The elder Hindman frequently made business trips to Alabama and even moved the family to Jacksonville after buying several lots of land there. He took advantage of the many local business opportunities and was able to provide his family with whatever they needed. He also gained a reputation for honesty with his business associates, which included Cherokee Indian tribes in the area. Hindman became trusted by the Cherokee Nation and was appointed as the sub-agent to the Cherokees by President James Monroe. After Andrew Jackson became president, Hindman, Sr. was appointed to the post of United States Agent for the Cherokee Nation. The elder Hindman frequently traveled to Washington D.C. to discuss the interests of the Cherokee Nation, and in 1841 was assigned by Acting Secretary of War Albert M. Lea to determine why the Cherokees in North Carolina had rejected the government's suggestion to join other parts of the tribe in Indian Territory. Hindman spent almost two months unsuccessfully trying to persuade the North Carolina Cherokees to rejoin the rest of their nation further West.