Conversation so far:
What were Daniel Boone's businesses?
he kept a tavern and worked as a surveyor, horse trader, and land speculator.
Was  he successful?
He was initially prosperous, owning seven slaves by 1787, a relatively large number for Kentucky at the time.
what happened to change his prosperity?
Boone the trailblazer was too unsophisticated for the civilization which followed him and which eventually defrauded him of his land.

Question: what did he do after this happened?
Self-contained rewrite: what did Daniel Boone do after the defraudation of his land?