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 business

Nathan 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.

🎯 If you're looking for practical wholesaling insights without the “get rich quick” pitch, this episode’s for you.

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 markets

• Why technology and data are changing the game in real estate
  

• The real story behind turnkey rentals and institutional landlords
  

• Tips on navigating taxes, financing, and management across borders
  

Whether 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.