If you happen to be curious about the person responsible for releasing beautiful acoustic music under the name Gambles, the best and most perfunctory explanation can be found on the Gambles website: “Gambles is Matthew Daniel Siskin. Gambles writes songs and words and mostly moves the way he needs to. Gambles will be releasing things soon. There is no pattern to any of this.” After talking to Matthew Siskin — a man who also does double duty as the creative director of Designedmemory (the studio behind Beyonce’s fancy website and Tumblr page, among other beautifully designed things) — the relatively no-nonsense description of his work as a singer and songwriter is very much in keeping with his creative ethos. Under the moniker of Gambles, Siskin writes songs that are both minimal (his own howl-y vocals accompanied only by acoustic guitar) and harrowing (songs about heartbreak and loss that are equal parts beautiful and wince-inducing). His earliest songs to make a splash on the Internet — “Trust” and “Safe Side” — were actually some of the very first songs he ever wrote. After starting to fool with songwriting back in 2012 as a way to relax and make sense of what was happening in his personal life, Siskin was genuinely surprised when Gambles quickly took on a life of its own. In October he’ll be releasing his debut album, Trust, on his own GMBLS label. In the meantime, he’s playing shows, writing new songs, and basically just riding the wave. I called him up to discuss.

STEREOGUM: So, for people who don’t know about you …

SISKIN: You mean everybody. [laughs]

STEREOGUM: Well, I think some people do know about you. Not only because of your music, but also because of your design work.

SISKIN: Right, they know versions of me.

STEREOGUM: At what point did you start to think that maybe you should actually record your songs?

SISKIN: It was really about eight months ago, last December. I had talked about doing it and I knew I wanted to do it and everyone had been asking me at that time what I was up to, since I had just come out of a very weird period in my life, and I’m like, “I made a record! I made a record!” And in reality I hadn’t recorded or written a thing. And they’re like, “Oh cool, can’t wait to hear it!” And I’m like, “Oh yeah, totally!” And then summer came and I just started spending a lot more time sitting down and searching a bit for what I wanted to sound like … and I just didn’t want to be another fucking cool band. I feel like there’s so many “cool” bands doing “cool” things and everything is just so “cool” now. I just thought, if I’m going to do this I want to find my own self in it that feels genuine and real, even if people don’t like it. I just want it to sound like me. Like, if someone I know hears it they can be like, “Well that’s Matthew,” and you can always hear my voice in it. So I spent a few months just sitting at a table with a lot of weed, just recording myself and listening to myself until I just kind of found something. I had this moment of, “Oh, that feels like something,” and it’s really distorted, really crackly, and really reverbed out, and it’s only me with just a guitar. It was the first time anything felt like anything … and from there I just kept going.

STEREOGUM: Wow, so was it a difficult process putting these songs together?

SISKIN: Umm, difficult how?

STEREOGUM: Difficult in two ways, I suppose. Difficult in the sense of actually doing the recording and figuring out what you’re gonna do with them and all that. But also just content-wise, I mean the songs are really pretty harrowing.

SISKIN: Yeah, thanks! I really appreciate that. I’ll be totally honest, the recording part was effortless to the point where I realized — after I’d done these home recordings I ran them to Nick Vernhes at Rare Book Room and I was like, “Dude I did these recordings!” And I played them for him really loud and they were really distorted and he was like, “Dude!” And he loved it. Throughout this process he has been my best friend and my barometer for things. We got really drunk that night and ended up going downstairs to his recording studio and I recorded “Trust” — well I just sang “Trust” and that’s one on the EP and on the new record. We did it in one take. I realized then that I could just freestyle a bit. You know, I read a lot and I write a lot and I think I have this way … I can bullshit and I can have fun and I’m always talking — I’m “that” guy and I can’t help it. But with music it kind of helps that my imagination is so silly that I can just close my eyes and basically just do it. At the time I was pretty torn up about a lot of stuff so I was able to say things in the songs … it was like sitting down and talking to someone, but singing.

The process was just me being in his amazing recording studio and using one channel, one take, no overdubs. You just sing it and that’s what happens. At one point I tried to do the opposite — being in a live room like, “We’re going to do a guitar take and then a proper vocal take,” and that failed miserably because it just didn’t have the right feeling. I realized the only way this was going to work was if I repeated myself. So I got kind of drunk again, went back to his house and literally sang like 10 songs in a row, and then I went home and worked some more and actually wrote stuff and came back with more … and that was just sort of the process of finishing the record. Just give me a microphone and as long as my mood is right I can do it. A few of the songs on the LP that’s gonna come were recorded here at my house. You can actually hear on one song — if you have really good headphones — you can hear the 6 train underneath me. I tried to time it so I’d miss the train sounds but it comes in frequently and I live on Bleecker Street. As for where the songs come from, you know, I was doing it because I needed to do it and because I needed to say all this nonsense and try and make sense of it. A lot of it kind of makes me feel a little bit selfish because there’s an actual human person — a person who was a big part of my life — involved who’s alive and has to live with this shit and I’m putting this out into the world. But I think she kind of understands it. She is super strong, and we’ve also met up and talked about all of these things. When I made the video for “Trust,” we had dinner and I said, “I’m doing all this stuff,” and she’s like, “Yes, you are.” So it was cool. Still, I’m an asshole and if she told me not to do it, I probably would have done it anyway, but luckily she gave me a blessing. She’s a lover of music and I think she’ll be OK with it. The fact that whatever we experienced, whatever that was, whatever that meant, is now in this little thing that I made … it’s a nice thing. Those are my favorite records because it’s just true. And I think people relate to that because it happens, because I think my situation happens to a lot of people all the time. Fucked-up things happen to people and you make the best of it. You make art about it. You make sense of it.

STEREOGUM: How is it to perform these songs?

SISKIN: It’s intense. It’s super intense. If you’re in a room of people who are talking, I’m not going to sing these songs. I refuse to because they’re kind of really dear to me. It happens though. I was in Chicago and I got hate mail on Facebook. People were like, “Yo man, you’re a douchebag, gotta earn respect!” And I’m like, “You know what? Fuck you.” These are my songs and I’m not doing them because I want you to like me, I’m doing them because I needed to do them … and if you don’t like what I’m doing or you feel like I need to pay my dues by singing them to a loud room of people not paying attention, well, that’s just not the artist that I am. So it can be challenging, but at the same time it’s awesome and it’s emotional. Like the first time I sang them I was trying not to lose it and get choked up. It’s like reading a speech at a friend’s funeral. You are prepared to get up there and do this whole thing, but when you actually start trying to say this stuff … I mean, a song like “So I Cry Out” … I’m way past the emotions of what that song was, but as soon as you sing it it’s like watching a film or something — for me at least. I just immediately am back there and trying not to lose my shit and just get through the song, and that tells me that I’m doing right by me and I’m not just going through the motions. It’s a weird thing, but it just is what it is. It’s weird sometimes to be performing this very confessional material.

STEREOGUM: There’s a real emotional intensity to what you do — particularly live — that people really respond to. In some ways it kind of reminds me of Majical Cloudz.

SISKIN: I met him the other night actually! I love his record.

STEREOGUM: Yeah, I mean I think the music is different, but he spent a lot of time trying to figure out why he was writing those songs and also why people were resonating with it so hard. And I think it comes back to those same things — there’s something really pure about it and the sentiment is really super genuine.

SISKIN: I’m really glad you mentioned Majical Cloudz because that’s … I mean, I’ll be honest: I saw him play once and I hated it. I was like, “Fuck this is awkward.” And then I realized that those are all the feelings I love, and I felt challenged by what he was doing. Then I listened to the record and was like, “Oh my god.” I think they’re one of the very few bands doing that can pull this off. Onstage they’re challenging people and it’s lyrical and it’s simple and it’s so direct. And I think right now people are craving that because nowadays everything is so produced. I like the idea that the tide might be changing a little … that people are getting into things that are simple and bold and individual and pure … not even pure, because what’s pure? I mean, I’m not pure, I’m using my life experiences to sell music, but the motives are still pure, but anyway … I love Majical Cloudz.

STEREOGUM: Stereogum is going to premiere “So I Cry Out,” which such a beautiful but incredibly heavy song. It deals not only with the end of a marriage, but the loss of a child during a pregnancy. Why this track?

SISKIN: “So I Cry Out” is one of those songs that — unlike “Trust” or “Safe Side,” songs that hint at things and are kind of vague — this song is probably the most direct and sincere kind of thing I could possibly say to her, the girl that I’m talking about and the situation that we were in together. “Safe Side,” was about all the things that kind of drove me crazy and ‘Trust” was about leaving her. This one is just like, “We’re just two fucking kids who had fucking bad luck.” We both grew up in horrible circumstances where basically you grow up in like an hour because of this one thing that happened and then you’re never the same … and it’s sad that it happens. I don’t know, it’s one of those songs I wrote before anyone knew about me … I put it online and my friend texted me and she’s like, “Are you Gambles?” and I was like, “Yeah.” And she was like, “Dude, I just had the best cry to your song,” and then I got another text and it was like, “Dude this song just cut me open, and it’s so amazing and so beautiful and so sad.” So, that’s the story with that song.

STEREOGUM: Some people know you from your other work as creative director for Designedmemory, which is a very successful business. How do you strike a balance between doing music and your design work? It must not be easy.

SISKIN: The design stuff I do, I love so much. Actually, everything I do I really love. I’ve always told myself that I’m only going to do things that I love and because of that I’ve never had a job that I hated going to. Fortunately, and I mean very fortunately, my circumstance is very lucky and very unusual. That I found this stuff I love to do and that people hire me to do it … it’s such a crazy blessing. But right now the balance is definitely tricky. I want my clients to know that I’m there for them, and that I’m here, and I can still keep up with my responsibilities, but I’m also creating this other world which … it’s kind of like having an open relationship and saying you’re dating a girl and you also date another girl but it’s like, “It’s okay, I still love you.” The good thing is that even when I’m on tour all I need is Wi-Fi and I can still work. Traveling between shows I have so much time to work, it’s almost like I’m more available than I am when I’m in NYC, it’s just not face-to-face. But just mentally, it gets a little stressful, and I’m lucky that I have an amazing person in my life who helps me stay centered and balanced and stuff and there are certain days where I’m like, “Fuck! I have like these 25 things to do” and I’m doing this record, and playing these things and thinking about these tours and I want to go on tour but I can’t go on tour for like six months and still do my other job … . and the reality is everything I do is funded by my design work, because I started a label — an imprint — so it’s all by me and I own all of it. So it’s me putting myself on tour and I don’t want tour support from anyone, I don’t want help, I don’t want advances, I don’t want any of that stuff that I think maybe hurts bands later on because all of a sudden they owe everyone everything. It’s just a funny dance. But also I like it because it’s challenging, and I can’t complain about it. It’s a super-challenging fortunate situation, I’m just trying to keep it straight as best I can.

STEREOGUM: Being able to do it yourself it does afford you a certain kind of freedom that is pretty amazing.

SISKIN: Yeah I just want to milk it for as long as I have it, maybe I go with a label for the second record, maybe somebody steps up and actually wants to partner with me. Right now I work with Secretly Canadian — I have a distribution deal with them and they’re behind me and it’s really great and helpful with my little imprint. And the internet! Maybe if things went well for Gambles then maybe I don’t need a label. I also want to release written things, I want to make books, I want to make things, I want to release my friends’ writing. I like the idea of constantly releasing art and music. It’s almost 2014! Fuck. I love using all these different tools and finding new ways to operate. There’s so much to do. So you know … I’m just hungry to keep going.

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Listen to “So I Cry Out” from Trust:

Gambles Tour Dates

10/07 Los Angeles, CA @ School Night / Bardot @
10/11 Baltimore, MD @ The Metro Gallery*
10/12 Brooklyn, NY @ The Union Pool*
10/13 Boston, MA @ Great Scott*
10/16 Philadelphia, PA @ Boot & Saddle*
10/17 Washington, DC @ Black Cat Backstage*
10/18 Pittsburgh, PA @ The Club Café*
10/20 Cincinnati, OH @ The Northside Tavern*
10/22 Cleveland, OH @ The Beachland Tavern*
10/23 Detroit, MI @ The Magic Stick Lounge*
10/24 Milwaukee, WI @ The Frequency*
10/25 Minneapolis, MN @ 7th Street Entry*
10/26 Chicago, IL @ Schubas*

@ w/ Jagwar Ma
* w/ Those Darlins

Gambles will release Trust on his own GMBLS imprint on 10/1.