Two weeks ago fifteen of us went to Italy together.
My wife and kids, my parents, my brother and sister and their spouses and kids. Ranging in age from 4 to 74. My brother and sister planned the whole thing — I just showed up and tried not to get in the way.
We flew into Rome first. And something was slightly off — my dad seemed out of his element. Like a tourist, which he never is. Rome is beautiful but it wasn’t his Italy.
That changed the moment we got to Calabria.
The second we landed something shifted in him. You could see it. And as we walked out of the airport to pick up our rental cars, he looked around at all fifteen of us and said:
“I left here as 1. And now I’ve returned as 15.”
I don’t think anyone said anything for a moment.
Now — I need to be honest about my priorities when I travel. Especially to Italy. The food and drink come first. Everything else is a bonus.
Calabria delivered on every level. Every meal felt like a Sunday afternoon at my nonna’s. The people were kind. The pace was slow. But the coffee and the gelato — I am genuinely nervous to tally what we spent on those two items alone. Not because it was expensive — coffee and gelato in Italy are dirt cheap compared to home. But we consumed an absolutely absurd amount. Zero regrets.
The espresso in particular has broken me. Since landing back in Windsor I have spent an embarrassing number of hours with ChatGPT trying to recalibrate my espresso machine to match what I was drinking in Calabria. Progress has been made. I am not there yet. I will not stop.
The current residents of my dad’s childhood home — a humble place in a small village where not many people live anymore — let fifteen of us tour it and take pictures out front. Couldn’t have been more gracious.
If you ever get the chance to visit Calabria — the Tropea area specifically — go. It is the most authentic, unhurried, genuinely beautiful part of Italy I have ever experienced. Officially my favourite place I’ve ever been. And it’s not close.
I keep thinking about the window that made this trip possible. Everyone old enough to travel, young enough to enjoy it, grandparents still able to make it, grandkids old enough to remember it. That window doesn’t stay open forever. I’m grateful we climbed through it when we did.
I came back to a full pipeline and hit the ground running — which is a good problem to have.
But something I’ve been watching closely over the past several months, and it became even clearer when I returned, is that not everyone is experiencing the same market right now.
Our commercial real estate business is strong. Genuinely strong. We’re seeing owner-occupied spaces being purchased and built, commercial and mixed-use plazas being bought, sold and constructed, industrial and warehouse activity picking up. The clients doing these deals aren’t waiting for the news to tell them it’s time. They’re already moving.
Our residential mortgage business and private lending activity tell a different story. Quieter. Still recovering.
Two books of business. Same company. Two completely different realities.
This is the K-shaped economy playing out in real time — and I think most people don’t realize it’s happening around them.
On the residential side, there’s less room to manoeuvre. A first time buyer either has the down payment or they don’t. They either earn enough to service the mortgage or they don’t. Someone who bought at the top of the market and is now underwater doesn’t have many options. The math is what it is.
Commercial deals are different. There’s room for creativity — a vendor takeback from the seller, value created through better leases, structures that can be shaped to make a deal work. The people doing these deals aren’t necessarily richer. But they’re in the loop. They have access to the right conversations, the right advisors, the right information. And they’re moving while others are waiting.
Here’s the harder truth — and I say this not to be bleak but because I think it’s worth naming honestly.
The middle class is shrinking. We are quietly moving toward a world of haves and have nots. And I believe the single biggest differentiator between the two is ownership of good quality, scarce assets.
Real estate — despite where we are in the local cycle right now — is one of those assets. It will increase in value over time, measured in dollars. It always has. The question is never really whether to own it. The question is when.
And sometimes the best time to buy is when nobody else is.
Because once everybody catches on — once it’s on the news, once your neighbour is talking about it, once it feels obvious — you run the risk of being late to the party.
The people I watch moving right now aren’t doing it because they’re certain about what happens next. They’re doing it because they understand that waiting for certainty is its own kind of risk.
Those windows don’t stay open forever either.
Until next week,
Vince
P.S. Still working on the espresso. ChatGPT is doing its best. So am I. Some things you just have to experience in Calabria to truly understand.
