Introducing The Founder's Paradox

A tribute to the builders shaping tomorrow

Early in my career at a Big 5 audit and advisory firm (I'm showing my age), I was involved in managing a global Entrepreneur of the Year competition. I had the opportunity to meet South African business legends like Bill Lynch, Koos Bekker, and Brian Joffe. They won't remember me. I also interacted with the leadership team of the local chapter of the Entrepreneur's Organization, which we sponsored. I was immediately struck by how these individuals were different — more cutting-edge, more visionary, more energetic, less risk-averse, and more interesting.

I realized that big firms weren’t for me. I wanted to be part of something new — to make a real difference, see the results of my actions, and be held accountable. Through a series of well-timed events and strong connections, I found myself working alongside founders again and again — that rare breed of human who sees a gap, envisions what doesn’t exist yet, and then rolls up their sleeves to make it happen. It was far more intriguing, exciting, and rewarding than anything a corporate hierarchy could offer — though it was also much tougher in many ways.

Over the past 30 years, I’ve had the privilege of working with some of South Africa’s most inspiring founders, entrepreneurs, and owner-managers — people with the grit and determination to start, grow, and sustain their own businesses. I have done whatever was needed. I’ve learned how to lead sales and marketing teams to help stagnating businesses break through revenue plateaus, how to serve as a Marketing Director to build brand presence, and how to act as a trusted advisor to the CEO for navigating trust and delegation of decision-making. I’ve led programs designed to encode the culture that CEOs envisioned when the business was just them and a few employees — #1, 2, and 3, in the garage — and even tried to be Head of Product in my own startup. In my own opinion, I was least successful at this role. But my favorite? Head of Strategy, helping a very competent CEO prepare his business for its ultimate exit from a well-known Private Equity fund.

I’ve been in the trenches with these founders, caught up in that mix of vision, grit, and stubborn belief that turns wild ideas into real companies. Over time, I began to notice a familiar pattern: a moment that almost every successful founder reaches — not because they’ve lost their edge, but because the very strengths that got them this far start to work against them.

I call it The Founder’s Paradox.

That hands-on control, laser focus, and unstoppable drive — traits that fuel the startup journey — can eventually become the anchors that hold growth back. Suddenly, the business feels like it’s hit an invisible ceiling. Culture begins to dilute, urgency is lost, sales slow down, and everyone starts to wonder: does anyone care? It’s a tough, lonely spot, and I’ve seen even the best wrestle with it.

Of course, my observations are not unique. There are books written on Founders' Syndrome, the Inflection Point, and What Got You Here Won't Get You There — a topic that warrants its own blog post.

But what I have come to realize is that helping businesses scale is what I am truly passionate about. That’s why CtrlFuture was born — providing strategic, operational, and facilitation support for founders at this exact inflection point. My goal is simple: to help CEOs of small and medium-sized businesses shift from being the doer of everything to becoming the architect of a company that can grow beyond them.

To kick things off, I’m launching a new blog series, The Founder’s Paradox, exploring what this transition truly looks like — why it happens, how to recognize it, and how to navigate through it. Upcoming topics include:

• The Numbers Behind the Plateau — what the data shows about why growth slows and how to spot it early.
• The Psychology of Stagnation — the mindset traps and biases that make this phase so challenging (and so human).
• Practical Strategies to Break Through — evolving leadership, empowering teams, and building systems that allow the business to thrive without requiring your presence in every detail.

CtrlFuture isn’t about handing over a formula. It’s about partnership — working with founders who want their businesses to grow stronger, not just bigger.

Your vision built it.
Let’s make sure it can grow beyond you.