This chapter uses the case of students enrolled in the Multimedia Pathway offered by Harbourside High School to discuss the tensions and contradictions inherent in the views that: (a) school curriculum and pedagogy have much to learn from young people's informal and leisure-based learning; and (b) school-based courses in new media are important because they increase student retention and the chance of success in post-school employment. We draw on literature about the "new work order" (Gee, Hull, & Lankshear, 1996) to explore the nature of these students' learning about and with ICTs and show that the students' knowledge exists "in a network of relationships" (Gee, 2000) that bridge the formal and informal learning divide. Finally, we discuss the parts played by their in- and out-of-school engagements with ICT in their becoming the kinds of portfolio people supposedly required by the new capitalism.