The Manager’s Playbook 038: Rich Castillo - A&R Legacy, Class Identity, UK Rap, Artist Development, Industry Evolution & Breaking Cultural Barriers

The Manager’s Playbook 038: Rich Castillo - A&R Legacy, Class Identity, UK Rap, Artist Development, Industry Evolution & Breaking Cultural Barriers

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

New episodes drop Tuesdays @ 10am ET

Jaksot(271)

Inside the Playbook: JMSN on Why Music Videos Can Still Win for Artists

Inside the Playbook: JMSN on Why Music Videos Can Still Win for Artists

In this clip from The Manager’s Playbook, we talk about a music marketing truth most artists learn too late: a great music video isn’t “extra content,” it’s a long-term marketing asset.JMSN explains w...

15 Maalis 19min

Inside the Playbook: JMSN on Why Being “Cool” Online Is Bad for Your Music Career

Inside the Playbook: JMSN on Why Being “Cool” Online Is Bad for Your Music Career

In this clip from The Manager’s Playbook, we talk about the part of the music business that’s driving artists crazy: the endless “how to blow up” social media advice that sounds confident and works fo...

14 Maalis 14min

Inside the Playbook: JMSN on the DIY Blueprint to Grow Without Record Labels

Inside the Playbook: JMSN on the DIY Blueprint to Grow Without Record Labels

In this clip from The Manager’s Playbook, JMSN breaks down the real economics of the music industry: a record deal isn’t automatically “support.” It’s a trade of ownership and creative control for con...

13 Maalis 10min

The Manager’s Playbook 058: JMSN - DIY Artist Blueprint, Music Videos, Ads, Touring, Content & Music Marketing

The Manager’s Playbook 058: JMSN - DIY Artist Blueprint, Music Videos, Ads, Touring, Content & Music Marketing

In this episode of The Manager’s Playbook, I sit down with JMSN, artist, multi-instrumentalist, producer, and one of the best case studies for what real independent artist success looks like when you ...

10 Maalis 1h 53min

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 Maalis 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 Maalis 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 Maalis 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 Maalis 20min

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