At time of its bankruptcy filing, OptInRealBig.com claimed assets of less than $10 million and liabilities of over $50 million. Richter claimed his company made $15 million a year sending more than 15 million email messages per day. However, in 2003, OptInRealBig was dealt a powerful 1-2 punch from Microsoft and Eliot Spitzer, Attorney General of New York; both sued Richter under local state anti spam laws. Although New York case was settled out of court last year, Richter has had no such luck dealing with Microsoft, whose claims top $19 million.

A Case of Global Amnesia? Richter's company and others like it market products ranging from diet pills to pornography. He’s also been accused of using spam to extract personal information from unsuspecting recipients. For instance, one alleged scheme hatched by Richter and his associates promised recipients a copy of a "Girls Gone Wild" DVD if recipient registered on a website. The registration information was then used to bombard recipient with more and more spam.

Richter contends that his methods are all legal, and that he’s just a regular guy trying to do right by world; he’s even gone so far as to claim that he’s a “victim” of overzealous anti spam companies and prosecutors. “We don't spam,” explained Richter in an August 2004 PC World interview. “The biggest problem is when people get an email that they think they didn't sign up for or don't remember signing up for, and they call it spam.”

However, Jaynes ran head-on into an information superhighway road block when a Virginia judge sentenced him to nine years in prison for his November 2004 conviction on felony charges of using false IP addresses to send mass email advertisements (some just call it spamming). The conviction was a landmark decision, as Jaynes became first person in United States convicted of felony spam charges. Though his operation was based in North Carolina, Jaynes was tried in Virginia because it is home to a large number of routers that control much of North America's Internet traffic (it’s also home of AOL and a government building or two).

He should’ve Used Privacy Software During trial, prosecutors focused on three of Jaynes’ most egregious scams: software that promised to protect users' private information; a service for choosing penny stocks to invest in; and a work-from-home "FedEx refund processor" opportunity that promised $75-an-hour work but did little more than give buyers access to a website of delinquent FedEx accounts. Sound familiar? Anyone with an e-mail address has received countless messages originating from Jaynes’ operation. (If you’re still waiting on your privacy software to show up, it’s probably safe to stop checking mailbox.)