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As far as money goes, Danni from danni.com is the most successful. I doubt she does much webmistress work anymore though. I heard she did in the beginning. Jenna Jameson is also very successful, but I wouldnt consider her a webmistress. I think her husband Jay handles most of her online business.
As far as most successful "real" webmistress, I would go with PersianKitty, because she probably knows html, how to upload files, and do real webmaster work.
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