The aim of this paper is to inform a sociological jurisprudence of the implied duty in the contract of employment of mutual trust and confidence. Present analyses of the emerging term have been doctrinal in nature. Such scholarship contributes a normative internal perspective to what can be understood as the jurisprudential project of guarding and maintaining law as a practice of regulation. This paper seeks to generate knowledge that will allow for an extension of the jurisprudential analysis to take into account how mutual trust and confidence may manifest in contemporary conditions of work. This is achieved by, first, presenting original sociological data of the employment relation in a work context likely to demonstrate practices that resonate with features of mutual trust and confidence – that of early-stage digital technology startups – and, secondly, contrasting this empirical account with doctrinal conceptions of the term. Findings unsettle the dominant jurisprudential account of mutual trust and confidence as positively contributing to the social goal of labour law as operating to counter the power of capital.