<description>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.

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In this episode of Canadian Investing in the US, …

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.



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

<description>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.

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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.



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

<description>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.</description>

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.

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

<description>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.</description>

Marti Jo Watts shares a raw, emotional turning po…

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.

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

<description>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.</description>

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.

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

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