Stephen Westman is trying to negotiate with Out's photographer, David Roemer, to buy a particularly striking head shot of Pete Wentz, one in which, for a change, he looks like a grown-up. Wait, Roemer asks. What exactly do you do for Pete?
Westman shrugs, bright blue eyes sparkling. I'm his bitch.
It's true that Westman, 30, has no real title, but he's hardly anyone's bitch. He just doesn't know how to help his mom brag about his career. I look like a douche bag, he says, cringing. None of the shit fits.
Since January he's had only one real job: business partner in the growing empire of Pete Wentz. Westman runs Wentz's clothing and media company, Clandestine Industries; is working to steadily expand their chain of bars, Angels & Kings; and serves as general-assignment wrangler for any of the dozens of crazy ideas Wentz's hyperactive brain churns out.
In the office above Clandestine's flagship location -- a storefront straddling Chicago's punk-chic strip of clubs and Boystown -- Westman shows me the dry erase board where he tracks the text-message brainstorms Wentz sends at 4 A.M. until they either develop into full-blown projects or get scrubbed. During their first three years together Westman and his boyfriend had spent four nights apart -- until he started working for a rock star with grand ambitions.
Like Wentz, he grew up in the burbs (Park Ridge), played sports (baseball), and employed his considerable charisma to get away with being a bit of a freak. I was the Dennis Rodman with, like, fucking orange hair, he says. It was probably the result of me trying to express myself. I fully knew I was gay by junior high.
As lead singer of a band, Moda, he managed to attract enough attention to score a demo deal but not enough momentum to actually put out an album. So Moda threw in the towel. But if I wasn't going to be a musician, I at least wanted to be in that environment, Westman says. He would wind up as the first-ever vibe manager for the local Hard Rock Hotel, which encompassed every detail -- from which music videos were shown to the styling of the lobby.
When he opened a bar, the loungey, music-focused Lakeview Broadcasting Company, he turned a similar eye to branding minutiae. He approached Wentz for permission to dress his staff in Clandestine gear, which was sold strictly online at the time. Customers loved the look, and Westman soon opened a store stocking local designers' lines, including Wentz's, but within months it was Clandestine sales that were putting him in the black.
A deal struck with Crush Management (the company that handles all things Pete, as Crush head Bob McLynn puts it) made Clandestine and Westman 50-50 partners in the store and gave Clandestine exclusive use of its space. So a redesigned and relaunched store opened last October, with a stylist's chair installed in the back to offer a full menu of rock star haircuts and makeup instruction. (Next big idea: a full-fledged salon and tattoo parlor.)
Westman talks to Wentz, who according to both men is more of a collaborator than a boss, maybe a half dozen times a day -- staccato voice mails, one-line e-mails, and distracted conversations where they finish each other's sentences. In this world, I am very fortunate to be 'the gay guy,' Westman says. I bring such a different perspective creatively. I can be articulate yet animated, professional yet funny. I don't think straight guys get to do that. I can say 'Bro, I'm a homo' and go right into it. There are advantages.