This chapter covers the Vaglianos’ business during the first period of their activities, beginning as island shipping companies and ending as a prime international trading house in Southern Russia. The aim is to investigate the Vagliano’s activities in southern Russia, the Black Sea and the eastern Mediterranea, identifying the beginnings of their business. The maritime entrepreneurial environment in which they grew marked them, as all three Vaglianos started merchant captains, continuing Cephalonia’s maritime tradition. They were able to penetrate the established commercial and maritime networks of the Greeks from Chios and Epirus and form their own entrepreneurial networks in Russia, the Ottoman Empire, and Greece. They extended their business from the Azov to the entire Black Sea region, then into the eastern Mediterranean, the western Mediterranean, and even into northern Europe, by forming strategic entrepreneurial and societal alliances. The Vaglianos evolved from free traders combining trade and sea-transport into independent sailing shipping companies specializing in sea transport, forming large sailing ship fleets, and finally becoming international trading companies.