We give a bijective correspondence between the number of nilpotent matrices over a Boolean semiring and the number of directed acyclic graphs on ordered vertices. We then enumerate pairs of maps between two finite sets whose composites are eventually constant by forming a bijection that relates a pair of such maps with a spanning tree in a complete bipartite graph, and an edge of said tree. This generalizes the main principle of A. Joyal's proof of Cayley's formula. Finally, we generalize T. Leinster's work by considering a pair of finite-dimensional vector spaces and show a bijectivity between a nilpotent pair of maps and a balanced vector with the hom spaces between them. This leads us to an elegant formula for the number of nilpotent pairs.