Inside the Playbook: Machel Montano & Che Kothari on the Real Cost of Success

In this conversation, we dig into one of the most important parts of an artist’s journey: learning how to invest in yourself long before the world believes in you.

Machel Montano and Che Kothari break down what that looked like inside the Caribbean music ecosystem, the risks, the reinvestment, the discipline, and the vision it takes to build something that lasts. They talk about the lessons they learned from mentors, the business principles that shaped their partnership, and how technology and strategy became tools for scaling Machel’s career far beyond Carnival seasons and Soca stages.

What stands out most is the balance: ambition and grounding, creativity and structure, culture and long-term planning. It’s a rare look at how great artists and great managers think when they’re building for longevity, not just moments.

If you’re an artist, manager, entrepreneur, or anyone navigating the music business, this clip is full of principles you’ll want to revisit more than once.

Simply put, a conversation like this doesn't come cheap.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/0LMnduBDxM02PuYb6tW2xN?si=1KnMQX9ITwmvI2xDUpNQgw

Watch the Episodes On Youtube: https://www.youtube.com/@managersplaybook