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Glen Sutherland started out investing in his own backyard in Cambridge, Ontario, but eventually made the leap south, building a portfolio across Alabama, Missouri, Indiana, Ohio, Florida, Michigan and Texas.
In this episode of Where Should I Invest?, hosts Sarah Larbi and Ryan Sweda sit down with Glen to unpack what it actually takes for a Canadian to build and scale a US real estate business, from visas to financing to picking the right market.
“The greatest thing in the world is to get paid in US dollars over Canadian dollars.”
Glen Sutherland, US Real Estate Investor and Host of A Canadian Investing in the US
What We Cover
- Glen’s path from single-family houses in Ontario to a multi-state US portfolio, and why he eventually stopped self-managing.
- The E-2 visa explained: what counts as an active versus passive business, why real estate holdings no longer count toward the investment requirement, and the employee criteria most applicants need to meet.
- How Glen is using AI and virtual assistants to reduce reliance on W-2 employees, and where he still sees a role for on-site labour.
- Alternative ways to break into US investing with limited capital, including franchises, self-storage, and seller-financed mobile home parks.
- Why eviction laws, rent increase rules, and landlord-tenant regulations vary so much by state, and how that shapes where Glen chooses to invest.
- The real difference between 30-year US mortgages and Canadian renewal cycles, and why that matters for long-term planning.
- Cash flow versus appreciation, and why Glen prioritizes forcing appreciation through renovation rather than betting on market timing.
- A creative deal structure most investors overlook: buying an off-market duplex in a single-family neighbourhood, then converting it back to a single-family home to solve a comps problem.
- Why due diligence on comps, crime maps, and school zones matters more than chasing a specific city.
This episode has been brought to you in part by:
Ryan Carson, Carson Law – https://www.carsonlaw.ca/ or email ryan@carsonlaw.ca
Matt Pickering, National Bank matthew.pickering@nbc.ca
Connect with Glen Sutherland
Podcast: https://www.youtube.com/@acanadianinvestingintheusa
Website: https://acanadianinvestingintheusa.com/coaching
E-mail: glen@glensutherland.com
Free Facebook Group: https://www.facebook.com/groups/canadianinvestingintheusa
Disclaimer: The information shared in this episode and content is for educational and informational purposes only and should not be considered professional financial, legal, or investment advice.
