How Failure Looks From the Outside

Whenever startups go through some big challenge there’s always two completely predictable reactions, and they’re both humorous to watch and wickedly contrasting:

1. The Entrepreneur’s Nod:

Other entrepreneurs acknowledge, either silently or out loud, that they realize tough things occasionally happen. A term sheet that gets pulled. A CTO leaves. A company runs out of runway and has to shut down. These things happen. A lot. Everyone in the entrepreneurial community knows it and acts with empathy rather then disdain or laughter.

It’s largely what makes up an entrepreneurial community.

2. The Outsiders’ Snark:

People outside of this community, however, are accustomed to things planned by committee and never seeing the light of day until it’s totally de-risked. So when they see a post-mortem, a team of two co-founders going separate ways, or an awkwardly handled crisis they’re quick to focus on the negative. They say what they would do.

Quite simply, outsiders see unintended results as a failure. And of course, failure seems to be bad and preventable.

If there’s one thing that every successful entrepreneur I know has as a common denominator it’s this:

Failure isn’t bad. It’s a step.

Every entrepreneur has to painstakingly endure outsiders telling them why they will fail, why their attempt did fail, and why they should stop failing and just do something safer. We’ve all lived it.

What every beginning entrepreneur needs to know is that the only failures that really matter are:

  • Breaking promises. With anyone.
  • Not delivering. (See the above bullet.)
  • Hurting others to justify your end. Irreparable.

Lessons From the Trenches

We know for certain that Project Skyway entrepreneurs will go through tough, gut-wrenching times and nothing will change this fact. Some people want to portray these as failures for the community, the program, or the entrepreneur. However, since we have a unique laboratory I’d like to use some cases as examples in hopes that minds can be refocused away from “failure” and towards “what’s next”:

Example 1: We had two companies decide to opt out before the first cycle got under way. Our hope is that two people are pretty committed before they get married. Failure on theirs or our part? Only a naive perfectionist would say so. Not failure by a mile. Smart decision making.

Example 2: We had a company of three co-founders decide to split up and go separate ways 2 weeks into the our first cycle. There’s no way they’ll say this was a bad thing. They would say it was both necessary and that they were lucky it happened early rather than later. In fact, since one of them continued to participate in the program he feels that without a doubt that it was one of the best things that ever happened in his life.

Example 3: In the same cycle we had another company decide, after changing their original idea, to move to NYC part way through the program. They felt their new idea could be better launched there. Again, no one close to the situation would say it was a poor move. We wouldn’t and they wouldn’t. End of story. In no way is it a failure when a company decides to move to a market they strongly feel is better suited for them.

Many startups will eventually hit the deadpool. Many will have teams break up. Many will change form entirely, reinventing themselves. Out of five Minnesota companies that attended Y Combinator, the uber-successful Silicon Valley accelerator, one broke up and one closed shop. It seems Y Combinator isn’t the magic wand everyone wants it to be. But I don’t know a single entrepreneur that would point at those two companies and decry them as failures. Not one.

Failure is just a step. One that we see as our mission to help our entrepreneurs go through with empathy, guidance, and persistance.

Failure will happen. The key is to get up and keep fighting.

About Casey Allen

Co-founder of Project Skyway
This entry was posted in entrepreneurship, MN Ecosystem, Project Skyway. Bookmark the permalink.

One Response to How Failure Looks From the Outside

  1. Patrick E. Donohue says:


    Awesome post. Well put. Many people around our community have “talked” about an accelerator or similar model and you guys made it happen! You are actually standing up and fighting for a real solution to spurring our entrepreneurial community. There has been no shortage of “enthusiasm” in our community, but there has been a lack of real action. You have taken action when many others have only talked about it, and for that, you win no matter what the long-term outcome is of your skywalkers!

    Patrick Donohue

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