Kayla Diamond on Leaving Law To Launch a Label, How Spotify Has Made & Erased Careers & More

Kayla Diamond joins I Hate Simkin to chat about the realities of the modern music industry — the parts that happen after you make it. Kayla shares how she left law school to pursue music, accidentally hung up on the label that signed her, and quickly found herself navigating radio success, touring pressure, and an industry that didn't work the way she was promised. They explore how streaming platforms reshaped careers overnight, the emotional toll of bad management, why Kayla stepped away at her peak — and how she rebuilt her life and career by founding Kolossal Records. This episode is about artist development, control, burnout, and why longevity in music often means redefining success entirely. This episode is also available on all audio podcast platforms and in video on YouTube. Subscribe to I Hate Simkin for bi-weekly deep dives into iconic Canadian music stories, behind-the-scenes label moments, and artist career turning points. Likes, comments, and feedback help massively — thank you for supporting the show.