Ladd and his brother Tim are co-owners of the Drummond Land & Cattle Co. Fred Drummond, the family patriarch, founded it in the late 1800s. Similarly, in 2016, the brother opened The Merc. The restaurant’s retail store is housed in a 100-year-old structure in Pawhuska’s downtown district. In 2018, the brothers opened The Boarding House, a bed and breakfast. They also opened P-Town Pizza and Charlie’s Sweet Shop, an ice cream restaurant.
The brothers are said to make around $2.5 million per year, according to sources. Furthermore, they are paid $2 million per year by the government to keep wild horses and burros on their land. The Drummond family owns 433,000 acres of property, making them the 23rd largest landowner in the United States.