Recently I decided to leave my job at Thomson Reuters to go all in on an unfunded startup that I started with Kevin Marshall.  This was a remarkably easy decision, but one that took me a long time to even approach.  

I’ve read about risk tolerance and how it’s a major factor in defining an entrepreneur (along with several other things) and realized it was a characteristic that I thought I had myself, but wasn’t demonstrating.  I’ve considered myself an entrepreneur since we first started Chalq in early 2007, but even then it was a nights and weekends project for me (Matt and Napoleon did work on the company full time). I wasn’t able to go all in on Chalq because I hadn’t properly identified my risk profile.  

Since Chalq failed in 2008, I’ve made a point to put myself in a better position to succeed in my next company.  Specifically:

1. I’ve saved money by significantly cutting down my living costs (my main risk concern).
2. I spent 2 years aggressively building my network of entrepreneurs and investors.
3. I’ve spent significant time in defining and refining what I believe are the skills needed by a non-tech founder of a web company (this will be an entirely separate post).

What is important is identifying what your risk tolerance on a personal level is.  For me it was the $0 mark and related to #1 above.  I didn’t want to go into debt, so I made sure that if I created another opportunity I would execute on it without it feeling risky.  For others it may be something completely different (opportunity costs, knowledge insecurity, confidence in your idea/team, etc…), but knowing what it is makes all the difference.  

If your dream is to build things from scratch and own what you build, identify what those points of risk are and eliminate them.  It took me 3 years to do this properly, and now I have the chance to work on my dream.  The best part is, it doesn’t feel the least bit risky.