A review of the extensive separate literatures on salesmanship and entrepreneurship highlights interesting similarities between the two professions, but there is a lack of studies examining these similarities or explaining the differences. In particular, why do salespeople struggle with image and trust issues and yet society tends to respect and admire entrepreneurs, even though both have something to sell?  The author refers to this phenomenon as ‘the salesmanship / entrepreneurship dynamic’.\ud
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A conceptual framework is developed synthesizing the literature and identifying seven elements of the salesmanship / entrepreneurship dynamic: vocational image; cultural and professional background; assertiveness; control preferences; humanity; characteristics and traits; adaptability.  The objective of this thesis is to contribute knowledge in two ways:\ud
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Contribute new perspectives within the seemingly unexplored genre of the salesmanship / entrepreneurship dynamic, and\ud
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Expand upon existing knowledge related to selling and entrepreneurship.\ud
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Within the realism paradigm, semi-structured interviews were conducted with 10 highly successful sales people and 11 highly successful entrepreneurs. The research provides a direct comparison, asking the same questions of both groups. This approach has not been reported previously within the literature. Analysis of the findings identifies key behavioral issues, such as those related to work ethic, integrity and humility, which may contribute to the positive and trustworthy image of entrepreneurs, even though many are selling and also contribute to the untrustworthy image of salespeople, even though many are entrepreneurial.\ud
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Despite the crossover between these vocations, the variances identified between the groups appear to be connected to their different perspectives in relation to their respective businesses. The entrepreneurs’ motivation seemed to be closely connected to the wider success of their businesses. In contrast, the salespeople displayed narrower perspectives related to their own self-interest. This difference manifests itself in behaviours that are more likely to engender trust for entrepreneurs.\ud
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Recommendations are made for teaching, practice and further research relating to these findings