From Broke Student to Real Estate Mogul: Jeffrey Woods' Journey & US Investing Tips

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Jeffrey Woods, a seasoned real estate investor who has been full-time in the industry since 1998. Jeffrey shares his origins as a struggling college student in Ontario, Canada, saving up to purchase his first distressed property—a bank power of sale in Hamilton. He discusses early successes renting rooms to students for positive cash flow, followed by hard lessons from a problematic second property involving bad tenants, fire code issues, and landlord-tenant board challenges. Emphasizing the importance of education and mentorship, Jeffrey explains how he scaled his portfolio beyond 150 doors in the Hamilton and Niagara regions through strategies like the BRRRR method, joint ventures, and private lending.

Transitioning from single-family homes to multifamily and commercial deals, Jeffrey highlights the role of partnerships in rapid growth, achieving his goal of 100 units in under six years. He candidly addresses challenges like vetting partners, managing contractors, and navigating tenant issues, stressing clear communication and alignment on long-term holds. As Canadian real estate faces hurdles like rising costs, rent controls, and lengthy evictions (often 8-18 months in Ontario), Jeffrey pivots to international opportunities. He details his move to the Dominican Republic in 2021 for a semi-retired lifestyle, appreciating its beaches, culture, and affordability, though noting limited scalability for large portfolios compared to the US.

Now focusing on landlord-friendly US markets, Jeffrey targets North Carolina (especially Charlotte) and Atlanta, Georgia, for their economic growth, stable climates, and investor advantages like 30-year fixed mortgages, no rent caps, and quick evictions (often under 30 days). As of November 2025, Charlotte's housing market shows balance with median home prices around $394,339 (down 1.4% year-over-year) and active listings up 24% to about 4,800, the healthiest supply in nearly a decade. Atlanta's market reflects a buyer's shift with median prices at $400,000 (down 3.6%) and homes lingering 82 days on average. In the Dominican Republic, 2025 projections anticipate 12 million tourists, boosting rental opportunities, though the market suits lifestyle investors more than aggressive scalers. This episode delivers actionable insights for building wealth through real estate, blending personal anecdotes with strategic advice for aspiring investors.