This study develops a theoretically based examination of the relationship between evaluation and entrepreneurial opportunity using data collected from entrepreneurs operating businesses in the “Second Life” (SL) online world. The basis for this study is founded on the opportunity perspective developed by Shane and Venkataraman (2000) whereby the actions undertaken by an entrepreneur can be categorized into three processes - discovery, evaluation and exploitation. Review of the extant literature reveals that evaluation is often overlooked, or is unmeritoriously blended with the elements of discovery or exploitation (Davidsson, 2004). Hindle (2007) argues that the skill of evaluation is the core entrepreneurial skill and that it deserves greater recognition by researchers. The purpose of this study is to explore these notions further and provide insight on how entrepreneurs envisage what to do with a productive opportunity through the evaluation process.