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Adii Pienaar

Now working on Receiptful. Co-Founder & ex-CEO of WooThemes. Author of Brandiing. New Dad. Ex-Rockstar.

Being Your First Investor

(This essay is part of a collaborative blogging experiment to answer the question, 'Who took a chance on you?'.)

I'm sitting here, staring at a blank computer screen (Draft's awesome, minimalist writing UI doesn't make this feel less loney), trying to answer the question "Who took a chance on me?".

Thinking back about the journey I've had, I can identify quite a few people who took a chance by following me or my vision:

  • Every single one of those initial customers who paid me with real money in the early days. I had no reputation back then and I would not have been surprised if they had their doubts about me. But they bought the product that I had developed and became the impetus for this thing that is WooThemes today.

  • My co-founders when they quit what they were doing to work on WooThemes full-time. At the time, working on Woo was definitely the less cozy, less secure and less stable option. But they opted against those comforts to join my vision ("vision" may not be accurate though).

  • Our first two employees. Whilst we had been going for almost a year when they joined, the verdict was still out on whether this would be a project with a lifespan of a couple of years. Or a career move that would form part of their CV & career paths.

I can go on and on adding to this list.

On this journey, I've met so many different people that have influenced and helped us on their way. Most of the time, I didn't acknowledge their contribution initially. But without these people that took a chance on me, WooThemes would not be what it is today.


In thinking about all of this, there's one person that took a chance here that had the greatest impact: myself.

That sounds pompous, arrogant, narcissistic, egotistical, etc. of course. But it's the truth.

See, when this was all just an idea in my head - a notion that there could be an opportunity here - I was the only person in the position to take a chance on me and this venture.

When I started to build the very first product, I was the only investor and the only believer.

If I could've separated myself into the "Adii, the entrepreneur" and "Adii, the investor", the investor part of me had no reason to trust the entrepreneur. I had no track record of success, no real experience and thus no real reason that I could succeed at this.

But something within myself (part naiveté, part delusion) clicked and I never considered any of this.

I just took a chance and backed myself to succeed.

If I wasn't willing to take that chance on myself, how could I have ever convinced others to follow me and take a similar chance?


Hindsight is an exact science.

But years later, I can remark that the "high risk, high reward" mantra of backing an early-stage entrepreneur has paid off well. :)

What are you doing to invest in yourself? And are you taking a chance on yourself?

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