In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Tom McCormick, a mechanical aerospace engineer turned real estate investor from Windsor, Ontario. Tom shares his entry into real estate during the 2020 COVID era, motivated by job uncertainty and inspired by his brother's duplex purchase near the University of Windsor. Starting with a challenging single-family home converted into an additional dwelling unit (ADU), Tom discusses the sweat equity, city code navigation, and lessons from gutting the property to the studs. He highlights how his engineering background aided in understanding building requirements, and credits his father as his first investor for providing capital to complete the basement unit and achieve cash flow.
Transitioning to U.S. investments, Tom explains leveraging his work experience in the States since 2017, including building U.S. credit, SSN, and bank accounts. He contrasts Canadian and U.S. markets, noting lower taxes, cheaper per-door costs, and more landlord-friendly laws in the U.S. as key drivers. Detailing a Detroit flip project financed through LendCity, Tom describes acquiring a dilapidated North End property for $75,000 USD with a $100,000 renovation budget, facing hurdles like an "upside down loan" where renos exceed purchase price. Renovations include structural fixes, adding a bathroom for a 4-bed, 3-bath layout, electrical rewiring, and preserving classic Detroit wood features. With an after-repair value (ARV) projected at $260,000–$270,000 USD, potentially higher in spring 2026, Tom emphasizes conservative planning and partnership models.
Tom debunks Detroit's outdated stigma, praising its vibrant downtown and safety improvements, making it an ideal backyard opportunity for Windsor investors. He outlines future projects, from quick flips to larger 8-12 unit multifamily rehabs aiming for the 1% rule on returns. Stressing action over perfection and "failing forward," this episode provides actionable insights for Canadians eyeing U.S. real estate, blending personal anecdotes with practical strategies for cross-border success amid ongoing market stability in Detroit as of November 2025.
Key Takeaways
- Engineering Roots to Real Estate: Tom's aerospace engineering degree from University of Windsor and automotive career provided skills for navigating building codes and renovations, starting with a 2020 single-family ADU conversion involving full gutting and sweat equity.
- First Deal Lessons: Bought a challenging property, ran out of funds mid-project, and secured father as investor; emphasized failing forward and self-education on city requirements for future confidence in flips.
- Cross-Border Shift Motivations: Since working in the U.S. from 2017, Tom built credit and accounts; prefers U.S. for lower taxes, cheaper properties (about two-thirds Canadian prices per door), and easier tenant management.
- Detroit Flip Details: Acquired $75K North End property (C-class area gentrifying); $100K renos include structural joist sistering (~$15K), new bathroom, open-concept kitchen, full electrical rewiring, and wood preservation for classic appeal.
- Financing Challenges and Wins: Overcame "upside down loan" issues with LendCity's help; projected ARV $260K–$270K USD, targeting Easter 2026 completion and spring sale for healthy profits.
- Partnership Model: Uses 50/50 splits for flips and multifamily; seeks partners for quick 6-month returns on flips or longer 1+ year stabilizations on 8-12 plexes hitting 1% rule; stresses skin in the game for fairness.
- Detroit Market Outlook 2025: Highlights improved safety, vibrant downtown, and value over Windsor equivalents; advises focusing on numbers and market fundamentals for cross-border deals.
Links to Show References
- Tom McCormick's Contact: Facebook/YouTube - Search for Tom McCormick; Linktree - linktr.ee/tommccormickrealestate (verified active as of November 2025)
- LendCity Mortgages (for U.S. Financing and Pre-Approvals): lendcity.ca
- University of Windsor (Tom's Alma Mater): uwindsor.ca
- Detroit Real Estate Resources: For market updates, check detroitmi.gov or local MLS listings
- (00:08) - Introduction to the Podcast
- (01:27) - Tom's Journey into Real Estate
- (04:09) - Investing Across the Border
- (05:59) - Navigating the U.S. Market
- (14:39) - The Detroit Flip Project
- (18:20) - Future Partnerships and Opportunities
