If you ask Sean Raasch, lead singer and guitarist for the Milwaukee-based indie folk rock band Twin Brother, about the group’s days as a duo called Jackraasch, he’ll give you an honest answer. A surprisingly self-critical, brutally honest answer.

"I guess things were just getting a little bit stale with the Jackraasch thing," Raasch said. "We never did anything really legit, like an actual record, or did things the right way. I think that had a lot to do with why we thought we never got any headway with anything, so this whole Twin Brother thing is kind of a starting from scratch point to do it the right way."

So far, "the right way" seems to be working. Since rebooting the band and making the change to Twin Brother in late 2012, the band ­­– comprised of Raasch, drummer Tyler Nelson and bassist/violinist Lodewijk "Lodi" Broekhuizen – has made massive strides. The band released a self-produced, self-titled debut last May, as well as a music video – filmed largely at State Fair Park by locally based director Sean Williamson – for the song "Overwhelming" back in August.

Perhaps the most promising development from the past year, however, is that Twin Brother has recently signed with a record label, Tree Machine Records out of Bloomington, Ind. It’s an impressive step forward for a band that was a completely different group altogether barely over a year ago.

Seven years ago, Raasch and Nelson formed the pop-rock duo Jackraasch, an amalgam of the two members’ names (Jack is Nelson’s middle name). The band performed around the area, and even put together a CD, though the finished product, according to Raasch, left much to be desired.

"The engineering and recording was really poor I thought," Raasch said. "So it was just never done right, I guess, in a way that we would be really happy with and proud of. I guess that has a lot to do with why we never pushed it too much, because we weren’t happy with it. What are you going to do? But those are the decisions and things you go through that you learn from to help the next time around."

As the years went by, the band began to reassess itself, what it had accomplished and what its goals were. In the end, Raasch and Nelson decided some changes were in order.

"We wanted to try harder, try to reach out to other people, actually promote shows, reach out to press and finish a record," Raasch said. "Because obviously, this is what I’d like to do for a living, even if it’s just paying my rent and putting food in my stomach. It was just a decision to take things more seriously."

One change was a new name: Twin Brother, which serves as a reference to the tight synergy between Raasch and Nelson, as well as a kind of tribute to Raasch’s father’s twin brother, who sadly passed away several years ago.

Another part of the group’s reboot was the addition of a third member. Back when OnMilwaukee interviewed the band in 2008, Nelson noted that, "We will always be a two-piece … people were always asking to (play) the bass but that would just complicate things, and I think it would drastically change our sound and song structure." However, that was before the guys met Broekhuizen, a sound engineer at Club Garibaldi.

"He wanted to try recording us," Raasch recalled. "It wound up he started playing bass and violin on the recording, and now he’s an official member. Now we have a new name, and we’ve just kind of gone in a different direction."

Thus far, that direction appears to be up, aiming to stand out in Milwaukee’s crowded field of moody indie folk rock bands ("Maybe it’s the cold weather that makes people want to sing sad songs," Raasch jokingly hypothesized). Back in November, they released a new single, "Blood Money and Treason," on their website and Bandcamp page. Plus, there’s the recent aforementioned signing with Tree Machine Records.

"I reached out to a handful of labels, and he’s one of them that replied," Raasch said. "He’s a smaller label, but we’re a smaller band, and together I think we could probably help each other out a little bit. It’s really cool to know that there’s someone else fighting for you, trying to help."

Raasch doesn’t feel any added pressure from having the responsibility of a label. The only pressure he feels comes from himself, anticipating Twin Brother’s upcoming debut album release with Tree Machine, currently projected for a spring release.

"There’s more pressure in finally having a vinyl, in that whatever I do now is going to be on that," Raasch said. "But I’ve always wanted to have a vinyl of my own music, so I want to do it right."

Raasch is almost done writing the last few songs for their second album, and the band is scheduled to head into the studio, lock themselves down and start recording on Feb. 7. At this point in the process, he doesn’t have any particular changes or conceptual ideas in mind for the band’s sound for this new record, other than merely improving upon it.

"I’m always trying to outdo myself," Raasch said. "I don’t know what that is yet, but hopefully I can do it (laughs). I think that’s a key to a good artist of any sort: You’re never happy with what you did last."

And in the case of Jackraasch, while he may not be entirely pleased with that period of time with the band, he certainly doesn’t regret it.

"I’ve had some of my best moments in my life playing shows with Tyler as Jackraasch. I learned so much from it. You can only be who you are presently from the things that you went through and what you’ve learned. It was just kind of like school, and now I feel like I’m attempting to graduate and put that stuff to use. But I don’t look at it like, ‘Man, we sucked’ or anything like that. I thought our songs were really great. I just think we’re growing; that’s all."