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He graduated 341st out of a class of 355 from Northwood High School in 1984.
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He worked odd jobs and at a local 7-11.
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He moved to a Hollywood apartment and got a job in the gift shop of CBS studios, eventually working his way up to manager.
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The Drudge Report began as an e-mail sent out to a few friends, but the newsletter transitioned slowly from entertainment gossip to political gossip and moved from e-mail to the Web as its primary distribution mechanism.
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Drudge's website gained in popularity after a number of stories which he reported before the mainstream media did. By 1997, Drudge had 85,000 subscribers to his e-mail service
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A story by Business 2.0 magazine from April 2003 estimated that Drudge's website received $3,500 a day (almost $1.3 million a year) in advertising revenues. Subtracting his relatively minor server costs, the magazine estimated that The Drudge Report website netted $800,000 a year.
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Today, Drudge maintains the website from his two properties in Miami. In updating the site, he reportedly monitors multiple television news channels and a number of websites on several computers in his home office.