The bubbly 42-year-old British expatriate is so much of a fanatic that he knows not only that "Love Will Tear Us Apart," the song the band is covering, was first released in 1980 by Joy Division, but also what was on the B- side ("These Days"). No wonder: Winn has spent his entire adult life in the music business, making tea for UB40 in a Birmingham, England, recording studio before eventually moving to Los Angeles, where among various marketing and producing gigs, he worked for the Japanese rock star Yoshiki.
On this breezy end-of-summer evening, though, Winn is here on behalf of his new employer, Microsoft. The head of artistic development, Winn is part of the team producing Zune, Microsoft's answer to Apple's iPod. His sortie is to integrate the device with the music scene, in part by promoting emerging artists, so he's been checking out music venues like mad since he moved to the area two and a half months ago.
Microsoft hopes that its emphasis on the music itself, rather than just the gadget, will help set Zune apart from its dominant rival. The company is also loading Zune with a 50 percent larger screen than that of current iPods, as well as wireless capabilities that will allow users to send their favorite songs to other users with devices in close proximity.
Yet even as Microsoft gets ready to release Zune in time for the holiday season, Apple is grabbing attention with reports that the California company is about to offer downloadable movies that can be played on a new version of iPod with a bigger screen. Microsoft says that Zune will be compatible with any video formatted for an iPod or other media player. But the Redmond, Washington-based company is focusing on music, which it believes makes more sense on a device that people use jogging or riding their bikes. Still, even in the music space, Microsoft has its work cut out for it.
"This device, in my opinion, is make or break," says Seattle music author Charles Cross, whose books include a memoir of Jimi Hendrix. Like everyone else, Cross notes that iPod has captured 75 percent of the music-player market in the U.S. It has done so by forcefully laying claim to that elusive quality of cool -- not only offering the ability to digitally access music, but also a sleekness of design that has made it a fashion accessory.
There was a moment in the early '90s when Microsoft was cool, too. Software was king, and Microsoft was the king of software. But then the dot-com bubble burst and the company lost ground, and rivals like Apple began producing sexier products. Witness the reaction of Death Cab for Cutie bassist Nick Harmer regarding Microsoft's musical foray.
"I guess I'm a little skeptical," he says. A lot of that has to do with Windows, Microsoft's signature product. "It's clunky, aesthetically not interesting," Harmer says of the software. "It's the reason I switched from a PC to a Mac."
In its quest to catch up to the iPod, however, Microsoft has hired an army of musical savvy. Like Winn, many on the Zune team come from recording labels, radio stations or other music companies. They include Kyle "Kid Hops" Hopkins from Seattle's KEXP and Chris Stephenson, another British ex-pat who worked as an MTV vice-president in Europe and as marketing head for House of Blues, the L.A.-based chain of clubs and concert spaces, before founding his own consulting company. The visionary behind Zune, however, is a native Microsoftie, J. Allard, probably the one man at the company whose hipster credentials are unassailable.
Bearing a shaved head, an athletic build and a taste for the jackets of fashion designer Mark Ecko, the 37-year-old Allard came to Microsoft in 1991 after graduating from Boston University, where somewhere along the line "James" was reduced to simply "J." Allard's early claim to fame came soon after he arrived on the company's Redmond campus, during what was perhaps the first period in which Microsoft found itself lagging behind the technological curve. Other companies were starting to capitalize on the potential of the Internet, a platform that Microsoft seemed only dimly aware of at the time. Having come to Microsoft with what he says was the aim of getting his mom on the Internet, the then-24-year-old cranked out a twenty-page wake-up call of a memo. Originally sent to his direct supervisors, the memo made its way into the hands of Bill Gates. "It got around," Allard says.