Entrepreneurs are often critically dependent on their stakeholders. An important challenge for entrepreneurs is to convince and involve key stakeholders so that they see themselves as part of a collective effort towards realizing a novel value proposition, that is, they adopt a We-framing of the collaboration. We argue that stakeholders are stratified in terms of their importance to the entrepreneurial venture and how much interaction is required between the entrepreneur and the relevant stakeholders. Awareness about collaboration goals as well as collaboration frictions is particularly important for relations that involve the key stakeholders. This involves incorporating the knowledge representations of the key relevant stakeholders to formulate mutual collaboration goals, but also includes devising ways to anticipate and reduce potential frictions to the collaboration, particularly when adaptation is required. To better understand this challenge, we draw on recent cognitive science literature, theorizing a social metacognition perspective on stakeholder enrollment. We conceptualize joint metacognition as a way through which entrepreneurs and their key stakeholders jointly reach greater understanding in their process of enrollment, and describe how perceived goals, knowledge, and beliefs of others are adjusted to what is best for the collaboration, and how debiasing may assist this process. Lastly, we discuss two distinct forms of metacognition which leads entrepreneurs and key stakeholders to consider their collaboration goals and overcome cognitive frictions.