His first known business venture came in 2005 when he launched Toby Keith’s I Love This Bar & Grill in Oklahoma City, Oklahoma. He later opened branches in Syracuse, New York, and Tulsa, Oklahoma. The restaurant now has outlets in Thackerville, Oklahoma; Auburn Hills, Michigan; Kansas City; Las Vegas; Mesa, Arizona; Peoria, Arizona; St. Louis Park, Minnesota; Foxborough, Massachusetts; Cincinnati, Ohio; Newport News, Virginia; and Denver, Colorado.
The new restaurants are actually owned by Capri Restaurant Group Enterprise LLC as they obtained a license agreement to open more Toby Keith restaurants across the country.
In 2009, Keith expanded his business exploits to include a line of clothing dubbed TK Steelman. A new drink named “Wild Shot” followed in 2011, first in Mexico before it became available in the United States.