I’ve been on a mission since getting back from Italy.
The espresso mission. Some of you have heard about this already.
Four or five espressos a day in Calabria. Each one better than the last. Since landing back in Windsor, I’ve been systematically working through every variable — grind size, water temperature, pressure, tamp — trying to close the gap between what I was drinking in Italy and what I’m producing at home.
I was recently complaining to my wife that the one variable I hadn’t yet addressed was the cup itself. The cup, I was fairly confident, might be what’s been holding me back.
My kids were apparently listening.
Last week they went to Crock A Doodle — unprompted, entirely their own idea — and made me a new espresso cup.
It is the most thoughtful gift I have received in a long time. It is also a pretty clear sign that my espresso obsession has reached a level that is noticeable to people who live with me.
The cup is beautiful. The espresso is getting closer.
I want to talk about something that doesn’t get nearly enough attention — and it’s sitting right in front of us.
Over the next decade, more than $2 trillion worth of Canadian businesses are expected to change hands. Baby boomer business owners are approaching retirement. The largest business succession wave in Canadian history is already underway.
And almost nobody is ready for it.
I hear it from both sides constantly.
Younger entrepreneurs — ambitious, capable, looking to buy — tell me all the time:
“Let me know if you hear of anything good for sale.”
They’ve heard the wave is coming. They know the opportunity is out there. But they can’t find it.
Because most businesses don’t get listed the way a house does. There’s no MLS for a 40-year-old manufacturing company or a family-owned greenhouse operation. The deals happen through relationships, through networks, through someone knowing someone.
If you’re not plugged into the right rooms, you can spend years waiting for an opportunity that never finds you.
For entrepreneurs looking to purchase an established business in Windsor, Essex County or Southwestern Ontario, financing may involve more than the purchase price. The transaction may also require financing for the commercial property, renovations, equipment, working capital or existing business debt.
On the other side, I talk to business owners who genuinely want to sell — or at least say they do.
But they don’t know what their business is actually worth. They’re not sure they’re emotionally ready. They’re worried about who they’d sell to and what that person would do to something they spent decades building.
And because there’s no deadline forcing the decision — they delay. They kick the can. They’ll figure it out next year.
The problem is that selling a business is not like calling your realtor and saying, “List it please.”
It requires preparation that most owners haven’t started. And when something forces the timeline — a health event, a family situation, a market shift — the lack of preparation becomes very expensive very fast.
Business owners in Windsor-Essex who are considering retirement or succession should begin planning well before putting the business on the market. Understanding the value of the business, the property and the financing structure can make the eventual transition smoother.
I know this from the inside.
UCC Mortgage Co. is a 50-plus-year-old business. I purchased it in 2022.
The way it happened was about as informal as it gets — the previous owner wanted to sell, I wanted to buy something, and we found each other through a mutual connection. No formal process. No listing. Just two people who happened to be in the right conversation at the right time.
By every measure, it worked out well. Both sides are happy with how it played out.
But I think about how easily it could have gone the other way. What if that conversation never happened? What if the financing couldn’t be structured in a way that worked for both sides?
The successful ones are rarely the result of a perfect process. They’re the result of the right people finding each other at the right time — with the right team around them to make it work.
Here’s the part that doesn’t get talked about enough.
I’ve watched people sell their businesses — good deals, fair prices, clean transactions — and still end up in a difficult place six months later.
Not because the deal was wrong. Because they hadn’t planned for what came after.
Some feel financially unsettled despite a significant payout — because the steady income they’d built their life around is suddenly gone.
Some get bored in a way they didn’t anticipate — because their identity was more tied to the business than they realized.
And some jump into something new too quickly, sinking money into a venture that doesn’t come close to replicating what they had.
The exit is one decision. What comes after is everything.
At UCC Mortgage Co., we help business owners and entrepreneurs explore customized financing solutions for business acquisitions, commercial properties, refinancing, construction and other complex transactions.
Depending on the situation, financing may be available through institutional or private lenders. The right structure will depend on the business, the property, the borrower’s financial position and the overall transaction.
If you’re a business owner thinking about selling — even loosely, even “someday” — the time to start is long before you’re ready to act.
And if you’re a buyer looking for the right opportunity in Windsor-Essex or Southwestern Ontario, it starts with being in the right rooms and the right conversations. Not waiting for something to appear on a website.
The deal itself is only one piece of it. Getting there — and what comes after — is where most people need the most help.
If you are looking to buy a business, sell a business or plan for a future transition in Windsor-Essex, speaking with a mortgage professional early can help you understand your financing options before a time-sensitive opportunity arises.
Until next week,
Vince
P.S. The espresso this morning was excellent. I’m giving the cup partial credit.
