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

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

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Inside the Playbook: JMSN on Why Music Videos Can Still Win for Artists

Inside the Playbook: JMSN on Why Music Videos Can Still Win for Artists

In this clip from The Manager’s Playbook, we talk about a music marketing truth most artists learn too late: a great music video isn’t “extra content,” it’s a long-term marketing asset.JMSN explains w...

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Inside the Playbook: JMSN on Why Being “Cool” Online Is Bad for Your Music Career

Inside the Playbook: JMSN on Why Being “Cool” Online Is Bad for Your Music Career

In this clip from The Manager’s Playbook, we talk about the part of the music business that’s driving artists crazy: the endless “how to blow up” social media advice that sounds confident and works fo...

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Inside the Playbook: JMSN on the DIY Blueprint to Grow Without Record Labels

Inside the Playbook: JMSN on the DIY Blueprint to Grow Without Record Labels

In this clip from The Manager’s Playbook, JMSN breaks down the real economics of the music industry: a record deal isn’t automatically “support.” It’s a trade of ownership and creative control for con...

13 Maalis 10min

The Manager’s Playbook 058: JMSN - DIY Artist Blueprint, Music Videos, Ads, Touring, Content & Music Marketing

The Manager’s Playbook 058: JMSN - DIY Artist Blueprint, Music Videos, Ads, Touring, Content & Music Marketing

In this episode of The Manager’s Playbook, I sit down with JMSN, artist, multi-instrumentalist, producer, and one of the best case studies for what real independent artist success looks like when you ...

10 Maalis 1h 53min

Inside the Playbook: J Erving III on The Skill Every Music Manager Needs

Inside the Playbook: J Erving III on The Skill Every Music Manager Needs

In this Manager’s Playbook clip, J. Erving unpacks a “superpower” that’s quietly responsible for most long careers in the music business: surrounding yourself with the right people, reading the room, ...

9 Maalis 18min

Inside the Playbook: J Erving III on How to Operate Like a Record Label in Any Role

Inside the Playbook: J Erving III on How to Operate Like a Record Label in Any Role

In this Manager’s Playbook clip, J. Erving III breaks down what changes when you go from managing outside the label system to operating inside it, and why most “label frustration” is really a culture ...

8 Maalis 19min

Inside the Playbook: J Erving III on What to Do Before Artists Break

Inside the Playbook: J Erving III on What to Do Before Artists Break

In this Manager’s Playbook clip, J. Erving breaks down a truth the music business loves to forget: artist trust is built in the off-season.Not when the venue is sold out. Not when the streams spike. R...

7 Maalis 21min

Inside the Playbook: J Erving III on How to Spot Great Artists Early

Inside the Playbook: J Erving III on How to Spot Great Artists Early

In this Manager’s Playbook clip, J. Erving breaks down how top music executives, A&Rs, and elite artist managers actually identify greatness and it’s not just “talent.”We talk artist development throu...

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