[1] Prior to his election to the state legislature, Olsen was chairman of the Laramie County Republican Party.
[3] Olsen challenged incumbent Democratic Representative and House Minority Leader Mary Throne for the seat.
He ran unopposed in the Republican primary and defeated Throne in the general election with 51% of the vote.
[4] Olsen ran unopposed in the August 21, 2018 Republican Primary and defeated Calob Taylor, a Democrat, in the November 6, 2018 General Election with 1,275 votes (53.6%).
[5][6] Olsen ran unopposed in the August 18, 2020 Republican Primary and defeated Amy Spieker, a Democrat, in the November 3, 2020 General Election with 1,807 votes (55.0%).