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This article analyzes tramp shipping firms and attempts to provide an insight into its organization, structure and entrepreneurial methods through a comparative perspective, to identify continuity and change that will enhance the understanding of the successful path of British and Greek tramp operators over a similar and different periods of time. The tramp shipping firm lies in the middle of three interactive networks: the regional, the national and the international. Tramp shipping companies, international by their nature, share many characteristics with international trading companies. Knowledge, information and human relationships often proved the ownership advantages of service sector firms. In endeavoring to present a typology of the tramp shipping company, we can distinguish two periods, pre-World War II and post-World War II. In the first half of the twentieth century, the tramp shipping operators fell into two categories: the cross-traders, like the Greeks, and the national traders, like the British. In the second half of the twentieth century, tramp shipping was transformed in response to the need to adapt to the changes dictated by international trade. It is evident that the organization, structure and entrepreneurial methods of British and Greek tramp shipping have followed a similar paths and have shared common characteristics that have contributed to their success for a large part of the period from mid-nineteenth century to the present day.