It looks so simple. A database, a web interface, a bit of code: you now have an online classified advertising site. And here’s the strange thing. It doesn’t just look simple. It is simple. A sincere, dedicated effort to provide free or very cheap classifieds listings in a local market is probably doomed to succeed.
But if you really want to see a mess, go visit the nation's greatest apartment-hunting site, the first likely choice of anybody searching for a rental or a roommate. On this site, contrary to every principle of usability and common sense, you can't easily browse pictures of the apartments for rent. Customer support? Visit the help desk if you enjoy being insulted. How much market share does this housing site have? In many cities, a huge percentage. It isn't worth trying to compare its traffic to competitors', because at this scale there are no competitors.
Each of these sites, of course, is merely one of the many sections of craigslist, which dominates the market in facilitating face-to-face transactions, whether people are connecting to buy and sell, give something away, rent an apartment, or have some sex. With more than 47 million unique users every month in the US alone—nearly a fifth of the nation's adult population—it is the most important community site going and yet the most underdeveloped.
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