Introduction
When I started my real estate investing venture with my business partner, the plan was ambitious: focus 80% of the business on the U.S. and 20% on Canada. The U.S. looked like a bigger market with more potential, but I didn’t want to ignore my backyard. In Canada, I had proximity, expertise, and a trusted network.
It sounded smart to build for both markets. But in hindsight, we over-structured things up front to be fully by the book, when we could have started more scrappy—and that’s the lesson I wish I had known earlier.
How I Structured the Business
I did what many entrepreneurs do: built for scale before testing. I set up a holding company, a Canadian operating company, and an operating company, but for tax reasons, we needed to set it up as a partnership, which meant two more companies—a GP and an LP. On paper, it gave me legal protection and flexibility.
But in practice? It added complexity, costs, and compliance before I had real traction.
Shifting Focus Back to Canada
Within months, it became clear that deals in Canada were easier to secure. We had the local know-how, and opportunities moved faster here. The U.S. entities, meanwhile, were underutilized. Filing requirements, tax reporting, and overhead piled up—even though the returns weren’t there.
Instead of creating leverage, the U.S. structure became a burden.
What I Would Do Differently
If I had to start over, I’d keep things simple. One holding company and one Canadian operating company was more than enough to get moving. For the U.S., I should have partnered with someone already on the ground. Acting as a contractor or consultant through my Canadian company would have been imperfect, but it would have let me test the market quickly without sinking money into unnecessary legal entities. Then, when the US was proven, I could have setup the other entities.
The truth is, structure should follow success—not come before it.
Key Takeaway
In real estate investing, it’s tempting to set everything up “the right way” from day one. But that can slow you down and drain resources. Be scrappy. Test the waters. When the opportunity proves itself, then add structure. Startups don’t win by being over-engineered—they win by learning fast.
