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Starting a side business completely transformed my career. Here's how I went from blogging to helping tech startups grow.

Starting a side business

Starting a side business completely transformed my career. Here's how I went from blogging to helping tech startups grow.

Early benefits of a side business

Early benefits of a side business

I quickly discovered that blogging was a whole new world of challenges. There was a huge amount to learn. A lot of pitfalls, traps, and mistakes waiting to be made.

Despite this, I became hooked.

A side business provides the freedom to "be your own boss." Blaze your own trail. Challenge yourself as much, or as little, as you like.

It might not sound appealing to be constantly challenged. I'll admit there are days when you wish starting a business wasn't so challenging. The upside is a sense of achievement. This, for me, is one of the most under-valued aspects of modern work life.

Rising to the challenges of running a side business can lead to a sense of fulfillment that, ultimately, enriches your life.

Writing for business owners did something I didn't expect. It allowed me to talk directly to the decision makers — instead of programmers working on specific tasks assigned to them.

Decision makers, especially in small to medium size businesses, are a wonderful audience. They are hungry to grow their companies. They want to be efficient. They want to be competitive. They are "light on their feet" and can make decisions quickly without requiring board approval, committees, meetings, and so on.

A side business increases your chances of connecting with people and organizations with the power to have a significant positive effect on your life.

I began to generate revenue because the recommendations I made could be acted upon by the people with the power to do so.

A side income can provide protection from catastrophic loss of earnings – such as job loss.

Turns out, it wasn't long before the blog became my primary source of income.

Adapting the side business

Adapting the side business

The day before my final book was published, I found out that it had been already pirated and was freely available online. Sales were poor. Six months of work with very little to show for it.

The only silver lining was that some month's later a guy in Japan emailed me. He had pirated my book but found it so useful that he now wanted to pay for it. I was really touched.

I asked him to donate payment to a wildlife rehab and conservation charity, which he did. Arguably the best "book review" I ever received.

I stopped writing books and royalties began to dry up. This left me reliant on my blog. But not for long. Blogging quickly gave way to the very opportunities it helped create.

Business owners needing to solve complex technical problems began offering me jobs. At first, I was reluctant to go back to the 9-5 world of a day job because I was accustomed to the freedom of working from home (or anywhere with an Internet connection).

One day a tech startup put a completely new type of offer on the table. They were cash strapped. Their proposal was that I work with them for a few months helping to solve a technical problem and, in return, I would receive a low basic pay plus a small equity share.

I couldn't resist.

In the end, my 5% equity stake didn't amount to much because the startup didn't succeed. That's the risk of being involved in early-stage startups.

The experience did lead to a complete change in mindset about what my side business did. I wasn't a blogger after all. I was a type of venture capitalist specializing in early stage tech startups. Only I didn't invest money, I invested time and intellectual capital.

Instead of sitting quietly at my desk writing blog posts I was working with dynamic new startups, undertaking complex and challenging jobs, meeting diverse people and making new connections. Blogging as a side hustle was only a stepping stone — a marketing platform — to the real business of being a skills-based tech VC.

Where a side business can take you

Where a side business can take you

To date, I've invested in eight (and counting) businesses. In that time I have developed weird new heuristic algorithms to tackle mind-bendingly complex NP-Hard problems associated with route optimizations. These deliver significant cost savings in the transport and logistics industries.

Software I have designed and built for a variety of tech startups is used on a daily basis by companies in over 60 countries around the world.

That's not something I could have imagined when I first started blogging. It's something I had the opportunity to do because starting a side business put me in front of the right people in the right niche.

Ultimately, evolving my side business into what I do today was as much about challenging myself as it was about the potential to make good money.

I couldn't imagine doing it any other way.

It's not always easy. It's almost never easy. Yet it's often worth it – succeed or fail. Hopefully starting your own side business brings you the same opportunities and fulfillment it brought me.


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