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Questioning the Status Quo: How Keishia McLeod Plans to Shake up the Music Industry

What started as a simple question about woes in the music industry has led Keishia McLeod to a plan to change the standard artist representation model.

While having a chat with Keishia McLeod, CEO of Legacy Records, about her views on life, business, and the music industry, I found myself continuously coming back to a quote from a slam-poet friend of mine. After an evening of his readings, someone in the crowd had asked why he had ended a piece as a question.

“Questions generate energy,” he had said. “Statements provide closure, but questions generate energy.”

I think about that quote often. In the case of Keishia managing the helm of Legacy Records as they carve out their own space in the music industry, I can’t help but see how it provides light into the spark behind a business venture.

Why? A simple question that created so much energy.

The entire vision comes from hearing people’s pain points who are currently in the industry.

“I’m always aware of making an opportunity out of things,” said Keishia when I asked about Legacy’s choice to break into the music industry. They began the year hosting an event at the Music Lodge for Sundance 2020 in Park City, Utah. Legacy’s background had mostly involved visual media formats, from comic books to producing shows for streaming services such as Netflix, until 2020 and COVID shut down Hollywood. 

“No one was even allowed to show up on set and everything was put on hold. We were just getting ready to bring on a bunch of really talented artists from Marvel, DC and Pixar.” Rather than sitting and waiting, however, Keishia saw the opportunity in what was still moving: the music industry.

“We were stopped by forces we couldn’t control,” she said, regarding the shutdown, “And, in the stillness, it dawned on me: music never ends. It’s the one thing that has been with us through all our best times and there for us through our worst. No matter what happens in the world it can’t be affected and it’s something we can all connect with.”

Opportunity only went so far in the decision for the pivot, however. In the end, one of the strongest motivating factors was in the name of the company itself: legacy, to leave behind something that lasts.

We may ruffle some feathers, but we’re going to take this industry and give it a pivot.

“While discussing the music industry with friends of mine who are talented musicians,” said Keisha, “They generally had a sense of how cruel the industry can be. I asked myself, ‘Why is it this way?’ When something doesn’t seem right, I ask why- you should always ask why. Why is ‘signing your life away’ a thing in the music industry, and why can’t it be changed? I just don’t like that phrase and I don’t want Legacy’s Artists referring to their label that way.”

With these plans, Keishia’s mindset boils down to one concise belief: Just because the music industry is big doesn’t mean it’s invincible.

“Every few years, industries undergo a great pivot,” said Keishia, harkening to the way cell phones transformed the telecommunication industry, or how Netflix has—and still currently is—transforming the film industry. “We haven’t seen that yet in this industry, but it’s coming. We’re going to be a large part of making that happen. I can’t yet speak to the technology behind it and the financial benefits to our artists but again we’ve found and created solutions to my why’s. We’ve attracted some of the best people in their fields. We’re all on the same frequency and I’m so proud of our team.

“It’s all so much larger than just music. We’re going to change the industry. I feel like there’s a box—this is what the music industry does at this point. We’re going to throw away that box and say: This is what the music industry can do. Legacy has arrived on scene, and we’re here to do things different. To do things right.”

All of that ground shaking energy, from something as simple as a single word question: “Why?”

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