Accelerating Your Startup by Failing Often

Failing fast is pretty much a mantra of modern startups. But how about failing often?

People are pretty scared of failure. I can see why. Failing at stuff kinda sucks. Failing at stuff makes you feel like a failure. As if you’ll fail more in the future because you’re failing now. Or that you’ll never be a success.

There’s some truth in that. Sometimes—though in my opinion very rarely—failing at things means you’re genuinely bad at them, and you should stop.

Startups aren’t one of those things.

Startups, you will fail. You’ll fail a lot. Your first startup, unless you’re a well funded superhero, will probably be awful. You’ll make the same mistakes everyone constantly warns you about. Here’s a list to check off:

  • Build something nobody wants
  • Build it in secret for 6 months
  • Release and alpha, then a beta, then a beta production release, then a public preview, then a limited release
  • Do a soft launch because you’re worried about server load
  • Realize it’s not working out and try to get ‘crunched
  • Run out of money and shut down

You’ll find a lot of articles telling you how to avoid these pitfalls.

Don’t listen to them.

By making these mistakes yourself, you can avoid them in the future. If you avoid them all first time you’ll think you’re awesome, when in reality, you’re just lucky.

That way, every time you build a startup, you’ll do better than last time. Trust me, I’ve built a few.

The first pivoted dramatically after 2 weeks, then shut down after 10 months with no revenue.

The second actually made money. After 7 months at zero, we finally got to a stage where it was comfortably paying for itself. It even turned a small profit.

But HelpDocs makes money already. We’re further along after 5 weeks than we were after 9 months of our last startup. And people actually like the product more.

Sure, you could attribute that to having a better product. Maybe you’d be right. But I like to think it’s more because we know what not to do.

We’re not wasting time or money on things that won’t move the needle for us.

We’re investing in the future still, but firmly rooted in the present.

We’re not preparing for scale, in stealth mode or raising funding.

We’re just shipping awesome product every day and giving A+ customer support.

I think you need to have at least experienced the frustrations of doing things the wrong way to recognize the right. Even if that’s in someone else’s terrible startup. You need to have at least seen it happen.

At the end of the day, the only foolproof way to hack success is just to fail a lot of times first.


I’m just a guy from the UK that’s okay at writing, better at startups, awesome at making coffee.

This is day 18 in a 365 day writing experiment. You can check out why I’m writing every day here.

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