Claybourn is a native of Evansville, Indiana. He graduated from North High School and earned a bachelor's degree from Indiana University Kelley School of Business. He also attended the Leadership Institute in Arlington, Virginia, an organization that teaches young Americans how to influence public policy through activism and leadership. Thereafter he earned a law degree from Indiana University Robert H. McKinney School of Law and served as a research assistant to Professor Gerard Magliocca during his work on Andrew Jackson and the Constitution: The Rise and Fall of Generational Regimes.
Claybourn is an attorney with the law firm of Jackson Kelly and represents businesses and several governmental entities and officials. He served as attorney for the city council of Evansville, Indiana, and the town council of Chandler, Indiana. Citing Article 1, Section 2 of the United States Constitution, Claybourn appeared before the Indiana Election Commission and successfully challenged a 23-year-old person's legal right to appear on the ballot as a candidate for Congress in Indiana's 8th congressional district. He previously served as an adjunct professor of business law at the University of Evansville. Despite high-profile criticism of Donald Trump, members of his transition team sought Claybourn's interest in a legal role with the administration, suggesting his involvement would be "good for unity".
Claybourn is a co-editor (with William Bartelt) of the forthcoming book titled Abraham Lincoln's Youth: Works from Indiana's Lincoln Inquiry, under contract with Indiana University Press, and previously edited A Memorandum of the 80th Illinois Infantry: Civil War Notes of Pvt. Armgstrong McGee. He is an adjunct scholar with the Indiana Policy Review Foundation and work has appeared in USA Today, The Hill, The Federalist, The American Spectator, National Review Online, American Thinker, and World Magazine, as well as regional publications such as the Indianapolis Star, Evansville Courier & Press, The News-Sentinel, and The Herald-Times. On television he has commented on current events on CNN, MSNBC, and NHK. Previously he was a blogger that radio talk show host Hugh Hewitt included among the "next generation of bloggers" and a reason "to be very optimistic about the future of the blogosphere."
Writing in The Hill and The American Spectator, he argued against passage of the Justice Against Sponsors of Terrorism Act, warning that it threatened to "undermine foreign relations, core principles of international law, and American justice abroad." Claybourn is an outspoken advocate of home rule, a principle in Indiana and several other states that generally grants municipalities the power to govern themselves as they see fit. He is also a former trustee and president of the Evansville Vanderburgh Public Library.
Claybourn was cited as a "key supporter" of Congressman Larry Bucshon of Indiana's 8th congressional district. He was a principal adviser to Evansville Mayor Lloyd Winnecke's campaign and was a part of Winnecke's 2012 transition team. He also served as a top adviser during Winnecke's successful 2015 re-election campaign, which made Winnecke the first Republican Evansville mayor to be re-elected in 40 years.