This exploratory study examines the relationship between cultural and creative entrepreneurs’ self-perceived creative and entrepreneurial competencies and their competitive and cooperative behaviour. The authors developed tailor-made survey scales and conducted a Prisoner’s Dilemma experiment with 45 cultural and creative entrepreneurs in the Netherlands. They found that both self-perceived absolute and relative creativity were associated with cooperation, yet in the reverse directions – that is, one’s self-perceived creative competencies positively related to cooperation, while self-perceived creative skills relative to other people’s creativity negatively affected cooperative behaviour. The former may suggest a sense of self-confidence that leads to a propensity to seek collaboration, while the latter may indicate a sense of superiority that eradicates any need or inclination to cooperate; self-perceived entrepreneurial competencies do not matter.