The current article scrutinises the capital/labour (or production/appropriation) contradiction within a capitalist society under a neoliberal frame. Here, it is applied to small companies, which are the locus of all entrepreneurship. Current capitalism regards entrepreneurship in such a privileged guise that it has been fostered widely, mostly from the 1990s. Even in times of crisis, such as the one which has been around since the 1970s, it has escalated. Highlighting the chances for autonomy and self-sufficiency, those advocating entrepreneurship are successful in leading the worker into believing he could be capital’s partner. However, since it is not ontologically feasible that different economic systems coexist unrelated and in harmony, we question the real motives behind promoting small business in times of capital concentration and pooling. While recognising the capitalist frame behind Fordist relations, we insist that workers’ exploitation intensified throughout the Toyotist period, eased by the restructuring of capital, whose policies render the market much more aggressive. Against such background, we argue that entrepreneurship, instead of granting any freedom whatsoever, enslaves, since capital seizes all the entrepreneur’s time. In the current historical moment, this relationship, which we regard as one of the main means through which the capitalist contradiction moves, forces the workers into a direct confrontation with the market, thus erasing any social protection in place and the possibility of class struggles, since we are dealing with a ‘subject devoid of subjectivity’. After looking at the objective conditions under which the entrepreneur is anchored into the economy, we conclude that the market is the worst boss.