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Lessons Learnt

Stuart Weaving’s Unexpected Journey To Becoming A Serial Entrepreneur

Serial entrepreneur Stuart Weaving has seen tremendous success across a very diverse range of industries. He attributes his success to having a nose for opportunities, developing good business acumen and being a terrible student.

GG van Rooyen



Stuart Weaving

Vital Stats

  • Player: Stuart Weaving
  • Claim to fame: Stuart Weaving is a British serial entrepreneur with close ties to South Africa. He founded the Weaving International Friendship Foundation in 1968, which embraces the Friends of the Springbok and Friends of the Lion, and helps reunite families and friends in the UK, South Africa, Australia, New Zealand and North America. Over 48 years, the foundation has assisted with more than one million family reunions. SA has benefitted greatly with an injection, in today’s terms, of over R30 billion.

I was a terrible student, at the bottom of a class of 40 pupils

At 11, my parents realised that I couldn’t see, and got me a pair of glasses. Once I had glasses, I moved up two spots to number 38. Glasses or no glasses, I just wasn’t a good student. I left school at 14 and started doing other things.

I was an actor, I had a stint in the navy, and I started some small businesses. Starting as an entrepreneur at 14, I amassed experience before I had even left my teens. People who only leave school at 24 start their journey so much later. They do develop important skills, but the point is this: Being a bad student doesn’t mean that you won’t succeed. Many successful entrepreneurs were bad students.

Related: Manie Spoelstra On Why Negotiation Is The Genesis Of Entrepreneurship

I’ve never been a big reader

Aspiring entrepreneurs are often told to read, and you can certainly gain from a lot of knowledge through books, but I often viewed my dislike of reading as an advantage. While others were reading, I was coming up with business ideas, crafting business plans and turning thoughts into action.

There is nothing wrong with reading, but it’s important not to spend so much time accumulating information that you never actually follow your dream.

The key to success lies in spotting an opportunity and turning it into a viable business.

There are loads of business ideas out there

All you need to do is find a problem that must be solved. I’ve been involved in different industries because I spotted opportunities.

You can always find excuses why you shouldn’t pursue a business idea. As an entrepreneur, you should trust your gut. You’re a consumer yourself. You know what you like and dislike as a consumer.

You know what a good customer experience looks like. Don’t overcomplicate things, just find the best way to solve your customers’ problems. That said, I don’t think you could be a success if you care only about money. You have to really want to solve a problem. 

Diversification is key

I’ve always looked at ways to expand and diversify. A great way to grow your business is to identify associated opportunities. Never allow a lack of experience to hold you back. For example, I once owned a company that organised events.

When the catering wasn’t good enough, I decided to bring that function in-house. I had no background in catering, but I knew what customers wanted: Good food and short queues.

Related: The 8 Lessons Entrepreneurs Could Learn From Farmers

Good teams come in pairs

Although I was a bad student, I discovered later in life that I had a great head for numbers. Figures came to me very naturally. But I wasn’t good when it came to marketing.

I’ve found that a company works best when you have two people at the head of it: One who is great with numbers, and the other with marketing and communications. So, I’ve tried to ensure that all my companies are led by a team like this.

You need to be honest and acknowledge your shortcomings. Know what you’re bad at and find someone who can bring those skills to the table.

Long-term success lies in knowing when to amputate

Industries change and opportunities come and go. If you want to enjoy long-term success, know when to let go. An entrepreneur needs to be brave and tenacious, but not cling to a dying idea.

Be open and realistic. Admit when it’s time to move on, whether that means pivoting the business, closing a department or selling the company. Don’t be so married to a business that you go down with it.

Related: For Shatty Mashego Success Lies In Maintaining A Positive Mindset

Take note

The key to success is to trust your gut and have the courage to explore ideas. 

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Lessons Learnt

7 Cannabis Industry Millionaires Making It Big In The Marijuana Business

These entrepreneurs have capitalised on a new market set to continue to grow rapidly as more countries legalise marijuana across the world.

Catherine Bristow



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1. Brendan Kennedy


Brendan Kennedy worked on job sites as a carpenter to pay his way through university, with his eyes set firmly on becoming an architect, until the allure of Silicon Valley changed the course of his direction. While working at technology start-ups Kennedy began thinking about the possibilities that medical marijuana provided.

“I was really sceptical of medical cannabis,” he says. “It took a year of having conversations with patients and physicians and hearing the same story, repackaged but essentially the same, over and over and over again, where my scepticism eroded and I became a believer.”

In 2013, Kennedy and his partners applied for a licence from Health Canada and launched Lafitte Ventures, which was later renamed Tilray. Today, the company is a global leader in medical cannabis research, cultivation, processing and distribution.

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Lessons Learnt

Scaleup Learnings From Our Top Clients – What The Most Successful Entrepreneurs Do Right

So, how do our successful clients move through these constraints to scaling up? We see four key drivers of success, and they are: people, strategy, flawless execution and finance.

Louw Barnardt




You’re out of your start-up boots, staff is increasing, your client base is growing, revenue is up and you’ve proven your case to the market. Now it’s time to scale up. The challenges of this vital growth phase are different and it’s a time that demands different mindsets and different actions. In a world littered with small business failures, it helps to be well-prepared for scaling up using a proven methodology. At Outsourced CFO, we get an inside look at the success factors of our clients who are mastering the transition.

On the one hand, scaling up is a really exciting phase; this is what moves you into real job creation and making an impactful contribution to economic growth. On the other hand, it is really hard to scale up successfully. We see three major constraints that limit companies’ transition from start-up to scale-up:


The business has to have the leadership that can take it to the next level. When you start scaling up, especially rapidly, the founders can no longer do everything themselves. The team must grow and include new leadership talent that can take charge and execute so that the founders are working on the business instead of in the business.


The processes, procedures, networks, systems and workflows of the business all need to be scalable. This is imperative when it comes to your infrastructure for the financial management of your business. You’re only ready for growth when your infrastructure can seamlessly keep pace.

Market access

Scaling up demands more innovative marketing and storytelling so that you can more easily connect and engage with the new employees, clients, network partners, investors and mentors that need to come along with you on your scale-up journey.

Businesses that build a market conversation and a compelling brand narrative during their start-up phase are better positioned to have this kind of market access when they need to scale up.


It is critical to have the right people on your team. Our successful entrepreneurs have what it takes to attract, inspire and retain top talent. A strong team of smart, ambitious and purpose-driven people who love the company and want to see it succeed contribute greatly to a world class company culture. They are adept at communicating a compelling vision and establishing core values that people can take on. These entrepreneurs are tuned into the aspirations of their people and focus on developing leaders in their teams who can in turn develop more leaders.


It is planning that ensures that the right things are happening at the right times. At successful scale-ups strategies and action plans are devised to ensure that the most important thing always remains the most important thing.

Strategy includes input from all team members and setting of good priorities for the short, medium and long term. Goals are clear and everyone always knows what they are working towards. The needle is continuously moved because 90-day action plans are implemented each quarter to achieve targets and goals that are over and above people doing their daily jobs.

Flawless execution

Top entrepreneurs are not just focused on what operations need to achieve, but how the business operates. They have the right procedures, processes and tools in place so that everyone can deliver along the line on the company’s brand promise. Frequent, quick successive meetings ensure the rapid flow of effective communication. Problems are solved without drama. There is no chaos in the office environment. Everyone is empowered to execute flawlessly to an array of consistently happy clients.


Everyone knows that growth burns cash. A rapidly scaling business faces the challenge of needing a scalable financial infrastructure to keep the company healthy. Our successful entrepreneurs pay close attention to finance as the heartbeat of the business, ensuring that everything else functions. They look at the tech they are using for financial management and for the ways that their financial systems can be automated so that they can be brought rapidly to scale. The capital to grow is another vital finance issue.

The best way to finance a business is through paying clients on the shortest possible cash flow cycle. However, when you are scaling up and making heavier investments in the resources you need for growth, it is likely that you will need a workable plan for raising capital. Our scale-up clients know the value of accessing innovative financial management that provides high level services to drive their business growth.

Navigating the scale-up journey of a growing private company is one of the hardest but most rewarding of careers to pursue. Having people in your corner who have been through this journey before helps take a lot of pain out of the process. No growth journey looks the same, but there are tried and tested methods that will – if applied diligently – lead to definite success. Happy scaling!

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Lessons Learnt

That Time Jeff Bezos Was The Stupidest Person In The Room

Everyone can benefit from simple advice, no matter who they are.

Gene Marks




When you think of Jeff Bezos, a lot of things probably come to your mind.

You likely think of, a company he founded more than twenty years ago, that’s completely disrupted retail and online commerce as we know it. You probably also think of his entrepreneurial genius. Or the immense wealth that he’s built for himself and others. You may also think of drones, Alexa and same-day delivery. Bezos is a visionary, an entrepreneur, a cutthroat competitor and a game changer. He’s unquestionably a very, very smart man. But sometimes, he can be…well…stupid, too.

Like that time back in 1995.

That was when Amazon was just a startup operating from a 2,000 square foot basement in Seattle. During that period, Bezos and most of the handful of employees working for him had other day jobs. They gathered in the office after hours to print and pack up the orders that their fast-growing bookselling site was receiving each day from around the world. It was tough, grueling work.

The company at the time, according to a speech Bezos gave, had no real organisation or distribution. Worse yet, the process of filling orders was physically demanding.

“We were packing on our hands and knees on a hard concrete floor,” Bezos recalled. “I said to the person next to me ‘this packing is killing me! My back hurts, it’s killing my knees’ and the person said ‘yeah, I know what you mean.'”

Related: Jeff Bezos: 9 Remarkable Choices That Shaped The Richest Man In The World

Bezos, our hero, the entrepreneurial genius, the CEO of a now 600,000-employee company that’s worth around a trillion dollars and one of the richest men in the world today then came up with what he thought was a brilliant idea. “You know what we need,” he said to the employee as they packed boxes together. “What we need is…kneepads!”

The employee (Nicholas Lovejoy, who worked at Amazon for three years before founding his own philanthropic organisation financed by the millions he made from the company’s stock) looked at Bezos like he was — in Bezos’ words — the “stupidest guy in the room.”

“What we need, Jeff,” Lovejoy said, “are a few packing tables.” Duh.

So the next day Bezos – after acknowledging Lovejoy’s brilliance – bought a few inexpensive packing tables. The result? An almost immediate doubling in productivity. In his speech, Bezos said that the story is just one of many examples how Amazon built its customer-centered service culture from the company’s very early days. Perhaps that’s true. Then again, it could mean something else.

It could mean that sometimes, just sometimes, those successful, smart, wealthy and powerful people may not be as brilliant as you may think. Nor do they always have the right answers. Sometimes, just sometimes, they may actually be the stupidest guy in the room. So keep that in mind the next time you’re doing business with an intimidating customer, supplier or partner who appears to know it all. You might be the one with the brilliant idea.

This article was originally posted here on

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