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Adii Pienaar

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

The Second Time Is Harder

I left WooThemes earlier this year to pursue a new startup. After 6 years working on WooThemes, I felt ready for a new challenge, I wanted to create something new and I really wanted to apply all of the knowledge and experience I'd accumulated over the years.

Thinking about that very quickly, you'd think that the second time has to be easier. It hasn't been though.

In fact - as much fun as it's been doing something new - it's mostly been fucking hard.


In the last couple of weeks, I've been trying to figure out why I've experienced this new (startup) journey as challenging as I have. Initially I figured that it was just a case of not being used to the requirements of an early-stage startup (a phase that WooThemes had long since passed), but it wasn't until I read this post that I realized that my experience was actually a thing.

On the surface, everything is going well:

  • We've got revenue;
  • We are building a loyal, engaged community; and
  • Growth has been ever so-slightly better than our churn.

Underneath the surface though, I'm an absolute wreck and inner turmoil has become a default reaction on a daily basis. I'm reminded of this Michael Caine quote:

"Be like a duck. Calm on the surface, but always paddling like the dickens underneath."

I know that these emotions are mostly irrational in the sense that they don't necessarily correlate with the facts (or what is actually happening). It is however impossible to ignore how one feels, so I wanted to delve into why exactly I'm finding this startup journey harder the second time:

1. I'm anxious about everything that could possibly go wrong.

They say that it is amazing that medical doctors still choose to have kids of their own, because they understand the science behind the multitude of things that could potentially go wrong during pregnancy and birth. That pretty much describes how I feel about startups.

I've made so many mistakes over the years and I thus know where many of the pitfalls are. This however means that I'm mostly walking around (still not knowing exactly what I'm doing / where I'm going), anxious about when I'll get my foot stuck in a hole and potentially break my ankle.

2. Risk mitigation mode doesn't make a good entrepreneur.

Coming off of a successful exit from WooThemes, I should be less risk averse based on my experience, my audience and ability to replicate that success. Yet, I've mostly become slightly more risk averse since I started working on something new, which has mostly been down to the fact that I have a young family (and I feel a responsibility not to disrupt their lives).

But being in risk mitigation mode makes for a really bad entrepreneur. This is one of my favourite quotes, but I've recently struggled to fully live up to this:

"A ship in the harbour is safe, but that is not what it is built for."

So in the last couple of weeks, I've had to spend a lot of time figuring out which part of every decision is about risk mitigation and which is actually good business sense, which has required additional (mental) overhead on top of everything else I've had to do.

3. I'm suffering from analysis paralysis.

I have too much data, too much feedback and too much past experience. Much of this could be mostly irrelevant to what I'm doing at the moment, but I'm struggling to categorize every data point as either irrelevant or valuable.

One of the biggest considerations in the last couple of weeks has been whether I should forge ahead in a bootstrapped / self-funded fashion or whether I should do a tiny, angel round to fund our 12-month roadmap. Not only did this challenge my own preference and status quo (I wanted to bootstrap this thing), but the more advice I seeked or information I perused, the more I found it hard to do the one thing that mostly helped me the first-time around: trusting my gut.

4. I'm impatient and after instant gratification.

It's funny how one of the reasons I left WooThemes is still prevalent today, which makes me wonder about the common denominator. :)

I'm incredibly impatient and I always want to run at full speed. This has been a big part of my drive to always work hard and push for more. If I can spend another hour doing something that would accelerate growth by even the tiniest percentage point, that's what I'd love to do.

With a new startup though, you're dealing with the muck of inefficient structures and invalidated learning. My #1 job has been to sift through all of that just to figure out where we're at, which hasn't been an instantly gratifying process. Even though I know that this is part of the job, it sucks not to have that adrenaline that accompanies running at full tilt.

5. My ego doesn't want me to fuck this up.

There - I said it.

You'll often find me encouraging you to "JFDI" and not to fear failure. And whilst I fully believe that; my ego doesn't necessarily allow me to eliminate those stumbling blocks that may prevent me from doing that.

I have a huge passion for helping entrepreneurs and that is the primary reason for me working on PublicBeta. My biggest fear about this though is that if I fail, my reputation (as an entrepreneur) will take a knock and that will make me less relevant: How am I supposed to help other entrepreneurs if I can't even help / succeed myself?

This line of thinking is completely unhelpful of course and is 100% noise. But it creates an element of self-doubt and conservatism, which has no place in startups.


By publishing this, I'm not looking for sympathy. Instead it is my hope that by writing about these irrational things, I'll evoke similar sharing by other entrepreneurs.

Everyone always writes about the tactical side of creating and running a startup. Heck, there is so much tactical advice out there, that the biggest challenge about that is deciding which advice to follow.

But no one considers these latent emotions that influences our decisions and our execution. They may be irrational and I might be conscious about them; but I don't necessarily have a blueprint for battling them.

The first step of addiction is to admit that you are an addict.

My recent articles about these emotions have been my first step to getting better.

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