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Inside the Playbook: Rich Castillo on Why He Walked Away From the Major Label System

In this clip from The Manager’s Playbook, Rich Castillo reflects on his move from the major label system to launching his own independent label, Lion Bear. He shares why legacy and independence matter more than comfort, what inspired him to take control of his career, and how he’s thinking about the next chapter of the music business.

Rich also introduces his new podcast, The Hot Seat, designed to share insight from high-level executives and inspire the next generation. His first guest: UK music veteran Trenton Harris Lewis.

This is a conversation about ownership, perspective, and building…

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