Ayoade ‘KJ Sheggs’ Olusegun is a serial entrepreneur, brand strategist, and technology innovator with over a decade of experience operating from Ibadan, Nigeria. He is the founder of Nairoke Entertainment, a company that revolutionised the Nigerian karaoke industry and GuessWhot Solutions, a strategy, execution, and digital products company that leverages AI to build scalable solutions. He was also the Chairman of the Implementation Committee for the inaugural Oyo State Digital Summit in 2024, which trained over 5,000 young people in digital skills. He is also the convener of ‘Vibe Coding with KJ Sheggs’, a free training initiative that teaches people how to build digital products without coding using AI. In this exclusive interview with Rotimi IgE, Ayoade speaks about his love for Ibadan, the challenges of the tech ecosystem, his guiding philosophy, and why he believes the future of African innovation starts at home.
You have been in the Ibadan entrepreneurial ecosystem for over a decade. Given that Lagos is often seen as the go-to place for business, and many people build projects in Ibadan only to move them to Lagos, what has motivated you to remain consistent in this ecosystem?
One of my favourite lecturers at the University of Ilorin hammered a four-word quote into my head: Think global, act local. Ibadan is my home. I’m an indigene of this ancient city, and the biggest global successes are those who are locally relevant but able to play on the global stage. My focus has always been on building at home, building solutions for my immediate environment. Ibadan has a population of over 3.5 million people, and Oyo State has over 6 million. We have the numbers, we have the market; we just need to build the right products.
Historically, Ibadan has always been the epicentre of entertainment and technology in Nigeria. The frameworks have always existed; we are just plugging into them. I see Ibadan as the next frontier, and that’s why I’m committed to building here.
How did you start being inclined towards this entrepreneurial music and tech journey? Tell us about your formative years and early influences.
I think one of the most fortunate things that ever happened to me was that I was born in Ibadan. Growing up, I had the pleasure of being raised by entrepreneurial people around me, most notably my mother. She had a small shop, and I had the special role of going to the bakery to buy bread. Sometimes, people on the road would call to order, and I’d have sold out before getting home. Instead of going back empty-handed, I would go to the bakery for another batch, making double the sales. So from a very young age, I was able to make business decisions that made sense to the bottom line.
After university, I had a number of ventures; some enjoyed brief successes, but many of them failed. I like to say that the biggest successes are also built on the biggest failures. When I founded Nairoke Entertainment, which focused on building Nigerian karaoke tracks for entertainment outlets, it only made sense to do it in a city with so much entertainment history. The karaoke industry back then was over a $50 billion industry globally, but we had less than a thousand Nigerian songs on those platforms. What we did was highlight the beauty and energy of singing Nigerian songs, and it revitalised the karaoke industry across the country.
In 2016, I was selected as one of the winners of the Tony Elumelu Entrepreneurship Programme. Out of over 45,000 applicants, only 1,000 were selected. The funding helped us invest in equipment and manpower, which allowed us to scale the business across the Southwest.
At the height of it, the entertainment opportunity pivoted into production and management, expanding knowledge by learning under great entertainment names as Godwin Tom, Yemisi Falaye, among others. I had the opportunity to travel and work on productions for major artistes, including Wizkid and Davido, learning firsthand from industry veterans, Kaycee Oguejiofor and Ademiluyi Sarumi. That experience allowed me to contribute meaningfully to projects across the country, working with artistes like Seyi Vibez, Bella Smurda and Seyi Vibez. It was an incredible period of growth, and it cemented my understanding of the entertainment industry from the inside out.
You played a significant role in the Oyo State Digital Summit in 2024. Can you tell us about that experience and what it meant for the state?
That was a landmark moment for me and for Oyo State. I was honoured to serve as the Chairman of the Implementation Committee for the inaugural Oyo State Digital Summit. Over two days at the International Conference Centre in Ibadan, we trained over 5,000 young people in digital skills that matter. We covered AI prompt engineering, web development, digital marketing, and more.
The theme was ‘Skills to Bills’, and it was about transforming youth potential into economic power. We brought in development partners, we had private sector involvement, and we created a five-month mentorship program that extended beyond the two-day event. It was the first time the state government had done something of that scale, and it worked. For me, it was proof that when government, private sector, and community stakeholders come together, we can create real, tangible change.
This wasn’t just training for training’s sake, it was about economic empowerment. The goal was to move young people from “skills to bills”, to give them capabilities that translate directly into income.
The programme was the Oyo State Agency for Youth Development and private sector partners. Looking forward, we can engage over 500,000 youth annually through various initiatives. This would help us increase capacity among residents, accelerate development, create support systems and infrastructure and scale innovation in the state. We can also partner with brands that share the same positive vision for our state, the youth and the country.
How do you think the private sector could benefit from leveraging the next Oyo Tech Summit?
I believe it goes beyond CSR. It’s strategic. Companies can get direct access to a pipeline of job-ready youth, saving them N5 to N15 million in recruitment and training costs. They can get over four million impressions across digital and physical touchpoints, which is equivalent to N20 to N40 million in traditional advertising. They can also document real social impact with government validation, which would be good for their sustainability outlook. Furthermore, they can receive direct insights into the youth market, which would serve as invaluable intelligence for any brand targeting young people.
I believe both innovators, the government and the private sector, need to work more robustly and intimately. It’s about creating an ecosystem where everyone wins. The government provides the platform, the private sector provides the resources and opportunities, and the youth get the skills. That’s how you build a sustainable economy.
How did you get involved in this government work, and what does it mean for your personal brand?
It’s humbling. I’ve been building in Ibadan for over a decade. When the government started looking for people who understood the digital and creative space, my name came up because of the work I’d done with Nairoke, with GuessWhot Solutions, and with various community initiatives. It’s a testament to what happens when you stay consistent and deliver value.
What it means for me personally is that I get to help shape the narrative. I get to be part of the solution, not just talk about the problems. And I get to use my platform, my brain and my people to catalyse change. That’s my guiding philosophy, really: I am uniquely positioned to be a catalyst to help people become the best versions of themselves. Whether it’s through government programs, my own businesses, or initiatives like ‘Vibe Coding with KJ Sheggs’ the goal is the same, building capacity and building people.
How do you see yourself and your ventures in the next five years?
My goal for the digital part of GuessWhot Solutions is ambitious. I want to build a thousand apps. I want 30 per cent of them to have local relevance, 15 per cent to have regional relevance, seven per cent national, three per cent continental, and one per cent global relevance.
To achieve this, I need partners and ideas. To solve the challenge of building them alone, I launched a free training program called ‘Vibe Coding with KJ Sheggs’ to train people and build together. To solve the challenge of marketing them alone, I’m pivoting from individual projects to partnering with different organisations who want to build products for their communities.
The third edition of Vibe Coding with KJ Sheggs is happening this Sunday, June 28th, and forthnightly subsequently. It’s completely free. We use AI to build websites, apps, chatbots, automations, and skills. No technical background is needed, just curiosity. Past students with zero coding background have built projects like Okada Med-Reach, a platform connecting motorcycle riders to emergency medical services, Pixel Perfect Clone, a UI/UX design replication tool, and SnapBite Fast Meals, a quick-order food delivery mini-app. These started as ideas; two hours and the right tools later, they were live.
Ige: What challenges do you and other young tech innovators face in the country, and what solutions do you propose?
Ayoade: The usual Nigerian challenges persist: power, expensive internet, and a lack of structured funding and grants. But the biggest challenge, for me, is integrity. So many people have been burned by failed partnerships that it’s difficult to trust again. Instead of building skyscrapers by combining strengths, everyone wants to stand on their own, building silos instead of long-term legacy infrastructures. If you want to run fast, run alone; if you want to run far, you have to go with people.
For solutions: we need more creative sector education, more professionals who serve the creative industry, legal and finance experts who understand entertainment sector of the creative economy. We need structured government intervention, and we need to build our own homegrown tech solutions. The global platforms are loyal to their own societies, so the constraints of navigating the perception of Nigeria on the global scale also affects how much access Nigerians have to technology services owned by foreign countries and foreign founders. We need to start looking at how we produce our own platforms. This is meant to be a national agenda, and you cannot remove the government from this.
Ige: What is the guiding philosophy of your entrepreneurial journey?
Ayoade: I’ve always believed that I only have two things in life: my brain, which is my capacity and the knowledge I’ve acquired; and my people, my mentors, my team, my tribe. Behind all of that is my family, which has stood strong behind me through the good times and the challenging times.
I believe I am uniquely positioned to be a catalyst to help people become the best versions of themselves. Most of the projects I’ve done are simply conduits for other people to become. My guiding principle is to help people become the best versions of themselves. That, and humour. I feel life is a lot, and we have to find a way to make the most of it.
Ige: In all of this, how do you unwind and relax?
Ayoade: It’s a bit of a paradox, but I like peace and quiet. I enjoy being alone to decompress, even though you will find me working in the loudest of places. When I’m not working, I want everywhere to be quiet so I can hear what my brain is saying.
I also play badminton, which is a very technical sport and a great way to network. I’m also the Vice Chairman 2 of the Oyo State Archery Association. I enjoy it and I also encourage people to give it a try. You’ll find me at my social club in the evenings, just gisting and planning the next event or project. I also love movies and games.
Ige: Any final thoughts?
Ayoade: In this age of AI revolution, every young person equipped with digital skills is a multiplier of economic opportunity. That’s what the Oyo State Digital Revolution is about. I have continued to keep the flag flying with “Vibe Coding with KJ Sheggs”. I also believe that my entire journey so far has been about building systems and structures that would better the lives of Oyo State, Nigeria while contributing to the global innovation landscape. When you build capacity, when you build people, you build communities. And when you build communities, you build nations. Ibadan is my home. I’m building here. And I believe others should too.
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