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

Glen Sutherland

Helping anyone invest in the U.S. real estate market from anywhere!

  1. EP423 How to Protect Your Real Estate Portfolio from Taxes and Probate Fees with Mark Halpern

    4d ago

    EP423 How to Protect Your Real Estate Portfolio from Taxes and Probate Fees with Mark Halpern

    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

    25 min
  2. EP422 How to Reduce Your Taxes on a Rental Property in the USA with Tim Miron

    May 28

    EP422 How to Reduce Your Taxes on a Rental Property in the USA with Tim Miron

    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.

    15 min
  3. EP420 How a Canadian Investor Built Wealth in Belize Real Estate with Shawn Rea

    May 14

    EP420 How a Canadian Investor Built Wealth in Belize Real Estate with Shawn Rea

    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.

    25 min
  4. EP421 Avoid These Mistakes That Kill Real Estate Deals with Christopher Lento

    May 12

    EP421 Avoid These Mistakes That Kill Real Estate Deals with Christopher Lento

    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.

    33 min
  5. EP419 How Canadians Can Wholesale & Flip Houses in the USA Remotely with Jagger Babuin

    May 7

    EP419 How Canadians Can Wholesale & Flip Houses in the USA Remotely with Jagger Babuin

    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.

    43 min
  6. EP418 Bank Failures, Callable Loans & Real Estate Risk Explained with David Morgan

    Apr 30

    EP418 Bank Failures, Callable Loans & Real Estate Risk Explained with David Morgan

    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.

    26 min
  7. EP417 Best Non-Food Franchises for Real Estate Investors with Jon Ostenson

    Apr 22

    EP417 Best Non-Food Franchises for Real Estate Investors with Jon Ostenson

    In this episode of Canadian Investing in the US, Glen Sutherland interviews franchise consultant Jon Ostenson to explore how franchising can be a powerful wealth-building strategy — especially for real estate investors and Canadians looking to expand into the U.S. market. John shares how he transitioned from the corporate world to franchising, became President of ShelfGenie, and now helps investors identify non-food franchise opportunities across North America. The conversation breaks down common misconceptions about franchising, the benefits of leveraging established systems, and why “non-sexy” service businesses (like paving, line striping, and mobility retrofitting) can often outperform trendier ventures. Glen and John also discuss how franchising can complement real estate portfolios, provide alternative income streams during high interest rate cycles, and even serve as a pathway for E-2 visa applicants. They dive into semi-passive ownership models, the importance of hiring strong general managers, and why niche home service businesses are attracting high-level professionals — including physicians and Harvard MBAs. Whether you’re looking to diversify beyond rental properties, create a vertically integrated service business, or explore U.S. residency options, this episode opens the door to opportunities most investors never consider.

    22 min
  8. EP416 How a Canadian Investor Flipped a Detroit Property for Profit with Ruslan Benco

    Apr 15

    EP416 How a Canadian Investor Flipped a Detroit Property for Profit with Ruslan Benco

    In this episode of Canadian Investing in the U.S., Glen Sutherland interviews Ruslan Benko, a Canadian investor who transitioned from buying duplexes in Ontario and Alberta to scaling his portfolio in the United States. Ruslan explains how rising Canadian property prices and stagnant rents pushed him to seek better cash flow and scalability opportunities south of the border. After discovering asset-based lending options like DSCR loans, he completed his first U.S. deal—a Detroit flip purchased for $75,000, renovated, and sold for a solid profit within just a few months. The conversation dives into lessons learned from that first deal, including managing contractors remotely, refining renovation strategies for flips versus rentals, and overcoming unexpected challenges like property break-ins. Ruslan also shares his current project in Dallas, where he’s executing a garage conversion to increase property value and expand exit strategies. Throughout the episode, he emphasizes the importance of building a strong local team, maintaining flexibility with multiple investment exits, and taking action while learning from experienced investors—highlighting a clear path for Canadians looking to scale into the U.S. market.

    22 min
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Helping anyone invest in the U.S. real estate market from anywhere!

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