Rich Castillo has spent nearly two decades inside the music industry, from Polydor, Sony, and EMI to Warner and now his own company, Lion Bear. In this episode of The Manager’s Playbook, Rich breaks down what A&R really means in 2025, why most artists lose urgency after signing, and how to navigate label politics without losing your vision.
We also dive into artist development, the tug-of-war between data and instinct, and what separates a good executive from a great one. Packed with real stories and practical lessons, this is a must-listen for artists, managers, and executives who want to build lasting careers, not just moments.
A conversation like this doesn't come cheap.
Watch the full episode on YouTube: https://www.youtube.com/@managersplaybook
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The Manager's Playbook