Which were the most entrepreneurial AND prosperous cities in different eras?

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Novgorod is a great fit

Novgorod (meaning New City), founded before 859, was a major city on the trade route from the Baltic to the Black sea. Later on, it became a prominent city of the Hanseatic League, and produced many trade goods such as furs, honey, and religious artworks. It enjoyed a high degree of culture and literacy. Starting from 1136, it was an early democracy where even the lower classes (but not serfs) were able to vote. From its inception, Novgorod has been a crossroads between Scandinavian, Baltic, and Slavic cultures.

Novgorod was the capital of the eponymous Russian principality for centuries, and was one of the few places that emerged relatively unscathed from the Mongol yoke. Sadly for Novgorod, it was annexed by Muscovy in 1478, and its influence and prosperity declined rapidly.

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