Oli Dale has done a pretty thorough roundup of the history of WordPress websites and businesses that have been purchased. I’m a little disappointed that so many people do not reveal the price of their transactions. I know there is no obligation, but it would be interesting to see for sure. I also added a couple of extra details about WP Designer and WP Tavern in the comments.
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If you only knew the trouble I got into for opening my big mouth, exposing the numbers that I did.