Grammy-Nominated artist Jessie Reyez discusses with her artist manager (and me her former manager) about her music industry success. We reveal the secrets behind music industry success, her amazing ability to craft massive global hit records, and continuously grow her music business empire.
Jessie, Byron Wilson and myself (her former manager) pull back the curtain on the highs, the lows, and the untold stories of her journey on The Manager’s Playbook Podcast. From a small dream to 5 billion streams writing massive hits in the music industry with legends like Eminem, Lil Wayne, Calvin Harris, Dua Lipa to surviving the relentless grind of the industry, Jessie lays it all on the line as she gets brutally honest about the music business.
Discover the secrets behind her rise: This Grammy-Nominated artist reveals tips to succeed in the music industry like trust issues that fueled her drive, the unshakable work ethic that set her apart, and the tight-knit team that helped her break barriers. Hear firsthand how she navigated label bidding wars, stood her ground, and built a career defined by authenticity and raw talent.
This episode goes beyond the surface, diving deep into the significance of breaking the rules, the art of negotiation, and why adaptability is the ultimate superpower in an ever-changing music landscape. Whether you’re an artist, a manager, or a fan, you won’t want to miss this inside look at what it takes to thrive at the highest level.
Ladies and gentlemen, A Conversation Like This Does not Come Cheap.
00:00 “I’d be Dead”
00:15 Introducing Byron Wilson & Jessie Reyez
03:27 Understanding the Music Business
06:46 Building a Team and Overcoming Challenges
08:00 Growth on the Stage and Evolution as a Performer
13:48 Getting out of the Comfort Zone
15:00 Breaking Out and Becoming a Household Name
19:59 How Important is Work Ethic?
21:19 The Remix Project and Early Collaborations
25:05 Shoutout to King Louie
29:10 Momentum is so Important
31:08 Chicago Love and Toronto Coming Around
32:58 Chance & Pat Change the game
35:09 Jermī Gives the Stamp of Approval
37:15 Refusing the “L” & Redefining Success
38:50 The Birth of ‘Figures’ and Its Impact
42:14 The Artist-Manager Dynamic
45:40 The Bidding War, Label Negotiations, & Respect
51:54 The Importance of a Strong Team
01:06:23 Challenges with Record Labels
01:08:06 Adapting and Overcoming
01:11:42 Studio Process and Songwriting
01:14:48 Is Jessie allergic to hits for herself?
01:17:15 Navigating Stress and Self-Preservation
01:17:44 The Unspoken Fears of Success
01:18:54 The Importance of Community and Understanding
01:23:11 The Blessing of COVID Break
01:26:33 Balancing Family and Career
01:28:16 The Role of Sacrifice in Success
01:36:26 Marketing Strategies and Artist Authenticity
01:54:26 Making It Your Own: The Creative Process
01:54:47 Collaborating with Black: The Story Behind the Feature
01:55:24 Tour Stories: The Highs and Lows
01:57:13 The Iconic Verse: 6lack’s Contribution
02:03:57 Working with Eminem: A Dream Come True
02:09:32 Calvin Harris Collaboration: From Mixtapes to Hits
02:19:09 Book Recommendations and Final Thoughts
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Host: Mauricio Ruiz
Producer: Mauricio Ruiz
Channel Management: Jermelle Bahadosingh
Production Company: 8 Til Faint
Studio: Startwell Toronto
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