Episode 496: From Canada to U.S. Real Estate: How to Invest Across Borders Successfully with Glen Sutherland

Ever wondered how to break into U.S. real estate investing—even if you’re based in another country? This week, I sit down with Glen Sutherland, a Canadian investor who successfully scaled his real estate business by expanding into the U.S. Glen shares the advantages of investing across borders, including access to creative financing strategies, long-term mortgages, and public data that makes deal sourcing easier.

 

We dive into the step-by-step process of setting up a remote investing operation, from choosing the right markets to building a reliable team on the ground. Glen also shares key insights on structuring deals, financing options, and the biggest mistakes international investors make when entering the U.S. market. If you’ve ever considered investing outside your home country, this episode is packed with actionable insights to help you get started.

 

Episode Highlights

[0:00] – Introduction

[2:00] – How Glen transitioned from investing in Canada to the U.S.

[4:05] – The biggest advantages of investing in the U.S. market

[7:18] – How to build and manage a real estate team remotely

[10:09] – Creative financing strategies: sub-to deals, seller financing, and lease options

[12:32] – The importance of having multiple contractors and property managers

[15:33] – Generating leads through property managers, contractors, and attorneys

[17:05] – Common tax and legal pitfalls for Canadians investing in the U.S.

[20:50] – How Glen helps others break into U.S. real estate investing

[23:10] – Understanding corporate structures for tax efficiency

[25:35] – Why 30-year mortgages in the U.S. offer more stability than Canada’s system

[27:00] – The role of public data access in making informed investment decisions

 

Key Takeaways

1. U.S. real estate offers more creative financing opportunities – Investors can leverage strategies like subject-to deals, seller financing, and lease options, which are harder to execute in Canada due to regulations.

2. Building a strong remote team is crucial – Success in out-of-state or international investing depends on hiring reliable contractors, property managers, and local experts to manage properties effectively.

3. Understanding tax structures can save investors thousands – Canadian investors need to structure their U.S. investments properly to avoid double taxation and optimize for cross-border tax benefits.

4. Having access to public data gives U.S. investors a competitive edge – Unlike Canada, the U.S. provides easy access to property sales history, ownership details, and mortgage information, making it easier to analyze deals.

5. Long-term fixed-rate mortgages provide stability – The U.S. mortgage system allows for 30-year fixed loans, which help investors predict cash flow and avoid financial uncertainty when interest rates change.