This study examined gender differences in personal, family, personality, work style, and leadership factors among a sample of highly successful business professionals. Self-report data was obtained from a survey of 56 women and 50 men, mostly from the United States, all of whom made $100,000 or more in annual personal income. Most of the respondents had senior-level positions, owned their own business, and were highly educated. Sixty percent were millionaires or multimillionaires. Contrary to past research indicating systemic gender differences that limit the success of females, this study found few gender differences overall. These women and men were similar on most of the measures tested, including parental and early-life experiences, core personality traits, work styles, leadership styles, formative career work assignments, career path life detours, and work-related failures. However, twice as many women than men reported experiencing prejudice or discrimination in their work histories. A majority of both genders acknowledged gender-specific obstacles to career success for women in general (i.e., childbearing, greater family care responsibilities, and sexism). Being a successful leader also was defined somewhat differently for women than for men. Thus, even though a high degree of similarity was found between women and men in most background and career path characteristics, traditional gender-role expectations and sexism issues still affected many of these women, and this was acknowledged by most of the men in the study as well. See companion article (Part 1) for comparisons of this sample with normative and matched samples on many of these demographic, personality, work style, and early-life experience factors. Although professional and financial success is a career goal for many, some people are able to achieve more in this area than others. It is these high achievers that are the focus of the current study. By learning from those who have already achieved success, we can discover the answers to questions of: Who are the highly successful?; What did they do to get so successful?; How do they act as leaders?; and Is the path to success and leadership different for women than for men?These are some of the topics we address in the current study of individuals who are highly successful in business and professional fields. This sample is also profiled in a companion study to this report that focuses on an examination of a large set of individual difference factors that have normative benchmarks with which to compare to the sample (Miller Burke & Attridge, 2011 [this issue]). This article builds upon the Part 1 article in three ways. The primary goal was to test for gender differences in all of the profile measures included in the first article. A second goal involved using qualitative analyses of open-ended responses to explore how a variety of personal and occupational factors contributed to career success. Third, we wanted to develop a deeper understanding of leadership and discover which specific personal qual...