In the early days of a startup, a tremendous amount of effort is put into getting product shipped and selling the vision. It’s very difficult to achieve the former without doing the latter. Great leadership is required in order to sell the vision. The ability to recruit and motivate the right people to make things happen is invaluable.

It’s accepted practise that the visionary founder assumes the role of CEO. I see the role of CEO as two parts. Firstly to set direction, define culture, motivate and inspire, recruit, and reinforce the vision. Secondly to manage the business of the business – essentially the operations of the business.

When I was a 35 year old CEO, I knew everything. Now I’m a 58 year old CEO and there’s rafts of things I don’t know.
- Howard Diamond

If you have attended an event where entrepreneurs are bound to be lurking, you will undoubtedly notice they are the most optimistic people ever. It’s their job to be right? They have to exude confidence in what they are doing because they are always selling, even when they aren’t.

However what you probably might not know and rarely see are the moments when the most confident and even the most successful entrepreneurs doubt themselves. The reason you don’t see it often is because they are masters at hiding it. In fact, I doubt myself quite often but you wouldn’t notice it because I never show it. I’ll explain in moment how I deal with doubt and uncertainty.

At the moment I am biding my time and trying to find the right idea to pursue. I have been able to sort my ideas into two categories. The first being stupid ideas you see on Techcrunch and wonder how they raised funding at all. While the second are near impossible industry disrupting ideas that make meaning.

What I have realised is that Aduity was much like a first girlfriend, you know – your “first love”. However, once you have parted ways, you realise that you never really knew what love was but you now have a slightly more mature understanding. I think somewhere along the line the long term vision of Aduity was lost and therefore it ultimately never made any meaning (nor was it going to based on the new direction).

I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.
- Michael Jordan

It was mid 2008 and Younique was doing reasonably well. However, I had an itch that I needed to scratch. I wanted to build a mobile advertising platform – think DoubleClick meets AdMob. At the time the mobile advertising market wasn’t as competitive as it is today. Towards the end of 2008, I decided to forgo the R3m+ revenue Younique was likely to generate for 2009, shut it all down and found what would today be known as Aduity.

Unfortunately things haven’t turned out as planned. I’m not going to go through exactly what went wrong, it’s still a little too early. However, as the founder, I have to take responsibility for the failure irrespective of what went wrong. I am publishing this because I want to force myself to become more comfortable with failure and to also encourage other tech entrepreneurs to share their failure(s).

I think TrustFabric has to be the most ambitious and most important tech startup to ever come out of South Africa. I’m not going to lie, I am in love with the idea. However, the challenge it faces is huge and I believe its over night success will be measured in years.

TrustFabric aims to solve the sweet spot of CRM and VRM, but from the consumer side. Essentially, you keep your personal data up-to-date in one place and TrustFabric allows organisations you have a relationship with to sync that data. Additionally, you can limit what information organisations have access to and TrustFabric will also verify organisations to ensure they are legitimate.