Gig work and other flexible labour practices have been subject to unprecedented levels of attention recently. While this topic has attracted significant interest from employment lawyers, it remains relatively underexplored from other pertinent legal and inter-disciplinary angles. This paper will adopt an alternative perspective on flexible work inspired by Coase's theory of the firm. Focusing on the implications of flexible work for the relative allocation of control, risk and reward within the firm, it will highlight how both task-oriented (gig) and on-demand (casual) work practices typically entail workers assuming most of the positional disadvantages associated with orthodox employment and self-employment, while enjoying none or few of the corresponding advantages. Using a hypothetical contract analysis, it will highlight the structural similarity between flexible work and unsecured financial investments in business firms by reference to key strands of institutional economics and law and finance literature. On this basis, it will enquire as to optimal forms of compensation that rational flexible workers can (counter-factually) be regarded as bargaining for in the absence of impediments to efficient contracting, and as the price for trading off their traditional employment guarantees.