Pleasant Rowland takes a trip to Colonial Williamsburg in the mid-1980s. She is inspired by the "living history" of the setting. Later, seeking dolls as a gift, she sees that there are very few dolls marketed as companions to a girl or focusing on girlhood.
The original line is modeled off of a line of dolls once produced by Gotz dollmakers.
Original sketches show that the name "Pleasantries" was considered before the name Pleasant Company. Pleasant Company opens its first offices in a converted warehouse in Madison, Wisconsin in 1985, before any releases.