Most journalists know Mediabistro  as a freelancer’s resource, a place to scour job boards or enroll in classes on pitching magazine editors, copyediting, video production or "How to Write Chick Lit ." Or perhaps they’ve come across its various media blogs such as FishbowlNY  or TVNewser . But it didn’t start out that way. In fact, it started out as anything but. And its entrepreneurial founder? She started out as anything but, too. But it--and she--pivoted many times along the way.
In the early 1990s, after stints in advertising, woman’s magazines and business reporting, Laurel Touby was in her mid-thirties and living the less-than-glamorous life of a freelance writer and editor working out of her Manhattan apartment. A sociable person by nature, Touby found it isolating, and to combat her feelings of loneliness she often repaired to cafes to work. One day she struck up a conversation with a fellow freelance writer--she could tell he was a journalist by the stack of newspapers and magazines he was reading (remember?).
One thing led to another and they decided to co-host a high-minded salon where guests would talk about ideas and issues of the day. But their real agenda was to score work and meet members of the opposite sex. Soon after, they each invited 10 magazine and newspaper editors and held their first party at a French bistro in Manhattan’s East Village. It was a success, so they decided to make it a regular event. Soon word got out, so Touby unclasped the velvet rope to let in writers whose work she respected, and it snowballed from there. One week her friend got busy and couldn’t make it, so from then on Touby hosted the parties herself.
Back in those days I attended some of her parties, as did virtually every writer and editor I knew. And there was Touby bouncing around the room, wearing a feather boa so people could easily spot her in a crowd. She made it a point to greet every invitee and introduce him around. “I wanted every person to walk out of there and feel like they really connected with somebody on a deep level,” she says. She likened her job to being a dominatrix, because she quickly learned that people want to be guided; they don’t like to feel like random particles when they enter a room full of strangers.
But party planning is a lot of work. She had started out in the days before the wide adoption of email and either mailed invitations or called or faxed (remember?) editors. Then, in the early days of the web, she could email only 10 people at a time from her AOL account to a list of more than 600 people. Eventually she started a newsletter, which she paid for herself. “I knew it was a valuable service because I was offering jobs in the newsletter, apartment listings and event listings,” she says. “But I didn’t realize that I could make money, although I thought, ‘You know, there’s something here. I just have to wait and see where it takes me.’”
When she migrated to a website the two most popular sections were jobs board and the bulletin board, where writers went to gossip. She knew she had the makings for a business when one day in 1997 she overheard a woman telling her friend about this amazing job board. It turned out it was Touby’s. What’s more, the woman didn’t know about the East Village soirees. “That’s when I realized this thing has gone beyond little cocktail parties,” she says. But when she queried publications and users on whether they would pay for the site, the answer was a resounding no.
Nevertheless, Touby kept at it and two years went by. By then she had thousands of names in her database, the site had become a freelancers’ destination and her parties were popular. Touby started by sending out a mass email asking recipients to pay $100 if they were happy--and only if they were happy--with the site. The first time she checked her P.O. box out came 16 checks. The next month, 35 checks. She decided to write a business plan and raise $1 million. Eventually she met Martin Peretz, who at the time co-owned The New Republic, and he agreed to invest $250,000, but only if she could locate a lead investor. Some days later she called Peretz and said, “I don’t like the terms my lead investor is giving me. Do you have another lead?” Actually she was bluffing--and it worked. Peretz introduced her to another money man to put up the lion’s share of capital. She called her new business Mediabistro.
Just as she was about to officially launch, however, the market tanked, a victim of the dotcom bust. Somehow Touby managed to keep her fledgling business, which was largely fueled by the jobs board, afloat. She offered freelancers health insurance, which she thought would be a healthy revenue stream, but it didn’t take off. Then customers stopped paying bills. Invoices went unpaid and every week she got bankruptcy notices from dot coms going bankrupt. “Media companies and dot coms were my biggest customers,” she says. “It was scary.”
Then there was 9/11, and the economy deteriorated further. Touby had to figure out how to generate revenue beyond the small amount the job board provided. She organized focus groups over pizza and wine and learned that people wanted training. Touby started with a writers’ boot camp course, then added classes on pitching stories to editors, writing for women’s magazines, food writing, travel writing, and many others. Then she introduced an annual membership to Mediabistro, launched several blogs behind a pay wall, and created special events like media conferences. The once lonely freelancer was now an entrepreneur whose business was generating millions in revenue.
In 2007, 14 years after throwing her first party, Touby, who maintained a 64% equity stake in her business, sold Mediabistro to Jupitermedia (now WebMediaBrands) for $20 million in cash plus a two-year earn-out worth an additional $3 million.
And she owes it all to pivoting.
Adam L. Penenberg is a journalism professor at NYU and a contributing writer to Fast Company. Follow him on Twitter: @penenberg 
[Image: Maria Dryfhout  via Shutterstock]