Born in Tulsa, Oklahoma, and raised in the small town nearby, Miami, Jon Wolfe’s depth of talent and commitment to craft was evident from an early age. From sketch pads to basketball courts, he did it all. “I was the guy who loved the game, but couldn’t stop drawing in the margins,” Wolfe laughs. A gifted athlete and a natural artist, he grew up balancing both lanes—until music found a way to pull him into a third.

His stepfather played bass in their church band, and his stepsister sang gospel. Though raised in an environment that discouraged secular music, Jon grew to love the crooning sounds of Frank Sinatra and Harry Connick Jr.“I grew up thinking secular music was wrong,” he admits, “but I also knew I could sing. I just didn’t know where that was supposed to go.” The home was filled with worship, harmony, and the sounds of Oklahoma’s soul—yet the wider music world always seemed just out of reach.

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After high school, Wolfe drifted down the paths of least resistance. “I didn’t have a straight path—I had ten. I played basketball in junior college thinking someday I would be in the NBA, attended Bible school, thought about youth ministry… but nothing stuck.” His heart eventually led him outdoors—to the mountains, the quiet. “There was a point when I thought I’d just go off and climb rocks in Colorado for the rest of my life.”

He eventually earned a finance degree from Colorado State and landed a job on BP’s trading floor in Chicago. Hired as one of the high potential hires, Wolfe was in charge of trading global distillates and futures – He was on the path of becoming a Wolfe of Wall Street. “It was everything I thought I was supposed to want. But deep down, I knew I wasn’t built for fluorescent lights and a cubicle.” When Wolfe was transferred to their Houston office, he started playing in dive bars and beer joints. “People kept saying, ‘You’ve got something. Go for it.’ That stuck with me.”

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By 2004, Wolfe recorded his first album and got swept into the thriving Texas country scene alongside artists like Hayes Carll and Randy Rogers. A chance connection with Trey Strait—and encouragement from Trey’s uncle, George Strait himself—led to a management contract and Wolfe’s first label deal in Nashville. “Unfortunately, that label went under pretty quickly. It could’ve been the end, but I wasn’t ready to give up.”

In 2010, Wolfe dropped his debut album, It All Happened in a Honky Tonk. Hits like “That Girl in Texas” followed. Though a major-label stint with Warner Brothers opened new doors, Wolfe chose to stay independent—building a loyal fanbase from the ground up. “I’ve always believed in the long road if it’s the honest one.”

Albums like Natural Man and Any Night in Texas made Wolfe a modern traditionalist—an artist rooted in classic country but committed to evolving. He later launched the premium tequila brand, Juan Lobo, alongside his wife, Amber. “I wanted the tequila to look as good as it tasted. Creativity’s never been limited to just music for me.”

His 2021 project Dos Corazones, was a turning point: deeply introspective, sonically daring. Entirely conceptualized and realized in the West Texas desert, the album - though it slipped under the commercial radar - firmly established Wolfe as a songwriter. “That record was me getting quiet enough to listen to what I really wanted to say.”

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Now, with Barstool Therapy, Wolfe has evolved even further: he’s sharper, and more himself than ever. Created with trusted collaborators Dave Brainard and Tony Ramey, it’s an album of heartache and horizon. “This record is the most ‘me’ I’ve ever put on tape. And it’s the project I’m most proud of.” Laced with standout tunes like lead-off single “The Older I Get (More Country I’m Gettin’ To Be)” and collabs like “Tequila Cowboys” (featuring Randy Rodgers) and “That’s Not Very Texas of You” (featuring Lyle Lovett), the project is unapologetically Wolfe - and as authentic as it gets.

“I’m not chasing fame. I’m chasing the spark. Whether it’s a song, a painting, or a label on a bottle—I just want to make something real.”