Gregory owns a farm alongside his wife, Kella, and his parents, Roger, and Ruth. Together, they farm corn and soybeans on 1,100 acres and custom feed 2.400 pigs for a local family-owned hog operation. Gregory has served on the board of directors for Missouri Corn Growers and is a local delegate for MFA Oil. He is also a member of the Saline County Farm Bureau, Missouri Corn Growers Association, and Missouri Cattlemen's. Gregory was awarded the Farm Bureau Friend of Agriculture Award in 2022 and was in the Corn Growers inaugural CornRoots Leadership Class in 2013.

Before going back to the farm, Gregory also had a short stint in the NFL with the Carolina Panthers. Kurtis played on the University of Missouri football team from 2006-2009. He played Left Tackle in 2006 and then started 41 straight games at Right Guard from 2007 until he graduated. In 2007, his Tigers beat Arkansas in the Cotton Bowl and finished the season ranked 4th in the nation. In 2008, they beat Northwestern in the Alamo Bowl, and in 2009, Gregory served as team captain.

Representative Gregory has been a national pioneer in Name, Image, and Likeness legislation passing multiple influential bills in his time in the legislature. In 2023, along with SEC Commissioner Greg Sanky, and Condoleezza Rice, Sports Illustrated named Gregory one of the 25 Most Intriguing Suits in College Football.

Born in Blackburn, Missouri, Gregory currently resides in Marshall with his wife, Kella, and three children, Brook, Landon, and Henley, where they attend Calvary Baptist Church. Gregory is a graduate of Santa Fe R-10 High School and earned his Bachelor's degree and a Master's degree in General Agriculture from the University of Missouri.