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Adii Pienaar

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

Go With Fear

I'm allowing fear to guide my decision-making.<...>

In the last year, I allowed fear to to influence and (sometimes) dictate my decisions across all spheres of my life. I was vulnerable, trying to recover and fear didn't make my journey any easier. A quick glance at my blog and writing in the last 12 monts will give you a clue of the extent to which fear trickled through in so many of my thoughts.

As such, it's not been a surprise to me to realize how that also influenced me with the recent announcement and launch of my new company. Even though I feel vastly different to the individual and entrepreneur I was a year ago, there's still been a bit of scar tissue that has contributed to the way I do things and the decisions I've made.


Ever since I had the idea to build Receiptful, I've been contemplating exactly what our strategy and execution should look like. I've had various discussions with friends, founders and entrepreneurs that have augmented my own thoughts in this regard and the result was a pretty broad spectrum of possible approaches.

When it came to launch day, I had decided to go with a hybrid approach using a bit of what I know (experience), a bit of what I'd learnt (best practice) and a bit of where I wanted to go (vision & intuition).

This felt safe.

It wasn't the same as before, but it still resembled a personal comfort zone.

And I could rationalize the approach pretty easily.

But my head and heart never felt completely aligned with this decision; not to the extent that I was willing to risk everything in pursuing this.

So I've changed this.


Today we've announced that Receiptful is now free for all customers. Shock. Gasp. Horror.

This will come as a surprise to anyone that's spent 5 minutes reading about me and my past as a staunch supporter and fanboy of bootstrapping / making money / not doing all of the trendy things that happens in Silicon Valley.

If you've connected the dots already, you'll understand why this is (seemingly) such a drastic shift for me:

  • I'm not making our customers pay (today at least) and there's no money coming.
  • If that's the case, where is the money coming from? Oh, it means that Receiptful will have to be funded in that anti-bootstrapping way.
  • Receiptful now is all about pursuing the vanity metric of sending more receipts. How will that work out?

I know; I'm being such a hypocrite.


But where'd this change come from?

For starters, I realized that I had very specific fears that had been holding me back from making this decision before:

  • I feared the backlash and reputational impact that this would have, since this new approach contradicts at least parts of the things I had said and proclaimed about business and entrepreneurship before.
  • My only experience in building a successful business before was to do it in a bootstrapped and organic way. Copying my own blueprint feels safe and any alternative brings fear and anxiety; mostly of the unknown, but also not being sure that I can execute on that.
  • What were my friends gonna say? I had surrounded myself with like-minded friends (fellow founders & entrepreneurs) who had all been drinking the same Kool-Aid about how to build a business. Would I be able to back up my decision to counter their scrutiny?

This has mostly just been limiting and has prohibited me to experiment, explore and dream. There's no right way to build a business and there's definitely multiple ways of skinning a cat.

I also realized that what I wanted more than "success in business" is the opportunity to challenge myself, really swing for the fences and leave a legacy. This quote from a recent Groove article crystalized it for me:

"First-time founders care most about their exit. Every time after that, you focus on legacy."

Exiting from WooThemes meant that I had achieved financial security for my family. The caveat to that is that we would still have to be smart about the way we use / invest our money and that we'd need to generate (new) income for the foreseaable future (from a job or new businesses).

This however means that measuring the success of Receiptful in absolute dollar terms is - at best - only part of how I'd try to quantify the value and reward of this endeavour. The ability to experiment, learn and be challenged ranks at least as high as any dollar amount. Truly leaving a legacy would be a bonus reward for reaching the very top.


Saying this out loud draws an internal sigh of relief, but at the same time it provokes so much fear.

Today - and for the foreseeable future - I'm going along with that fear though. And I'm letting it guide all of my decisions; not in the way that it before, but where my decisions will embrace it.

I know that going with that fear will lead me down paths where I am challenged and where I will be learning. I will also have the opportunity to figure out how to use those challenges and learning to build a successful business.

This is not a 180-degree turn, but it is a fork in my road.

The reality is more a case of this being a journey of learning, where I'm learning about life, business and myself.

In that sense, I can never be the same Adii today than the Adii I was yesterday.

I've always pushed myself very hard. I wear my heart on my sleeve, I'm (mostly) an open book and I don't mind admitting when I've fucked up.

My life is about making new mistakes and using them to evolve.

And now I've added fear as just another tool on my toolbelt.

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