Issue #33: Test Your 'AI'ssumptions

Welcome back, everyone!

I've been thinking a lot about partnerships lately - not just the formal JV kind we explore in the Zoning In section below, but the everyday alliances that keep us sane in this business.

But before we get into it, I had to do it…

…because everyone is doing it, I had no choice but to join the plastic pantheon.

Behold: the Greg Mills Housing Hero™ action figure—complete with briefcase, laptop, hard hat, and boots (barefoot intensity sold separately).

If you want the Chatgpt prompt to make your own blister-packed alter ego, you’ll find it waiting for you in the Logical Links section below.

🧠 New This Week: Canadian CRE Sentiment Highlights

Read to the end—this is the start of something big.

Welcome to the first edition of our Canadian Commercial Real Estate Sentiment Tracker—a skimmable, AI-powered pulse check across the major sectors.

Each week, I feed the top headlines into my AI co-pilot, which analyzes tone, context, and market signals to produce a sector-by-sector mood index.

This is the foundation of a full AI-generated Canadian Real Estate Sentiment Index I’m building—think Bloomberg terminal, but for developers, brokers, and CRE nerds.

A trend graph is coming soon. But for now, enjoy the vibes.

Again, Welcome Back…

With all that administration out of the way, now onto the actual talk…

Solopreneurship, Familypreneurship and Partnerships

There's something uniquely draining about trying to build anything substantial on your own.

After decades in development, I've learned that even when you're technically "the boss," going it completely alone creates a special kind of exhaustion that coffee (and Scotch) can't fix.

The partnerships that matter most aren't always the ones in legal documents. They're the realtor who tells you the brutal truth about your product when everyone else is nodding along. The business partner who is always upbeat, constantly smiling and asks you how you are doing as soon as the Google Meet starts. The spouse who listens to your half-baked ideas at the kitchen table, usually trying not to roll their eyes.

These relationships don't just make the work better - they make it bearable. They transform the isolating weight of decision-making into something you can actually shoulder day after day, year after year.

As we navigate challenges like the one below, I'm reminded how grateful I am for the circle of people who help carry the load.

Not employees, not masterminds, not networking contacts - but true partners who are invested in seeing things succeed as much as you are.

Now, let's dive into what happens when a potential partner claims to want your input while their cognitive biases make it impossible for them to actually hear it...

The Open-Minded Builder

SCENE: Thursday morning. I'm standing on a vacant lot with Kal (my business partner), Barry (our local realtor/market expert), and Jake from PrefabPlus (our potential JV builder partner). We're hunched over site plans spread across the hood of Barry's SUV.

"So that's the site," I gesture. "Twenty-eight lots ready for your prefab process. We just need to figure out what to build on them."

Jake adjusts his PrefabPlus hard hat. "Love it. This is exactly why our Integrated Design Process (IDP) is so powerful. We approach each market with a blank slate and let the data guide us."

Kal steps forward. "That's exactly what we're looking for in a partner. Someone who can adapt to what this specific market needs."

"That's why I asked Barry to join us," I add. "Nobody knows buyers in this area better."

Barry smiles. "Been selling here for seventeen years. Sold my first house before they even paved the main road."

Jake's eyes light up. "Perfect! Our IDP thrives on local expertise. We're completely open to letting the market dictate what we build."

What follows is a textbook case of saying one thing while doing another:

Barry: "First thing to understand about this area is basements. They're non-negotiable for families here."

Jake: "Well, actually, our AI analysis shows basements are incredibly inefficient. We've developed specialized storage solutions that render them obsolete."

Barry: "Families here use basements for future bedroom expansion, home offices, play areas during winter—"

Jake: "Our research indicates flex spaces on the main floor are superior."

Barry: "Three bedrooms minimum if you want these to move quickly."

Jake: "Two bedrooms plus a multi-purpose flex space optimizes square footage allocation."

I can't contain myself any longer. "Are you here to learn about the market or justify a hypothesis? Because it sounds like your homes are already designed."

Kal places a calming hand on my shoulder. "What my partner is trying to say is that we're genuinely curious about how your process adapts to local insights."

Jake looks genuinely confused. "We're completely open-minded. We just know customers want sustainability, aesthetically pleasing exteriors, and single-level living—all for $500,000."

Barry: "If you could hit $450,000, you'd sell through these a lot faster."

Jake: "Our cost modeling indicates $500,000 is the optimal price point."

Kal leans in. "Jake, we've been developing in Western Canada for decades. When the local expert says $450,000 is the sweet spot, that's not just an opinion—it's backed by hundreds of transactions in this exact market."

After thirty more minutes of this circular conversation, Barry gives up. "You know what? You're right. The client knows best."

As Barry heads back to his car, I sketch a simple diagram. Kal moves closer, peering over my shoulder. "The matrix?" he asks quietly. I nod.

"Jake, I want to show you something we call the Cognitive Bias-Expertise Matrix," I say, turning my notebook toward him.

"See, there are four types of builders in this world," I explain, pointing to each quadrant.

"Those with high expertise and low cognitive bias succeed because they apply what they know while remaining adaptable. Those with high cognitive bias and low expertise fail because they're convinced they're right with nothing to back it up."

Jake studies the diagram with furrowed brows.

"The dangerous zone," I continue, tapping the upper right quadrant, "is high expertise combined with high cognitive bias. That's where smart people with proven processes become so convinced of their approach that they stop listening.

“They hear what they want to hear and filter everything else out."

"And which quadrant do you think I'm in?" Jake asks, his tone suggesting he already knows the answer.

"Your company has expertise—your track record proves that. But you came here claiming a blank slate while actually carrying a backpack full of cognitive biases. You asked for local market insights but rejected every piece of information that didn't align with your predetermined product."

Jake opens his mouth to object, then closes it, looking back at the diagram.

"Look, prefabrication is brilliant for efficiency," I continue. "But efficiency doesn't matter if you're efficiently building the wrong product for this market. Our potential JV isn't about forcing your proven product into our market—it's about adapting your proven process to create the right product for this specific market."

Kal nods in agreement. "We're not questioning your expertise in building efficiently. That's precisely why we're interested in working with you. But that efficiency needs to be applied to what actually sells here."

"So what are you suggesting?" Jake asks, his defensive posture softening slightly.

"Let's try something radical," I say. "What if we actually listened to Barry? What if we took everything he said at face value for a moment, then applied your efficient methods to deliver exactly what he knows will sell?"

"But our process—"

"Your process should serve the market, not the other way around," I interrupt. "There's a saying in development: 'Build it and they will come' is the most expensive cognitive bias in real estate."

The Lesson

After Jake left (promising to "reconsider" his approach), I couldn't help but wonder: how many of us are walking around with our own version of Jake's blinders?

Ask yourself:

• What product/service am I so convinced about that I might be filtering out contrary evidence?

• When was the last time I genuinely changed my approach based on feedback?

• Which of my "proven processes" might benefit from a market reality check?

Here's a quick bias-detection framework that's saved me from countless expensive mistakes:

1. The Outsider Test: Ask someone completely outside your industry to evaluate your core assumptions

2. The Reverse Scenario: If a competitor did exactly what you're planning, would you think it was brilliant or foolish?

3. The Data Challenge: What evidence would it take to convince you your approach is wrong?

In development, being open-minded isn't just a personality trait—it's a competitive advantage.

Because when it comes down to it, the market doesn't care about your brilliant process or your AI algorithms.

It cares about one thing only: does this product meet my needs at a price I can afford?

Everything else is just noise.

🎯 Your ChatGPT Prompt to Create an Action Figure of Yourself (or your alter ego):

Swap out whatever you want — boots for bourbon, laptop for laser pointer — and see what the AI comes up with.

📊 CRE Sentiment by Sector

Each week, I feed the top Canadian commercial real estate headlines into my AI Sentiment Bot^TM , which analyzes tone, context, and market signals to produce a sector-by-sector mood index.

Week of April 14–18, 2025

🤔 Other Stuff From The Week

Maybe instead of using my AI powers for evil (rendering super hero Greg 🦹 ), I should channel my energy into something more useful, like free 30-second real estate renderings:

Retail:

Residential (older post, but still an interesting site):

Office (this was from 2 years ago):

Office (same prompt as above, but today with Sora in 30 seconds - you decide):

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👉 Facing development challenges that keep you up at night? Whether it's navigating byzantine zoning bylaws, optimizing your pro forma, or finding that perfect strategic positioning in a crowded market, I've seen it all in 30 years in the development trenches.

Here's how I can help:

• Strategy Sessions: One conversation could save you six figures in avoidable mistakes

• Deal Analysis: Get a second set of experienced eyes on your numbers before you commit

• Development Roadmapping: Clear, actionable plans that anticipate the potholes ahead

• Stakeholder Navigation: Learn how to speak the language of planners, politicians, and partners

Don't waste time reinventing the wheel. Every month you spend figuring things out on your own is another month of carrying costs eating into your returns.

Hit reply with "DEVELOPMENT 911" and we'll set up a quick call to discuss your specific challenges. No obligation, no sales pitch – just straight talk about your project and how I might be able to help.

Alternatively, reply with your biggest current development headache and I'll send you my quick-take perspective at no charge.

See you next Friday.

Cheers,

- Greg

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