Inside the Playbook: Rich Castillo on How Failure Builds Resilience in the Music Industry

Inside the Playbook: Rich Castillo on How Failure Builds Resilience in the Music Industry

In this clip from The Manager’s Playbook, Rich Castillo dives into the rise of UK rap culture and its global impact. He explains how London’s melting pot of influences creates a distinct sound, why regional identity is crucial for artists, and how UK rap compares to the U.S. scene.

Rich also shares his personal journey, from early career setbacks and getting fired to thriving as an executive, working with emerging artists like Liverpool rapper Cast, and building successful teams. Along the way, he highlights lessons in resilience, financial realities, and the challenges of scaling in the music business.

This conversation is about more than music. It’s about culture, survival, and building a career with real substance.

A conversation like this doesn't come cheap.


Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/2XcP1p1vnPO2a5DHDnJzVO?si=XnodX5FcQIWW59yzWRaWfg


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

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Inside the Playbook: Jacob Paul on How Global Music Publishing Royalties Work

Inside the Playbook: Jacob Paul on How Global Music Publishing Royalties Work

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Inside the Playbook: Jacob Paul on Music Publishing 101

Inside the Playbook: Jacob Paul on Music Publishing 101

You can have songs moving on Spotify, Apple Music, YouTube, TikTok, live shows, even vinyl and still miss the money that literally belongs to you on the songwriting side.In this clip, Jacob breaks dow...

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The Manager’s Playbook 056: Jacob Paul - Music Publishing 101, Master vs Publishing, Mechanical Royalties, Global Royalties, Black Box Royalties & Catalog Ownership

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You can build a monster Spotify audience and still collect $0 in music publishing royalties. No warning. No system message that says, “Hey, you’re leaving money behind.” That’s because publishing isn’...

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Inside the Playbook: Paris Cole on Artist Management for New Artists

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In this clip, Paris Cole and I break down the real mechanics of artist development and what it takes to break an artist in today’s music business, especially when you’re building without massive budge...

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Inside the Playbook: Paris Cole on How to Build a Real Fanbase as an Artist

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In this clip from The Manager’s Playbook, Paris Cole and I break down what separates artists who build a real brand identity from artists who only get exposure.Paris explains that it often comes down ...

22 Helmi 19min

Inside the Playbook: Paris Cole on How to Build a Global Artist

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In this clip from The Manager’s Playbook, Paris Cole breaks down artist development through branding, styling, and creative direction and why audiences can instantly tell when an artist is “trying too...

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The Manager’s Playbook 055: Paris Cole - Artist Development, Brand Vision, Styling as Strategy, Fan Engagement & Building From Scratch

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Paris Cole is a true music industry multi-hyphenate, artist manager, creative director, and stylist, and in this episode of The Manager’s Playbook, she breaks down what it actually takes to develop ar...

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Inside the Playbook: SonReal on How to Tour Without Going Broke

Inside the Playbook: SonReal on How to Tour Without Going Broke

Touring isn’t just stage time. It’s a business model.In this clip, SonReal breaks down how live shows became one of the most important parts of his career, not only as performance craft, but as a real...

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