Entrepreneurial success: 5 lessons from the trenches

Daniel Levy, co-founder and co-CEO of Flow

Having walked this path myself, I know the road to success is rocky and rarely straightforward. But I’ve found it's this unpredictability that best hones the skills and fuels ambition. Here are five learnings that have shaped my experience and continue to drive my leadership.

1. Blind luck might open a door, but it’s grit that turns luck into success

   Luck, they say, favours the prepared mind. In my experience, luck is just the spark – grit is the fuel that keeps the fire burning. Back in 2007, when my business partners and I built and founded Popimedia, we were fortunate to identify a gap in the local advertising market at the right time. But it wasn't just luck, it was our insistent pushing of boundaries, even when the odds were stacked against us.

   Truth is, South Africa simply doesn’t have the venture capital and angel investor scene you’d find in Silicon Valley, for example. So most homegrown entrepreneurs can’t just ride on a good idea and hope to sell it – they have to create a viable, well-performing business model. That often means identifying a big problem that needs solving, long hours, hard work, and funding it all yourself. True entrepreneurship is about the long game, and hoping for a lucky break that leads to sustained success.

2. Don’t believe your own bull: Stay critical, stay innovative

   One of the most dangerous traps for an entrepreneur is falling into the echo chamber of their own success. I’ve seen many promising ventures falter because the leaders started to believe their own hype, losing sight of the critical need for constant questioning and innovation. I’ve surrounded myself with equally inspirational and hard-working partners who aren’t afraid to call out my blind spots.

   This culture of rigorous self-examination keeps us agile and honest, and lets us pivot quickly when necessary. The moment you start believing you’ve figured it all out is the moment your business starts to stagnate. The market is ever-evolving, so comb over your business – refine every process, scrutinise every success.

3. Stick to the knitting: Find your advantage and scale it

   One of the most valuable lessons I learned is to focus on what you do best – what I call 'sticking to the knitting'. I believe that finding your niche and scaling it is key to building a sustainable business. In a world full of distractions, staying focused on your core strengths is what will set you apart from the competition.

4. Persistence beats resistance: Get comfortable with being uncomfortable

   Entrepreneurship is not for the faint-hearted. It’s marked by constant challenges and resistance, both internal and external. But in the face of setbacks, you have to learn to back yourself and your vision, even when it means stepping into uncomfortable territory. The ability to persevere through discomfort is what separates those who succeed from those who merely dream.

5. Make scary decisions: The line between failure and great success

   The final lesson is perhaps the most challenging: making scary decisions. These are the decisions that can either get you fired or lead to unprecedented success. These are moments when you have to trust your gut and hope your parachute opens on the way down. I’ve had my share throughout my career – from choosing to enter new markets and invest in cutting-edge technology to pivoting our business model. Such decisions are fraught with risk, but as an entrepreneur, you must face making them, because they are the decisions with the potential to catapult your business from good to great.

The fact is, the entrepreneurial mindset is not something you’re born with – it’s something you resonate with and cultivate through experience taking risks, resilience, and drive. Push yourself to innovate, disrupt, and ultimately, to connect people and businesses in ways that matter.

I keep learning how success is a series of calculated risks, persistent efforts, and the courage to make choices others might shy away from. That, to me, is the thrill of entrepreneurship.