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.

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Inside the Playbook: Steve Rifkind on How He Negotiated Wu-Tang’s Deal with a CHAIR?!?

Inside the Playbook: Steve Rifkind on How He Negotiated Wu-Tang’s Deal with a CHAIR?!?

Steve Rifkind breaks down the behind-the-scenes reality of Wu-Tang Clan’s record deal negotiations, the kind of label-room pressure that shapes careers, catalogs, and legacies.In this clip, Steve walk...

25 Tammi 17min

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

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

Steve Rifkind breaks down one of the most important “from nothing to systems” stories in the music business. With just $5,000 to his name, he invests in a simple booklet and turns it into real leverag...

24 Tammi 17min

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 Tammi 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 Tammi 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 Tammi 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 Tammi 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 Tammi 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 Tammi 28min

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