“Intrapreneurship” is the accepted name for entrepreneurship conducted inside an established business or organization. Choices involving innovation within the corporate enterprise inevitably include a higher degree of risk and uncertainty than decisions about routine operations. Teaching intrapreneurship itself is a challenge because of the wide variety of possible settings and fact situations. Presented here are three short cases, each less than a page, highlighting the challenge of entrepreneurial decision-making for the nontraditional entrepreneur. These scenarios involve a nonprofit trade association, a Federal government contractor, and a small private college. Each micro case is taken from an actual enterprise operating in the greater Washington, DC region, around the nation’s capital. Names and, in some cases, descriptions of the business have been altered to preserve anonymity. The first case presents challenges faced by a trade association as it evaluates new business opportunities and judges the market potential of new and untried product offerings. In the next case, a Federal government contractor must carefully weigh decisions about technology and purely business considerations. In the final scenario, a pair of alumnae entrepreneurs proposes a for-profit business partnership with a nonprofit school. The university president must consider venturing into money-making activities while his board of directors has serious doubts. These micro cases highlight the challenges and potential associated with bringing creativity and innovative thinking to established organizations in the process of intrapreneurship.