Wayman was born in Hartford, KY and began his schooling in Hopkinville. In 1820, at age 12, he quit working on the family farm and was apprenticed to a dry good dealer of that city for a period of 5 years. In 1825, he agreed to open a branch store in Cadiz, which he bought out Jan. 1, 1829. He built a respected reputation in the community and was appointed postmaster of Cadiz at the age of 19. In 1835, he sold his store and went into partnership with his cousin, Joshua Tevis, to form a very successful mercantile history of Crow & Tevis (later Crow, McCreery).