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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Inside the Playbook: J Erving III on The Skill Every Music Manager Needs

Inside the Playbook: J Erving III on The Skill Every Music Manager Needs

In this Manager’s Playbook clip, J. Erving unpacks a “superpower” that’s quietly responsible for most long careers in the music business: surrounding yourself with the right people, reading the room, ...

9 Mars 18min

Inside the Playbook: J Erving III on How to Operate Like a Record Label in Any Role

Inside the Playbook: J Erving III on How to Operate Like a Record Label in Any Role

In this Manager’s Playbook clip, J. Erving III breaks down what changes when you go from managing outside the label system to operating inside it, and why most “label frustration” is really a culture ...

8 Mars 19min

Inside the Playbook: J Erving III on What to Do Before Artists Break

Inside the Playbook: J Erving III on What to Do Before Artists Break

In this Manager’s Playbook clip, J. Erving breaks down a truth the music business loves to forget: artist trust is built in the off-season.Not when the venue is sold out. Not when the streams spike. R...

7 Mars 21min

Inside the Playbook: J Erving III on How to Spot Great Artists Early

Inside the Playbook: J Erving III on How to Spot Great Artists Early

In this Manager’s Playbook clip, J. Erving breaks down how top music executives, A&Rs, and elite artist managers actually identify greatness and it’s not just “talent.”We talk artist development throu...

6 Mars 20min

The Manager’s Playbook 057: J. Erving III - Artist Development, Music Distribution, Label Services, Team Building, Manager Mindset, SONY/The Orchard & Streaming Growth

The Manager’s Playbook 057: J. Erving III - Artist Development, Music Distribution, Label Services, Team Building, Manager Mindset, SONY/The Orchard & Streaming Growth

In this episode of The Manager’s Playbook, I’m joined by J. Erving III, CEO & Founder of Human Re Sources (a SONY Music/The Orchard partner), to talk about what it really takes to build an artist-led ...

3 Mars 1h 50min

Inside the Playbook: Jacob Paul on Music Publishing Deals 101

Inside the Playbook: Jacob Paul on Music Publishing Deals 101

If you’re a songwriter, producer, or manager, this is the publishing conversation that saves people from “congrats on the deal” regret.In this clip, Jacob Paul breaks down what a co-publishing (co-pub...

2 Mars 5min

Inside the Playbook: Jacob Paul on Mechanical Royalties

Inside the Playbook: Jacob Paul on Mechanical Royalties

If you’re an independent artist, producer, or songwriter, there’s a good chance you’re doing the loud part right (streams, content, growth) while missing the quiet part that builds real stability: mus...

1 Mars 15min

Inside the Playbook: Jacob Paul on How Global Music Publishing Royalties Work

Inside the Playbook: Jacob Paul on How Global Music Publishing Royalties Work

You can be “up” on Spotify and still collect $0 in publishing royalties.That’s the quiet trap: publishing isn’t paid by default. Master recording money tends to flow through labels and distributors. B...

28 Feb 8min

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