How Canadians Actively Invest in America: E-2 Visa, Co-Living Strategy & Execution 

Recorded: October 2025
Guest:Lauren Cohen, International lawyer and cross-border strategist
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Canadian investors are no longer waiting for Ottawa’s next move — they’re moving capital and opportunity south. In this episode, international lawyer and cross-border strategist Lauren Cohen explains how Canadians can actively invest in the U.S. using the E-2 visa and smart business models like co-living real estate.

The “Coveted” Visa: 
The E-2 visa allows Canadians to live in the U.S. while owning and operating a real business — typically granted in five-year renewable terms. It’s flexible, family-friendly (the spouse can work anywhere), and perfect for entrepreneurs who want to turn investments into lifestyle freedom. 

Active, Not Passive: 
Purely passive rentals don’t qualify for E-2 purposes. Lauren’s team builds operating businesses around real estate assets, ensuring they meet visa requirements and produce sustainable income. Most investors start with US$100–150K in capital to establish a credible, scalable structure. 

The Co-Living Edge: 
Think of co-living as co-working for housing — multiple tenants renting by the room with ensuite baths. In affordable, growth markets like Jacksonville, Houston, and Atlanta, these models can produce 14–16% cap rates with professional management and affordable entry points around US$300–350K. 

Timing Is Everything: 
Visa policy shifts can happen overnight. Canadians considering a move should structure their entities and business plans early, before new fees or restrictions appear. 

Next Steps: 
If you’re ready to combine immigration strategy, business execution, and cash-flow real estate, visit InvestingAcrossBorders.net to learn more or book a strategy session with Lauren Cohen. 

🎧 Listen to the full episode here


10 Rapid Fire Q&A

  1. What is an E-2 visa for Canadians? 
    A renewable five-year visa that lets Canadians live in the U.S. while owning and operating a substantial business. 
  1. Can passive real estate qualify for E-2? 
    No — you must actively run a real, revenue-generating enterprise such as a co-living operation or service-based company. 
  1. How much investment do Canadians need for E-2? 
    Typically US$100K–150K, though higher investments demonstrate stronger credibility and sustainability. 
  1. What is co-living real estate? 
    A model where investors rent rooms by the door — like co-working for housing — yielding higher cash flow and flexibility. 
  1. Best U.S. markets for co-living in 2025? 
    Jacksonville, Houston, and Atlanta — affordable entry, job growth, and strong rental demand. 
  1. How much capital do I need to start? 
    Expect ~US$150K all-in, including 30% down and setup costs. 
  1. Why are Canadians shifting investments to the U.S.? 
    Better cash flow, more business-friendly policies, and visa-linked opportunities for lifestyle flexibility. 
  1. How quickly can U.S. visa rules change? 
    Changes can occur within 24 hours via presidential proclamations — proactive setup is essential. 
  1. Can my spouse work in the U.S. on an E-2 visa? 
    Yes, the E-2 spouse can work anywhere in the United States. 
  1. Where can Canadians learn about cross-border investing? 
    Visit InvestingAcrossBorders.net for resources, webinars, and personalized strategy sessions. 

📜 Full Transcript

The full, cleaned transcript of my conversation with Lauren Cohen is available here for anyone who wants to dive deeper.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/how-canadians-actively-invest-in-america-e-2-visa-co/id1100488294?i=1000734435194

On Spotify: https://open.spotify.com/episode/6YnZZ4vwLiepqzYhpT5FS3?si=b17b2feef85943eb

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/6f858e03-a030-435b-8305-fcba7788eeb7/the-truth-about-real-estate-investing-for-canadians-how-canadians-actively-invest-in-america-e-2-visa-co-living-strategy-execution

Audible: https://www.audible.ca/pd/B0FYQFT7FY?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/qDUbfZH-Pog

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

  • Do your investments match your long-term goals?
  • Do you fully understand how your strategies work?
  • Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

  • Finding quality income properties
  • Structuring the legal and tax side
  • Managing the property manager and insurance provider
  • Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.


Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto


Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Apartments vs. Business Income: How Real Estate Investing Is Evolving in 2025

Recorded: October 2025
Guest:Elizabeth Kelly, award-winning real estate investor, coach, and long-time educator 
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

In 2025, the phrase “buy a duplex, add a suite, and live off the cash flow” doesn’t hit the same.  The numbers literally don’t work when existing suited houses can be acquired for less $$. 

Canadian investors in Ontario, Quebec and BC (so the vast majority) are waking up to a new reality: the old formulas don’t work anymore. Rates are higher, values are soft, and “passive income” is harder to find north of the border. 

So what’s next? 

To unpack that, I sat down with Elizabeth Kelly — an award-winning real estate investor, coach, and long-time educator who’s been through multiple market cycles. Elizabeth built a 100+ unit portfolio, ran a full property management business in Northern Ontario, and today coaches investors on how to build real cash flow and resilience. 

Her message was clear: the future of investing looks less like “apartments” and more like “businesses.” 

The New Reality: Cash Flow Is Built, Not Bought 

Back in the early 2010s, Elizabeth and her husband could buy small-town multis with 5% down, get conventional financing, and cash flow from day one. 

Fast-forward to 2025: those days are gone. 

“You can’t copy a 2016 playbook and expect it to work in 2025,” she says. “Today, you have to build cash flow — not hope for it.” 

That means thinking like an operator, not just a landlord. The investors winning today are adding business income inside their properties — things like short-term rentals, storage, office rentals, or service-based tenants (salons, laundromats, co-working). 

Her own Northern Ontario building is a 33,000-square-foot former seniors’ home with multiple income lines: long-term rooms, offices, Airbnb units, and a salon. 
One property. Many businesses. Real cash flow. 

The Problem With “Government-Backed” Investing 

In the last few years, everyone and their cousin has been chasing CMHC MLI Select financing. Cheap debt, long amortizations — what’s not to love? 

Elizabeth’s warning: don’t build your business on government promises. 

“I don’t trust the government to keep giving cheap money forever. If policy changes, your whole model collapses.” 

She insists her portfolio must work without CMHC. The government may subsidize your project today — but the policy winds shift fast. If your deal only works with special financing, it’s not a deal. 

 From FOMO to Fundamentals 

Elizabeth spends much of her coaching time helping investors get out of trouble — overleveraged BRRRRs, private loans at 10–12%, or multifamily flips stuck mid-renovation. 

The root cause? FOMO and blind trust. 

“Too many investors handed off their judgment to brokers or mentors without understanding the math,” she says. “Education comes before execution.” 

She and her husband once spent $65,000 on mentorship and courses — and she says it saved them hundreds of thousands in mistakes. 

In 2025, education isn’t optional. It’s survival. 

The “Buy Box” That Fits You 

Every investor has a buy box — whether they know it or not. It’s your unique mix of: 

  • Cash flow needs 
  • Risk tolerance 
  • Time commitment 
  • Tenant type comfort 
  • Capital available 

Elizabeth’s advice: stop copying someone else’s playbook. 
Your buy box should match your lifestyle — not your friend’s or your Instagram feed. 

If you’re too busy or risk-averse to self-manage tenants, consider passive, managed options like U.S. single-family rentals (SHARE) or private lending with conservative LTVs. 

If you’re hungry for higher returns, be ready to operate like a business owner — not a spectator. 

Partnerships and Private Lending: Trust, Verify, and Control 

After seeing partnerships implode, Elizabeth now only partners with people who bring capital, competence, and character. 

“My reputation is worth more than any one deal,” she says. 

For private lenders, she warns: if you’re not ready to take over the property, you’re not ready to lend. Always be on title, know your LTV, and underwrite the borrower’s plan yourself. 

And if you wouldn’t want to own that exact property in that exact neighbourhood? Don’t lend on it. 

 The End of “Passive” Canada? 

With high prices and thin margins, truly passive real estate investing in Canada is nearly extinct. 

That’s why more Canadians are exploring U.S. single-family rentals, where landlord laws are friendlier, PM fees are success-based, and you keep full title control. (That’s what we do at SHARE — simple, cash-flowing homes in stable markets.) 

Whether you go cross-border or stay local, the rule is the same: 
Control your income, don’t chase someone else’s yield. 

Life Balance, Cryo Therapy, and the Bigger Picture 

After all that talk about resilience, Elizabeth and I agreed on one more thing: take care of yourself. 

Her go-to recovery tool? CryoStrong in Markham and Scarborough — a two-minute, -120°F cold therapy chamber that boosts energy and reduces inflammation. 

Because at the end of the day, financial freedom means nothing if you’re too burned out to enjoy it. 

🎧 Listen to the full episode here

Final Thought 

Real estate is no longer a passive asset game. 
It’s a business — and your success depends on how well you can adapt, operate, and create value. 

“Build resilience and flexibility,” Elizabeth says. “Pivot faster than everyone else.” 


Rapid Fire: 10 Questions & Answers For Elizabeth Kelly 

  1. What real estate strategies still work for Canadian cash flow in 2025? 
    Mixed-use, legal STRs, and commercial-adjacent plays that add a business to the building—so you can force income instead of waiting for appreciation.  
  1. Should investors rely on CMHC/MLI Select for multifamily deals? 
    No—treat subsidies as bonus, not backbone; policy can change and derail financing timelines and exits.  
  1. How can I define a real estate “buy box”? 
    Match property type, tenant profile, market, and activity level to your goals, risk tolerance, and time—your buy box, not someone else’s.  
  1. Are partnerships safe for first-time investors? 
    Only if incentives, capital depth, and execution ability check out—and you can underwrite the deal yourself.  
  1. Is private lending still worth it in Canada? 
    Yes, when you’re on title at sensible LTVs, with clear recourse and a takeover plan; bad operators and weak collateral are the real risk.  
  1. What went wrong in New Brunswick for many investors? 
    Thin appreciation, higher non-owner property taxes, management challenges (even pests), and investor-driven price surges that weren’t sustainable.  
  1. How do I “force” cash flow without a gut reno? 
    Add income lines: furnished mid-term rentals, STR suites where legal, small offices, storage, vending, or service tenants that fit zoning.  
  1. What’s the fastest way to cut risk in a shaky portfolio? 
    Stabilize tenancy first, then refi/sell selectively; diversify income outside real estate to support debt coverage.  
  1. Is passive income realistic for Canadian residential rentals right now? 
    Rare—most “passive” plays need either business income add-ons or different markets (e.g., U.S. SFRs with aligned incentives). 
  2. What mindset do investors need in uncertain markets? 
    Resilience and flexibility: educate, pivot quickly, and balance optimism with brutal facts. 

📜 Full Transcript

The full, cleaned transcript of my conversation with Elizabeth is available here for anyone who wants to dive deeper into her journey as a real estate investor

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/apartments-vs-business-income-how-real-estate-investing/id1100488294?i=1000733146751

On Spotify: https://open.spotify.com/episode/2kn4yxTDairBBjX7Yw8xpe?si=Ag0sdiHlRRGsYKdLG4p6dg

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/37ec4987-4fe2-4e29-b93e-3928288c755f/the-truth-about-real-estate-investing-for-canadians-apartments-vs-business-income-how-real-estate-investing-is-evolving-in-2025

Audible: https://www.audible.ca/podcast/ITEM-NAME/B0FVPQ5Z6M?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/hoIwjG-PJrA

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

  • Do your investments match your long-term goals?
  • Do you fully understand how your strategies work?
  • Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

  • Finding quality income properties
  • Structuring the legal and tax side
  • Managing the property manager and insurance provider
  • Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.


Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto


Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

️Why Canadian Multifamily Real Estate Still Makes Sense in 2025 – Insights from Alfonso Cuadra

Recorded: October 2025
Guest:Alfonso Cuadra
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

In a market clouded by uncertainty, rising interest rates, and inflation, Alfonso Cuadra—entrepreneur, educator, and founder of Wealth Genius—makes a compelling case for why Canadian multifamily real estate remains one of the most resilient and strategic investments in 2025. 

On this week’s podcast, Alfonso shares his journey from teenage father to financially free investor by age 30. With over 26 years of experience and thousands of students mentored, Alfonso has built a portfolio that spans Canada and the U.S., focusing on scalable multifamily assets, commercial financing, and long-term wealth strategies. 

Key Takeaways from the Episode 

  1. Bigger Is Better in Real Estate

    Alfonso explains why scaling up to larger multifamily properties reduces risk and increases cash flow. With more units, landlords can afford on-site staff and professional management, turning real estate into a business—not a job.

  2. Equity Over Expensive Debt

    He warns against overleveraging with private loans and promissory notes, calling them “the lazy way to raise capital.” In  contrast, Alfonso advocates for equity partnerships that share risk and reward, especially during market downturns.

  3. CMHC and MLI Select: Use Responsibly

    CMHC’s MLI Select program may offer attractive leverage, but Alfonso urges investors to approach it with caution. He highlights the importance of preparing for renewal risks and meeting debt coverage ratio (DCR) requirements. To ensure long-term stability, he recommends sticking with a standard 40-year amortization

  4. Secondary Markets Are the Future

    Alfonso’s strategy focuses on secondary markets within an hour of major cities like Toronto and Ottawa. As urban centers densify, these surrounding areas offer predictable growth and better affordability.

  5. Inflation Is Inevitable—Invest in Hard Assets

    With Canada needing 5 million homes by 2030 and inflation eroding purchasing power, Alfonso sees multifamily real estate as the ultimate hedge. “Numbers don’t lie,” he says. “Multifamily just makes sense.”

🎧 Listen to the full episode here

Upcoming Event: Expand Investor Conference 

Alfonso invites listeners to the Expand Investor Conference, happening October 31–November 2 in Mississauga. With over 50 presenters, breakout sessions, and networking opportunities, it’s Canada’s hottest real estate event. I, Erwin Szeto will also be speaking at the event.

Learn more: https://wealthgenius.ai 
Connect with Alfonso: https://instagram.com/alfonsocuadra 
Watch his developments: Canadian Real Estate Channel on YouTube 


Real Estate Investing in Canada: 2025 Q&A with Alfonso Cuadra 

  1. Why does Alfonso Cuadra prefer multifamily over single-family investing?
    Multifamily properties offer better cash flow, scalability, and risk distribution. With more units, landlords can afford professional management and avoid being hands-on.
  2. What’s the biggest mistake new investors make?
    Relying solely on property appreciation is speculation, not investing. Alfonso advises buying assets you’d be willing to hold for life.
  3. Why is commercial financing better for scaling real estate?
    Commercial mortgages focus on the asset’s performance, not personal income. This allows investors to scale even if they’re self-employed or have poor credit.
  4. What is Alfonso’s strategy for choosing markets in Canada?
    He targets secondary markets within an hour of major cities like Toronto or Ottawa. These areas are poised for growth and offer better affordability.
  5. How does Alfonso view CMHC and MLI Select financing?
    He uses MLI Select cautiously, warning that high leverage can backfire if debt coverage ratios aren’t met at renewal. Standard CMHC 40-year amortization is safer.
  6. What’s Alfonso’s stance on promissory notes and private lending?
    He strongly opposes unsecured loans like promissory notes, calling them risky and unsustainable. He prefers equity partnerships for long-term stability.
  7. Why is inflation a key reason to invest in real estate?
    Real estate is a hard asset that appreciates with inflation. Alfonso sees it as the best hedge against a weakening fiat currency system.
  8. What kind of developments is Alfonso building in 2025?
    He’s building stick-frame, 4–5 story multifamily buildings in secondary Ontario markets like Brockville and Arnprior. These are not subject to rent control.
  9. What’s the Expand Investor Conference about?
    It’s a 3-day event hosted by Wealth Genius, featuring 50+ presenters and breakout sessions. It focuses on optimizing portfolios and preparing for the global wealth transfer.
  10. Where can people learn more or connect with Alfonso Cuadra?
    Visit https://wealthgenius.ai or follow him on Instagram at https://instagram.com/alfonsocuadra. You can also find his developments on the Canadian Real Estate Channel on YouTube.

📜 Full Transcript

The full, cleaned transcript of my conversation with Alfonso is available here for anyone who wants to dive deeper into his journey as a real estate investor

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/why-canadian-multifamily-real-estate-still-makes-sense/id1100488294?i=1000732182131

On Spotify: https://open.spotify.com/episode/3biCf3AJnKuvyMxVEnxuzj?si=2oIH0RkHTx6cBlJm1pC6vQ

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/e11fd92a-1543-4fab-9514-d632668365b2/the-truth-about-real-estate-investing-for-canadians-why-canadian-multifamily-real-estate-still-makes-sense-in-2025-%E2%80%94-insights-from-alfonso-cuadra

Audible: https://www.audible.ca/pd/B0FWMB9H75?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/ceHJKGLbnEI

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

  • Do your investments match your long-term goals?
  • Do you fully understand how your strategies work?
  • Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

  • Finding quality income properties
  • Structuring the legal and tax side
  • Managing the property manager and insurance provider
  • Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.


Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto


Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Quitting Government After 22 Years: Luis Rivas’ Journey from Speculator to Real Estate Coach

Recorded: September 2025
Guest: Luis Rivas
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

After 22 years in the federal government, Luis Rivas made a bold move—he retired early, cashed in his pension, and pivoted into real estate investing and coaching. In this episode, Luis shares how he went from speculating on Ottawa condos to building a multifamily portfolio across Canada and the U.S., and eventually becoming a head coach at WealthGenius. 

Luis opens up about the emotional toll of leaving a secure job, the lessons learned during COVID, and the mindset shift required to thrive as an investor. He breaks down his strategy for underwriting multifamily deals, targeting 5–6% cap rates, and why he’s now looking south of the border for better returns and landlord-friendly policies. 

We also dive into the challenges of being a landlord in Ontario, the importance of property management, and why Canadians must invest to secure their retirement. Luis shares his formula for calculating how big your portfolio needs to be to hit your lifestyle goals—and why legacy planning matters more than ever. 

📍 Catch Luis at the Expand Conference in Mississauga, October 31–November 2, where he’ll be speaking alongside top investors. 
🎤 I, Erwin Szeto, will also be speaking at the event. 
📲 Connect with Luis: Instagram & YouTube — @cashflow.rivas 


Real Estate Investing & Coaching with Luis Rivas: Top Questions

  1. How did Luis Rivas transition from government work to real estate investing? 
    He retired early during COVID, cashed in his pension, and began coaching while building a multifamily portfolio. 
  1. What was Luis Rivas’ first real estate investment? 
    Two pre-construction condos in Ottawa, which he later sold due to poor cash flow and lack of appreciation. 
  1. Why does Luis prefer multifamily properties over condos? 
    Multifamily offers better cash flow, scalability, and commercial financing options, especially in secondary markets. 
  1. What cap rate does Luis target in his investments? 
    He aims for 5–6% cap rates, with property management included in the underwriting. 
  1. Why is Luis looking to invest in the U.S. market? 
    U.S. markets offer better cap rates, landlord-friendly laws, and more scalable property management systems. 
  1. What advice does Luis give to new investors? 
    Get educated, join a community, and design your portfolio based on your lifestyle goals—not arbitrary door counts. 
  1. How does Luis calculate the size of a portfolio needed for retirement? 
    He uses a formula based on monthly income goals, cash-on-cash return, and equity share to determine total portfolio value. 
  1. What are the risks of investing in rural or tertiary markets? 
    Limited financing, property management, and appreciation can cripple deals if not properly managed. 
  1. What is Luis’ take on Ontario’s rent control policies? 
    He believes they unfairly burden landlords and discourage investment, pushing many to look outside Ontario. 
  2. What asset classes is Luis exploring next? 
    He’s researching self-storage and care homes, especially in Texas, for their automation potential and lack of rent control. 

📜 Full Transcript

The full, cleaned transcript of my conversation with Luis is available here for anyone who wants to dive deeper into his journey as a real estate investor

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/pensions-vs-real-estate-which-really-builds-wealth/id1100488294?i=1000729706240

On Spotify: https://open.spotify.com/episode/7FtMpPavD0xMB8riqiayGc?si=WFCkN9wDTu-GJo8sf8Jhxw&nd=1&dlsi=3d5328e1d2b54a60

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/41112347-107b-407a-ab97-b7a674773e7b/the-truth-about-real-estate-investing-for-canadians-pensions-vs-real-estate-which-really-builds-wealth

Audible: https://www.audible.ca/pd/B0FTMP1RMM?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/mWBef5KN5W4

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

  • Do your investments match your long-term goals?
  • Do you fully understand how your strategies work?
  • Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

  • Finding quality income properties
  • Structuring the legal and tax side
  • Managing the property manager and insurance provider
  • Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.


Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto


Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

From Family Crisis to Debt-Free Kids: Holistic Wealth Planning in Action 

Recorded: November 2022
Guest: Arminda Simao
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast


Building a Wealth Plan with Student Rentals

When Arminda and her late husband Frank bought two student rentals near McMaster University in 2015, they weren’t chasing a trend. They were building a plan. With guidance from me as their Realtor and investment specialist, they targeted solid properties just outside the campus hot zone—close to transit and groceries—then upgraded them with student-friendly finishes and safety standards. The goal wasn’t door-count bragging rights; it was financial freedom for their family and a path to help their kids through school without debilitating debt.

Cash Flow and Stability Through Real Estate Investing

Within months, they owned two income properties, each configured for multiple student rooms. Rent supported expenses and created net cash flow—about $1,500/month across both houses—while giving their daughter Alexia a safe place to live during undergrad. The plan worked because it balanced fundamentals: quality renovations, conservative financing, and a steady rental niche with built-in turnover (students graduate, rents reset). 

The Role of Insurance and Pensions

Then life changed. Frank—healthy, proactive about checkups—was diagnosed with glioblastoma, an aggressive brain cancer, with a 12–18 month prognosis. Overnight, the plan’s resilience was tested. What carried the family wasn’t just real estate cash flow; it was the right mix of real estate, insurance, and a pension. A $100,000 critical illness payout created breathing room at diagnosis. Life insurance later provided stability. Most importantly, Frank’s union pension continued as survivor income for Arminda—a predictable cash flow for life. For most Canadian investors, that kind of pension is the dividing line between uncertainty and confidence in retirement.  

Insuring the Family vs. Insuring the Mortgage

Arminda also learned the difference between insuring the mortgage and insuring the family. During a refinance, the bank offered mortgage life insurance; they declined. After Frank’s passing, Arminda regretted that decision because the rental mortgages remained. The practical takeaway for Canadian investors: rather than lender-tied mortgage insurance (declining balance, lender as beneficiary), consider adding a death benefit to a personally owned life insurance policy. It’s flexible, portable across lenders, and allows the family—not the bank—to decide whether to retire debt, fund education, or reinvest.  

Student Rentals That Stand the Test of Time

Despite the hardship, the long-term outcomes speak for themselves. Alexia advanced through dental school; Leandro completed denturism and is working in his field. The rentals kept performing—even through the pandemic—thanks to student demand and disciplined operations. Arminda set high standards (safety, cleanliness, responsive maintenance), relied on her network (contractors, landscapers), and empowered tenants to help with showings and referrals. The result: strong retention, smooth turnovers, and market-aligned rents over time.  

Lessons for Canadian Investors 

  • Real estate builds wealth when you buy right, renovate to standard, and price for quality. 
  • Insurance provides liquidity and flexibility when life happens—critical illness and life insurance are not “nice to have”; they’re essential. 
  • Pensions sustain stability. If you don’t have a defined-benefit pension, build your own with positive-cash-flow income properties and pension-style solutions (segregated funds or annuities). 
  • Insure the family, not just the mortgage. Increasing personal life insurance death benefit typically beats mortgage insurance for flexibility and estate efficiency. 
  • Think holistically: real estate + insurance + pension + estate planning = resilience. 

This re-release is perfectly timed with our Wealth Summit 2025 and the launch of iWIN Wealth Planner—a holistic, one-stop shop for wealth planning. If you’ve ever wondered, “Will I have enough to retire—and how much will I leave for my kids?”—Arminda’s story shows how a plan turns those questions into answers. 

Wealth Summit 2025 – September 27th, 2025 | Oakville & Online

We’re bringing back the same energy and insight that made our Wealth Hacker Conferences legendary, where Grant Cardone and Jesse Itzler once took the stage, but this year, the focus is on what really matters for long-term financial freedom:

  • Best practices in financial and estate planning
  • How to build or replace a pension
  • Protecting your wealth and minimizing taxes legally
  • Wills, power of attorney, and intergenerational wealth transfer

This will be an intimate, high-impact event with only 40 in-person seats in Oakville, plus limited online access. If you’re serious about securing your financial future, you won’t want to miss it.

🎟️ Save your spot now
⚡ Don’t wait—seats are already filling up!


10 Essential Q&As on Real Estate, Insurance, and Building Your Own Pension 

1. What’s the safest starting strategy for Canadian real estate investors?

Focus on student rentals near transit and groceries, renovated to a high standard with proper life-safety. This niche offers steady demand and natural turnover for rent resets.

2. How did real estate help Arminda achieve financial freedom?

Two cash-flowing student rentals generated about $1,500/month combined and provided housing for her daughter. That income, plus long-term appreciation, supported her family through a health crisis.

3. What role did insurance play in Arminda’s plan?

Critical illness paid $100,000 at diagnosis and life insurance provided tax-free funds later. Together they gave liquidity and stability when it mattered most.

4. Why is a pension so critical for retirement planning?

Frank’s union pension became lifetime survivor income for Arminda, providing predictable cash flow independent of markets or tenants. For many Canadian investors, a pension is the biggest factor in sustainable retirement.

5. Mortgage insurance vs. personal life insurance—what’s better?

Increasing a personal life insurance death benefit is usually superior to lender mortgage insurance. It’s flexible, portable, level coverage, and your family—not the bank—controls the payout.

6. How can investors without a workplace pension build one?

Combine positive cash-flow income properties with pension-style solutions like segregated funds or annuities. This creates reliable income streams that mimic a defined-benefit pension.

7. Did student rentals hold up during the pandemic?

Arminda had only a brief vacancy period, and demand rebounded strongly, with room rents moving higher. Quality properties in the right micro-market fared well.

8. What makes a student rental competitive?

Clean, safe renovations; responsive maintenance; and proximity to McMaster University, transit, and grocery options. Tenants will pay for quality and convenience.

9. How did estate planning affect Arminda’s outcome?

Wills, POAs, and beneficiary designations simplified decisions during crisis. The family’s existing life insurance and pension coordination made the transition manageable.

10. What’s the biggest takeaway for Canadian investors seeking financial freedom?

Holistic financial planning wins: real estate for growth, insurance for protection, and pensions (or pension replacements) for stability. Don’t just insure the mortgage—insure the family.


📜 Full Transcript

The full, cleaned transcript of my conversation with Arminda is available here for anyone who wants to dive deeper into her family’s journey, the role of real estate, insurance, and pensions, and how holistic wealth planning can reshape your financial future.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/financial-freedom-after-family-crisis-arminda-simaos/id1100488294?i=1000727352534

On Spotify: https://open.spotify.com/episode/51p1yn6DY4Rc6WBxs9wnUZ?si=Cp3P_mNzR0KxK0o3jLpg3A

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/be2f2772-fbab-4407-ad48-232ac0eef2d8/the-truth-about-real-estate-investing-for-canadians-financial-freedom-after-family-crisis-arminda-simao%E2%80%99s-holistic-wealth-planning-in-action

Audible: https://www.audible.ca/pd/B0FRN9S517?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/4yDmdldNkpU

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

  • Do your investments match your long-term goals?
  • Do you fully understand how your strategies work?
  • Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

  • Finding quality income properties
  • Structuring the legal and tax side
  • Managing the property manager and insurance provider
  • Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.


Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto


Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Solving Ontario’s Rental Crisis & Profiting—One Smart Building at a Time 

Recorded: September 2025
Guest: Jimmy La and Kartik Singla, SDG Canada
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast


Canada’s housing crisis isn’t going away—and developers like Jimmy La and Kartik Singla are stepping up with bold, scalable solutions. In this episode, I had an insightful conversation with the co-founders of SDG Canada about their ambitious infill development strategy, the benefits of CMHC’s MLI Select financing, and how their Clapperton Village project in Barrie is reshaping the rental landscape.

Key Takeaways

  • SDG Canada is building modular, energy-efficient rental housing tailored for multi-generational families. 
  • Their Clapperton Village development includes 100+ units across nine buildings, with plans to expand to 150. 
  • The project is powered by CMHC’s MLI Select program, allowing 95% financing and long amortization terms. 
  • Amenities include EV chargers, co-working spaces, gyms, and even air/water quality tracking. 
  • The Missing Middle Conference on Sept 12 at the Fairmont Royal York will bring together mayors, ministers, and developers to tackle housing challenges head-on. 

Why It Matters:

With Ontario falling short of its housing targets and immigration numbers rising, the need for smart, scalable rental housing has never been greater. SDG’s approach—low-rise, family-friendly, and financially viable—is a blueprint for the future.

Don’t Miss These Two Game-Changing Events

Missing Middle Conference – September 12th, 2025 | Fairmont Royal York, Toronto

Canada’s housing crisis won’t be solved by chance—it requires bold ideas and collaboration. That’s exactly what the Missing Middle Conference is all about. Hosted by Jimmy La and Kartik Singla of SDG Canada, this one-day event brings together the brightest minds in housing and development, including:

  • Mayor Olivia Chow (Toronto), the Mayor of Burlington, and other city leaders
  • Federal and Provincial Housing Ministers’ teams
  • Top developers, consultants, and investors
  • And of course, Erwin Szeto, host of The Truth About Real Estate Investing for Canadians

If you care about the future of housing, want to understand how to profit from infill development, or are simply seeking to network with leaders driving change, this is where you need to be.

🎟️ Reserve your spot now at themmc.ca
💸 Use code MMC15% for 15% off tickets

Wealth Summit 2025 – September 27th, 2025 | Oakville & Online

After you’ve learned how to create millions through real estate development, it’s time to protect and multiply that wealth. That’s where the Wealth Summit 2025 comes in.

We’re bringing back the same energy and insight that made our Wealth Hacker Conferences legendary, where Grant Cardone and Jesse Itzler once took the stage, but this year, the focus is on what really matters for long-term financial freedom:

  • Best practices in financial and estate planning
  • How to build or replace a pension
  • Protecting your wealth and minimizing taxes legally
  • Wills, power of attorney, and intergenerational wealth transfer

This will be an intimate, high-impact event with only 40 in-person seats in Oakville, plus limited online access. If you’re serious about securing your financial future, you won’t want to miss it.

🎟️ Save your spot now
⚡ Don’t wait—seats are already filling up!


Smart Rental Development in Ontario: What You Need to Know

1. What is the Missing Middle in real estate?

The Missing Middle refers to housing types between single-family homes and high-rise condos—like duplexes, triplexes, and low-rise apartments.

2. Why is SDG Canada focused on infill development?

Infill allows them to add density in existing neighborhoods, using underutilized lots to build 6–60 unit rentals that meet real demand.

3. What is CMHC’s MLI Select program?

MLI Select is a financing program offering up to 95% loan coverage and long amortization for energy-efficient, affordable rental projects. 

4. How many units is SDG Canada currently developing?

They have 100 units in the pipeline across nine buildings, with plans to scale to 150 units in Barrie.

5. Why is Barrie a good market for rental development?

Lower land costs, supportive city planning, and proximity to new university campuses make Barrie ideal for scalable rental housing.

6. What kind of tenants are SDG’s buildings designed for?

Multi-generational families, professionals, and renters are seeking larger units with modern amenities. 

7. What amenities are included in Clapperton Village?

EV chargers, co-working spaces, gyms, saunas, air and water quality tracking, and shared outdoor areas.

8. Will MLI Select still be available in five years?

Yes—projects are grandfathered into the program with 50-year insured mortgages, making refinancing viable long-term.

9. How does modular construction help with sustainability?

It reduces waste, speeds up build time, and enables energy-efficient designs that exceed code by 45%.

10. What’s happening at the Missing Middle Conference?

Mayors, housing ministers, developers, and investors will gather to align on solutions for Canada’s housing crisis. 


📜 Full Transcript

The full, cleaned-up transcript from my conversation with the co-founders of SDG Canada is available here for anyone who wants to dive deeper into their infill development strategy, the role of CMHC’s MLI Select financing, and how Clapperton Village is reshaping the rental landscape in Barrie.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/canadas-housing-crisis-the-missing-middle-conference-2025/id1100488294?i=1000725725920

On Spotify: https://open.spotify.com/episode/7cOMIueDkR3utoSJ8J4UuH?si=IY8j3GTvSli8icVpgvWFvg

Amazon Music:https://music.amazon.ca/podcasts/930a-66d033586541/the-truth-about-real-estate-investing-for-canadians-canada%E2%80%99s-housing-crisis-the-missing-middle-conference-2025

Audible: https://www.audible.ca/podcast/ITEM-NAME/B0FQ4GN8T7?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/pGa85Erc9us

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

  • Do your investments match your long-term goals?
  • Do you fully understand how your strategies work?
  • Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

  • Finding quality income properties
  • Structuring the legal and tax side
  • Managing the property manager and insurance provider
  • Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.


Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto


Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

From Townhomes to Development: Michael Ponte’s Contrarian Take on Real Estate Investing 

Recorded: August 2025
Guest: Michael Ponte, the Founder of Savvy Investor
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast


Welcome back to another episode of “The Truth About Real Estate Investing for Canadians.” On this episode, I had the pleasure of welcoming back a four-time guest, my friend and seasoned investor, Michael Ponte. In our chat, he shared his perspective on how real estate investing has changed, his unique take on CMHC MLI Select financing, and the surprising connection between bodybuilding and disciplined investing.

The Evolution of Real Estate Investing

I’ve been in this game for a while, and it’s fascinating to see how the landscape has changed. Michael’s story is a great example. He started back in 2001 with a simple townhome in Edmonton, bought for just $78,000. It was an affordable entry point that offered solid cash flow. But as we discussed, those days are largely gone. That same property is now pushing $300,000, and the rent just hasn’t kept up. As Michael pointed out, the game has shifted. To make a deal work in today’s market, you often need to look at more complex strategies like development and intensive renovations.

A Contrarian View on CMHC MLI Select

In our community, CMHC MLI Select financing has a lot of buzz. But Michael offered a compelling counterpoint. He’s cautious about the trend of overleveraging and relying on government-backed financing to justify what he sees as overpriced deals. His concern is that many of these projects are priced at the very top of the market, leaving little room for error or a way to add value. He stressed that he still believes in the fundamental rule of “making your money on the buy” and prefers to focus on older multifamily properties where he can create value through smart renovations and operational improvements.

Bodybuilding and Real Estate: A Discipline-Driven Parallel

One of the most powerful moments of our conversation was when Michael opened up about his bodybuilding journey. After a serious health scare, he committed to an intense training and nutrition regimen, which led him to place in the top five in multiple competitions. He drew a brilliant parallel between the discipline, sacrifice, and mindset required for bodybuilding and what it takes to succeed in real estate. The lesson? Success isn’t about chasing the next shiny object; it’s about consistency and long-term discipline.

Key Takeaways

Real estate investing has moved beyond simple buy-and-hold strategies to require more complex development and value-add approaches.

  • CMHC MLI Select financing can be risky if used to justify a bad deal.
  • Discipline and long-term thinking are critical for success in both investing and life.
  • Treat your real estate ventures like a business with systems and a focus on scalability.
  • Stability and time are more valuable than chasing quick, flashy opportunities.

Bonus: Savvy Investor Summit

Bonus: Savvy Investor Summit

Before we wrapped up, Michael gave us a sneak peek into the upcoming Savvy Investor Summit, a free two-day virtual conference happening on September 13–14, 2025. It sounds incredible, with speed networking, an exhibitor hall, and over $10,000 in prizes, including a Caribbean cruise for two.

To find out more and register for the event, head over to: https://thesavvyinvestor.ca

Join Cherry Chan and me at the WEALTH SUMMIT 2025 on Saturday morning, September 27th, 2025. Seating is extremely limited, so block off your calendar now. We’ll also be broadcasting the event as a webinar. And yes—lunch is sponsored, so you can stick around and network with fellow investors. Save a spot for yourself now


Real Estate Investing in 2025: Contrarian Insights from Michael Ponte 

1. What is CMHC MLI Select, and why is it controversial among Canadian real estate investors?

CMHC MLI Select is a multifamily mortgage financing program offering high leverage and long amortization for apartment developments. Michael Ponte cautions that many investors rely on it to justify overpriced deals, increasing financing risk if market conditions shift.

2. Why are townhomes no longer a strong investment in the Canadian real estate market?

Townhomes that once offered solid cash flow now suffer from poor rental yields. Prices have surged while rents lag, collapsing the cash flow ratio and making them less viable for new real estate investors.

3. How has Canadian real estate investing evolved over the past two decades?

Investing has shifted from affordable townhomes to large-scale development projects and multifamily conversions. Michael Ponte emphasizes the need for adaptability and a disciplined investing mindset.

4. What are the risks of overleveraging in real estate development?

Overleveraging increases debt exposure and financing risk, especially in volatile markets. Michael warns that relying on aggressive financing structures can leave investors vulnerable to interest rate hikes and market corrections.

5. How does bodybuilding relate to real estate investor discipline?

Michael Ponte’s experience as a competitive bodybuilder taught him the value of consistency, sacrifice, and mental toughness. These traits directly translate to disciplined real estate investing and long-term success.

6. What is the Savvy Investor Summit, and who should attend?

The Savvy Investor Summit is a free Canadian real estate conference happening September 13–14, 2025. It’s designed for investors seeking business systems, networking, and expert insights across multifamily, development, and property management.

7. How can investors identify low ROI properties in their portfolio?

Michael recommends reviewing your portfolio for properties with poor cash flow or high management demands. Selling these underperforming assets can free up time and capital for stronger investments.

8. Why does Michael Ponte prefer older multifamily buildings over new developments?

Older multifamily properties offer better value-add opportunities through renovations and operational improvements. Michael believes they provide stronger returns and lower risk than high-priced new builds.

9. What mindset mistakes do new real estate investors often make?

New real estate investors often chase door count or flashy strategies without understanding business fundamentals. Michael stresses the importance of systems, scalability, and treating real estate as a long-term business.

10. Is the Canadian real estate market still viable for investors in 2025?

Yes, but strategies must evolve. Michael advises focusing on fundamentals, avoiding hype, and adapting to changing conditions in the Canadian real estate market in 2025.


📜 Full Transcript

The full, cleaned-up transcript from my conversation with Michael is available here for anyone who wants to dive deeper into the nuances of protecting themselves as an Ontario landlord and building a stress-free investment portfolio.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/from-bodybuilding-to-real-estate-investing-michaels/id1100488294?i=1000725002855

On Spotify: https://open.spotify.com/episode/1gkYYhLHSFDZZr6ddVsnxM?si=4GA2cXr2QNeoC21mpARscA

Amazon Music:https://music.amazon.ca/podcasts/the-truth-about-real-estate-investing-for-canadians-from-bodybuilding-to-real-estate-investing-michael%E2%80%99s-24-year-investor-journey-lessons-learned

Audible: https://www.audible.ca/podcast/ITEM-NAME/B0FM8J4HPY?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/4o4Vo0RVZ7w

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

  • Do your investments match your long-term goals?
  • Do you fully understand how your strategies work?
  • Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

  • Finding quality income properties
  • Structuring the legal and tax side
  • Managing the property manager and insurance provider
  • Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.


Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto


Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

The Shocking Truth About Landlords in Ontario: 10 Fast Facts Every Investor Should Know

Recorded: August 2025
Guest: Boubah, Co-Founder of the Small Ownership Landlords of Ontario (SOLO)
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast


I’ll never forget our first non-paying tenant back in 2007.

The property was over 100 years old—charming in its own way—and brand new to us as owners. It was only our third investment property, and looking back… we really didn’t know what we were doing.

We missed obvious red flags, like the tenant’s SIN number being wrong. The two roommates were new to town, desperate for a place to rent, and we were too nice. We signed a lease. We accepted a personal cheque for the first and last month’s rent. And yes, we even handed over the keys before the cheque cleared. You know where this is going.

It was 2007, so expenses weren’t as brutal as they are today, but the ordeal still cost us around $10,000—including legal fees. The worst part? My partners were family. We were all upset, confused, and completely unprepared.

None of us even knew what an N4 was (a notice for eviction due to non-payment of rent). But our tenant sure did. When my family member handed him the notice at his workplace—Boston Pizza—he yelled at us to never come back.

Meanwhile, this same tenant was busy making himself at home—he even installed a heavy bag (the kind boxers use), drilled right into the living room ceiling. All while never paying a single dollar in rent. That was our introduction to Ontario’s rental system.

What no one told us in the early days was just how stacked the system is against landlords. How could I not change the locks on my own property when the tenant hadn’t even paid first and last month’s rent? Because if I did, the tenants could simply call the police—and in my experience, the police would side with them. The tenant. WTF?!

Fast Forward to Today…

It’s been nearly 20 years since that first painful lesson. Since then, I’ve coached more than 350 investor clients through their own journeys, and as a licensed Realtor since 2010, I’ve truly seen it all. And I can say with confidence: things have only gotten worse for landlords in Ontario.

That’s why I invited the co-founder of S.O.L.O. (Small Ontario Landlords Organization) onto my podcast. In this episode, we dive into the harsh realities of being a landlord in Ontario, where the system knows what’s broken, yet continues to side against landlords.

We talk about eviction parties, fraud teams, and how S.O.L.O. has grown into a 9,000-member grassroots movement. We also explore why so many Canadian investors are now looking south to landlord-friendly U.S. states—where the laws are clearer, the cash flow is stronger, and the risks are lower.

📅 Save the Date!

Cherry Chan and I are co-hosting an in-person meetup at our Oakville offices on Saturday morning, September 27th, 2025. Seating is extremely limited, so block off your calendar now. We’ll also be broadcasting the event as a webinar. And yes—lunch is sponsored, so you can stick around and network with fellow investors. Save a spot for yourself now

If you’re a landlord in Ontario—or thinking about becoming one—this episode is a must-listen. And if you’ve ever felt alone in the trenches, know this: you’re not. Tune in, learn, and let’s keep fighting the good fight… or, like me and so many frustrated landlords, consider taking the easier way out. 😊


🧠 10 Fast Facts Every Ontario Landlord Needs to Know

1. What is SOLO and who does it help?
SOLO (Small Ontario Landlords Organization) is a nonprofit that supports small landlords navigating Ontario’s rental system. It offers education, advocacy, and peer support to landlords facing tenant issues. 

2. Why is being a landlord in Ontario considered high risk?
Ontario landlords face long eviction timelines, limited legal recourse, and tenant-friendly laws that often delay resolution. The system is widely seen as stacked against property owners. 

3. How long does it take to evict a non-paying tenant in Ontario?
Evicting a non-paying tenant in Ontario can take 8 to 11 months, factoring in hearings, decisions, and sheriff scheduling. Professional tenants can stretch this process even longer. 

4. What is an N4 notice in Ontario real estate?
An N4 is a formal notice used by Ontario landlords to begin eviction proceedings for non-payment of rent. Many first-time landlords are unaware of this essential legal tool. 

5. Can landlords change the locks if rent isn’t paid in Ontario? 
No, Ontario law prohibits landlords from changing locks without a formal eviction order, even if rent hasn’t been paid. This legal restriction often surprises new landlords. 

6. What are eviction parties and why does SOLO organize them?
Eviction parties are community support events where volunteers help landlords clean up and emotionally recover after a tenant eviction. They reinforce that landlords are not alone. 

7. What is a professional tenant and why are they a problem? 
Professional tenants exploit Ontario’s rental laws to live rent-free for months by delaying hearings and abusing legal loopholes. They target small landlords who lack screening systems. 

8. Why are Ontario landlords investing in the U.S. instead? 
Many Ontario landlords are shifting to landlord-friendly U.S. states like Texas and Georgia for better cash flow, faster evictions, and stronger property rights. The risk-reward ratio is more favorable. 

9. What role does SOLO play in landlord advocacy?  
SOLO lobbies government officials, educates media, and supports legal reform to protect small landlords. It has met with the Premier and Minister of Housing multiple times. 

10. Is Ontario the worst jurisdiction for landlords in North America?
According to SOLO, Ontario is the only jurisdiction in North America where tenants can remain in a property without paying rent for extended periods. This makes it uniquely challenging for landlords. 


📜 Full Transcript

The full cleaned-up transcript from my conversation with Boubah is available here for anyone who wants to dive deeper into the nuances of protecting yourself as an Ontario landlord, navigating legal hurdles, and building a stress-free investment portfolio.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/ontario-landlord-crisis-tenant-fraud-evictions-solo/id1100488294?i=1000724039750

On Spotify: https://open.spotify.com/episode/1gkYYhLHSFDZZr6ddVsnxM?si=4GA2cXr2QNeoC21mpARscA

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/0186684c-5f4a-48ab-bc77-637c9138dfec/the-truth-about-real-estate-investing-for-canadians-ontario-landlord-crisis-tenant-fraud-evictions-solo-ca-solutions

Audible: https://www.audible.ca/pd/B0FP5NFL51?source_code=ASSGB149080119000H&share_location=pdp

Youtube: https://youtu.be/M_wHsRgi50Y

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

  • Do your investments match your long-term goals?
  • Do you fully understand how your strategies work?
  • Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

  • Finding quality income properties
  • Structuring the legal and tax side
  • Managing the property manager and insurance provider
  • Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.


Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto


Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Painting for Profit: Maximizing Renovation ROI with Brian Young of Home Painters Toronto

Painting for Profit: Maximizing Renovation ROI with Brian Young of Home Painters Toronto

Recorded: August 2025
Guest: Brian Young, Founder and CEO of Home Painters Toronto
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast


When it comes to getting top dollar for your property—whether selling or renting—painting is one of the highest-ROI renovations you can make. This week on The Truth About Real Estate Investing for Canadians, I sat down with Brian Young, founder and CEO of Home Painters Toronto, the city’s top-rated painting company.

With over 37 years in business, $3M+ in annual revenue, and more than 17,000 completed projects, Brian has mastered the art (and science) of delivering quality renovations quickly and profitably. His client list includes homeowners, landlords, and real estate agents who know that first impressions sell homes.

From Student Painter to Industry Leader

Brian launched Home Painters Toronto in 1987 while still a student at York University. What began as a summer job quickly evolved into a thriving business. Over the decades, Brian adapted to changing markets, shifting from cold-calling to a sophisticated online marketing machine, complete with SEO, social media, and review optimization.

Investor-Friendly Renovations That Pay Off

For real estate investors, every dollar counts. Brian recommends:

  • Prioritizing walls: Light, neutral colors like Decorator’s White, Cloud Cover, or Silver Satin appeal to the widest audience.
  • Targeting first impressions: Focus on the front door, entryway, kitchen, and main living spaces before secondary rooms.
  • Avoiding over-customization: Skip accent walls and bold colors when prepping for sale or rent.

Considering vinyl plank flooring over laminate for rentals—durable, water-resistant, and cost-effective.

Mistakes to Avoid

Brian has seen it all. Among the most common investor missteps:

  • Spending money where there’s no ROI, like removing stucco ceilings unnecessarily.
  • Neglecting small but impactful repairs, such as damaged trim or worn door handles.
  • Hiring trades without clear expectations or inspection schedules.

The Systems Behind a $3M Business

Incredibly, Brian has 8X’d his business while cutting his hours. His keys:

  • Switching from subcontractors to in-house crews for better quality control.
  • Using SOPs (Standard Operating Procedures) for every job.
  • Leveraging virtual assistants and overseas talent for admin work.
  • Holding team members accountable with daily photo updates and weekly calls.

Why Now is the Time to Renovate

With material and labor costs back to pre-pandemic levels, Brian says investors with cash should act now. “During COVID, costs were up 30–40% across the board. Now we’re back to 2018–2019 pricing—if you can renovate now, you’ll save.”

Learn More

If you’re in the GTA and want a free quote, visit HomePaintersToronto.com or call 416-494-9095. Even if you’re outside the area, Brian is happy to share advice from his 37 years in business.


🧠 8 Renovation Q&As Every Real Estate Investor Should Know

1. What is the highest-ROI renovation for selling a home?
Painting is often the best return-on-investment renovation, especially when focusing on main living areas, kitchens, and the front entrance.

2. Which paint colors appeal most to buyers?
Light, neutral shades like Decorator’s White, Cloud Cover, and Silver Satin work best for broad market appeal.

3. Should I replace or paint my kitchen cabinets?
Painting or spraying cabinets can cost 70–80% less than replacing them, making it the smarter choice in most cases.

4. What’s the best flooring for rental properties?
Vinyl plank flooring is durable, water-resistant, and more cost-effective than laminate or hardwood for rentals.

5. How can investors control renovation quality?
Set clear expectations in writing, inspect key milestones, and require photo updates from contractors.

6. What renovations should investors avoid before selling?
Skip personal design touches, unnecessary stucco removal, and painting rarely-seen spaces like closets.

7. Are renovation costs lower now than during COVID?
Yes—labor and materials have largely returned to pre-pandemic prices, making now a good time to renovate.

8. Why switch from subcontractors to employees in a renovation business?
Employees allow for more consistent quality control, easier implementation of SOPs, and stronger accountability.


📜 Full Transcript

The full cleaned-up transcript from my conversation with Brian Young is available here for anyone who wants to dive deeper into the nuances of painting for profit, building a successful business, and investor-friendly renovations

To Listen:

On iTunes: https://itunes.apple.com/ca/podcast/truth-about-real-estate-investing…/id1100488294

On Spotify: https://open.spotify.com/show/6Z8yd37AQfQI5DK0J0Xwzz

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/the-truth-about-real-estate-investing-for-canadians

Audible: https://www.audible.ca/podcast/The-Truth-About-Real-Estate-Investing-for-Canadians/B08JJS91WR

Youtube: https://youtu.be/ro2A_7ds-ao

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

  • Do your investments match your long-term goals?
  • Do you fully understand how your strategies work?
  • Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

  • Finding quality income properties
  • Structuring the legal and tax side
  • Managing the property manager and insurance provider
  • Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.


Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto


Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

From False Start to 5 Duplexes, a Ski Chalet, and Ground-Up Development: How Increasing Complexity Drives Returns Today

 

In 2003, a Canadian couple was eager to invest in real estate. They joined REIN, took the quick start weekend course, and learned the basics. But like many would-be investors, they stalled before buying their first property. The perceived barriers felt too high. Looking back, they admit that 2003 was an incredible buying opportunity — one they completely missed.

Not Understanding Hard, Scarce Assets and the Monetary System

By 2009, they finally took the plunge, buying a two-bedroom townhouse in Windsor. But their understanding of real estate was incomplete.
They knew about cash flow and mortgage paydown, but they didn’t grasp the third wealth driver: equity appreciation — especially how it’s tied to monetary policy and money printing.

After the 2008–2009 financial crisis, central banks responded with massive money creation. This was the starting gun for one of the greatest real estate bull runs in history. But at the time, they didn’t see it. Nervous about prices and the economy, they sold the townhouse for a small loss. Today, that same property would likely be worth four times as much.

The Comeback: Five Duplex Conversions in 15 Months

It wasn’t until 2017 that they committed fully. Inspired by re-reading Real Estate Investing in Canada while on vacation, they bought five single-family homes in Cobourg, Ontario, and converted them into duplexes — all in just 15 months.

The strategy worked. They targeted “awesome assets in awesome locations” — downtown, near the beach, and within walking distance to top schools. At the time, purchase prices of $420K plus $60–80K in renovations could be refinanced for $550K, enabling them to recycle capital quickly.

When the Math No Longer Works

Fast forward to today: those Cobourg properties are still owned, but high interest rates and today’s pricing have changed the picture. Two are cash-flow positive; four are not. With purchase prices now in the $750K–$850K range and renovations easily hitting $150K, new acquisitions simply don’t make sense.

The conclusion is blunt: If the spreadsheet doesn’t show positive cash flow after all costs, it’s not worth doing.

Pivoting to Lifestyle-Driven, Scarce Asset Investing

The answer wasn’t to quit real estate — it was to pivot.
The focus shifted to properties that are not only financially sound but also scarce and personally meaningful. That led to purchasing a luxury six-bedroom, ski-in/ski-out short-term rental in Mont-Tremblant.

Why Tremblant? Regulatory clarity, year-round demand, and true scarcity. There are only about 25 six-bedroom-plus STR properties on the mountain. The property commands up to $5,000 a night during peak season, and underwriting ensures it breaks even after all costs — property management, maintenance, and repairs — while serving as a vacation home.

The Next Step: Ground-Up Development

With the numbers no longer working for simple buy-and-hold rentals, the next logical move was into more complex, higher-return projects. The latest venture is a ground-up commercial development in Southwestern Ontario — a leap that combines market knowledge, a trusted partnership, and years of experience managing risk.

It’s part of a broader investment philosophy: as markets change, so must the investor. Where once a basic duplex conversion could deliver solid returns, today’s environment often requires greater complexity, higher risk, and more creativity to make the math work.

Looking Ahead: More Complexity, More Opportunity

The portfolio now spans:

  1. Five duplex conversions in prime Cobourg locations
  2. A luxury ski-in/ski-out short-term rental in Mont-Tremblant
  3. A ground-up commercial development project underway

There’s also an eye on U.S. real estate for its landlord-friendly laws, better cash flow potential, and diversification benefits.

The core philosophy remains the same: own hard, scarce, uncorrelated assets — a private business, quality real estate in prime locations, and Bitcoin.

In a market where the easy wins are gone, this journey is a reminder that the math matters, scarcity wins, and adaptability is the real competitive edge.

Or… You Could Skip the Complexity Entirely

Not everyone wants to take on $2-million luxury ski rentals or ground-up development projects that require years of work, carry substantial risk, and often feel like another full-time job.

That’s why there’s SHARE — the alternative for Canadian investors who want:

  • Positive cash flow from day one
  • Low-interest financing
  • Passive, done-for-you investing in landlord-friendly U.S. markets

With SHARE, you get the benefits of owning income property without the headaches of sourcing deals, managing renovations, or dealing with tenants. Your investment works for you from day one — simply, securely, and profitably.

Learn more and get started today at http://iwin.sharesfr.com

To Listen:

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

  • Do your investments match your long-term goals?

  • Do you fully understand how your strategies work?

  • Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

  • Finding quality income properties
  • Structuring the legal and tax side
  • Managing the property manager and insurance provider
  • Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.


Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto


Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.