The bookselling activity of P.I. Makushin is analyzed. His main enterprises in the field of book trade are listed: stationary - bookstores, kiosks, shops, non-stationary - delivered to the Tomsk province. His most successful projects were bookstores in Tomsk (the first specialized bookstore in Siberia) and in Irkutsk, which existed until nationalization in 1920. The obstacles to the development of book trade in Siberia in the late 19th - early 20th century were called and characterized. In general, they led to the failures of individual book trading projects of P.I. Makushin in particular, and the conditions for the successful functioning of his bookstores in Tomsk and Irkutsk. Among the reasons for the failures are the underdevelopment of transport infrastructure, the low level of literacy of the population, the predominance of traditional culture characteristic of the 19th century, a wary attitude to book trade by the authorities and difficulties in recruiting personnel. The authors propose to divide the success factors into objective and subjective. Among the first are the modernization changes of traditional society that took place in the late 19th - early 20th century, including the construction of the Trans-Siberian Railway, the increase in literacy of the population and the number of libraries, created conditions for the development of book trade in the region. Among the second - the personality of P.I. Makushin himself, who had entrepreneurial talent, indefatigable energy, dedication to his cause and many other qualities that allowed him to gain all-Russian fame as a book seller, publisher, enlightener and active public figure in one person. To expand the book market, the formation of new groups of readers, he carried out active work, the result of which was the construction of about 600 new libraries in the Tomsk province. In addition, he used the newest for his time achieving marketing and management. The dual role of the absence of zemstvos in Siberia in the development of book trade in the region is shown. The conclusion was made about the integrated approach of P.I. Makushin to the organization and development of his book trading enterprises.