Czech family businesses are currently experiencing their first changeover of generations in history. Either the first generation (founders or successors) or two or more generations collectively operate in management and administrative authorities. The purpose of this article is to compare and evaluate preference for the use of debt or equity financing in family businesses with the differing involvement of generations and the diversity of its allocation for the specific need of growing the company. This empirical study was performed on the basis of a qualitative analysis of 245 family businesses. Hypotheses were confirmed using the Pearson correlation coefficient. This study confirms the dependence of the use of equity and debt financing on the number of generations in management. This brings differing perspectives, opinions, and practices for financial management in the sense of a preference for the use of debt or equity financing. The need for debt arises at the moment of compensating the transfer of ownership between generations. The results of the analysis indicate that family businesses managed by one generation prefer equity financing, companies managed by first and second generations prefer debt financing, and companies managed by second and third generations prefer equity financing.