A study conducted by the CERT Program at Carnegie Mellon University’s Software Engineering Institute analyzed hundreds of insider cyber crimes across U.S. critical infrastructure sectors. Follow-up work involved detailed group modeling and analysis of 35 cases of insider theft of intellectual property. In the context of this paper, insider theft of intellectual property for business advantage includes incidents in which the insider’s primary goal is stealing confidential or proprietary information from the organization with the intent to use it to take to a new job, to get a new job, or to start a business. It does not include cases of in which insiders sell an organization’s information. This paper describes general observations about, and a preliminary system dynamics model of, this class of insider crime based on our empirical data. This work generates empirically based hypotheses for validation and a basis for identifying mititgative measures in future work.