After Carl Dragstedt earned his college degree in 1923, he went into business with a man operating out of China and moved to Shanghai. After his partner's sudden death in 1925, Carl returned to Missoula. In 1926, Carl his father Charles opened up a men’s clothing department store in downtown Missoula, just three years prior to the stock market crash that precipitated the Great Depression.
Dragstedt's survived the depression. Carl Dragstedt later said that he was fortunate in his business life because everyone knew that times were tough at that point and people just had to “tighten their belts.”(Carl Dragstedt Interview) Despite a lack of sales and a lack of revenue, the financial constraint did not cause the business to go under. Rather, the business adopted a credit arrangement for customers. Later, Carl Dragstedt acknowledged his good fortune that everyone was able to pay back their debt.
The Dragstedt family was committed to community service. The family partly owned the Tripp & Dragstedt Store in Anaconda, a business that was so integrated into its local community that it helped build churches and even supported local legislation. In Missoula, Carl continued the family tradition of contributing to the community by helping the University of Montana acquire the Prescott House and providing for an athletic scholarship to the school.
When Carl Dragstedt was ready to retire, he asked his grandchildren if they would like to have his store. All declined, so in 1978, Carl sold his business to a man who owned a second hand store. The original purchaser of the building still keeps in touch with Carl’s grandchildren, but the building has been sold several times and split into two commercial spaces. It now houses OZ architects and Pie Hole pizzeria.