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: LaRussell & Tietta Mitchell on The Music Marketing Funnel That Actually Pays

Inside the Playbook: LaRussell & Tietta Mitchell on The Music Marketing Funnel That Actually Pays

Most artists don’t hate ads. They hate what bad ads reveal.In this clip, LaRussell breaks down how he actually uses ads as an independent artist: not to force Spotify streams or fake momentum, but to ...

21 Maalis 13min

Inside the Playbook: LaRussell & Tietta Mitchell on The Roc Nation Deal

Inside the Playbook: LaRussell & Tietta Mitchell on The Roc Nation Deal

LaRussell didn’t partner with Roc Nation because he needed a machine. He partnered because he built one first.In this clip of The Manager’s Playbook, LaRussell and his manager Tietta Mitchell break do...

20 Maalis 26min

The Manager’s Playbook 059: LaRussell & Tietta Mitchell - Roc Nation Deal, Independence, Ads, Direct-to-Fan, Touring & Music Marketing

The Manager’s Playbook 059: LaRussell & Tietta Mitchell - Roc Nation Deal, Independence, Ads, Direct-to-Fan, Touring & Music Marketing

LaRussell is the rare independent artist who didn’t partner with Roc Nation because he needed a label. He partnered because he built enough leverage to make the label behave like a partner.In this epi...

17 Maalis 2h 15min

Inside the Playbook: JMSN on the Anti-Ad Music Marketing Plan

Inside the Playbook: JMSN on the Anti-Ad Music Marketing Plan

In this clip from The Manager’s Playbook, we get into the unglamorous side of the music business that every independent artist eventually faces: release week feels stressful because you’re the label.J...

16 Maalis 17min

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...

15 Maalis 19min

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...

14 Maalis 14min

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

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