Webb worked as a rider on the express mail route established under Andrew Jackson's administration. He later settled in Elyton and then became one of the first to build upon a newly-auctioned lot in the City of Birmingham. His Webb Building won him a $100 prize from the Elyton Land Company upon completion. He operated a grocery and wholesale whiskey business as well as the Dude Saloon on the ground floor of his building. He was also a boarder in his own building. The house was kept by Mrs B. H. McCoy, the wife of Webb's clerk.
Webb was appointed to the first Birmingham Board of Aldermen by Governor Robert Lindsay, serving under the administration of Robert Henley. Webb was a founding director of the Birmingham Manufacturing Company in 1874. He returned to public service as City Marshal under Mayor William Morris, effectively serving as Chief of the Birmingham Police Department from 1875 to 1876.
The Birmingham Iron Age printed an editorial on February 24, 1876 urging the Birmingham Board of Aldermen to draft an ordinance forbidding any man who "keeps, or is interested in keeping, a drinking saloon," from holding any city office. Webb closed his saloon in January 1877 and converted the space into a "family" grocery store. His property on 2nd Avenue was advertised for sale at a Sheriff's auction later that same month. He owned numerous other properties around the city that made him wealthy in his later years.
Webb married the former Sarah Hicks on January 16, 1854 in Bibb County. They had seven children, five of whom died in childhood. John Alexander Webb and William J. Webb survived to adulthood, but both died in the 1880s. John B. Webb died in 1901 and is buried at Oak Hill Cemetery. The bulk of his estate, including the Dude Saloon and the Ferd Marx Store passed to his daughter, Columbia McCoy, leaving her sister, Corinthia Burnett with only a paltry inheritance. At the time the will was filed in probate, the two sisters entered into an agreement to establish a more equitable settlement of the estate.
- "Changes" (January 17, 1877) Birmingham Age-Herald, p. 3
- City Directory of Birmingham and Gazetteer of Surrounding Section for 1884-5 (1884) Volume II. Atlanta, Georgia: Interstate Directory Company
- "Captain Webb's Will" (July 20, 1901) The Montgomery Advertiser
- John B. Webb at Findagrave.com