This multiple-case study explored the nature of the experiences of family members of service-disabled veterans who participated in the Entrepreneurship Bootcamp for Veterans Family Program (EBV-F), an entrepreneurial learning and coaching program designed to assist family members of service-disabled veterans to support the discontinuous life transition of these veterans and their families. A blended-method, multiple-case study was used to explore the learning experiences and challenging life transitions of the EBV-F program participants. The study employed a new theoretical framework combining aspects of Mezirow's (1978a; 1978b) transformative learning theory and Schlossberg, Waters, & Goodman (1995) life transition theory. Semistructured interviews with 10 EBV-F family members, pre- and postresidency surveys were conducted, and a focus group was held. The primary, overriding finding of this study is that the participant's learning experience during the EBV-F program was transformative and improved participants' perceptions of self and their situations. Another important finding of this study indicated that the EBV-F program facilitation of the participants trying new roles and relationships was an essential part of their transformative learning experience. Possible implications of the study's findings include discovery of synergy between transformative learning and life transition outcomes. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]