Conversation so far:
What were Daniel Boone's businesses?
A celebrity, Daniel Boone kept a tavern in Limestone, and also worked as a surveyor, horse trader and land speculator.
Was Daniel Boone successful with his businesses?
Daniel Boone was initially prosperous, owning seven slaves by 1787 (a relatively large number for Kentucky at the time), but began to have financial troubles while living in Limestone.

Question: what happened to change his prosperity?
Self-contained rewrite: What happened to change Daniel Boone prosperity?