ogan Stipp was born in Downing, Missouri in 1885 and moved west as a young man. For a time, he was employed as a prison guard at San Quentin Prison near San Francisco, California. In 1917, Logan went to Alaska, starting out in Knik and moving to Anchorage in 1920. He was employed by the Alaska Railroad, first as a locomotive fireman and later as a locomotive engineer.

While in Anchorage, he met Bertha Hubbard, who was born in San Francisco in 1896 and raised near Yreka, on the Klamath River. She had come to Anchorage with her brother, John Hubbard, who was employed by the city of Anchorage. Logan and Bertha were married in Yreka, California.

During their time in Anchorage, Logan and Bertha purchased the Winn Hotel located on the corner of 4th Avenue and B Street, and operated it for fifteen years. Logan and Bertha had one daughter, Wanda Stipp, born in Anchorage in 1920.

After thirty years of service with the Alaska Railroad, Logan retired with Bertha to Yreka, California. Their daughter Wanda remained in Anchorage, where she worked for the Anchorage Telephone Department until her retirement. Logan Stipp died in 1959 and Bertha Hubbard Stipp died in 1970, and they are buried in Yreka.