Rossetto was born and grew up on Long Island, New York. He went to Columbia University as an undergraduate and later returned for an MBA. In the early 1970s, he wrote a novel called Takeover. Several years later, he ghostwrote a book about the making of the film Caligula called Ultimate Porno. In 1971, he appeared on the front page of the New York Times Sunday Magazine.
In 1985, Rossetto joined the staff of a translation company in Amsterdam, INK Taalservice. INK launched an English-language magazine in 1987 with Rossetto as editor called Language Technology which covered the technologies used to process language. The magazine was later sold to a small Dutch media company and renamed Electric Word. It was terminated in 1990 due to insufficient revenue.
In 1991, Rossetto and his partner Jane Metcalfe resettled in the US to raise capital for Wired. They launched the magazine on a shoestring budget in January 1993.
Wired was greatly admired for its bold design and its coverage of "digital culture". The magazine exuded a counterculture ethos—and was even compared to Rolling Stone as a barometer of the zeitgeist of the era. Its often deliberately provocative editorial reflected Rossetto's beliefs in a far-reaching "digital revolution" based on global consciousness and networked markets. Under Rossetto's five years as editor, the magazine won two National Magazine Awards for General Excellence, and one National Magazine Award for Design.
In October 1994, Wired Ventures became an Internet pioneer when it launched the first Web site with original content and Fortune 500 advertising called HotWired. HotWired then proceeded to launch dozens of other Web sites, including Webmonkey and the search engine Hotbot. Hotwired employees Joey Anuff and Carl Steadman launched the first weblog Suck.com.
After HotWired, Wired expanded into books with HardWired and television with Wired TV. By 1996, it had Japanese and British editions, and was actively planning a German edition, as well as new business and design magazines.
Wired Venture's rapid expansion forced it in 1996 to turn to an IPO for financing. But after failing to take the company public as scheduled during what turned out to be a severe stock market downturn that summer, Rossetto and Metcalfe were forced to accept Providence Equity as financial partners in early 1997. By the summer of 1997, four years after launch, Wired magazine was solidly profitable. Its three-year-old online business, now renamed Wired Digital, was not. It was Wired Digital's cash needs which Providence used to wrest control of the company from Rossetto and Metcalfe in April 1997.
Despite Wired Ventures becoming cash-flow positive in May 1998, Providence sold off its assets. The company that Rossetto and Metcalfe began in 1991 with $30,000 was sold in pieces for $380 million. Condé Nast bought the now 500,000-circulation Wired magazine, and Lycos bought Wired Digital.
Since Wired, Rossetto has mostly avoided the public eye, although he assisted with a 2001 redesign of Reason Magazine and defended the invasion of Iraq in its pages. He pursued individual projects through his and Metcalfe's Força da Imaginaçao holding company.
Currently, Rossetto is CEO and CCO of the chocolate company, TCHO.