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A good read:
Read the full thing--it's interesting: http://www.domainpicks.com/13736/how-i-aready-lost-money-on-a-new-gtld/
have already lost money on .web, in 2000 Image Online Design put in an application for .web and sold pre registrations, I paid for about a dozen huge word.web domains, lots of people did, it was a first come first serve system and if I remember correctly they were at least $35, I know lots of people did because most of the words I would check were already paid for or going quick, they sold lots of pre registrations. Unfortunately the application was not approved in that round and there was no .web and no .refunds, there is a .web coming now though, I wish my pre registration backorders were still good.
Read the full thing--it's interesting: http://www.domainpicks.com/13736/how-i-aready-lost-money-on-a-new-gtld/