Cover Story February 10, 2011, 5:00PM EST

Cheating, Incorporated

(page 6 of 7)

Another woman—"luckyjane"—said she worked in finance and described herself as a "risk taker and seeker by nature." Her photo made her look sort of dominatrix-ish—she had long blond hair and wore a tight black outfit showing lots of cleavage, and she said she was single. "You may or may not be surprised at the number of people on the street who are on here looking for something 'strange,'" she wrote. "Being a woman on wall street is a unique experience, but I will say regardless of that, spouses can never fully understand the pressures and resulting need for extracurricular releases...and this does not even address the number of guys on this site not on wall street, who are stuck in loveless, sexless marriages. This site is enormously interesting."


"Next to Facebook, we're probably going to be the fastest-growing social network on the planet," Biderman says. Next to defending adultery, Mark Zuckerberg's company is Biderman's fastest-growing obsession—an inspiration, a competitor, and a cruel gatekeeper. "It really baffles me that a young startup company like Facebook won't take my ad," he says. "It really, genuinely baffles me. I don't know what they're playing at."

Biderman was sitting in his office, waiting for an interviewer to arrive from his alma mater, York University's Osgoode Hall Law School. The conversation had turned, once again, to the subject of how unfairly he is treated in the marketplace. "How many companies do you know, if they wanted to buy their own brand as a key word in a search engine, like MSN, they can't even do that, can't even defend their own territory?" he asks. "Can't buy the word 'infidelity,' which is troubling, I would think. I think it's my role in that conversation to say, hey, isn't that a problem?"

This proved to be a big problem last year, when Avid Life Media attempted to raise C$60 million through a private placement of shares, with plans to go public through a reverse takeover of a shell company on the Toronto Stock Exchange. The deal was a disaster. Ashley Madison had become infamous by then after unsuccessfully lobbying the Toronto Transit Commission for the right to plaster advertisements on city streetcars. The company had been struggling to find a way to grow since 2006, when Biderman needed to raise C$10 million to buy out his partner Morgenstern. Biderman says his investors wanted him to branch out into other businesses beyond the affairs market, so Avid Life was conceived as a "diversified media company," and it bought Web properties dealing with real estate, green living, and pets. (Biderman continued running Ashley Madison while an outside CEO ran Avid Life until Biderman was given the CEO job last June.) The strategy shift didn't work out, so a decision was made to focus the company exclusively on online dating, and Avid Life bought hotornot.com for $22 million and launched establishedmen.com, cougarlife.com, and several others.

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