There comes a time over the course of nearly every small publisher’s career when they question whether they can, or should, continue doing what they do. For Andy Brown, founding editor and publisher of Conundrum Press, that moment came in 2005, as his business was approaching the end of its first decade. “When my first son was born, I realized I was not making a living,” he says. Brown toyed briefly with the idea of selling the company and looking for work as the editor of a graphic novel imprint at a larger house, but in the end decided he’d be happiest working for himself, and forged ahead.

Another decade has passed and Conundrum is now one of the most respected and acclaimed graphic novel publishers in the country, and Brown is in a more celebratory mood. To mark the press’s 20th anniversary, he is releasing 20 x 20, an anthology featuring little-seen and unpublished work from 20 Conundrum authors, alongside a recap of the press’s 129-title backlist.

Brown founded Conundrum in Montreal in 1996. His first book was a handmade collection of work by his then roommate, Catherine Kidd. Encouraged by its success, he began producing books for other English authors, and soon found himself running an eclectic press. “Montreal in the mid-’90s was a hotbed of talent and artistic creativity, but there was no infrastructure on the English side,” he says. “This was the post-referendum climate for English creators, so everyone I knew was under-represented and I was trying to fill a void.”

Slowly, Brown shifted to a comics-specific mandate, as he realized the benefits of working in a genre with less competition than fiction and poetry. By 2011 he was publishing comics exclusively. That same year, Brown moved his family to Wolfville, Nova Scotia, a small university town outside of Halifax. “When I lived in Mile End in Montreal I’d walk out the door and bump into 10 cartoonists. But, that also can be a bad thing because you’re constantly distracted. And there’s still a strong comics community in Halifax.” He further refined Conundrum’s mandate with the launch of BDANG, an imprint specializing in translations of French comics for the English market. “I realized Quebec was a ghetto for these guys,” Brown says. “Some of them were published in France, but they were seen as the poor cousin there.”

Conundrum’s original Mile End home placed it nearby another upstart press, Drawn & Quarterly, launched in 1990 by Chris Oliveros. “Chris was all about the comics right from the start, and I was all over the place,” Brown says. “I thought, ‘If he can make a go of it and do such impressive stuff, why can’t I?’ When I moved into committing more to comics, I just needed to call Chris and say, ‘Where did you get such-and-such a book printed? What was the paper stock?’ Chris was incredibly generous with his information.”

Conundrum also has benefited from its relationship to D&Q in other ways. As the latter’s tastes and direction have changed, Conundrum has picked up several of its former authors. Combined with Brown’s other acquisitions, Conundrum is now home to some of Canada’s top comic talent, including Michel Rabagliati, Zach Worton, David Collier, and Joe Ollmann. “It’s been nice to watch Conundrum shift from a literary press publishing a few comics to exclusively publishing graphic novels, because that’s where Andy’s heart was,” says Ollmann. “As he built up a stable of really interesting cartoonists, you started to see the positive reaction from people when we were at shows in the U.S. or Europe.”

Brown says he’s most proud of “the number of artists who’ve told me they would have given up art if I hadn’t come along and encouraged them. I guess I just needed those couple of extra years to really get things going. – with files from Rachel Richey