• 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 assumpti...

As with so many lessons in business, I learned this one the hard way.

For years, I was terrible at distinguishing between "this needs attention" and "this needs my personal attention right now".

I cancelled too many vacations to admit to.

Tofino.

New York.

Nicaragua.

Countless others.

Plans abandoned because something came up at work that seemed too important for me to leave. 

And then there was Coldplay.

I had tickets to see them on a Friday night. I’d been looking forward to the show for months.

Then a customer had an urgent issue. A major pivot with a hundred moving parts that they said needed to be implemented ASAP.

So I gave the tickets to my assistant and stayed behind to deal with it.

Monday morning, my assistant shared something rather interesting.

The customer had been at the Coldplay concert.

Apparently, they had decided their urgent problem could wait until Monday.

Of course, I hadn't.

It's funny now.

It was considerably less funny at the time.

The le...

Every founder eventually encounters a moment when the path forward appears blocked.

The bank says no.

The investor passes.

That candidate you really wanted declines.

The market shifts.

The numbers don't work.

The opportunity you've been working toward suddenly feels out of reach.

In moments like these, it's tempting to treat the obstacle as a conclusion.

To assume the answer is no - permanently.

To scale back the vision.

To make the situation mean something about you personally as the founder.

Then to abandon the idea and move on.

But one question has shaped more growth decisions, acquisitions, financing discussions, and strategic opportunities in my career than almost any other:

What would need to be true for this to work?

A number of years ago, I was involved in an acquisition that looked dead before it even started.

The company had come off a difficult year. But an excellent opportunity to expand ahead of schedule (through the acquisition of a competitor) came o...