MP3.com Win In Hand, He Takes Aim At WindowsMP3.com Win In Hand, He Takes Aim At Windows

In one of the defining moments of the classic 1975 film One Flew Over The Cuckoo's Nest, Jack Nicholson's mental-patient character, Randle Patrick McMurphy, tries in vain to pick up a 200-pound washbasin and throw it through a window in an escape attempt. Several patients giggle derisively at his futile actions, but Nicholson turns and says, with defiance, "At least I tried."

It's no surprise that this scene is the personal favorite of Michael Robertson, the man who built MP3.com Inc. into perhaps the first truly viable online music business and is now preparing to bring the world a potentially market-changing operating system. Having taken on the major music labels, and now setting his sights on Microsoft, Robertson might appear to be just as loony as McMurphy. He certainly shares the character's determination. Recently, Robertson visited several venture capitalists to introduce his new company, Lindows.com, and one of them thought the idea so ridiculous that he responded with what Robertson describes as a "nice belly laugh." Robertson wasn't fazed. "A more tender person might have been hurt," he says.

But there's one key difference between Nicholson's McMurphy and Robertson's real-life entrepreneurial persona: Robertson tends to prevail in his endeavors. "If Michael was a horse and you went to the races, you'd never bet against him," says Robin Richards, whom Robertson had hired as president of MP3.com and who's now CEO of Vivendi Universal Net USA Group. When Robertson gets an idea, says Richards, it does not stay just an idea for long: "When he gets it in his mind, it's reality."

Robertson's inspiration comes from a tough childhood. "Being poor stunk," he says. But he also notes that his difficult beginnings made him especially self-reliant, a characteristic he says is necessary when "you do things that are radically different." Robertson doesn't back down from a challenge. After defying the music labels' legal wrath and turning MP3.com into a valuable enough entity that Vivendi Universal scooped up the digital-music site last summer for $372 million, the 34-year-old is confident enough to take on Microsoft.

Lindows.com is preparing to launch early next year an operating system that can run both Linux and Windows applications on a PC, or run as a second operating system on a Windows machine. The point: to offer an alternative to Windows, to eliminate the frustrations that Robertson says accompany installation and use of the Linux operating system, and to let Windows users run Linux programs without having to jettison Windows. If that's not different enough, he'll sell the Lindows operating system for just $99, primarily in digital format, and with flexible licensing.

Once Lindows' installed base is large enough, Robertson's plan is to have Lindows aggregate Linux applications from sites all over the Web and serve as a virtual clearinghouse for them-much as MP3.com does for music that's available in MP3 format. Robertson steadfastly believes that consumers are ready to download operating systems instead of buying them in boxes off retail shelves. And he's surprised that Microsoft hasn't gone that route yet. "It's shocking that you can't buy Windows XP digitally today," he says.

Make no mistake, though: The ultimate success of Lindows is very much up in the air. Linux hasn't proved to be popular as a desktop platform. And it's quite possible that muscling in on Microsoft's turf could get bloody. "Going up against Microsoft has been one of the quickest ways to go out of business. It's certainly a quixotic mission," says Aram Sinnreich, a Jupiter Media Metrix senior analyst. But if anyone can pull it off, Sinnreich adds, it's Robertson. "His role has always been to find the sensitive spot and poke it."