A Canadian Investing in the U.S. with Glen Sutherland

In this episode of Canadian Investing in the USA, Glen Sutherland sits down with digital marketing expert and AIS Media founder, Thomas Harpointner, to discuss one of the biggest shifts happening online today: the rise of AI-powered search. Thomas explains how tools like Google Gemini, ChatGPT, and other AI platforms are changing the way consumers find information and how businesses attract customers. While many companies are seeing website traffic decline as AI provides answers directly within search results, Thomas reveals why this isn't necessarily bad news. In many cases, businesses are receiving fewer but far more qualified leads because AI is helping educate prospects before they ever visit a website. The conversation dives into practical strategies for ensuring your business remains visible in an AI-driven world. Thomas shares why content is still king, how authority and credibility influence AI recommendations, and why podcasts, videos, blogs, social media, and industry publications all play a role in building digital authority. He also discusses the importance of structured content, SEO fundamentals, thought leadership, and understanding what your ideal customer is actually searching for rather than relying on assumptions. For business owners, investors, and entrepreneurs looking to stay relevant as AI reshapes online discovery, this episode offers valuable insights into how to position yourself as a trusted authority that AI platforms will reference and recommend.

Brad Beauchamp, a Canadian mortgage broker based between Vaughan and West Palm Beach, joins Glen Sutherland to explain how Canadians can finance U.S. real estate investments using DSCR loans and cross-border lending strategies. Brad shares his own immigration journey from obtaining an L1 executive visa to eventually becoming a U.S. citizen, before diving into the opportunities available for Canadian investors south of the border. The conversation highlights how DSCR (Debt Service Coverage Ratio) loans allow investors to qualify based primarily on a property’s cash flow instead of personal income or employment verification, making it easier for Canadians to scale portfolios in markets like Florida, Ohio, Texas, and Alabama. Brad explains that while Canadians can secure financing without U.S. credit history, investors with U.S. tax IDs, entities, residency ties, or established FICO scores can often access lower rates and better leverage. The episode also focuses heavily on structuring and protecting investments properly when buying U.S. real estate. Brad and Glen discuss the importance of setting up U.S. LLCs, understanding cross-border taxation, using professional advisors, and avoiding common mistakes such as holding properties personally instead of through entities. They explain hidden costs Canadians often overlook — including underwriting fees, loan origination fees, title fees, prepayment penalties, and refinancing costs — while emphasizing that proper planning can save investors significant money long term. The discussion covers partnerships with Americans, refinancing strategies, seasoning periods, and how the larger U.S. market creates more financing flexibility and opportunity than Canada. Overall, the interview serves as a practical guide for Canadians who want to leverage U.S. financing, build cash-flowing portfolios, and avoid costly structural and lending mistakes. Find out what type of US real estate investment would fit you best at: https://acanadianinvestingintheusa.com/QUIZ

Benny Delaney shares his journey from growing up in India, building a business and investing in ultra-expensive real estate in Hong Kong, and eventually immigrating to Canada in 2017 for his children’s future. After buying duplexes in Oshawa and Peterborough, Benny discovered U.S. real estate investing through Glen Sutherland’s coaching and became attracted to the flexibility of DSCR loans in the United States. Unlike Canadian lenders that focused heavily on proving employment income, Benny found that U.S. lenders cared more about the property’s cash flow potential. This allowed him to scale into properties in Florida and Detroit despite being semi-retired and no longer operating an active business. The interview also dives deeply into Benny’s strategy of remotely managing student rentals in Florida from Toronto. He explains how building a reliable local team — including realtors, plumbers, HVAC contractors, cleaners, and leasing support — made remote investing practical. Benny discusses handling student tenants, lease-ups, payment systems, maintenance requests, and tenant screening while emphasizing that real estate investing is ultimately a business built around problem-solving. The conversation highlights the difference between investing for appreciation versus investing for cash flow, with Benny prioritizing higher-income properties like student rentals and Airbnbs to support his semi-retired lifestyle. The episode offers valuable insight for Canadians looking to invest remotely in U.S. markets while leveraging creative financing and higher cash-flow opportunities unavailable in many Canadian cities. What type of Investor are you? Take the Quiz? https://acanadianinvestingintheusa.com/quiz

In this episode of Canadian Investing in the US, Glen Sutherland sits down with estate planning expert Mark Halpern to unpack the critical importance of proactive estate planning for investors and families. Mark shares personal insights that shaped his career and emphasizes the dangers of failing to plan—highlighting how something as simple as not having a will can create financial hardship and unnecessary stress for loved ones. The conversation explores foundational elements like wills, powers of attorney, and the risks of dying intestate, especially for Canadians with families and real estate holdings. The discussion goes deeper into advanced strategies, including probate tax minimization, multiple wills, and the strategic use of tax-exempt life insurance to preserve wealth and cover future tax liabilities. Mark also introduces the concept of an “estate directory” to ensure loved ones can easily access critical information in emergencies. Together, Glen and Mark emphasize that successful investing isn’t just about building wealth—it’s about protecting it, transferring it efficiently, and avoiding costly mistakes through proper planning and the right professional team. What US real estate strategy would work best for you? https://acanadianinvestingintheusa.com/QUIZ

In this episode of Canadian Investing in the US, host Glen Sutherland welcomes recurring guest and CPA Tim Miron of Pursuit CPA to discuss strategies Canadian investors can use to reduce taxes on U.S. rental properties. Tim explains the difference between passive and active income taxation, noting that rental income earned inside a corporation can be taxed at rates approaching 50%, while active business income in a Canadian corporation may be taxed as low as 12% in Ontario. The conversation focuses on a strategy where a Canadian corporation acts as a property management company for U.S. rental properties, charging management fees to the U.S. entity and converting part of the rental income into lower-taxed active income. Tim emphasizes the importance of charging realistic management fees, maintaining proper invoicing, and ensuring the arrangement reflects legitimate property management activity. Glen and Tim also discuss practical considerations such as bookkeeping complexity, moving money consistently between entities, and how these strategies change depending on whether investors are holding stabilized rentals, actively renovating properties, or operating other active businesses. Tim explains that rehab projects may justify significantly higher management fees due to the increased workload, while investors already generating active business income through flipping or property management may have alternative tax planning options available. Throughout the episode, the two stress the importance of proper structuring and working with experienced cross-border tax professionals to ensure compliance and maximize tax efficiency for Canadian investors operating in the U.S. real estate market.

In this episode, Glen reconnects with returning guest Shawn Rea to explore his real estate journey since relocating from Canada to Belize. Shawn shares how his initial strategy of buying single parcels of land evolved into a long-term land banking approach after experiencing significant appreciation, with some lots increasing from roughly $15,000 to as much as $75,000 USD. He also experimented with Airbnb condos but found land investments to be more profitable overall. Through negotiation skills, local networking, and strategic acquisitions—including deeply discounted houses and multiple properties—Shawn built a diversified Belize portfolio focused on appreciation and selective cash flow opportunities. The conversation highlights Shawn’s shift toward large-scale development, including completing his first subdivision project after 2.5 years of work, now partially sold and offering entry-level investment opportunities. He discusses the importance of aligning investment strategy with lifestyle goals, navigating financing options as a foreign investor, and building strong local connections in a market without a centralized MLS. The episode provides practical insights into international investing, development timelines, negotiation tactics, and balancing lifestyle design with long-term wealth creation through global real estate opportunities.

In this episode of Canadian Investing in the US, Glen Sutherland interviews Chris Lento, a full-time real estate investor and operator of EM Capital Group, who focuses on acquiring and managing multifamily properties in the U.S. Southeast. Chris shares his journey from starting with small “three-decker” properties in Boston to scaling into large 100+ unit apartment complexes. He emphasizes how early hands-on experience with tenant management and maintenance provided a strong foundation for understanding costs, operations, and decision-making at scale, even though larger properties require teams, systems, and professional management structures. The conversation highlights the importance of systems, processes, and strong property management when scaling a real estate portfolio. Chris explains how his business uses structured acquisition criteria, standardized operating procedures, and tools like project management software to streamline operations and decision-making. A major focus is placed on selecting and managing property managers, including identifying red flags, asking detailed operational questions, and acting quickly when issues arise. He also discusses his current role in sourcing deals, raising capital, and overseeing asset management, while noting that despite recent market slowdowns, improving deal conditions and more realistic pricing are creating new opportunities for investors.

In this episode of Canadian Investing in the US, host Glen Sutherland sits down with real estate entrepreneur Jagger Bablin to discuss the realities of wholesaling, wholetailing, flipping, and creative financing in today’s shifting U.S. real estate market. Originally from British Columbia and now living in Medellín, Colombia, Jagger shares how he built a fully remote real estate business operating across multiple U.S. states while managing teams around the world. The conversation dives deep into direct-to-seller lead generation, how market conditions have forced investors to pivot strategies, and why understanding deal structure is more important than ever. Glen and Jagger also unpack the challenges Canadians face when investing in U.S. real estate, including financing hurdles, corporate structuring mistakes, contractor management, and remote property operations. They share real-world stories about squatters, problematic contractors, property management failures, and the lessons learned from costly mistakes. The episode is packed with practical insights on underwriting conservatively, building systems, leveraging creative financing strategies like subject-to and seller financing, and why mentorship can dramatically shorten the learning curve for new investors entering the U.S. market.

In this episode of Canadian Investing in the US, host Glen Sutherland sits down with financial expert David Morgan to explore the growing risks within the global financial system and what it means for everyday investors. Drawing on over four decades of experience, Morgan outlines how excessive debt, currency devaluation, and structural weaknesses in the banking system could lead to significant economic disruption. He explains the concept of callable loans, potential bank failures, and the fragility of trust in financial institutions—emphasizing that even insured systems may not be as secure as people assume. The conversation then shifts to practical strategies for protecting wealth in uncertain times. Morgan advocates for reducing personal debt, living within one’s means, and gradually building savings in hard assets like gold and silver outside the traditional banking system. He also highlights the importance of understanding financial contracts and preparing for worst-case scenarios without succumbing to fear. For real estate investors, the episode offers a unique lens on leverage, risk management, and financial resilience—encouraging listeners to think critically about how the broader economic system impacts their investment strategies.