MrHen comments on The Craigslist Revolution: a real-world application of torture vs. dust specks OR How I learned to stop worrying and create one billion dollars out of nothing - Less Wrong
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So, I guess the first step is finding out how many people we need to get Jim's attention.
50K is a good guess but anything we can do to get a more accurate answer will help.
Your answer for closing the ad works. Is there anyway to find out more details about much that hurts the dollar value? I imagine that someone, somewhere runs ads like that.
You should be able to set an easy lower bound on this. You said, "With 20 billion pageviews a month, a Google Adwords banner would bring in about 200 million dollars a year." Just find actual quotes and keep track of the information. Shop around a bit.
Or find a volunteer around here willing to do it.