About this episode

Kala’i Pomroy and James Shaw discuss their journey in the music industry, their friendship, and their recent projects.

Kala’i Pomroy and James Shaw are musical artists from the Big Island of Hawai’i. These Hilo boys are now based on Oʻahu, and represent a new generation of local music — one that blends island reggae, R&B, hip-hop, and pop into something that feels both rooted and global at the same time. Their breakout track Keep Me In Mind helped put them on the map, and since then they’ve continued to build momentum with songs like Thyme, POUNDTOWN, Peaches, Sunshine, and Long Day.They’ve performed on platforms like HI Sessions, HI Now, and Sugarshack Sessions, and recently released their debut project Sink or Swim, collaborating with artists like HIRIE and Likkle Jordee, the Steppas, and 8R08 along the way.In this episode we talk story about growing up in Hilo, how they became friends, the start of their music career, their hustle to make money, taking a break to refocus, their reemergence to the music scene, their first album, and so much more. Enjoy!Full episodes:🎥 https://www.youtube.com/@KeepitAlohaPod/videosBuy our merch:🛍️ https://keepitaloha.com/Support us:🤙 https://www.patreon.com/kamakadiasFollow us:📸 Instagram – https://www.instagram.com/keepitalohapod/🎵 TikTok –…

People in this episode

Host: Kamaka Dias

Guests: Kala’i Pomroy, James Shaw

Topics covered

• Hawaiian music
• local artists
• music career
• friendship
• break and reemergence
• collaboration

Mentioned in this episode

Organizations: Steppas, 8R08, HI Sessions, HI Now, Sugarshack Sessions

Books & works: Keep Me In Mind, Thyme, POUNDTOWN, Peaches, Sunshine, Long Day, Sink or Swim

Places: Big Island of Hawai’i, Oʻahu

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• Big Island Roots, Military Discipline, Vegas Hustle | Justin Hong Keeps It Aloha in Vegas (Ep. 228) · May 14, 2026 · 2h 17m

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