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).

 
Wayman was one of the leaders and outstanding citizens of St. Louis for half a century. From 1835 to 1855, he built an extremely successful dry goods business and amassed wealth through land and stock purchases. His prominent achivements include: 1840 - Pres. of St. Louis Chamber of Commerce; 1840 & 1850 - elected to State Senate on Whig ticket; helped get charters for Hannibal and St. Joe Railroad and Missouri Pacific Railroad; obtained Charter for the St. Louis Asylum for the Blind and the Merchantile Library Hall; 1844 - Pres. of Marine Ins. Co.; Pres. of St. Louis Perpetual Ins. Co.; Founder of Washington Univ. in 1853. He was an art patron. Harriet Hosmer, well known sculptress lived in his home and was commissioned by Wayman to execute "Beatrice Cenci" for the Mercantile Library. He built the first art gallary in St. Louis as a memorial to his son, Wayman. It's collection became the foundation to the City Art Museum of St. Louis.
 
 
One interesting story, on November 1, 1855, Wayman nearly lost his life on the ill-fated inaugural train ride across the new Gasconade Bridge. For the first time, the bridge opened railway traffic between St. Louis and Jefferson City. There were many luminaries aboard the Missouri Pacific Train, including Mayor Washington and the city council. Shortly after the locomotive began crossing the span, the new bridge gave way, hurling the train thirty feet into the river below. Thirty-one people were killed. Wayman was injured but survived. Mayor Washington also survived the crash.