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, industrial, and student-housing projects, backed by 1,300 accredited investors. Neil explains why he diversifies across asset classes—citing supply-cycle shifts, learning opportunities, and partnerships—as well as the value of publishing commercial-real-estate data to attract like-minded, analytical investors.

Later, the conversation turns to market cycles and practical indicators of when new opportunities emerge. Neil predicts that within 18 months, most U.S. metros will transition from oversupply to shortage, starting a new bullish phase. He outlines how professionals can track this shift using CoStar, Yardi, RealPage, or Hello Data, and even simple rent-growth trends above 2 percent as a signal of recovery.

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.