Does the mass media promote entrepreneurship? Using big data in combination with a machine learning aided analysis we discover a positive sentiment bias associated with entrepreneurship present in two major English language media outlets – The New York Times and the Financial Times. Over eight hundred thousand excerpts from a 12 and 16-year period were analyzed. Those containing the words ‘entrepreneur’ and ‘founder’ had much more positive sentiment than did excerpts with the words ‘manager’ and ‘executive’. A parallel analysis of the FANG companies (Facebook, Amazon, Netflix and Google) in comparison to a set of older and more established Fortune 500 companies produced similar results. While more work is needed to make the link between media biases and career choice, we believe this media bias promotes entrepreneurship, resulting in lower (average) incomes and higher risks for those engaged in this career path. However, because entrepreneurial activity can create positive externalities in the broader economy this bias, while financially disadvantageous for the average entrepreneur, may be beneficial overall for their society.