The Last Honest Realtor
Welcome to The Last Honest Realtor, your exclusive, behind-the-scenes pass to the twists and turns of the Toronto real estate market. Hosted by David Fleming of Toronto Realty Group, this podcast offers an unprecedented look behind the curtain, presenting the local real estate scene with a mix of unapologetic honesty and entertaining cynicism.
David doesn’t just talk real estate—he lives it. With years of experience under his belt, he's here to share the unvarnished truth about what it really takes to buy or sell in Toronto. From the big wins to the frustrating pitfalls, get ready for a behind-the-scenes journey that promises both information and entertainment.
Whether you’re a first-time homebuyer, a seasoned investor, or just a real estate enthusiast, David's insights will equip you with the knowledge you need to navigate the market. Expect practical advice on everything from staging and junk removal to listing and making the sale.
Tune in to The Last Honest Realtor and experience Toronto real estate like never before. Be informed, be entertained, and most importantly, be ready to see the industry through the eyes of someone who can handle any challenge the market throws his way.
The Last Honest Realtor
Ep. 36 - STORYTIME: Million-Dollar Gambles: Real Estate’s Tale of Hubris vs. Humility
Some sellers think their home’s value can never go down. Others learn the hard way that the market doesn’t care about what they want—only what buyers are willing to pay. So, when a seller turns down a great offer, convinced they’ll get more later, what happens when reality hits?
In this episode of The Last Honest Realtor, host David Fleming shares two gripping real estate stories that highlight the thin line between confidence and catastrophe. One seller swallows their pride and walks away with a win. The other refuses to budge—and pays the price. This is real estate psychology at its most brutal.
In This Episode:
- Roulette with Real Estate – Why some sellers gamble with their home’s value and lose.
- Hubris vs. Humility – The two mindsets that define who walks away with a win.
- The Psychology of Price Anchoring – Why sellers struggle to accept less than a past offer.
- Stock Market vs. Real Estate – Why people treat homes differently than stocks—and how that backfires.
- The $100K Mistake – A real-world example of how stubbornness cost one seller a fortune.
Timestamps:
00:00 – Introduction: What happens when sellers refuse to face reality?
03:45 – The casino analogy: The psychology of real estate risk.
08:30 – The West Toronto story: When waiting costs more than selling.
15:20 – The Newmarket disaster: A masterclass in self-sabotage.
22:10 – How hubris turns small losses into massive ones.
28:30 – Why price history doesn’t matter when selling.
34:15 – Lessons from the stock market: Would you refuse to sell at $160 if you bought at $100?
40:00 – Final thoughts: When to accept reality and move on.
Don’t Miss:
- Why sellers struggle to accept a lower offer—even when it’s the smart move.
- The #1 mistake that turns a small price cut into financial disaster.
- How to tell if you’re making decisions based on reality or emotion.
Subscribe to The Last Honest Realtor for real, unfiltered real estate insights every week.
Like, comment, and share: Have you ever seen a seller refuse a great offer and regret it later? Let’s discuss!
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