For entrepreneurs and senior-level employees in Trinidad and Tobago’s small and medium-sized enterprises (SMEs), achieving export readiness is a significant milestone. The Trinidad and Tobago Chamber of Commerce (TT Chamber) has long emphasized this goal through its Contact Magazine and various initiatives, offering incentives, support services, and financing options to help businesses scale from micro to large enterprises. Both public and private sectors have introduced technical and operational growth programs, including the TT Chamber’s inaugural SME Conference, ‘Catalyst,’ aimed at fostering SME development. However, while some SMEs have achieved remarkable regional and international success, many still struggle to break through. This raises critical questions about policy environments, financing accessibility, and the effectiveness of public and private support systems. Marc Sandy, Manager of the Trade & Business Development Unit at the TT Chamber, highlights that while these factors are important, the entrepreneur’s passion and commitment to building a sustainable brand are paramount. One standout example is Farm and Function, a local agro-processing company that has expanded its regional footprint despite challenges, including the COVID-19 pandemic. Founded by David Thomas and Rachel Renie-Gonsalves, the company evolved from d’Market Movers, an online fresh produce distributor, into a leading supplier of frozen fruits. Farm and Function’s success story underscores the importance of resilience, strategic pivoting, and a clear vision. As SMEs navigate the complexities of export readiness, they must ask themselves fundamental questions about their ambitions, adaptability, and discipline. The journey from local to legendary demands not only financial and operational readiness but also an unwavering commitment to a global vision.