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

Episoder(263)

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Inside the Playbook: Jared Cotter on The One Trait Every Great Manager Has

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Inside the Playbook: Jared Cotter on Managing After a Hit Record

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In this conversation, Jared Cotter and I break down the making of Shaboozey’s “A Bar Song (Tipsy).”We talk about the creative spark, the key moments that shaped the record, and what it takes to recogn...

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The Manager’s Playbook 037: Jared Cotter - Shaboozey, Paul Russell, Jay Sean, Building Superstars Independently, Shaboozey’s Rise, Country Music & Leadership Lessons

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Jared Cotter is the manager behind one of the biggest independent success stories of the decade.In this episode, we talk about how Shaboozey’s “A Bar Song (Tipsy)” made history, spending 19 weeks at #...

2 Sep 20251h 20min

Inside the Playbook: Loren Medina on How to Pitch as an Artist

Inside the Playbook: Loren Medina on How to Pitch as an Artist

In this episode of The Manager’s Playbook, publicist Loren Medina unpacks the evolving music industry and what independence really means for artists today. She challenges the myth that signing to a la...

1 Sep 202518min

Inside the Playbook: Loren Medina on The #1 Thing Missing in the Music Industry - Strategy

Inside the Playbook: Loren Medina on The #1 Thing Missing in the Music Industry - Strategy

In this clip of The Manager’s Playbook, publicist Loren Medina talks about what it’s really like to work with record labels from the outside. She explains why so many label teams lack long-term strate...

31 Aug 202519min

Inside the Playbook: Loren Medina on The Brutal Reality of the Music Industry

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In this clip of The Manager’s Playbook, publicist Loren Medina shares her journey from leaving Sony to launching Digital Girl in 2009, one of the first social media marketing companies in music. She r...

29 Aug 202516min

Inside the Playbook: Loren Medina on The #1 Mistake Artists Make When Hiring a Publicist

Inside the Playbook: Loren Medina on The #1 Mistake Artists Make When Hiring a Publicist

In this clip of The Manager’s Playbook, publicist Loren Medina shares why passion is the foundation of every client relationship she takes on. From choosing artists based on authenticity, to navigatin...

28 Aug 202522min

The Manager’s Playbook 036: Loren Medina - Jessie Reyez, Ca7riel & Paco Amoroso, J Noa, The Business of Music PR, Breaking Artists & The Ugly Truth About the Music Industry

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In episode 36 of The Manager’s Playbook, Mauricio Ruiz sits down with publicist and strategist Loren Medina, founder of Guerrera PR. From her start at Sony to building her own agency, Loren shares the...

26 Aug 20252h 22min

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