Latin American countries have been increasingly interested in adopting public policies aimed at dynamic entrepreneurship as a way of increasing income levels, as well as reducing poverty and social inequality. Chile stands out in the region as a country that for more than 50 years has been promoting legislative measures to build an “institutional framework” that favors entrepreneurial development. The Start-Up Chile (SUP) program, launched at the beginning of Sebastián Piñera’s administration in 2010, offered incentives to high-potential entrepreneurs from all over the world to launch their business initiatives in Chile. The idea was not only to help these initiatives thrive, but to use the experience as a source of inspiration for Chilean citizens to become worldclass entrepreneurs. This paper describes the measures implemented by the government as it executed its bold program; from the conception of the pilot program, to the adjustments resulting from experiences attained through the successive generations of entrepreneurs. It also highlights the difficulties organizers had to overcome when facing the social, economic, political and cultural challenges that are still prevalent in the country.