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

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 rese...

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 pa...

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 custom...

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 Canadi...

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...

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 un...

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 bu...

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 wit...

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 ear...

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...

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 eco...

In this episode of Canadian Investing in the US, Glen Sutherland interviews franchise consultant Jon Ostenson to explore how franchising can be a powerful wealth-building strategy — especially for real estate investors and Canadians looking to expand into the U.S. market. John shares how he transitioned from the corporate world to franchising, became President of ShelfGenie, and now helps investor...

In this episode of Canadian Investing in the U.S., Glen Sutherland interviews Ruslan Benko, a Canadian investor who transitioned from buying duplexes in Ontario and Alberta to scaling his portfolio in the United States. Ruslan explains how rising Canadian property prices and stagnant rents pushed him to seek better cash flow and scalability opportunities south of the border. After discovering asse...

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 e...

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 futu...

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...

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 jo...

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 Ca...

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 l...

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 fli...

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, wha...

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 p...

In this episode of A Canadian Investing in the U.S., Glen sits down with Ali Rostamee to discuss his journey from immigrating to Canada in 2010 to ultimately becoming financially free through real estate. Ali shares how reading Rich Dad Poor Dad shaped his mindset early on, leading him to pursue cash-flowing duplexes in Edmonton before hitting lending limits. That forced him to expand his educatio...

Raheem Madjavi from Knightsbridge FX joins Glen Sutherland to unpack what’s driving the Canadian dollar vs. U.S. dollar and what Canadians should watch in 2026. They discuss key macro factors that move currency markets—interest rate differentials, jobs/GDP, oil and commodities, and trade-policy uncertainty—plus why the USD/CAD rate can stay volatile when policy shifts and headlines change fast. Ra...

In this episode, Glen Sutherland reflects on eight years of releasing a podcast episode every single week and breaks down how long-term consistency has played a major role in his success. He explains that his results didn’t come from viral moments or overnight wins, but from showing up week after week—even when it was boring, unsexy, and felt like nothing was happening. Glen highlights why most pe...