[citation needed] Pearlstine worked for the Wall Street Journal from 1968 to 1992, except for a two-year period, 1978–1980, when he was an executive editor for Forbes magazine.
[8] After leaving the Wall Street Journal he launched SmartMoney and was later the general partner of Friday Holdings (along with Richard Rainwater, Barry Diller and Paramount Pictures chief Martin S. Davis), a multimedia investment company, prior to succeeding Jason McManus as editor in chief at Time Inc. in 1995, the first outsider in the position.
[13] In that role Pearlstine was charged with seeking growth opportunities for Bloomberg's television, radio, magazine, and online products and to make the most of the company's news operations.
[20] In the same year, he married Jane Boon, an industrial engineer and the author of the novels Edge Play and Bold Strokes.
Pearlstine received the 2019 Medal for Lifetime Achievement in Journalism from the Poynter Institute during their annual Bowtie Ball on November 2, 2019.
[29] Pearlstine was briefly part of the controversy surrounding Matthew Cooper when, after the United States Supreme Court refused to review adverse lower court decisions, he gave Cooper's notes to the independent prosecutor investigating the outing of Valerie Plame as a covert agent of the CIA.
[30] From this experience, Pearlstine wrote a book entitled Off the Record: The Press, the Government, and the War over Anonymous Sources for Farrar, Straus and Giroux.