Born 3 Jan 1864 on the farm South Veslum farm (61.51333 9.39690) in Kvikne, Nord-Fron, Oppland County, Norway, in the historic region of Gudbrandsdalen, Ole was the second of nine children born to Jacob Olsen and Kari Halvorsdatter. He was baptized 31 Jan 1864 at the Kvikne Church in Nord-Fron. On 27 Mar 1864, Jacob, Kari, their daughter Ingeborg, and Ole signed out of Nord-Fron to go to America. (From Fron church records, by Espa.)

Ole grew up near Coon Valley, Wisconsin, and was confirmed at Upper Coon Valley Lutheran Church September 22, 1878. He left Coon Valley in April 1882, and settled permanently in Tanberg Township, Wilkin Co., Minnesota, west of Rothsay, in 1897. A 1904 biography of Ole can be found online.

Ole is listed on the 1880 U.S. census as "Ole Olson," living in Greenfield Township, La Crosse County, Wisconsin, and on the 1895 Minnesota census as "Ole Jackson," living in Tanberg Township, Wilkin County, Minnesota. He grew up using the name Ole Jacobson and added Lillevold to his name around 1897.

While in Tanberg twp, he held the following elective offices:

- A director of the Farmers' Grain and Mercantile Company, which operated grain elevators in Rothsay and Lawndale;

- Secretary and Treasurer of the Rothsay Co-operative Association, which operated a general store in Rothsay;

- Clerk of the school board of District 27 in Tanberg Township;

- Official for Tanberg Township for most of the time he lived there, serving several terms on the Town Board, including as its chairman, highway overseer, and was township assessor for many years.

Ole's Y-DNA haplogroup was I-M253 (from a 2016 23andMe test of his male-line grandnephew), and his mitochondrial (maternal) DNA haplogroup was H1c10 (from a DNA test of a distant female-line relative).