Career
During the dot-com boom, Calacanis was active in New York's Silicon Alley community and in 1996 began producing a publication known as the Silicon Alley Reporter. Originally a 16-page photocopied newsletter, as its popularity grew it expanded into a 300-page magazine, with a sister publication called the Digital Coast Reporter for the West Coast. Calacanis's tireless socializing earned him a nickname as the "yearbook editor" of the Silicon Alley community. With the end of the Dot-com bubble, Silicon Alley Reporter failed.
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