Crafting Success Through Grit, Curiosity, and Seizing Opportunities

Crafting Success Through Grit, Curiosity, and Seizing Opportunities

Ndabenhle Ngulube, one of the three original co-founders of Pineapple Insurance, the InsurTech turning the insurance industry on its head, kicked off the re-launch of Seed Academy’s entrepreneur events with an at-capacity audience consisting of Seed Academy Alumni, Clients and Partners.

Blending inspiration with practical advice, Ndabenhle captivated the audience as he shared the core principles that shaped his path and provided ‘behind-the-scenes’ insight into the strategies and actions that have led to Pineapple’s incredible success in a few short years.

Below is a recap from the evening that served as a reminder that entrepreneurship often emerges from the most unexpected paths…

Ndabenhle Ngulube’s Three Pillars of Success

  1. Grit: The Backbone of Perseverance – From Zimbabwe to South Africa to Germany and back to South Africa, Ndabenhle’s formative years saw him contend with both the challenges of living in a new country and adjusting to a different educational system. It was during this time that the essence of grit was ingrained in him. Faced with a six-month academic deficit and with dropping a grade not being an option, Ndabenhle found himself attending school by day and extra lessons at night to catch up – he jokingly said “at 15 years old I was already working a double shift in terms of hours” but importantly he was taught the early lessons of hard work and resilience, crucial for his future entrepreneurial venture.
  2. Curiosity: The Fuel of Innovation – Curiosity may have killed the cat, but it also turned a would-be accountant into a tech innovator. Ndabenhle’s conversations with his university roommate who was studying information systems sparked an interest in coding. Curious to know more about the subject, he borrowed his roommate’s textbook and quickly found himself deep-diving into coding, spending all his free time (he was still pursuing his accounting degree) in the comp lab or internet café practicing what he learned – “If you ever find something that you’re passionate about, you should always throw yourself into it.” he told the audience. This casual conversation ignited a passion that not only re-shaped his career path but laid the foundation for Pineapple.
  3. Opportunity: The Art of Taking Your Shot – “Apply for every single opportunity that comes your way,” was a key message and central theme in Ndabenhle’s story. Throughout his journey, from attending a coding bootcamp to entering a startup competition that laid the groundwork for Pineapple, Ndabenhle seized opportunities that many would overlook, regardless of the outcome. His approach is a reminder that success is often determined by our willingness to take risks and step into the unknown. “No matter what opportunities come across your path just apply for them… shoot your shot… the worst that can happen is a ‘no’ but the upside of potential is literally limitless,” Ndabenhle concluded.

The Launch and Success of Pineapple

In ‘shooting his shot’, Ndabenhle entered a competition run by German reinsurer, Hanover Reinsurance, who were looking for individuals with little or no exposure to the insurance industry that they could put together in teams to compete and develop fresh ideas that would disrupt the insurance landscape in South Africa. Ndabenhle’s entry was successful and he was placed in a team with Mannes van Heerden and Matthew Smith – the guys ‘didn’t know each other from a bar of soap’ but were given this mammoth task of spending the next 6 months finding ways to disrupt the short-term insurance space… and so the first pages of the Pineapple story were written.

Ndabenhle shared with the audience the key strategies, approaches and tactics that paved the way for their success. These included:

  • Start with the Problem: The trio’s approach to meeting the competition brief was centered on understanding the customer’s pain points. Traditional insurance models often leave customers feeling disconnected and doubtful, a gap they aimed to bridge. By utilizing technology to enhance transparency and accessibility, Pineapple transformed the insurance process, making it more intuitive and user-friendly. Customers could now insure individual items through a streamlined mobile app. This not only simplified the insurance process but also empowered customers by giving them control over what to insure and when and allowed customers to ‘try’ Pineapple with relatively low-risk items, ultimately building trust in the brand.
  • Make an Entrance: The strategic launch of Pineapple with the distribution of actual pineapples with an informative flyer at traffic intersections is a brilliant example of unconventional marketing. The effectiveness of this strategy was evident in the immediate uptick in app downloads and brand mentions on social media – demonstrating the impact of creative marketing and the importance of making a memorable entrance into the market.
  • Embrace Traditional Marketing: Despite initial successes with digital marketing, the team quickly realized that to truly build brand awareness and credibility, they needed to embrace more traditional forms of marketing. They expanded their strategy to include billboard advertising, a move that proved to be highly effective. Pineapple’s core ideology of looking at what everyone else is doing and then doing it differently was carried through to the marketing efforts. Their self-deprecating and humorous billboards challenged the conventional and often bland insurance advertising. This refreshing approach significantly boosted traffic to their website and increased sales – Pineapple saw a 350 to 400 percent increase in sales over the year the campaign ran. Pineapple’s approach demonstrates the importance of an integrated marketing strategy.
  • Adapt to Market Needs: As Pineapple grew, the team needed to do a strategic pivot—from a purely app-based model to a more inclusive web presence – in response to customer preferences for quicker, more accessible service options that did not require app downloads. For the founders of Pineapple, it wasn’t just about building a product; it was about adapting to how customers preferred to interact with it. – as Ndabenhle said, “You should never fall in love with the solution, you should fall in love with the problem”.


What sets certain entrepreneurs apart is not just what they do when faced with opportunities, but how they create opportunities for themselves. Ndabenhle and Pineapple’s journeys encourage us to persevere, stay curious, and embrace every opportunity with open arms.