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

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 something that lasts.

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

Episoder(261)

Inside the Playbook: Azad Naficy on The Steps Successful Artists NEVER Skip

Inside the Playbook: Azad Naficy on The Steps Successful Artists NEVER Skip

In this episode clip from The Manager’s Playbook, Mauricio Ruiz sits down with artist, executive, and Avant Garden co-founder Azad Naficy to unpack one of the most important truths in the modern music...

12 Des 202515min

The Manager’s Playbook 048: Azad Naficy - Artist Development, Major Label Deals, Merch Strategy, Touring Realities & Building Sustainable Music Careers

The Manager’s Playbook 048: Azad Naficy - Artist Development, Major Label Deals, Merch Strategy, Touring Realities & Building Sustainable Music Careers

Azad Naficy has lived every corner of the music business - artist, manager, A&R, label co-founder, and the architect behind Peace of Mind Studio and Avant Garden Records. In this episode of The Manage...

9 Des 20252h 4min

Inside the Playbook: Theron Thomas on What Really Holds Artists Back

Inside the Playbook: Theron Thomas on What Really Holds Artists Back

In this clip from The Manager’s Playbook, Grammy-winning songwriter Theron Thomas breaks down one of the most misunderstood topics in the music industry, the myth of “selling your soul,” and why peopl...

8 Des 202517min

Inside the Playbook: Theron Thomas on Why Your Songs Aren’t Blowing Up

Inside the Playbook: Theron Thomas on Why Your Songs Aren’t Blowing Up

In this clip from The Manager’s Playbook, Grammy-winning songwriter Theron Thomas breaks down the real stories and strategy behind some of the biggest hit records of the last decade. From writing for ...

7 Des 202516min

Inside the Playbook: Theron Thomas on The Truth About Winning in Music

Inside the Playbook: Theron Thomas on The Truth About Winning in Music

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...

6 Des 202515min

Inside the Playbook: Theron Thomas on The Science of a Hit Song

Inside the Playbook: Theron Thomas on The Science of a Hit Song

In this episode clip, Grammy-winning songwriter Theron Thomas dives into one of the biggest truths in today’s music industry: the entire business is built on the backs of songwriters, yet they’re stil...

5 Des 202517min

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

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

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 Des 20252h 45min

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

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

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 ...

1 Des 202513min

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