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Chesterton’s Fence for Startups

If your market hasn’t been disrupted yet, it’s probably not because the natural competitors are stupid or lazy.

💻 We’re 40+ years into the PC revolution

🕸️ Web 2.0 is old enough to drive

📱 Smartphones are over a decade old

If a market is still inefficient, it’s probably *not* just because no one has thought to fix it with technology yet.

Before embarking on a journey that may consume years of your life, it’s a worthy exercise to ask *why* something hasn’t been done yet, or if several startups have tried, why it hasn’t worked to date?

“Chesterton’s Fence” is a principle that you shouldn’t start making changes to something until you understand the decision-making process that led to it. Practically, don’t remove a fence until you know why it was built in the first place.

If multiple startups have tried to do what you are attempting and failed, don’t assume a lack of smarts, hard work, or bad timing doomed them. Those *may* be the reasons. It’s also possible they hit a non-obvious barrier that halted their progress — and will halt yours too.

It is easy to sign off on a facile answer — a new technology or a modern UX are perennial favorite explanations to answer why “this time is different.” COVID has been a popular response in 2020. This kind of answer might get you funded, but it shouldn’t satisfy you.

Founders should have a clear understanding of why their forebears failed that goes beyond “they’re old.” or, “the market has evolved.” Those may be the right answers! But they shouldn’t be the default assumptions. Here are some ways to uncover hidden secrets:

⚰️ Talk to founders of failed startups

They’ll almost certainly be sour on the market and give you 100 reasons no one could succeed in it. Don’t let them discourage you, but do listen carefully to the specific issues they raise, especially those that you haven’t considered.

It is important not to absorb their negativity, but they’ll almost always help you uncover obscure regulatory tripwires, unspoken commercial strictures, and other impediments that are invisible to the uninitiated.

💰 Know thy payor

In many industries, there are gaps between the desires of the end-user of a product and the requirements of the entity that is paying for it. Lots of startups have died assuming that optimizing for the former will impress the latter.

Don’t assume you can intuit the commercial thought process underlying large organizations. The irrational behavior you perceive as a negative consumer experience is likely driven by an incentive structure elsewhere in the business. Try to discover it is *before* you start.

No amount of features in your app or brilliant innovations in customer service can solve structural impediments in your overall business model. There’s an elephant’s graveyard of startups that assumed they could.

It is true that “Boldness has genius, power, and magic in it.” Naïveté has proven to be a commercial lubricant in the past. There’s more than a little hubris in the founding stories of almost every successful business.

However, the presence of naysayers is not a sure sign that you’ve struck pay dirt. They may be Ghosts of Christmas Future come to warn you about the folly of your path. Hear them out.

The goal of discovering impediments isn’t to find an excuse to abandon the idea, but rather, to help navigate around obstacles more skillfully. It’s much better to find out about existential risks early in the process, rather than after you’re pot committed to a strategy.

“Research” doesn’t need to be exhaustive or academic. You don’t need to mitigate every potential risk. But don’t jump headlong into an opportunity without first asking some basic questions that could save you years of frustration.

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