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Rule No.1: Pick a market where the competition charges money, and do it for free.
Most people looking for dates online paid hefty monthly fees for personals ads before entrepreneur Markus Frind came along. His site, Plenty of Fish, undercut the competition including Match.com. In that way, Frind was quickly able to grab market share. He's now tops in the U.S., according to Hitwise, a firm that measures website traffic. And better yet, some of Plenty of Fish's biggest advertisers are the very same paid sites against which his business competes.