This paper discusses cultural influences on the success of women in Information Technology (IT) careers that emerged from 38 interviews with career women in Southern California. Interviews, conducted in 2008, lasted 60-90 minutes each. The women’s career stories reflect on comparable experiences with organizational and workgroup cultures, as well as occupational cultures and subcultures. Except for primarily female organizations, “old-boy” culture prevails at the upper levels of most organizations. Women who have climbed to those levels still feel like outsiders. Women complained about “old-school” occupational cultures, but they valued trust in their workgroup cultures, when and where that exists. “Token” women often experienced the most difficulties.