After pouring time and energy into trying to make Swan Dive work at the Colorado building in the Arts District, the realization came that the uphill battle was only getting steeper.

The live music venue, owned and operated by Harvey Graham, was one of the most talked about openings of 2024. But Graham realized early on that it wasn’t panning out.

“The hard part about a live music venue is once the show is over, generally, everyone leaves,” Graham says.

At the old location, Swan Dive thrived during show hours but struggled to function as a hangout. Rather than fold, Graham decided to recalibrate and move Swan Dive down the block to the old Sinwave space at 1412 Main Street.

The relaunch incorporates a new front-of-house concept—Ugly Duckling karaoke—turning the building into a two-headed creature designed for both nightly commotion and live music.

Karaoke—reliably social and spontaneous—changes the equation. Bodies up front means sustainability in the back. It’s a logistical tweak that means live music no longer has to shoulder the entire financial burden alone. Ugly Duckling will operate in the street-facing room seven days a week from 5 p.m. to 2 a.m., while Swan Dive lives in the back as a dedicated music and event space, entered through the alley across from Liquid Diet.

Ugly Duckling is helmed by John Brophy. The founder of Portland’s cult-favorite Baby Ketten Klub is dubbed the “mastermind of America’s greatest karaoke night” by the New York Times.

“I’m planning on bringing the best sounding karaoke that we can muster,” Brophy says, describing a setup engineered to make singers feel like they’re fronting a live band—pro-grade audio, lighting and KJswho are equal parts sound tech and hype man.

Despite opening just blocks away from Dino’s, the Arts District’s decades-old karaoke institution, Brophy isn’t sweating competition.

“In Portland, you can’t throw a microphone without hitting another karaoke bar,” he says. “They all have their own angles.”

Ugly Duckling skews maximalist—less dive-bar singalong, more solo stardom, he adds.

Swan Dive will be designed by interior visionary Joey Moon, who had a major hand in Oddfellows’ 2024 remodel. Graham says the new location also corrects something that always felt slightly off.

“It felt like that [old] space wasn’t perfect for live music,” Graham says of the Colorado building, which sat atop restaurants. “This just feels like a live music venue.”

Ugly Duckling is slated to open the first week of February, with Swan Dive’s bar and full live music programing following shortly after.