Gaskill was a grain farmer and a director of Meta Financial Group, Incorporated (Nasdaq: CASH), a bank holding company.

He also was a commissioner of both Iowa's Department of Economic Development and its Department of Natural Resources, president of Iowa Corn Growers Association, president of National Corn Growers Association, chairman of the United States Feed Grains Council, and held other agriculture positions.

[5][6] He supported Rudolph Giuliani in the 2008 Republican presidential primary campaign as Iowa chairman of Farmers for Rudy, and as a national co-chairman.

[8][9] He graduated from Corwith High School in 1953 and attended Iowa State University.

He began farming in 1958 on rented property and expanded over the years, purchasing his own land.