The nineteenth century introduced significant changes in the socio-economic and cultural development of Russia including the position of Russian women, especially among the business-oriented city dwellers. Their widows and unmarried daughters retained a privileged status for the rest of their lives, however, to run the business, they had to pay the guild fee – a significant amount to the city budget annually. The basis for the widows’, their children’s and household members’ well-being was their financial and business expertise. Their active participation in the city’s economic and social life manifested a preliminary meritocracy principle, in contrast to the life-long privileges of other social groups. Unlike their late husbands – widowed business matriarchs could not count on the support of their spouses in either business, housekeeping or family matters. Yet there were examples of successful businesses run by women. While the history of women’s entrepreneurship in Moscow and St Petersburg has received coverage, the fate of these matriarchs in Ural region has not yet attracted scholars’ attention. This pilot study focuses on the demographic characteristics of the Yekaterinburg businesswomen-matriarchs. Since the group is not big, and the potential for comparative study is limited, the authors rather focus on how the demographic data can be used in reconstructing the first businesswomen’s life courses. They use data from the nineteenth century Revizskie Skazki for Yekaterinburg, the latest of which, 1858, has been transcribed into the electronic resource Ural Population Project (URAPP). The article presents arguments supporting the hypotheses that kuptsy (businesspeople) were the first to develop new demographic behaviour (nuclear family pattern). Most Yekaterinburg kupets girls married after reaching 20 years old; only 8 % of kupets females aged 40–49 remained maidens. Husbands were on average 6 years older than their spouses, which increased the likelihood of early widowhood. The number of widows increased steadily, and by the age of 40 almost every second kupets woman was a widow and at age 50 more than 75 %. There were three main life trajectories for the widows depending on the age at widowhood, and the age and gender of their children. The authors focus on the life courses of those who did not remarry. The share of kupets families headed by women in 1858 Yekaterinburg was 16 %. Some of them joined the business while still married; others took over responsibility after their spouses’ passing. Some business matriarchs kept their power over large families that included adult married sons. This could be due to financial circumstances, family arrangements, and the personal characteristics of domineering mothers. The research also reveals cases when three kupets widows composed a common households and ran successful business for decades.