The most dangerous words in business

• The most dangerous words in business may be: "That will never happen.”

• Success has a way of making assumptions feel like facts.

• The exact disruption is rarely predictable. The vulnerability often is.
• Preparedness beats prediction.

Every founder eventually encounters a moment they were convinced would never happen.

 Not because they're careless.

 Not because they're inexperienced.

But because assumptions are necessary to operate a business. And by definition, assumptions aren’t always accurate and are subject to change.

We assume suppliers will continue to supply - and at a cost that fits our business model.

 We assume customers will continue to buy - and in the quantities we’re depending on.

 We assume key team members will stay.

 We assume capital will remain available - and that we can get more when needed.

 We assume borders will stay open.

 We assume technology will continue to work and improve at a reasonable pace.

Most of the time, those assumptions are reasonable.

Until the day, they aren’t.

A number of years ago, I learned an expensive lesson about assumptions through my very first startup investment.

 At the time, it felt like a winner.

 Strong demand.

 National media attention.

 A sizeable retail contract.

 Momentum.

 Then a single point of failure that everyone assumed would hold, didn't.

 An essential supplier couldn't deliver.

 It wasn’t a case that some of the product was delayed.

None of the product arrived on time.

 Critical deadlines were missed.

 Customers cancelled contracts and moved on.

 The company never recovered.

At the time, I thought the key lesson was about supply chains.

 Over the years, I've come to realize it was really about something else.

It was about vulnerability.

Specifically, the vulnerabilities we stop looking for because things are working.

 Because success has a way of making assumptions feel like facts.

Today, businesses are navigating tariffs, geopolitical uncertainty, AI disruption, shifting customer behaviour, challenges getting and keeping the right talent, and changing access to capital.

Most leaders are asking:

“What’s going to happen next?"

It's a reasonable question.

But I don't think it's the most useful one.

A better question is:

"What assumptions are we making today?"

And the even more important follow up:

"What happens if we're wrong?”

The future has always been uncertain.

What's changed is the speed at which conditions can shift and the number of variables that feel like moving targets. 

That's why flexibility, resilience, and regularly considering different “what if” scenarios have become such important competitive advantages.

The founders who navigate uncertainty best aren't the ones who predict every disruption.

They're the ones who continually challenge their assumptions before reality does it for them.

 Because the exact disruption is rarely predictable.

 But where the vulnerability lies usually is.

And being prepared beats prediction every time.