I’m ultra-competitive and I absolutely despise losing. At anything. It doesn’t mind whether I’m working on my business or playing a game of Scrabble. I always play to win.

And that’s a good thing.

In Grade 6 & 7 I had a teacher that always told us: “Show me a good loser and I’ll show you someone that loses often.”

That thought has stuck with me ever since and when I think about it now, I realize that I’ve applied that opinion in a very specific way in my life.

I’m not a bad loser in that I’ll throw my toys and be a complete twat when I lose; in fact, I can be (somewhat) graceful in defeat and I can (eventually) accept it. But that doesn’t mean I have to actually like losing.

If I look at my entrepreneurial journey in the last 5-odd years, I can remember multiple challenges I faced which I only got through, because I absolutely despised the possibility that I might fail / lose...

Sometimes staying true to yourself is the most difficult thing to do. The irony is that this is also sometimes the biggest compliment you can pay yourself.

I was at a wedding of good friends this past weekend. I had only known the bride & groom for a little over a year (my wife and the bride became friends at varsity and reconnected a couple of years later), so I wouldn’t pretend to know everything about either of them.

I had an interesting experience though, as I heard so many guests say something similar to “That’s so her!” in referring to the bridal gown, the complimentary jacket the bride decided to wear, the decor and pretty much everything else.

Initially my reaction was to realize that I obviously didn’t know the bride this well. But then I realized that the bride’s long-standing friends were paying her the ultimate compliment; they were congratulating her on executing a...

Last night, just before going to bed, I was trying to dispose of a fly that was blissfully (to him) and frustratingly (to me) buzzing around my bedside lamp. As I was attempting this disposal, I noticed that there were at least three dead flies suspended within the bedside lamp’s bulb.

Judging from where the fly was flying, it was obvious that his friends simply flew too close to the bulb and they eventually succumbed to a nasty death.

The reality of this and the fact that this current fly wasn’t amending his flight patterns brought back memories of the story about Icarus.

In Greek mythology, Icarus tried to escape from Crete where he lived. Icarus’ father subsequently constructed wings, made of feathers and wax, for him to fly away. His father however warned him: don’t fly too close to the Sun.

Icarus however ignored the advice, causing his wings to melt due to the Sun’s heat...

(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...

(This essay is part of a collaborative blogging experiment to answer the question, ‘What’s the greatest startup hack you’ve seen?’)

We’ve made many decisions at WooThemes that have had a major impact on our business, but this is the one I’d call the greatest startup hack ever: we gave our customers EXACTLY what they wanted. Even though, ironically, it didn’t really solve any kind of problem.

In the middle of 2012, we found ourselves really struggling to cope with the sheer amount of support requests that we were receiving from customers. At the time, we were using a custom forum-based system that only “acted” like a support ticket helpdesk (all conversations were public to the whole community, but only the original ticket requester & Woo staff could interact on a thread).

So we made the decision to focus on internal improvements to address this need:

• We hired a bigger support...

Ever since the rumours about the Yahoo-Tumblr acquisition running over the weekend (which it turns out weren’t just rumours), I’ve wanted to communicate my opinion on the matter. Until this morning, that opinion would’ve included gems like these:

• “Hahahaha! ROFL! WTF! OMFG! LOL!”
• “Tumblr has raised hundreds of millions of dollars in funding, has very little revenue. So why would Yahoo be paying that kind of earnings multiple for a business? Seems desperate…”
• “This is another bad example for startups. Acquisitions like these send out the wrong signal that it is okay to raise millions in funding, but never really worry about revenue.”

And so forth. You get the point…

But I never published any of that.

See, I realized that ultimately my opinion didn’t really matter, but more importantly, that this deal was down (mostly) to two individual entrepreneurs (along with their respective...

The other day I was having a Clarity call with an entrepreneur about generating initial traction for his startup idea. The entrepreneur wanted me to share some of the strategies that we had implemented (with success) at WooThemes over the years. But he had a proviso:

“I know quite a bit about many inbound and outbound marketing strategies and activities, but most of them only work when you already have visitors on your website. I would for example love to use a messaging schedule to increase my conversions, but how do I go about getting those initial visitors on my website?”

He had a point here. Starting up is hard and all of the interwebs has become congested. It definitely is difficult to get noticed.

My suggestion to the entrepreneur was to use some form of cold-calling. His product lent itself to target specific individuals on LinkedIn with an “I’ve built this thing and think you...

(This essay is part of a collaborative blogging experiment to answer the question, ‘how do you invest in yourself?’)

Literally.

In the last year or two, I’ve learnt that the safest and best investment that I can make is the investment I make in myself; not by putting money into the bank or by backing a new startup during their angel round.

This investment into myself also hasn’t necessarily been financial, but has instead taking a much more holistic approach to ensure that I’m best-equipped to deliver an appropriate ROI.

I believe that as an individual - and specifically as an entrepreneur - I’ll always be in beta. I’m not perfect (never will be) and the only way I can stay ahead is to keep learning & improving every single day.

I love how this post describes that process as building “soft assets”, which will some day materialize in actual, hard assets (of some kind).

In that...

This past weekend I completed my fourth half marathon, but my first in over 2 years.

I went into the race with 4 weeks training, having missed out on training from mid-January to mid-March due to injury. So I was probably under-prepared. :) But that also meant that I was running without any pressure; I didn’t train hard or long enough to have a concrete goal or expectation of myself. I just wanted to finish the race without being completely dead.

I started the race feeling good, but soon found myself being pulled into running a much quicker pace than I wanted to run (due to everyone else’s adrenaline and excitement). At times I was literally running more than a minute / kilometre quicker than the pace I had trained at and I knew that I had not trained enough to keep that up over 21km’s. There was no way I could finish the race this way.

During the race, I started thinking about my...

A couple of weeks ago I read Ben Huh’s post about how he got really depressed and contemplated suicide. One thing really stuck with me:

“Failure is an option, and a real risk. Failure and risk something entrepreneurs understand well, and learn to manage. However, death isn’t an option, it’s an inevitability. **And before I die, I want to take as many swings at the fence as I can.”

Swinging for the fences.

I’m only 28 years old. I haven’t had a near-death experience. I’m relatively healthy and my life expectancy is good.

I’ve also had a good - maybe even great - life thus far. I’m married to my beautiful wife, who doubles as my soulmate, best friend & muse. I have a 16-month old son that is starting to look & act more like I do every day. I had the opportunity to take a chance (on myself) when I was quite young and that chance has lead to immense success at WooThemes (which has in...