Purpose The purpose of this paper is to look at the role played by three archetypal constructs pertaining to the individual sustainability-oriented entrepreneur, namely prior knowledge, sustainability orientation and sustainability intention, in legitimation behavior and explores their strategic utility.Design/methodology/approach The author studies legitimacy-seeking behavior in the case of ten sustainability-oriented entrepreneurs. A qualitative case study approach is used, capturing evidence of legitimation behavior in the startup phase through interviews, participant observation and documentation analysis.Findings Prior knowledge and sustainability orientation appear to offer little value beyond their role as necessary factors in maintaining legitimacy. Both appear to have limited strategic value for legitimation in comparison to sustainability intention. Intention as a construct embodies the paradox of sustainability-oriented entrepreneurship, and learning to successfully overcome this paradox to strategically utilize intention in legitimation is crucial for these entrepreneurs.Practical implications Knowledge of these factors could assist sustainability-oriented entrepreneurs in strategically utilizing these factors as agency when dealing with diverse stakeholder expectations to achieve their enterprising goals. Strengthening knowledge on factors important for legitimacy is pertinent in supporting this shared value approach to entrepreneurship.Originality/value Little theoretical or empirical attention has been paid to the complexity of strategic legitimation behavior of sustainability-oriented entrepreneurs. This paper provides novel empirical insight into what role these archetypal factors play in legitimation behavior and how they can be strategically utilized.