Arguably it was the British who were being entrepreneurial then as, put in historical context, colonising countries was primarily for economic gain - Land equalled money then, through taxes. We replaced the aristocracy with the government, which is now collecting the taxes instead. When we created the government, the Aristocracy had to find new vehicles for wealth creation so the created 'Corporations', hence why all big trade missions were funded by entities like the 'Corporation of London'. This gave the rich a way of passing wealth down the family without being taxed on it.
The David / Goliath analogy is rather paradoxical as it is American companies that lead globalisation and are the largest in the world. Google has a turnover in the BILLIONS; sorry that's not quite mom and pop corner store.....they are a goliath. But I am not here to give business lessons.
Please allow me to try focusing this discussion. I am interested in your brain/personality/experience. I'm asking YOU, as individuals and Americans how you feel. How does starting up make YOU feel? I believe the answer lies in societal norms and, therefore, American attitudes. This, I agree, has to do with historical trends.