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"Learning to make guitars for the second time made me really think about it," he says.
It didn't take long to pick up some high-profile clients. Hill built a seven-string for singer Matt Heafy from the hard rock band Trivium and a double neck for Megadeth's Dave Mustaine. But while he was cranking out guitars, his business partner wasn't paying the bills.
"He wasn't helping me and we weren't getting anywhere and we were losing money," says Hill. "I couldn't pay my employees and we got behind on our rent. If the investor was there side-by-side with me grinding it out, I would have stuck with it."
Hill managed to survive for a while by building guitars on a subcontract basis for Dean Guitars. But when the orders from Dean stopped, he was out of work. He called the company, asked about full-time employment, and got hired back. So in 2007, he shut down Hill Custom Guitars and moved to Tampa to work for Dean again.
"I set up their woodshop from scratch," he says. "They had the facilities to be doing 1,000 guitars a month. But when I was there, they were only selling 15 or 20 a month, and making six or seven artist guitars a month. I knew it wasn't going to last, because I had been doing that many guitars in Cleveland."
Still, it gave him an opportunity to learn the manufacturing and engineering side of the business, and work with some high-end software. Hill finally left when he realized that "there was no future for me to do anything other than make some rich guy richer."
When he moved back to Cleveland about two years ago, Hill's first priority was to get stabilized financially. He took on work like building a 17-foot, $15,000 custom entertainment unit. "It was a crazy job, but it helped me get caught up on some bills," he says.
The stress was overwhelming. His old business partner sued him, and he lost the right to use the Jon Hill logo on his guitars. His wife left him. But he persisted, restarting his business under the name Bootleg in 2010.
"I've essentially been bootlegging my whole life, so the name fits," he says. "But really, it's not about the name, it's about the quality of the product. And Bootleg is a whole new attitude and vibe. We're focusing on our own cool designs for a performance-level, badass guitar."
Since relaunching, he's built a guitar for Godsmack's Robbie Merrill. And Erik Porter, the bass tech from the Dave Matthews Band, recently called Hill to ask him to make a five-string fretless for DMB bassist Stefan Lessard.
Skid Row's Scotti Hill first heard of Jon Hill guitars years ago, after meeting Cleveland rock guitarist Billy Morris, who was on tour with Quiet Riot at the time. Morris was playing a Jon Hill guitar, and Scotti wanted one.
"He built me a guitar back then and it was really nice. but not exactly what I was looking for," Scotti says. "The next one he did was the Generator. That's the one I play every night now."
Earlier this summer, he asked Hill to make him another guitar and even flew to Cleveland to observe the process.
"I watched him take a piece of maple and mill it," Scotti recalls. "That thing was harvested a hundred years ago, probably. He walked me through the process and that became the guitar I call the Sidearm. I told him I wanted something like a military officer's sidearm — something not normally used, but an officer generally carries. It's very, very special. As a player, you can tell when you pick up a guitar whether it will take years to break in. But this guitar had magic right out of the box."
Scotti says he couldn't believe how effortless the process was.
"Jon is very nonchalant and will casually carry on a conversation while shaping the neck," he says. "He let me do some filing, and I practically destroyed the thing. It just comes naturally to him."
Jon Hill enjoyed spending time with the Skid Row guitarist too.
"We went to the Rock Hall, and one night I took him to the Foundry, Billy Morris' club, where he jammed on a couple of songs."
Hill has also started producing custom paint-job guitars. Robb Ortel, an airbrush artist who works for the custom bike shop Orange County Choppers in New York, has painted a few of them.
"I build the best guitar on the planet, but unless you put a lipstick paint job on it, it's not worth anything," Hill admits. "More people are sold by the aesthetics than the instrument value."
Hill has also hired longtime Cleveland musician and promoter Rob Stevens to help him come up with new business ideas, including guitar accessories. They hope to put out a calendar next year that will feature Cleveland-based models holding Hill guitars, like the Ridgid Tool calendars.
Last week, Hill was busy moving his shop into a bigger workspace near Prospect and East 40th Street, where he'll share space with Paul Mills Custom Woodwork, a local cabinetmaker who has done work for the Barley House and other area bars and restaurants. Once he's increased production, Hill hopes to spur international sales to places like Japan, where he has an agreement with Labrea, a distributor that's signed on to carry two models, the Generator and the Burd.
Hill even envisions offering guitar-building classes in the new space. Yet despite all this, he knows he's still an underdog in the guitar-building world.
"I'm up against Fender and Gibson, who both have deep pockets," he says. "The odds are stacked against me. It wears you down, for sure."
But Hill remains true to his artisan roots.
"I just like watching people play my guitars," he says. "That's impressive. Sometimes I build beautiful guitars that people don't even play out. I don't blame them. If I spent $5,000 on a guitar, I wouldn't want to take it to some blues jam and sweat all over it either. I prefer if people play them. They can even beat the shit out of them if they want."