"The Power Broker: Robert Moses and the Fall of New York" by Robert Caro

This is an incredibly long biography of a man who figured out how to build an urban empire. While he wasn't an "entrepreneur" per se, he figured out how to generate huge amounts of revenue via tolls/bridges, how to manage and manipulate public policy, and how to attract the best urban planning talent.

... and you can then read about how it all fell apart.

Regardless of your opinion on Robert Moses / NYC, it's an incredibly fascinating read or (~90-hour) audio book.