"I've always felt like a bit of an outsider," says Tri Angle label head Robin Carolan over the phone from his home base in New York City. He's talking about his early predilection for pop music, particularly the "weird" stuff. It was a preference that set him apart from his fellow writers at 20jazzfunkgreats, an influential blog that covered all sorts of music. "When I was a teenager, those were my two big obsessions: R&B and hip-productions, and then Warp. I suppose I never really saw any distinction between it, it just seemed to be one and the same thing. Often I would fantasize about Aphex Twin producing that album that Madonna apparently asked him for... because in my head that would've sounded amazing."

That outlook on things might have earned Carolan a few naysayers back in the blog days, but it's been key in shaping his unpredictable and often lauded imprint. Tri Angle isn't a dance label, and it's not a pop label; it's an outlet for wounded and woozy pathos, whatever the genre. "You know, I'm really emo about music, I get very emotionally involved in it," Carolan says. Whether it's Balam Acab's underwater lullabies or Holy Other's searing teen angst, his imprint reflects that tendency. Tri Angle situates itself as a cross between underground electronic music's poppiest sectors and its most experimental undercurrents; this is the label that released burgeoning pop stars AlunaGeorge's debut EP alongside Vessel's fractured-techno masterpiece Order of Noise after all.

Tri Angle began in 2010. "I get quite itchy if I'm not doing something new, and I just got bored and thought that a label was the next logical thing to do. 20jazzfunkgreats was known for being this blog that broke quite a few acts that went on to be pretty big or influential—it just got to a point where I was finding these people and decided that it would be interesting to be a bit more involved in what they were doing." In irreverent fashion, Carolan started the imprint with a Lindsay Lohan tribute CD in which artists like Laurel Halo and Oneohtrix Point Never put their own spin on the maligned star's oeuvre. "That was the result of me feeling like I had to get something out. Looking back on it... that release was a bit of a risky move." Even for so-called "poptimists," Lindsay Lohan's no-go musical career was difficult to swallow.

"That record was quite a statement that some people will buy into and think is really interesting, but then others will think it's just retarded and they won't understand it on any sort of level. It came at a time when people weren't talking about pop music the way that they do now." The release created a buzz, although Tri Angle's drudgy music and, yes, triangular imagery led to an accidental alignment with the nascent "witch house" movement. (Carolan has been disavowing the alleged connection since day one.)

Shortly thereafter Tri Angle began to take recognizable shape with releases from Balam Acab, Holy Other and oOoOo. While each artist came from a different place geographically, there was a throughline in the music of distilled sorrow and supple melodies. "I think there's something immediately quite feminine about pop music and R&B... I kind of tapped into my feminine side when I was younger, and I found something I could relate to," says Carolan, speaking of his early musical preferences. "[Femininity] is not something I specifically look for, because I'm always trying to find something different... [but] there's the kind of feminine, ethereal element to a lot of the music."

The initial trio of artists were also similar in their artistic development. Carolan seems to have a knack for finding young talent—sometimes from other labels—and helping it to grow into something bigger. "The artists that I'm working with, I'd like to think I'd be working with them for a long time. I don't really want to just do one-offs. If I'm going to work with someone and put a lot of time and energy into that, it's because I want them to be as amazing as I think they can be. Because I'm not really interested in my artists necessarily being a part of this weird indie ghetto where they all kind of just make music but they never really progress. I want everyone on the label to be successful as possible. Ultimately when you talk to artists, and they're being completely honest with you, that is what they want. They want to be successful because success means you get to do this for real. You don't have to worry about anything, aside from just making music and progressing as an artist."

It's the same story for Vessel. Bristol-based Seb Gainsborough had already released a few EPs of ghostly house and garage on left_blank and other small labels, but Carolan felt he had an enormous amount of untapped potential. "I read an interview with [Gainsborough] ages ago about different things that influenced him or inspired him. It was interesting because I couldn't really hear it in the music... I think when he was making his 12-inches, he was kind of reining himself in, whereas with the album it's a real exercise in just basically going nuts and doing what you want, experimenting." That album that Carolan refers to, Order of Noise, is one of the year's best. It pulls away from the R&B references of the label's past and goes somewhere darker and more jagged, aligning itself with Actress' cerebral fragmentation.

Order of Noise is one of the most obtuse things that Carolan has put out, but that's simply the other side of his taste coming to the fore. "When I find someone, it's for two reasons. One, I immediately respond to the music on a very emotional level... or number two, because it really confuses me and I don't quite get it. When I hear that sort of music I just get really excited about it. It's almost like a riddle you feel you need to crack, and that's definitely what I felt when I heard Seb's music. I felt confused but also very emotionally attached to what he was doing."

Carolan seems to be indulging this slightly more "confusing" sound at the moment. One of the more overlooked releases of 2012 on Tri Angle was Rhode Island producer Howse's Lay Hollow EP, five explorations of uptempo footwork-influenced rhythms drowned in field recordings and ambience. And then there is Haxan Cloak, a British sound artist whose nominally techno work cribs from eerie classical. Describing Haxan's upcoming album as cinematic and epic, Carolan explains that "it's a lot more electronic... there's still strings involved and there are these sort of weird organic textures that sort of mesh with these very jagged beats that he's made." He calls it an "intense record... I can't imagine Haxan Cloak ever making anything that's not intense."

2013 for Tri Angle is already largely mapped out. Carolan has a new signing, WIFE—a former black metal musician who makes weepy electronic music, but in Carolan's words, "something more poppy than what Tri Angle has generally released... [There's] an almost dark pastoral vibe about his music." Also planned are another Howse release and new Holy Other material. "I just feel the need to try and push it forward, and to make sure I'm not releasing the same records over and over again. There's going to be new Evian Christ material as well, which I'm pretty excited about because it's definitely not what people are going to expect from him. Kings and Them... was just him kind of finding a sound for himself."

Heading into the new year, the label now exists in a place that seems a long way from its beginnings. "[Some people thought] the Lindsay Lohan record was coming from a trendy place, when in all honesty it was probably the most uncool thing I could have done. Now it's a thing for underground indie musicians to talk about pop music, R&B and hip-hop... there's an indie band covering Rihanna, or talking about how Mariah Carey inspired them every other week." Suddenly Carolan's obsession doesn't seem so outrageous anymore.