By Matt Trenchard - posted on May 14, 2016

What I Learnt from our First Three Years of Entrepreneurship

Read on to see:

  • What it took to make the entrepreneurial “jump”.
  • How a lack of knowledge can be helpful and a stumbling start is better than no start
  • The difference between being freelance and being an entrepreneur
  • What taught us that less is more
  • Our struggles shifting from being a group of capable individuals to being an inter-dependent team.
  • Why we hung on to our dreams
  • How we got past self-centred arrogance and learned to ask what people really wanted
  • What I mean by, “turning the company inside out."

It’s easy to write a story in retrospect and write it as if it was all planned from the beginning. That’s not how we experience real life. We experience real life in the moment sometime in the hope of a dream or vision that we have before us. Sometimes that vision is clear. Often it isn’t and only gets clearer as we go. It’s in the looking back that we join up the dots and set that each part of the journey was required to get us to the place that we now have got to. I writing this not with the sense of having arrived and without the solid feeling of having crossed the line, of having stuck the flag into the ground saying, “It’s finished.” Instead, I write this with a profound sense of being on the path, of walking the yellow brick road towards the Emerald City.

North Point Leadership (NPL) was official registered as a legal company in October 2012. It, or something like it, had been in my heart for a number of years. I asked myself what and how much would I need to feel happy to make the jump into self-employment. Like a lot of wannapreneurs, I felt I needed more capital (enough to register a company and service for 3 months), greater qualifications, more experience and a bigger network.

Back then I thought I had all I needed. They say early success can be a hazard. (I connected with Sarah Anthony at this time and so now I shift from saying ”I” to “we”). We each had a number of clients for whom we were coaching and/or facilitating, we were building a leadership development programme and life seemed good. Good until a year later, when I felt like I’d exchanged one boss for six, we’d not sold even one leadership development programme and we had clients who either were late paying us, or didn’t pay us. Something had to shift.


At the end of 2013 we realized that we needed to shift from working for others to getting work for ourselves. However wanting things to change and actually changing are two different things - even for professional coaches who are supposed to know this.

By the end of 2014 earlier ideas had begun to crystallise. We saw the need for coach training programme with a realist worldview (one in which reality is objective and immaterial objects - e.g. thoughts - exist). We also saw the space in the market. So we began. Looking back, had we known the size of the challenge we’d set ourselves we might not have jumped in with such gusto. Parallel to this, we began gaining traction coaching entrepreneurs. We found the combination of our own experiences together with our coaching skills gave us a unique offering.


In 2015 we took some of our own medicine and took on a business coach/mentor of our own. He helped us get over the hurdles holding us back including learning how to build a team around us and to see things from the customers' perspective. I had to learn to let go of trying to “make it all work” and trust a) the others would do a better job than me even when I wasn’t there and b) that we could earn sufficient revenue to cover their costs. The reality was that as much as we were freed to do that which we were best at, so we then had more earning capacity.

Learning to see things from the customers’ perspective turned the company inside out. We saw that up until that point we’d been self-centred and all about our ideas, our products, what we were doing. We were a coaching and training company that worked with entrepreneurs. The shift that came lead us to see that we needed to be a company serving entrepreneurs which, amongst other offerings, included coaching and training. The question now was what else could we bring?

With the scene now set and the preparations done, the stage is set for 2016. It’s our intention to launch and run two Coaching Certification and two Entrepreneurship programmes this year, to coach 30 entrepreneurs, to launch a podcast and increasingly learn how we can bring value to the growing entrepreneur community in Dubai.

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Strength on the journey,

Matt Trenchard

Co-Founder of North Point Academy