/ Startup Life

You're Always Going to Trash Your First Startup

Ignorance is bliss.

I sat there, deep in thought. Perhaps there was some other way to monetise? There must be. There must be some avenue that I hadn't explored yet. After all, this problem was pretty trivial and I felt like my brain should be up to the task. I would find the answer.

Two months later I shut my last startup down for good.

What it means to fail fast

There's a lot of advice that gets thrown around in the startup community about "failing fast". It seems to me that many people read from this hymn sheet without ever fully grasping the lyrics.

"Fail fast" – they chorus – "you need to validate your product-market fit as soon as possible."

Crowds of heads bounce vigorously up and down in agreement like the dashboard of a Vauxhaul Astra lined with nodding dogs. "This. Is. LEAN STARTUP." - they chant, as Eric Ries throws crumbs of motivation down to the devoted wantrepreneurs from atop his dais.

"Basecamp." – Jason Fried mumbles from the corner.

To them (the people who say it) it makes sense. To them it makes sense because they have the experience to understand the context. They have acquired the different points of view to validate their beliefs.

I'm not a big fan of startup metaphors because you can turn any old bullshit into one. Like: How riding my bike without hands taught me to let go and trust my instincts and so on. What happens next will take your breath away and restore your faith in humanity, etc.

But I will draw one similarity - as opposed to metaphor - from far outside the world of business and technology.

This is not a metaphor

I'm based in Egypt, at the moment, and in my spare time I enjoy kiteboarding on the Red Sea. To be dragged around on small plank of wood by a 10 square meter canopy takes roughly twelve hours to learn. You can ride around comfortably on your own after that.

When people finish their course the inevitable question comes: "Which kite should I buy?" – to which the somewhat less-inevitable answer is generally: "It doesn't matter, you're always going to trash your first kite."

It doesn't matter how good you are. It doesn't matter how well you can ride. It definitely doesn't matter how careful you are.

You're always going to trash your first kite.

Nobody believes it, though. Every beginner says "yeah, but I'll be different" – but they're not. I said the same thing. I wasn't. So where is the disconnect? Why the disbelief?

They just lack context, which is this:

You are relatively unlikely to trash your kite as a result of your own mistake. You are very likely to destroy your kite (and yourself) by failing to spot a mistake someone else is about to make.

When you first go out to ride independently it feels like everyone is out to get you. Like you're some sort of danger-magnet and every idiot is drawn to you incomprehensibly. It's easy to kill someone with a large kite and 4-5 lines under 600lbs of tension, so it's not unnatural to be nervous. "What the hell is wrong with all these morons?" is a common complaint of people who have been riding only a short time.

All it takes is one unexpected move by someone else, and you're toast.

Missing context

You don't know that the guy in front of you is a beginner, and he's about to fly directly into your path. You don't realise that the girl behind you is a pro, and is about to overtake you on the side you don't expect. You don't see that grandpa over there never looks before he turns, and he's about to turn right into you. And then it happens. It takes just one split second of someone else making a mistake, and now their kite is wrapped perilously around yours and you're about to get seriously hurt.

Your kite is trashed, your knees are bleeding freely and none of it was really your fault. The only mistake you made was lacking the experience to give you foresight.

And yes, that did happen to me.

This is what "fail fast" really means for startups. You do not know that which you do not know. Sometimes this fuels a naivety which can turn out to be an advantage. Most of the time though, much like kiteboarding, it simply means you don't realise how fucked you are until it's too late.

There's only one way to get past it: Experiencing yourself. No amount of blog posts or startup books or TED talks can cure this one. You have to live through it.

I tried and failed hard at about 7 different startups and side projects before I found something that worked. I learned a great deal from it.

The paradox

The paradox – which doesn't really get talked about – is that it also works the other way around.

You don't know what love feels like until you've been in it. You also don't know what success is like until you've been enveloped in its warm embrace.

No matter how often people tell you to "fail fast" – and you nod in agreement – it's very hard to fulfil when you don't recognise that failure has occurred. We are made hopelessly optimistic by our entrepreneurial nature. We don't just have belief; we have faith. Faith that success is just on the other side of The Dip. That a lack of success indicates we should work harder.

In hindsight, as is so often the case, it all becomes clear. That relationship could never have worked out; it was doomed from the start. You spot every mistake, every hole, every warning sign that you previously ignored. So you try, and you try some more. Then one day you experience the "real deal" and suddenly your perspective takes a 100ft leap. Everything is different. (This can happen more than once, both in love and startups)

So this is the problem we face: You don't really know you will fail until you've already failed. You don't really know if you'll succeed until you've already succeeded.

Catch 22. You're always going to trash your first startup.

Once you understand and accept this, it starts to get interesting.

There are the mistakes which cannot be prevented, there are the mistakes which you cannot progress without, and then there's the blissful ignorance to carry you between the two.

Embrace it.

John O'Nolan

John O'Nolan

Founder at Ghost.org. Writes about open source, startup life, non-profits, and publishing platforms. Travels the world with a bag of kites.

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