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The Manager's Playbook

Inside the Playbook: Rich Castillo on Why Artists Get Dropped Too Quickly

19 min15 september 2025

In this clip from The Manager’s Playbook, Rich Castillo pulls back the curtain on the realities of A&R and the inner workings of major labels. He explains how decisions actually get made inside the hierarchy, the role data plays in scouting talent, and why live shows still matter in discovering artists.

We also explore how young A&R execs can grow within the system, the pressure IPOs put on creativity, and the constant balancing act between taking risks and chasing profitability.

Packed with real stories and practical advice, this conversation is a must-listen for artists, managers, and aspiring executives who want to understand how today’s music industry really works.

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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