The Truth About Real Estate Investing... For Canadians

Why do Ontario landlords wait 7+ months for an eviction while Alberta wraps it up in 30 days? Erwin sits down with Mackenzie Wilson of SingleKey — Canada's largest tenant screening service — to expose the massive risk gap between provinces. Inside: a live AI reference-check demo, the $60K rent guarantee product, why 76% of landlords never get reference calls, Calgary's rezoning reversal, and why turnkey beats development in 2026. A must-listen for every Canadian real estate investor.

In this episode, we break down Canada’s rare population decline, rising unemployment, weakening income growth, and what these trends mean for housing prices, rents, and investment strategy. We also explore how inflation, interest rates, global conflicts, and political shifts are shaping capital flows—and why many investors are starting to look beyond Canada to places with stronger population and income growth.If you’re a Canadian real estate investor wondering where the market is heading next, this episode helps you skate to where the puck is going—not where it’s been.

In this episode, rent‑to‑own expert Rachel Oliver shares how real estate investing has changed — and why the traditional rent‑to‑own model no longer works in today’s market. With over 16 years of experience and nearly 1,000 deals completed, Rachel explains Rent‑to‑Own 2.0, a strategy focused on cash flow, mortgage pay‑down, and stability in flat or uncertain markets. A must‑listen for investors, first‑time buyers, and anyone navigating modern real estate.

In this episode of The Truth About Real Estate Investing, Erwin Szeto sits down with best‑selling author and veteran investor Russell Westcott for an honest conversation about market cycles, hard lessons, and survival in Canadian real estate. Russell shares his personal journey through near‑bankruptcy, health scares, and tough portfolio decisions, along with why cash flow, fundamentals, and long‑term thinking matter more than hype. They discuss Alberta vs Ontario, development realities, policy challenges, and what investors should really focus on in today’s market.

In this episode, Andy Tran breaks down what’s really happening in the Canadian real estate market in 2026 and explains why 4+1 and 6+1 properties have become the new investment sweet spot in Toronto. We discuss housing supply shortages, CMHC financing, missing‑middle housing, garden suites, and why smaller, repeatable projects are outperforming large‑scale developments. A must‑listen for investors looking to adapt and find opportunity in today’s market.

In this episode, Erwin sits down with Anderson, a professional trader who went from driving DoorDash and trading on his phone to getting paid to trade stocks, options, and futures. Anderson shares his real journey—immigrating to Canada, funding his trading account through side hustles, and learning disciplined risk management over years of hard work. They also discuss buy‑and‑hold investing, options trading for everyday people, real estate investing in Barbados, and why buying back your time matters more than chasing hype returns.

In this episode, Erwin talks with Glen Sutherland, a full-time Canadian investor actively scaling US real estate from Canada. They break down what’s working in 2026, why relying on appreciation is risky, and how experienced investors use systems, creative financing, and organization to scale remotely. A practical conversation for Canadians investing in US real estate who want real-world insight—not hype.

Rasna Arora built a $50 million real estate portfolio across 70 properties using private money, refinancing, and aggressive scaling. Then the market shifted — and everything unraveled.In this raw and honest conversation, we unpack the realities of leverage, hard money loans, refinancing risk, and what happens when trusted advisors collapse. This episode goes beyond strategy and numbers — it dives into integrity, mental health, and the true cost of scaling too fast.There’s no Lamborghini story here. Just the real truth about real estate investing in Canada — the wins, the warnings, and the lessons every investor needs to hear.

Adam Kitchener built a $14 million real estate portfolio — and then lost it after a CRA audit.In this episode, he shares the hard lessons from scaling fast, navigating tax mistakes, surviving an audit battle, and rebuilding from scratch.If you're a real estate investor, landlord, or entrepreneur in Canada, this is a cautionary story you can’t afford to miss.Connect with Adam: https://renovationsolutions.ca/

Serena Holmes shares a powerful perspective on money, mindset, and real estate investing. In this episode, she breaks down why money isn’t evil, how scarcity thinking holds investors back, and the mindset shift required to build wealth with intention and impact. A must-listen for anyone serious about financial freedom

In this episode, Erwin Szeto sits down with former corporate CFO turned personal wealth strategist, Winnie Tsang, to unpack why so many Canadian real estate investors feel stuck—and what smarter, more resilient wealth planning actually looks like today. They dive into landlord challenges, diversification beyond property, leveraging the stock market, corporate‑owned life insurance, and how families can build long‑term financial security without sacrificing time, health, or peace of mind.

Thinking about investing in U.S. real estate as a Canadian? In this episode, Scott Dillingham shares the real truth about cross-border real estate investing — from mortgages and financing challenges to tariffs, hidden costs, and lifestyle impacts. A must-listen for Canadian investors exploring the U.S. market.

Mike Rosehart shares his real estate journey from buying his first student rental while in university to scaling hundreds of units across residential, hotels, and motels in Canada. We talk house hacking, leverage, market timing, selling at the peak, and why hotels and motel conversions offer massive opportunities today. A raw, numbers-driven conversation on what actually works in real estate investing.Listeners can connect with Mike at:

Canadian real estate investor Thomas Lorini joins Erwin Szeto to reveal how Canadians can break into the US property market. From overcoming financing and legal hurdles to building wealth in Ohio multifamily real estate, Thomas shares practical tips, landlord strategies, and his coaching journey. Perfect for anyone curious about cross-border investing, landlord rights, and scaling up in real estate.

Discover how to sell a tenanted property in 2026! Investor and property manager Tim Hong joins host Erwin Szeto to break down market trends, new regulations, and practical strategies for selling with tenants in place. Get expert tips on maximizing your investment, navigating challenges, and making smart decisions in today’s real estate market.Plus, get a sneak peek into the upcoming FREE webinar: "How to Sell an Investment Property for Maximum ROI" on January 13th, 8 p.m. EST.

Discover how Ontario’s Bill 60 is reshaping rental laws for landlords and tenants. Host Erwin Szeto breaks down the key changes, including lease expiry rules, eviction timelines, and new protections for property owners. Tune in for practical insights and expert advice on navigating the evolving real estate landscape in Canada.

Learn how Canadian developers and real estate leaders are unlocking government grants, building affordable housing, and driving innovation. Chelsey Fawcett shares practical tips and inspiring stories from the front lines of real estate and community development.

Thinking about investing or moving to the U.S.?

Real estate coach Elizabeth Kelly joins Erwin Szeto for a candid conversation on surviving and thriving in the 2025 Canadian real estate market. From government financing and cash flow challenges to the importance of education, mindset, and adapting your investment strategy, this episode delivers practical advice, honest stories, and actionable insights for investors at any stage.Ready to rethink your approach to real estate and wealth building? Tune in for lessons learned, market trends, and strategies that work now.

How do top investors thrive in Canada’s real estate market? Alfonso Cuadra reveals why multifamily wins, the dangers of private lending, and how to hedge against inflation. Learn strategies for scaling, financing, and surviving market shifts—plus the truth about equity vs. debt.