The Last Frontier: Skyler Insler on Alaska, Alphaville, and The End of DIY

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Photos by Jane Bruce

Skyler Insler’s relationship with Brooklyn started long before he moved here. His family, Italian by origin, lived in Coney Island and Bushwick until they didn’t, decamping for New Jersey somewhere in between then and now. And in high school he used to come to Williamsburg with friends, making sure they stayed south of North 12th Street, east of Berry and Wythe, and the hell out of a then-”sketchy” McCarren Park, if you can believe it. Then after high school, he had a brief layover in Boston for college, which wasn’t quite the fit he was hoping for. So, in 2008, he moved “back” to Bushwick, which was very different from the Bushwick his family came from and started over in the McKibbin Lofts, the neighborhood’s equivalent of Ellis Island. Other things of note about Skyler Insler: Bomb-ass sweaters, long hair, gets free drinks at Heavy Woods, owns two dive bars—Alaska and Alphaville—in north Bushwick.

“I’ve been doing DIY shows and parties the whole time I’ve been here,” says Insler, 28, over the aforementioned drinks on a vaguely warm Sunday afternoon. “I [had] a huge loft and started doing it that way. Probably everybody was doing that because you would do kind of whatever you wanted.”

Some may be familiar with Insler’s Cheap Storage venue on Wyckoff Avenue and its “sweat on fire” stench, or perhaps you or someone you know attended his much-raved-about New Year’s Do Over party, which got shut down by the cops on its fifth anniversary. The venue’s last Facebook post in September 2014: “D.I.Y. or Don’t.”

Insler is the first to admit that the figurative party couldn’t last, both because his neighbors began to hate him (“They were like architects who wake up in the morning”), and because he was getting tired of cleaning up after everyone. So, out of that desire to stop cleaning up after other people, he and a couple of friends decided to open up a real venue with no neighbors, which they christened Alaska, near the Morgan L stop.

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“It was an accidental place,” he says of the Ingraham Street dive. “Like have a bar, let’s get a liquor license and be legit. It’d be cool.”

And maybe he should have seen then, in 2012, even before the cops came knocking, that Brooklyn’s DIY scene was becoming a shadow of its former self. After all, Insler and his business partners (who are no longer involved) soon figured out that Alaska couldn’t be a music venue, due to its impractically small size. So, they settled on just a bar, which is sometimes packed to the rafters and other times as desolate and inherently tragic as the real Alaska.

“So, Alaska caught on fire,” Insler adds matter-of-factly. “And I had broken my foot a week before.”

He learned quickly that if DIY is analogous to self-empowerment, dealing with insurance companies is the complete and exact opposite. For days, Insler wasn’t physically or legally allowed to attend to the gaping hole in Alaska’s roof, and the bar, which, a year later, still hadn’t become what he had envisioned it to be, was now little more than a burden.

“I had wanted an actual venue because Alaska never was a venue,” he says. “I’ve always just kind of had that in my mind, and I met this dude Scott [Rosenthal of local band, Beverly]. And I was just like, ‘Fuck it. I have nothing else to do. Let’s open a new place.’ ”

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A couple of things that Skyler and Scott have improved on through Alphaville: (1) better wallpaper, (2) a fully-operational kitchen that serves food that even architects would enjoy, (3) a sizable location right off Wilson Avenue in the heart of Bushwick proper, and (4) a barebones backroom with string lights, sound proofing and plenty of room for dancing, rocking out, getting in fights, or whatever people do at bars/restaurants/music venues these days.

“Alphaville’s so serious,” says Insler, his voice only half-full of regret for getting involved in something so legitimate. “It’s definitely more grown up. It’s more of a business, I’d say. Alaska’s definitely a business, but it’s just not mature. It’s this cool thing we did.”

And between health inspections, well-written Yelp reviews, and all the other red tape and maintenance involved, Insler is the first to say that Alphaville is a far cry from his DIY days, a fact that gets him talking about the domino-like collapse this past year-and-a-half of Williamsburg’s own DIY music scene following the closures of Death By Audio, Glasslands, and most notably, 285 Kent.

“I wasn’t sad when 285 closed,” says Insler. “[It] should have been a professional venue. It got top artists and musicians; the people they had working there and booking the shows are the best at what they do. Fucking make it legal–why not?”

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Add to that the places he actually cared about that have closed–Wreck Room, Living Bread Deli, Vanishing Point–and it’s a wonder that Insler is still in Bushwick at all. But he feels more willing now to work within the system rather than against it, offering up East Williamsburg’s Shea Stadium and the new iteration of Silent Barn as prime examples of making DIY work for “yourself”–and the city of New York.

“They still maintain the same ethos,” he says. “[But] it’s not DIY anymore. It’s real, it’s legit. That’s how it should be. Without criticizing anybody, a lot about DIY culture that people love is really just kind of laziness.”

Which brings us back to the fact that Alaska, like Bushwick, is still caught somewhere in the nebulous space between laziness and legitimacy. And for his part, Insler seems to have outgrown both.

“It’s changed so much,” he says, adding, “I just negotiated a new lease on my apartment and I’m tight with the landlord, but he’s like straight up, ‘I want you out.’ It’s like, alright, I respect your honesty.”

Alphaville, 140 Wilson Avenue, Bushwick
Alaska, 35 Ingraham Street, Bushwick

Correction: In a quote, Insler was misrepresented as saying Silent Barn had an “ego,” instead of “ethos.” The quote has been updated with Insler’s words.