Network entrepreneurs broker relationships as opportunity exploitation. These entrepreneurs rely on mechanisms for building trust. Although entrepreneurship scholars have learned a great deal about trust, much of that work is bounded in contexts that provide important tailwinds for the willingness to be vulnerable. In contrast, we conducted a qualitative study of trust (and trust repair) by network entrepreneurs in a gray market—a context between the poles of legal/legitimate/appropriate and illegal/illegitimate/inappropriate. Our theorizing uncovered network, heuristic, trustworthiness, and control sources of trust (and trust-repair efforts) that sometimes differ from dynamics seen in traditional and criminal ventures.