The article examines the activities of one of the largest steamship and transport enterprises of the Volga-Kama basin in the early 20^th century — trading house “F. and G. brothers Kamensky”. The company had a long history, having existed for more than half a century, transporting goods and passengers along the Volga and Kame, as well as by horse-drawn and railroad transport. Founded by the efforts of Fedor and Grigory Kozmich Kamensky in 1857, the company experienced success and setbacks that led to its absorption by another more successful enterprise in the early 20^th century. The article pays special attention to the reason for the commercial failures of the children and grandchildren of the founders of the company, who came to its management after the death of Fеdor and Grigory Kamensky. In the face of heightened competition at the beginning of the 20^th century between various shipping and transport companies, especially after the economic crisis and the revolutionary events of 1905–1907, the Kamensky family made considerable efforts to save their enterprise, spending significant funds on its modernization. The company grew the network of its offices significantly not only in the vast territory of Russia, but also beyond its borders. New steamships were purchased, the orders of which were located at domestic factories. Having opened its offices in Hamburg, Berlin and London, the company tried to get involved in the export trade of Russia, planning to use its vehicles. However, poor management practices and disproportionate spending on expanding the enterprise infrastructure and its technical equipment brought the company to the brink of bankruptcy.