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

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

A Canadian Investing in the U.S. with Glen Sutherland is a education podcast hosted by Glen Sutherland, with 422 episodes on record and a Required Pod Score of 80.

Glen Sutherland hosts A Canadian Investing in the U.S. with Glen Sutherland, a education show with 422 episodes published.

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

  EP439 Canada vs. USA Real Estate Where Can Investors Still Find Cash Flow with Bryce Kaminsky

  Sep 30, 202622 min

  In this episode of Canadian Investing in the US, Glen reconnects with Bryce Kaminsky to compare the realities of real estate investing in Canada versus the United States. Bryce shares his experience investing in Cleveland and explains why many Canadian investors are struggling to make buy-and-hold rentals work due to higher purchase prices, rising renovation costs, mortgage renewals at higher rates, and increasingly thin cash flow. He contrasts that with lower-cost U.S. markets where investors may still be able to find stronger rental yields, especially by targeting off-market opportunities and properties that can be improved through renovations. The conversation also explores where opportunities may still exist for investors who want to stay in Canada. Bryce suggests buying aggressively below market value, focusing on solid working-class neighborhoods, using forced appreciation, and being careful not to over-leverage during refinances. Glen and Bryce also discuss property management for remote U.S. investing, including why scenario-based interview questions can reveal far more than simply comparing management fees. The broader message is that investors should focus less on geography alone and more on finding properties that truly produce cash flow, fit their risk tolerance, and support their long-term goals.

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

  EP438 Real Estate Wire Fraud How Investors Can Avoid Losing Their Money with Robert Siciliano

  Sep 23, 202634 min

  In this episode of Canadian Investing in the US, Glen speaks with security-awareness expert Robert Siciliano about the growing threat of scams, identity theft, wire fraud, and social engineering—especially for Canadians investing remotely in U.S. real estate. Robert explains that modern scammers operate like sophisticated businesses and often rely less on hacking technology than on manipulating human behaviour. He introduces the concept of becoming a “strategic human firewall” and shares his AAA protocol: Analyze, Authenticate, Act. Investors should recognize manufactured urgency, independently verify who they are communicating with, and never rely on phone numbers, email addresses, links, or wiring instructions contained in an unexpected message. The conversation becomes especially relevant to real estate investors when Robert explains why criminals target email accounts and how compromised or spoofed communications can be used to impersonate title companies, attorneys, lenders, buyers, and sellers. He shares a sophisticated scam in which criminals impersonated Google Security, triggered legitimate Google emails and text messages, and nearly convinced him to authorize access to his own account. Robert recommends using unique passwords for every account, a password manager, and two-factor authentication on all critical financial and email accounts. The takeaway for investors is simple: when money, account access, or wiring instructions are involved, slow the process down and independently verify everything before acting.

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

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

  Sep 16, 202622 min

  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

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

  EP436 Why Self Storage Beats Rental Properties with Fernando Angelucci

  Sep 8, 202627 min

  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.

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

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

  Sep 2, 202657 min

  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.

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