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In this study we investigate new venture failure. We do this in two ways: first, by testing for moderating effects of new venture failure on the relationship between startup experience and perceived startup expertise with a sample of 220 entrepreneurs; and second, by qualitatively exploring the nature of these relationships, drawing insights from interviews with these 220 entrepreneurs. Our results show a disordinal crossover moderating effect of new venture failure in the relationship between startup experience and startup expertise, and also assist in the interpretation of these results. We illustrate, for practice: more productive outcomes from initial new venture failure, and for research: a deeper understanding of the “bubbling cauldron” of new venture failure.