Part of the Sovereign Canadian Thought Leaders series, profiles of the writers, investors, and thinkers who shaped how I think about money, freedom, and geography. This is personal documentation of what I’ve read and what I’d actually use, not financial advice. Read me as a peer taking notes, not an analyst issuing a rating.

For a lot of people today, flag theory means Andrew Henderson. He didn’t invent it. What he did was attach a slogan to it, then a YouTube channel (I’m a subscriber), a book I really should read, and a consulting firm called Nomad Capitalist, and then repeat the slogan until it stuck: go where you’re treated best.

That’s a real achievement, and it’s why he belongs in this series. His questions are good ones, and I want to read them through a Canadian filter. Henderson is a skilled popularizer and the founder of a consultancy positioned at the premium end of the market, and the hinge of his own story, giving up his American citizenship, is a move Canadians don’t need to make. Take his playbook straight from the American version and you can end up solving a problem we don’t have while missing the ones we do.

Part of the Sovereign Canadian Thought Leaders series – profiles of the writers, investors, and thinkers who shaped how I think about money, freedom, and geography. This is personal documentation of what I’ve read and what I’d actually use, not advice. Read me as a peer taking notes, not an analyst issuing a rating.

I’ll be upfront about why Saad is in this series, because he’s the odd one out. Everyone else I’ve profiled here sells something adjacent to money. Saad sells none of that. He’s a marketing professor at Concordia. There’s no newsletter telling you which junior miner to buy. What he has is the layer underneath all of it: a theory of why humans want the things they want, and a very loud second career arguing that Western societies have talked themselves into decline.

He was also, for decades, the one subject in this series who was genuinely Canadian and stayed. He came to Montreal as a refugee, earned tenure at Concordia, and dug in. That made him a living counter-argument to the whole flag theory playbook: proof that you could choose voice over exit. Then, on Joe Rogan’s podcast in May 2026, he announced that his family was moving permanently to Oxford, Mississippi, where he has taken a position at the University of Mississippi. The man who stayed chose exit after all. The reasons he has given, as reported by the National Post, include safety, the threats he says made it untenable to keep working at Concordia, and, in the paper’s later reporting, a tax system he says makes it nearly impossible to save enough to retire. For a blog about Canadians weighing that exact decision, it is the most interesting thing he has ever done.