Robert Walter Goodwillie was born on March 13, 1850 in Chicago, Illinois. He was the oldest of six children born to David and Cecelia Goodwillie. David Goodwillie was the proprietor of a box factory in Chicago where Robert and his younger brother James found employment and learned the business.
In about 1873, while still residing in Chicago, Goodwillie married Pennsylvania native, Agnes Jones. At least three children were born to this union including Grace. Lillian and Agnes. In 1889, Goodwillie, in partnership with his brother James, opened a box factory in Wausau, Wisconsin, which employed 70 men and produced 6,000 wooden boxes per day. By 1892, the box factory had expanded and employed approximately 220 men.