Boston’s music scene has been bubbling for years, and the conversation is shifting: are women leading the charge? On the latest episode of the Highstreet Podcast, the crew sat down with rising star Yanna G and her manager, Ikenna, for a raw and inspiring look at what it takes to break through right now. From rap battling her dad as a kid to winning a Boston Music Award, Yanna’s journey is one of resilience, artistry, and vision.
The episode opens with a world premiere: an unreleased track from Yanna produced by Dallas, showcasing the 21-year-old Boston R&B/soul artist’s smooth vocals and heartfelt storytelling. By the end, listeners got something new, Highstreet’s first-ever “Highball” featuring a pro, a playful shooting game that kept the energy high and authentic.
Yanna describes her style as soulful and authentic, drawing inspiration from icons like Erykah Badu, Lauryn Hill, and Black Odyssey. In the conversation, she highlighted Boston’s growing female-driven music scene, mentioning peers like Key, Tamara King, and Nate Speaks. She even gave listeners a glimpse of her creative process by recording a song during the interview itself.
Her artistry is currently anchored by a two-volume album project: Volume 1 explores the solitude and self-reflection that followed a painful heartbreak, while Volume 2 is about stepping back into the world, open to growth, connection, and new relationships.
For Yanna, music began at home. Her father, a rapper in the group 55th Regiment, would battle her in freestyle sessions, unknowingly planting the seeds for her career. She also credits Oompa, her high school music teacher, with giving her the first real opportunity to record. That mentorship and drive led her to the Boston Music Awards, where she took home New Artist of the Year, following Nate Speaks’ win the year before.
Her journey has already brought her to iconic stages, including performing at halftime during Celtics games, a moment that underscored just how far she’s come.
The podcast dove into the challenges of today’s industry landscape. Yanna and Ikenna spoke candidly about streaming platforms, the potential shift toward direct-to-consumer sales, and the looming questions around AI-generated music and its impact on authenticity. They emphasized the importance of cultivating real fan bases, the power of intimate shows, and the delicate balance of staying true to one’s artistic vision while building a sustainable career.
Beyond music, Yanna opened up about growth, heartbreak, and self-discovery. After a significant breakup, she turned to solitude to heal, learning self-love and redefining what relationships should mean for her. She reflected on how her parents’ long-term relationship once set unrealistic expectations for her own love life, and how creating Volume 1 helped her process that reality.
Through it all, Yanna remains committed to balance, embracing collaboration and teamwork without compromising her creative integrity.
The episode wrapped with laughs and competition as Yanna joined in on “Highball,” the show’s basketball shooting game, this time featuring her manager Ikenna, a professional basketball player and founder of the nonprofit 617 Peak. The moment reflected what makes Highstreet special: real conversations, cultural insight, and an atmosphere where music and community meet.
