The history of the Galaxy is captured in the population of dead stars in the Galaxy. A particularly interesting population are the ultra-compact binaries (UCB) which emit detectable gravitational waves (GW); 95% of this population is comprised by doubly degenerate white dwarf binaries, which are good sources for LISA. We use the population synthesis code COSMIC to simulate the lives of UCBs. We evaluate the stellar evolutionary history of each binary to discern how the end state properties of a given binary are connected to its initial state and the ensuing evolutionary history. We find binaries evolve through parameter space together, so groupings in the LISA catalog of observed binaries are tracers for stellar evolution. In this paper, we illustrate how the evolution history and ZAMS properties of binary systems would affect the properties of the stellar population in the galaxy today that can be observed by LISA.