In fields like Human-Computer Interaction designing for safety often focuses on mitigating interpersonal harms such as online harassment. While essential, this emphasis may overlook the psychological aspects of safety, including trust. These aspects are especially important in marginalized contexts. This study explores the factors that foster psychological safety among financially-constrained aspiring entrepreneurs. Using a case-study approach, we analyzed data (10 interviews, 3 focus groups) from 21 financially-constrained aspiring entrepreneurs who engaged with a community-based sociotechnical platform. We identified four key factors that shaped participants’ sense of psychological safety: shared identity, interpersonal trust, perceived expertise, and shared accountability. These insights inform design strategies emphasizing shared accountability and leveraging collective identities to empower users in underserved communities. While centered on financially-constrained entrepreneurs, these strategies offer broader applications and should be considered when creating online spaces that promote connection, collaboration, and psychological safety across diverse contexts.