In 2016, Eurydice reported that no country in Europe had fully integrated entrepreneurial education in schools and that teacher training was fragmented. However, supported by the World Bank, North Macedonia introduced a compulsory and progressively evaluated Entrepreneurship and Innovation curriculum in 2016, following policy decisions made in 2014. Teacher training initiatives from Wales informed progress. The Welsh Government decided to integrate an entrepreneurial culture within curriculum and assessment arrangements in schools which built upon prior work including education within Initial Teacher Training. This included funding to pilot training for teachers at all levels, from schools to universities and across all subject specialisms—to develop entrepreneurial education. Welsh Government’s Youth Entrepreneurship Strategy (YES) commenced in 2004 within the Ministry for Business and Transport (now Business Economy and Innovation), and since 2015, has been supported by the Ministry of Education and Skills. The sector now has 10 years of experience in entrepreneurial teacher training and has developed Doctoral-level study for educational leaders. In February 2020, the theme of ‘creative enterprising contributors’ was formally positioned as one of the four overarching ‘purposes’ of school education in Wales. This article provides reflective insights of knowledge exchange through the lens of the International Institute for Creative Entrepreneurial Development, in both a Macedonian and Welsh context, and will be of interest to those who wish to advance national policies and entrepreneurial educator development.