Before becoming a founding partner of the Ashven Group, Ashcraft served in numerous capacities ranging from researcher to campaign manager in everything from municipal races in Arkansas and Illinois all the way up the ballot with Gore2000. In 1998 Ashcraft worked as a field representative in Mark Pryor’s bid to become Arkansas Attorney General. After the successful campaign Ashcraft joined Pryor in the Arkansas Attorney General’s Office. During that time he served in the Government Affairs division working with elected officials and constituents across the state in addition to legislative redistricting, internet safety and lobbying on behalf of Attorney General Pryor's legislative package. Ashcraft also served as an advisor for Pryor’s successful 2004 U.S. Senate campaign.

One of Ashcrafts greatest tools in politics has been his experience as Chairman of the Jefferson County Election Commission. Ashcraft became Chairman at the age of 24 making him the youngest election commissioner in Arkansas history. In his 6 years as Chairman he has administered over 30 elections positioning him with a true “insiders perspective” almost unmatched in our industry. Ashcraft has a clear record of political experience not only from how a client views it but also the nuts and bolts of what makes an election work from the inside. Along with this is a thorough understanding of the laws and regulations surrounding elections and referendums, including the Help America Vote Act.

With all of Ashcraft’s political and governmental experience he may be most known for his command of media relations. Ashcraft has hosted two radio talk shows in addition to providing radio play-by-play for White Hall High School football. With his quick wit and knowledge of national and local issues Ashcraft allowed callers to question and discuss issues with his many guests which ranged from local elected officials, school superintendents, state legislators and members of Congress. In addition to being behind the microphone he has also appeared as a guest of several talk shows and has performed television interviews for each of the national affiliates in Little Rock, Arkansas. Ashcraft has appeared as a guest columnist in the Pine Bluff Commercial and has been quoted in the Washington Post, New York Times, Atlanta-Journal Constitution and Arkansas Democrat Gazette to name a few plus papers as far away as Mexico and Germany regarding election issues. Ashcraft has also been featured on a segment of Hannity & Colmes during the 2004 presidential election as well as CNN and MSNBC. After Hurricane Katrina Ashcraft was a contributor to the O’Reilly Factor on Fox News Channel and for “Rescue & Recovery” on MSNBC.

In September 2005 Arkansas Governor Mike Huckabee appointed Ashcraft to head up the Pine Bluff K.A.R.E. (Katrina Assistance Relief Effort) Camp for Hurricane Evacuees. In this capacity Ashcraft took on the responsibility of coordinating efforts in cooperation with the Arkansas Governors Office, State Police, Office of Emergency Management, FEMA and countless local government and community organizations such as the Red Cross. Ashcraft is a graduate of the Ron Brown – Paul Tully Institute for Political Action, a graduate of the Campaign Development Institute and numerous other campaign and election schools and is now often sought after to speak at or teach campaign courses.

In 2000 he was selected as one of the “Top 30 under 30” in Arkansas politics by politicsar.com and in May of 2006 he was recognized by the Pine Bluff Commercial as one of the "Top 30 under 30 for Southeast Arkansas".

Ashcraft is a member of the Pine Bluff Chamber of Commerce, Jefferson County Clean & Beautiful Commission, Ducks Unlimited committee and has served on the Allocations Board for the United Way. Ashcraft has also served several positions for the Arkansas Democratic Party including the State Committee, Executive Committee and Rules Committee. He is also a member of the First Baptist Church of Pine Bluff, Arkansas.