Today small businesses, public schools, local governments, universities, international conglomerates, and nonprofit agencies all feel the pressure to have informative and interactive presences on the Web. This new Web-based information economy has helped to significantly narrow the gap between the technical writing needs of profit and nonprofit workplaces. As local, regional, national, and international groups now compete for attention, business, and participation in the vast arena of the Internet, academic and workplace writers must develop theoretical and practical strategies for identifying and accommodating the varied needs of multiple organizations and audiences. Our technical writing students need to be cross-trained to face profit and nonprofit writing challenges, and our contact people in the community need to be aware of the benefits they can realize through working with students on major projects. In this chapter, I will offer some suggestions for making this collaboration work.