Much has been made of his Philadelphia ties, but up close his affable demeanor seems purely Midwestern. And in fact, his family only settled in the Paoli area as he was entering the eighth grade, after living in Chicago and Ohio.
He graduated from Conestoga High in 1975, and his route to a life in publishing started on a career day in his junior year at Colorado State University. An advertising executive explained that tangible products like printers and cars essentially sell themselves. But people who sell ads for television, print and radio are selling intangibles, like “space” and “time.” The creativity required to reshape what are essentially fundamental concepts in physics into saleable items immediately appealed to Osberg, whose subsequent résumé reflects a striver’s work ethic, with jobs at Chilton Publishing, U.S. News & World Report and eventually two different stints at Newsweek, including one as president.
“No one ever needed a microscope to find Greg Osberg’s ambition,” says his old Newsweek boss, Rick Smith. “But fortunately, no one ever needed a microscope to find his talent, either.”
Smith, a 30-year Newsweek veteran who ran the editorial and business wings of the operation, thought Osberg a singular talent. “Greg has a finger-tip understanding of what the needs and goals of editorial are,” he says, “which I, frankly, don’t understand how he got coming from the business side.”
Having learned how editorial content can define the value of space and time, Osberg soon transcended the normally sacrosanct boundary between advertising and editorial. “The ideas I’d get from salesmen were awful,” remembers Smith. “I once had a salesman come to me and say, ‘You know, if we did a big series on gum disease, I’d be able to sell more toothpaste ads.’”
Osberg, however, arrived with ideas that were motivated by the idea of producing a good read. Once, he suggested a special section of editorial cartoons for the annual year-end recap. “That wasn’t going to attract a single specific ad,” says Smith admiringly. “But it was a sound editorial idea, and advertisers generally like being in a good special section.”
Though Osberg was beloved at Newsweek, he left unexpectedly in 1997, intrigued by the prospect of working online. His new position at CNET put him in “the digital space,” a website covering the technology industry. Osberg generated a 50-percent spike in ad revenue that made CNET profitable.
Newsweek lured him back in 2000, taking advantage of the skill set he had developed and naming him president and publisher. “Greg was way ahead of the curve for the entire industry,” remembers editor Mark Whitaker. “When a lot of people were still saying, ‘Oh, we have a lot of years yet for print,’ he was urging us to develop the online side of the operation.”