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We explore the theoretical foundations on how firm and IT characteristics explain the market value variations in e-commerce initiatives by examining the announcements of 946 e-commerce initiatives in the public media. Our approach combines the Event study methodology and Decision tree induction to examine the main and interaction effects of IT and firm characteristics on Cumulative Abnormal Returns (CAR). In particular, we generate complex interaction models that can guide e-commerce investment decisions so managers can know, for example, which combination of IT and firm characteristics are more likely to be viewed positively by investors. The selected study variables as well as explanation of the proposed framework are informed by innovation, resource-based view, transaction cost economics and complementarity theories. We have inductively developed a set of propositions that can be …