that when a dividend check arrived, Touby had added a note reading: “You’re so lucky.”

Oxfeld, like other employees, found her micro-managerial style “challenging. I remember being lectured extensively on how I wasn’t licking envelopes closed properly. She has a very specific way to do things.” Colleagues reveal that the staff found creative ways to deal with Touby’s sometimes invasive tendencies. “When I was there, we would try to find trips to send her on for as long as possible, because the office got more done when she wasn’t in the office,” says one.

Most Touby lore, however, suggests a well-meaning person who frequently puts her foot in her mouth with bawdy, inappropriate comments. “There was a lot of joking that I had an enormous stack of sexual-harassment paperwork that people could fill out,” recalls Crafton.

“I’m very jocular,” Touby says. “If I said anything ever, it was intended in jest. And, of course, now that I am with a corporate entity, these things will never happen.”

She’s only half-joking, but sometimes her jokes unintentionally sting. She once held a party celebrating a longtime employee; making one of her famous speeches, Touby asked him to publicly name his least favorite former employee. “You should have seen the jaws drop around the table,” recalls one guest.

Even early on, Touby’s outsized personality was controversial. At her first job for an advertising agency, her boss scolded her for “being mean,” telling her: “We’re going to have to prune you, Laurel. Your personality is just a little too personality for this place.”

That said, most people don’t think she’s a devil wearing Pucci. “I think she’s an entirely well-meaning person,” says former employee Aileen Gallagher. “I don’t think Laurel has a lot of malice in her. I really don’t.”

But she is a paradox, capable of being warm and rude at the same time. Crafton says she’ll spend hours planning people’s birthdays and getting them a specific cake they’ll like, only to undermine the moment in a particularly Laurel way: “Maybe there was a slightly overweight person, and she’d be like, ‘Maybe you shouldn’t have that cake.’ ”

Indeed, while hanging out with her, I experience a few Laurelisms. On the subway to Michael’s, she’s wearing one of her best dresses, an expensive, multi-colored, ’60s-style Pucci. She explains that since we’re going to a TV party, she’s dressing up. “Normally,” she says, “I would just dress like you. Cash.” She means “casual,” though my “cash” outfit consists of dress shorts that cost me a couple hundred dollars. It was just a tiny, offhanded jab, but you could imagine how hundreds of those would drive a person slowly crazy.

Later, though, when I tell her about other people’s impressions, she’s appalled and genuinely concerned. “I think some people respond to my style better than others,” she says. “Maybe I should be more ginger in the way I handle people. But sometimes I feel like I’m a nurse, tending to the wounded.”

A few minutes later, she snaps at the waitress removing our bread basket, then pauses, looks at me sheepishly, and asks if that was “awkward.” Generally, though, “she’s got no sense of awkwardness,” says Crafton. “That’s the reason why she was able to meet this many strangers and start these parties. It basically translates to fearlessness.”

Touby grew up in Miami, raised, along with a younger brother, by her single mother, constantly moving, always the new kid in school. Her father left for reasons that are not clear, but her paternal grandfather, the construction tycoon Harry Touby, also took care of her, leading to a dual existence that had Laurel fluctuating between a financially unstable home and a lavish and luxurious one—she even had a horse. “When we would stay at his house, it was wonderful,” she says. “It was like Disneyland. When we were with my mom, it was scary a lot of times.”

She majored in economics at Smith College and briefly worked in advertising before petitioning Working Woman magazine, even though she had no experience. The person who hired her, Basia Hellwig, remembers that Touby mailed in a hand-written card listing “Seven Reasons You Should Hire Me.”

A stint at Business Week followed, then freelance gigs for Glamour and other publications. Touby gave me a few old clips: One is a well-written, if fawning, New York profile of Perfect Storm author Sebastian Junger. But her business articles are particularly prescient, with headlines like “Nail Your Next Job Interview!” and “Be Your Own Boss and Earn Up to $200,000.” In the latter, she writes, “Stop dreaming and get going!”

Exactly a week after the Michael’s bash, Touby hosts a party at Jules Bistro for her early supporters, including Salkin and Baker, who’s launching an investigative news site called the Real News Project. It’s an outgoing bunch—it’s hard to believe they were ever desperate or lonely. Evan Schwartz, a former Business Week colleague, gleefully recalls those early parties as involving more dating than networking. (Touby despises the N-word.) “At one of her early parties, I swear to God, she came up to me as I was talking to some woman, and Laurel said, ‘Sex, sex, sex, sex, sex, sex, sex!’ and walked away.”

I ask if there’s anything Touby wants to say to her detractors. “It’s weird—the biggest critics are the ones who understand the least about who I am,” she says, whipping out liquid eyeliner to get fixed up before the crowd arrives. “I would just say . . . ” She drifts off for so long that I think she’s forgotten the question. “I’m so misundastood,” she finally finishes, in a Southern hip-hop drawl. She throws her head back and cackles—that awkward, loud, brash laugh. “You know that song by Pink? I feel like they just don’t get it. They’ve never been around me or the parties or the site—they’ve been looking from the outside in.”

She scrambles to finish her makeup. Tonight, she has her hair tied up in a bouncy ponytail and is wearing a black-and-white polka-dot dress. No Pucci. Totally cash. The boa is M.I.A. “No. Nooooooo boa,” she says. “These people know me; they are gonna find me in this room. This is the first party I’ve had that I don’t have to wear a boa.”