Why Craigslist Is Such a Mess

Should craigslist ever be sold, the price likely would run into the billions. Newmark, by these lights, is a very rich man. When anybody reminds him of this, the craigslist founder says there is nothing he would care to do with that much money, should it ever come into his hands. He already has a parking space, a hummingbird feeder, a small home with a view, and a shower with strong water pressure. What else is he supposed to want?

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Newmark’s claim of almost total disinterest in wealth dovetails with the way craigslist does business. Besides offering nearly all of its features for free, it scorns advertising, refuses investment, ignores design, and does not innovate. Ordinarily, a company that showed such complete disdain for the normal rules of business would be vulnerable to competition, but craigslist has no serious rivals. The glory of the site is its size and its price. But seen from another angle, craigslist is one of the strangest monopolies in history, where customers are locked in by fees set at zero and where the ambiance of neglect is not a way to extract more profit but the expression of a worldview.

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Craigslist gets more traffic than either eBay or Amazon.com. eBay has more than 16,000 employees. Amazon has more than 20,000. Craigslist has 30.

I want to quote half the article but I think you should just read the whole thing.