Regrets — we have only one. Why, why, why, in the early ages of the internet, didn't we have the foresight to buy up a bunch of generic domain names for cheap? If we had, we could be making $70 million a year like this guy.
Just to rub it in your face a little more, Complex has put together a list of the 20 most expensive domain names ever sold. As you may have guessed, numbers one through five are all about either money or sex (what, no Refinery29.com?), and many of the multimillion-dollar sales are mired in legal controversy and shady dealings. The sky-high prices for things like "Clothes.com" and, if you can believe it, "Candy.com" are certainly representative of the Internet's first golden age, when the user's idea of fun was booting up the old Compaq for some good old-fashioned AOL dial-up browsing — a business that, by the way, still makes over $500 million a year, more than the rest of AOL's other profits combined.
Today, a lot of people are still making money through ads on sites people visit due to common typos — like Nytimes.cm, for example. But as for those generic names like Clothes.com, who's really making that mistake anymore? Aren't people savvy enough now to know those domains are either just pure advertising pages or funnels to other sites? Or are we being too optimistic here?