The Truth About Real Estate Investing... For Canadians

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.

Luis Rivas shares how he left a 22-year government career, cashed out his pension, and pivoted into real estate investing and coaching. From the fear of leaving “golden handcuffs” to building wealth through multifamily properties, private lending, and U.S. opportunities, Luis dives into pensions, Canada’s economy, AI’s impact, and creating financial freedom on your own terms.

From family crisis to financial freedom — this is the inspiring journey of Arminda Simao, a single mom who built stability through student rental investing.She opens up about balancing kids’ expensive tuition, losing her husband, and how smart real estate choices created cash flow, resilience, and generational wealth.

In this episode, Erwin Szeto talks with Jimmy La & Kartik Singla (SDG Canada) about their Clapperton Village project in Barrie and how they’re reshaping rental housing with modular builds, multi-generational units, and CMHC’s MLI Select financing.Plus, a preview of the Missing Middle Conference in Toronto.

Ontario’s small landlords are struggling with LTB delays, tenant fraud, and rising risks. Host Erwin Szeto talks with Boubah, co-founder of SOLO.ca, about how a grassroots movement of nearly 9,000 members is supporting landlords, pushing for fair reforms, and fighting back against a broken system.

From early investing mistakes to building 5 duplexes, a luxury ski chalet, and breaking ground on a commercial development, Brad shares his journey through real estate’s ups and downs. Learn how he scaled fast, mastered short-term rental math, and shifted to complex strategies in today’s market. Packed with tips on location, scarcity, and building wealth with hard, scarce assets.You can follow Brad’s weekly writing at - biggerthings.substack.com

Real estate lawyer and Cardinal Law co-founder Shawn Quigg joins Erwin Szeto to expose the biggest legal risks investors face in 2025—from joint venture breakups to disastrous private lending structures. They cover real-world deal failures, the importance of contracts, how to avoid losing your property to the province, and how to properly structure deals using CMHC MLI Select, limited partnerships, and more.Whether you're a new investor or a seasoned developer, this episode is packed with essential legal insights to help you protect your capital and partnerships in today’s market.

Financial advisor Adam Niman joins Erwin Szeto to share how he turned private lending into a real estate portfolio—and the hard lessons learned along the way. Adam breaks down how he evaluates deals, handles failed loans, and why many Canadians are being misled about participating life insurance and the Infinite Banking concept.

In this mind-opening episode of The Truth About Real Estate Investing for Canadians, Erwin sits down with Andrew Kim to discuss how Share, a tech-enabled real estate asset management platform, is revolutionizing U.S. property investing for Canadians. With over 20 properties across four states, Andrew reveals how institutional-grade systems and AI-driven tools allow everyday investors to scale smartly—without the hassle of day-to-day property management.Whether you're a new investor or looking to scale beyond your first few doors, this episode is packed with practical insights and strategies to help you navigate today’s market—on both sides of the border.Explore more:Website: www.sharefrs.com

In this episode, developer Rodney Wilts shares how he's turning contaminated land into zero-carbon housing—including the award-winning Zibi Project. From ESG-driven returns to affordable retrofits, learn how real estate can solve Canada’s housing and climate crises.

In this episode of The Truth About Real Estate Investing for Canadians, we follow the journey of Carlos Rodrigues, a former Canadian financial planner who sold off his entire Ontario real estate portfolio to start over in Cleveland, Ohio. Carlos shares the real story—including the $30K he lost to a shady property manager, the challenges of lead paint certification and evictions, and how he uses DSCR financing to invest without personal income.

This week on The Truth About Real Estate Investing for Canadians, I’m joined by Nathan Payne, founder of Painless Flipping—and no, that’s not just a clever name. Nathan’s a full-time real estate wholesaler who runs his entire U.S.-based business virtually… from small-town Ontario, Canada.We get into: ✅ How he wholesales houses without ever meeting sellers in person ✅ His pivot during COVID that expanded his business nationwide ✅ Why he prefers wholesaling in the U.S. over Canada (spoiler: faster evictions, better cash flow, and yes—fewer meth labs) ✅ The truth behind wholesaling income claims, guru coaching fluff, and what new investors are getting wrong ✅ His hands-on apprenticeship model—a no-fluff, partner-on-deals approach to learning the businessNathan doesn’t just talk about values—he lives them. From faith, family, and integrity-first investing, to feeding missionaries and knocking doors in rural Ontario during a snowstorm... This guy walks the walk.

I’m thrilled to have Tony Irwin on the show today. Tony is the President and CEO of both the Canadian Federation of Apartment Associations (CFAA) and the Federation of Rental Housing Providers of Ontario (FRPO)—two of the largest organizations advocating for landlords and rental housing providers at the provincial and national levels.With years of experience in policy, government relations, and housing advocacy, Tony is at the forefront of the fight to protect landlords, encourage rental supply, and push back against policies that make it harder to provide housing.If you own rental properties or are thinking about investing, this is a must-listen episode. The policies being decided today will impact your bottom line for years to come!

Are you a Canadian investor struggling with low cash flow, rent control, or expensive renovations? In this episode, we sit down with Ben Barry, a U.S. real estate expert who's deployed over $2 billion in capital and helped transform how investors like you succeed south of the border. What You’ll Learn:How Canadian investors can tap into high-yield U.S. rental marketsWhy technology and data are changing the game in real estateThe real story behind turnkey rentals and institutional landlordsTips on navigating taxes, financing, and management across bordersWhether you're fed up with Ontario's eviction delays or you're just curious about basement conversions vs. single-family rentals, this is your roadmap to smarter investing.

Hey friends, this is Erwin Szeto, and welcome to The Truth About Real Estate Investing for Canadians, where it’s my job to interview the top minds in real estate and business to uncover the strategies, mindsets, and habits that actually work—especially in today’s market. My guest today is Michael Ponte—a full-time real estate investor, educator, and co-founder of Savvy Investor. He’s been investing for more than 20 years and owns a multi-provincial portfolio that spans Alberta, BC, and Atlantic Canada. He’s raised capital, survived multiple recessions, and built a strategy around what he calls “lazy investing”—focused on cash flow, simplicity, and long-term success. In this episode, we get into: Why he avoids over-leveraged strategies like promissory notes and MLI Select What it’s like to refinance and pull nearly $1 million out of a property And how he built a business around student rentals, multi-family units, and zero tolerance for rent control Also—Michael is hosting a free virtual boot camp on May 3rd

Greetings friends, this is Erwin Szeto, and welcome to The Truth About Real Estate Investing for Canadians, the #9 ranked podcast for Canadian Investment and Personal Finance per FeedSpot! Thank you listeners and past guests of this show! As always it’s a honour to have this platform and ability to give back to the community that has been so much to my family and I where we all share a passion for the best investment class in the world: real estate.  Here on this show, it’s my job to interview the top minds in real estate investing and business to uncover the strategies, mindsets, and habits that actually work—especially in today’s market. This week’s guest is Scott Dillingham, founder of LendCity Mortgages, is returning to the show with a mortgage market update!  He is a rare expert in both Canadian and U.S. real estate financing. Scott built his career helping investors—starting as a high-volume mortgage broker at one of Canada’s Big Four banks for ten years, where he consistently ranked among the top 1% na