If you hadn’t heard of Milwaukee indie-folk trio Twin Brother prior to this summer, not only do we forgive you for the oversight, we’re ashamed to admit we were right there with you. It wasn’t until the material that would eventually wind up on the band’s great sophomore release—the tragic and identifiable acknowledgement of youth’s exodus, Swallow The Anchor—took shape that Twin Brother found itself on the receiving end of some well-deserved local praise. With his band’s standout record making frequent appearances on an array of Milwaukee “Best Of” lists, Twin Brother singer/guitarist Sean Raasch is finally enjoying some late-blooming fruits to his years of labor.

In addition to his songwriter responsibilities, Raasch was also given the entertainment books to historic Bay View bar and venue Club Garibaldi this summer. Friday night, his two roles will unite, as the Twin Brother bandleader will appear on Garibaldi’s stage as part of a bill with some of Milwaukee’s (other) most talented singer-songwriters. Before he closes out his most accomplished musical year to date, Milwaukee Record asked Raasch about Twin Brother’s recent acclaim, his booking mentality, and what to expect during the December 26 songwriter showcase.

Milwaukee Record: Twin Brother turned in a pretty great 2014. Swallow The Anchor was on a few Best Of lists in town, including in our top 10, and lists ShepEx and JS put out. How does it feel to get all that local love, and has it helped bring more attention the band’s way?

Sean Raasch: It feels great. It’s really nice to know that people noticed the work we did this year with Swallow The Anchor. I’ve been working hard with music for over 10 years, and it’s taken just about that long to be noticed. You can imagine now that it’s finally happening exactly how good it feels. It’s proof that hard work and not giving up can turn into something. Now, it’s not an MTV award but I’ll take it! We have been getting a lot of hits on our Bandcamp. It hasn’t really turned into sales that I can see yet, and we haven’t  played a show since, so time will tell if  the lists really help. Overall, it’s very difficult for anyone in a band playing the type of music we play. Old Earth moved to San Francisco, if that gives you an idea of how difficult it it can be here.

MR: As far as the album itself is concerned, why do you think people have gravitated to this one more than the Twin Brother debut or your and Tyler [Nelson]’s work with Jackraasch? Is there a different focus this time around?

SR: I think the quality of work is a lot stronger. I mean that in every way. From the production to the song structure to the way I sing, everything has improved a lot. That is something you can’t lose either, which is great. We’ve reached a level that only allows for strong progression.

MR: I know you’re writing some solo stuff, but how else do you plan to continue the momentum of Swallow The Anchor?

SR: Solo stuff is fun but it’s more of a hobby than anything else. When I record solo material it turns into a practice regarding the art and many sides of songwriting. Twin Brother plans on continuing to push the latest album in areas that have not heard of it yet. It makes no sense to stop playing the album when only Milwaukee has really heard it. The Midwest will be a focus of ours in 2015—playing in cities like Madison, Chicago, Minneapolis, and more. While we do this, we plan to write more and hopefully have another album ready by the end of the year. I just have too much material constantly flowing out of me to wait longer than that.

MR: Explain this songwriter’s showcase the night after Christmas. It’s a group with eclectic styles: country, rock, folk. How did you select the performers, and how long will each play?

SR: Each songwriter will perform around 15 to 20 minutes. There are no real restrictions, so that’s just a ballpark. We have lots of people preforming, including a couple comedians, so no one-hour sets. My idea with this concert was to basically get a group of very talented people together for a fun night. [There will be] no bands, so it has the opportunity of being more relaxed; no carrying huge amps or drum kits around. Everyone I asked to play—more than just being talented songwriters or comedians—are just great and wonderful people. I really enjoy the company of everyone on the bill and that, to me, is a perfect night.

MR: The site of the show is no big surprise, with you booking there and all. When did you take over Garibaldi’s books? What have been some of the major challenges taking over the musical direction of a venue? What have you learned so far?

SR: I started officially booking Garibaldi in early summer. I really enjoy it, but there are challenges that come with the territory. It’s easy to fill dates, but it’s difficult to fill the dates with acts that bring good crowds. The goal is to have a successful Friday and Saturday every weekend. Learning how to make that happen has been a complicated process. Just because I like a band doesn’t mean people will come watch them. Unfortunately, that’s the name of the game in the booking world. The goal is to find a nice balance. I really being able to give the local scene here a step up venue-wise, and I’ll like having the opportunity to give smaller bands a chance to prove they can playing bigger venues. I try to be a booker I would like to work with as a musician on all levels.

MR: More specific to the types of acts you’re trying to book, what are your plans for it going forward? I’ve said it a lot to anyone who will listen, but I really like Garibaldi as a comedy venue.

SR: I want to keep doing the comedy for sure. I think it deserves just as much attention as local music. We have some hilarious comics here that no one even knows about. That seems like the norm here in all aspects of entertainment, but it’s partly my responsibility to help as much as I can to get that stuff off the ground. Most are all too often never given a chance. We all need to do what we can to make talented locals gain the attention and respect they deserve.

Sean Raasch will play as part of the Christmas At Club Garibaldi songwriter showcase Friday, December 26. Marielle Allschwang (Altos, Hello Death), Jordan Davis (Space Raft), Mark Waldoch (Celebrated Workingman), George Anachev (Absolutely), Joseph Huber (ex-.357 String Band), Connie Ward (Buildings On Buildings), and comedians Josh Ballew, Lisan Wood, and Phil Davidson will also perform. The show begins at 8p.m. and all proceeds benefit School Of Rock and Girls Rock Milwaukee.