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

EP375 The Remote Real Estate Investor with Steve Pletz

Glen Sutherland welcomes back Marcin Drozdz to share how his U.S. real estate journey has grown since his earlier appearances. Marcin talks about his shift from single-family homes to larger commercial deals, including industrial and multifamily properties. He shares valuable lessons on partnerships, deal structures, lender challenges, and the importance of staying flexible.

The episode also dives into mindset, risk, and how building the right network can accelerate success. Marcin explains how taking action—even when things aren’t perfect—can lead to incredible growth and opportunities.

A must-listen for Canadian investors exploring U.S. real estate!

EP376 The Mindset Shift Behind Marcin Drozdz’s Real Estate Success

In this episode, Glen Sutherland chats with Lindsey Davis, CEO of Spartan Invest, about why Alabama is becoming a prime rental market for out-of-state and international investors. Lindsey explains how Alabama’s low property taxes, landlord-friendly laws, and affordable turnkey properties create an ideal environment for real estate investors.

They also dive into the state’s strong economy, population growth, and how Spartan Invest’s full-service model offers a truly hands-off experience. If you're looking for cash flow and long-term stability in the U.S. market, this episode is packed with valuable insights.

🎧 Tune in now to discover why Alabama might be your next great investment opportunity.

EP377 What Canadian Investors Need to Know About Alabama Real Estate with Lindsay Davis

In this episode, Glen Sutherland talks with financial advisor and author John De Goey about how common behavioral biases—like confirmation bias, loss aversion, and overconfidence—can quietly influence our money choices. John shares real-life examples and practical tips to help investors become more self-aware and make smarter financial decisions.

Learn how your mindset might be shaping your financial future more than you realize.

EP378 Phychological Vices that Keep Most People Repeating Bad Wealth Decisions w John De Goey

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

EP380 How One Girls’ Trip to Cancun Sparked a Real Estate Empire with Linda Holtz

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)

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

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