The Six-Figure Mistake That Almost Broke Us

That time we lost $100,000 and lived to tell about it — plus what it taught us about calculated risk

In business, like in life, sometimes the most painful lessons stick with you the longest. For Emily and me, that lesson came with a price tag of nearly $100,000 — a sum that would make anyone's stomach drop.

The Costly Mistake

It was a seemingly ordinary decision that spiraled into financial disaster. Simplified had been growing steadily. Our planners were selling out, which is usually a good problem to have. When customers kept demanding more, we did what any ambitious business would do: we tried to fulfill that demand.

Our manufacturer approached us with a solution. They could produce another run of planners, but there was a catch — they'd need to use a different paper. "Is it good paper?" Emily asked. They assured her it was. Being diligent, she requested a sample. They sent one with printing on only one side, and it looked perfect.

What we failed to consider was how that paper would perform with double-sided printing. When the entire order arrived, the paper was practically see-through — like tissue paper with ink bleeding through both sides. The planners were completely unsellable.

Just like that, $100,000 vanished.