The Biases of an Unsuccessful Entrepreneur

What have I created on a road I am yet to travel?

James Rickard
wandering developer
4 min readMar 21, 2016

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Have I peppered the road before me with ruts as deep as my arm, and speed-bumps like a Mexican highway, even before I have walked it? This is the problem with a bias — They are created on a road that has not been walked.

The Same Path Home (image provided by BossFight)

Startups are hard work. Finding the right idea to build that fits into a market. In the trenches, working and trying to be successful. My projects have never made a profit, never made any money. I have been at the failed-end of start-ups, wishing for success and talking about how hard things are.

Over a glass of wine a friend and I talked about a project he is working on. We were talking of ways to make his project work and become a success. Their business has found a pressure point and need to think about how to make money, rather than spend years building a product. Something he said caught my attention:

We need to make money, so therefore selling a package our clients assemble will be the quickest way into the market.

Maybe you missed it. But it caught my attention like a streaker at a football match. The bias of a previous thought. We need this, so therefore that. A casual thought; a previous thought had created a truth in his current the situation. It was a crux of his argument for moving in that direction.

We need this, so therefore that.

It was not his thought that was the problem. It was the certainty of which he spoke it, the way that it came out into the open air as if a truth had been spoken.

I am not disagreeing with what he said, in fact it may be the way that they make money — for me, it was the “Post hoc ergo propter hoc” that caught my attention.

And so, we talked of biases, and the fallacies we believe because… we have a thought and we therefore have decided.

My Startup Bias

It seemed so clear to me, when my friend spoke his bias out loud. The way that a previous thought had become The Only Way To Move Forward was striking. Our discussion that followed shed light to many of my biases where I have done the same things, making reality out of a single thought.

How many decisions have I made, thinking from my little bubble? How many business choices have I made, all from my own little world?

My life as an entrepreneur, working day-to-day in little ideas, that have stayed small. What little things I have crafted, with the hope they will grow to become products one day.

”We dig our own graves — using our own bias as a shovel.

The Biases of an Unsuccessful Entrepreneur

Does my previous experience really affect the future? Have I created a start-up bias so deep that I am doomed to repeat the same thing? Does one failure beget another? Is there any hope out of my failed attempts? Does this open the road to possibilities or does it complicate things?

What hidden bumps or ruts has my past experience created in the road I have not travelled?

Have I peppered the road before me with ruts as deep as my arm, and speed-bumps like a Mexican highway, even before I have walked it? This is the problem with a bias — They are created on a road that has not been walked.

What kind of “Post hoc ergo propter hoc” thought pattern have I created? My Bias created from My Experience, and what can I do about it?

Community of Ideas

Discussion brings these biases to light. Talking about things I have not considered, or factored into my opinions, will create a better pathway.

Surrounding myself with people who will spot a bias, and point it out is what I need to stop driving the road I have created. A community of people, thinking about the helping my ideas along the road to freedom.

Communities can create, strengthen and grow a bias — communities are great at generating self-created feedback loops — but having someone else to look upon my biases, who can point out my thought fallacies and then talk about them, is better than nothing.

It is better than creating my own biases, from my own experience.

A variation of this post was originally posted at Frodosghost. James is a serial entrepreneur of small ideas — I am not successful.

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