The Triad of Startup Suckiness – or – Have you hugged a founder today?

Crying Startup Founder

Today marks the first of what I hope will be many of the Fail.Learn.Grow. conversation series. The mission of FLG is to help entrepreneurs understand and accept that failure is part of the entrepreneurial journey. By opening conversation, we hope that we can prevent even a single suicide or help to lessen one person’s depression.

Note that I used the word “accept” and didn’t use the word “embrace” because the word embrace carries with it connotations of enjoyment or pleasure. Failing sucks, failing is hard, and failing is unpleasant, but just as children learn that going to the dentist is something that will happen and they can’t avoid it, so is failure part of the entrepreneurial journey.

Along that same vein of thinking, lately I have seen a lot of Twitter posts and blogs about depression and the challenges of startups. As a 10x+ startup founder I am not immune to these virtually unstoppable emotional experiences that surround building startups. What I have found is that my ability to cope with them has improved and that as I have become more aware of why startups are so hard, it makes it just a little easier to continue forward.

This is what I believe is the triad of startup misery:

  1. Uncertainty – Virtually every fear in our lives is driven by uncertainty of what will happen in the future. When we are babies it’s fear of mom leaving the room, when we are teens it’s fear of not being accepted by peers, when we are adults our fears tend to center around things like mortgage payments, college funds & health.

 Startups carry with them the same uncertainty. When a founder builds a startup, no matter how cocky and confident they may appear on the outside. The fact is, that founder stays up nights worrying about the future. The uncertain future. Will I fail? Will I succeed? Will I look back with regret? Will I be humiliated?
  2. High Likelihood of Failure – Every entrepreneur is aware (or should be) that the odds of their business succeeding are small and that risk of failure goes up substantially when you build tech startups. Want to open a fence repair company, odds are good you’ll be in business in two years, but if you want to revolutionize the Internet with a service built around a new protocol you’ve worked on, the chances are that you will not be in business in two years. Knowing this fact is daunting. Being a startup founder requires a certain amount of foolish optimism or at least a willingness to face very poor odds. The knowledge of this likelihood of failure is a hard cross to bear.
  3. Opportunity cost – Every single startup founder I know has friends who are not startup founders. Those friends are lawyers, doctors, investors, teachers, you name it, they have “normal” jobs. Every day they wake up and the odds that their job has disappeared despite being hard working, intelligent and reliable are miniscule.

Every single startup founder I know has a persistent recurring thought about the stability and predictability of a real job. More than that though there is a fear of lost opportunity.

Take me for example. Twenty years of building startups has made me a jack of many trades and an expert in none, except in building startups. Could I go become a consultant? Could I go become a lawyer? When you focus on building startups, other opportunities are not as available to you. I am utterly unemployable because of the entrepreneurial path I have chosen. Ok so perhaps I’m being dramatic but the truth is that the further down the entrepreneurial path you go, the more certain it is that you’ve passed up other more stable opportunities.

One last thought worth considering is that I believe age has a direct correlation to the willingness to accept this triad of challenges. When I was seventeen…well, lets just say I’m lucky I’m alive because of the risks I was willing to take. When I was twenty-nine and found myself with a family, my tolerance for risk decreased and as I approach forty I look for ways to succeed with less risk.

So there you have the triad. The above list represents the three recurring concerns that every startup founder deals with in some way shape or form on a daily, weekly or hourly basis. If you know somebody building a startup, give them a hug, because they are probably dealing with a lot more than they let on.

This article was originally posted on my blog at

Arlo Gilbert

#Inventor #Investor #Founder #Hustler #Husband #Dad - Voted most likely to find a loophole - Advising startups & running