Title: The Unbreakable Bond: Jessie Reyez and Byron Wilson Reveal How They Conquered the Music Industry Together

When Jessie Reyez and her longtime manager Byron Wilson sat down for an interview, what unfolded was more than just a story of success in the music industry; it was a story of trust, resilience, and the unbreakable bond that propelled them to incredible heights. Jessie and Byron revealed how their partnership, spanning nearly a decade, evolved from early struggles to success on the global stage. This interview peels back the layers of an artist-manager relationship and demonstrates how their journey together was built on understanding, perseverance, and a shared desire for greatness.

Trust Issues, Lessons, and Understanding the Industry

When asked why it was so important for her to understand the music business, Jessie Reyez didn’t hold back: "Trust issues," she said, simply. "You grow up, and you hear so many horror stories about [expletive] going left. I was on the receiving end of it, and I believed a lot of it. I wanted to make sure I was educated in what I was walking into." This awareness of the potential pitfalls made Jessie seek out as much knowledge as possible about the business side of the industry. For her, understanding the intricacies of contracts, deals, and the power dynamics within the industry helped reduce the fear and uncertainty that often overwhelms new artists.

Byron Wilson, her manager, recognized Jessie’s dedication from the start. He was impressed not only by her talent but also by her determination to learn every aspect of her career. Byron spoke of Jessie as an artist who didn’t just want to create; she wanted to make sure she was in control: "The paranoia was what helped her figure out how this business operated. And to her credit, she's damn good at negotiation," Byron said, emphasizing how Jessie’s need to understand and own her narrative gave her an edge.

Building a Team That Fits the Vision

For Jessie and Byron, success was not only about music; it was about building the right team. Jessie shared how particular she was about the people she let into her inner circle, whether it was a band member or a crew member: "When we were building the band, I put them through the ringer before I let them in." She explained how she asked potential band members questions that some might consider invasive. Jessie needed to know their energy, their attitude when they were angry, and if they understood her vision. She wanted to avoid anyone who wasn't prepared for the intense work ethic she and Byron demanded.

"Comfort is a silent killer," Jessie declared. She wasn’t interested in comfort; she wanted growth—a sentiment Byron echoed. "She lives for getting out of her comfort zone," he said. And when Jessie finally decided to add a full band to her performances, it was because she trusted Byron's advice to take her live shows to the next level. This decision, though initially resisted, ended up being a major turning point in Jessie’s growth as a performer.

The Remix Project and the Start of the Journey

Their journey together started long before the Grammys and billions of streams. Jessie Reyez found her way into the music industry through the Remix Project, a Toronto-based nonprofit that offered free mentorship and access to recording studios for youth at risk. Byron first introduced Jessie to the program by simply posting about it on Facebook. She applied at the last possible moment, and from there, it was a whirlwind of late nights and persistence.

"The school would close at 10 p.m., and everyone would leave… except Jessie," Byron said. Jessie would stay behind, sometimes hiding until she knew everyone else was gone, so she could continue working. "That's the work ethic that I saw from the start—serious about this thing." Byron reflected on how Jessie’s dedication to honing her craft made it easy for him to see that she was a force to be reckoned with.

Breaking Out and Blazing a Trail

Jessie and Byron’s breakout moment came through their connection with Chicago rapper King Louie, which led to the creation of their track, "Living in the Sky." Jessie described her nervousness walking into the studio with King Louie, surrounded by well-known producers and artists. She took a chance and asked, "Do you want to jam?" Despite her nerves, Jessie picked up her guitar, and they began to play. It was moments like these, where Jessie took risks and refused to let fear hold her back, that set her apart.

"Chicago was the first place in the States to [expletive] with me," Jessie said, explaining how her connection with King Louie brought attention to her music before she had really gained traction in Toronto. From that initial collaboration, Jessie found herself traveling across the U.S., shadowing artists like Chance the Rapper and absorbing everything she could about commanding a stage. It was this grassroots growth, along with Byron’s strategic moves, that laid the foundation for her success.

The Bidding War, Label Negotiations, and Refusing to Settle

One of the most gripping parts of Jessie and Byron's story is the label bidding war that began after they released "Figures," one of Jessie’s most powerful songs. Byron recalled, "Within 24 hours of releasing 'Figures,' the entire world of the music business was hitting up our emails." But instead of rushing into a deal, they took their time—six months, to be exact—to figure out what they wanted, even as major labels clamored for Jessie’s signature.

"We needed to make sure that we weren't tying ourselves in a contract that I'd look back on and be disappointed about," Jessie explained. She described a key meeting with Sir Lucian Grainge, the CEO of Universal Music Group, as a moment of sheer determination. She insisted on one specific point that wasn’t in the contract, standing her ground with the head of one of the biggest music companies in the world. Her unwavering stance paid off: "He heard everything I said and agreed," Jessie shared. This negotiation exemplified her strength and confidence—qualities that have been crucial in shaping her career.

Building Trust and Growth Together

The dynamic between Jessie and Byron goes beyond artist and manager—they are partners who have learned from each other every step of the way. Byron spoke of Jessie’s growth over the years: "There was a time when she needed to be in every mix session, giving notes. Now, she knows when to step back and trust her team." It was a point echoed by Jessie, who said, "The only reason we've been able to do that is because of the trust we've been able to build."

Through challenges, setbacks, and countless late nights, Jessie and Byron carved their own path to success. Their story is a testament to what can happen when an artist and manager work in perfect harmony—pushing each other to be better, supporting each other through every obstacle, and refusing to settle for anything less than greatness.

Their partnership didn’t just help Jessie Reyez become a globally recognized artist; it set a new standard for what artist management can be when driven by trust, respect, and a shared hunger for success. "You have to let the people who are specialists in their field fly," Jessie said near the end of the interview. "Everyone I work with has proven themselves, and you have to let them be amazing." It's clear that Jessie Reyez and Byron Wilson have let each other be amazing, and that is why they are where they are today.

Watch the full interview here