Of all the cross-border mistakes that land on my desk, one appears more than any other: a Canadian entrepreneur who set up a US LLC because a website, a US advisor, or a YouTube video said it was the simplest option. It usually is simple — for Americans. For Canadians, that same simplicity can quietly

Every fall, hundreds of thousands of Canadians head south to trade slush for sunshine. And every spring, a few of them discover — usually at the border, or in a letter from the IRS — that their winters in Florida or Arizona came with a tax filing obligation they never knew existed. Here is the

Here is a conversation I have with Canadian business owners more often than I’d like: a company has been selling into the US for three years, sales are growing nicely — and then a letter from the IRS arrives, or a US customer’s procurement department asks for a W-8BEN-E, and suddenly nobody is sure whether