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: Tyler Henry on How PARTYNEXTDOOR wrote Rihanna's HIT Record

Inside the Playbook: Tyler Henry on How PARTYNEXTDOOR wrote Rihanna's HIT Record

In this clip, we delve into what it takes to identify a great artist. Highlighting examples such as Rosalía and PARTYNEXTDOOR, the conversation covers the need for a natural draw to the music, an exce...

15 Feb 202511min

Inside the Playbook: Troy Carter on The Secret How To Grow A Music Artist From Nothing To Something

Inside the Playbook: Troy Carter on The Secret How To Grow A Music Artist From Nothing To Something

Troy Carter, Co-Founder and CEO of Venice Music, shares key strategies for small artists aiming to transition from small venues to larger ones. He emphasizes the importance of building demand in small...

14 Feb 20258min

Inside the Playbook: Troy Carter on The War Between TikTok & Universal Music Group

Inside the Playbook: Troy Carter on The War Between TikTok & Universal Music Group

Troy Carter, Co-Founder and CEO of Venice Music and former artist management of Lady Gaga shares his thoughts on the potential implications, legal disputes, and digital marketing war between Universal...

14 Feb 202516min

Inside the Playbook: Troy Carter on How to Find Music's Future Superstars

Inside the Playbook: Troy Carter on How to Find Music's Future Superstars

In this clip, Troy Carter, Co-Founder and CEO of Venice Music and former manager of global music sensations, Lady Gaga and John Legend, shares invaluable insights into identifying and nurturing extrao...

14 Feb 20256min

The Manager’s Playbook 017: Gavin Sheppard – The Remix Project, Building Creative Ecosystems, Hip-Hop as a Movement, Passion-Based Leadership, and Elevating Talent

The Manager’s Playbook 017: Gavin Sheppard – The Remix Project, Building Creative Ecosystems, Hip-Hop as a Movement, Passion-Based Leadership, and Elevating Talent

In this episode ofThe Manager’s Playbook, we sit down with Gavin Sheppard, co-founder ofThe Remix Project, a cultural incubator that has helped launch the careers of countless artists and creatives. G...

11 Feb 20252h 46min

The Manager’s Playbook 016: T-Minus - Artist Development, Creative Vision, Brand Building, Industry Insights, and the Journey to Longevity

The Manager’s Playbook 016: T-Minus - Artist Development, Creative Vision, Brand Building, Industry Insights, and the Journey to Longevity

In this episode, we sit down with Grammy nominated producer T-Minus to dive into his incredible journey through the music industry. From crafting hits for Drake to shaping the sound of some of the big...

27 Jan 20251h 48min

 The Manager’s Playbook 015: Natalie Prospere – From Social Work to Grammy Awards, Artist Advocacy, Resilience, Building Careers, Music Strategy, and Championing Authentic Voices

The Manager’s Playbook 015: Natalie Prospere – From Social Work to Grammy Awards, Artist Advocacy, Resilience, Building Careers, Music Strategy, and Championing Authentic Voices

Step into the world of Natalie Prosper in this unfiltered, inspiring interview as she reveals her journey from a driven social worker to a trailblazer in the music industry. Natalie shares how her Car...

23 Dec 20241h 55min

The Manager’s Playbook 014: Jessie Reyez & Byron Wilson – Industry Hustle, Label Bidding Wars, Work Ethic, Trust, and Building a Legacy

The Manager’s Playbook 014: Jessie Reyez & Byron Wilson – Industry Hustle, Label Bidding Wars, Work Ethic, Trust, and Building a Legacy

Jessie Reyez’s voice is unmistakable, but her journey to global recognition is a masterclass in grit, resilience, and relentless ambition. In this electrifying episode of The Manager's Playbook, hoste...

3 Dec 20242h 23min

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