The history of family run business in Surat, India is more than 350 years now. However, over the last several decades, it has been observed that family run enterprises in Surat have not been able to scale up the business by untapping opportunities in international markets. The paper aims to explore the experiences of family-run enterprise owners in their attempt to grow their businesses in Surat. Given the stagnant growth trajectory, less expansion, and minimal diversification over the last several decades, the researcher is intrigued to study the experiences of these family-run enterprise owners. As a phenomenological research study, there is only one question: What experiences have these enterprise owners faced in a family-run enterprise as they attempt to grow their businesses? Non-leading prompts were asked to encourage participants to expand their responses to lead to a deeper understanding of those experiences. As respondents, seventeen family-run enterprise owners have been contacted for In-Depth Interview (IDI). The respondents were from diamond, textile and restaurant business in Surat. The study aided in identifying existing challenges and strengths making the whole experience of family-run enterprise owners unique, diverse and different from the conventional businesses operating in different industry. The findings indicate that the potential of family-run enterprises have not been harnessed to its fullest due to prevailing mediocrities, sub-standard practice, sophisticated and disoriented business procedures and system. Organization Development (OD) interventions would be effective in unearthing deeper issues and problems amongst these family-run enterprises in Surat.