Bill and Lisa Roe in their Portage Park home, which also serves as headquarters for Trouble in Mind Credit: Lucy Hewett

On a winter day in early 2014, I was browsing at Permanent Records when the music on the shop’s sound system caught my ear—terse Krautrock-­inspired grooves topped with buoyant organ licks that reminded me of a late-60s Walter Wanderley bossa nova record. I’m sufficiently jaded that I rarely ask a record-store clerk what’s playing, but this time I couldn’t help myself. Bill Roe was behind the counter, and though I only knew him by name, I also knew he was well established in Chicago’s garage-rock scene—he and his wife, Lisa, played together in the band CoCoComa, and in 2009 they’d founded a small label called Trouble in Mind. He told me that the music I was hearing was from a new record by Swiss duo Klaus Johann Grobe—an unfamiliar name to me at the time—and that Trouble in Mind was about to release it.

This news caught me by surprise—as far as I knew, Trouble in Mind was a garage-­rock label. The Roes had launched it by releasing a CoCoComa single shortly after the birth of their first child, Veronica “Ronnie” Moon. In the final few months of 2009, as they ramped up their schedule, they put out half a dozen more singles by bands in their orbit, all of whom had garage rock in their DNA—including the Fresh & Onlys, Ty Segall, the White Wires, and Chicago’s own Tyler Jon Tyler.

The Klaus Johann Grobe record was a long way from three-chord caveman trash, though, and in light of that accidental discovery, I figured I should give Trouble in Mind’s output a proper hearing. In the two years since then, the label has continued to diversify its roster, adding the likes of Portland art-rock band Alto!, who are inspired by guitar music from Lebanon and the Sahara, and San Francisco fingerstyle guitarist Chuck Johnson, who sculpts moody electric soundscapes.

During that time Trouble in Mind has also become a full-time gig, at least for Bill—in September 2014 he quit his job at Permanent to devote himself to the label. (Lisa works full-time at the Bucktown-Wicker Park branch of the Chicago Public Library, though she says she usually checks Trouble in Mind’s e-mail each morning—right after getting out of bed at 6:45 AM.) The Roes have graduated from releasing only singles, and their catalog of roughly 120 titles now includes more than 50 albums. Their operation has grown organically, expanding within its means—the same MO followed by many of the best indie labels in Chicago, including Drag City and Bloodshot. Trouble in Mind has introduced several artists who’ve gone on to greater fame elsewhere, among them Mikal Cronin (who now records for Merge) and Morgan Delt (who’s about to drop his debut on Sub Pop).

When the Roes started their label, each sold-out single would fund the next one, and for a while they were pretty happy with that arrangement. They released all their seven-­inches in sleeves with identical artwork, so that only the varying colors of the center labels distinguished them. They also restricted themselves to “trash” vinyl—made from multi­colored scraps—or plain black. When scene elder Brian Costello profiled Trouble in Mind for the Reader in 2009, Bill explained the thinking behind this: “We’re trying to reduce the collectibility,” he said. “We want to keep these records in print, something to enjoy instead of resell a month later.”

Today Bill isn’t sure Trouble in Mind had an overarching vision in place at the beginning. “I wouldn’t say there was ambition, like a grand scheme, necessarily,” he says. “We just wanted to be a singles label at first, and that was probably a little shortsighted.” The label took the plunge into LPs in 2010, after Bill noticed several unreleased songs on the My­Space page of French band Limiñanas, who’d already released a single on Trouble in Mind. The group were working on a full-length album, as it turned out, and later that year their LP became the first in the TiM catalog. “You realize,” says Lisa, “that as much as we love singles and the idea that it’s two songs you just want to play over and over, having ten songs that you want to play over and over is even more enticing.”

A recent sampling of Trouble in Mind's multifarious offerings: Alto!, <i>LP 3</i>; Chuck Johnson, <i>Velvet Arc</i>; Invisible Astro Healing 
Rythm Quartet, <i>2</i>; Jacco Gardner, <i>Cabinet of Curiosities</i>; Klaus Johann Grobe, <i>Im Sinne der Zeit</i>; Matchess, <i>Somnaphoria</i>
A recent sampling of Trouble in Mind’s multifarious offerings: Alto!, LP 3; Chuck Johnson, Velvet Arc; Invisible Astro Healing
Rythm Quartet, 2; Jacco Gardner, Cabinet of Curiosities; Klaus Johann Grobe, Im Sinne der Zeit; Matchess, Somnaphoria

At the time Bill was working for Chicago Independent Distribution (the rebranded U.S. distro arm of Southern Records), which had recently opened Logan Hardware. His job dealt mostly with production, and it didn’t prepare him to handle every facet of running a label­—keeping Trouble in Mind on the rails was a learning experience. He talked as much as he could to friends who worked at other labels. “I asked a lot of stupid questions,” he admits.

In 2013 Trouble in Mind released Cabinet of Curiosities, the debut album by Dutch psych-pop singer Jacco Gardner, and it succeeded beyond anything the Roes could’ve hoped for. (It’s gone on to be the label’s biggest seller, moving 10,000 copies so far.) This raised the profile of Trouble in Mind, and soon it was facing greater demands—the Roes suddenly found it more difficult to keep music in print, maintain a steady release schedule, and satisfy the growing expectations of their artists. For the first time, the label began hiring PR and marketing firms to help with some of its records. “Once you start putting a little more real money into it, that’s when the bottom line starts mattering, I guess,” says Lisa.

Bill insists he never imagined that the label would take off the way it has. “It was never a thing where I was like, ‘Someday this is what I’m going to do for a living,’ ” he says. “It was really just sort of stumbling into it, with the success of the label—and trying to juggle that with a full-time working job.” In 2010, shortly after leaving CID, he’d started at Permanent, but before long his responsibilities at Trouble in Mind forced him to reduce his hours and go part-time, and in 2014 he had to quit.

Trouble in Mind’s growth as a business has been impressive, but the broadening of its aesthetic is what’s really thrilling about its evolution. Bill cites the full-length debut of Klaus Johann Grobe—the record I heard him play, which came out in spring 2014—as one of the first releases that definitively departed from the label’s comfort zone at the intersection of garage, psych, punk, and pop.

Trouble in Mind was building a hard-core fan base—one that was willing to trust the label’s sensibilities even as they evolved. “We have a pretty dedicated mail-order following of about 150 people that will buy everything,” Bill says. “I think that’s awesome and a testament that we’re doing something right—that people still follow us and trust our opinions and tastes.”

“To Bill’s credit, he has very deep knowledge of music, and I think that has allowed us to be brave sometimes and trust that what we’re hearing is valid,” Lisa says. “Ultimately, the label is sort of a reflection—if you came and looked at our record collection, it’s not just garage rock.” Since the Klaus Johann Grobe album, Trouble in Mind has put out records by jazz-influenced Ethio-rock band Invisible Astro Healing Rhythm Quartet, industrial-­flavored noise-pop act 31Ø8, and atmospheric dream-psych artist Matchess (aka Chicagoan Whitney Johnson), among others.

Bill has a rabid curiosity about new music, and it hasn’t faded just because he’s no longer being exposed to fresh releases at Permanent. “When I was working in a record store, it was lot easier to keep my ear to the ground and keep on top of things, but I think I’m still in a rhythm,” he says. “I’m kind of an insomniac, so she’ll go to bed at ten, fall asleep, and I’m up. I’ll either watch Netflix or I can go dink around on the computer and go to music sites and listen to stuff. I’m glad I haven’t gotten to the point where I’m just settled into a rut—’This is what I listen to.’ I’m always pretty restless, and I’m always feeling the need to keep listening.”

Though Trouble in Mind continues to branch out, its heart and soul is still in the garage—that is, ultracatchy rock with a 1960s feel. The Roes have an uncanny talent for uncovering a seemingly endless procession of little-known acts—the Paperhead, Doug Tuttle, the Butterscotch Cathedral—who make incredibly hooky music. The fact that Trouble in Mind has only done two reissues in its history—one by Del Shannon of “Runaway” fame and another by UK indie-pop band the Dentists—can be seen as a testimony to the Roes’ skill at finding active artists doing great things with classic sounds.

The Roes live in a Portage Park home they bought in 2013, which houses the label too. They became a family of four with the birth of their son, Arthur Lee, in spring 2012. Bill and Lisa admit that running the label and raising two kids can be overwhelming, but they seem remarkably centered—and they have an inspiring rapport that makes the challenge easier to face. They’re so thoroughly in sync that they don’t just finish each other’s sentences—they both seem to know in advance what the other will say. “There are terrible days in life sometimes,” says Bill. “If one of us sees the other is stressed or upset, the other can step in. Somehow it’s this weird dance, and we can each take care of business.”

“I can’t imagine if Bill was married to someone who wasn’t involved with the label,” says Lisa. “There have been times where it’s literally been like, ‘We have this amount of money—we can either get records or pay our mortgage on time,'” and we look at each other and it’s, ‘Well, we gotta have those records.’ And so we’ve got to pay our mortgage a little late that month.” The couple have also decided that they have to agree on everything they release. “That’s the rule,” she says. “I’m the worst liar on earth, the worst pretender, and I can’t commit myself to something that I’m not 100 percent on board with.”

“I’ve rallied hard for a few things that she’s ultimately like, ‘I’m just, you know, I’m not into it,'” explains Bill. “It’s broken my heart a few times, but it is what it is. I mean, ultimately, she’s got golden ears.”  v