Kottke attended Coe College on scholarship in Iowa and eventually began a career in design. In 1999, he designed the Silkscreen typeface—since used by Adobe, MTV, and Volvo among others. His design work has been featured in The New Yorker, The New York Times, Forbes, and Brill's Content. Kottke created the iconic Gawker logo in 2002 in what he claims was "whipped up in Photoshop in 30 minutes as a placeholder".