Toby Keith is perhaps best known for his music, followed by his Love This Bar and Grill restraint chain. He’s actually the head of an empire that expands far beyond music and food, and according to Forbes, has raked in $65 million in the last 12 months, only outpaced by the likes of Madonna, Lady Gaga and Bon Jovi and surpassing Jay-Z, Beyonce and Jennifer Lopez.
“He’s built this little empire, and he did it kind of quietly,” concert promoter Louis Messina told Forbes. “Not many people have been able to pull it off as long as he has.”
Over the past five years, Forbes estimates Toby has never earned less than $48 million in a given year, pulling $270 million over that time period. His career earnings surpass $500 million. Despite his empire, people know little about Toby overall. Country music reaches only 14% of the national radio audience. Toby knows how to leverage his passionate fan base. “A big rock station might play a hit 100-plus times per week,” Toby’s manager, TK Kimbrell, said. “A country station might play it 50 times. But they’ll play it forever.”
Toby’s success is rooted in the oil derricks around Norman, Oklahoma. A native of nearby Moore, Oklahoma, he planned to go to college and study petroleum engineering. But as the price of crude soared in the late 1970s, he followed fast money out of high school, earning $50,000 a year climbing rigs. When the crude bubble burst, he worked part-time as a bricklayer and earned extra money playing covers at local bars with the Easy Money Band, formed with four friends. Their reach expanded to Texas, where to save money, they’d sleep two to a room in cheap hotels.
One by one, his friends left the band. Toby made the decision to replace them with musicians who would play for a salary instead of a share in take and by 1990, he owned the whole act, making $60,000 a year. Still, rejections from record labels piled up until a fan gave a demo tape to Mercury Records’ Harold Shedd on a flight to Nashville. “It was mainly the quality of what he was writing,” Harold said of the demo. “It was unlike anything on the radio at the time, and it was still really good country music.”
Harold offered Toby a $20,000 record deal which Toby accepted on the spot. His debut album was released in 1993 and went platinum, containing four No. 1 hits, all from his rejected demo, including “Should’ve Been A Cowboy,” the most played country song in the 1990s. “Last I heard, the guy [who] turned me down was cutting grass for a living,” Toby told Forbes.
Toby released a new album every year through 2000, each selling at least 500,000. In 1994, Harold launched Polydor Nashville and Toby followed him. Luke Lewis eventually took Harold’s place and didn’t share Harold’s passion for Toby’s music, telling him he didn’t hear a hit on the rough cut of his How Do You Like Me Now? album. Toby eventually agreed to buy back the rights to the album and promptly sold them to rival label DreamWorks for twice what he paid for them. The album went on to sell 3.1 million copies.
In 2004, when Universal’s Interscope bought out DreamWorks and merged the imprint with Mercury, Toby was reunited with Luke Lewis. Toby refused to work for him. When the label told him he still owed two albums according to his contract, Toby threatened to retire. He then went into business for himself, opening his own label, Show Dog. “To that I say, ‘Good luck,’” Luke Lewis told Billboard in 2005. “The track record of artists running record labels is not that good.”
Toby made the decision to share staff with Big Machine, run by Scott Borchetta. He paid $400,000 for a stake in Big Machine which, according to Forbes estimate, remains around 10%. It turned out to be an incredible investment as Scott went on to sign Taylor Swift, Tim McGraw and Rascal Flatts among other big names. Now, Toby collects a check when Taylor does.
Toby pulls in $12 million a year from his restaurant chain, I Love This Bar and Grill. In addition to his music and restaurant ventures, he’s invested in Norman, Oklahoma, including a horse farm, a Starbucks and an apartment complex. His foundation is footing a $16 million expansion of the local children’s medical center and he has his own signature mescal, Wild Shot. By the end of the year, Toby plans to have 26 restaurants up and running, each serving Toby’s signature Mezcal, Wild Shot, and each with a stage featuring new acts from his label.
“I can put them on that 30-city tour,” he said. “I don’t have to look for a place to play. It’s cost-effective as crap. They’re in Toby’s house. They’re drinking Toby’s liquor. That’s Toby’s act. And then we’re moving to the next town.”
Toby is currently headlining his Hammer Down Tour. He recently released his latest single, “Drinks After Work,” the lead track from his upcoming album, expected out later this year.