Rhymesayers’ Skye Rossi Looks Back—and Ahead

I work with Rhymesayers, the independent hip-hop record label and artist management firm based in Minneapolis. Atmosphere, Aesop Rock, Brother Ali—that’s us. Over the last 15-plus years, I’ve taken a lot of photos of what we do. Most weren’t planned but instead captured in the same serendipitous way I work. Unfortunately a lot of the images I wanted to share were lost, but that just reinforces the serendipity, making it imperfect from the beginning and thus easier to share. These words and photos are my own and aren’t meant to tell the organization or artists’ stories. It’s simply to illuminate my own small piece in the whole thing and how the work has evolved.

Eyedea & Abilities at my studio in the Burlesque Design office for the E&A album campaign, Jan. 01, 2004

Eyedea & Abilities at First Avenue, Aug. 19, 2007

When I started working at Rhymesayers at 24 I had no idea where it would take me. The job was appealing because I saw passion in the people I met. It was a chance to be part of something special—from the ground up. I’ve always wanted to be challenged in my career, looking for growth and non-traditional spaces, and Rhymesayers seemed to satisfy a lot of that. My adventure in music began with no formal training, but plenty of on-the-job learning. I worked hard from an early age, and the enjoyment of seeing artists’ dreams come true gave me purpose. I went from throwing house parties in high school and promoting shows, formalizing a loose collective into a record label, working at Cheapo record store or with Life Sucks Die Magazine and Burlesque Design to collaborating with other local artists. Looking back it feels like the perfect mix of experience to prepare for the roles over the years at Rhymesayers. I’d known Slug and Ant (Atmosphere, and two of Rhymesayers’ founders) from shows and talks we’d had at Cheapo; eventually Ant suggested a meeting with Siddiq (another cofounder) so we could work together. In that first meeting I was struck at his similar drive and approach to work. It was that complementary nature that convinced me to start. Here was a group of people with no one model to follow or formal training—people who simply take risks and do what feels right at the time to get the job done.

P.O.S at Burlesque Design, Sept. 30, 2006

Rhymesayers 10 Year anniversary at First Avenue, June 09, 2007

Rhymesayers 20 year anniversary show prep at the Target Center. Dec. 03, 2015

A recurring theme in my work has been to figure it out; make it happen, whatever it is, with or without the time or budget. While there are many artists, venues, and creative outlets in Minneapolis, it wasn’t a hub for the music or entertainment industry. The lack of resources, related industry, and other labels pushed us to create our own tools and connect with creatives around the globe. Surrounded by these artists and my partners, I felt empowered to take risks. I came to find out that the more grandiose ideas weren’t realistic, and the more executable ideas were the ones that showed the most value.

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The responsibility I took on pushed me into a serious space. I wanted to guarantee all of our work and to control the outcomes, which simply wasn’t possible. I was getting in the way of my own happiness as well as the success of the business. More was always better, more hours, more focus, but somehow it was never enough. The pressure I was putting on myself forced me to seek a new approach to work. Now, instead of holding on to control of various projects and roles, I’m collaborating, delegating, and asking for advice, which improves my work and speeds up the development of projects and countless other aspects of business. The process has been far from perfect, but I’m learning to listen and reflect on the mistakes I’ve made, always searching for ways to improve.

Brother Ali at the Hideaway Studio, Jan. 09, 2006

Ant’s Basement, Sept. 21, 2003

In the last few years I’ve transitioned into a more focused leadership space. I took my previous role and split it into three parts and recruited talented folks to take on those jobs. Now I can consider new opportunities and approaches to our business. A huge factor in this involves hiring and connecting the right people to continue the tradition of an artist-first creative enterprise, allowing people to lead and take risks with room to learn but also maintaining a space to offer guidance. This allows me, too, to learn new skills, face new challenges, and become a better leader. I want to be part of building a space that allows artists to succeed and share their art with the world. I have a deep appreciation for the help and support I’ve received from my own mentors and friends along the way, and I’m proud of the work I’ve done with the amazing artists, coworkers, and collaborators over so many years. I’m excited to continue into this new phase. Who knows what the future holds.

Abilities at First Avenue, Dec. 30, 1998

Slug at First Avenue, Dec. 30, 1998

I met Skye a decade ago at Soundset, the music festival he helps run. As a partner in Rhymesayers Entertainment, he’s worked there for 15+ years. He may have gotten the boot from art school, but his mother—a photography professor—passed along a sharp eye, sense of curiosity, and a passion for making photos. —Chris Force

All photos by Skye Rossi. Find him on Instagram @skyerossi

This article originally appeared in the Spring/Summer 2019 issue of Sixtysix with the headline “Work As My Witness.” Subscribe today.