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. 1d ago

    EP437 When To Add a Canadian Corp to your USA Structure with Tim Miron

    In this episode of Canadian Investing in the US, Glen speaks with repeat guest Tim Miron, founder of Pursuit CPA, about when a Canadian real estate investor should add a Canadian corporation to their U.S. investment structure. Tim explains that the answer depends on the investor’s long-term goals, where the original investment capital comes from, and what they eventually plan to do with U.S. profits. One major reason to use a Canadian corporation is when the investor already has retained earnings inside an operating company or holding company; instead of withdrawing those funds personally and triggering another layer of tax, the corporation may be able to deploy more of that capital into U.S. investments. They also discuss moving money between Canadian and U.S. entities through properly documented management fees and intercompany loans. The conversation also covers the additional compliance that comes with adding a Canadian corporation, including setup costs, annual corporate tax filings, foreign reporting requirements, legal minute-book maintenance, and HST considerations. Tim explains that services provided by a Canadian company to a U.S. customer may generally be zero-rated for HST, while the Canadian corporation can potentially recover HST paid on eligible business expenses. They also discuss a second major reason to add a Canadian holding company later: once a U.S. real estate portfolio becomes profitable, investors may want to move profits back to Canada without taking the money personally, allowing the corporation to reinvest in stocks, bonds, Canadian real estate, or other opportunities

    EP437 When To Add a Canadian Corp to your USA Structure with Tim Miron

  2. Sep 9

    EP436 Why Self Storage Beats Rental Properties with Fernando Angelucci

    In this episode of Canadian Investing in the US, Glen speaks with Fernando Angelucci, CEO of SSSE, a private equity firm focused on self-storage acquisitions and development across the United States. Fernando explains why he moved away from single-family and small multifamily investing after years of dealing with high management demands, contractor issues, tenant problems, and relatively lower profits. He shares how self-storage allowed him to operate fewer, larger transactions while increasing profitability and working with more sophisticated lenders, operators, and professionals. The conversation dives into Fernando’s self-storage strategy, including sourcing more than 90% of acquisitions off-market, building long-term relationships with owners, targeting larger facilities, expanding properties, increasing NOI, and eventually selling to institutional buyers. He also discusses financing options such as SBA loans and seller financing, the legal advantages of self-storage compared with residential rentals, auction procedures for delinquent units, stabilized occupancy levels, and dynamic pricing strategies similar to airlines. For investors looking for a scalable commercial real estate niche with fewer traditional landlord headaches, Fernando makes a strong case for self-storage as a business as much as a real estate investment.

    EP436 Why Self Storage Beats Rental Properties with Fernando Angelucci

  3. Sep 2

    EP435 How to Identify and Sell Underperforming Rental Properties with Tim Tsai

    In this episode of Canadian Investing in the US, Glen reconnects with experienced real estate investor Tim Tsai to discuss one of the most overlooked decisions in real estate: when it makes sense to sell a rental property instead of continuing to hold it. Tim explains that he evaluates properties based on cash flow, NOI, cash-on-cash return, maintenance costs, and opportunity cost rather than simply focusing on how many doors he owns. After more than two decades of investing across Canada, the U.S., and the UK, Tim is now exiting the UK market because the numbers no longer justify keeping the properties. He emphasizes that aging properties often require increasing amounts of capital and attention, and investors should regularly ask whether their equity could be producing stronger returns somewhere else. Glen and Tim also challenge the popular real estate mindset of accumulating as many rental units as possible, arguing that portfolio performance matters more than door count. They discuss lease options as a strategy that can generate upfront option money, monthly cash flow, and a future sale while potentially reducing traditional landlord-management headaches. The conversation also explores the hidden emotional cost of owning troublesome properties, the importance of redeploying trapped equity, and why inherited or underperforming rental portfolios can eventually become liabilities rather than assets. Tim closes by emphasizing that investors make much of their money—and protect themselves from future problems—by buying correctly from the very beginning.

    EP435 How to Identify and Sell Underperforming Rental Properties with Tim Tsai

  4. Aug 26

    EP434 Is Mexico Real Estate a Good Investment? What Canadians Should Know! with Matthew Scott

    In this episode of Canadian Investing in the U.S., Glen reconnects with repeat guest Matthew Scott, a Canadian real estate investor who has flipped approximately 40 properties in Southwestern Ontario and raised more than $10 million in capital. After travelling to Mexico and deciding to spend more time there, Matthew shifted his attention toward Mexican real estate, land development and the process of preparing land for future development. He discusses his work with local developers, plans to create a real estate agency and his involvement in a large land-entitlement project that could eventually be sold to a developer. Matthew explains how he evaluates potential areas by studying tourism, government development plans, infrastructure expansion and the activity of other developers. The conversation also examines the risks of purchasing land in Mexico, including unclear ownership records, restrictions on certain types of land, unreliable representatives and the importance of working with experienced lawyers and notaries. Matthew discusses cash purchases, financing and residency considerations before sharing how living in Mexico has changed his lifestyle and perspective. He describes his personal experiences with the culture and safety while emphasizing the importance of knowing the area, avoiding flashy displays of wealth and building relationships with trustworthy local professionals.

    EP434 Is Mexico Real Estate a Good Investment? What Canadians Should Know! with Matthew Scott

  5. Aug 13

    EP433 How Rent Reporting Can Improve Credit Scores and Reduce Late Rent with Steve Harmer

    In this episode of Canadian Investing in the U.S., Glen speaks with Steve Harmer, president of FrontLobby, about how rent reporting and tenant screening can help landlords reduce risk while helping responsible tenants build their credit history. Steve explains how rental payments can be reported to major credit bureaus in both Canada and the United States, including Equifax, TransUnion and Experian depending on the country. Because rent is often a tenant’s largest monthly financial obligation, reporting on-time payments can help establish or strengthen a tenant’s credit profile. Steve also discusses a study conducted with Equifax Canada that found some participants experienced credit-score increases in the range of 40–80 points during their first six months, although the impact varies significantly depending on each tenant's existing credit history. The conversation also explores how landlords can use rent reporting as part of their tenant-screening and rent-collection strategy. Steve explains how landlords can screen applicants using credit reports, background checks and identity verification, while rental-payment history can provide additional insight into how applicants have handled previous leases. They also discuss reporting late or unpaid rent, obtaining tenant consent for positive reporting, reporting former tenant debt, and how small landlords can implement the system with only a few rental properties. Ultimately, the episode shows how rent reporting can create accountability for tenants while rewarding those who consistently pay on time, potentially creating a more balanced relationship between landlords and renters.

    EP433 How Rent Reporting Can Improve Credit Scores and Reduce Late Rent with Steve Harmer

  6. Aug 6

    EP432 Why Real Estate Investors Are Shifting from Flipping to the BRRRR Strategy with Juan Munoz

    In this episode of Canadian Investing in the U.S., Glen speaks with Jeff, an experienced real estate investor, hard money lender and coach who operates Best REI Funding, Alpha Lending and Best Capital Management. Jeff explains how his career evolved from actively flipping houses and managing rentals to focusing primarily on real estate lending and education. He emphasizes that successful investors should avoid becoming locked into a single strategy and instead develop the skills to evaluate whether each property is best suited for wholesaling, flipping, refinancing, holding as a rental or selling on the retail market. Jeff also discusses how higher interest rates have caused a major shift from fix-and-flip projects toward the BRRRR strategy. His lending companies previously financed approximately 80% flips and 20% BRRRR projects, but that ratio has now reversed. The conversation also explores the increasing challenges surrounding DSCR loans, including changing underwriting requirements, reduced loan-to-value ratios, higher reserve requirements and unexpected closing delays. Jeff explains that investors can reduce their risk by underwriting properties with multiple exit strategies and matching the property, financing and investment plan rather than forcing every deal into a predetermined strategy.

    EP432 Why Real Estate Investors Are Shifting from Flipping to the BRRRR Strategy with Juan Munoz

  7. Jul 30

    EP431 Flipping vs BRRRR: Which Strategy Wins in Today's Market? with Jeff Cichocki

    Interest rates, lending guidelines, and real estate investing strategies are changing faster than ever. In this episode, Glen sits down with experienced lender and investor Jeff Cichocki to discuss why today's investors need to stop forcing every property into a single strategy and instead focus on finding the highest and best use for every deal. They dive into the shift from flipping toward BRRRR investing, why wholesalers often have the greatest flexibility, and how having multiple exit strategies can dramatically improve your odds of success. Jeff also shares what he's seeing from the lending side of the business, including why DSCR loans have become more difficult to close, how underwriting requirements are changing almost daily, and why investors need to understand financing just as well as they understand real estate. Whether you're flipping houses, building a rental portfolio, wholesaling, or simply trying to navigate today's financing landscape, this episode is packed with practical insights to help you make better investment decisions.

    EP431 Flipping vs BRRRR: Which Strategy Wins in Today's Market? with Jeff Cichocki

  8. Jul 23

    EP430 Why Dallas TX Is One of America's Best Real Estate Markets Right Now with Paul Hopkins

    In this episode of Canadian Investing in the US, Glen Sutherland sits down with Paul Hopkins, VP of Investments at CPI Capital, to break down why Dallas–Fort Worth has become one of the most attractive apartment investment markets in the United States. Paul shares his journey from construction and engineering into large-scale multifamily investing before explaining the key economic drivers behind Dallas' continued growth, including population migration, Fortune 500 employers, job creation, infrastructure investment, and why major investors continue to target Texas. The conversation also tackles one of the biggest questions investors are asking today: Is now actually the right time to invest in Dallas? Glen and Paul discuss the recent apartment oversupply, the challenges many syndicators faced with bridge financing and rising interest rates, and why those same market conditions have created opportunities to purchase quality apartment communities at significant discounts. They also explain why Class B multifamily properties remain attractive, how supply and demand are shifting back in investors' favor, and what makes the Louisville, Texas submarket stand out for long-term growth. Whether you're an active investor or simply want to understand where the U.S. multifamily market is heading, this episode provides valuable insights into today's investment landscape.

    EP430 Why Dallas TX Is One of America's Best Real Estate Markets Right Now with Paul Hopkins
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