In this episode of I Hate Simkin, Jonathan reflects on managing Canadian rock singer Holly McNarland — from her edgy Sour Pie EP to her Juno-winning breakthrough with Stuff. Holly’s powerful voice, raw personality, and unforgettable stage presence made her stand out, but timing, life changes, and the harsh realities of the industry shaped her path.

Jonathan shares candid stories about touring, the challenges of management, and why talent isn’t always enough in the music business, as well as a look at Holly's later work and what she's up to now.

He also looks back at the plaque for You Can't Stop the Bum Rush, the album by LEN which included one of the biggest hits of the 90s, Steal My Sunshine - The story of how it came to be is filled with twists, chaos, and unforgettable moments. Jonathan shares his behind-the-scenes perspective on working with Marc & Sharon Costanzo — from early underground albums, to MuchMusic snow jams, to negotiating samples, to the international explosion of Steal My Sunshine.

This episode dives into quirky brilliance, lawsuits, budgets blown on partying, and the reality of what happens when one hit song takes a band around the world.

🎙 Hosted by Jonathan Simkin, I Hate Simkin pulls back the curtain on the music industry with raw, unfiltered stories.