Born and raised in Findlay, Ohio, Redpath graduated from Indiana University and then earned an MBA from the University of Chicago. He is a Certified Public Accountant currently licensed in Virginia, a Chartered Financial Analyst, and an Accredited Senior Appraiser in Business Valuation in the American Society of Appraisers. He also holds the Accredited in Business Valuation designation from the American Institute of Certified Public Accountants and has earned the Certificate in Investment Performance Measurement from the CFA Institute.
Redpath joined the Libertarian Party in 1984. He is noted within the Libertarian Party for his ballot access work; during his tenure as chairman of the LP's Ballot Access Committee, the party's presidential ticket achieved ballot access in all 50 states in two consecutive elections (1992 and 1996). It was the first time that a minor party's presidential ticket appeared on the ballot in all 50 states and DC in successive presidential elections.
He served as Chairman of the Libertarian Party of Virginia from 1989 to 1991, and from 2014 to 2016. He twice previously served as the National Treasurer of the Libertarian National Committee, from 1991–1993 and from 2003–2004.
Redpath ran for the Virginia House of Delegates in 1993, and for the Virginia Senate in a special election in 1998. He was the Libertarian candidate for Governor of Virginia in 2001, receiving 0.8% of the vote. The theme of his campaign was "Anything That's Peaceful," the title of a book on libertarianism by Leonard Read.
He was first elected as National Chair of the Libertarian Party by delegates to the 2006 Libertarian National Convention in Portland, Oregon in July 2006. He was re-elected by delegates to the 2008 Libertarian National Convention in Denver, Colorado on May 26, 2008.