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

    4H AGO

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

    20H AGO

    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
  3. 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
  4. 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
  5. 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
  6. EP415 Avoid Costly CRA Penalties with These U.S. Tax Filing Rules with Tim Miron

    APR 9

    EP415 Avoid Costly CRA Penalties with These U.S. Tax Filing Rules with Tim Miron

    In this episode of Canadian Investing in the US, Glen Sutherland sits down with returning guest Tim Miron, a CPA specializing in cross-border taxation, to uncover two commonly overlooked filing requirements for Canadians investing in U.S. real estate. They break down the importance of filing the T1134 and T1135 forms—often referred to as “Big Brother forms”—which are required to disclose foreign entities and assets to the Canada Revenue Agency (CRA). While these forms don’t typically result in additional taxes, failing to file them can lead to significant penalties, making awareness critical for investors operating across borders. The conversation highlights how easily investors can fall into non-compliance, especially when setting up U.S. entities, holding foreign bank accounts, or crossing the $100,000 threshold in foreign investments. Tim explains how the CRA’s Voluntary Disclosure Program can help investors correct past mistakes and potentially avoid penalties if they act before being contacted by the government. The episode emphasizes the value of working with experienced professionals to ensure compliance, avoid costly errors, and properly structure cross-border investments from the start.

    18 min
  7. EP414 Passive Income Isn’t Passive: The Systems Behind Financial Freedom with Russ Morgan

    APR 1

    EP414 Passive Income Isn’t Passive: The Systems Behind Financial Freedom with Russ Morgan

    In this episode of Canadian Investing in the US, Glen Sutherland interviews Russ Morgan, founder of Wealth Without Wall Street, who shares his journey from financial advisor to advocating for financial independence through passive income. After the 2008 financial crisis exposed flaws in traditional investing advice, Russ shifted his focus to helping individuals take control of their financial future. He emphasizes that true financial freedom comes from building passive income that exceeds monthly expenses, rather than relying on traditional markets or advisors who may not actively manage individual portfolios. The conversation centers on the importance of understanding your “investor DNA” — aligning investment strategies with your personality, strengths, and preferences. Russ explains that many people fail to invest because of fear, confusion, or lack of clarity, and encourages listeners to simplify their approach by identifying their goals, access to capital, and preferred level of involvement. He introduces practical frameworks, such as measuring progress toward financial freedom and leveraging resources like time, relationships, or expertise to get started. Ultimately, he stresses that success comes from taking action, building systems, and consistently evaluating opportunities that align with your personal investment style.

    28 min
  8. EP413 How AI Can Handle Tenant Maintenance Requests in Real Time with Angelina Canelli

    MAR 26

    EP413 How AI Can Handle Tenant Maintenance Requests in Real Time with Angelina Canelli

    In this episode of Canadian Investing in the US, Glen Sutherland interviews Angelina Cannelli, CEO and founder of RAI, an AI-driven real estate solutions company. Angelina explains how her background in banking, consulting, technology, and personal investing led her to create Mondo, an app designed to automate property management from beginning to end. Unlike traditional platforms that handle only specific tasks, her system integrates tenant communication, vendor coordination, financial tracking, documentation storage, and operational oversight into one centralized dashboard accessible in real time by owners, managers, and tenants. The conversation explores how AI can address common investor challenges such as inflated vendor invoices, delayed maintenance responses, and limited transparency in building operations. Angelina outlines features like automated maintenance triaging, real-time invoice analysis, faster tenant screening, and “white-glove” vendor coordination for large projects. She positions AI-driven automation as a way to increase efficiency, lower costs, and potentially reduce reliance on traditional property managers, particularly for investors managing properties remotely or at scale.

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

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