You're reading the blog of

Adii Pienaar

Family man, seeker and learner. Revealing my inner-poet. 2X Founder: Conversio (acquired by Campaign Monitor) + WooCommerce (acquired by Automattic). Ex-Rockstar.


In a game of cowboys and crooks, nobody started out validating the very obvious threat.<...>

I have been trying to systemize the process of entrepreneurship. I have been seeking that magical 1-2-3 step formula that I can successfully replicate from one venture to the next, in a way that would avoid risk and failure as much as possible.

Heck, I've taken this approach to the extreme.

In hindsight, the only thing I'm proud about in that whole process is that it was so extreme and with that came a significant risk.

My mindset has been one focused on frugality: go slowly, validate all assumptions, mitigate all risks, spend as little money or time as possible, and - heaven forbid - never charge full-speed into a possible failure.

The worst part of this is that none of these things have ever been part of my own definition of entrepreneurship.

If you asked me do define an entrepreneur or entrepreneurship prior to the last year, I'd always have one, super-clear answer: An entrepreneur is someone that sees an opportunity or gap and is willing to take the risk in exploiting that opportunity or gap.

Not all of this other bullshit that I've doing recently.

The irony in all of this is that every one of those things (going slowly, conserving resources, risk avoidance and never moving far enough into the unknown) all brought their own risk: the risk of not really doing.

I've been reading Hatching Twitter and there's one bit (from Ev Williams' blog) that jumped out at me:

"...from excitement and bold moves, great things often happen."

This reminds me of Dan Martell's mantra (and the story behind it) of the world rewarding courageous decisions.

An entrepreneur is someone that sees an opportunity or gap and is willing to take the risk in exploiting that opportunity or gap.

There is a part of this that I trace back to my own perception of what it would've been like being a cowboy: brave, having a disregard of risk, being the main man about town, having a bravado and having the fastest (gun) draw in town.

I also have this perception about the Wild, Wild West, where there were very few rules and only the fittest ever survived.

That's entrepreneurship in my mind.

There's a brashness and a disregard of one's own safety that is required to start a new business.

It's about having the ability to spot an opportunity and then pursuing that opportunity regardless of the risks and costs associated with it.

That's why entrepreneurship remains hard. And it should be, because it's never been destined for the fainthearted. I don't say that to be exclusive (I actually hope that more people would be entrepreneurs), but ultimately it requires a certain level of craziness to be an entrepreneur.

I have a friend that always tells me entrepreneurs float between the states of semi-delusion and being clever. That's the only way they'd get stuck in the trenches and actually believe that one day they'll climb out of it with a reward of some kind.

There is no way to avoid risk as an entrepreneur; whatever way you go, you'll be taking on risk. Entrepreneurs have however developed a knack of taking on risk in the most intelligent way possible.

In thinking about risk, take the route that sees you progressing as fast as possible. Even when that means you're running ever faster towards that brick wall.

Hopefully you'll back yourself to dodge that brick wall (at high speeds) before hurting yourself.

I know I'm backing myself to do just that.

Join 5,000+ subscribers who get my weekly email, with thoughts on life, identify, making things and more.