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Drawing on a qualitative sociology of Saint Petersburg club entrepreneurs in the 1990-2010s, the article interprets ambivalences and uncertainties observed in the professional representations of these actors, through evolutionary reconfigurations of the post-Soviet clubbing market. This interpretation reveals several compositions and compromises between different “orders of worth” (Boltanski & Thévenot, 1991), their mutual redefinition and transformation, as well as tensions between the “worth of inspiration (Art and Culture) and the practical logic of market viability. The latter doesn’t form any “worth” but contributes to undermining these entrepreneurs’ capacity to find a legitimate qualification of their action. The grand dichotomy between “Art” and “Business” arises through the relationships that exist between club entrepreneurs and their investors; this is also analyzed through an international partnership aiming to implement the “creative industries” model in the region of Saint Petersburg (2002-2003). In the second half of the 2000s, under the impetus given by new actors and new types of venues emerging on the market, original compromises were established between several “worths,” themselves redefined and updated, providing this entrepreneurship with flexible and plural forms of justification. For instance, a form of compromise has been found between a renewed “worth of inspiration” and “market worth,” through the representation of regular customers, which would be solvent and, at the same time, “culturally valid” (“creative intelligentsia”).