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

Lancelot Lennard is a Florida realtor, investor, contractor, and non-profit founder who focuses on the Daytona / Volusia County area. He explains why he left Miami for Daytona: Miami’s become a “billionaire playground” with weak ROI for small investors, while Daytona still has mom-and-pop landlords, realistic prices, and solid opportunities for both buy-and-hold and flips. He breaks down where he...

In this episode of A Canadian Investing in the U.S., Glen Sutherland sits down with Dave Seymour to unpack his incredible journey from blue-collar firefighter to nationally recognized real estate investor and educator. Dave shares how financial illiteracy, predatory lending, and the 2008 financial crisis nearly cost him everything—and how a pivotal decision to invest in education and take massive...

In this episode of Canadian Investing in the U.S., Glen sits down with Tim Miron, CPA, founder of Pursuit CPA, to walk Canadian investors through how to properly prepare for tax season, especially when dealing with cross-border real estate and business income. Tim explains why January–March is the ideal time to get organized instead of waiting until April, and highlights common bottlenecks that sl...

In this special 400th episode, Glen shares the full story of how he bought his very first U.S. investment property and all the mistakes that came with it. After struggling to scale his Canadian portfolio due to rising prices, lender limitations, and tenant issues, he turned to U.S. podcasts for answers and eventually bought a turnkey property in Huntsville, Alabama using a HELOC from his Ontario h...

In this episode of A Canadian Investing in the U.S., Glen Sutherland welcomes renowned data-driven real-estate investor Neil Bawa. Neil shares his journey from tech entrepreneur to full-time real-estate operator after selling his company in 2013 and facing a huge tax bill that pushed him into multifamily investing. He now manages a $660 million portfolio across multifamily, self-storage, industria...

In this episode of Canadian Investing in the U.S., host Glen Sutherland interviews Priscilla (Pre) Cosentino, a U.S.-based financial advisor, author, and mentor who specializes in helping clients build a true wealth mindset. Priscilla explains that financial planning is about much more than simply accumulating money—it’s about aligning one’s financial goals with personal values and life purpose. S...

In this episode of Canadian Investing in the U.S., Glen Sutherland welcomes two guests — cross-border CPA Chris McAvoy of LEAP ACT and Tim Myron, founder of Pursuit CPA in Burlington, Ontario. The discussion centers on the merger between LEAP ACT and Pursuit CPA, which will combine their teams into a single 20-person firm with offices in both Burlington and Niagara. The merger allows clients from...

Patrick Grimes joins Glen Sutherland to share his evolution from a corporate engineer to a full-time investor focused on building recession-resilient wealth. After losing big during the 2008 financial crisis, Patrick rebuilt his strategy by shifting away from speculative deals toward stabilized, cash-flowing assets in diversified markets like Houston. He emphasizes the importance of learning from...

In this episode, Glen sits down with Joel Friedland to explore the power of buying real estate entirely in cash—no mortgages, no financing contingencies. Joel shares how this strategy gives investors a competitive edge by reducing risk, speeding up deals, and building stronger trust with sellers. They also discuss how all-cash acquisitions can strengthen long-term portfolio stability and investor...

In this episode, Glen sits down with Mike Zlotnik to break down where we are in the current real estate cycle—and what it means for investors. Mike shares insights on how interest rates, inflation, and capital flows shape market trends and timing. They discuss how to recognize the signals of expansion, peak, contraction, and recovery, plus practical strategies to stay profitable in uncertain times...

In this episode, Glen sits down again with cross-border CPA Kris McEvoy to unpack a critical topic for Canadian investors with U.S. properties — how to properly move money into your U.S. entity. They break down the key differences between funding as debt vs. equity, why that distinction matters for tax and structure, and what can go wrong if it’s not documented correctly. Kris shares practical exa...

In this episode, Glen Sutherland talks with Chris Prefontaine about how realtors can become key partners in sourcing seller-financed deals. Chris shares how creative financing helps sellers close faster, bypass banks, and create win-win solutions—while giving investors steady opportunities and long-term cash flow.

In this episode of Canadian Investing in the U.S., Glen Sutherland talks with Jason Law, a Canadian investor who jumped straight into U.S. real estate. Jason shares how he built a portfolio of rentals—starting with a $32K property in Erie, PA—before branching into Airbnbs near Niagara Falls. He explains the challenges, returns, and lessons learned for Canadians looking south of the border.

In this episode of Canadian Investing in the U.S., Glen Sutherland chats with Donalta Hall about her journey from an IT career in Toronto to U.S. residency through the E2 visa program. Donalta shares how short-term rentals helped her qualify, what it was like relocating her family to Alabama, and why the state is attracting more Canadian investors.

In this episode, Glen Sutherland talks with Marian Welch, a Canadian investor and creative dealmaker who turned adversity into opportunity. Marian shares how she uses strategies like rent-to-own and vendor take-back to solve problems for buyers and sellers, and how her investing journey has expanded from Canada into the U.S. and Mexico.

In this episode, Glen welcomes back Canadian CPA Kris McEvoy to unpack the hidden tax challenges Canadian investors face with U.S. real estate. They break down common pitfalls—like FIRPTA withholding, state taxes, and timing issues—and share proactive strategies to avoid surprise tax bills. From choosing the right entity setup to tracking expenses and working with the right professionals, this con...

What if you could earn steady real estate income without tenants, repairs, or property management headaches? In this episode, Glen Sutherland talks with Eddie Speed, a 45-year veteran and founder of Note School, about the power of note investing—becoming the bank instead of the landlord. Eddie shares why mortgage notes can deliver: 💸 Higher monthly cash flow 😌 Less stress and hassle 🏡 Built-in...

In this episode, Bronson Hill shares a simple framework to help passive investors vet real estate sponsors before committing capital. From assessing the market and sponsor to asking the right questions—like “What’s the biggest risk in this project?”—you’ll learn how to spot integrity, experience, and conservative underwriting. If you want to protect your capital and invest with confidence, this co...

In this episode of Canadian Investing in the US, Glen Sutherland interviews Nathan Turner, also known as “The Canadian Note Guy.” Nathan shares how he transitioned from traditional real estate to buying non-performing mortgage notes in the U.S. He explains how he works with borrowers, modifies loans, and creates returns through creative strategies. They also discuss fund management, investor relat...

In this episode of Canadian Investing in the US, Glen Sutherland welcomes back CPA Kristopher McEvoy for another installment of their monthly accounting Q&A series. Kristopher, a Canadian accountant based in Fonthill, Ontario, specializes in cross-border taxation and real estate investing. He tackles a key question from investors: when should you start using QuickBooks Online (QBO)? While newer bu...

In this episode of Canadian Investing in the US, Glen Sutherland speaks with Torrin Brauch, an American expat who relocated to Ecuador in search of a better food supply and overall quality of life. Torrin shares his journey from growing organic food on a farm in Florida to building a 17-unit eco-lodge in the Andes Mountains of Ecuador. He discusses his motivations for leaving the U.S., the process...

In this episode, Glen Sutherland reconnects with Aurelien Bonin to explore how AI and automation are transforming real estate investing. Aurelien shares how he uses tools like ChatGPT, Zapier, and N8N to streamline operations across his Canadian and U.S. portfolio, while Glen adds how he leverages AI for contract analysis and VA systems. They also dive into the limits of automation, the power of c...

In this episode of Canadian Investing in the US, Glen Sutherland welcomes back immigration attorney Mena Maimone of Maimone Legal to clarify recent misinformation circulating online about a so-called "$250 visa fee" for Canadians entering the United States. Mena explains that this is actually the Visa Integrity Fee, which applies only to new U.S. visa applications—such as E2 investor visas or stud...

In this episode, Glen Sutherland chats with Linda Holtz about her inspiring path from managing other people’s properties to co-founding M2RE (Married to Real Estate) with her husband. Linda shares how she started with single-family homes, moved into passive syndications, and then took the leap into active ownership — all while staying true to her values of transparency and relationship-building. T...

In this episode, Glen Sutherland is joined by his personal accountant, Kristopher McEvoy, a Canadian CPA specializing in cross-border taxation. Kristopher works with clients investing in U.S. real estate, as well as those relocating or expanding businesses between Canada and the U.S. The discussion centers around a frequently asked question: what’s the most efficient way for Canadians to pay thems...