Toby Keith’s empire: Capitalist entrepreneur and country music hitmaker

Toby Keith had more than just a knack for writing and recording No. 1 records – the country music superstar was also bitten by the entrepreneurial bug, and dabbled in a variety of business ventures during his lifetime.

The 62-year-old country music legend, who was diagnosed with stomach cancer in 2022, died Monday surrounded by his family, according to a statement posted to his website and social media accounts.

Keith, with hits like “Should’ve Been a Cowboy,” “How Do You Like Me Now?!” and “Who’s That Man,” found success not only on the Billboard charts, but also with multiple business ventures in the fishing, cannabis, food and drink, and horse racing industries.

TRIBUTES POUR IN FOR TOBY KEITH, LEGENDARY ‘COURTESY OF THE RED, WHITE AND BLUE’ SINGER DEAD AT 62

Forbes once dubbed Keith a “Capitalist Cowboy,” and he appeared on the outlet’s Celebrity 100 list on multiple occasions.

Luck E Strike

The country star purchased Luck E Strike, a company that makes bait and tackle for fishing, in May 2023.

Keith learned that the business was for sale through its general manager, and said in a statement that the company “needed a new focus and vision and I happened to be standing at the door ready to pick up the pieces.”

The company has been around since the 1970s.

Big Dog Cannabis Co.

Keith also started a cannabis company a few years ago called Big Dog Cannabis Co.

It has an “exclusive focus on licensing” for cannabis flower, concentrates, edibles and pre-rolls, its website stated.

Albuquerque Business First reported in mid-December that Big Dog Cannabis Co. products would become available at dispensary Seven Clover in New Mexico. Prior to that, the brand’s presence was limited to Oklahoma, according to the outlet. 

Wild Shot

Keith launched a mezcal brand called Wild Shot in 2011. It contains “handcrafted, 100% green agave” and is 86.8 proof, according to a 2014 press release.

Toby Keith’s I Love This Bar & Grill

Elsewhere in the food and beverages industry, there are Toby Keith’s I Love This Bar & Grill restaurants that use his name through licensing agreements, The Tennessean reported.

The name stems from his 2003 song “I Love This Bar.” The chain offers burgers, sandwiches, Tex-Mex, barbecue and other items.

At one point, there were more than two dozen restaurants in operation. But after a management company faced a series of legal issues, the number dwindled to just two. Both are in Oklahoma, Keith’s home state, and are operated by different management.

Dream Walkin’ Farms

Keith had an interest in horse racing too. 

His Dream Walkin’ Farms breeds and races thoroughbred horses, some of which have won stakes races. The farm has notched nearly 6,600 starts and nearly 850 wins, according to Equibase.

The country singer would stop by racetracks at times to see his horses compete, according to reports.

Music

Those businesses came on top of his well-known presence in the music industry. He created his own Show Dog record label and had ties to Big Machine Records.

His various albums have racked up some 40 million sales, according to the Songwriters Hall of Fame. Keith also notched over 10 billion streams of his song catalog. Overall, he released 21 studio albums and 69 singles, 20 of which reached No. 1 on Billboard’s country charts.

In December, he performed three nights in Las Vegas to sold-out crowds.