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From Windsor to Wealth: Tom McCormick's Real Estate Adventure into the United States


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In this episode, Scott interviews Tom McCormick, a Canadian investor who successfully transitioned from investing in Windsor to flipping properties in Detroit. Tom shares his engineering background, initial property ventures, and how he navigated the challenges of cross-border investments.

Key Timestamps:
[0:00] Introduction and Guest Background
- Tom's journey into real estate during COVID-19
- From automotive engineering to property investing
- How his brother inspired his first investment

[4:30] 🏠 First Real Estate Purchase
- Creating an additional dwelling unit (ADU)
- Learning through "failing forward"
- Sweat equity and financing challenges
- Scott shares his similar first investment experience

[10:15] 🌎 Transition to U.S. Market Investing
- Advantages of working in the U.S. before investing
- Building U.S. credit history and obtaining SSN
- Comparing Canadian vs. U.S. real estate markets
- Overcoming fears of cross-border investing

[15:45] 🔨 Detroit Property Flip Case Study
- Purchasing a $75,000 property in Detroit's North End
- Managing an "upside-down loan" with higher renovation costs
- Detailed renovation budget breakdown
- Expected ARV of $260,000-$270,000

[20:30] 💰 Partnership Structure and Future Projects
- 50/50 split with investors
- Balancing capital contributions
- Upcoming opportunities: 8-plexes and 12-plexes
- Short-term flips vs. long-term buy-and-hold strategies

Key Concepts Covered:

Cross-Border Investment Advantages:
- U.S. dollar earning potential (30% "raise" through exchange rate)
- Lower price per door compared to Canadian markets
- Different landlord-tenant laws
- Gentrification opportunities in emerging neighborhoods

Detroit Market Specifics:
- C neighborhoods on the cusp of becoming B neighborhoods
- Preserving classic Detroit architectural features
- Balancing modern renovations with historical character
- Managing expectations for selling timeframes (2-month market time)

Property Acquisition & Renovation Strategy:
- Identifying structurally challenged properties at discount
- Strategic improvements for maximum ROI
- Renovation breakdown: structural repairs, electrical rewiring, bathroom additions
- Preserving original wood features for market appeal

Partnership Model:
- Equal skin in the game philosophy (50/50 splits)
- Division of responsibilities (management vs. capital)
- Building long-term relationships for multiple deals
- Leveraging financing to reduce capital requirements

Investment Timeline Examples:
- 4-5 month renovation timeframe
- 6-month total project cycle for flips
- Longer-term (12+ months) for multifamily stabilization

Financing Challenges:
- Managing upside-down loans (renovations exceeding purchase price)
- Lender hesitation with Detroit market
- Importance of building track record for better terms
- Balancing investor capital with financing

Real World Numbers:
- $75,000 purchase price
- $100,000 renovation budget
- $260,000-$270,000 projected ARV
- Potential for higher returns based on market timing (spring selling season)

Resources Mentioned:
- Tom's social media presence on Facebook
- Tom's YouTube channel
- Upcoming link tree for direct connections

Important Note:
Before investing across borders, consider setting up proper legal entities, understanding market fundamentals, and potentially partnering

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The Wisdom, Lifestyle, Money, ShowBy Scott Dillingham