The article discusses the development of trade and entrepreneurship in the period of emerging market relations in 1992-1995 on the example of Tomsk Oblast. The aim of the article is to characterize the behavior of entrepreneurs in a transitional economy and the building of relationships between trade and food industry. To explore this issue, periodical materials of Tomsk Oblast, regulatory and legislative acts of the period were used. Using methods of historical research (systems analysis, the historical-genetic method), a number of conclusions about entrepreneurs' adaptation to the conditions of a market economy were made. This study provides examples of how businesses and trade responded to changes in the economy and highlights the adaptation mechanisms of food processing enterprises that were applied in other industries. In 1992-1995, entrepreneurs took advantage of opportunities that gave quick results, but were not suitable for the long term. This is justified by the fact that the emerging unstable economic situation and the formation of the legal framework required quick reactions from economic entities. The practice of opening branded outlets was widely used, excluding retail stores from the chain. The example of Tomsk Oblast shows the non-payment crisis of the first half of the 1990s, and the practice of overcoming it by Tomsk entrepreneurs. Among the trade enterprises in Tomsk, small ones prevailed, with up to 15 employees. The formation of the legal field lagged behind the rapidly developing economic relations, which entrepreneurs used for personal gain, for example, to fix prices, choose liquid product for sale. By the mid-1990s, basic retail norms had been formed; they were often neglected, leading to trade in substandard goods. At the first stage of the formation of market relations, it was not possible to build strong ties for trading entrepreneurs sought to obtain quick profits, used practices of integration into economic relations that were ineffective in the long term, and neglected the rules and requirements for trading activities. Based on this study, it can be concluded that the mechanisms and practices, relevant for Tomsk Oblast, that trading entrepreneurs used were in demand in other regions of the country since federal regulations formed a single legal framework for the development of economic relations.