Failure isn't cute. It's screwing with your head.

Annie Passanisi

Failure isn’t cute.

It’s screwing with your head.

— Jonathan Eyler-Werve

Startup culture loves to talk about “cute failures.” Cute failures are the ones where mistakes were made, but no one got hurt and everyone was moments away from greatness: “We were almost out of money when we pivotedperfectly!

Cute failures get TED talks. Uncute failures get disappeared.

Uncute failures are the teams that spent so much time bickering they never launched. The bad hires (or unfilled roles) that tanked an otherwise good idea. The long, lonely trudge for funding that never got anywhere. Mental health problems of every variety. The dinner table conversation with the spouse who needs to know when and how you will shut it down.

I’m not going to talk about my uncute failures here. The company that closed without a single dollar of revenue. The company that fired me two days before my equity vested. The time I told my lawyer, “Thanks for the advice, but my partners would never do that.” (They did.) I won’t talk about the time I was so overwhelmed by the growth of an enterprise app that I didn’t leave my bedroom for two weeks.

I don’t write about this, except through a gauzy veil of cuteness: Look how startup-legit I am. No names. No details. Few useful lessons.

We almost never see business reporting about uncute failures.

The recent New York Times longread on Amazon’s work culture set off waves not because Amazon’s grind-or-die ethos was a secret, but because it is so rare to find reporting on technology companies as something other than slightly magical, possibly threatening, wonderlands. Unicorns, indeed.

Publicity-hungry companies feed this. Our media (social and traditional) is full of launch announcements, new funding achieved, products in beta. Hype.

The real dealings of startups, particularly the early stage companies, go unreported. Well-made products fail to get traction. Investment rounds close with terms that burn early employees. Startups shut down after years of work, and no one writes a thing.

Even success is shrouded; unless you know the founders personally, it’s often hard to understand an acquisition. Is it a happy exit or a salvage operation? The press releases are identical.

Uncute failure legitimately sucks. Here’s how to learn from it.

 

What does this mean to a founder? It means that nearly all of your data about startups is skewed.

And I’ll argue that avoiding the obvious mistakes isn’t just a prereq. In a lot of cases, it’s a pretty solid start towards success. In many markets, particularly the less glamorous B2B stuff, what it takes to be successful is not doing it horribly wrong for several years in a row.

Point the boat in the right direction, and keep it off the rocks. But you’ll need data. You need to know where the rocks are.

Some ideas:

  • Accept that media channels are full of skewed data — hype — and recognize the danger this poses to your psyche. There is a thin line between inspiration and spirit-crushing intimidation. Moderate your intake. Enjoy reading Fast Company as the fashion magazine it is.
  • Know that uncute failure is really useful to hear about, and know that it isn’t going to get talked about publicly. You’ll need more honest venues than panels or Twitter or blogs, and that’s probably offline and one-to-one.
  • Do random sampling. If you’re looking to start a high-growth tech company, research the Techstars or YCombinator classes of years past, and look up the founders. First, notice how many of these companies still operate (spoiler: half-life of around a year). Second, collect the names of founders and early employees. Get a Twitter list going.
  • Cold call. Use Twitter. Make it “a project,” which helps initial outreach feel non-creepy. For example, put “Currently trading coffee for data for any [person type] in the [location] [community]” in your Twitter or LinkedIn bio.
  • Buy that coffee, and get people talking. Good leading questions are a skill you can develop over time, but getting people talking is easier if you shut up about your company/idea/career. Seriously. Listen now, hype later.
  • Join the counterculture. At Polymathic, we host Founder Therapy, a free monthly event that focuses on helping each other instead of selling to each other. And we talk about failure — real failure — honestly, openly and without gloss.

The good news here is that finding real stories of failure — which is to say, unskewed data on the outcome of most startups — is high value, and it’s not that hard if you try.

You’ll meet people who have been through seriously hard stuff and yet there they are, drinking your coffee, doing fine. Here is the kernel of truth in cute failure: People are resilient. People learn from mistakes. People figure it out and get stronger. You will too.

And if you can take those insights and avoid blowing up your company for a few years, there’s a good chance you too will be remade by a PR team into a visionary business leader, rising above your cutest failure yet, always ready with the perfect pivot.

 

The author builds products for Polymathic. Polymathic LLC provides the best of Chicago’s programming, design & product talent. We build greenfield software for industry-savvy entrepreneurs, private equity firms incubating products, and established companies looking to innovate.

And, as our reputation attests, we throw a helluva party.

 

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