This chapter presents findings from a case study of the Turks and Caicos Islands (TCI) in the British West Indies area of the Caribbean. TCI is a tax haven that has worked to attract offshore financial firms such as trust, insurance, and financial management companies. All of these firms, which qualify as “information intensive,” are small in size (average 11 employees), engage in business on a global basis, and yet must compete while dealing with local infrastructure challenges. TCI is presented as the developmental context in which small businesses (largely owned or managed by foreigners from other cultures) must interpret and cope with national infrastructure challenges in this very small, young, rapidly growing island nation. Not surprisingly, we found that these firms share similar challenges with those in other developing countries; however, the perceptions of these challenges and how these small firms cope provide insights into the importance of small firms, small-scale foreign investment, and cross-national transfer of technology expectations.