Welcome to The Manager’s Playbook, my personal newsletter where I share insights from Music Executives and Artists for aspiring and emerging music managers, executives and artists on how to navigate the music industry. This newsletter is brought to you by Mauricio Ruiz.

Ruiz Note:

The Truth About Living in Your Vocation

She’s the type of artist who doesn’t need to tell you she’s all heart—it’s undeniable in everything she does. Whether it’s in her raw, soul-baring lyrics, her electrifying performances, or her commitment to staying true to herself, Jessie Reyez exudes authenticity. In an industry that often pressures artists to conform, Jessie stands out as someone who lives and creates unapologetically, without seeking approval or validation. That’s what makes her artistry so powerful—it comes from her truth.

I can speak honestly about her trajectory because I’ve witnessed her rise firsthand—as her former co-manager, I have seen the impact she has had on everyone who is fortunate enough to collaborate with her.

Jessie didn’t just enter the music scene; she burst into it with fire, determination, and a voice unlike any other with her debut single ‘Figures’. With her breakout single she captured the hearts of millions and established herself as one of the most unique voices in music today. Wether its penning Cavlin Harris & Dua Lipa’s MEGA-SMASH ‘One Kiss’ or writing LISA’S latest single ‘Moonlit Floor’ that’s garnered 100 million streams in less than a month or Jessie’s own banger ‘Ridin’ with Lil Wayne , Jessie has consistently proven herself as a force in this industry.

It’s not just her sound, though.

It’s the way she channels her pain, her joy, and her lived experiences into songs that resonate deeply. She doesn’t just write music; she creates moments that remind people they’re not alone. Her ability to tap into raw emotion and turn it into globally resonant hits is unmatched.

But Jessie isn’t just a gifted artist—she’s also a sharp strategist and businesswoman who understands the importance of building a career with intention. Behind the scenes, Jessie works tirelessly to shape her creative vision while ensuring every aspect of her career operates at the highest level.

Behind every successful artist is a team of people who believe in their vision as much as they do.

For Jessie, one of the those people is Byron Wilson and the other was myself. Having worked alongside both of them for over a decade, I’ve had the privilege of seeing this journey up close. The triumphs, the challenges, and the countless decisions that shaped her career. Byron, with his steady hand and business savvy and my commitment to the creative and business side of her career aligned with her values, she became a somewhat not to be played with.

In this episode of The Manager’s Playbook Podcast, Jessie, Byron and I pull back the curtain on what it took to build and sustain a career like hers.

Here are 10 key takeaways from the episode with Byron Wilson and myself, complete with examples from our decade of working with Jessie Reyez that I’ve observed:

1. Authenticity is Your Greatest Asset

   • Jessie built her career by staying unapologetically herself. For example, her breakout single Figures wasn’t crafted to chase trends—it was raw, emotional, and deeply personal. That authenticity resonated, creating a strong foundation for her career.

2. Trust the Team You Build

• Byron and I worked closely with Jessie to make tough decisions, but the key was trust. For instance, when we decided to turn down a lucrative but misaligned deals and opportunities early in her career, Jessie trusted the team’s judgment, prioritizing long-term alignment over short-term gains. Remember, its more important what you say no to vs what you say yes to.

3. Have a Clear Vision for Your Brand

• From the beginning, Jessie’s brand was rooted in vulnerability and fearlessness. Her visuals, like the powerful music video for Gatekeeper, were deliberate choices to tell her story in a way that amplified her message and identity. Remember, this also means you are allowed to be selfish. It is perfectly normal to not always up for the challenges of being in the spotlight. Take your down time, acknowledge the weight of this career. You are only human!

4. Be Strategic About Relationships

• Jessie didn’t collaborate just for clout—she chose partnerships that aligned with her artistry. For example, working with Eminem on Good Guy was a natural fit, not just because of his platform, but because their raw, lyrical styles complemented each other.

5. Be Selective With Labels and Deals

• Jessie’s team carefully evaluated deals to ensure she maintained creative control. When she signed with Island Records, it was because they believed in her vision rather than trying to mold her into something she wasn’t.

6. Use Visual Storytelling to Elevate Your Art

• Jessie’s music videos, like Figures and Shutter Island, weren’t just promotions—they were extensions of her songs. Each video added depth to the story, creating a full artistic experience. This is where my visual storytelling background came into play, ensuring she had the best visual storytellers match her music’s emotional impact.

7. Tough Conversations Are Necessary

• Some of the most pivotal moments came from difficult discussions. For instance, when Jessie was overworked from back-to-back tours, we had to step in and prioritize her health—even when it meant rescheduling opportunities.

8. Play the Long Game, Not the Short Game

• Early in her career, Jessie could have easily gone for a viral moment or a trendy feature, but instead, we focused on building her foundation. The slow-and-steady approach helped her not just survive but thrive in the long run.

9. Stay Resilient in the Face of Fear

• Jessie’s fearlessness has always been one of her defining traits, and it shows in moments both big and small. One story that stands out is when she first met King Louie. Instead of overthinking or holding back, Jessie pulled out her guitar and started playing music on the spot. She didn’t wait for permission or overanalyze whether it was the “right” time—she let her art lead the way. What came from that was a dope song, a strong bond between the two and a community in Chicago for Jessie. A reminder that greatness can come from putting yourself out there!

  

  Jessie Reyez & King Louie (Toronto 2015)

10. Create From a Place of Purpose

• Jessie’s music has always been more than just songs—it’s a way to connect with people on a deeper level. For instance, Gatekeeper wasn’t just a song; it was a powerful commentary on the realities of sexism in the music industry, sparking important conversations globally.

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-Ruiz

Bio

I’m Mauricio Ruiz, the Founder/CEO of 8 Til Faint, an Artist Management company with over 5 billion audio streams worldwide. Our past and current clients include Grammy nominated, Juno Award winning multi-instrumentalist and singer/songwriter Jessie Reyez, Marley Bleu, Skratch Bastid and more. I am also the Co-Founder of Mad Ruk Entertainment, a content agency with over 3 billion long form video streams worldwide. Our client list includes The Weeknd, Eminem, and Celine Dion, along with renowned brands like Nike, Pernod Ricard, Canon, and the NBA.

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