Demographic behavior and socioeconomic positions are inherited across generations, across both time and place. In this study we examine multigenerational dependencies in these dimensions over some 150 years in Sweden. We use a prospective approach where the eldest generation is the unit of analysis and the outcomes are lineage size and educational attainment in the youngest generation. Our data is a representative population of predominantly farmers born in the Skellefteå region in Northern Sweden in the 1860s and 1870s, and we follow these lineages until 2007. We follow our population during the fertility transition, industrial revolution, and educational expansion of tertiary education. Our results suggest that timing of birth, socio-economic position, and especially level of fertility are all central factors that explain the success of a lineage in terms of size, but also in terms of educational attainment. Later births allows the lineage to make use of social advancements and thus increase the proportion with tertiary education, higher fertility creates vast variation in lineage size, but also involves a quality-quantity trade-off of as the average level of education tend to decrease in subsequent generation. We also find prevailing effects of the eldest generation's occupation which are substantial in creating an educational advantage in the youngest generations. Importantly, these factors operate largely independently of each other in their association with reproductive and socio-economic success.