In the music industry, talent isn’t the bottleneck. The bottleneck is management, systems, and business literacy.
In this episode of The Manager’s Playbook, Sickick breaks down the real behind-the-scenes journey most artists never talk about: what happens when a manager relationship goes sideways, money turns conversations into tension, and you’re forced to learn the music business the hard way.
We get into artist management red flags, why trust is the biggest de-stressor for artists, and how bad decisions in the “business side” can create real-world consequences, like touring issues that can pause momentum overnight.
Then the story opens up: Sickick’s rise from early YouTube momentum to building an audience through content strategy, platform-native growth, and a clear understanding of independent artist leverage. We talk master ownership, distribution deals, and how major label conversations change when you build real demand first.
And yes, he walks through collaborations and studio dynamics with Madonna, plus records connected to Post Malone and Doja Cat, and what high-level collaboration actually feels like when there are no egos in the room.
If you’re an artist, producer, DJ, or aspiring manager trying to figure out team building, streaming growth, fanbase development, content systems, and how to stop “working hard” without building leverage, this is the episode.
Simply put, a conversation like this doesn't come cheap.
Book a 1:1 Strategy Session with Mauricio Ruiz, host of The Manager's Playbook, with over 16 years of experience for tailored advice for artists and managers. Consultation Fees Apply https://calendly.com/themanagersplaybook
Chapters:
00:00 Music Industry Management
(why managers matter & how careers get shaped)
00:26 Artist Development & Career Strategy
(reconnecting, early momentum, long-term positioning)
02:05 Artist Manager Red Flags
(bad management, trust breakdown, and the “documentary moment”)
04:24 Touring Visas & Immigration for Artists
(US/Canada border, O-1 / O-2 basics, touring compliance)
07:50 Music Business Fundamentals
(why artists must know contracts, systems, and deal structure)
14:06 Artist Reinvention & Brand Identity
(the birth of Sickick, mental resilience, and rebuilding purpose)
21:32 Music Collaborations & Major Artist Features
(how collabs happen, leverage, and industry relationships)
26:59 Content Strategy for Musicians
(TikTok DJ persona, audience growth, and social media positioning)
28:45 Original Music vs Algorithms
(artistry, authenticity, and avoiding the “numbers trap”)
29:11 Artist Management Case Study
(building a decade-long career with Jessie Reyez (management longevity))
29:36 Creative Process & Music Production Workflow
(inspiration, output systems, and staying consistent)
34:18 What Makes a Good Manager
(trust, communication, accountability, and being “good cop / bad cop”)
39:56 EDM Artist Strategy & Genre Evolution
(transitioning from EDM momentum to originals)
47:47 Global Music Culture & Canadian Music Industry
(identity, sound, and cross-market perspective)
51:13 Awards Strategy & Career Vision
(long-term goals, positioning, and building toward Grammys-level outcomes)
54:19 Independent Artist Playbook
(final takeaways on leverage, teams, and sustainable growth)
The opinions shared by our guest are their own and do not necessarily reflect those of the host or The Manager’s Playbook.
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Host: Mauricio Ruiz
Executive Producer: Mauricio Ruiz
Director of Photography: Austin Bourdages
On Location Sound: Jesse Lopez
Editors: Madison Lair
Co-Editor: Mauricio Ruiz
Colourists: William Dobak
Sound Engineer: Madeline Currie
Project Manager: Erica Kongvongxay
Marketing Coordinator: Melanie Letra-Frade
Production Company: 8 Til Faint
#themanagersplaybookpodcast #musicbusinesspodcast #musicbusiness #musicindustry #artistmanagement #musicbusinesstips
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