The bubbly 42-year-old British expatriate is such 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 recording studio in Birmingham, England, 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, Winn is in Seattle on behalf of Microsoft, his new employer, which has headquarters in Redmond, just outside Seattle. The head of artistic development, Winn is part of the team producing Zune, Microsoft's answer to Apple's iPod. His task 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 screen that is 50 percent larger 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 company is focusing on music -- which makes more sense, it believes, for a device that people use while jogging or riding their bikes. Still, even with music, 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 -- offering consumers not only digital access to music, but a sleekness of design that has made it a fashion accessory.
In its effort to catch up with the iPod, Microsoft has hired an army of specialists with 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-FM and Chris Stephenson, another British ex-pat who worked as an MTV vice president in Europe and as marketing head of 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.
With his shaved head, athletic build, and taste for jackets by fashion designer Mark Ecko, Allard came to Microsoft in 1991 after graduating from Boston University, where somewhere along the line his first name was reduced simply to "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 20-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.
Plugging away on the internet for seven more years, Allard longed for a change. He took three months off and bought himself a bunch of techie toys, including a Sony PlayStation and a portable music player. It's easy to picture Allard happily messing around with his toys.
During his sabbatical, Allard experienced an epiphany: "Technology was going to change entertainment forever." Returning to Microsoft, he looked around for a platform to prove his point and eventually settled on videogames. This was another case of Microsoft playing catch-up; Sony had by then cornered the videogame market. But Allard went in fighting and came out with Xbox, a system with state-of-the-art graphics, imaginative games, and a wildly enthusiastic fan base.
"It finally was a device that was cool that had Microsoft's name on it," says music writer Cross.
Now, Allard is trying to transfer to the music field some of the lessons learned creating Xbox.
Lesson 1: Know Your Customer. To create a product with mass appeal, Microsoft can't design for the "blue badgers," as Microsofties call themselves (their identity passes are blue). So Allard has an unusual recurring event scheduled in his calendar. "Once a month," he says, "I go to Target. I get a corn dog, walk the aisles, and listen to customers."
Lesson 2: Always Think About the Artist. This is a subversive concept at Microsoft, which has always thumbed its nose at so-called content providers. But Allard insists that content, not software, is now king. And he says it has to be "tomorrow's content, not yesterday's content."
To this end, one of the first calls the Zune team made was to Seattle's Sub Pop Records, where Microsoft explained its intention to preload the device with 25 music and video selections -- choices, the company hopes, that will surprise and intrigue users.
"In some ways, we're the little guy," says Allard. "We're the independent label. Never mind that the company is ginormous. In the music space, we're nobody."
Zunesters, like all evangelical Microsofties, tend to get a little carried away when discussing their vision. Allard likes to say that he thinks of iPod as "the Pong of digital music," referring to the elemental videogame from the '70s. He spins tales about the way an intelligent Zune service will someday be able to record everything about every concert, album, and music video. Want to remember the playlist at a Kanye West concert after you get home? Want to know what he had for lunch that day? Want to hear him expand upon what was going through his head as he recorded a song? Then tap into Zune.