We study the gender gap in a competitive environment by exploiting the “naturalistic experiment” of a TV game show with self-selected participants and no gender-specific constraints nor discrimination. Games consist of multiple rounds where contestants answer general knowledge questions privately. One participant is eliminated or leaves voluntarily at the end of each round. Women earn 40% less than men and exit the game at a faster rate, but especially when in a minority. This latter result highlights the importance of structural arrangements in organizations that interact with behavior to maintain “glass ceilings” and explains the differential gender-related risk attitudes observed.