6x Grammy Winner Derrick Milano on How the Music Business Really Works for Songwriters

Grammy-winning songwriter and artist Derrick Milano knows how to turn life lessons into hit records. Sitting down for an in-depth conversation with Ray Daniels on The GAUDS Show, Milano opened up about the realities of the music business, the delicate balance between being a songwriter and an artist, and the importance of staying grounded while navigating an unpredictable industry.

Over the course of the candid interview, Milano covered everything from working with legends like Nicki Minaj and Beyoncé to breaking down the ways songwriters are often undervalued — even while penning chart-toppers. His reflections revealed a thoughtful, self-aware artist who has learned how to move with intention in a business that often pushes creators to chase trends and quick wins.

An Early Foundation of Identity and Perspective

Though now based in Los Angeles, Milano’s roots are in Philadelphia and Delaware, where his upbringing shaped the way he approaches music today. Raised in a two-parent household, Milano explained that his connection with street rappers and harder-edged artists came not from pretending to be something he wasn’t, but from understanding the shared experiences that cut across different backgrounds.

“I always tell them, treat me like the cool homeboy in the studio who’s just extra good at rapping,” he said. For Milano, writing music isn’t about promoting violence or glorifying negativity, but about bringing anthemic, universal energy to a record. “We’ve got to make music that the women and the world can feel — not just spinning the same stories.”

That perspective has allowed him to collaborate seamlessly with a wide range of artists, from pop icons to street rappers, without sacrificing his authenticity. “It’s about helping artists elevate and grow in their mindset — not just repeating the same thing,” he added.

Walking the Line: Artist or Songwriter

Throughout the conversation, Milano spoke openly about one of the most difficult challenges for many creatives in his position: balancing life as a songwriter with ambitions as an artist. “When I record my music, it comes from a real place,” he said. “It’s personal — it’s how I process what I’m going through.”

Unlike writing records for others, which often calls for formulaic hooks or catchy concepts, creating his own music means being vulnerable. “I’m a Capricorn — I don’t speak out a lot. But when I get on that microphone, that’s when you’ll know where I’m at mentally,” Milano said. “That’s the only time I can really say how I feel.”

He also stressed that collaboration doesn’t threaten his authenticity. If another writer can bring value to a record, he’s open. “It doesn’t matter who contributed — whatever’s best for the record.” In a business where egos often get in the way, Milano’s willingness to focus on the song first stands out.

Lessons from the Major Label Game

One of the sharpest parts of the interview came when Daniels and Milano dissected how major labels often maneuver when signing songwriters. Too often, labels sign hot writers not to develop their careers, but to use them as leverage to attract or feed other artists.

Milano experienced this firsthand during a major label deal that ultimately proved disappointing. “How they wanted to roll it out was to talk about all the songs I’d done for other people,” he recalled. “Respectfully — that’s not how I got to where I’m at.”

The experience taught Milano the importance of knowing when to say no — even if it risks short-term relationships or checks. “I told my team, I’m not writing for nobody right now. I’ve got to put myself first,” he said. Rather than chase clout, Milano stepped back to protect his artistry.

Respecting the Songwriter’s Role

Milano also didn’t hold back when asked about how the industry treats songwriters — particularly around money and recognition. “You can be a hit songwriter and still be struggling,” he said. “But an average producer will be thriving, because they’re getting paid upfront.”

He broke down a familiar cycle: writers often don’t see income for 12 to 18 months after a song is released, if the splits are even handled correctly. Meanwhile, producers often receive fees from day one. “That’s how they keep writers in these predatory deals,” Milano said.

For Milano, standing on your value as a songwriter is key. “If you bring the production, write the song, come up with the concept — you deserve to get paid,” he said. He also made it clear that he respects the role of engineers in crafting a song, often giving them publishing percentages because “we’re a team.”

Key Moments: Nicki Minaj, Beyoncé, Madden, and Rhythm & Flow

Milano’s career has been defined by moments where preparation met opportunity. One such moment came when Nicki Minaj embraced his artistry after working together on “Hot Girl Summer.” “She wanted to sign me and do a label deal,” Milano revealed. “She didn’t just see me as a writer.”

Another key moment came when he was handpicked to contribute to a Beyoncé remix — an opportunity that grew out of his unique sound and readiness to show up with something different. “I wasn’t trying to do a ballad — I came with uptempo energy, and it stood out,” he said.

Milano also detailed how a chance appearance at an Interscope athlete-artist summit led to an executive producer role on the Madden NFL soundtrack. “I didn’t have a plan, but I pulled up prepared,” he said. “That opened so many doors.”

Similarly, working on Netflix’s Rhythm & Flow gave him a platform to show how he develops emerging artists — something he sees as essential to building a legacy. “It’s missing in the industry. Artist development matters,” he said.

Moving Forward with Intention

Now at a pivotal point in his career, Milano is moving with a new level of purpose. After learning from past industry missteps, he’s focused on locking in a new artist deal — but on his own terms. “This time, I ask questions. I understand the business now,” he said.

Reflecting on one of his lowest points — when a major deal soured — Milano shared how writing down his goals helped him reset. “Once you write it down, it becomes your accountability partner,” he said. “And I hit everything on that list.”

With a trusted team around him and a clear vision, Milano is positioning himself not just as one of the game’s top writers, but as an artist with his own voice. “I’m so used to earning everything. Nobody gives me anything,” he said. “But when people do believe in me, I’m ready.”