A Less Riskier Path to Entrepreneurship in Software Development

You gotta be willing to crash and burn. If you're afraid of failing you won't get very far.

Steve Jobs

I'll admit I'm terrified of failing. I am no Steve Jobs.

How do you start a business when you can't (or are unwilling to) be exposed to the risk?

"Can't" doesn't sell widgets or pay the rent. You may want to be a daredevil entrepreneur but it doesn't mean you should leap at any chance to crash and burn.

Clip your downside, protect yourself from extreme harm...

Nassim Nicholas Taleb, Author of Antifragile

Mr. Taleb suggests a way to deal with high risk in his book Antifragile. It's called the Barbell Strategy. It's a way to take on high risks ventures without the risk of financial ruin. The idea is that you keep 90% of your wealth in very secure investments and invest the other 10% in highly speculative but possibly extremely rewarding investments.

It's possible to use the Barbell Strategy to start your business. I used it, although unwittingly, to overcome my fear of starting a software company.

I've invested a majority of my time in learning software development, my safe investment, while dabbling in 'side projects' until I'd built up enough funds and experience to protect myself from financial ruin.


I've been able to slowly increase the amount of risk I can take on because of the skills I've developed. The more experience I gained the more employable I became and the less risky venturing out on my own became.

At Wufoo I did my startup residency. At SurveyMonkey (SM) I learned to measure everything Silicon Valley style. At the Department of Veterans Affairs (VA) I learned, well that I didn't like the VA.

One of my side projects eventually became my business.

Every programming language I learned, every project I completed, every customer I spoke to made me a bit wiser. Starting a software company became a little bit less risky.

8 years.

That's how many years I worked before I thought I was ready. On the day I completed my 2 year contract at Survey Monkey I was off.

I cheated though. I started the company before I left. 5 Months before leaving we launched CodePen PRO. I mentioned I was terrified of failure?

Being afraid is okay. Fear drives action.

How do you start a company when you're terrified of failing? The answer is you don't. You work and learn until you're not afraid anymore. I wasn't ready when I left college 8 years ago.

A new company is really a burning building. If you put out the fire you get to keep the building. What I got out of 8 years of experience is a fire suit and a hose with lot more pressure.