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In this clip from The Manager’s Playbook, we break down one of the most important turning points in Machel Montano’s career, the moment he had to choose between the traditional path of an “industry-ready” manager, or trusting his gut with Che Kothari, someone who wasn’t from the music business, but understood him on a deeper cultural and human level. Machel walks through the early days of being managed by his parents, navigating major-label systems, and what it felt like to hit a ceiling without the right partner beside him. Everything shifted in 2014, when he crossed paths with Che, a photographer at the time, who would eventually become the manager capable of helping reshape his entire career. Their story is a masterclass in what truly matters in artist management: trust, alignment, shared values, and a cultural connection strong enough to scale a global vision while keeping the soul of Trinidad & Tobago and Caribbean music at the centre. This clip is a rare look into how the King of Soca and his manager built one of the strongest artist–manager partnerships in Caribbean music, and why choosing the right partner can change everything. Simply put, a conversation like this doesn't come cheap. Chapters: 00:00 Choosing the Right Manager in the Music Business 00:18 Early Artist Career Struggles & Family Management 02:54 Finding Real Mentorship in the Industry 03:21 The Toronto Creative Community Connection 04:33 Trinidad & Tobago: Cultural Alignment and Artist Identity 05:08 The Manager’s Playbook: Artist Development & Music Careers 06:29 Carnival Culture’s Impact on Artist Vision 09:32 Rebuilding Strategy: Creating a New Creative Blueprint 13:52 Picking the Right Partner in the Music Industry The opinions shared by our guest are their own and do not necessarily reflect those of the host or The Manager’s Playbook. For the first time ever, I’m opening The Manager’s Playbook Mentorship: a hands-on, 3-month program where I personally help artists build structure, strategy, and momentum. If you’ve been feeling stuck or guessing your next move, this is where it becomes clear. Apply or book your free Playbook Diagnostic Call: https://subscribepage.io/TMPMentorshi... Follow The Manager's Playbook Newsletter https://www.the-managers-playbook.bee... Instagram / mauroisruiz TikTok / managersplaybook Facebook / mngrsplaybook X / mngrsplaybook LinkedIn / the-managers-playbook Snapchat / bcaz8cvw Website https://mngrsplaybook.com Host: Mauricio Ruiz Executive Producer: Mauricio Ruiz Director of Photography: Navindra Harbukhan On Location Sound: Nicholas Meah Grip & Asst Camera Op: Shaquille Bernard Editor: Madison Lair Co-Editor: Mauricio Ruiz Colourist: Will Dobak Sound Engineer: Madeline Currie Project Manager: Erica Kongvongxay Marketing Coordinator: Melanie Letra-Frade Production Company: 8 Til Faint #MachelMontano #Soca #CaribbeanMusic #trinidad #ArtistDevelopment #MusicBusiness #Soca2025 #TrinidadAndTobago #TheManagersPlaybook