Daniel Boone (November 2, 1734 [O.S. October 22] - September 26, 1820) was an American pioneer, explorer, woodsman, and frontiersman, whose frontier exploits made him one of the first folk heroes of the United States. Boone is most famous for his exploration and settlement of what is now Kentucky, which was then part of Virginia but on the other side of the mountains from the settled areas. As a young adult, Boone supplemented his farm income by hunting and trapping game, and selling their pelts in the fur market. Through this occupational interest, Boone first learned the easy routes to the area.
Businessman on the Ohio River
After the Revolution, Boone resettled in Limestone (renamed Maysville, Kentucky in 1786), then a booming Ohio River port. In 1787, he was elected to the Virginia state assembly as a representative from Bourbon County. In Maysville, he kept a tavern and worked as a surveyor, horse trader, and land speculator. He was initially prosperous, owning seven slaves by 1787, a relatively large number for Kentucky at the time. Boone became a celebrity while living in Maysville. In 1784, on his 50th birthday, historian John Filson published The Discovery, Settlement And present State of Kentucke, a book which included a chronicle of Boone's adventures.  The Revolutionary War had ended, but the border war with American Indians north of the Ohio River resumed with the Northwest Indian War. In September 1786, Boone took part in a military expedition into the Ohio Country led by Benjamin Logan. Back in Limestone, Boone housed and fed Shawnees who were captured during the raid, and helped to negotiate a truce and prisoner exchange. Although the war escalated and would not end until the American victory at the Battle of Fallen Timbers in 1794, the 1786 expedition was the last time Boone saw military action.  Boone began to have financial troubles while living in Maysville. According to the later folk image, Boone the trailblazer was too unsophisticated for the civilization which followed him and which eventually defrauded him of his land. Boone was not the simple frontiersman of legend, however: he engaged in land speculation on a large scale, buying and selling claims to tens of thousands of acres. The land market in frontier Kentucky was chaotic, and Boone's ventures ultimately failed because his investment strategy was faulty and because his sense of honor made him reluctant to profit at someone else's expense. According to Faragher, "Boone lacked the ruthless instincts that speculation demanded."  Frustrated with the legal hassles that went with land speculation, in 1788, Boone moved upriver to Point Pleasant, Virginia (now West Virginia). There he operated a trading post and occasionally worked as a surveyor's assistant. When Virginia created Kanawha County in 1789, Boone was appointed lieutenant colonel of the county militia. In 1791, he was elected to the Virginia legislature for the third time. He contracted to provide supplies for the Kanawha militia, but his debts prevented him from buying goods on credit, so he closed his store and returned to hunting and trapping.  In 1795, Rebecca and he moved back to Kentucky, living in present Nicholas County on land owned by their son Daniel Morgan Boone. The next year, Boone applied to Isaac Shelby, the first governor of the new state of Kentucky, for a contract to widen the Wilderness Road into a wagon route, but the contract was awarded to someone else. Meanwhile, lawsuits over conflicting land claims continued to make their way through the Kentucky courts. Boone's remaining land claims were sold off to pay legal fees and taxes, but he no longer paid attention to the process. In 1798, a warrant was issued for Boone's arrest after he ignored a summons to testify in a court case, although the sheriff never found him. That same year, the Kentucky assembly named Boone County in his honor.

Q: What were his businesses?
A: he kept a tavern and worked as a surveyor, horse trader, and land speculator.

Q: Was  he successful?
A: He was initially prosperous, owning seven slaves by 1787, a relatively large number for Kentucky at the time.

Q: what happened to change his prosperity?
A: Boone the trailblazer was too unsophisticated for the civilization which followed him and which eventually defrauded him of his land.

Q: what did he do after this happened?
A: Frustrated with the legal hassles that went with land speculation, in 1788, Boone moved upriver to Point Pleasant, Virginia (

Q: What did he do there?
A: he operated a trading post and occasionally worked as a surveyor's assistant.
Did he take a more permanent position anywhere?
When Virginia created Kanawha County in 1789, Boone was appointed lieutenant colonel of the county militia.
When Virginia created Kanawha County in 1789, Boone was appointed lieutenant colonel of the county militia.