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Trey Strait as his manager, he decided to leave Houston and go for it in Nashville.
"Trey had some great connections in Nashville, and we eventually got what we thought was a decent deal with Midas Records, a sizable indie label, so I packed up and moved to Nashville," recalls Wolfe, who returns to his former hometown Friday night.
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Wolfe spent most of 2006 writing and working on his album, and had it recorded and a radio single selected when Midas (which also had Emerson Drive on its artist roster) folded in early 2007. He describes what happened next as a very hard time.
"I spent 2008 and 2009 basically writing and struggling," says Wolfe. "And what really hurt was that in all the confusion and letdown, I lost the touring momentum I'd worked so hard to build. Like I said, I went through the Nashville meat grinder, and it didn't feel so good."
Working as a commodities trader for British Petroleum, Wolfe originally moved to Houston in 2003. He almost immediately began singing at Ryan Huie's open-mike nights at Bissonnet dive bar Kay's Lounge.
"I was rooming with Hayes Carll for a while, and I definitely had the bug to sing and try to write songs," Wolfe says. "They took me in with open arms at Kay's, and it was a pretty nonthreatening environment to learn in. And that's where I met John Evans, who produced my first album."
Wolfe remembers seeing Evans sitting at the corner of the bar, watching the open-mike performers. Evans approached Wolfe as he was coming offstage.
"Here comes this tall rock-star-looking dude and, in that Elvis voice of his, he says, 'Hey, you got enough songs to make a record?'" Wolfe says. "The next thing I knew, we were doing it."
The result was 2005's Almost Gone, a hardcore honky-tonk record with a lot of Garth Brooks and George Strait mojo. Wolfe quit his BP job and took his act on the road, developing a good following in Texas and his home state of Oklahoma.
He became a regular at Tulsa's historic Cain's Ballroom, and played a New Year's Eve 2006 party for George Strait when another act had to cancel at the last minute. Soon, Wolfe found himself living in Nashville and immersing himself in the whole co-writing scene that makes Music Row run.
"The business side of Nashville can be pretty rough, but I can't say enough about having been there around some great writers for a few years," he notes. "I've gotten to co-write with some greats like Tim Johnson, who wrote Mark Chesnutt's big hit 'Thank God for Believers.' Mickey Newbury, one of the greatest writers ever, brought Tim to Nashville. I made some great friendships in Nashville, and now I have a little team I can count on as far as songwriting and recording goes."
Wolfe name-checks James Dean Hicks and producer Buddy Cannon's daughter Marla Cannon-Goodman as writers he prefers to work with. Both have written No. 1 country hits and have songs on his new album, It All Happened in a Honky Tonk.
After he hit bottom in Nashville, light finally appeared at the end of Wolfe's tunnel in the form of LEX Music's Lex Lipsitz, who describes himself as the singer's "manager, producer, life coach, drinking buddy and good friend — Jon's quarterback calling the plays."
"Jon and I became friends during his Midas Records days, when I pitched him songs that he cut for that record that never saw the light," muses Lipsitz. "We kept in touch over the years until his recent split with his management. During that window, it just felt right for us to finally work together. We've always seen eye to eye on his overall vision for this record."
Lipsitz says It All Happened in a Honky Tonk, a tightly played package of whiskey-soaked twangers about beer joints and the people who frequent them, represents Wolfe's "greatest hits of the last four years." After what Wolfe went through in Nashville, his handler sees him as a more confident, maturing artist coming into his own versus the 2005 debut.
"No offense to Jon," Lipsitz demurs, "but he wasn't ready for this a few years ago. It takes years to hone your craft, sound, image and message, but he's finally grown into the artist he is now. All he needs to do is get out there and shake a million hands if he wants to sell a million records. He's definitely ready, determined and willing to put in the work."
Rather than try to shop the new album to labels, Lipsitz and Wolfe decided to release the album themselves, and do it quickly. The official release date is September 7, but Wolfe will be selling it at Blanco's Friday.
"We want to build his brand and business up before we shop it," Lipsitz explains. "I want to make sure that a label buys into a working product before taking a gamble. They need to understand what it is, who's buying it and why people love it. That way we have the leverage when being shopped.