Making New Mistakes

by Adii Pienaar

Now working on @InPublicBeta. Founder @WooThemes. New Dad. Ex-Rockstar.

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Family-First Startups

A couple of months ago, I started working on my new startup and I set myself a bit of a “soft” goal: I wanted to try create a startup that generates $1m in annual revenue and I wanted to work only 5 or 6 hours a day.

The motivation for that goal was to seek greater work+life balance. In my past, working 80+ hours was the norm for me and I really become addicted to being connected to any of my devices (Macbook, iPhone or iPad). The fact that I had founded an “always-on” startup obviously didn’t help with that.

All of this reached a tipping point for me 12 months ago. And I committed (to myself and my family) that I wouldn’t relapse to those old, bad habits again.

But a couple of months into my new startup journey and I already feel immense pressure (and temptation) to go back to my old ways.


We all know startups are hard and it mostly runs on fear. And I know that it is that fear

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On Parenthood & Making Mistakes

I originally wrote this on 1 July 2013 whilst travelling back home from Bangkok. I typed the whole article in Notes.app on my iPhone during the flight and after I had, had a couple of glasses of good red wine.

But I never published this when I got back to my computer, because it felt way too emo to me.

I stumbled back onto this yesterday and whilst reading it I felt vulnerable, both as an adult and especially as a parent. That vulnerability is what changed my decision to publish this: when something feels uncomfortable, it’s a good reason to do it. :)


I’ve been away from my son for 10 days.

Every time I look at this picture of him, I’m reminded not just about the bond that I hope we share (one day, when he is older & understands the nuances of life); but also the dreams I harbour for his future.

See, my son is awesome, because he is my own and of my blood. I can see that he has

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Pay The Man

There’s only one way to ensure products you use stick around: keep the founding entrepreneur(s) interested.

The same applies to the products we - as entrepreneurs and software makers - build: the only way that you can maintain & nurture those products is for you to have that vested interest.


I was recently embroiled in a shitstorm with WooThemes, when we increased the prices of our products and limited grandfathering for past purchases. Our goal:

  1. Fix our broken business and support model, which was chomping away at our operating margins.

  2. Ensure sustainability so we could be around for years to come (i.e. pivot from the broken legacy model).

  3. Hopefully free up enough of our operating margins to experiment and innovate (a long-term risk if we’re not doing this often enough).

While the situation played itself out eventually, there are a few things that still bother me; not about

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“You Have The World At Your Feet”

I was sharing breakfast (literally) with my son this morning whilst drafting an e-mail which should have a major influence on our family’s (and ultimately, my son’s) future.

At one point during that e-mail, Adii Jr was being cute and I turned to him to say: “Do you know that you have the world at your feet?”

Whilst he obviously has no idea what I’m working on or what that even means, I felt a sense of pride being able to tell my son that. I guess most (all?) parents have the ambition to create a better life for their kids than the life they had themselves. It’s about progression.


As I said those words though, I also realised that I’m not exempt of that sentiment. I also have the world at my feet.

Yes, my son is almost 2 years old, which means I’m 26 years ahead of him already. Seen in a certain light, I’ve “lost” 26 years to make the world my bitch.

But from a “glass-half-full”

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What I learnt writing 30 000 words about branding

I decided to write a book about branding in the first week of June. Today - two months later - I’m releasing the compilation of the 30 000-odd words that eventually made it into the final version.

This post is about taking stock, reflecting on the process and sharing some of the things I’ve learnt (about myself, branding, writing and other people) during this 2-month journey.

(If you are expecting a neatly polished and structured article, which categorizes these thoughts into a manicured and categorized list, you’ll be disappointed. Instead consider this a brain-dump on the topic.)


 Not much is impossible.

Writing a book - just like most other things in life - isn’t that hard if you really put your mind to it.

A friend once told me that self-discipline isn’t actually that hard. Instead it’s about the underlying motivation to do something; if you’re really motivated to do

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Self Discipline & Motivation

I’ve previously written about the various things I do to cope with the challenges of being an entrepreneur. For this week’s Startup Edition, I want to dive a little deeper into how finding a good work+life balance has helped me with that.


Balance is whatever works for you at any given time. There’s no silver bullet. Balance can rarely be defined numerically with 50/50 or 80/20 ratios.

Using the mantra that happiness is success, I posit that balance is the feeling that my life is in sync.


What I’ve realized over the last couple of months is that finding balance between my work and the rest of my life requires a certain amount of planning, having a daily routine and self-discipline.

But self-discipline is incredibly hard to stick to in itself. The key I’ve found is the underlying motivation. So it basically comes down to being motivated enough to actually do something, which in

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Who Are You?

The first step you should take in your new startup is to figure out who you are.

(This post is part of this week’s Startup Edition, which poses the question “What advice would you give young entrepreneurs?”.)

As you head out on this journey, you’ll notice that there’s one common denominator in all of your successes, failures, challenges and celebrations: you.

You are the founding entrepreneur. You had the idea and you had the guts to take on the risks attached to running a startup. You also had the vision and the belief that you can conquer the world against all odds.

Looking at those words (and the prevalence of “you”), it seemingly becomes a no-brainer for your first startup steps to be getting to know yourself.


“No one is free who has not obtained the empire of himself. No man is free who cannot command himself.” - Pythagoras

As an entrepreneur, you are the life force of your

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That Little Bit Extra

Everyone always talks about going that extra mile. But could you possibly just do 1% more? And what would the effect of that be?

I love running and I’ve developed quite a cool habit: At the very end of my run, I reach the entrance to our estate / gated community. Instead of taking the shortest & most obvious route to our house, I instead take the longest loop around. That little bit adds another 0.5km to my run.

0.5km is obviously not significant on it’s own, but consider these:

  • If I add that to a 5km run, I’ve just run 10% more than I would have; and
  • If I’m running 40km a week and adding 10% more in total, that’s a total of 4km that I’ve run more than I would’ve otherwise.

My point being that the little bit extra (all the 0.5km’s) add up pretty quickly. And I bet that it actually has an exponential effect on my fitness and running ability.


The question I’d like to pose you, is

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What Running Has Taught Me About Entrepreneurship

Last month I ran a total of 120km’s which included, running my personal best on an unexpected half marathon. This obviously meant putting in the time and I subsequently spent a lot of time on the road: just me, some music, the sound of my (sometimes ragged) breathing and most importantly: my thoughts.

During these runs, I think about many different things and I try avoid thinking about work or business at all. I also try use this time to just shut off from the world and do some introspection.

One of the recurring themes to pop into my head in the last month, was drawing the similarities between how I was progressing as a runner and how I could potentially apply the same mindset to being an entrepreneur and / or running my company.

The thing is that running isn’t something that comes naturally to me (unlike being an entrepreneur for example) and as such I’ve had to try a variety of

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Believing in the Invisible

In my past I had a religious friend that explained to me his religious beliefs are based on the mantra that you need to believe in the things that you can’t see. This is very much how I feel about business today.

Regardless of my own religious or spiritual beliefs, I know that one needs to believe in things that are intangible and are likely difficult to prove. You’re required to believe in concepts and theories.

This also reminds me of Steve Jobs’ Stanford Commencement speech in 2005, where he spoke about connecting the dots:

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads

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