That Don Guy
Tuesday, 21 June 2011

About two years ago, I told my boss that we needed to talk. He wasn’t a stupid man by any stretch of the imagination, so he knew something had been under my skin for a few weeks.

I don’t think he was expecting me to tell him that I was leaving my cushy, well-paid job with fantastic benefits, in order to start a software company with a close friend.

After I had finished training up my replacement and celebrated my last day, it hit me: I was unemployed, and partially responsible for the livelihood of another human being (my business partner).

In all honesty, I was scared shitless.

I had, provided that I didn’t go all-out on Porsches and cocaine, enough cash to last me for a year.

I had never founded a company. I didn’t know the difference between a corporation and an LLC, much less how to actually set one up.

I had never sold a damn thing in my life. The one time I tried, selling magazines to raise money for my school, I couldn’t even close a single order.

I had zero clue what marketing was. So I had no idea how to even get the message out to the potential customers to whom I had no idea how to sell.

In short, I had a year of runway, and couldn’t even start building my airplane until I figured out how to mine and refine aluminium.

I had never done anything even remotely as risky.

And, you know what? I crashed and burned.

But not before releasing a product.

Sure, it took my business partner and I a lot longer than we had planned. Neither of us had before taken, on our own, a product from ‘idea’ to ‘something customers can actually complain about’.

We had gone out, found people brave enough to risk our private beta, and convinced that we weren’t a complete gaggle of clowns. And while the product was rough as hell, our initial customer feedback was very positive. We were clearly moving in the right direction.

Unfortunately, we hit the end of our collective financial runway, and while Linode, our hosting company, is shockingly awesome, they don’t accept hopes and unicorns as a form of legal tender.

When it became clear that it was time to find a Real Job again, things were very, very different.

In a year, I had learned a mountain about sales, marketing, and business. I had built up a solid network while hunting around for customers and partnerships. I had gained the sort of experience that can only come from eating, breathing, and dreaming code for a solid year.

Two weeks later, I started as the CTO at a different startup, with my business partner stepping in as the tech lead.

It’s another story, but let’s just say this time, huge success.

If I had never quit my stable job, I’d still be there today. Because I took the first real risk in my adult life, my career has rocketed forward farther than I ever thought possible.

More importantly, I’ve had two amazing years. I’ve ridden in a Hummer through the middle of Tokyo, survived the fourth-largest earthquake in recorded history, and drank an Australian under the table.

Taking risks is scary. Stepping outside your comfort zone is hard… but that’s where the magic happens.