The Wealthy Barber Podcast #45 — Jon Flynn: Wow, The Canadian Housing Market Is Leaking And It Won't Stop Raining
Feb 24, 2026
Jon Flynn, Realtor and creator of the Jon Flynn Real Estate Stats YouTube channel, breaks down Canada’s housing slump with data-driven clarity. He explains how he spotted the downturn, where prices may slide next, AI’s wildcard effect on jobs and housing, controversies like commissions and trust-fund scandals, and why overpricing, negative equity and speculative builds are causing markets to stay stuck.
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Market To Grind Lower Like The 1990s
- Flynn expects a slow grind lower similar to the early 1990s rather than a quick snapback, with bottoms not likely until after 2026 by historical cycle measures.
- He attributes the long slide to late rate hikes that allowed a blow-off top and expects intermittent larger downward legs.
AI Is A Wild Card For Housing Demand
- AI is a wildcard for employment and housing demand; mundane tasks like policy drafting collapsed from months to seconds in Flynn's example.
- Flynn notes office jobs may be hit first which could reduce demand for housing tied to commuting and white-collar employment.
Account For Realtor Time When Evaluating Fees
- Recognize realtors' low success rate and the unpaid time behind commissions; consider alternative compensation structures if it fit your needs.
- Flynn notes many agents waste ~70% of their time showing listings that don't convert, so align expectations on effort and fee.