The $23 Million Boa

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

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."

photo: Stacy Kranitz

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."

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