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.
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. He's got a reputation as a driven competitor, but he also evinces puppydog playfulness. When the photographer at a promotional shoot asks him to do a foot motion for an artsy shot of his black-and-white Nikes, he doesn't hesitate. "I can do a toe curl," he volunteers. Minutes later, he's jumping off the stage.
Allard emerged from his sabbatical with a rather grandiose 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 video games. This was another case of Microsoft playing catch-up; Sony had by then cornered the video-game 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 Charles Cross.
Now, Allard is trying to transfer some of the lessons learned creating Xbox to the music field.
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 into 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, hopefully ones that would surprise and intrigue users.
"They were very, very interested in small bands," says Tony Kiewel, Sub Pop's head of A&R. "They walked in the door really in love with one band -- and their record hadn't even come out yet." That was CSS, a Brazilian group of four women and a man with a punk-influenced sound.
"We're just starting out. We want to be with those just starting out," explains Allard. "In some ways, we're the little guy. We're the independent label. Never mind that the company is ginormous. In the music space, we're nobody." He reminds himself of this with a giant poster for iPod that hangs in his cubicle at Microsoft, right beside a 1982 Time cover featuring Apple founder Steve Jobs.
"Look, I've got a Mac on my desk," says Zune marketing head Chris Stephenson, a trim 45-year-old whose fashion sense includes a studded black belt and sneakers, no socks. "It looks great. It looks fantastic. I've got a video iPod ready to go." He reaches into a drawer and pulls one out. It has to be said, the iPod is ever-so-slightly lighter and sleeker than the Zune prototype -- which is packaged in a similar box with a round navigational tool, a larger video screen and wi-fi hardware.
These wi-fi capabilities allow Zune to take a swing at what Stephenson says are "many, many chinks" in iPod's armor. In addition to its focus on new music, the Zune team is playing around with the notion of community, hyping something it calls "connected entertainment."
"It's about being online and sharing your favorite playlist -- at the school cafeteria and on the ski lift," says Stephenson, alluding to an online store, like iTunes, that will be connected to Zune. In the near future, Microsoft plans to add broadcasting functions, allowing Zune users to act as DJ, allowing random, nearby users of the device to tune in to what they are playing -- or specifying their broadcasts for a select group of users.
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 video game 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.
All of which gives Nick Harmer mixed feelings. "I don't know how much more enriching music could be," he says. "It's really just about listening along, snapping your fingers. Are they going to start packaging the thing with free drugs next?"
