Skyler grew up in Olympia, Washington. He attended Grays Harbor Community College to play baseball. In his time at Grays Harbor he broke several baseball records and was a first-team All-West Region selection. After his second year at Grays Harbor, Skyler earned a scholarship to attend Northwestern College in Orange City. He graduated with his Bachelor's Degree in political science. Following graduation, he took a job with Iowa Information Inc. in Sheldon. Currently he's working on his Master's Degree in Government online through Regent University.

Skyler's always had an interest in politics. In his time at Northwestern he was active in their College Republican organization. Most recently he was the Sioux County Co-Chair for Ted Cruz's presidential campaign. He's also volunteered for Christians United for Israel. Skyler and his wife, Jess attend Cornerstone Baptist Church in Orange City and are involved in a weekly young adult Bible study.