How Toby Keith’s Multi-Millions in Investments Made Him a Mogul

Country music fans know Toby Keith for his patriotic anthems, love songs, and borderline comedic redneck songs, but he was also a formidable businessman and entrepreneur, earning him Forbes notoriety as a “500 Million Dollar Man.”

The “I Wanna Talk About Me” singer invested in and started many businesses, including a bait and tackle shop called Luck E Strike. Luck E Strike appeared to be brought back to life by Keith’s investment in 2023. The singer took his love for singing about the country to his pocketbook with this investment, according to Fox Business.

His “I Love This Bar” song took on a new meaning with a bar sporting the song name. His bar currently has two locations and is a big draw to his bar-hopping fans.

Keith’s love for horses really showed through his investment in Dream Walkin’ Farms, which trained racehorses. The farm’s horses brought in 850 wins, according to Equibase. He was known for his love for horses and sang about it in his hit song, “Beer for My Horses.”

Another business venture that Keith took part in was Big Dog Cannabis. The “How Do You Like Me Now” singer started this business from the ground up. It licensed cannabis flowers, edibles, and pre rolls according to Fox Business.

The “Red Solo Cup” singer also had a Mezcal alcohol business called Wild Shot.

Those business investments added to his fortune, but his music was still an important part of his overall financial picture. According to the Songwriters Hall of Fame, Keith has brought in over $40 million in song sales.

Keith also owned Show Dog Records, which had a relationship tie to Big Machine Label Group. It recently disbanded according to Music Row.

Toby Keith’s Mega Millions in Investments

Toby Keith’s net worth was astounding, but his music was just the tip of the iceberg.

Gallery Credit: Nicole Taylor

Music

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Music

Keith has racked up around $40 million in sales according to the Songwriters Hall of Fame. He has countless hits and has developed a legacy of fandom. He also owned Show Dog Records, which had ties with Big Machine Label Group. It started in 2005 but was recently disbanded, according to Music Row.

I Love This Bar and Grill

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I Love This Bar and Grill

I Love this Bar and Grill was inspired by Keith’s hit song, “I Love this Bar.” There are two restaurants in operation which serve burgers and BBQ.

Wild Shot

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Wild Shot

Keith’s Wild Shot Mezcal alcohol company was started in 2011. It’s 100 percent green agave and 86.8 proof, according to Fox Business.

Dream Walkin’ Farms

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Dream Walkin’ Farms

Keith had an interest in racing. According to Equibase, Keith’s horses have racked up close to 850 wins.

Luck E Strike

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Luck E Strike

A company that makes bait and tackle. It was purchased by Toby Keith in 2023. Luck E Strike has been around since the 1970s according to Fox Business.

Big Dog Cannabis Co.

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Big Dog Cannabis Co.

The cannabis company was started by Keith. It licensed cannabis flower, edibles, pre-rolls and concentrates according to Fox Business.