He is described as "phlegmatic, stoical, inclined to sulk if displeased, a cautious penny-pincher, and unable to reach a decision without ponderous deliberation.

In 1824, at the age of 17, he ventured from home to first work in the lead mines at Galena, Illinois, and then to St. Louis, Missouri, clerked for a time in the Berhoud & McCreery dry goods store.

[3] In 1835, Waddell again moved his family, this time to Lexington, Missouri, where he opened another dry goods store on the waterfront near Jack's Ferry.

[2] This firm obtained a consolidated contract with the War Department to supply the majority of military forts west of the Missouri River.

By October 1861, the Express was out of business due to the completion of the telegraph lines and the unwillingness of the national government to provide further funding.

[8] Following the failure of the Pony Express in 1861 and a financing scandal created by Russell, Waddell retired to his home in Lexington and never entered business again.