We revisit the origin story of Jessie Reyez’s breakout hit “Figures” from a chance car ride in Sweden to a full-blown industry bidding war.

It’s a behind-the-scenes look at how one song sparked a movement, shifting careers and commanding attention across major labels. We explore the key moments that shaped the journey: gut decisions, hard conversations, and the conviction it takes to bet on yourself.

This clip also unpacks the artist-manager relationship and the non-negotiables that shaped Jessie’s path: authenticity, respect, and control. A powerful story about creative instinct, industry leverage, and building with integrity.

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

Jessie Reyez and Byron Wilson take you deep into the real-life dynamics of the music industry, from conflict resolution to creative breakthroughs.

We explore how mastering communication, sometimes just picking up the phone, can break down barriers.

The conversation highlights the power of sequencing, the evolution of song ideas, and what really happens behind the studio doors when flexibility meets pressure.

But it’s not just about the work. We dig into the psychology of success: fear, self-doubt, and what it means to push past internal limits. The importance of community, rest, and finding clarity,especially during moments like the COVID-19 pause, round out this candid, high-impact session.

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

In this clip, Director X unpacks the creative mindset behind some of the most iconic music moments of the last decade, from Hotline Bling to Life is Good.

Through real stories involving Drake, Jay-Z, and Justin Bieber, we explore why holding onto your best ideas can cost you, and why “Don’t get too precious” might be the advice that changes your approach to creativity for good.

This is more than a behind-the-scenes look. It’s a deep dive into collaboration, adaptability, and the quiet genius that turns constraints into classics.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/6JvlRp7G633z77Vvk34jHN?si=z9Dj1Qr4RzGmUEmTZrjRSQ

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

In this episode, Nick Raphael gets real about one of the biggest misconceptions in the music industry: talent alone doesn’t break artists. Effort does.

We explore why consistent output, audience building, and a clear narrative are just as important as the music itself. From early-stage grind to honest assessments of follower counts and streams, Nick lays out what readiness really looks like.

With stories of Adele, Sam Smith, and Frank Ocean, this episode is a blueprint for anyone trying to turn skill into success.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/4g8IgvdCYzvpVPHiKUXS43?si=ietm7srSRX6hQv9Nt5nh6Q

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

Before the billion-dollar empire, Jay-Z was just an overlooked artist with a brilliant album, and no U.S. label willing to take the risk.

In this episode, Nick Raphael, former President of Capitol Records UK, shares the inside story of how he and Christian Tattersfield signed Jay-Z in 1996 from a small office in London. It’s a raw look at what it means to trust your instinct and bet big when everyone else says no.

Nick walks us through the unconventional journey: cold-calling Damon Dash, researching Jay’s buzz through record shops, and watching an artist turn early rejection into generational leverage. It’s a powerful reminder that vision, grit, and timing still matter more than hype.

This is how legends are made, and why most execs missed it.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/4g8IgvdCYzvpVPHiKUXS43?si=ietm7srSRX6hQv9Nt5nh6Q

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

In this episode, Nick Raphael, former President of Capitol Records UK, pulls back the curtain on what actually makes or breaks an artist’s career.

It’s not just about talent. It’s about having the right manager, the right strategy, and the ability to build meaningful connections. Nick unpacks why likability often beats raw skill, how inexperience at the management level can derail momentum, and why major labels still play a vital role in breaking global acts.

We also get into the concept of “concentric circles” of influence, and why your team’s reach, experience, and credibility matter more than you think.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/4g8IgvdCYzvpVPHiKUXS43?si=ietm7srSRX6hQv9Nt5nh6Q

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

In this episode, Nick Raphael, former President of Capitol Records UK, uncovers a core truth of the music business: a hit record means nothing without the right artist.

We dive into why some tracks never break through, even when they’re brilliant, and why fan connection, team alignment, and timing can turn a decent song into a global moment. Nick shares the story behind Empire State of Mind, explains how artist-first thinking drives success, and reveals the deeper strategy behind building lasting careers.

Plus, we explore the rise of the independent middle class in music and how Nick’s latest venture is redefining what a modern label can look like, with a tight team and big results.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/4g8IgvdCYzvpVPHiKUXS43?si=ietm7srSRX6hQv9Nt5nh6Q

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

In this episode, legendary filmmaker Director X breaks down how to cut through the noise in a content-heavy world, and why the best visuals aren’t always the most expensive.

From using real locations and dynamic transitions to anchoring every shot in emotional truth, X reveals how resourceful creativity wins. But beyond technique, this episode is a deeper dive into the mindset behind iconic visuals.

We trace X’s journey from comic book dreams to directing for Jay-Z and beyond, exploring how fear, persistence, and pure passion shape a creative career. It’s a blueprint for anyone looking to make meaningful work and stay inspired in an industry that never slows down.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/6JvlRp7G633z77Vvk34jHN?si=z9Dj1Qr4RzGmUEmTZrjRSQ

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

In this episode, legendary music video director Director X breaks down the role of music videos in 2024, and why they still matter in a world dominated by streamers and short-form content.

From drawing out deeply personal performances from artists like Usher and Zayn to recounting the untold stories behind shelved big-budget productions, X shares what really happens behind the lens. He also reflects on how the industry shifted from extravagant productions to refined, intentional storytelling, and what that means for artists today.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/6JvlRp7G633z77Vvk34jHN?si=z9Dj1Qr4RzGmUEmTZrjRSQ

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

Ruiz and Byron take you on a journey through the discovery and management of the phenomenal Jessie Reyez. It all began in 2013 with a serendipitous Facebook connection that led to an unexpected musical spark.

They share the thrilling tension of first hearing Jessie's raw talent, her voice so unique, Ruiz, then manager of Jessie and now host of The Manager’s Playbook Podcast, initially hesitated to share it.

As they reflect on their evolving bond with Jessie, they recount pivotal moments like the release of her soul-stirring anthem Figures, a track they knew would disrupt the industry. Dive into the behind-the-scenes moments that shaped Jessie's rise, as they reveal the relentless belief that fueled their journey and Jessie's path to stardom.

Listen to the full episode here -

Spotify:

https://open.spotify.com/episode/31MpAcVnF0tgKN0s7gXQuy?si=jJFVNrWrQfmaxBkHZ8HyzA

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