Skyler joined Clemon-Maki Insurance in July of 2017 and is currently licensed in property and casualty insurance. In January of 2026 he became part owner with Darin Eide and Alex Modlin. Skyler was born and raised in Newton and moved to Excelsior Springs, Missouri his sophomore year of high school. After attending and playing football at Missouri Valley College, Skyler moved back to Newton. He married his wife Abbie in 2014 and they have one son, Liam. Skyler is a member of the Izaak Walton League and participates in many sports offered by the YMCA in Newton.