Venture capital allows startups to scale and be successful quickly, yet women have historically been excluded from a majority of this funding. We explore the potential explanation that investors ask entrepreneurs different questions on the basis of gender, perhaps subconsciously revealing a cognitive bias that assumes women are more likely to fail. Using a newly-created Shark Tank dataset and predictive modeling through natural language processing, we find no significant quantitative backing for this explanation, though we do see some evidence in support through a qualitative analysis.