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 role his wife played in guiding crucial career decisions, and the challenges of navigating management changes. Alongside Steve Zsirai and Chad Walsh, Shawn also reveals the strategic and data-driven approach that made his live comeback possible.

This is a story of resilience, reinvention, and what it really takes to build a second chapter in today’s music business.

Simply put, a conversation like this doesn't come cheap.


Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/1uwdpt8Z2i0PmUt70hhc76?si=ekjULlriRweFoLFGxe57Eg


Watch the Episodes On Youtube: https://www.youtube.com/@managersplaybook

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Inside the Playbook: Milana Lewis on Why Music Contracts Are Broken

Inside the Playbook: Milana Lewis on Why Music Contracts Are Broken

In this clip from The Manager’s Playbook, Mauricio Ruiz sits down with Milana Lewis, CEO & Co-Founder of Stem, to break down one of the music industry’s biggest flaws: royalty accounting.Milana shares...

18 Syys 202514min

The Manager’s Playbook 039: Milana Lewis – Artist Ownership, Royalties, Distribution vs. Delivery, Concord Partnership & The Future of Music Business

The Manager’s Playbook 039: Milana Lewis – Artist Ownership, Royalties, Distribution vs. Delivery, Concord Partnership & The Future of Music Business

In episode 39 of The Manager’s Playbook, Mauricio Ruiz sits down with Milana Lewis, co-founder and CEO of STEM, to unpack the realities of today’s music business.Milana explains why royalty accounting...

16 Syys 20251h 46min

Inside the Playbook: Rich Castillo on Why Artists Get Dropped Too Quickly

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 Syys 202518min

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 re...

14 Syys 202520min

Inside the Playbook: Rich Castillo on Why He Walked Away From the Major Label System

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 Syys 202512min

Inside the Playbook: Rich Castillo on The Harsh Truth About A&R at Major Record Labels

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 Syys 202518min

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 d...

9 Syys 20252h 13min

Inside the Playbook: Jared Cotter on How to Build a Team Around a Superstar

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 Syys 202520min

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