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. She shares examples of clients with vastly different goals, from relocating overseas to buying a first home or going back to school, emphasizing that understanding what matters most to each person drives the right financial and investment strategies. The conversation then dives into tax planning—a subject many people only think about when faced with a large bill. Priscilla stresses that effective tax planning must be proactive, not reactive, and should begin now, regardless of the time of year. She encourages investors to build an “A-Team” of professionals—financial planner, CPA, and attorney—who collaborate to design forward-looking strategies that balance current actions with future goals. She also offers practical advice on how to prepare for planning meetings, such as bringing an overview of assets, account types, and investment values. The episode closes with a thought-provoking reminder: financial planning should start with your end goal in mind—how you want to be remembered and what legacy you want to leave behind—and then reverse-engineer your path toward that vision.

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 the GTA and Niagara regions to access the same cross-border tax expertise more conveniently, while maintaining continuity of service. Tim highlights that his firm already handles numerous U.S.-related corporate structures and cross-border clients, ensuring that the expertise LEAP ACT clients rely on will remain in place. Chris also announces his departure from LEAP ACT to join a technology company as an executive officer, a longtime client that recently achieved significant scientific breakthroughs and funding. He expresses confidence in Tim’s leadership and notes that key relationships with partners like Global Tax Services (Ali Ajami) and cross-border legal collaborators will remain intact. The group discusses how the transition will strengthen service delivery and maintain collaboration between Canadian and U.S. advisors. Chris thanks Glen and the investing community for their support and shares plans to become more active personally in real-estate investing, coming full circle from accountant to investor. Glen closes by expressing excitement for the transition and the continued partnership with the expanded Pursuit-LEAP team.

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 failure, studying how the wealthy allocate capital, and building portfolios that can withstand economic downturns through diversification across asset classes and industries. Today, Patrick leads Passive Investing Mastery, a platform educating investors on more than 50 types of alternative investments beyond the stock market—from private credit and legal funds to industrial and healthcare opportunities. He advocates blending non-correlated assets such as real estate, energy, and precious metals to protect and grow wealth regardless of market cycles. As Patrick notes, “The best time to diversify was two years ago. The second best time is today.”

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 confidence. In uncertain markets, this episode reveals why sometimes the safest move is the smartest one.

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—like diversifying assets, stress-testing deals, and focusing on cash flow. Whether you’re a seasoned investor or just getting started, this episode will help you think strategically, stay flexible, and make smarter moves through every market phase.

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 examples, planning tips, and best practices for keeping your contributions clean, compliant, and strategically sound. Whether you’re wiring funds for your first deal or restructuring an existing portfolio, this conversation will help you avoid costly mistakes and stay on the right side of both tax and legal requirements.

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 conversation highlights how smart planning can protect profits in cross-border investing.

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 equity cushion You’ll also learn how to properly underwrite deals, manage risk, and use professional servicers to handle payments, defaults, and even foreclosures. With decades of experience, Eddie shows how investors can create passive income and long-term wealth with confidence.

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 conversation is a must-listen.

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 relations, due diligence, and the advantages of note investing—like lower costs and less hands-on work compared to rentals. Glen and Nathan reflect on key lessons around partnerships, focus, and building long-term momentum.

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 buy-and-hold investors may get by with spreadsheets initially, Kristopher explains that investors with more complex operations—like flips or BRRRRs—need proper systems early on to track profitability and stay tax-compliant. Kristopher emphasizes that accounting software like QBO not only helps with tax filing but also enables better business management through automation, delegation, and financial reporting. He highlights the unique nuances of real estate bookkeeping, such as capitalizing interest during renovations and correctly categorizing repairs vs. improvements. For growing investors, Kristopher’s firm, LEAP ACT, offers flat-fee bookkeeping services that scale with volume, making it especially valuable for those managing multiple deals. Listeners can connect with him at leapACT.ca and are encouraged to mention the podcast when reaching out.

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 of buying his first property within days of arriving, and how Ecuador’s low property taxes, favorable climate, and structured property registry system made it a compelling place to settle and invest. Torrin now operates a hospitality and real estate development business under the banner Live the Life in Ecuador, offering seller-financed lots, sustainable housing, and relocation support for foreigners. He walks listeners through the logistics of buying property, visa options, and the legal framework for ownership and financing in Ecuador. Torrin also highlights the lifestyle benefits, including clean air, fresh food from community food forests, and a welcoming local culture. Interested visitors can learn more or arrange a stay through his website, livethelifeinecuador.com.

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 collaboration, and their joint efforts on multifamily deals. A must-listen for investors looking to scale smarter!

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 student visas—and has recently increased from $250 to $500. It does not affect Canadians traveling as visitors for shopping, vacations, or short business trips, nor does it impact those who already hold valid visas until they renew. The discussion highlights how social media has distorted the facts, leading many to believe the fee applies at the border to all travelers. The conversation also addresses rumors that Canadians are being detained or deported in large numbers when entering the U.S. Mena confirms these claims are unfounded, noting that any detentions are typically tied to legitimate issues such as criminal history or security concerns. She suggests that fear-driven narratives may be partly motivated by concern over the increasing number of Canadians—especially high-income earners and investors—moving south for business and lifestyle opportunities. Both Glen and Mena encourage listeners to seek accurate, professional advice rather than rely on online hearsay, assuring that cross-border travel and investment remain accessible and safe for most Canadians.

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. They also talk about how she met her husband (thanks to his mom on a girls’ trip!) and how their shared background in property management became the foundation for their business. 🎧 Key takeaways: ✔️ Start small and grow with experience ✔️ Why honesty builds trust with investors ✔️ The power of complementary skills in a partnership

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 themselves from their U.S. real estate or business income? Kristopher explains that the answer depends on the ownership structure: If using a U.S. Limited Partnership (LP): You’re taxed annually on profits—not on withdrawals—so taking money out has no further tax consequences. If using a U.S. Corporation: Paying yourself personally via dividends or payroll can be highly tax inefficient, with a potential combined tax burden of up to 50–60%. A more efficient strategy involves using a Canadian corporation to own the U.S. corporation, enabling: Management fees Interest charges Intercompany dividends (typically subject to only 5% U.S. withholding tax under the current tax treaty)