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

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.

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.

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.

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.

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.

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.

Finding great real estate deals starts with finding motivated sellers—and that's exactly what we dive into in this episode. I sit down with digital marketing expert and real estate investor Brian Driscoll to discuss how investors can generate high-quality direct-to-seller leads using Google Ads and other inbound marketing strategies. We compare inbound marketing with traditional methods like cold calling, driving for dollars, and purchased lists, and explain when each approach makes the most sense as your investing business grows. Brian also shares the systems successful investors use to convert more leads into deals, including why speed to lead is one of the biggest factors in closing profitable opportunities. We discuss CRMs, automation, lead management, negotiation, and why approaching sellers with a problem-solving mindset consistently outperforms high-pressure sales tactics. Whether you're wholesaling, flipping, buying rentals, or using creative financing strategies like lease options and seller financing, this episode is packed with practical advice to help you find more off-market opportunities and scale your real estate business.

Canadians investing in U.S. real estate often assume the financing process works just like it does at home—but that assumption can lead to costly mistakes. In this episode, Glen Sutherland sits down with cross-border mortgage expert Chris Micucci to break down the biggest lending misconceptions Canadian investors make and explain how U.S. investment financing really works. From DSCR loans and reserve requirements to closing costs, corporate structures, wire transfers, and choosing the right lender, you'll learn the practical lessons that can save you thousands of dollars and prevent deals from falling apart. Whether you're buying your first U.S. rental or expanding your portfolio, this episode will help you avoid the mistakes that catch many Canadian investors off guard. glensutherland.com/lenders The 13 Lending Mistakes Canadians Make: 1. Thinking you qualify based on your personal income Many Canadians assume U.S. lenders care about salary, T4s, tax returns, or employment. For DSCR loans, the property qualifies—not you. 2. Assuming you need perfect personal finances to buy Canadians often believe they need extensive financial documentation. In reality, many U.S. investment loans primarily focus on the property's cash flow and your down payment funds. 3. Believing Canadian mortgage rules apply in the U.S. Many investors expect pre-approvals, qualification rules, and lending policies to work the same way they do in Canada. They don't. 4. Getting pre-approved before finding the property In Canada, you're approved for a dollar amount. In the U.S., you're generally approved for a specific property that cash flows. Many Canadians misunderstand this difference. 5. Buying properties that are too inexpensive Ironically, smaller loan amounts are often harder to finance because many lenders prefer larger loans and higher-value properties. 6. Being surprised by U.S. closing costs Many Canadians experience sticker shock because title fees, lender fees, appraisals, escrow deposits, and other costs are itemized instead of hidden in the mortgage. 7. Waiting until the last minute to transfer money International wire transfers can be delayed by compliance reviews or audits. Waiting until the week of closing can jeopardize the deal—and potentially your earnest money deposit. 8. Waiting too long to set up your U.S. entity and EIN Many investors don't realize that obtaining an EIN can take weeks, especially during busy IRS periods. Waiting can delay financing and closing. 9. Setting up the wrong ownership structure Some Canadian tax structures work well legally but are difficult—or impossible—for many U.S. lenders to finance. Structuring without considering lending requirements can create expensive delays. 10. Not having enough reserve funds Many first-time investors budget only for their down payment. Most lenders also expect to see several months of mortgage reserves in a U.S. bank account. 11. Shopping only by interest rate A lower rate isn't always the better loan. Points, lender fees, closing costs, and how long you plan to hold the property all matter. 12. Comparing different loan products as if they're identical Many investors compare refinance quotes, construction loans, fix-and-flip loans, and purchase loans without realizing they're completely different products. 13. Using lenders who don't understand Canadian investors One of the biggest mistakes is working with lenders who primarily serve Americans. They may quote attractive terms initially, only for underwriting to discover you're Canadian and change the loan shortly before closing

In this episode of Canadian Investing in the USA, Glen Sutherland sits down with mobile home park investor and fund manager Ali Nazar to explore why manufactured housing communities have become one of the most resilient and attractive real estate asset classes. Ali shares his family's multi-generational real estate journey, beginning with single-family rentals and transitioning into mobile home parks after the high-interest-rate environment of the early 1980s. Drawing on more than 45 years of experience, he explains how affordable housing demand, tenant-owned homes, and diversified income streams have helped manufactured housing communities weather multiple recessions and market downturns while continuing to provide stable cash flow and long-term wealth creation. The conversation dives deep into how successful mobile home park operators create value through infill strategies, seller financing, and converting park-owned homes into resident-owned homes. Ali discusses the importance of scale, why he targets communities with 50+ sites, and how investors can avoid common underwriting mistakes when evaluating park-owned homes versus lot-rent income. Glen and Ali also explore financing options, tenant retention, rent growth, operational efficiencies, and the advantages of owning affordable housing in today's economic environment. Whether you're an experienced investor looking to diversify or someone curious about manufactured housing for the first time, this episode provides a practical look at how mobile home parks can deliver strong returns while serving a critical housing need.

In this episode of Canadian Investing in the USA, Glen Sutherland sits down with digital marketing expert and AIS Media founder, Thomas Harpointner, to discuss one of the biggest shifts happening online today: the rise of AI-powered search. Thomas explains how tools like Google Gemini, ChatGPT, and other AI platforms are changing the way consumers find information and how businesses attract customers. While many companies are seeing website traffic decline as AI provides answers directly within search results, Thomas reveals why this isn't necessarily bad news. In many cases, businesses are receiving fewer but far more qualified leads because AI is helping educate prospects before they ever visit a website. The conversation dives into practical strategies for ensuring your business remains visible in an AI-driven world. Thomas shares why content is still king, how authority and credibility influence AI recommendations, and why podcasts, videos, blogs, social media, and industry publications all play a role in building digital authority. He also discusses the importance of structured content, SEO fundamentals, thought leadership, and understanding what your ideal customer is actually searching for rather than relying on assumptions. For business owners, investors, and entrepreneurs looking to stay relevant as AI reshapes online discovery, this episode offers valuable insights into how to position yourself as a trusted authority that AI platforms will reference and recommend.

Brad Beauchamp, a Canadian mortgage broker based between Vaughan and West Palm Beach, joins Glen Sutherland to explain how Canadians can finance U.S. real estate investments using DSCR loans and cross-border lending strategies. Brad shares his own immigration journey from obtaining an L1 executive visa to eventually becoming a U.S. citizen, before diving into the opportunities available for Canadian investors south of the border. The conversation highlights how DSCR (Debt Service Coverage Ratio) loans allow investors to qualify based primarily on a property’s cash flow instead of personal income or employment verification, making it easier for Canadians to scale portfolios in markets like Florida, Ohio, Texas, and Alabama. Brad explains that while Canadians can secure financing without U.S. credit history, investors with U.S. tax IDs, entities, residency ties, or established FICO scores can often access lower rates and better leverage. The episode also focuses heavily on structuring and protecting investments properly when buying U.S. real estate. Brad and Glen discuss the importance of setting up U.S. LLCs, understanding cross-border taxation, using professional advisors, and avoiding common mistakes such as holding properties personally instead of through entities. They explain hidden costs Canadians often overlook — including underwriting fees, loan origination fees, title fees, prepayment penalties, and refinancing costs — while emphasizing that proper planning can save investors significant money long term. The discussion covers partnerships with Americans, refinancing strategies, seasoning periods, and how the larger U.S. market creates more financing flexibility and opportunity than Canada. Overall, the interview serves as a practical guide for Canadians who want to leverage U.S. financing, build cash-flowing portfolios, and avoid costly structural and lending mistakes. Find out what type of US real estate investment would fit you best at: https://acanadianinvestingintheusa.com/QUIZ

Benny Delaney shares his journey from growing up in India, building a business and investing in ultra-expensive real estate in Hong Kong, and eventually immigrating to Canada in 2017 for his children’s future. After buying duplexes in Oshawa and Peterborough, Benny discovered U.S. real estate investing through Glen Sutherland’s coaching and became attracted to the flexibility of DSCR loans in the United States. Unlike Canadian lenders that focused heavily on proving employment income, Benny found that U.S. lenders cared more about the property’s cash flow potential. This allowed him to scale into properties in Florida and Detroit despite being semi-retired and no longer operating an active business. The interview also dives deeply into Benny’s strategy of remotely managing student rentals in Florida from Toronto. He explains how building a reliable local team — including realtors, plumbers, HVAC contractors, cleaners, and leasing support — made remote investing practical. Benny discusses handling student tenants, lease-ups, payment systems, maintenance requests, and tenant screening while emphasizing that real estate investing is ultimately a business built around problem-solving. The conversation highlights the difference between investing for appreciation versus investing for cash flow, with Benny prioritizing higher-income properties like student rentals and Airbnbs to support his semi-retired lifestyle. The episode offers valuable insight for Canadians looking to invest remotely in U.S. markets while leveraging creative financing and higher cash-flow opportunities unavailable in many Canadian cities. What type of Investor are you? Take the Quiz? https://acanadianinvestingintheusa.com/quiz

In this episode of Canadian Investing in the US, Glen Sutherland sits down with estate planning expert Mark Halpern to unpack the critical importance of proactive estate planning for investors and families. Mark shares personal insights that shaped his career and emphasizes the dangers of failing to plan—highlighting how something as simple as not having a will can create financial hardship and unnecessary stress for loved ones. The conversation explores foundational elements like wills, powers of attorney, and the risks of dying intestate, especially for Canadians with families and real estate holdings. The discussion goes deeper into advanced strategies, including probate tax minimization, multiple wills, and the strategic use of tax-exempt life insurance to preserve wealth and cover future tax liabilities. Mark also introduces the concept of an “estate directory” to ensure loved ones can easily access critical information in emergencies. Together, Glen and Mark emphasize that successful investing isn’t just about building wealth—it’s about protecting it, transferring it efficiently, and avoiding costly mistakes through proper planning and the right professional team. What US real estate strategy would work best for you? https://acanadianinvestingintheusa.com/QUIZ

In this episode of Canadian Investing in the US, host Glen Sutherland welcomes recurring guest and CPA Tim Miron of Pursuit CPA to discuss strategies Canadian investors can use to reduce taxes on U.S. rental properties. Tim explains the difference between passive and active income taxation, noting that rental income earned inside a corporation can be taxed at rates approaching 50%, while active business income in a Canadian corporation may be taxed as low as 12% in Ontario. The conversation focuses on a strategy where a Canadian corporation acts as a property management company for U.S. rental properties, charging management fees to the U.S. entity and converting part of the rental income into lower-taxed active income. Tim emphasizes the importance of charging realistic management fees, maintaining proper invoicing, and ensuring the arrangement reflects legitimate property management activity. Glen and Tim also discuss practical considerations such as bookkeeping complexity, moving money consistently between entities, and how these strategies change depending on whether investors are holding stabilized rentals, actively renovating properties, or operating other active businesses. Tim explains that rehab projects may justify significantly higher management fees due to the increased workload, while investors already generating active business income through flipping or property management may have alternative tax planning options available. Throughout the episode, the two stress the importance of proper structuring and working with experienced cross-border tax professionals to ensure compliance and maximize tax efficiency for Canadian investors operating in the U.S. real estate market.

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.

In this episode of Canadian Investing in the US, Glen Sutherland interviews Chris Lento, a full-time real estate investor and operator of EM Capital Group, who focuses on acquiring and managing multifamily properties in the U.S. Southeast. Chris shares his journey from starting with small “three-decker” properties in Boston to scaling into large 100+ unit apartment complexes. He emphasizes how early hands-on experience with tenant management and maintenance provided a strong foundation for understanding costs, operations, and decision-making at scale, even though larger properties require teams, systems, and professional management structures. The conversation highlights the importance of systems, processes, and strong property management when scaling a real estate portfolio. Chris explains how his business uses structured acquisition criteria, standardized operating procedures, and tools like project management software to streamline operations and decision-making. A major focus is placed on selecting and managing property managers, including identifying red flags, asking detailed operational questions, and acting quickly when issues arise. He also discusses his current role in sourcing deals, raising capital, and overseeing asset management, while noting that despite recent market slowdowns, improving deal conditions and more realistic pricing are creating new opportunities for investors.

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.

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.