Tinywiings is entering a new era with the release of her Pretty Problems EP, marking the beginning of her joint venture with Sony alongside ShowoffGang Music.
Before making her move to the U.S., the Calgary native built strong ties with her hometown rap community, helping foster what she describes as a tight-knit ecosystem.
“There’s just not that many of them [rappers],” Tinywiings said of Calgary’s rap scene. “But yeah, we definitely go to each other’s shows and if there’s opportunities that would suit one of us better, you know, we are always kind of looking out for each other in that way because the community is so small.”
Despite the scene’s size, Tinywiings points to Calgary’s lively festival circuit as a key part of her journey, including Sled Island, a four-day, citywide festival featuring artists across multiple genres.
That grassroots community building work, paired with her online presence, helped lead to her deal with ShowoffGang Music and Sony.
“Yeah it’s like obviously a huge deal, the ShowOffGang stuff just felt right, or I wouldn’t have signed anything,” she said. “It’s like these are my older brothers. They are just like my team and they’re looking out for me and I’ve just felt that since day one.”
Founded by her “Wind Me Up” collaborator J-HAZE in Pittsburgh, ShowoffGang Music has taken the reins in Tinywiings’ artist development and joint venture with Sony.
As for the major-label side of the deal? Tinywiings is happy to let her team handle the business.
“With the Sony stuff, that’s kind of above my head, they’re like, ‘you focus on the music and we’re doing this for you,’ and I’m like, oh my God, music to my ears,” she said.
Stream Pretty Problems above.



