By Emma Schwichtenberg

When 12-year-old Sina Holwerda told her parents she wanted to be a rapper, they didn’t expect it to stick. After 15 years, the now 27-year-old Holwerda, known by her middle name “Wynne,” clearly had the right idea. The Lake Oswego-raised University of Oregon grad is a rapidly rising hip-hop star based in Portland.

By age nine, Wynne was already hooked on the beats and rhythms that would later define her career. She grew up listening to Jay-Z, 50 Cent, T.I., Lil Wayne, and Eminem, writing remixes, and eventually creating original material on YouTube beats and participating in ciphers and contests online. Her base rides hard for her. Music videos she posts on Instagram are flooded with support from people who have followed her from those early years in the industry—the ride or die who heard a 12-year-old spit bars and knew she would be someone to keep an eye on.

Between 2010 and 2015, she immersed herself in the online underground rap scene, particularly on YouTube, where she built a small but dedicated following. In many ways the internet played a crucial role in Wynne's rise to fame. Her viral freestyles and engaging online presence caught the attention of hip-hop enthusiasts and casual listeners alike. In 2016, a particularly notable freestyle video went viral when a false rumor spread that Wynne was Eminem's daughter. While the claim was untrue, it helped catapult her into the public eye and generated significant buzz around her music.

Wynne's career took a significant leap forward when she joined EarthGang's "Welcome to Mirrorland" tour in early 2020. As the tour's support act, Wynne had the opportunity to learn from seasoned performers like EarthGang and Mick Jenkins. The pandemic, which cut the tour short, gave Wynne a deeper understanding of her craft and created a renewed determination to succeed.

Wynne's music has continued to evolve. Her debut album, released in 2019, received critical acclaim, and more recently in April 2023, Wynne's team began rolling out her new EP, "Some Like It Hot," with the release of fiery singles "Jaw Morant" and "Hot Friend." Her music seamlessly blends traditional hip-hop elements with contemporary sounds, creating a unique and refreshing style.

Wynne's journey has not been without its challenges. The pandemic, a toxic relationship, and the pressures of early adulthood have tested her resilience. However, these experiences have also fueled her creativity and led to personal growth. Wynne's ability to channel her struggles into her music has resonated with fans and added depth to her work.

In Wynne, Portland has found a true representative of its vibrant and eclectic spirit. Her story is one of passion, perseverance, and the power of music to transcend boundaries. As she continues to rise, Wynne remains a beacon of inspiration for aspiring artists everywhere.

Wynne recently spoke with Converge Music to discuss everything from the Portland music scene and her album release to her choice of nail color.

I always start with this: can you tell me a little bit about how you got your start in music, how did you start rapping?

Yeah. So, I had an older brother, and we shared an iTunes account. He kind of imposed his musical taste on me when I was really young. I was nine, and this was around the time "The Cool" by Lupe Fiasco came out. I was listening to a lot of Jay-Z, 50 Cent, T.I., Lil Wayne, and Eminem. I just totally fell in love with it. For a long time, it was like my closest friend. I've always been kind of a loner, so that was my outlet for everything, and I just decided that’s what I wanted to do.

When did you start deciding that it was something you wanted to do more seriously and professionally?

When I was 12. It's pretty early, but my heart and mind were set on it. It was funny having conversations with my parents when you're 12 and growing up in the suburbs, and you tell them you want to be a rapper. They were like, "Okay, nice, sure. That’ll change in a couple of years." But it didn't. By then, I was writing original stuff on YouTube beats and participating in online ciphers and contests.

How did you progress more from there? Some people play at cafes, but rap is a very specific type of music.

I started posting my verses online and built a small following on YouTube in the underground scene. Between 2010 and 2015, there was a big underground battle rap and cipher community on YouTube. I embedded myself in that, becoming a fan and supporter. I also did ciphers with Team Backpack in LA and competed on stage. Most of my following came from the internet, and during the peak of Twitter virality around 2016-2017, some of my freestyles were shared widely. I even had one where someone falsely claimed I was Eminem’s daughter, which went viral.

The internet has been pretty integral to your success, right?

100%. Hip hop fans can tell who genuinely cares about the craft. Early on, people saw me as a kid who loved rapping. That made some people root for me and others question why a white girl was rapping. My videos often sparked discussions, which helped them spread. Over the years, I've learned to navigate the public’s opinions and the extremes of internet discourse.

I know you were going to go on tour around 2020, and the pandemic interrupted that. What was the lead-up to this tour?

We were some of the last to tour before the pandemic hit. It was EarthGang's "Welcome to Mirrorland" tour with Mick Jenkins, Jurdan Bryant from Spillage Village, and me. We started in January 2020 and finished just as COVID was hitting. It was my first tour right after my debut album came out in October 2019. It felt like a victory lap that abruptly ended when the pandemic hit.

When you went to college, what did you study?

I studied music and took a lot of gender and ethnic studies courses, focusing on popular music history.

What were some lessons or experiences you took away from that tour?

I learned a lot about being a considerate headliner and performer. EarthGang and Mick Jenkins were very supportive, watching my sets, giving feedback, and bringing me back on stage. They taught me the importance of humility and providing opportunities for others. Touring with my best friends in a sprinter van was hard work but incredibly rewarding.

You mentioned reality hit you hard after the tour. How did you push through, and what strategies are you still using?

During the pandemic, my engineer and manager, Itay, and I locked into the studio and asked ourselves hard questions about our goals and the kind of music we wanted to make. We experimented with song structure and delivery. We also learned to shoot and edit our own videos to adapt to the new reality. One big lesson was making music videos that translated well to vertical formats for social media, which helped keep our audience engaged.

Have you ever felt pressured to move to a bigger city to further your career, or do you find unique advantages staying rooted in Portland?

Both. There's definitely pressure to move to LA for opportunities, but I’m a Pacific Northwest kid at heart. Portland has unique opportunities because we don’t have a lot of big productions happening. People here are willing to help and support, which allows us to pull off bigger-looking productions on a budget. There's so much talent here, and tapping into the community has been incredibly rewarding.

When you're freestyling, what’s the emotional or mental process you go through?

Freestyling is like riding a bike—it’s a muscle you have to practice. I try not to overthink it because that can lead to stumbling. The more you practice, the better you get at staying in the moment and delivering strong lines.

Do you get nervous before performances?

Always. The nerves hit right before I step on stage, but once I get through the first song, I feel on top of the world. The adrenaline helps, but I try to calm myself by thinking about how the performance will look in footage.

Is there a particular song that holds a special place in your heart or stands out in your discography?

Definitely. "Ego Check," my first big single with JID, will always be special. "Jaw Morant" from last year also stands out. Those songs represent a duality in my work that I’m proud of—club bangers and heartfelt therapy sessions.

How has the culture of Portland changed for you as you begin to get more mainstream success?

There are two sides to that coin. On one hand, it's extremely humbling because Portland is such a small community where everybody knows everybody. Many artists here grew up together in the Portland Public School system, while I didn't, so finding my place in the scene has been a learning experience. The support from the community is overwhelming; for example, Portland accounts for 15,000 streams of my newest single, "Rug Burn," which is significantly higher than other cities like Seattle. There’s a unique level of kindness in the Pacific Northwest that is very genuine. However, I also find myself getting comfortable because it's home. Changing up my environment, like spending time in LA, introduces new pressures but also offers fresh perspectives. Portland’s community, especially the OGs who have been supporting the scene for years, is very supportive. I strive to stay connected with them and appreciate that Portland is moving away from a "crabs in the barrel" mentality and starting to lift each other up more than ever.

What do you think about your music resonates most with your audience? Are there any specific tracks that resonate a lot?

I believe it’s my confidence. I hope my music allows listeners to feel confident in themselves. I’m unapologetic about my love for what I do and my belief in my own abilities. Since I was a child, I knew I wanted to pursue this path, and I've brought many supporters along with me on this journey. The attention to detail in my lyrics and my self-assuredness likely resonate with my fans, particularly those who are hip-hop enthusiasts.

Can you pinpoint a turning point in your career that felt significant?

Absolutely. The first major turning point was in 2017 when a freestyle I did over 21 Savage's "Bank Account" went viral on Twitter. Snoop Dogg posted it, which led to label meetings and a lot of opportunities. I was young at the time and chose not to sign with any labels, but it helped me build my team and form lasting connections. Being Billboard Rookie of the Month, and announcing my first national headline tour were significant milestones too. It felt like a shift where people began to understand my vision and I could finally show them what I saw for myself.

Outside of music, what do you like to do to relax?

I have a passion for natural history, particularly the Pleistocene era, which is the Ice Age. I’m fascinated by human history, mammals, and dinosaurs. I read extensively on these topics and watch documentaries. I can be a bit of a nuisance to my friends when I get excited and talk about the size of bears from 30,000 years ago. I also enjoy reading nonfiction books, especially science-related ones. I’d describe myself as a bit of a science nerd.

I noticed your nails because I was in red nail mode last week, and now you’re here with red nails. Is it for your album?

I love when people ask silly or personal questions unrelated to music, like what you do in your free time. But yes, I recently posted about having red nails for an album release, which totally received a lot of positive reactions from fans. It’s nice to share these little personal details with them.

Wynne is planning the upcoming release of the sequel to her highly successful EP from last year. Her plan includes dropping two EPs, which will be combined with additional tracks to create an even more impressive project. While the title and exact release date are yet to be announced, fans can look forward to its debut at the end of summer. The latest single from this project, “Dog at Me,” was released on July 12, 2024. 

To stay updated with Wynne, follow her on Instagram @sinawynne.