It is widely acknowledged that there is a high failure rate of entrepreneurship across the world． Although entrepreneurial failure brings emotional and financial costs for entrepreneurs，such experiences also provide them with unique entrepreneurial learning opportunities． Thus，a key factor to reduce social costs of entrepreneurship is to activate venture losers’passion of persisting in their entrepreneurial endeavor． Using 306 020 samples selected from three panel databases including GEM，the World Bank and the Gelfand，the current study investigates the impact of entrepreneurs’prior entrepreneurial failure experience on the choice of entrepreneurship across different countries with different cultural and institutional environments． It is found that compared with entrepreneurs without failure experiences，entrepreneurs with prior entrepreneurial failure experiences are more likely to start entrepreneurship again． Such relationship is further amplified in countries with a looser culture and superior institutional environment． A three-way interaction among gender，culture and prior entrepreneurial failure is identified，which implies female entrepreneurs are more likely to restart entrepreneurship in countries with a looser culture． Our study embedded gender differences into entrepreneurial failure analysis，thereby extending prior studies from the perspective of culture and institutional environment．