You Should Be Scared to Quit!


I work on 20Skaters, ThreeFortyNine, Ontario Startup Train and a few others. My vanity site is

I gave a short talk last year at GWMM titled “How To Quit Your Crappy Job“. It was a tongue in cheek way of pitching Startupify.Me. In the talk I discussed Josh Kaufman’s definition of a successful business:

  1. Creates or provides something of value that…(Product Development)
  2. Other people want or need. (Marketing)
  3. At a price they’re willing to pay, in a way that…(Sales)
  4. Satisfies the purchaser’s needs and expectations and…(Value Delivery)
  5. Provides the business sufficient revenue to make it worthwhile for the owners to continue operation. (Finance/Operations)

bossMost jobs allow you to be involved in one, maybe two of the above. Going it alone requires you to deliver and balance all of them. That is a massive leap!

The typical response I get when I pitch Startupify.Me to someone gainfully employed is “I’m scared to sh!$ of quitting my job”. You should be scared and chances are you should keep your job. There are, however, a tiny fraction of potential entrepreneurs currently locked away in decent jobs at great companies. Certainly for us here in Canada, it’s the path set out for us. Get your degree, get the best job you can and work your way up the ladder. Rarely were we offered any path beyond that one.

For those of you in that tiny fraction, fear is good. The goal isn’t to eliminate fear, it’s to leverage it for action. I played high school football with a guy who, before every game just after warm-up, would walk off on his own into the endzone and throw up. He was always one of our best players. People would always want to help him or ask him “are you alright?” but his teammates knew to leave him alone, let him puke, he’ll play great.

For this round of Startupify.Me, we’re selecting a small team of software developers based on how prepared they are to become technical cofounders and play a leadership role in a new business. We’re building a flight simulator for technical businesses to provide you with the opportunity to practice the required skills in real settings, make some mistakes, learn, repeat. The first step will be leaving the cozy confines of employment and learn how to eat what you kill! Contact me directly if you’d like to apply.