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 Caribbean roots and church upbringing shaped her approach to managing Grammy-winning talent like Lucky Daye, Dee Mile, and Camper, and how she co-founded Good Company Records with the Walt Disney Group.


Discover the untold stories of navigating the highs and lows of the music business, advocating for artists in an often-overlooked industry, and witnessing musical greatness alongside icons like Ne-Yo and Harmony Samuels. Natalie opens up about her early days in artist management, the emotional toll of social work, and the bold decisions that propelled her career forward.


Packed with hard truths, invaluable lessons, and behind-the-scenes insights, this episode is a must-watch for aspiring managers, music enthusiasts, and dream-chasers alike. See why Natalie Prosper is redefining leadership in music and learn what it takes to build a lasting impact in the industry.

Episoder(259)

Inside the Playbook: SonReal on How Content Actually Grows Music

Inside the Playbook: SonReal on How Content Actually Grows Music

The “mysterious artist” era worked when the music business was built around blockbuster music videos and gatekeepers. Today it’s algorithmic, short-form, and driven by consistent distribution.In this ...

14 Feb 13min

 Inside the Playbook: SonReal on The Strategy Behind Viral Artists

Inside the Playbook: SonReal on The Strategy Behind Viral Artists

Most independent artists don’t struggle because they can’t make music fast.They struggle because they can’t make the pace financially sustainable.In this clip, SonReal breaks down a modern independent...

13 Feb 13min

The Manager’s Playbook 054: SonReal - Independent Artist Strategy, Owning Your Masters, 2-Week Release Schedule, Content Systems & Touring Profitably

The Manager’s Playbook 054: SonReal - Independent Artist Strategy, Owning Your Masters, 2-Week Release Schedule, Content Systems & Touring Profitably

There’s a whole middle class in the music industry.Artists who aren’t household names, aren’t living off viral moments, and aren’t waiting on label permission, yet they’re making real money, building ...

10 Feb 1h 50min

Inside the Playbook: Sickick on Reinventing His Sound to Build Longevity

Inside the Playbook: Sickick on Reinventing His Sound to Build Longevity

TikTok can give you momentum. The real question is whether you can turn that momentum into a career with identity.In this clip from The Manager’s Playbook, Sickick breaks down his evolution from dark ...

9 Feb 8min

Inside the Playbook: Sickick on What Good Management Actually Feels Like

Inside the Playbook: Sickick on What Good Management Actually Feels Like

In the music business, careers don’t usually break because of bad songs. They break because team dynamics fail.In this clip from The Manager’s Playbook, Sickick breaks down what healthy artist managem...

8 Feb 5min

Inside the Playbook: Sickick on The Truth About Reinventing Yourself as an Artist

Inside the Playbook: Sickick on The Truth About Reinventing Yourself as an Artist

TikTok can give you attention fast. It can also box you in even faster.In this clip from The Manager’s Playbook, Sickick breaks down the real arc behind the “TikTok DJ” label, how remix momentum and a...

7 Feb 15min

Inside the Playbook: Sickick on How Bad Management Almost Ended His Music Career

Inside the Playbook: Sickick on How Bad Management Almost Ended His Music Career

In the music industry, careers don’t usually fall apart because of bad music. They fall apart because of bad management, broken systems, and artists not understanding their own business.In this clip f...

6 Feb 11min

The Manager’s Playbook 053: Sickick - Bad Artist Management, Ownership, Content Strategy & Career Longevity

The Manager’s Playbook 053: Sickick - Bad Artist Management, Ownership, Content Strategy & Career Longevity

In the music industry, talent is never the only factor.Management is, systems are, ownership is and the ability to understand your own business before someone else understands it for you.In this episo...

3 Feb 54min

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