This study for the first time addresses generation effects on eight entrepreneur types across four U.S. generations: Traditionalists, Boomers, Gen‐Xers, and Millennials. It adopts hierarchical age‐period‐cohort (HAPC) models using multilevel mixed‐effects logistic regression models with random period effect controls and the same‐age comparison between two neighboring generations. The empirical study relies on monthly Current Population Survey data across 11 years (2006–2016). When controlling for age, period, path dependency, seasonality, and other demographic and socioeconomic factors, no generational differences are identified for workers' entrepreneur propensity, mirroring entrepreneurs' misfits; for entrepreneur‐type propensities, limited generation differences are identified: the odds for Gen‐Xers to be novice (vs. non‐novice) entrepreneurs are 10% higher than Boomers for the ages of 44 and 51; the odds for Boomers to be opportunity (vs. necessity) entrepreneurs are 2.3 times higher than Traditionalists for the ages 63–70. The limited generational difference is consistent with prior literature using HAPC.