The bubbly 42-year-old British expatriate is a hard-core fanatic: 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 that the name of the tune on the B-side was "These Days." No wonder: Winn has spent his entire adult life in the music business, first making cups of 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 Japanese rock star Yoshiki.
On this breezy end-of-summer evening, though, Winn is here on behalf of his new employer, Microsoft. Winn is head of artistic development for Microsoft's new device, dubbed Zune. His sortie is to integrate the device with the music scene, in part by promoting emerging artists, so he has 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 current iPods, as well as wireless capabilities that will allow users to send their favorite songs to other users with devices in proximity.
Yet even as Microsoft gets ready to release Zune in time for the holidays, Apple is grabbing attention with reports that the California-based company is about to offer downloadable movies that can be played on a new version of iPod featuring a larger screen. Microsoft says Zune will be compatible with any video formatted for an iPod or other media player. But the company is concentrating on music, which it believes makes more sense on a device that people use while 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. Cross notes that iPod has captured 75 percent of the music-player market in the United States. It has done so by forcefully laying claim to that elusive quality of cool offering not only the ability to digitally access music but also a sleekness of design that has made the device a fashion accessory.
There was a moment in the early '90s when Microsoft was cool. 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.
In its quest to catch up to iPod, Microsoft has hired an army of musical-savvy folks. Like Winn, many players on the Zune team come from recording labels, radio stations, or other music companies. They include DJ Kyle "Kid Hops" Hopkins from KEXP-FM (operated by the University of Washington), and Chris Stephenson, another British expat 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 firm.
The visionary behind Zune, however, is a native Microsoftie: 37-year-old 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 jackets by edgy fashion designer Marc Ecko, Allard joined Microsoft in 1991, and somewhere along the line shortened his first name, James, to simply J (no period). Allard's early claim to fame came soon after he arrived on the company's Redmond campus, during perhaps the first period when Microsoft found itself lagging behind the technological curve. Other companies were beginning to capitalize on the potential of the Internet, a platform of which Microsoft seemed only dimly aware. 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 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. 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 boasting 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," Charles Cross says.
Now Allard is trying to transfer some of the lessons learned while creating Xbox to the music field.
Lesson 1: Know Your Customer. To create a mass product, Microsoft can't design products for the "Blue Badgers," as Microsofties call themselves (their ID 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, ones that would surprise and intrigue users.
"They were very, very interested in small bands," Tony Kiewel, Sub Pop's head of A&R, says of the Zune people. "They walked in the door really in love with one band and their record hadn't even come out yet." That band was CSS, a punk-influenced Brazilian group of four women and a man.
"We're just starting out. We want to be with those just starting out," Allard explains. "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 fact in his cubicle at Microsoft, where a huge poster for iPod hangs 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 accessories include a black studded 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. The iPod is ever-so-slightly lighter and sleeker than the Zune prototype, which is packaged in a similar box and features 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," Stephenson says, alluding to an online store, like iTunes, that will be connected to Zune. In the near future, Microsoft plans to add broadcasting functions that will allow Zune users to act as DJs, allowing random, nearby users of the device to tune in to what the DJs are playing, or letting the DJs specify their broadcasts for a group of users.
Zunesters, like all evangelical Microsofties, tend to get a little carried away when discussing their vision. Allard likes to say 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.