This study explored connections between adult learners and their experiences in the context of small boutique wineries operating in the start-up phase of the organizational life cycle. The research objective was to gain insight regarding the pairing of adult learners with the entering of a specialty industry. Fourteen individuals from four wineries were interviewed in the workplace. Six themes emerged from the adult learning in the specific context the boutique wine industry: (1) Developing an Entrepreneurial Sense, (2) Relationships, (3) Challenges, (4) Learning, (5) Joy or Enjoyment, and (6) Reflection.