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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7 Dec 202516min

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In this clip from The Manager’s Playbook, Theron Thomas opens up about the part of the music industry that rarely makes headlines: the grind, the pressure, and the personal history that shapes real ar...

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The Manager’s Playbook 047: Theron Thomas - GRAMMY Songwriter of the Year, Songwriter Rights, Music Industry Inequality, Publishing Realities & Hitmaking Strategy

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Most people talk about hit songs.Theron Thomas writes the ones that define entire eras.In this episode of The Manager’s Playbook, I sit down with one of the most influential songwriters in modern musi...

2 Dec 20252h 45min

Inside the Playbook: Machel Montano & Che Kothari on How the King of Soca Designs World-Class Shows

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In this conversation, Machel Montano opens up about what truly goes into crafting a great live performance, not just the music, but the presence, discipline, and attention needed to make a crowd feel ...

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