From The Editor
When I started out as an entrepreneur, I used to say, "Don't give me advice, just give me money." That's all I thought I needed. Until I got the money and blew it. Belatedly, I realised it always starts with knowledge, and the learning never stops.
There are moments in life when you don’t need money, titles, or even opportunity. You just need guidance.
A few words from someone who’s walked the path you’re on, stumbled where you’re struggling, and still found their way through.
That’s why we started Ask A Mentor!
Every week, we will reach out to people who inspire you: visionary leaders, thought leaders, celebrated builders and fearless dreamers. And ask them the questions you wish you could ask yourself.
Mentorship shouldn’t be reserved for the privileged few with access.
For our first edition, we reached out to Cheslyn Jacobs, soon-to-be CEO of TymeBank.
As you read this, I hope that Cheslyn’s words ignite something in you.
Welcome to Ask A Mentor.
Tawanda Forgive Dube
Founder and Editor
Mentor Of The Week
Get to Know Cheslyn Jacobs
We have been wired to salivate over rags-to-riches stories. In our dopamine-fueled frenzy for such stories of glitz and glamour, we unfortunately overlook the quiet and humble, yet far more impactful and significant stories that possess every quality imaginable to build and inspire the world.
One such story that stands to inspire a generation is that of Cheslyn Jacobs.
From the streets of Cape Town to the helm of a billion-dollar fintech, Cheslyn's story is a journey of a transformational leader who steadily climbed to the top while leaving footholds for others.
Some leaders don't announce themselves with fanfare, but prove themselves in the people they elevate, the systems they build, and the doors they open for those who thought it was impossible.
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Cheslyn joined Tyme in 2012, long before it became the powerhouse it is today: over 11 million customers, record lending growth, and a spot on TIME's list of the 100 Most Influential Companies in the world.
“The biggest job of a leader, is to provide a platform for people to be the best versions of themselves.”
Jacob lives by the African philosophy “Umuntu ngumuntu ngabantu.” A person is a person through other people. His leadership is rooted in the quiet conviction that progress happens when people are empowered, not controlled.
When Someone Believes in You First
When asked about the people who shaped his journey, Cheslyn doesn’t hesitate to credit Coenraad Jonker, the founder and CEO of Tyme Group.
“Some turning points don’t come with a title,” he reflects. “Some arrive quietly, like a person who sees something in you before the world does.”
That belief, he says, became the catalyst that redefined his trajectory, from a 22-year-old eager to prove himself to a transformative leader in one of Africa’s fastest-growing financial institutions.
“Coen led by example,” he recalls, “not because he always had the answers, but because he asked the right questions.”
A Life Built on Effort and Persistence
Cheslyn’s early life mirrored that of many South Africans: scarce resources, limited opportunities, but an abundance of determination.
“I didn’t have a perfect start to life, but it did teach me the perfect lesson: success comes from showing up and giving your best, no matter what.”
He worked full-time while attending night classes to earn his degree. His wife, Janine, was his anchor, reminding him that his dreams were valid, his grind meaningful, and his legacy still to be written.
Today, that same discipline guides his life as a father and leader.
A Bank That Believes in People
TymeBank’s astronomical rise was anchored on accessibility, inclusion, and innovation for the underserved. The digital-first bank also champions simplicity, transparency and affordability.
In a country where millions were once excluded from the financial system, TymeBank changed the narrative.
From kiosks in major retail stores to instant digital accounts, it became the people’s bank, democratizing access and restoring trust in what banking could mean.
In 2024, Tyme Group hit unicorn status, valued at $1.5 billion after a $250 million funding round led by Nubank. There are over 1,400 unicorns globally, and only eight have been recorded in Africa.
But even amid global recognition, Cheslyn insists on staying grounded.
In Conversation
3 Questions with Cheslyn Jacobs
Last week, when I reached out to Cheslyn, I was met with more humility than I had ever encountered from someone leading a billion-dollar brand.
When most people come into positions of power and influence, they become unapproachable. How do you stay humble and accessible while running one of Africa’s most innovative banks?
I am a firm believer in staying true to who you are. Ultimately, that is what got me to where I am, I have an unwavering belief that it’s the same thing that keeps me moving forward.
You’ve been with Tyme since its inception. How do you stay in the room when others chase greener pastures?
The reality of this in my view is that the most important thing in your life is your WHY. All of us should spend the time crystallizing what that why is. Once that is clear, it’s so easy to make the right decision as you will make them with the belief that it gets you closer to your WHY. Why we do what we do is so important to me, so for me there is no other place. It’s all about meaningful work for me.
You’ve helped shape one of South Africa’s most innovative banks. What separates leaders who create impact from those who simply manage systems?
I think there is a close link to the answer above. I have a saying, ‘you can do good by doing good’. We all have a role to play in moving our ‘communities’ forward, and ultimately, how much you give back to society in the work you do will be the thing that creates lasting impact. Important to note is that I am not talking about charity, it’s all about enterprise.
Key Takeaways
Key Takeaways
Stay True to Yourself. Who you are is what got you here; don’t lose that on the climb up.
Know Your WHY/Purpose is your compass. When you’re clear on why you do what you do, every decision becomes easier and every challenge more meaningful.
Do Good by Doing Good. Real impact isn’t charity, it’s enterprise that uplifts others. Lead in ways that make your community stronger.
Show Up, Every Day. Success isn’t born from perfect starts, but from consistent effort. Discipline beats circumstance.
Lift as You Rise. Leadership isn’t about titles. It’s about creating space for others to thrive.
Whether you’re building a business, scaling a team, or shifting a habit, putting your goals into the world changes the way you chase them. When you tell the world what you’re aiming for, it stops being a wish and starts being a plan.
Now everyone is watching and waiting.
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