The Manager’s Playbook 014: Jessie Reyez & Byron Wilson – Industry Hustle, Label Bidding Wars, Work Ethic, Trust, and Building a Legacy

Jessie Reyez’s voice is unmistakable, but her journey to global recognition is a masterclass in grit, resilience, and relentless ambition. In this electrifying episode of The Manager's Playbook, hosted by Mauricio Ruiz, Jessie and her longtime manager Byron Wilson pull back the curtain on what it really takes to build a legacy in the music industry.

From Jessie’s early days at Toronto’s Remix Project to creating a global buzz with tracks like Figures, this episode is packed with stories that define her rise. Jessie opens up about overcoming trust issues in an often ruthless industry, her unwavering dedication to understanding the business, and the sacrifices that come with chasing her dreams. Byron complements her narrative, revealing how strategic moves, teamwork, and a shared vision propelled Jessie’s career forward.

Listeners will hear behind-the-scenes accounts of label bidding wars, pivotal collaborations with icons like Calvin Harris and Eminem, and the hustle required to perform back-to-back shows without losing steam. The trio discusses the power of saying “no” to comfort zones, the art of negotiation, and the importance of surrounding yourself with people who share your values and vision.

Jessie’s candid reflections on work ethic, trust, and her drive to achieve goals like Grammy recognition make this episode a must-listen for anyone aspiring to make a mark in the creative world. Byron’s perspective as a manager adds depth, offering invaluable advice for navigating the industry with authenticity and strategy.

This isn’t just a conversation about music—it’s a deep dive into the mindset and hustle required to turn raw talent into a global movement. If you’re an artist, manager, or just someone who loves a good underdog story, Jessie Reyez’s journey will inspire you to keep pushing, no matter the odds.

🎧 Tune in now for an unforgettable episode that blends honesty, insight, and inspiration from one of music’s most dynamic voices.