01/22/2026
Most business owners don’t realize this until it’s too late.
You can build a successful company, sell it for a great price…and still hand over a massive chunk of it to the CRA.
A business owner once said to me:
“I didn’t spend 20 years building this just to give half of it to the government.”
And yet, that’s exactly what happens far too often.
The biggest mistake? Waiting until a sale is already on the table to think about tax.
In Canada, there’s something called the Lifetime Capital Gains Exemption that can allow qualifying business owners to sell shares with little or no tax.
With the right planning done early, that exemption can sometimes even be multiplied using family structures.
Same business.
Same sale price.
Very different outcome after tax.
This isn’t about loopholes or aggressive strategies. It’s about understanding the rules before they matter.
The biggest regret I hear after a sale isn’t about the price…it’s, “I wish I had known this sooner.”
If you’re a business owner who might sell one day — even years from now — this is worth learning early.