My love-hate relationship with entrepreneurship

October 12, 2015
6 min read

Entrepreneurship is the poster-child of the economy – consensus appears to be that running your own business is the ultimate pinnacle of a career – full of fun and the secret to untold riches. That might be the truth for a very few entrepreneurs, but there’s also a dark, lonely and extremely challenging side to it.

So what’s my current mission? I co-founded an influencer marketing business and am commercialising a novel heart valve replacement. Two businesses in two totally different fields, so the question I’m always asked, is how are they related? Conventional wisdom says that your career and your skill-set needs to specialise over time, which I agree with. I’m specialising in running efficient technology businesses that are differentiated by their intellectual property, ability to scale, and importantly, by the people working on them. So that’s my answer to those that are in fact interested. Through these businesses, as well as previous forays into a tutoring marketplace application and a digital content business, I’ve come to learn more about my love-hate relationship with my career choice.

My love for entrepreneurship

Being different

Without a prior understanding of an industry, you tend to ask fundamental questions about it and challenge the way things are done in their current form.  Less than two years ago, I asked Kirsty Sharman “What is media?” with reference to paid media behind digital content. At Webfluential, we now are arguably running the fastest growing media business in Africa because we took a different approach to solving a market need. Looking at a business from first principles allows you really consider the value proposition of the competitors and allows you to see that most businesses have a “me-too” approach to operating.


lego-man-murrayAs a kid, a new box of Lego wasn’t just an opportunity to stick to the construction guide given. I’d always turn to the back page with the other variations of what the pieces could be used to assemble. Imagination and experimentation. Two things that your own business affords you that often need more haggling to get right in a corporate. If what you’re selling or doing isn’t mainstream, you have to try and learn with your own skills and money. In reality this translates into 99% perspiration, but it’s still very enlightening!

Learning to work with people

Having a vision for a business or product has to be articulated through a lot of communication and charisma to the team. I’ve come to learn that most people don’t realise their own potential, so it’s often a stretch target to achieve what you’re wanting, but because you’re their boss and they don’t want to admit that they’ve failed at an objective – I find that it’s a pretty rewarding dynamic. Check out the benefits of outdoor advertising on billboards, especially underground ones, by visiting

My hate for entrepreneurship


A few weeks ago I went to a breakfast alumni event with ex colleagues from my stint in investment banking. The conversation points to the ultimate unspoken, competitive question – “is the risk you took leaving a high paying career paying off more handsomely than our decision to stay in banking?” As an entrepreneur, you can’t say that you’re down, not winning, losing the fight, or one step away from packing it in. Your team, your staff, and your support structure all need you to be positive and declare that you’re winning. Most of the time, you’re not, and it’s lonely because you can’t share that fact with too many people. Thank goodness for my wife!

experiments-entrepreneurshipThe peanut gallery

There are a lot of bullshit quasi-entrepreneurs out there. Swaths of people spending their lives being entrepreneur incubators, coaches, even studying post graduate degrees on how to be great entrepreneurs. Start-up events, due diligence conferences, advisory firms and talks given by people that have never run their own business and been so successful that they’re qualified to actually talk, advise or guide on the subject. They’re quick to pass comment on the state of entrepreneurship, who’s good and who’s not. Their insecurity about their own value offering in the industry is confirmed to me every day that goes by without one of them calling to say they’d like to meet up and discuss funding or advising me.

Frictional cost of operating

The frustration and time wasted on frictional issues in a small business will one day soon become so important to entrepreneurs that they will seriously consider the country they wish to found in before considering incorporating. Crime (our staff’s laptops being stolen out of their cars), taxes (I’ve not received a single benefit for creating more than 30 full time and countless part time jobs from the SA government), and very average service delivery from the industries that supply to us, all slow us down. I miss the cotton wool cocoon of corporate, where you didn’t really have to ever phone the ISP yourself, fix the magnetic lock on the office door at 1 o’clock at night or worry about who checked the VAT return.

With these things that I love and hate being daily experiences in my career as an entrepreneur, I have to think so carefully about where I choose to spend my time and effort in creating value. Every minute is an opportunity cost. Thus, my mandate for business ventures I’ll consider working on:

  • Doing things that are breathtakingly new and ambitious
  • Work with other founders who radically want to change an industry, or better, the world
  • Have an audacious vision of a business seeking enormous markets

The challenge is that if you apply these constraints to a nebulous business concept, very few people really understand what you’re actually trying to do. They don’t understand the risks because of all the unknowables. Most of the time, you’re not always in full understanding of what you’re doing, either, adding to the confusion. And then you want people to join your crusade, or risk their money on you…? We’ll chat about that another time.

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