The purpose of this phenomenological study was to understand and describe the lived experiences of adult learners who are owners and managers of small winery businesses operating in the start-up phase of the organizational life cycle. The study explored and identified the meaning of adult learning in the entrepreneurial context and its affect on the performance of the small wineries. The relationship between adult learning was investigated through the lens of adult learning, transformational learning, and entrepreneurial learning theories as well as the organizational life cycle theories. A phenomenological approach was used to gather descriptions about the meaning of the adult learning experiences of fourteen participants. The selection criteria for participants included entrepreneurial individuals who represented owners and managers of small local boutique wineries which were operating in the start-up phase. The wineries were similar in size and located in the same geographic area. Data analysis was conducted following Moustakas (1994) method. The culminating attributes that emerged from the data analysis identified themes demonstrating the significance of the connections between entrepreneurial relationships developed, challenges confronted, and the joy and satisfaction experienced through learning by participants. It was the perfect pairing between adult learners and boutique wineries operating in the start-up phase. [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.]