This dissertation is oriented around understanding the implications of errors in cultural replication and transmission on larger patterns of technological change and the interaction between these errors and social and environmental processes. Grounded in the recent literature suggesting that small, past populations of humans were at an evolutionary disadvantage based on demography or low fidelity in social learning, this research focuses on how mistakes in cultural replication that are not entirely neutral might shift how we think about the relationship between group size and major themes such as cultural variation and complexity. Using computer simulation and the nearly neutral theory of molecular evolution, this research models the ways in which errors in cultural replication might impact the information or objects in which they accumulate and how in turn this might disrupt prevailing expectations of how much variation a group could come to contain, the diversity of variants possessed, relative levels of adaptation, and ultimately the potential for complex technologies. Using advanced fitness landscape theory, the first paper in this dissertation suggests that we think past prevalent models of optimization, selection, and innovation to consider a model of cultural evolution in which much variation was introduced randomly. The second paper suggests that the accumulation of error was not a limiting factor in the evolution of small groups, but rather that slightly deleterious errors are a critical form of variation in these small, evolving populations and further, when most errors are slightly deleterious (as the nearly neutral theory predicts) and variation is calculated over very long time spans, small populations may contain higher levels of variation than groups with significantly larger sizes. The third paper suggests that small past cultural groups may have been at an evolutionary advantage in some situations, such as when the environments they inhabited were spatially variable and population subdivision allowed intergroup communication. Finally, this dissertation suggests that in some cases intergroup exchange was just as important as minor acts of innovation and that under model conditions small groups appear no less likely than large ones to evolve complex technologies.