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About $4K by one of the first live video sponsors when they went tits up; 5-figure losses courtesy of Globill and the other payment processor which went pear-shaped around the same time in what, 2003 (?); several small amounts via vanished sponsors (mainly dialers): a little over $40K in total, already billed.
The one which p*ssed me off most, although the amount of money was very small, was Adult Check, because of course they stayed in business and among the people still happy to work with them are some well-known webmasters. I thought that was a very dangerous precedent for the industry.
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