Features
Kehinde Ajose: The Business Side of Olamide That Deserves Your Attention
In Nigeria’s entertainment economy, where many stars burn bright and fade out in two or three years, Olamide has done the near-impossible: stay relevant, build wealth, and maintain influence for over a decade without using scandal as a marketing strategy.
To many, he is Baddo, the street’s music icon, a lyrical warrior, and a proponent of indigenous rap. But beyond the stage lights and swagger lies something far less visible: a razor-sharp business acumen
My first encounter with Olamide was in 2014 at a press conference organised by a Nigerian brewery brand to push one of their campaigns. He was soft-spoken, down-to-earth, and somewhat shy. It was a total departure from the electric Baddo on stage. My second encounter was in 2017 at Olamide Live In Concert (OLIC). For the first time in four years, he shifted the venue from Eko Hotel Convention Centre to Teslim Balogun Stadium, a strategic, crowd-focused move. It wasn’t just a concert; it was market expansion in action.
Fast forward to 2025, Olamide isn’t just relevant, but has transformed into a more measured and strategic artist. His portfolio reads like a business case study: mentoring and launching stars (Fireboy, Asake, Adekunle Gold, Lil Kesh), consistent product delivery (albums that captivate his fans and show his craftsmanship), high-profile brand deals and investment diversification.
In an honest conversation with YouTuber Korty EO, Olamide revealed lessons that every entrepreneur, creative, or business leader should study.
Think Like a Businessman, Not Just an Artist
In the interview, Olamide said, “I will pick being business-minded and being creative over just being creative and not being business-minded.”
For many creatives, the obsession is with the craft, writing the perfect song, shooting the most cinematic video, or delivering the cleanest design. But Olamide flips the script: the business determines whether that creativity survives. An artist’s mindset often focuses on making great art, then hoping the money will follow. A businessman’s mindset is: How do I generate income streams from this art? How do I reinvest profits to grow my brand?
This involves understanding market dynamics, negotiating wisely not only for upfront fees but also for royalties, equity, and residuals, and establishing infrastructure — as he did with YBNL — so that the brand endures beyond one individual. If you’re a founder, consultant, or artiste, the question isn’t just “Am I talented?” but “Do I have the systems to make my talent profitable?” Talent might open doors; business acumen decides if you stay in the building.
Treat Every Day Like Rent Is Due
“You have to constantly keep the fire in you burning. And the only way… is by accepting that rent is due every day”, Olamide said. As you know, this isn’t about rent in the literal sense; it’s a philosophy of urgency. Olamide understands that in entertainment, as in business, there is no lifetime achievement award for relevance. Yesterday’s win doesn’t pay today’s bills (well, not considering streaming royalties.)
For entrepreneurs, this means creating value every day, continuously adapting, and avoiding complacency—even after achieving significant successes. They should maintain the mindset of still having to earn their place. This is the same mentality that drives companies like Amazon, where Jeff Bezos advises employees to “always act like it’s Day 1.” For Olamide, every performance and every release is considered Day 1.
Evolve or Be Left Behind
“You can’t box me and call me a rap artist. I love music. If I want to do Fuji, Pop, or RnB, I will do it. I don’t care,” Olamide told Korty. His refusal to be boxed is not just artistic, it’s strategic. By staying genre-fluid, he widens his audience, remains unpredictable, and stays ahead of changing tastes.
This means that business owners must diversify their markets by expanding their offerings to serve new demographics, innovate authentically, and experiment without compromising their core identity. Additionally, they should future-proof their business by anticipating shifts in demand before they are forced to act. Olamide ensures he’s never trapped by a single market condition.
In my brand, one of the ways I evolved was to expand from written content to expanding to visuals (content creation). Evolving isn’t just about changing what you create; it’s about upgrading how you think about business. From pricing strategies to distribution methods, you must keep learning or risk being outpaced by those who do.
Build With People Whose Intentions Are Right
“Some people are loyal to you and not passionate about their work. Some are passionate but not loyal… For me, it’s about intentions.” Olamide values the “why” behind someone’s actions more than their resume or blind loyalty. This is a leadership lesson many ignore: intentions set the tone for execution.
In the corporate or entrepreneurial world, hire for alignment, not just skill, because skills can be taught; values can’t; watch for quiet sabotage because passion without loyalty can become a threat, and prioritise mutual growth. Work with people whose success is tied to yours. This is why YBNL’s alumni often speak positively of him even after leaving. He built relationships on trust, not control.
Stay a Student, Even as a Master
“I’m always surfing the internet just to acquire more knowledge.” Despite his achievements, Olamide doesn’t claim to have arrived. His curiosity is a business advantage, keeping him updated, informed and inspired. When you reach a high level, it’s easy to think you’ve arrived. But the moment you stop learning, your craft starts ageing. Staying a student means attending workshops, studying trends and learning from younger talents, even if you’ve been in the game for decades. In a market where trends can change overnight, the willingness to keep learning is your best hedge against irrelevance.
Legacy is not built in the noise; it’s carved quietly, in the discipline of daily execution. The real Olamide’s achievement is not just numbers or flashy deals. It’s the silent, steady growth. The ability to sustain, evolve and empower others while keeping the fire burning year after year. Olamide’s legacy is not built on spectacle, but on substance. He proves that street wisdom, discipline, and business sophistication can coexist. And that the power to transform an industry lies in strategy, empathy, and a relentless drive to serve a bigger purpose.
