We develop and empirically test why, when, and how entrepreneurs choose to rapidly re-engage in firm creation after business closure. We draw on the notions of human capital, knowledge spillovers, and business cycles to build a comprehensive framework aimed at better understanding the choice of accelerated repeat entrepreneurship. The tests performed using data from multiple countries and several periods consistently reveal that after business termination, the likelihood of rapidly re-engaging in entrepreneurship is positively influenced by the experiential capital of entrepreneurs (i.e., skills developed from launching new businesses and innovative products in previous organizations). Furthermore, this positive relationship is clearly heightened by favorable business cycle and spatial context conditions. Results are expected to shed some light on the circumstances under which repeat entrepreneurship rapidly occurs before second opportunities vanish. A timely action by policy makers is recommended to promote repeat entrepreneurship.