Using a Logistic regression model the present study investigates the important factors that influence on ease of doing business by the women entrepreneurs. The respondents are from the four different backward regions in West Bengal, India. The goodness of fit of the model is checked in terms of the Hosmer–Lemeshow test. Moreover, a large share of the women-owned business is a single person enterprise, generates lower revenues, and is smaller in size. The study shows that most women are engaged in small entrepreneurs to help their families financially. Though, women entrepreneurs are facing challenges of financing and non-cooperation from their family members. Even from non-cooperation from the family, they are engaged in entrepreneurship after managing their households’ work. The level of productivity will be enhanced significantly in case easy access to credit and support received from the family members. The support may be in terms of mental as well by helping in households’ work. Further, the application of the Welch’s t-test shows the non-existence of a significant difference in income level among the two groups, who have faced complexities and who have no complexities into running the entrepreneurship. To improve the socio-economic status of the female counterpart of the society, initiatives from the grassroots level are absolutely essential.