This paper examines the mechanisms by which regional culture influences entrepreneurs’ decisions to start software companies in three Canadian cities: Waterloo, Ottawa, and Calgary. It is hypothesized that regional cultural contexts and expectations will be a significant influence in explaining both why and how entrepreneurs start and build their firms. This work contributes to an increasing interest among entrepreneurship researchers about the role of regional contexts and cultures on the entrepreneurship process. This paper build on existing Bourdieuian approaches to entrepreneurship by placing them within a geographic framework. A regional Bourdieuian approach provides better tools for both researchers and policy makers to understand the complex interdependencies between regional cultures, contexts, and entrepreneurship.