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: Isabel Quinteros on Being a Publicist to TikTok to AI

Inside the Playbook: Isabel Quinteros on Being a Publicist to TikTok to AI

What does it really take to build lasting partnerships between artists, brands, and technology?In this clip, Isabel Quinteros, SVP at Jen Music AI and former Global Music Partnerships lead at TikTok, ...

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Inside the Playbook: Isabel Quinteros on Why AI Can’t Touch the Human Soul

Inside the Playbook: Isabel Quinteros on Why AI Can’t Touch the Human Soul

AI is reshaping how music is created and consumed, raising new opportunities and new risks.In this clip, Isabel Quinteros, SVP at Jen Music AI and former Global Music Partnerships lead at TikTok, join...

5 Okt 202514min

Inside the Playbook: Isabel Quinteros on How Kids Are Experiencing Music in a Completely New Way

Inside the Playbook: Isabel Quinteros on How Kids Are Experiencing Music in a Completely New Way

AI is changing how music is created, discovered, and experienced.In this clip, Isabel Quinteros, SVP at Jen Music AI and former Global Music Partnerships lead at TikTok, breaks down how her team is bu...

3 Okt 202510min

Inside the Playbook: Isabel Quinteros on Why Artists Can’t Compete With AI

Inside the Playbook: Isabel Quinteros on Why Artists Can’t Compete With AI

Generative AI is shaking up the music industry, creating new opportunities and new risks.In this clip, Isabel Quinteros (SVP at Jen Music AI and former Global Music Partnerships lead at TikTok) breaks...

2 Okt 202517min

The Manager’s Playbook 041: Isabel Quinteros - TikTok, AI in Music, Artist Compensation, Blockchain, Ethical Innovation & The Future of the Industry

The Manager’s Playbook 041: Isabel Quinteros - TikTok, AI in Music, Artist Compensation, Blockchain, Ethical Innovation & The Future of the Industry

In this episode, Mauricio Ruiz sits down with Isabel Quinteros, former Global Music Partnerships lead at TikTok and now SVP at Jen Music AI. From her start in PR to shaping TikTok’s rise and now leadi...

30 Sep 20251h 22min

 Inside the Playbook: Shawn Desman and Managers on What Almost Ended Shawn Desman’s Music Career

Inside the Playbook: Shawn Desman and Managers on What Almost Ended Shawn Desman’s Music Career

After stepping away from music in 2015, Shawn Desman found himself questioning if he would ever return.In this conversation, he shares the pivotal moment with Drake that reignited his passion, the rol...

29 Sep 202515min

 Inside the Playbook: Shawn Desman and Managers on How They Sold Out Every Show

Inside the Playbook: Shawn Desman and Managers on How They Sold Out Every Show

Shawn Desman’s career looked finished, until it wasn’t.In this conversation, Shawn, Steve Zsirai, and Chad Walsh break down how a mix of social media strategy, data-driven decision-making, and the “Dr...

28 Sep 202518min

 Inside the Playbook: Shawn Desman and Managers on The Human Side of Music Management

Inside the Playbook: Shawn Desman and Managers on The Human Side of Music Management

What does it really take to build authentic relationships in music?In this conversation, Shawn Desman, Steve Zsirai, and Chad Walsh share why keeping a small, trusted circle is essential, how empathy ...

26 Sep 202511min

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