This article reports on how a pedagogical entrepreneurship approach combined with fundamental elements of mathematical modelling may be used to strengthen students' development of mathematical literacy in upper primary school. This is done first through a review of the relationship between pedagogical entrepreneurship in mathematics, mathematical modelling, and mathematical literacy, and then through presentation of a best practice example where the pedagogical entrepreneurship approach and mathematical modelling have been the foundation for an assignment given to teacher education students. An action-research perspective influenced by self-study methodology has been used in identification and presentation of the best-practice example. The example shows that through emphasis on mathematical modelling and a scientific approach based on pedagogical entrepreneurship, we may have expectations towards increase of upper primary school students' development of mathematical literacy. In conclusion, key elements in pedagogical entrepreneurship like authenticity, relevance, and value for others enrich the mathematical modelling process, and provide valuable stepping-stones for the upper primary school students' development of mathematical literacy.