It turns out, we do get to choose how to be an entrepreneur.

I have a modest and maybe even overly simple personal philosophy with which I view my life — I compartmentalize my entire existence into three basic buckets: social, business, and family. This plays out in many different ways, but today I am focused on my walls around business.

I get to observe thousands of entrepreneurs in action, and occasionally if not accidently these observations yield some high-level insights. And, like in many of my articles here at, I want to take the conversation up to a higher level. Today we are going to discuss philosophy.

My aim today is to break down entrepreneurial philosophy into two fundamental paths:

  • Pursuit of gain
  • Avoidance of loss.

You cannot build a successful business with an approach that minimizes the chance of failure.

Entrepreneurship is not a limp-in game where you manage downside risk. The best companies and founders do not factor in the consequences of the worst-case scenario, though each one knows it is a possible if not probable outcome. The best simply dismiss that thought. In doing so, they lighten the load and open up the door for better outcomes.

Outstanding startup founders have a philosophical ethos in which everything they do is a pursuit of gain. (I heard this gain/loss dichotomy expressed in a recent Tim Ferriss podcast and I cannot seem to shake the simple two-sides thought.)

Many of us are in a continual search for ways to simplify our chaotic business lives. I never stop thinking about ways to optimize various aspects. These might include a zero inbox, to-do lists, stand-up desks, strict calendaring, walking meetings, etc. You get the point. There are so many tools and tactics and so much thought leadership with the intent to optimize our business life.

Don’t stop doing that, but let’s make sure the core engine of your startup soul is running and operating the right way. So my question for you is, are you in a constant pursuit of gain or are you operating to avoid loss?