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How I Built $1M in U.S. Real Estate as a Canadian Investor In this episode, Glenn Sutherland, a Canadian real estate investor specializing in U.S. multifamily properties, breaks down his journey, lessons learned, and the strategies that helped him scale across borders. Glenn explains why many Canadians are turning to the U.S. market, the value of hiring the right coaches, and how poor property management can make—or break—an investment. This conversation also explores current multifamily trends, the impact of rising interest rates, and how AI and technology are transforming property management. Glenn shares the red flags investors must watch for, the importance of thorough planning, and his long-term vision for leveraging automation to grow his portfolio. Whether you're a Canadian investor, a multifamily operator, or someone interested in tech-driven real estate, this episode delivers actionable insights, practical strategies, and future-focused perspectives. Takeaways The U.S. market provides strong opportunities for Canadian real estate investors. Hiring a coach can accelerate your investment knowledge and avoid costly mistakes. Closing a deal brings a deep sense of reward after months of preparation. Planning, due diligence, and quality checks are essential in real estate. Poor property management can lead to major financial setbacks. Identifying deal breakers early can save investors from bad investments. Higher interest rates are reshaping the multifamily industry. AI and automation are improving property management efficiency. Technology allows investors to focus on strategic decisions instead of daily operations. The future of real estate management is heavily influenced by AI and digital tools. Chapters 00:00 – Introduction to Canadian Real Estate Investment 00:52 – The Journey into Multifamily Real Estate 02:46 – Best and Worst Days in Real Estate 05:15 – Challenges with Property Management 08:10 – Identifying Deal Breakers in Real Estate 09:58 – Current Trends in the Multifamily Industry 12:48 – The Role of Technology in Real Estate 14:43 – Future Vision: AI in Real Estate Management Canadian real estate investor, U.S. multifamily investing, cross-border real estate, property management challenges, investment strategy tips, multifamily market trends, real estate automation, AI in property management, U.S. real estate for Canadians, real estate red flags, multifamily investing strategies, technology in real estate, Glenn Sutherland interview, real estate podcast 2025 #propertyinvestment #canadianinvesting #multifamily #propertymanagement #technology #ai #investmentstrategy #dealbreakers #markettrends #propertymanagementsystem