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

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

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

    2D AGO

    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
  2. 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
  3. EP412 Negociating Seller Financing, and Finding Win-Win Deals with Marti Jo Watts

    MAR 19

    EP412 Negociating Seller Financing, and Finding Win-Win Deals with Marti Jo Watts

    Marti Jo Watts shares a raw, emotional turning point: before COVID she was a high-earning medical consultant managing large territories in Indiana and Kentucky, until her company terminated hundreds of consultants during the vaccine-era mandate period. As a single mom already carrying years of stress around her son’s long medical journey (18 head surgeries from infancy to adulthood), losing her job collapsed her finances and stability—house gone, car gone, cramped apartment life, and the humbling moment of her kids helping pay bills. A defining scene hits when she nearly takes the vaccine out of fear of losing everything, but a traffic accident makes her miss the appointment; her son’s quiet disappointment (“I thought you would fight harder”) becomes the catalyst that anchors her back to her principles and faith. At her lowest, Marty stumbles into a coaching program on YouTube and realizes real estate isn’t reserved for the wealthy—then invests her last resources to join the community and learn creative finance. Momentum follows: a first deal flipping 40 acres with an easement issue (moving fast before competitors), then a “relationship deal” where her best friend asks her to sell a medical clinic in exchange for a Hawaii trip—leading to a partnership purchase and plans to open a medical spa instead of flipping. The conversation turns practical: Marty emphasizes telling people what you do, solving the seller’s “pain,” keeping deals win-win, and using creative terms (seller financing / payment structures) to benefit sellers—especially with tax and “mailbox money” advantages. She closes with a motivational call: regardless of where you’re starting, have conversations, don’t fear big numbers, and build your path deal by deal.

    30 min
  4. EP411 What To Do When You Receive an Unexpected Tax Bill with Tim Miron

    MAR 12

    EP411 What To Do When You Receive an Unexpected Tax Bill with Tim Miron

    In this episode of Canadian Investing in the US, Glen Sutherland sits down with returning guest Tim Miron, founder and president of Pursuit CPA, to discuss what investors should do when they receive an unexpected tax bill. Tim explains that the most important step is to file your taxes on time, even if you cannot immediately pay the balance. Filing late can trigger significant penalties—such as Canada’s 5% late filing penalty plus additional monthly interest—which can quickly increase the amount owed. Instead of avoiding the issue, Tim encourages investors to determine the exact amount owed as early as possible so they can create a plan to deal with it. The conversation also explores practical strategies for managing a surprise tax bill, including using lower-interest financing (such as a line of credit or refinancing), negotiating payment arrangements with tax authorities, and exploring taxpayer relief programs if extraordinary circumstances caused the issue. Tim emphasizes the importance of proactive tax planning, recommending that investors review their tax strategy in mid-year so there’s still time to make adjustments before year-end. Glen and Tim also highlight the value of communicating with your accountant before making major financial decisions—like buying vehicles or structuring business expenses—so that investors can deploy their money in the most tax-efficient way possible.

    19 min
  5. EP410 How Canadians Can Legally Exit Canada’s Tax System with Bobby Casey

    MAR 5

    EP410 How Canadians Can Legally Exit Canada’s Tax System with Bobby Casey

    Glen Sutherland interviews Bobby Casey, an American international tax lawyer and “slowmad” who splits his time between North Carolina, Mexico, and Latvia. Bobby explains how his residency lifestyle works in practice, and why Americans are “unicorns” globally: the U.S. taxes citizens on a citizenship basis, meaning Americans still file (and may owe) U.S. taxes even when living abroad—though tools like the Foreign Earned Income Exclusion and foreign tax credits can reduce the hit. The conversation then shifts to Canadians and cross-border tax/residency strategy. Bobby outlines how Canadians can more easily exit Canadian tax residency by minimizing key residential ties (e.g., primary home, spouse, dependent children) and properly filing their departure return—while noting there can be exit-tax considerations and changed tax treatment of property kept behind. He also shares practical notes on living abroad (including why he disliked Belize) and digs into real estate rules for foreigners (e.g., Mexico’s restricted zones and use of a fideicomiso). Finally, Bobby explains why a U.S. LLC can be a powerful structure for non-U.S. digital nomads/remote entrepreneurs (depending on “effectively connected income” and where work is performed), and closes by describing his company formation/compliance platform, BusinessAnywhere.io.

    42 min
  6. EP409 How to Entitle Land and Sell to National Home Builders with Brandon Cobb

    FEB 26

    EP409 How to Entitle Land and Sell to National Home Builders with Brandon Cobb

    Brandon Cobb returns to the show to break down how he went from medical device sales to building a real estate business focused on land development and land entitlements. After getting fired unexpectedly, Brandon learned a hard truth: nobody is going to protect your financial future but you. That turning point led him through a few failed ventures before he discovered real estate—starting with flipping and building homes, then scaling into larger land deals after national builders began offering to buy his parcels. In this episode, Brandon explains a simplified, lower-risk approach to land development investing: identify the right parcels, put land under contract with a 90–120 day due diligence period, hire a civil engineer for a concept plan, get early buy-in from the city, and secure an end buyer (often national home builders) before moving through approvals. He also shares where deals can break down—traffic studies, municipal requirements, unexpected costs—and how they mitigate risk with non-refundable buyer deposits to cover entitlement expenses. If you’re an experienced investor looking to level up from single deals into bigger land opportunities, this is a step-by-step look at how the entitlement and development game really works.

    21 min
  7. EP408 High-Income Activities Canadians Must Focus On in U.S. Real Estate with Joe Evangelisti

    FEB 19

    EP408 High-Income Activities Canadians Must Focus On in U.S. Real Estate with Joe Evangelisti

    Glen brings back Joe Evangelliti to share his “5 Bottlenecks” framework—a universal set of constraints that keep entrepreneurs (especially real estate investors) stuck. The 5 bottlenecks framework 1) Mindset / limiting beliefs You don’t get what you “conceive”—you get what you believe you can achieve. “Rational lies” = the stories we tell ourselves to avoid action (not smart enough, not ready, what will people think, etc.). Fastest unlock question: “What do I want?” (not what spouse/parents/friends want). 2) Clarity + reverse engineering (Point B → Point A) People plan vacations with precision but plan their lives in vague “wish” language. Define Point B clearly, assess Point A honestly, then close the gap. 3) Toolkit audit (simplify your tools/systems) Too much tech can create complexity and distraction. Quote-worthy idea: if you can’t do it with notepad + pen + phone, software won’t save you. Build consistent deal flow first; avoid shiny-object “easy button” chasing. 4) Rule of 168 (time control) Everyone has 168 hours/week—top performers just allocate it differently. Focus on: High-income activities (directly produce revenue now) High-gain activities (life/relationships/health that matter long-term) Track what moves the needle (e.g., offers made). Many people feel busy but do zero needle-moving actions. Calendar discipline = presence. “Show me your calendar and I can almost tell you your net worth.” 5) The trifecta (the “bow”) Execution (do the work, ship the offer, take the shot) Course correction (pivot around obstacles instead of quitting or forcing a broken plan) Radical accountability (someone outside your inner circle who won’t let you off the hook)

    43 min
  8. EP407 Ontario Bill 60 Explained: What Landlords Need to Know About LTB Changes with Kayla Andrade

    FEB 12

    EP407 Ontario Bill 60 Explained: What Landlords Need to Know About LTB Changes with Kayla Andrade

    In this episode, Glen Sutherland sits down with Ontario landlord advocate Kayla Andre to unpack what Bill 60 really means for landlords navigating the challenges of the Ontario Landlord and Tenant Board. Kayla explains how the bill shortens the timeline for filing non-payment applications, limits last-minute maintenance complaints used to delay hearings, and aims to standardize what qualifies as persistently late rent. She also highlights efforts to improve enforcement through additional sheriffs, clearer rules around set-aside orders, and better visibility of LTB decisions to help landlords identify repeat offenders. Beyond the legal changes, the conversation explores the bigger picture: landlords leaving the Ontario market, municipal renoviction bylaws conflicting with provincial authority, and how policy missteps may be driving rental prices higher and discouraging investment. Kayla shares real examples of serial non-payment cases that escalated to fraud charges and emphasizes why both landlords and taxpayers should be paying attention. For many listeners, this episode explains why Ontario investors have increasingly looked to U.S. real estate—and whether reforms like Bill 60 could begin to restore confidence at home.

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

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