This episode covers a broad array of strategies for making money in real estate, offering insights for individuals at various experience levels. Here’s a summary of key points and approaches mentioned:

Entry-Level Approaches

Bird-Dogging: Identifying neglected properties for potential investors.
Boots on the Ground: Assisting remote investors by taking photos or performing on-site tasks.
Networking: Attending meetups to connect with experienced investors for mentorship and collaboration.

Creative Financing and Active Investment Strategies

Lease Options: Renting with an option to purchase for cash flow generation.
BRRRR Strategy: Buy, Rehab, Rent, Refinance, Repeat, to scale a portfolio.
Wholesaling: Securing properties under contract and selling them to other investors for a fee.

Passive Income Opportunities

Private Lending: Offering loans secured by real estate to earn interest and points.
Joint Ventures: Partnering as a passive investor to fund projects in exchange for profit-sharing.
REITs: Investing in Real Estate Investment Trusts for indirect property exposure.

Specialized Roles

Asset Manager: Managing property managers to ensure efficiency and accountability.
Key Principal: Signing for loans on large projects, leveraging personal net worth.
Real Estate Agent/Broker: Facilitating property transactions for commissions.
Promissory Notes: Lending via promissory notes secured against properties.

Real Estate-Related Businesses

Home Services: Running companies that offer services like repairs, maintenance, or cleaning.
Teaching: Sharing expertise through courses (while emphasizing credibility).

Holding and Appreciation

Simply owning a home or property generates wealth through appreciation, inflation advantages, and principal repayment over time.

Key Advice and Best Practices

Reputation Matters: Avoid promoting products or services solely for commissions if they lack quality.
Start Now: The best time to invest in real estate is always today, as holding properties over the long term builds wealth.
Do Due Diligence: Whether it’s teaching programs, lending, or entering partnerships, research thoroughly.
If you’d like to dive deeper into any of these strategies or explore how to apply them to your portfolio, let me know!

EP170 What are the Many Ways to Generate Income with Real Estate

In this episode of "Canadian Investing in the US," host Glen Sutherland interviews Brett Henry, a real estate broker in the Dominican Republic. 

Originally from Saskatchewan, Canada, Brett transitioned from a 20-year career as a police officer to becoming a successful entrepreneur in real estate. 

He shares his journey of moving to the Dominican Republic after investing in a bar, which eventually led him to explore opportunities in real estate.

Brett discusses the unique real estate landscape in the Dominican Republic, emphasizing the importance of having a knowledgeable broker due to the lack of a centralized MLS system. 

He co-founded his brokerage, RealtordR.com, with a focus on quality marketing and providing up-to-date listings to cater to Canadian and American buyers. 

Brett highlights the economic advantages of investing in the Dominican Republic, including the country's stability, safety, and the rights of foreign investors to own property outright.

Throughout the conversation, Brett touches on various topics, such as the appeal of the north coast of the Dominican Republic, the vibrant expat community, and the country's diverse economy, which includes gold mining and agriculture.

 He explains the process of obtaining mortgages in the DR, noting that while financing is available, substantial down payments are required.

Brett also shares insights into the local culture, the benefits of living in the Dominican Republic, and the potential for profitable rental income through short-term rentals like Airbnb.

 He encourages listeners to consider the lifestyle advantages of moving to the DR, emphasizing the friendly atmosphere and low cost of living.

In closing, Brett invites those interested in exploring real estate opportunities in the Dominican Republic to reach out, providing his contact information and encouraging potential investors to experience the region for themselves.

EP371 Investing in the Dominican Republic- Insights from Real Estate Broker Brett Henry

In this conversation, Brady shares the powerful mindset shift that helped him level up: you're either learning or earning, but rarely both at once. 

He explains that growth often comes through discomfort, whether it’s financial loss, stress, or failure. The key is to not quit during the learning phase, as that’s what ultimately leads to the big wins. Drawing from his experience in real estate, Brady describes how he built his skills by severing large lots in Ontario and navigating local zoning codes — a practice that later scaled into high-profit land entitlement deals across the U.S. through his company, The Barefoot Land Co., which focuses on sourcing undervalued land and securing zoning approvals for self-storage developments. 

He emphasizes the transferability of skills: the same zoning principles that yielded $200K deals in Canada can produce million-dollar profits in the U.S. if applied correctly. The final part of the discussion focuses on execution. Brady stresses that many real estate investors fail because they act like hobbyists, not operators — they lack systems, teams, and processes. To help others avoid that fate, he runs a free weekly accountability huddle called “0 to 100,” where aspiring investors can stay consistent, ask questions, and build alongside others. 

He encourages people to start small, build foundational knowledge, and surround themselves with a community of doers to accelerate growth and stay accountable.

EP372 You're Either Learning or Earning The Hard Truth About Building Wealth w Brady McDonald

In this insightful podcast interview, Glen speaks with experts about the E2 visa process, offering invaluable advice for Canadians interested in launching or expanding their businesses in the U.S. They delve into key topics such as the essential elements of a successful business plan, the importance of creating jobs, and the flexibility of the E2 visa for those looking to buy or build businesses across various industries. From property management to consulting firms, the conversation highlights the diverse opportunities available, including the option to bring essential employees from Canada. They also tackle common concerns about U.S. immigration and the border process, offering reassurance to Canadians considering the E2 route. Whether you're thinking of relocating or running a business remotely, this episode provides crucial insights for anyone looking to navigate the U.S. business landscape through the E2 visa.

EP373 E2 Visa Secrets How Canadians Can Build a Thriving U.S. Business Filomena Maimone

In this episode, Glen Sutherland and Kristopher McEvoy dive into the potential impact of proposed U.S. tax legislation on Canadian investors with U.S. assets. They discuss why proper investment structuring is more important than ever, the risks of increased withholding taxes, and how treaty changes could affect future returns. Kristopher shares why working with cross-border tax professionals is essential and offers practical strategies to help Canadians stay compliant, tax-efficient, and prepared for international policy shifts.

EP374 The Big Beautiful Bill What U.S. Tax Changes Mean for Canadian Investors Kristopher McEvoy

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.

EP393 Sending Money to U.S. Entities What Canadian Investors Must Know with Kris McEvoy (1)

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.

EP394 Where Are We in the Real Estate Cycle with Mike Zlotnik

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.

EP395 Buying Assets All-Cash and No Mortgage with Joel Friedland

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.”

EP396 Creative Strategies for Today’s Real Estate Market with Patrick Grimes

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.

EP397 New Chapter for Cross-Border Investors- Expanding Cross-Border Tax Support w Kris McEvoy & Tim Miron

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.

EP170 What are the Many Ways to Generate Income with Real Estate

The Real Estate Round Table