Inside the Playbook: Jessie Reyez on The Best Advice to Capitalize on Momentum

Inside the Playbook: Jessie Reyez on The Best Advice to Capitalize on Momentum

Jessie Reyez joins Byron Wilson and myself to trace the rise of a movement, how the Remix Project in Toronto became a launchpad for global talent and real career growth.

From a last-minute application to life-changing studio sessions, we dive into the power of mentorship, community, and creative momentum. The conversation spotlights key moments—like early collaborations with King Louie and Chance the Rapper, that helped expand reach and reshape futures.

More than a music story, this is a testament to what happens when talent meets opportunity and why investing in people always pays off.

A conversation like this doesn't come cheap.


Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/2hAbFlAG4IT6uL0MTaZEQR?si=4a40xtKHSEKbCJWS_JwG0w


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

Episoder(261)

 Inside the Playbook: Shawn Desman and Managers on What Really Makes a Great Artist

Inside the Playbook: Shawn Desman and Managers on What Really Makes a Great Artist

What makes a great artist, and a great manager?In this conversation, Shawn Desman, Steve Zsirai, and Chad Walsh break down the traits that separate the good from the unforgettable. From delivering “th...

25 Sep 202514min

The Manager’s Playbook 040: Shawn Desman, Steve Zsirai & Chad Walsh - Drake’s Co-Sign, Fame, Sobriety, Social Media Strategy & Building a Comeback Team

The Manager’s Playbook 040: Shawn Desman, Steve Zsirai & Chad Walsh - Drake’s Co-Sign, Fame, Sobriety, Social Media Strategy & Building a Comeback Team

Shawn Desman’s story is one of highs, lows, and a powerful comeback. From topping the charts to stepping away from music, Shawn opens up about the pressure of fame, battling depression, and finding so...

23 Sep 20252h 1min

Inside the Playbook: Milana Lewis on What Artists Can Learn From Entrepreneurs

Inside the Playbook: Milana Lewis on What Artists Can Learn From Entrepreneurs

In this clip from The Manager’s Playbook, Mauricio Ruiz speaks with Milana Lewis (CEO of Stem) about her journey from having no background in music to becoming a leading entrepreneur in the industry.M...

22 Sep 202518min

Inside the Playbook: Milana Lewis on What Makes an Artist Stand Out

Inside the Playbook: Milana Lewis on What Makes an Artist Stand Out

In this clip from The Manager’s Playbook, Mauricio Ruiz sits down with Milana Lewis (CEO of Stem) to unpack the realities of artist development and partnerships in today’s music business.Milana shares...

21 Sep 202516min

Inside the Playbook: Milana Lewis on The Reality of Music Advances & Shelving

Inside the Playbook: Milana Lewis on The Reality of Music Advances & Shelving

In this clip from The Manager’s Playbook, Mauricio Ruiz sits down with Milana Lewis, CEO of Stem, to break down how Stem approaches artist partnerships and deal-making differently.Milana explains why ...

19 Sep 202510min

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 Sep 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 Sep 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 Sep 202518min

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