Stiles Anderson and Glen Schwartz faced one major hurdle when they decided to start their own denim company: neither of them knew anything about making jeans. “Looking back, people must have thought I was an idiot,” Anderson says. “But sometimes being an idiot is a good thing. You don’t have to admit that you’re stupid–you just have to keep asking questions.”
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Schwartz and Anderson, neighbors in a Lincoln Park apartment building, met in the fall of 2004. Schwartz, 32, was an environmental cleanup consultant and something of an entrepreneur, running a real estate business on the side. Not long after getting to know Anderson, a financial analyst, he casually suggested that they go into business designing and selling T-shirts. Anderson, 25, wasn’t crazy about the idea, but it did get him thinking and he suggested trying to create the perfect-fitting pair of jeans, something he says he’s had an “obsession” with finding since high school. “I want something that fits my body and looks good,” he says. “I have thighs and an ass–I’m not a skinny European guy. There weren’t any pairs in the premium world that fit me properly, and Glen felt the same way.”
The next several months were spent fine-tuning the concept through focus groups and online surveys. They spent thousands of dollars on different jeans, inspecting every last detail, while Anderson pored over textbooks on garment construction and pattern making. “Not to be artsy-fartsy, but it is an art,” Anderson says. “Businesspeople don’t think that way. I had to train myself to think like a designer.” There were numerous tiny decisions that had to be made, from pocket size and placement to the color of the thread (Schwartz jokes that it took Anderson a year to settle on one). “In a month and a half I taught myself Illustrator and Photoshop, because everyone needed the images in an electronic format,” Anderson says. “We had to learn not only how to construct the jeans and development, but also the finishing work, how you sell it, how you show it. It was endless hours of analyzing and reevaluation.”