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The $3 Trillion Ecosystem: Inside the Mind of TRREB’s CEO Guest: John Di Michele, CEO of the Toronto Regional Real Estate Board.

Is the real estate market on life support, or are we just in a "quagmire" of uncertainty?

When you sit at the center of North America’s largest real estate data ecosystem, you don't look at headlines - you look at cycles. In this episode, Simeon Papailias sits down with John Di Michele, who oversees the data and infrastructure for over 70,000 agents.

John provides a bird’s-eye view of the industry that simply doesn't exist anywhere else. This isn't just a conversation about stats; it’s a masterclass in interpreting the current market volatility and understanding why a massive turnaround is often just one "overnight" shift away.

In This Episode, We Cover:
The "Overnight" Pivot: John analyzes the cycles of 1996, 2008, and 2017 to explain why the current lull is a pressure cooker waiting for stability to return.

The Trump Effect & Tariffs: A deep dive into how geopolitical volatility creates a "market chill" and what it means for Canadian real estate.

Policy Wins You Need to Know: The inside story behind the lobbying efforts that successfully removed HST/GST on new construction.

The Human vs. The Machine: Why AI will never replace the "human sense"—the ability to smell a mold issue or know the unique history of a specific block.

Realm & The Future of Search: How voice-command AI and new ecosystem tools are removing friction for high-volume producers.

We started Broker's Playbook to make the Real Estate Industry a better place, and your subscribership means the world to us. Please visit https://brokersplaybook.com/ to learn more about our mission to create better Agents and Brokers.

Find more content on our YouTube Channel - https://youtube.com/@brokersplaybook

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What’s really happening in the Toronto real estate market in 2026?

In this episode of the Broker’s Playbook Podcast, Winson Chan, VP of Sales at Tridel, breaks down how developers actually think about market cycles, pre-construction, and long-term housing demand.

If you’re a real estate agent, investor, or buyer trying to understand where the market is heading, this conversation gives you a strategic edge.

We cover:

The real difference between developer vs agent mindset
Why pre-construction is misunderstood right now
How market cycles actually repeat (1990s vs today)
The impact of interest rates, confidence, and buyer psychology
Why today’s “slow market” may be the biggest opportunity
The role of the Bank of Mom and Dad + wealth transfer
Where Toronto real estate is heading next

This is not surface-level advice. This is how decisions are made behind the scenes.

If you want to go deeper into the strategies top agents are using right now, join the Broker’s Playbook community.

👉 Comment PLAYBOOK or visit: https://brokersplaybook.com

We started Broker's Playbook to make the Real Estate Industry a better place, and your subscribership means the world to us. Please visit https://brokersplaybook.com/ to learn more about our mission to create better Agents and Brokers.

Find more content on our YouTube Channel - https://youtube.com/@brokersplaybook

Send us Fan Mail

Artificial Intelligence is changing real estate faster than most agents realize.
In 2026, the agents who win won’t be the busiest — they’ll be the smartest.

In Episode 107 of Broker’s Playbook, Simeon Papailias sits down with engineer, marketer, investor, and Filer AI founder Ankita Sharma to break down what AI actually means for real estate professionals.

Is SEO dead?
Will AI replace real estate agents?
How is information asymmetry collapsing?
And what separates strategic agents from average ones in an AI-driven market?

In this episode, we cover:

• AI vs human intelligence in real estate
• Why SEO is evolving into AI Engine Optimization (AEO)
• How AI is eliminating costly transaction errors
• The future of PropTech in Canada
• Why Q1 is the time to build while others wait
• How smart agents use AI to increase leverage, not lose relevance

Ankita shares how a $40,000 transaction mistake led her to build AI-powered legal infrastructure designed to reduce friction, improve compliance, and modernize real estate closings in Ontario and Alberta.

This conversation is essential for:

Real estate agents
Brokers
Investors
Entrepreneurs
Anyone building in a changing market

The biggest threat to your career isn’t the market.
It’s refusing to evolve.

Subscribe for more conversations on real estate strategy, investing, and the future of the industry.

We started Broker's Playbook to make the Real Estate Industry a better place, and your subscribership means the world to us. Please visit https://brokersplaybook.com/ to learn more about our mission to create better Agents and Brokers.

Find more content on our YouTube Channel - https://youtube.com/@brokersplaybook