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: Steve Rifkind on How He Invented Street Teams

Inside the Playbook: Steve Rifkind on How He Invented Street Teams

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Inside the Playbook: Steve Rifkind on The Street Team Strategy That Built Hip-Hop Fans

Inside the Playbook: Steve Rifkind on The Street Team Strategy That Built Hip-Hop Fans

In this clip, Steve Rifkind breaks down the year he spent managing New Edition, and why it became his real-world education in the music industry. From meeting key players like Lady B, Hiriam Hicks, an...

23 Jan 18min

The Manager’s Playbook 051: Steve Rifkind - Loud Records, Street Teams, Wu-Tang Clan, Akon & Record Label Strategy

The Manager’s Playbook 051: Steve Rifkind - Loud Records, Street Teams, Wu-Tang Clan, Akon & Record Label Strategy

Steve Rifkind helped build the modern music business playbook, and he’s one of the people who created and popularized “street teams” before anyone had a marketing department to hand it to.In this epis...

20 Jan 2h 35min

Inside the Playbook: Mike Biggane on Why Artist Development Is Now the Manager’s Job

Inside the Playbook: Mike Biggane on Why Artist Development Is Now the Manager’s Job

The music didn’t get worse. The way it travels changed.In this clip from The Manager’s Playbook, Mike Biggane and I unpack why hits feel smaller in the streaming era; not because of talent, but becaus...

19 Jan 13min

Inside the Playbook: Mike Biggane on Why the Current Music Industry Is at a Turning Point

Inside the Playbook: Mike Biggane on Why the Current Music Industry Is at a Turning Point

Most conversations about streaming focus on artists or platforms.This one starts where the pressure shows up first: songwriters, publishers, and the economics underneath the music.In this clip from Th...

18 Jan 21min

Inside the Playbook: Mike Biggane on Why Record Labels Don’t Build Artist Careers Anymore

Inside the Playbook: Mike Biggane on Why Record Labels Don’t Build Artist Careers Anymore

The music industry didn’t pivot because of trends. It pivoted because the returns disappeared.In this clip from The Manager’s Playbook, Mike Biggane unpacks why major record labels quietly changed the...

17 Jan 13min

Inside the Playbook: Mike Biggane on Why Playlists Don’t Break Artists Anymore

Inside the Playbook: Mike Biggane on Why Playlists Don’t Break Artists Anymore

Before playlists became leverage, before algorithms dictated discovery, before release strategy turned into guesswork, there was New Music Friday.In this clip from The Manager’s Playbook, Mike Biggane...

16 Jan 28min

The Manager’s Playbook 050: Mike Biggane - Spotify, Personalization, Artist Development & The New Music Business

The Manager’s Playbook 050: Mike Biggane - Spotify, Personalization, Artist Development & The New Music Business

The music industry didn’t slowly evolve. It structurally changed.And most people are still trying to operate inside a version of the business that no longer exists.In this episode of The Manager’s Pla...

13 Jan 2h 14min

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