Some entrepreneurial journeys begin with a big idea. Toba Subair’s began with a mindset: believing in the process, recognising opportunities and turning them into possibilities, rather than waiting for the perfect time. It is a mindset that has allowed him to try different things, learn along the way and gradually figure out where he could make an impact.
That mindset has followed him through different stages of his life and career. His first experiences with work came early, as he took on teaching roles in a secondary school before exploring other opportunities. While studying Computer Science in higher institution, he also worked as a graphics designer for different companies. Rather than seeing these experiences as separate paths, he embraced each one for what it had to teach him.
That willingness to learn and make use of what was available eventually led him to co-found a tutoring company shortly after graduation. From there, he gained experience in sales and management, gradually developing a deeper understanding of people, business and what it takes to turn an idea into something sustainable.
Over time, those experiences began to come together in entrepreneurship.
Today, Toba is the Founder of Tripperzway Travels and Tours and Co-founder of iTech Homes and Properties, with businesses spanning travel and real estate. His journey reflects an approach he continues to hold onto: you do not always need to have everything figured out before you begin. Sometimes, the opportunities along the way become the very things that prepare you for what comes next.
At the centre of it all is a desire to understand people, recognise genuine problems and build businesses that create meaningful and lasting value.
In this Spotlight Interview with CA, Toba reflects on his unconventional path into entrepreneurship, the lessons behind building Tripperzway, expanding into real estate, staying close to his customers and the impact he hopes his journey will have on the next generation of African entrepreneurs.
CA: Your journey began long before you formally became an entrepreneur. Which of those early experiences shaped you most?
Toba: While studying Computer Science, I was also a school teacher in a senior secondary school and working as a graphics designer. I was already balancing academics with work and different ways of creating value.
When I graduated in 2018, my friend and I founded a tutoring company that connected students with tutors physically and virtually. That was my first real opportunity to build a business around solving a problem we had identified.
From there, my career took me through sales and management. Looking back, what shaped me most was my willingness to keep trying different things. In many ways, I had been experimenting with entrepreneurship long before I formally called myself an entrepreneur.
CA: What eventually gave you the confidence to leave an established business environment and build something of your own?
Toba: I don’t think it was one particular moment. It was a combination of experiences that gradually made me realise I could build something myself.
Working within an established business taught me how businesses operate, how to work with people, how to sell, manage responsibilities and what it takes to keep a business running.
Eventually, I wanted to apply those experiences to something I could build. The confidence did not come before the decision. The decision itself created more confidence. I took the step, accepted that there would be things I did not know and committed myself to figuring them out.
CA: Tripperzway has served more than a thousand clients. What has that journey taught you about customer experience?
Toba: One of the biggest things I’ve learned is that people don’t just remember the service you provide. They remember how you made them feel.
Travel is very personal, and every client has different expectations, budgets and reasons for travelling. At Tripperzway, we try to understand those individual needs instead of approaching every client the same way.
Building lasting relationships also comes down to trust. For me, customer experience is simply about listening, understanding and delivering on what you promise.
CA: You have since expanded into real estate as Co-founder of iTech Homes and Properties. What has building across different sectors taught you?
Toba: Real estate directly impacts people’s lives, whether they are finding a home, investing in property or looking for the right opportunity.
Building across travel and real estate has taught me that although the industries are different, the fundamentals of entrepreneurship remain the same. You need to understand people, identify real needs, build trust and be willing to adapt.
It has also taught me not to limit myself to one industry. Entrepreneurship is about recognising opportunities and having the courage to explore them.
CA: How do innovation and sustainable growth influence the businesses you build?
Toba: Innovation is about finding better and smarter ways to solve problems and serve people. It doesn’t always mean creating something completely new. Sometimes it is simply improving what already exists.
Sustainable growth means building businesses that can stand the test of time instead of chasing quick results. I try to make decisions with the long term in mind, whether they involve our customers, our team or how the business operates.
I want to build businesses that are successful today but strong enough to keep creating value tomorrow.
CA: How has your background in sales influenced the way you make business decisions today?
Toba: Sales taught me very early that you cannot build a successful business without understanding the people you serve. Customers are often the best source of information about what is working, what needs to change and where opportunities exist.
I try to listen to what customers are saying, pay attention to their experiences and use that feedback when making decisions.
Staying close to the customer keeps the business grounded. It ensures we are solving problems people actually have.
CA: What did being recognised as one of the 100 Most Influential Young Africans in 2024 mean to you?
Toba: It was a very meaningful moment. It was encouraging to know that the work I had been putting in was being noticed and that my journey could have an impact beyond my immediate environment.
I also see recognition like that as a responsibility. Influence gives you a platform, but what you do with that platform matters more.
For me, the real value of the recognition is not the title. It is the responsibility to make the influence count.
CA: Looking across your journey, what impact do you ultimately hope to have on the next generation of African entrepreneurs?
Toba: I want my journey to show that there is no single path to becoming a successful entrepreneur.
My hope is to inspire young Africans to start with what they have, remain open to learning and have the courage to build.
Ultimately, I want my work to create opportunities, contribute to the growth of others and leave something meaningful for the next generation.
