Why can't magazines get the Web?

"Branded entertainment is the new advertising," says Jimmy Jellinek, an executive hired to oversee Playboy.com's extensive, soon-to-be revealed digital overhaul. "You sit down, figure out the brand values, create a program; it can be a viral video, a written piece, anything in your imagination. You have to be as flexible as possible."

But magazine mega-publishers are clearly reluctant to make this leap. Condé Nast made some promising moves by purchasing the social media site Reddit and the Web publication Ars Technica in recent years. Yet the company has long neglected to build the necessary infrastructure—from software to writers—to be a competitive presence on the Web. When Condé Nast bought Wired magazine in 1998, it didn't even bother to buy the Web site. Former Condé Nast staffers from the magazine Web sites say that it was a bureaucratic nightmare to get desperately needed technical staff or even the most remedial features added to the magazines' bare-bones Web sites. In most cases, the company insists that new site technologies be developed by nail-bitingly slow internal IT teams rather than using high-quality, inexpensive technologies widely available on the market. It took one editor a whole year just to obtain a flash audio player. The company has famously refused to make magazine content available online and has not been willing to hire a generation of writers to create original content.

"You live and die by the quality of the content you create," says Jellinek. "If you're just a magazine clone, you're never going to attract an audience. The failure of [Condé Nast's] Web sites is a failure of vision and ability to translate the DNA of their titles into an online environment."

"They've been willing to lose $100 million to make a magazine profitable," adds a former Condé Nast online employee. "But for some reason, they've never been able to apply that thinking to the Web."

Ultimately, it comes down to trickle-down attitude and changing a deeply entrenched magazine culture. When magazines first began to go online in the mid- to late-90s, their corporate imperative was often to promote subscriptions to the print publication, not to create a new medium. And countless reports from inside Condé Nast confirm that this is still the thinking at the top—the Web is there to drive print subscriptions, nothing more.

And if magazine publishers were disinclined to build this infrastructure when they were relatively flush, now all of their dwindling resources are going to shore up their core products, making a meaningful transition online even less likely.