The Truth About Financial Independence for Canadians

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.

🎯If you're a frustrated Canadian landlord looking for cash flow, control, and freedom in the U.S. market, this episode is your roadmap.

📚 Grab his book Property Profits on Amazon
📱 Follow him on Instagram: @cashflowcarlos

🎧 Tune in now for the unfiltered truth about U.S. real estate investing as a Canadian.

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.

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.

In today’s episode, I’m joined by Ben Berry, a true industry heavyweight who's successfully deployed over $2 billion into single-family rentals, build-to-rent, and commercial real estate assets. Ben’s journey began during the depths of the 2009 global financial crisis, where he carved out his path in commercial real estate before pioneering large-scale single-family home acquisitions during the U.S. housing recovery. His leadership helped operationalize the mass acquisition, rehab, and management of thousands of homes backed by major Wall Street and Canadian institutional investors.

Now, Ben is the Vice President of Acquisitions and Sales at SHARE, a platform revolutionizing real estate investing by making U.S. rental property ownership simple, passive, and accessible — even to everyday Canadian investors. With boots-on-the-ground expertise across over 20 markets — from Florida to Texas, Georgia, North Carolina, Ohio, etc… — Ben shares how institutional best practices are now being offered without the need to bring $50M to the table.

We also talk about why landlord-friendly states matter, how technology and data have transformed real estate investing, and how Canadians now invest just like the ultra wealthy and finally escape tenant friendly markets and find deals that actually make sense. If you're serious about investing smarter in real estate, this episode is a must-listen.

If you’d like to connect with Ben you can go to iwin.sharesfr.com and click the “Schedule a call” 

Please enjoy the show!

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, and I’ll be one of the speakers. It’s called The Savvy Investor Boot Camp, and it covers everything from BRRRRs to private lending to U.S. investing. You can register at thesavvyinvestor.ca -- again, it’s completely free.

Now, please enjoy my conversation with Michael Ponte.

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% nationwide. In his peak year, he closed over 410 mortgage deals, most of them for investment properties.

He’s also a seasoned real estate investor himself, owning dozens of rental units, which gives him firsthand insight into the challenges his clients face.

What makes Scott especially unique is that, as a dual citizen, he’s able to own and operate mortgage brokerages in both Canada and the U.S.—something rare, I don’t know anyone else who can do that. That means Canadian investors working with Scott can access lending strategies, mortgage approvals, and support for properties on both sides of the border—all under one team.

Through LendCity, Scott works with over 60 lenders in Canada and 2,500+ lending sources in the U.S., helping investors scale smarter no matter where they’re buying.

📍Catch him live Saturday morning April 26th Half-Day iWIN Meeting. We have in person seats which are almost sold out and a bit of room online for those who live a bit further away. We survey our subscribers and you want to hear about landlord friendly strategies: student rentals, short term rentals and the US and that’s what you’ll get!  My team and I will be sharing a local real estate market update including rentals, tips on selling tenanted properties and Scott will be live and in person where he’ll share best practices on financing and navigating both Canadian and U.S. lending markets.

🎟️ Register here: https://iwinmeeting.eventbrite.ca/?aff=ig

Please enjoy the show!

✅ The current state of Ontario and Canada’s rental markets ✅ Why rent control and landlord-tenant board delays are making investing more challenging ✅ What landlords can do to get involved and protect their investments

Welcome back to The Truth About Real Estate Investing for Canadians! I’m your host, Erwin Szeto, and today we’re diving into one of the most important conversations for landlords and real estate investors—who’s actually fighting for us?

Between rising costs, rent control, landlord-tenant board delays, and policy changes that make it harder to operate rental properties, it’s no surprise that many landlords feel like they’re being left behind. But there are people advocating for us, working behind the scenes to shape fair policies and ensure that rental housing remains a viable investment.

That’s why 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.

In this episode, we get into: ✅ The current state of Ontario and Canada’s rental markets ✅ Why rent control and landlord-tenant board delays are making investing more challenging ✅ What CFAA and FRPO are doing to push for fairer policies ✅ What landlords can do to get involved and protect their investments

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!

Tony’s contact information:

FRPO: https://frpo.org

CFAA: https://cfaa-fcapi.org

Instagram: @frpofacts

 ✅ Understand why investors are shifting to U.S. markets ✅ Learn how to raise capital and structure bigger deals ✅ Hear what it takes to put 5,000 investors in a room with A-listers

Ever wonder what it takes to build Canada’s biggest investing conference?

My old friend Seth Ferguson, returns to the show, after losing all his rental properties to a nasty divorce along with his golf clubs, he started the Multifamily Conference in Covid in 2022 which was excellent, 2023 was headlined by Grant Cardone & Alex Rodriguez, 2024 Wolf of Wall Street Jordan Belfort and Robert Harjevic.  Today, Seth takes us behind the scenes of how he scaled from a couple hundred person real estate event into a 5,000-attendee juggernaut, easily Canada’s largest Business & Investment event. With speakers like Kevin O’Leary, A-Rod, Dragons Dens: Michelle Romanow, and Manjit Minhas, and still another major speaker yet to be announced. Powerhouse is an apt name for the event.  Same for the budget!

We dive into marketing, event growth, and how Seth landed some of the biggest names in business. For details and to register go to: https://powerhouseconference.com/

The event takes place May 23-25th in Toronto.

We also get into Seth’s own real estate portfolio and his shift away from Canadian rentals to focus exclusively on multifamily investments in landlord-friendly U.S. markets like Texas and Florida.

Seth and his team specialize in garden-style multifamily properties—low-rise, landscaped apartment communities that are common in the U.S. but virtually unheard of in Canada, where high-rise towers dominate. He shares what makes these assets so attractive, how they’re managed, and why he’s also drawn to build-to-rent communities and why he’s bullish in places like Florida and Texas. For details check out www.cpicapital.ca

It’s not all bad 🙂

Thank you to everyone who took time out of their busy schedules to wish me a happy birthday. The vast majority of messages came from the real estate investing community, and reading all the comments and seeing the names brought back a lot of memories—many from easier times for real estate investors.

My fellow escape-room-loving, nerdy friends attempted to be among the elite 4% who successfully escape... #FAIL

This mango cake tasted better than it looks

Since the peak of the market around late 2021 to early 2022, prices have declined while the cost of operating a rental property has continued to rise. Rent control has squeezed landlord incomes, leaving many of my clients and fellow investors struggling. We real estate investors never signed up to backstop inflation for our customers, and not once has anyone said, "Thank you."

Some of my clients have endured nightmare tenant situations: one tenant owes over $30,000 in rent; another caused $20,000 in damages; and another had terminal health issues, not paying rent, leaving the house in such a disastrous state that it had to be sold as-is. Our client unwittingly became a social service provider overnight, and they’ll never be Ontario landlords again. Why buy and hold a move-in-ready property for ten years only to experience this kind of grief? This is not what my private citizen client signed up for.

In the areas where Ontario where majority of cash flow oriented investors invest like Oshawa, Barrie, Hamilton and Kitchener are well off their peak prices.  Duplexes especially. In Hamilton where the majority of my clients and my duplexes are located we're 20% off peak prices and we're experiencing low showing volume of our tenanted and vacant duplex listings.

Market rents are coming down on long-term rentals too as international students aren't coming to Canada in droves any more but our university (not college, we're not a fan of college student rentals) student rental rents have still climbed slightly, even over last year's historic increases.  I was finally able to get rent PLUS utilities on my McMaster University rental.  Those same tenants have already renewed for the following school year.  I feel bad for parents of university students as I review rental rates for upcoming listings we have near Brock and Western University at $700 and up per room. (Please let me know if you have anyone looking to buy a student rental near Brock and Western University :). University student rentals are my favourite local investment strategy for both cash flow and limited landlord tenant board risk.  From what I see in the local market, student rentals have the most demand from investor buyers.

This is the most buyer advantaged market I've seen other than 2008 and early covid but with the Landlord Tenant Board risk and cash flow, rents across the country are declining but not that far off historic highs, so overall housing affordability is still bad on the historic side.  So no surprise, I've never seen such low local investor buyer interest.

As such, Realtors and full time investors have returned or pursued other careers. My own team of investment focus Realtor/coaches has shrunk, it's just the original Tim Hong and I now servicing our clients and our clients mainly want to sell which is great us as Realtors, not so great is tenanted properties take a whole lot more effort, lead time and risk management in our experience but we love it.  We love seeing our clients take profits, take a load off their shoulders and enjoy themselves, usually it's travelling to exotic locations.

It's challenging but such rewarding work.

For months, we where taking calls from pre and construction condo investors but unless they wanted to take massive losses, in some case 20% or more of their purchase price as there is six months of condo supply downtown Toronto.  That's what's on market and can be tracked. I've been in the Facebook groups for private assignment sales and there are endless private listings there as well. 

Condos have always gone against my investment philosophy.  Land is a hard asset as it is finite, no one is making more of it vs. condos are in the sky and there's plenty of space above land to many, many condos.

Generally condo investors have no choice to hold, rent it out, negative cash flow a thousand or two each condo and pray the market recovers in two or three years.  I feel bad for new condo investors and at the same time, grateful our strategy of buying on land real estate for value and cash flow has worked.

In my nearly 14-year career coaching clients in real estate, I have never seen challenges like these. Thankfully, our clients have fared much better than most, as they’ve renovated smartly to optimize cash flow. Nearly all of our clients own houses with basement apartments, student rentals, or small multi-family properties.

Rents are as good as they get in Ontario, which means our clients can weather this storm better than most.

I won’t sugarcoat it—this past year has been tough for landlords, Realtors, mortgage brokers, variable-rate mortgage holders, and even tenants, as affordability is at historic lows. My family and I included.

There is bad news is all over social media, many friends from the community send me the dirt on the furus: a word mash up of fake guru and these furus have made the national news: bad operators brokering shady deals, borrowing through promissory notes, accusations of Ponzi schemes, Securities Code violations and these same furus send legal threats against anyone who dares to share the truth. I've received several threats and you can guess by who.

Some of these furus are still licensed and practicing which boggles my mind. Others have fled the country and white collar crime goes mostly unpunished so I don't expect any justice.

For anyone interested in Exposing Fraud & Failures in Canadian Real Estate, that is literally the name of a Facebook Group my new friend Matt invited me to.  You may want to join as it's an easy way to reference check anyone raising capital. Link: https://www.facebook.com/groups/588190593990235

If you’re an investor, you know that mindset is everything. The right strategy and a growth mindset separate those who thrive from those who struggle.

"Your mind is like a garden. You can grow flowers, or you can grow weeds. Whichever you water is what will flourish." — Brian Tracy

This quote is a great reminder to be intentional about a positive mindset and personal growth. Since December, I’ve been working to improve on the right mindset by waking up early, meditating, journaling, exercising, and focusing on being my best self for my family and my community.

If you’ve read The Miracle Morning by Hal Elrod (or any of the dozens of other personal development books on the subject), you know what I’m talking about. It’s amazing how much you have to say "no" to in order to be up at 5 a.m. each morning—less social media, bad food, alcohol—all to protect my energy and ensure a productive, intentional workday. Some nights I go to bed before the kids LOL.

Many investors are making the shift landlord friendly strategies like student rentals I already mentioned, there's rent to own or to landlord-friendly places like Alberta and U.S. markets, and this show is here to share such best practices, to guide you every step of the way. In my own business, we've helped nearly four dozen clients acquire or prepare to acquire income properties in these markets. These are some of the best passive investment deals I’ve ever seen—better returns with lower risks, less effort, and more scalability.

For a real estate geek like me, it’s a dream come true, thanks to technology, AI, and the expansion of institutional-grade property management services in business-friendly U.S. states.  I know many hate Trump and are sick of tariffs but I can't find the same investment advantages here in Canada.

Take my off-market deal in San Antonio versus the off-market deal I did near McMaster University in Hamilton:

• Upfront renovations: $12,000 vs. $110,000
• Property age: 20 years old vs. 100 years old
• Basement issues: None (no basement) vs. mold, cockroaches, and leaking that required waterproofing
• Tenant management: One stable tenant vs. seven university students who had never lived on their own before
• Utilities: Tenant-paid vs. inclusive (including a $2,000 water bill thanks to a leaky toilet)
• Financing: Cheap mortgage vs. B-lender at 10% because no bank or credit union would lend to us
• Regulations: No rental licensing vs. strict rental licensing a couple thousand to setup up, a couple hundred in added costs per year I can't pass on thanks to rent control

If you're frustrated with Ontario’s landlord laws, you're not alone. Many investors are making the shift to landlord-friendly markets.  In my professional opinion, the business friendly States in the U.S. make the most sense since my clients receive all the benefits of passive investing like a REIT but pay less fees, keep all the equity and control unlike any investment I've seen before and I'm here to guide you every step of the way in how to diversify, de-risk, including how to list investment properties for sale for maximum return, even if tenanted.

All signs point to rising rents and real estate prices in the U.S. markets I've targeted for my clients, we wouldn't be there otherwise, billions of dollars being invested to create high paying jobs at a scale greater than 10X Canada's and by industry leaders.  Even if you want to do it yourself, that's totally cool, we've had Glen Sutherland on this show and we'll have more from our Canadian community who have transitioned to the US investors and you'll hear from them on this show as I want everyone to know the truths about do it yourself investing cross border and I'm grateful to have friends who will come on this show and be so transparent.I'm happy for anyone who continuously improves their investments, lives and achieving their financial goals

Thank you again, my 17 loyal listeners, for giving me this platform to make a difference in our community. If you'd like to get more tactical learning and real education

A great place to go is our iWIN Meeting on Saturday, April 26th (limited in-person seating + Zoom webinar). Thanks to our sponsors at SHARE and LendCity, lunch is covered.

Topics include: ✅ Short-term rentals & student rentals—What’s working now, and what’s not? ✅ The best landlord-friendly markets for Canadians (active & passive investing strategies) ✅ Property management in a recession—How to protect cash flow & avoid costly pitfalls ✅ How to sell a tenanted property for maximum ROI ✅ Mortgage market update—Where rates and terms are heading + CMHC MLI Select changes

The choice is simple: keep hoping Ontario changes, or step into a market where laws protect your investments and cash flow is king. See you there!