This article investigates marketers’ new media strategies targeting the millennial generation. Drawing upon in-depth interviews with industry professionals and an assortment of business discourses, I find that this consumer demographic is routinely conceptualized as "digital natives" who exhibit a "networked hypersociality" and a "participatory exhibitionism." A variety of innovative promotional tactics are being used to solicit self-expression and cultivate community within branded spaces and flows online. This development could reshape the advertising industry as commercialization further blurs with social and cultural content, obfuscating branding’s persuasive purpose from audiences. It also raises concerns about commercialization hijacking the political potential of an often-cited "empowering" new media environment as well as diminishing opportunity for youth identity to exist autonomous from the consumer marketplace at a time of escalating personal debt.