Inside the Playbook: Rich Castillo on Why Artists Get Dropped Too Quickly
In this clip from The Manager’s Playbook, Rich Castillo pulls back the curtain on the realities of A&R and the inner workings of major labels. He explains how decisions actually get made inside the hi...
15 Sep 202518min
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 re...
14 Sep 202520min
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...
12 Sep 202512min
Inside the Playbook: Rich Castillo on The Harsh Truth About A&R at Major Record Labels
In this clip from The Manager’s Playbook, Rich Castillo breaks down what the role of A&R really looks like in 2025. From identifying and developing talent to balancing data, instinct, and marketing, R...
11 Sep 202518min
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 d...
9 Sep 20252h 13min
Inside the Playbook: Jared Cotter on How to Build a Team Around a Superstar
In this conversation, Jared Cotter and I dig into what it really takes to build a modern superstar.We talk about the rise of Shaboozey, how undeniable talent meets the right strategy, and the pivotal ...
8 Sep 202520min
Inside the Playbook: Jared Cotter on How Shaboozey Is Opening Doors in Country Music
In this conversation, Jared Cotter and I dig into the journey of breaking into country music and why authenticity always wins.We talk about how Shaboozey carved out his space in Nashville, the importa...
7 Sep 202512min
Inside the Playbook: Jared Cotter on The One Trait Every Great Manager Has
In this conversation, Jared Cotter and I dig into the world of music publishing and what it really takes to build a sustainable career.Jared shares his perspective as both a songwriter and a manager —...
5 Sep 202512min
