Why Entrepreneurial Success Often Requires Great Timing

In 2012, I started a leisure business and realised I couldn’t afford any of the mobile Point of Sale (POS) systems on the market, so I asked my friend Paul Walton to build me one in the form of an iPad app. The system soon got noticed by other traders who wanted one for themselves and suddenly we had a new business on our hands, Intelligent Point of Sale (IPOS). We grew the business for 4 years before it was acquired by iZettle in 2016, which itself was acquired by PayPal in 2018 for $2.2 billion dollars.

Having successfully exited IPOS, Paul and I launched a new business, Boundary, targeting disruption in the home security market. Yet, when I look back on my entrepreneurial journey to date and the road ahead with our latest business, I realise that what we commonly think of as entrepreneurial “success” is often a question of good timing. Here’s why…

Knowing when to go for it is key to entrepreneurial success.
Sometimes an entrepreneur picks a business idea and sometimes a business idea picks an entrepreneur. My idea was to run a paintball business, not a Software-as-a-Service platform, but the opportunity with IPOS soon overtook things. We researched the marketplace and realised that there wasn’t much competition out there for our product.

We started work on it at the end of 2012 and by July 2013 we had launched our product and taken our first paying customers. We built a website and did some basic SEO to get it ranking. We posted on some forums pointing back to our website and built up a list of about 100 contacts. Some of those became our beta testers and some were onboard as customers for our launch date. We saw our opportunity and moved on it as quickly as we could.

Likewise, with our new business, the plan was to take more time off, but an idea came to me while I was on holiday that I couldn’t shake. I had a disappointing customer experience after having a new security system installed at my home, then I saw some new ways to market security systems while in the States and that set me thinking.

I told Paul about the idea and he was keen to do something with it. I wasn’t sure initially about launching a new business again so soon, but knew we had a window of opportunity to disrupt the market that would only stay open so long. I then got excited about the prospect of building our own electronics product for the consumer market and solving the problems that I had experienced myself, so we went for it.

Knowing when to delegate.
I consider myself to be a natural delegator. I find it easy to recognise where my time and talent is best spent for the benefit of a business, but I know that my business partner Paul found that difficult at the times. For a long time, you understand, Paul was the only software engineer in the business and he had built the platform from the ground up – it was his baby. Learning to entrust things to other software developers with particular specialisms took a while but he soon learned to love building a team of talent around him and having others there to help him achieve more than he thought possible.

That said, I’ve found that people are the biggest challenge in any business and it’s very difficult to be right all the time. I’ve made some brilliant hires at times of people who, on the face of it, weren’t fully qualified for a position but had a real hunger to succeed. I’ve made some other hires that looked great on paper but just didn’t work out. That’s why hiring by committee can be a mistake. After a while, though, you learn to trust your instincts.

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