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In this episode of the Last Honest Realtor, David Fleming draws on his own experience investing during the tech boom and bust of 2001-2002 to ask an important question: “How and when should you exercise a loss?”

David also analyzes a recent media article about sellers who exercised a massive loss on a home in Peel Region and explains why the loss never should have been that large to begin with. In this episode we explore why people struggle to "exercise a loss," how emotions cloud financial decisions, and why sometimes the best investment move is accepting a loss and redeploying your capital elsewhere.

In This Episode:

• 01:35 — The investing mistake that changed my life
• 09:32 — Why I wanted to sell—and didn't
• 15:16 — The danger of hindsight
• 16:23 — The Brampton home that lost $950,000
• 31:30 — Why sellers must stay ahead of a falling market
• 34:39 — Reinvesting instead of holding on
• 38:36 — Why real estate owners struggle to sell at a loss
• 40:08 — When selling at a loss can actually make financial sense

Whether you own a condo that's fallen in value, an investment property, or you're simply trying to understand the roller coaster of the Toronto housing market, this episode offers an honest look at one of the toughest decisions investors face.

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