Radically innovative information technology projects are considered one of the most challenging and difficult types of software projects to oversee and manage. The unique nature of such projects relegates them into a unique class of projects that we characterize as “Black Swans.” Highly innovative/radical IT projects reflect a “black swan” situation, where knowledge from previous projects do not provide significant insight into how they can be managed. While such “Black Swans” are a unique sub-set within the area of project management, understanding the techniques employed in the development and management of such efforts should enlighten and improve traditional project-management processes employed for most software development efforts. This paper presents and discusses key results of an exploratory field-study that examines eight unique “black swan” projects.