Studies on the impact of innovation for entrepreneurship indicate that innovation is important to foster businesses through new or improved services, products or processes. However, from a gender perspective, lack of competitiveness and innovativeness has proven to destructively affect entrepreneurs, which in many cases led to failure. There is a gap in literature on the necessity for entrepreneurship educators for a gendered educational approach, targeting the perceived fear of failure and its impact on entrepreneurial innovation. Using Global Entrepreneurship Monitor data from 1,668 entrepreneurs in Thailand, this study explores if entrepreneurs innovate in new or improved services, products or processes despite fearing to fail in their businesses: Does this differ by gender, change over time from a start-up to an established business and to which extent can this be influenced by knowing other entrepreneurs? The findings indicate that the moderating effect of knowing an entrepreneur considerably increases innovativeness by impacting fear of failure for both genders in early-stage ventures and for women in established businesses, thus reducing the fear's negative relationship to uncertainty, risk-taking and in series constraining entrepreneurial activity. Entrepreneurship education can help overcome fear of failure and in series lead to more innovative products, services and processes.