The $67,000 Lesson

Years ago, my business partner and I started a credit monitoring company called Debt Monkey.

We had seen similar companies taking off in the U.S. and thought we could bring the idea to Canada.

We had the company.

We had the commercials.

We even had a beautiful spreadsheet showing us how much money we were going to make.

We were convinced.

Then I pitched the idea to my friend Barry, who had been an entrepreneur for years.

He asked one question.

“Have you guys tested this?”

Nope.

But we were pretty sure we knew what we were doing.

Six months later, I had lost $67,000 and taken out a second mortgage to repay friends who had invested with me.

It felt like I had just paid for my MBA in business.

When I told Barry what happened, he told me about the million dollars he had once lost on an idea he had not tested.

Apparently, my tuition was a bargain.

But I learned something from that experience.

Do not build something you have not proven you can sell.

That lesson stayed with me for years.

Protect cash.

Focus on profitability.

Test ideas before making a big investment.

Those are still good principles.

But lately I have been wondering whether I have let a 15 year old mistake make too many decisions for me.

That is the interesting thing about lessons.

Sometimes they protect you.

And sometimes, if you hold onto them too tightly, they become rules you stop questioning.

I am not planning to launch Debt Monkey 2.0 anytime soon.

I still believe in testing ideas.

I still want to understand how a business is going to make money.

But I also think there comes a point where you need to ask whether an old lesson still fits the business you are building today.

Because something can be useful for years and still eventually need to be challenged.

So here is the question I have been thinking about:

What is one rule you have been following for years that might be worth questioning?