How to actually do business across the Canada-USA border

Marc Palud · 2026-09-17 · Winnipeg

There are places where you can stand in one country and see the other one across the water. Windsor and Detroit. Fort Erie and Buffalo. Vancouver and Blaine. The distance is nothing. You can walk it.

And yet most Canadian business owners I meet have no working relationships in the United States, and most American business owners have none in Canada. Not because anyone decided against it. Because nobody introduced them.

That is the whole thing. It is not distance, it is not language, it is not even paperwork. It is that you do not know anyone on the other side, and nobody on the other side knows you.

The border that is real, and the one that is not

Let me be clear about which problems are actually problems.

The time zones are not a problem. Toronto and Chicago share a working day. Vancouver and Seattle are in the same zone. You can get someone on the phone this afternoon.

The culture is not a problem either, or not the way people imagine. Yes, Canadians tend to be a little more reserved and Americans tend to get to the point faster. You adjust in one conversation. Nobody has ever lost a deal over that.

Even the practical side, the customs paperwork, the tax questions, the incorporation, is a solved problem. There are accountants and lawyers who do nothing else. You hire one. It costs money and it takes time and then it is done.

Here is what is not solved. You send a message to someone in Columbus or Calgary, and they have no way of knowing whether you are real. No mutual contact. No shared room. No one they can ask. Your message is not unwelcome, it is simply unverifiable, and unverifiable messages go nowhere.

That is the border that matters, and it is the only one nobody sells you a service for.

Two groups, one corridor

The Canada-USA corridor is not one audience. It is two, and I think the second is the more interesting one.

The first is obvious. Canadian companies that want customers, partners or distribution in the States. American companies that want the same going north. Professional firms on both sides with clients who have interests at the other end. These two economies are wound around each other more tightly than almost any other pair on earth, and almost none of that started with a form. It started with somebody knowing somebody.

The second group is the one I keep running into. Canadians who used to work in the US, Americans who used to live in Canada, people who have family, a degree, a former employer or half a career on the other side. They already understand both rooms. What they do not have is a network that spans the two, so the two halves of their working life never introduce themselves to each other.

If that is you, you are not starting from zero. You are starting from something better than most people have and simply not using it.

Why the usual advice does not survive the crossing

The standard networking advice does not travel well, and across a border it produces almost nothing.

More connection requests does not work, because a connection request is not a relationship. Neither is a follow. Neither is a comment.

Conferences work better, because three days in a room compresses a year of contact. But they are expensive, they happen occasionally, and what you build there quietly decays over the eleven months in between unless something holds it together.

Lists and databases give you volume with no trust attached, and volume is not what is missing. If more names were the answer, you would already have it solved.

I have spent years running rooms where people actually meet each other, and the thing that works is never the volume. It is who vouches for whom.

What actually works

One person on the other side who knows you, and who knows the person you should meet, saying so out loud to both of you.

That is it. That is the mechanism, and everyone reading this has benefited from it already, probably without noticing. Your best client came from somewhere. Your best hire was somebody's friend. The supplier who saved you was mentioned by someone you trusted.

A warm introduction works because it lends you something you cannot manufacture. It borrows an existing relationship. When somebody an American already trusts says "you should talk to this person in Toronto", the question of whether you are real has already been answered, before you say a word.

The most valuable thing in business is not a list. It is the small number of people who would take your call on a bad day, and the smaller number still who would put their own name next to yours in front of somebody else. That is not a nice sentiment, it is the most reliable commercial mechanism there is, and it has worked for a very long time.

Those relationships nearly always start as business and quietly turn into friendships, and the friendship is the part that makes them last. A contact passes on your details. A friend picks up the phone and says, you two need to talk. That is the difference between a year of effort and an afternoon.

The difficulty across a border has never been that introductions do not work. It is that most people do not have anybody on the other side willing to make one.

How the Bridge is built

The Canada-USA Business Bridge Collaboration Group exists to put somebody on both ends.

Two co-leads, one on each side. Most business communities have one organiser in one city. A bridge needs a named human at each end, because an introduction is only ever as good as the person making it, and that person has to actually know the local room. I hold the Canadian end. The American end is being founded now, and we are choosing the person who will hold it.

Introductions are made by a human who knows both people. Somebody asks for a particular kind of introduction, a co-lead who knows both sides weighs whether it actually makes sense, and then makes it properly, in their own words, to both people at once. If it does not make sense, it does not happen. The judgement is the point.

No bots, no scraped lists, no cold outreach. Members are not a database to be sold to. The whole thing depends on the room staying worth being in, which means nobody is pitched the moment they arrive.

Your own trusted network travels with you. Every member keeps their own profile and their own circle of trusted connections, so what you build does not evaporate when an event ends.

It meets in both directions. Online across the border, and in person on each side as the local rooms grow. The method is the one behind Speed Networking Live: structured, fast, and built so that people leave having actually met somebody.

Who this is for

You run a business in Canada and the United States is the obvious next market, and you would rather walk in through someone than cold.

You run a business in the United States and you have been meaning to look north for two years.

You have history on both sides, and you are tired of having two separate professional lives that never speak to each other.

You are not looking for leads. You are looking for the two or three people, across the border, who would change your year.

And one seat, for the right American

A bridge needs somebody standing on both banks. I am looking for a co-lead in the United States: a well connected entrepreneur or business owner who can help anchor and grow the American side of this.

For whoever takes it, there is something genuinely interesting on offer. You help shape who and what crosses the bridge. You get early access to a whole set of relationships, ideas and collaborations that would otherwise never have come past you.

The Canadian side is built. The structure is built. The person who takes the American end shapes their half from the first member onward.

So I will ask it the way I have been asking it. Would you be open to exploring the idea, or does somebody immediately come to mind who would be a natural fit for this?

It is part of the My Most Trusted network, which has 89,529 people in its Trusted Universe as of September 2026, so an introduction that starts here does not have to stop here.