From Zero to Full-Time Trader: How Anderson Carter-Griffith Built the Skill, Then Built the Wealth 

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Recorded: March 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Anderson Carter-Griffith

Anderson Carter-Griffith had never bought a stock when he arrived in Canada. 

He came over from Barbados on a hotel recruitment program—one of 100 selected from thousands who showed up for the chance. He worked hospitality, went to culinary school, ran a catering business out of Scotiabank Arena, and eventually started delivering DoorDash on the side.

The DoorDash gig was not an accident. It was a strategy.

Today, Anderson gets paid full-time to trade. He manages a professional trading desk, coaches everyday investors on options strategies, and parks his market gains into a family real estate portfolio in Barbados—which is why he is a guest on a real estate show. But the story worth telling is the trading journey. Because it started from nothing, and it followed a path almost anyone can take.

The Rule That Changed Everything: Never Trade Your Own Income

When Anderson decided to learn trading seriously, he made one non-negotiable rule for himself: the money going into his brokerage account could not be money he needed to live.

So he delivered DoorDash—every day, winter and summer—and used only those earnings to fund his trading account.

“I recommend you come to trading with what I call disposable income. It’s crazy to me that people use their rent money.”

That discipline kept him in the game long enough to actually learn it. Most people who blow up their trading accounts do so because a losing trade isn’t just a financial loss—it’s a crisis. When the money you are trading is money you can afford to lose, you make clearer decisions.

It’s the same principle veteran investors apply to leveraged investing: you don’t use capital you cannot afford to work with. The position size has to let you sleep at night.

🎧Listen to the full podcast

Step 1: ETFs First. Always.

Anderson didn’t start by picking stocks. He started with ETFs—broad, diversified funds that track entire sectors.

The reason is simple: ETFs teach you how sectors move without the noise of individual company risk. And once you understand that, you can lift the hood.

“I started with ETFs. Then I dug deeper under the hood, looked at the top 10 holdings, and as my capital and experience grew, I started picking up those individual companies.”

Today his long-term portfolio reflects that progression:

  • 40% Tech: Apple, Microsoft, Tesla, Nvidia, Palantir
  • 60% Diversified: Johnson & Johnson, Eli Lilly, UnitedHealth, Enbridge, TD, Royal Bank

He also uses “covered calls” on top of those holdings—a strategy that generates income from stocks you already own, effectively turning any position into a dividend-paying asset. For investors who want their money working without constant attention, this is worth understanding.

Step 2: Swing Trading — Investing That Fits Around a Job

Before Anderson was trading full-time, he was swing trading on his phone in thirty-minute windows—before work and at market close.

A swing trade is a position held anywhere from overnight to a few months. It is slower, less stressful, and far more appropriate for someone who still has a job, a family, and a life.

“If you sit and watch charts every minute and you’re not trained for it, your emotional and mental bandwidth is toast in about half an hour.”

This is where Anderson started coaching others. His company, The Trader Desk, teaches six core options strategies built around this model: put on a trade in the morning, check your phone mid-day, and let it run. No screen-watching. No emotional rollercoaster.

The first strategy he teaches is option spreads—not naked puts. The distinction matters. With an option spread, you know exactly how much you can lose before you enter the trade. Your downside is defined. For someone trading with genuinely disposable income, that structure makes the learning process feel manageable instead of terrifying.

The goal he sets for new students: replace one day’s income per month from trading. Not quit your job. Not get rich fast. One day. Then build from there.

Step 3: Professional Trading — Getting Paid to Trade Someone Else’s Capital

The final stage in Anderson’s journey was joining a trading firm as a professional—meaning the firm provides the capital, Anderson trades it, and he earns a percentage of the returns.

He now trades during New York Stock Exchange hours (9:30 a.m. to 4:00 p.m.) from a seven-monitor setup, and also trades futures in the early morning when the London and New York sessions overlap—a window he calls “the switch-on,” when institutional money floods the market and volatility spikes.

The firm’s rule: be “flat” by the end of every day. No overnight positions. It is a discipline that eliminates the risk of waking up to a tweet or a headline that has moved the market against you while you slept.

“I had to go to work for a week in Barbados to make what I can make in a couple of hours here. Once I got a taste of it, I couldn’t believe people made money like this.”

Where the Money Goes: The Real Estate Connection

Anderson’s philosophy on trading profits is simple: get the fast-paced money out of the market as quickly as possible and park it somewhere safe and boring.

For him, that means real estate. His family owns eight buildings—16 apartments—in Barbados. It is a mix of long-term tenants and short-term Airbnb units (where rates run $300 to $1,000 USD/night depending on unit size). A property manager handles operations, and Anderson doesn’t touch it.

It’s the same logic successful business owners use: fast income funds patient assets. Trading cash flow—like employment income—gets deployed into stable real estate, a dividend portfolio, or insurance products that compound over decades.

The vehicle is less important than the principle: active income should be building passive assets, not just paying for lifestyle.

10 Questions Answered on Trading, Options, and Building Wealth

1. What is the safest way for a beginner to start trading?

Anderson recommends starting with ETFs (Exchange-Traded Funds) rather than trying to pick individual stocks. By looking “under the hood” of ETFs, beginners can learn how different sectors move without the high risk of single-company exposure.

2. What is the biggest mistake new traders make?

Trading their rent or grocery money. Anderson built his initial trading account by delivering for DoorDash every single day. Using strictly disposable income removes the emotional panic of losing essential funds, which is when most new traders blow up their accounts.

3. What is “swing trading” and is it good for people with 9-to-5 jobs?

Swing trading involves holding a trade anywhere from overnight to several months. Anderson highly recommends this for people with full-time jobs because it doesn’t require watching the screen all day—you can simply check your positions for 30 minutes in the morning and 30 minutes at the close.

4. Why do professional day traders close all their positions by the end of the day?

Professional prop traders are required to be “flat” (holding zero positions) at the end of the day to eliminate overnight risk. This ensures they don’t wake up to massive losses caused by unexpected after-hours news, geopolitical events, or sudden market shifts.

5. Why are “option spreads” safer than selling “naked puts”?

While some strategies teach selling naked puts, Anderson warns against this because it requires massive upfront capital and exposes you to assignment risk if the trade goes against you. Option spreads, on the other hand, have a strictly defined, limited downside risk so you know exactly what your maximum loss is before entering the trade.

6. Can you turn a non-dividend stock into a cash-flowing asset?

Yes. Anderson uses an options strategy called “covered calls” to generate income on regular stocks he holds in his long-term portfolio. This effectively turns any standard stock into a dividend-producing asset.

7. How much money do you need to start trading options?

You can realistically start trading with as little as $1,000. The mechanics and core strategies of options trading are exactly the same whether you are trading a $1,000 account or a $10 million account; it simply becomes a matter of scaling the number of contracts you buy.

8. What is the “crossover” in the stock market?

The crossover is a highly volatile, volume-heavy period around 8:00 AM to 9:30 AM EST when the London trading session overlaps with the pre-market New York session. This is when institutional money (the “whales” and hedge funds) flood the market, creating prime opportunities for professional traders.

9. What should day traders do with their market profits?

Anderson’s core philosophy is to pull fast-paced money out of the market as quickly as possible and park it in safe, boring assets. He moves his trading gains into a stable dividend portfolio and hard real estate to preserve his wealth.

10. How does trading income complement real estate investing?

Trading is active income, while real estate is a patient, long-term asset. Anderson uses his active trading profits to expand and support his family’s real estate portfolio of 16 long-term and short-term rental apartments in Barbados, creating a diversified, multi-generational wealth engine.

🎧Listen to the full podcast

Connect with Anderson 

Anderson offers one-on-one coaching through The Trader Desk. Sessions are tailored to your pace and your level — whether you’re starting with $1,000 or $100,000, the strategies are the same. 

Email: thetraderdesk@outlook.com — include your name and phone number and he’ll get back to you. 

F

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/he-funded-his-trading-with-doordash-now-hes/id1100488294?i=1000755092186

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/He-Funded-His-Trading-With-DoorDash–Now-Hes-a-Professional-Trader-e3gclq0 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/eee14026-efb7-4573-9c31-860d65ad9bcf/the-truth-about-real-estate-investing-for-canadians-he-funded-his-trading-with-doordash-now-he%27s-a-professional-trader

Audible: https://www.audible.ca/pd/B0GSGWXJQZ?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/hsvpNLnabHg

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

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.

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.

How Canadians Can Win in U.S. Real Estate in 2026 (Without Betting on Appreciation) 

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Recorded: March 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Glen Sutherland

For the last few years, many investors looked like geniuses simply by buying properties and riding the wave of massive market appreciation. But as the market shifts in 2026, the days of banking on property values going up 10% to 20% every single year to save a bad deal are over. 

If your U.S. real estate investment only works because you are counting on appreciation, you are gambling, not investing. 

This week on The Truth About Real Estate Investing for Canadians, I sit down with Glen Sutherland, a full-time real estate investor, educator, and host of the Canadian Investing in the U.S. podcast. 

For nearly a decade, Glen has helped Canadians break into U.S. real estate. From distressed single-family homes to large multifamily projects, Glen has built scalable systems that allow him to invest entirely remotely. In fact, he rarely even visits his properties in person! 

Here is how Glen is successfully navigating the 2026 market and how Canadians can legally and profitably invest south of the border. 

4 Key Takeaways from This Episode: 

1. Appreciation Is a Bonus, Not a Strategy 

Markets move in cycles. While some markets are currently showing signs of recovery and improving rent rates, relying on future appreciation in your deal analysis is a highly risky play right now. Instead, Glen focuses on markets where the numbers make sense from day one, driven by strong employment and high-paying jobs, like the aerospace and tech industries moving into Huntsville, Alabama. 

2. Force the Appreciation 

If you want to mitigate risk, you need to force the value of the property yourself. Glen’s core strategy involves buying highly distressed properties—the kind of properties that banks and realtors won’t even touch—renovating them, and then refinancing or flipping them. By doing the heavy lifting upfront, you manufacture your own equity. 

3. Remote Investing Requires Ruthless Systems 

You don’t need to cross the border to be a successful U.S. investor, but you do need bulletproof systems. Glen operates his entire business from Canada using detailed Standard Operating Procedures (SOPs), virtual assistants, and strict checklists. His biggest piece of advice? Redundancy. Always have two property managers and multiple contractors available in any city you invest in, because life happens, and you don’t want to be left stranded when a team member leaves. 

4. The Power of “Subject-To” Investing 

The U.S. offers creative deal structures that are simply unavailable or highly restricted in Canada. One of Glen’s favorite strategies is “Subject-To” (Sub2) investing, where you take over an American’s existing mortgage, allowing you to secure incredibly cheap, locked-in interest rates while taking over the deed to the property. 

If you are a Canadian investor looking to escape low yields and difficult tenancy laws by diversifying into the U.S. market, you need to hear this episode. 

🎧Listen to the full podcast

You can learn more about Glen Sutherland and his coaching program at www.canadianinvestingintheusa.com. 

10 Real Estate Questions Answered in This Episode 

1. Is appreciation a reliable real estate investing strategy in 2026? 

No. Glen warns that if you need appreciation to make your deal numbers work, it is far too risky in today’s market. Appreciation should always be treated as a bonus, not a requirement. 

2. What is forced appreciation in real estate investing? 

Forced appreciation means proactively increasing a property’s value rather than waiting for the market to go up. Glen does this by purchasing heavily distressed properties at a massive discount, fully renovating them, and then refinancing based on the new, higher value. 

3. Can Canadians invest in U.S. real estate without visiting the properties? 

Absolutely. Glen often goes through the entire purchase, renovation, and sale process without ever physically stepping foot on the property. This is achieved by building a strong local team of property managers and contractors, and managing them through strict checklists and systems. 

4. What is a “Subject-To” (Sub2) real estate deal? 

Subject-To investing is a creative financing strategy popular in the U.S. where an investor takes over the deed of a property while leaving the seller’s original mortgage in place. This allows the investor to capitalize on the seller’s extremely low, previously locked-in interest rate. 

5. Why is redundancy important in remote real estate investing? 

In real estate, you are highly dependent on people (contractors, property managers, etc.). If your sole contractor quits or goes out of business, your project stalls. Glen recommends building redundancy—having backup property managers and multiple contractors—in every market you invest in to protect your business. 

6. Do you need a U.S. Social Security Number or Visa to invest in the U.S.? 

No. While having an E2 Visa, a U.S. driver’s license, or an SSN can be helpful for certain types of U.S. bank lending or tax structures, you do not strictly need any of them to begin investing and buying property in the United States. 

7. Why do some investors prefer large multifamily buildings over single-family homes? 

Multifamily buildings offer powerful economies of scale. Instead of dealing with multiple property managers across scattered single-family homes, you can manage 100 units under one roof, standardize all the paint and materials, and dramatically increase the building’s value simply by raising rents slightly across the board. 

8. What is the biggest challenge of investing in large multifamily properties? 

The speed of money. While large multifamily deals can generate significant long-term wealth, the operators are typically paid last in the capital stack. Single-family homes allow for a much faster turnaround of your capital (e.g., 3 to 6 months) to generate quick income. 

9. How do virtual assistants (VAs) help real estate investors? 

VAs can manage repeatable tasks such as bookkeeping, uploading podcasts, or running deal analysis spreadsheets based on standard operating procedures (SOPs). This frees up the investor’s time to focus on high-level strategy and acquisitions. 

10. What is the biggest regret of aspiring real estate investors? 

According to Glen, the biggest regret new students have is that they waited too long to start. Many realize they could have quit their jobs years ago if they had just taken action earlier instead of sitting on the sidelines. 

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/how-canadians-can-win-in-u-s-real-estate-in-2026-without/id1100488294?i=1000753354383

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/How-Canadians-Can-Win-in-U-S–Real-Estate-in-2026-Without-Betting-on-Appreciation-e3fu2lc 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/4636ffa0-a58c-40ed-a1ac-b5855504419e/the-truth-about-real-estate-investing-for-canadians-how-canadians-can-win-in-u-s-real-estate-in-2026-without-betting-on-appreciat

YouTube: https://youtu.be/KEjIDSWjmEY

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

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.

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.

70 Properties, Private Money, and a Mental Breakdown: The Truth About Scaling Real Estate 

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Recorded: February 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Rosna Arora

It is the dream sold on every real estate stage: scale fast, use private money, and build a massive empire. 

But what happens when the market stops cooperating? What happens when the music stops and you are dangerously over-leveraged? 

This week on The Truth About Real Estate Investing for Canadians, I sit down with my friend Rasna Arora. Rasna built an incredible $50 million real estate portfolio consisting of 70 properties. She came from the same real estate investment network I did (led by Don Campbell), hired one of the most expensive coaches in Canada, and even became a coach herself at Blackheart University. 

But her aggressive scaling relied heavily on private, hard money loans. 

The Perfect Storm 

When COVID hit, the dominoes started to fall. Renovations stalled, material and labor costs skyrocketed, and refinances completely froze. Meanwhile, the renewal fees on her private loans began stacking up. 

In the middle of this crisis, Rasna’s mortgage advisor told her to just borrow more hard money loans to survive. (Food for thought: that same mortgage professional, Claire Drege, is now personally and professionally bankrupt and has been handed a lifetime ban from the mortgage and securities industries). 

Rasna received terrible advice from a professional she trusted. But instead of digging a deeper hole and trapping more private lenders, she made a different choice—one that ultimately cost her everything. 

A Lesson in Integrity and Leverage I will warn you right now: there is no fairytale ending to this episode. 

This is not a show about Lamborghinis and hype; this is an honest, raw conversation about the dark side of real estate investing. It is a masterclass in integrity, morals, and ethics, and a deep dive into the severe mental health breakdown that can happen when scaling with over-leverage goes wrong. 

3 Key Takeaways from This Episode: 

  • The Danger of Hard Money: Private money is a tool, but when it is used excessively to scale without proper cash flow or viable exit strategies, it becomes a trap. 
  • The Mental Toll: Real estate is a business with real consequences. Carrying a $50M over-leveraged portfolio while facing a market freeze takes a massive toll on your mental health. 
  • Cash Flow over Ego: I live by the quote from Winston Churchill: “Those who fail to learn from history are doomed to repeat it”. During the 2007-2008 financial crisis, leverage is what killed developers. This is exactly why I have always focused on “boring,” positive cash flow when discussing investments. 

If you invest in real estate—and especially if you use private hard money loans—you need to hear this episode. 

🎧 Listen to the full episode here

Disclaimer: This story is shared for educational purposes. I am not an accountant or a financial advisor. Please seek qualified professional advice for your specific situation. 

🎧 Listen to the full episode here

10 Real Estate, Leverage, and Hard Money Questions Answered in This Episode 

1. What is “hard money” in real estate investing? 

Veteran real estate investors use the term “hard money loans” to refer to private money borrowing. While private money can help investors scale a portfolio quickly, it becomes incredibly dangerous if the market shifts or projects stall. 

2. What are the risks of using private money to scale a portfolio? 

If market conditions change, you can get trapped. In Rasna’s case, when refinances froze and renovations stalled, the renewal fees on her private loans aggressively stacked up, leaving her dangerously over-leveraged. 

3. How did the COVID-19 pandemic impact real estate renovation projects? 

The pandemic created a perfect storm for active investors doing the BRRRR strategy by causing renovations to stall, material and labor prices to skyrocket, and refinancing options to completely freeze. 

4. What is the mental health impact of an over-leveraged real estate business? 

Holding a massive portfolio of 70 properties during a market freeze takes an immense mental toll, often leading to severe stress and mental health breakdowns. Real estate has a human cost when scaling goes wrong. 

5. Can mortgage professionals be punished for giving harmful advice? 

Yes. Erwin notes that Rasna’s former mortgage advisor, Claire Drege, faced severe consequences for her actions, including personal and professional bankruptcy, as well as a lifetime ban from the mortgage and securities industries. 

6. Should you borrow more hard money to cover existing debt? 

Generally, no. Rasna was advised by a trusted professional to take out more hard money loans just to survive her cash crunch, which is a dangerous strategy that often digs a deeper hole instead of solving the fundamental cash flow issue. 

7. Does hiring an expensive real estate coach guarantee success? 

No. Rasna came from a top real estate investment network, hired one of the most expensive coaches in Canada, and was even a coach herself at Blackheart University. Her story proves that even highly educated investors can lose everything if they rely on dangerous levels of leverage. 

8. Why do veteran investors prefer “boring” positive cash flow? 

History shows that high leverage is what kills developers and investors, as seen during the 2007-2008 financial crisis. Focusing on boring, positive cash flow ensures the investment is sustainable during market downturns. 

9. What historical lesson applies to today’s over-leveraged real estate market? 

Erwin quotes Winston Churchill: “Those who fail to learn from history are doomed to repeat it”. Investors must remember that excessive leverage is historically responsible for massive portfolio collapses. 

10. How can investors maintain a healthy work-life balance? 

Real estate investing should not become a stressful “second job” of managing tenants, toilets, and renovations that takes you away from your family. Investors should seek strategies that build wealth without sacrificing their nights, weekends, and peace of mind. 

Want to learn how to build wealth without the sleepless nights? 

We are big proponents of work-life balance and building wealth without sacrificing your weekends or taking on a “second job” of managing tenants and toilets. 

Join 10,000+ Canadian real estate investors who are already on my free newsletter to learn the latest and greatest strategies in the market. Go to www.truthaboutrealestateinvesting.ca and drop your email on the right-hand side to get on the list. 

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/70-properties-private-money-mental-breakdown-the/id1100488294?i=1000752564013

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/70-Properties–Private-Money–Mental-Breakdown–The-Truth-About-Scaling-Real-Estate-e3fnaf7 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/bab0622f-7bcf-4ae7-a209-51a409227821/the-truth-about-real-estate-investing-for-canadians-70-properties-private-money-mental-breakdon-the-truth-about-scaling-real-estate

YouTube: https://youtu.be/C58ugy__iKA

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

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.

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.

How a $14 Million Portfolio Evaporated: The Adam Kitchener Story

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Recorded: February 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Adam Kitchener

Folks, welcome back to the show. 

It is every real estate investor’s nightmare. You follow the rules, use the BRRRR strategy. Build a portfolio worth over $14 million. And eventually, you achieve what looks like financial freedom. 

And then, while you are on vacation in Thailand, your debit card stops working. 

You call the bank, and they tell you: The CRA has frozen everything. 

This week on The Truth About Real Estate Investing for Canadians, I sat down with Adam Kitchener. If you’ve been around the Hamilton/Ontario investing scene, you likely know Adam. He started investing in 2016, built a massive portfolio, and ran a property management company. 

But for the last three years, Adam has been fighting a war with the CRA that cost him almost everything. 

The Audit That Spiraled 

Adam shares the harrowing details of how a routine audit turned into a financial death spiral. It wasn’t about fraud or tax evasion. It started with simple misunderstandings, auditors asking why he didn’t charge HST on residential rent (you don’t) or asking if he had a cash register for his rental business. 

Despite having meticulous records, the CRA froze his personal accounts. Because he had personally guaranteed his mortgages (a common practice for investors scaling up), the banks saw the CRA judgment and pulled his funding. 

The “Asset Rich” Trap We talk a lot about being “Asset Rich, Cash Poor.” Adam’s story is the extreme version of this. He had millions in equity, but when the CRA froze his liquidity, he couldn’t service the debt or pay his contractors. 

He was forced to surrender properties to the bank to avoid further legal battles. He went from managing a $14M portfolio to working three jobs just to pay back his contractors, because Adam is a man of integrity who refused to let his tradespeople suffer for his tax battle. 

The Mental Toll I want to thank Adam for his vulnerability in this episode. He opens up about the darkness of losing his identity as a “successful investor.” He discusses the mental health toll, the suicidal thoughts, and the moment he realized that his net worth did not define his self-worth. 

The Rebuild: Renovation Solutions Adam is still standing. He realized that the “hustle” of property management and massive portfolios wasn’t the only way. He has returned to his roots, launching Renovation Solutions, a contracting business focused on helping other investors turn units over efficiently. He’s rebuilding, but this time with a focus on simplicity and bulletproof corporate structure. 

🎧 Listen to the full episode here

10 Real Estate Tax & Legal Questions Answered in This Episode 

1. Can the CRA freeze my bank account without notice?

Yes. Adam discovered his accounts were frozen only when his debit card was declined while on vacation in Thailand. The CRA stated they had sent a letter, but because he was traveling, he did not receive it in time to respond. 

2. Do landlords have to charge HST on residential rent in Ontario? 

No. Long-term residential rent is exempt from HST. However, Adam shares a story of an auditor specifically asking why he wasn’t charging HST on his rental income, highlighting the importance of having a knowledgeable accountant to defend you against auditor errors. 

3. What happens to my mortgages if the CRA sues me? 

If you have personally guaranteed your corporate mortgages (which is common for real estate investors), a CRA judgment against you personally can trigger a “default” clause with your lenders. Adam’s lenders called his mortgages not because he missed payments, but because of the CRA judgment. 

4. What is “Audit Insurance” and do investors need it? 

Audit insurance covers the professional fees (accountants and lawyers) required to defend you during an audit. Adam notes that defending himself cost thousands of dollars he didn’t have access to because his accounts were frozen. Having this insurance can prevent you from running out of cash during a dispute. 

5. Can a general accountant handle a complex real estate audit?

Adam advises against using a generalist. He stuck with a “good guy” accountant too long, but when the complex audit hit, the workload was overwhelming. He recommends upgrading to a specialist firm before you think you need one. 

6. How does “Separation of Church and State” apply to real estate assets?

Adam emphasizes the need to completely separate personal assets from business assets. Because he had assets in his personal name (and personal guarantees), the CRA was able to seize/freeze personal funds that strangled his business operations. Proper corporate structuring creates a firewall. 

7. Why would a bank call a mortgage if I’m making payments? 

Even if you have never missed a mortgage payment (as Adam hadn’t), lenders monitor your credit and legal standing. A substantial tax lien or judgment effectively kills your creditworthiness, causing lenders to view you as high-risk and call the loan. 

8. Is property management a scalable business model? 

Adam built a large property management company but found it difficult to scale profitably due to the high volume of “bosses” (landlords) and tenants. He eventually closed it to focus on his own portfolio, noting it is a tough, low-margin industry. 

9. What triggers a CRA audit for investors? 

While sometimes random, Adam suspects his audit was triggered by a discrepancy between a year of low taxable income (due to write-offs) followed by a year of high asset acquisition (refinancing). The CRA looks for lifestyle spend that doesn’t match reported income. 

10. How long does a CRA audit take? 

Adam has been dealing with this for three years. It is not a quick process. He warns that investors need the stamina and liquidity to survive a multi-year battle, as the CRA can move very slowly while your assets remain frozen. 

🎧 Listen to the full episode here

As always, thanks for listening (all 17 of you!), and keep hustling. If you’re not already on my free email list, you can join at: 

👉 www.truthaboutrealestateinvesting.ca 

(Add your name and email on the right-hand side.) 

That’s how you’ll hear about new episodes, webinars, and live events like the Wealth Summit, where in-person seats sold out in a week. 

Being on the list helps you avoid disappointment. More importantly, it helps you avoid financial losses and fraud. We’ve seen this with Fortress Developments, Epic Alliance, and others currently in hot water with the Ontario Securities Commission. Cons and frauds share common patterns, and learning to spot them early matters. 

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/how-a-%2414-million-portfolio-evaporated-the/id1100488294?i=1000749289818

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/How-a-14-Million-Portfolio-Evaporated-The-Adam-Kitchener-Story-e3ev1rq/a-acfg7bj  

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/a4641340-9cf8-466e-b59c-cff04e429c6e/the-truth-about-real-estate-investing-for-canadians-how-a-14-million-portfolio-evaporated-the-adam-kitchener-story

Audible: https://www.audible.ca/pd/B0GMY9X9W1?source_code=ASSGB149080119000H&share_location=pdp 

YouTube: https://youtu.be/I_GmtpWkkpU

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

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.

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 18 Income Streams to Zero: The Brutal Truth About “Passive” Real Estate Investing 

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Recorded: January 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Serena Holmes, Award-winning Marketing and Business Professional, Podcaster and Author

Folks, welcome back to the show. 

If you’ve been listening to me for a while, you know I am obsessed with control. I like to own the title. I like to control the bank account. I like to know that if everything hits the fan, I can drive to the property and change the locks. 

Today’s guest, Serena Holmes, is here to share a cautionary tale that proves exactly why control is everything. 

Serena is a powerhouse. She built and exited a multi-award-winning marketing agency, she’s a Realtor, an author, and the host of the Inspired to Invest podcast. But a few years ago, she did what many busy entrepreneurs do: she tried to move from “active” income to “passive” investments. 

She invested in syndicated mortgages. She did private lending. She diversified into 18 different income streams. 

And then? They all went to zero. 

We’re talking about the collapse of major operators (like the Windrose Group) where hundreds of investors lost millions. Serena is open, vulnerable, and incredibly smart about what went wrong and, more importantly, how she is rebuilding. 

If you are thinking about handing your money over to a “hands-off” operator, or if you are raising capital yourself and want to do it without ending up in court, you need to read this. 

🎧 Listen to the full episode here

10 Capital Raising & Risk Questions Answered in This Episode 

1. What happens when “Passive” Investing goes wrong? 

Serena shares the reality of investing in syndicated mortgages and unsecured promissory notes. She thought she was diversified with 18 streams of income, but when the operators failed (due to fraud, mismanagement, or market shifts), every single stream dried up. The lesson: Diversification doesn’t help if the underlying asset structure is flawed. 

2. What does “If you’re not first, you’re last” mean in lending? 

This is the golden rule of private lending. Serena explains that if you are not in the first mortgage position, you are likely in trouble when a deal goes south. Unsecured notes or second/third positions often get wiped out completely during a power of sale or bankruptcy. 

3. Can you trust a “Guaranteed” return? 

No. We discuss how operators who scaled too fast (buying 600+ homes in 6 years) couldn’t refinance quickly enough when rates spiked. If an operator promises high returns without explaining the risks or having the liquidity to back it up, run the other way. 

4. Why is “Control” the most important word in investing? 

Serena admits she “shot herself in the foot” by giving away control. When you own the property on title, you have options. When you are a passive investor in a limited partnership or a promissory note holder, you are at the mercy of the operator’s competence and ethics. 

5. What is the reality of the GTA Listing Market right now? 

Serena is an active Realtor in the Durham/Toronto area. She notes that sellers are still stuck in 2022 pricing. She has listings where sellers turn down offers, only to receive lower offers months later as the market continues to soften. The “hold and hope” strategy is hurting sellers right now. 

6. Is it worth suing to get your money back? 

Serena has spent between $40,000 and $50,000 in legal fees trying to recover funds, with little to show for it yet. She highlights the harsh reality of the Canadian legal system: it is expensive, slow, and often, the money is simply gone. 

7. Why are Canadian investors moving capital to the USA? 

We discuss the “capital flight” to the US. Serena notes that the US GDP is expected to grow twice as fast as Canada’s . Between landlord-friendly laws, the 1031 exchange (tax-deferred selling), and better cash flow, many of her clients are pivoting south . 

8. What is the “Wild West” of Capital Raising? 

There was a time (and still is) where people raised millions on Facebook with zero compliance. Serena now works with M1 Real Capital, coaching investors on how to raise capital legally, ethically, and responsibly. You can’t just take money from people without the right paperwork and disclosure. 

9. How do you spot a “Con Artist”? 

I shared a quote from the book The Confidence Game: “Con artist” is short for “Confidence Artist.” Serena shares a story about seeing a prominent operator who looked the part—tall, commanding presence, confident on stage—who eventually went bankrupt owing investors millions. Confidence does not equal competence. 

10. What is the best way to rebuild after a loss? 

Serena’s advice is to get back to basics. She is focusing on her active income, helping others avoid her mistakes through coaching, and planning to return to purchasing multifamily properties where she controls the asset and the operations . 

🎧 Listen to the full episode here

My Final Thoughts 

Folks, I have seen too many people lose their life savings because they chased a high interest rate on a piece of paper. 

Real estate is a fantastic asset class, but it is not magic. It requires due diligence. If you don’t understand where the yield is coming from, or if you don’t have your name on the title, you are taking a massive risk. 

Serena’s story is a powerful reminder that return of capital is far more important than return on capital. 

If you want to connect with Serena to learn about compliant capital raising or just to follow her journey, you can find her on Instagram at @serenaholmesofficial or listen to her podcast, Inspired to Invest . 

As always, thanks for listening (all 17 of you!), and keep hustling. 

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/from-18-income-streams-to-zero-a-real-conversation/id1100488294?i=1000748566542

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/From-18-Income-Streams-to-Zero-A-Real-Conversation-About-Risk-in-Real-Estate-e3eo0bg 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/e33922c4-8771-4520-b047-ec9d8c27b40b/the-truth-about-real-estate-investing-for-canadians-from-18-income-streams-to-zero-a-real-conversation-about-risk-in-real-estate

Audible: https://www.audible.ca/podcast/ITEM-NAME/B0GKXS1MCP?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/5t4Ht_vwq4o

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

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.

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 Corporate CFO to Personal CFO: A 2026 Wealth Reset (And Why I’m Buying Less Real Estate) 

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Recorded: January 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Winnie Tsang, Former CFO

Folks, welcome back to the show. 

If you’ve been listening to me for a while, you know I am a die-hard real estate guy. I’ve built an 8-figure portfolio, I’ve been a landlord for 20 years, and I’ve coached hundreds of investors. 

But recently, I’ve been asking myself and my clients a hard question: Is the return on investment worth the return on hassle? 

I’m currently dealing with a broken washer that’s only three months old but costing me $300 to fix, plus a non-paying tenant. For high-energy entrepreneurs, active real estate is still a goldmine. But for me, with a young family, I want my investments to be boring, passive, and profitable. 

That is why I brought Winnie Tsang on the show. Winnie is a former corporate CFO for massive companies like Rogers and Accenture who made a pivot. She’s now a partner at Open Concept Financial Group, acting as a “Personal CFO” for families. 

We talk about “financial jujitsu”—strategies like leveraged segregated funds and corporate-owned life insurance that allow you to build wealth without unclogging a single toilet. 

If you are sitting on retained earnings in your corporation or you’re tired of being a landlord, you need to read this. 

🎧 Listen to the full episode here

10 Money Questions Answered in This Episode (That Your Bank Won’t Tell You) 

1. Why are everyday investors diversifying away from local real estate? It’s about income diversification and resilience. Winnie notes that for many, real estate has turned cash-flow negative. By diversifying into other asset classes, you gain liquidity and options—allowing you to buy time, which is the only non-renewable resource.

2. What is the “Corporate Owned Life Insurance” tax hack? This is a game-changer for business owners (doctors, realtors, consultants). Instead of investing retained earnings in GICs (taxed at ~50%), you buy a whole life policy inside the corp. The death benefit eventually pays out to your shareholders (family) tax-free via the Capital Dividend Account. It transfers business wealth to personal wealth with massive tax efficiency. 

3. Why do people choose “inaction” when it comes to their wealth? Fear and a lack of clarity. Winnie explains that people often feel overwhelmed by choices (the “burden of choice”), so they do nothing. But inaction is a choice with consequences. A good plan gives you the clarity to make a move. 

4. What are “Leveraged Segregated Funds”? This is the strategy I wish I started 10 years ago. It involves using a smaller amount of cash (e.g., $2,500) to access a much larger loan (e.g., $50,000) to invest in the market. Because it’s a segregated fund, it often comes with downside protection, and the interest on the loan is tax-deductible. It amplifies the upside, similar to a mortgage on a house, but without the tenants. 

5. Why leave a high-paying Corporate CFO job to help families? Winnie spent years maximizing shareholder value for big companies, but the pandemic made her rethink her purpose. She realized that regardless of wealth level, families struggle with financial management, especially as they age. She wanted to apply that high-level strategy to everyday people. 

6. Why is an independent financial firm better than a bank advisor? No quotas. Winnie notes that independent firms don’t have to push “Product X” just because it’s the flavor of the month. They can assemble a bespoke solution using the best products from multiple institutions to actually serve the client’s goal, not the bank’s sales target. 

7. Is real estate actually “passive” income? No. We discuss how real estate is actually an active business, not a passive investment. True passive investing shouldn’t add stress to your life or take time away from your family. If you have to manage a property manager, it’s still work. 

8. Why is Estate Planning the most overlooked aspect of wealth? We avoid talking about death, but it’s the one certainty. Winnie points out that insurance is bought with your health and age; if you wait until you retire to plan your estate, it’s often too expensive or too late. Optimizing this early creates an exponential curve of growth for your legacy. 

9. How do cognitive biases hurt our investment returns? We suffer from “familiarity bias”—we buy real estate because our parents did, or because we made money on it once before. But doing the same thing when market conditions have changed (like high interest rates) leads to losses. You have to look at the objective data, not just what feels comfortable. 

10. What is the “Financial Jujitsu” approach? It’s about finding joy in figuring out how to make more money, work less, and pay less tax. It’s using the rules of the system (like the Capital Dividend Account or leverage) to maximize your returns with the least amount of effort. 

🎧 Listen to the full episode here

My Final Thoughts 

Folks, life is short. I want to spend my weekends with my kids, making slime and listening to Taylor Swift (don’t ask), not chasing rent payments. 

Real estate is a fantastic way to build wealth, but it isn’t the only way. If you are ready to look at your wealth holistically—insurance, investments, and estate planning—reach out to us. 

If you want to meet Winnie and hear more about these strategies, come to our Wealth Summit 2025. She’ll be there, and trust me, she’s way smarter than I am. 

Save the date

Wealth Summit 2026 · Hybrid (In-Person + Online) | Saturday, January 31st · 9:00 AM EST

Ready to make 2026 your smartest financial year yet? Join us for Wealth Summit 2026, where real estate, tax, and wealth-planning experts break down the proven blueprint for protecting and multiplying your wealth.

REGISTER HERE

Early-bird registration is now open — save 40% when you secure your spot early. Seats for the in-person experience are limited and always sell out fast.

Discover the frameworks, tax strategies, and legacy tools top performers use to stay ahead — no matter the market.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/from-corporate-cfo-to-personal-cfo-a-2026-new-year/id1100488294?i=1000747020836

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/From-Corporate-CFO-to-Personal-CFO-A-2026-New-Year-Wealth-Reset-for-Investors-e3eaa92

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/ae98b6ad-0ce8-463d-b88d-1c2bb2939ecc/the-truth-about-real-estate-investing-for-canadians-from-corporate-cfo-to-personal-cfo-a-2026-new-year-wealth-reset-for-investors

Audible: https://www.audible.ca/pd/B0GK9ZJS13?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/T-ULjlsjqrI

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

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.

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 Mortgage Masterclass: Why 2026 is the Year to Buy (and How to Hack CMHC Financing)

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Recorded: January 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Scott Dillingham, founder of LendCity

Welcome back to the show. I’ll be honest with you—I had some selfish questions today. 

Like many of you, I have mortgages coming up for renewal. I have variable rate mortgages that have been painful for the last couple of years. I wanted to know: Is this the bottom? And if I want to invest in the U.S., how hard is it really compared to the brain damage we deal with in Canada? 

To get the answers, I brought back the man who holds the record for the most appearances on this show: Scott Dillingham of LendCity. Scott is a rare breed—he owns mortgage brokerages in both Canada and the U.S., so he sees the data from both sides of the border without the fluff. 

We get into the weeds on interest rate predictions, the absolute carnage happening in the pre-construction condo market, and a massive “hack” for developers using the CMHC MLI Select program that I honestly hadn’t heard before. 

If you are sitting on the sidelines waiting for rates to drop further, or you’re tired of Canadian red tape and looking south, you need to read this. 

🎧 Listen to the full episode here

10 Real Estate Financing Questions Answered in This Episode 

1. Is it time to lock in a Fixed or Variable mortgage in 2026? 

Scott suggests sticking to the 5-year fixed or 5-year variable. He warns against the “3-year fixed specials” lenders are pushing right now. Why? Because banks want you renewing sooner when they anticipate rates might be higher again. If you want safety, lock in the 5-year fixed now while it’s in the high 3s or low 4s. 

2. Are interest rates going to drop further this year? 

Likely not much. Scott believes we are at the bottom. In fact, major banks are predicting rates might actually creep up by 0.25% by the end of the year,. If you are waiting for rock bottom, you’re probably standing on it right now. 

3. Why are pre-construction condo buyers in trouble right now? 

It is ugly out there. Scott is seeing appraisals come in drastically lower than the purchase price—e.g., bought for 900k∗∗,appraisedat∗∗700k,. Lenders won’t bridge that gap; the buyer has to come up with that $200k cash difference. If you can’t, you’re in a tough spot. 

4. What is the “Smart Developer Hack” for CMHC MLI Select financing? 

This is pure gold for developers. Instead of forcing affordable rents (which kills your cash flow in Ontario due to rent control), savvy investors are skipping the affordability criteria entirely. They focus on energy efficiency and accessibility instead. You get a 45-year amortization (instead of 50), but you get to charge market rents,. 

5. How much easier is it to get a mortgage in the U.S. vs. Canada? 

Scott says it is “infinitely” easier . In Canada, you provide tax returns, T4s, and blood samples. In the U.S., you can use DSCR (Debt Service Coverage Ratio) loans, where the property qualifies for the mortgage based on its rental income, not your personal income, . 

6. Is there a risk of U.S. banks failing? 

We hear about U.S. bank failures in the news, but for a borrower, it doesn’t matter. U.S. banks sell their mortgages on the secondary market almost immediately . If your bank fails, your loan is just sold to another lender. Your terms don’t change . 

7. Why are investors pivoting to Commercial Mortgages for residential properties? 

If you are hitting a “brick wall” with residential lending limits (e.g., hitting your debt-to-service ratio cap), commercial lenders have no limit . You can buy unlimited properties as long as the deal makes sense. Rates are similar (mid-4s to 5s), though fees are slightly higher , . 

8. Should you be wary of “B-Lender” fees? 

Yes. B-lenders offer easier qualification (using up to 60% of income for ratios), but the costs add up. You are looking at rates from 4.8% to 6.5%, plus a 1-2% lender fee and a broker fee, . It’s a tool, but it’s not cheap. 

9. How does the current U.S. political climate affect real estate? 

Love him or hate him, Trump is pushing for lower borrowing costs. He has authorized Fannie Mae and Freddie Mac to buy bonds to drive interest rates down , . This flood of liquidity is expected to drive U.S. housing prices up, making now a strategic time to buy before that appreciation hits . 

10. Why invest in U.S. properties through a Canadian brokerage? 

Scott owns brokerages on both sides of the border, meaning there are no “middleman” fees . Many Canadian brokers just refer you to a U.S. partner and take a cut. Working with a direct access broker saves you money and streamlines the chaos . 

🎧 Listen to the full episode here

My Final Thoughts 

Folks, the data is clear: the waiting game is over. Whether you are looking at distressed pre-con deals in Toronto (if you have the cash) or cash-flowing rentals in the U.S., the window to buy at the bottom is closing. 

Scott’s insight on the MLI Select program, taking a 45-year amortization to keep market rents, is exactly the kind of pragmatic, number-focused strategy we love on this show. Don’t let the government discount your cash flow if you don’t have to. 

If you want to reach out to Scott and his team for financing in Canada or the U.S., head over to LendCity.ca and check out their investor resources. 

As always, thanks for listening (all 17 of you!), and keep hustling. 

Save the date

Wealth Summit 2026 · Hybrid (In-Person + Online) | Saturday, January 31st · 9:00 AM EST

Ready to make 2026 your smartest financial year yet? Join us for Wealth Summit 2026, where real estate, tax, and wealth-planning experts break down the proven blueprint for protecting and multiplying your wealth.

REGISTER HERE

Early-bird registration is now open — save 40% when you secure your spot early. Seats for the in-person experience are limited and always sell out fast.

Discover the frameworks, tax strategies, and legacy tools top performers use to stay ahead — no matter the market.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/mortgage-market-update-for-2026-residential-commercial/id1100488294?i=1000746376200

On Spotify: https://open.spotify.com/episode/48ISuXhSJMguNaxK3d6Edy?si=bDedAZnXS3iQ9FyBP82CVw

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/9365d1eb-e5d2-432b-8bdc-9550f012f274/the-truth-about-real-estate-investing-for-canadians-mortgage-market-update-for-2026-residential-commercial-development-canada-usa-mexico

YouTube: https://youtu.be/CO36McC9rFo

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

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.

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 Lending Nightmares to Hotel Millions: Mike Rosehart’s Ultimate Pivot 

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Recorded: January 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Mike Rosehart, Real Estate Analyst and Investor

Welcome back to the show. We had a returning guest on, and honestly, if you’re looking for a masterclass on how to pivot when the market punches you in the face, this is it. 

Mike Rosehart is back, and he’s not just doing student rentals in London anymore. We’re talking about a massive shift. He’s acquired a couple of hundred units in the last 12 to 18 months, pushing his portfolio north of $50 million. 

But it wasn’t a straight line up. We get into the messy stuff—the private lending deals that went south, the foreclosures, and how he turned those disasters into a goldmine in the hospitality space. Mike openly shares the challenges, admitting he had lending deals where borrowers stopped paying for 11 months and he waited too long to take legal action. 

If you are serious about scaling or you’re stuck trying to make the numbers work in this high-interest environment, you need to pay attention to the “Hotel to Apartment” conversion strategy Mike breaks down. It is absolute fire. 

🎧 Listen to the full episode here

10 Real Estate Questions Answered in This Episode 

1. Why are smart investors pivoting from residential rentals to hotels and motels? 

The margins in residential multifamily are tight right now. Mike explains that in markets like Ontario, you might pay $180,000 to $200,000 per door for a multifamily unit. However, you can buy a hotel or motel for $60,000 to $70,000 per key. That is half or a third of the cost for the same physical square footage, offering a massive arbitrage opportunity. 

2. Can you convert a motel into a long-term residential apartment? 

Yes, and it’s a massive value to add. Mike notes that many motels already have kitchenettes or the infrastructure for them. By spending $10,000 to $15,000 per unit on renovations and getting a simple change of use zoning (often around $5,000), you can convert them into residential apartments that qualify for CMHC financing. 

3. What are the dangers of private lending in a correcting market?

We talk about the ugly side of lending. Mike shares how he had lending deals go sideways where he was in a second mortgage position during a market correction. The lesson? If you are in a second or third mortgage position or holding a promissory note, your capital might be worthless because the first mortgage and legal fees eat up all the equity. 

4. How do you automate a hotel operation to slash costs? 

Mike isn’t running these like it’s 1990. He fires the expensive staff and cuts the franchise flags immediately. He uses AI bots for front desk operations, automated digital locks with codes that expire, and independent contractors for cleaning. This cuts costs by 50% compared to traditional operators. 

5. Why would an investor buy a property in cash right now? 

While leverage is king, cash is speed. Mike recently bought a 50-unit property in Sarnia (The Village Inn) with cash because lender fees were too high and the timeline was too tight for environmental assessments and appraisals. The goal isn’t to stay in cash, but to secure the deal, stabilize it over 6-12 months, and then refinance to pull the capital back out. 

6. How does the “Lifetime Capital Gains Exemption” apply to hotels? 

This is a huge tax nugget. Because hotels are considered “active businesses” rather than passive rentals, you can potentially utilize the Lifetime Capital Gains Exemption (LCGE) when you sell the shares of the corporation. If structured correctly with a family trust, you could shelter millions in profit tax-free,. 

7. Is it easier to evict a non-paying guest in a hotel vs. a tenant?  

Mike highlights that in a hotel/motel environment, if a guest doesn’t pay, you can simply disable their door code or call the police for removal. You avoid the 8-11 month delays typical of the Landlord and Tenant Board (LTB) in Ontario. 

8. What should you look for when taking over a distressed property? 

You want absentee owners or tired operators. Mike bought a hotel from a 92-year-old operator who had zero online presence—no Booking.com, no Expedia, just a phone number. By simply modernizing the marketing and operations, the revenue lift is instant. 

9. Is the BRRRR method still alive in Ontario? 

It is, but you have to buy deep. Mike mentions that detached houses in London, Ontario, have fallen significantly—sometimes trading at half of what they were in 2022. If you can buy a detached house for land value (e.g., $240k), add a unit, and create a duplex, the numbers start to make sense again. 

10. Is real estate investing scalable without a massive team? 

Mike argues that bigger deals are actually easier to scale than small ones. He puts a “mentee” or operating partner into his larger hotel deals to live on-site and manage operations in exchange for equity. This allows him to scale to hundreds of units without personally managing every toilet fix. 

🎧 Listen to the full episode here

My Final Thoughts 

Folks, the market has changed. What worked in 2017 isn’t working today. You can’t just buy a pre-con condo and hope it goes up. You have to force appreciation. 

Mike is showing us that there is opportunity in the ashes of this correction. Whether it’s buying distressed notes, taking over foreclosures, or converting motels into housing, the deals are there for the people willing to do the work. He’s proving that “active business” income is the new path to cash flow in 2025. 

If you want to see what Mike is up to, check him out on Instagram at @mikerosheart or search for The Village Inn Sarnia to see his latest project. 

Save the date

Wealth Summit 2026 · Hybrid (In-Person + Online) | Saturday, January 31st · 9:00 AM EST

Ready to make 2026 your smartest financial year yet? Join us for Wealth Summit 2026, where real estate, tax, and wealth-planning experts break down the proven blueprint for protecting and multiplying your wealth.

REGISTER HERE

Early-bird registration is now open — save 40% when you secure your spot early. Seats for the in-person experience are limited and always sell out fast.

Discover the frameworks, tax strategies, and legacy tools top performers use to stay ahead — no matter the market.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/from-houses-to-hotels-a-real-life-monopoly-story/id1100488294?i=1000745436200

On Spotify: https://open.spotify.com/episode/48ISuXhSJMguNaxK3d6Edy?si=bDedAZnXS3iQ9FyBP82CVw

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/4b07e204-26bd-4242-8876-87dbaebb0c40/the-truth-about-real-estate-investing-for-canadians-from-houses-to-hotels-a-real-life-monopoly-story

Audible: https://www.audible.ca/pd/B0GH8LCLTB?source_code=ASSGB149080119000H&share_location=pdp

YouTube:https://youtu.be/5slXpuy5YV8

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

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.

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.

How a Canadian WealthGenius Coach Scaled a U.S. Multifamily Portfolio 

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Recorded: January 2026
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Canadian real estate investors are facing a harsh reality: rising prices, capped rents, and prolonged eviction timelines have fundamentally changed the risk profile of being a landlord in provinces like Ontario and British Columbia. 

In this episode, U.S. multifamily investor Thomas Lorini explains why he shifted capital from Canadian rentals to U.S. markets — particularly Ohio — and how landlord-friendly laws, DSCR financing, and value-add multifamily strategies have restored predictability and cash flow. 

Ohio offers a combination of affordability, population density, diversified employment, and strong landlord rights. Properties that would cost over $1 million in Ontario can still be acquired for under $100,000 in parts of the Midwest, with eviction timelines measured in weeks rather than years. 

Thomas also breaks down common Canadian concerns: 

  • Cross-border taxation and entity structuring 
  • Financing without Canadian income limits 
  • Section 8 housing myths vs reality 
  • Currency risk and U.S. dollar income 

For investors seeking boring, predictable real estate again, this conversation outlines why many Canadians are quietly diversifying into U.S. residential and multifamily assets. 

🎧 Listen to the full episode here

Fast Facts on USA Investing for Canadians 

Why are Canadians investing in U.S. real estate instead of Canada?

Because U.S. markets offer stronger landlord rights, lower prices, and faster legal resolution compared to rent-controlled Canadian provinces.

What is DSCR financing and why does it matter for Canadians?

DSCR loans are based on property cash flow rather than personal income, allowing Canadians to scale portfolios without income caps.

Why is Ohio attractive for real estate investors?

Ohio combines affordability, population scale, diversified employment, and landlord-friendly laws with strong cash-flow potential.

How long does an eviction take in Ohio?

Most non-payment evictions are resolved in 3–6 weeks, compared to 8–18 months in Ontario.

Is Section 8 housing risky for investors?

It can be profitable when managed correctly, but outcomes depend heavily on location, property management, and tenant mix.

Do Canadians need U.S. credit to invest in U.S. properties?

No. Many lenders underwrite the property itself rather than the investor’s personal credit history.

Are U.S. interest rates higher than Canada’s?

Yes, but U.S. loans often allow repeat financing and scalability that Canadian lenders restrict.

Does the exchange rate hurt Canadian investors?

While entry costs are higher, income is earned in U.S. dollars, often offsetting currency risk over time.

Is multifamily better than single-family investing?

Multifamily offers operational scale, professional management, and forced appreciation through value-add strategies.

🎧 Listen to the full episode here

Save the date

How to Sell Investment Property for Maximum ROI. Online-Only Live Masterclass | Tuesday, January 13th · 8:00 PM EST

If you’re thinking about selling in 2026, join us on January 13th at 8 p.m. Eastern for our free IWIN training: “How to Sell an Investment Property for Maximum ROI.” 

REGISTER HERE

We’ll walk through: 

  • Real examples of deals that sold vs. deals that pivoted to Plan B. 
  • How to price properly in a market full of bank sales and estate sales. 
  • Tenant strategies that make your property more attractive — or at least not a liability — when you hit MLS. 

In this market, you don’t have to get crushed. You just have to be smarter than the average seller. 

Wealth Summit 2026 · Hybrid (In-Person + Online) | Saturday, January 31st · 9:00 AM EST

Ready to make 2026 your smartest financial year yet? Join us for Wealth Summit 2026, where real estate, tax, and wealth-planning experts break down the proven blueprint for protecting and multiplying your wealth.

REGISTER HERE

Early-bird registration is now open — save 40% when you secure your spot early. Seats for the in-person experience are limited and always sell out fast.

Discover the frameworks, tax strategies, and legacy tools top performers use to stay ahead — no matter the market.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/how-a-canadian-wealthgenius-coach-scaled-a-u/id1100488294?i=1000743970414

On Spotify: https://open.spotify.com/episode/3tjfSgCpuC8m9bsslhyZYw?si=hObKhKMVQCyec2I7uexaxA

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/2ae2ffad-e966-4889-bd70-e2e7f12052f2/the-truth-about-real-estate-investing-for-canadians-how-a-canadian-wealthgenius-coach-scaled-a-u-s-multifamily-portfolio

Audible: https://www.audible.ca/podcast/ITEM-NAME/B0GF4Q8PGT?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://www.youtube.com/watch?v=TJoOCVoGnzA

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

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.

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.

How to Sell a Tenanted Property in 2026 

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Recorded: December 2025
Guest:️ Tim Hong, Property Manager specializing in selling and managing tenant-occupied properties.
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Selling an investment property in Ontario in 2026 is not the same game it was in 2021.

If you’re an investor in markets like Hamilton, Kitchener–Waterloo, or the GTA, you’re facing more listings, tougher financing, and smarter buyers. At the same time, interest rates are still high enough to squeeze cash flow, and the Landlord and Tenant Board remains a risk you want to avoid at all costs. 

In a recent episode of The Truth About Real Estate Investing for Canadians, I sat down with veteran investor, realtor, and property manager Tim Hong to talk about exactly what’s happening on the ground — and what smart investors are doing instead of panicking.  

Inventory Is Up 50–60%… But Prices Are Range-Bound 

Tim started by pulling fresh stats from his core markets: 

  • Kitchener–Waterloo: active listings are up from about 810 in November 2023 to roughly 1,296 today — a 60% jump. 
  • Hamilton: inventory is up from ~1,410 to 2,078 active listings, a bit more than a 50% increase. 

That’s a huge shift in supply, yet prices haven’t completely collapsed. From the February 2022 peak, we’re still roughly 20–30% down, but for the last three years prices have mostly been range-bound, bouncing up and down within a band.  

The takeaway: 

  • If you’re listing your property now, understand you’re competing in a crowded marketplace. 
  • Buyers have time and options. Conditions are back. So are offers conditional on the sale of the buyer’s home. 

Power-of-Sale and Estate Sales Are Setting the Bar 

When I pulled comparables recently, I saw more power-of-sale and bank-owned listings than at any time since I became a realtor in 2010. I also saw a bank-owned Hamilton Mountain bungalow duplex that sold for around $1.2M at the peak get resold for roughly $720,000 after the bank took it back. 

That’s a 40%+ haircut. 

These types of listings — bank sales and estate sales — are often: 

  • Aggressively priced to clear quickly. 
  • Heavily influencing buyers’ expectations on what a “deal” looks like. 

If you’re a regular investor trying to sell a tenanted duplex, you’re competing against those numbers, whether you like it or not.

Why Single-Family Homes Sell Faster Than Duplexes Right Now

Tim sees a big difference between “obvious rental properties” and end-user homes: 

  • Legal duplexes, triplexes, and vacant student rentals: 
  • Investors are cautious. 
  • Financing is tighter and interest rates are higher. 
  • Offers are often below what sellers want. 
  • Single-family homes for end users: 
  • Bigger buyer pool. 
  • Still seeing healthy activity and occasional multiple offers, depending on location and price. 

Investors have no sense of urgency right now. They’ll buy only if the numbers are compelling. That means if your exit strategy relies on another investor paying top dollar, you may need to adjust your expectations — or your strategy.  

Plan A vs Plan B: Sell or Re-Rent? 

For many of Tim’s clients, the starting plan was: 

  1. Tenant leaves. 
  2. Touch up the property. 
  3. List it for sale. 

In several cases, the market response was underwhelming: little activity, weak offers, or no offers at all. 

At that point, Tim sits down with the investor and runs the numbers on Plan B: 

  • What can this property realistically rent for with a proper tenant-screening process? 
  • What does cash flow look like at today’s interest rate? 
  • Are you willing to hold for another 3–5 years? 

Often, the investor decides that re-renting is the better financial move. 

In one case, an investor was set on selling a property with long-term tenants paying below-market rent. Once they saw the projected sale price and tax implications, they weren’t excited. 

Tim approached the tenants directly, explained the situation, and negotiated a new lease at a higher rent that was still below market. The result? 

  • The investor kept the property. 
  • Cash flow increased by about $560 per month. 
  • The tenants gained security and avoided the uncertainty of a new owner.  

That’s the power of creative negotiation and treating selling as one option, not the only option. 

The Resilience of University Student Rentals 

While many asset classes are feeling pain, university-area student rentals have quietly been one of the most resilient strategies over the last decade. 

Why? 

  • Enrollment tends to increase during economic downturns. 
  • Universities have more stable, diversified demand than some private colleges that leaned heavily on international students. 
  • Student rentals naturally build in tenant turnover every 2–3 years, letting landlords reset rents to market regularly. 

College-focused markets tied to international enrollment — think Conestoga and similar schools — have seen dramatic drops and oversupply. But university zones around schools like Waterloo, Laurier, McMaster, and others are still seeing strong demand from quality students who want clean, well-managed housing.  

Bill 60 and the Future of Selling Tenanted Properties 

We also talked about Bill 60 and what it could mean for investors: 

  • Shorter timelines for non-payment of rent (N4 going from 14 days to 7). 
  • Requirements for tenants to pay 50% of outstanding rent into the system if they want to raise maintenance issues at a hearing. 
  • Possible relief from compensation requirements if you give 120 days’ notice to a tenant for a buyer’s own use. 

None of this is a magic fix. But it may tilt the playing field slightly back towards responsible landlords who follow the rules. 

The safer strategy remains the same: avoid the Landlord and Tenant Board completely by screening tenants properly, communicating clearly, and handling issues early. 

Tenant Screening: Why Tim Hasn’t Been to the LTB in Two Years 

Tim’s property management company hasn’t had to attend the LTB in two years. His process is simple but strict: 

  • Use SingleKey for credit and application processing. 
  • Use OpenRoom to check for existing court orders. 
  • Verify employment, income, and current landlord through independent searches. 
  • Watch how tenants communicate and follow instructions. 

If someone no-shows a viewing without notice, asks for four parking spots on a property with one, or can’t be bothered to read the ad, they’re disqualified. 

Is it harsh? Maybe. 

Is it effective? Definitely. 

If you want high-quality, long-term tenants who pay on time and treat your property like a home, you need to raise the bar. 

Should You Buy Vacant or Tenanted Right Now? 

Given longer vacancy times for new listings and the sheer number of options tenants have, Tim makes a point many investors miss: 

  • If you’re buying locally and want a relatively hands-off experience, consider buying a property with a good, paying tenant in place at a fair rent — as long as you can verify their history and lease. 
  • If you buy vacant, be prepared for two months (or more) of vacancy, plus screening, showings, and uncertainty. 

In today’s market, time is money, and two months of lost rent plus your own time and stress can eat up a lot of the “deal” you thought you were getting.  

🎧 Listen to the full episode here

Final Thoughts: Hold, Sell, or Pivot? 

If you own investment real estate in Ontario right now, you don’t need fear. You need a clear decision-making framework: 

  1. Check your numbers honestly. Can you carry the property for another 3–5 years if you re-rent at realistic market rents? 
  1. Know your asset. Is it a quality property in a solid location, or is it a weak property that only looked good in a spreadsheet? 
  1. Understand your buyer. Are you selling to an end user or another investor? The strategy, staging, and pricing are different. 
  1. Have a Plan B. If the right offer doesn’t come, be ready to re-rent, renegotiate with tenants, or refinance instead of selling at a painful discount. 

Save the date

How to Sell Investment Property for Maximum ROI. Online-Only Live Masterclass | Tuesday, January 13th · 8:00 PM EST

If you’re thinking about selling in 2026, join us on January 13th at 8 p.m. Eastern for our free IWIN training: “How to Sell an Investment Property for Maximum ROI.” 

REGISTER HERE

We’ll walk through: 

  • Real examples of deals that sold vs. deals that pivoted to Plan B. 
  • How to price properly in a market full of bank sales and estate sales. 
  • Tenant strategies that make your property more attractive — or at least not a liability — when you hit MLS. 

In this market, you don’t have to get crushed. You just have to be smarter than the average seller. 

Wealth Summit 2026 · Hybrid (In-Person + Online) | Saturday, January 31st · 9:00 AM EST

Ready to make 2026 your smartest financial year yet? Join us for Wealth Summit 2026, where real estate, tax, and wealth-planning experts break down the proven blueprint for protecting and multiplying your wealth.

REGISTER HERE

Early-bird registration is now open — save 40% when you secure your spot early. Seats for the in-person experience are limited and always sell out fast.

Discover the frameworks, tax strategies, and legacy tools top performers use to stay ahead — no matter the market.

 

Top 10 FAQs About Selling Investment Properties in Ontario (2026 Edition) 

Q: How has the Ontario real estate market changed for investors going into 2026? 

A: Inventory in markets like Hamilton and Kitchener–Waterloo is up 50–60% compared to 2023, while prices are roughly 20–30% below the 2022 peak and range-bound, so investors face more competition when selling. 

Q: Is 2026 a good time to sell an investment property in Ontario? 

A: It can be, if you’ve owned for several years and price realistically against bank sales, estate sales, and higher inventory, but many investors are better off re-renting and waiting out the market if they don’t need to sell. 

Q: What’s the biggest mistake investors make when selling rental properties in Ontario? 

A: Hiring a non-investor realtor and ignoring tenant issues; when the property doesn’t sell, they pivot to Plan B with a poorly screened tenant and can end up in Landlord and Tenant Board nightmares. 

Q: Are student rentals still a good investment strategy for Canadian investors? 

A: University student rentals near major Ontario campuses remain one of the most resilient cash-flow strategies, thanks to strong enrollment and regular tenant turnover, whereas college-heavy markets reliant on international students have struggled. 

Q: How long does it take to find a good tenant in the 2026 Ontario rental market? 

A: In many areas it now takes 6–8 weeks or more to find a high-quality tenant for single-family homes, duplexes, and basement units, so investors should budget for at least two months of vacancy. 

Q: What are the best tenant screening tools for Ontario landlords? 

A: Many professional property managers use SingleKey for credit and application processing and OpenRoom to check for existing court orders, combined with manual checks of income, landlord references, and online searches. 

Q: How will Bill 60 impact landlords and selling investment properties? 

A: Bill 60 proposes shorter timelines for non-payment, potential changes to compensation when buyers move in, and rules requiring tenants to pay a portion of rent owed before raising maintenance complaints, which slightly improves the environment for responsible landlords. 

Q: Should I buy a vacant rental property or one with tenants in place? 

A: In today’s market, buying a property with a strong, paying tenant at near-market rent can be safer because buying vacant often means at least two months of vacancy and extra leasing risk. 

Q: What types of rental units are most in demand in Ontario right now? 

A: Larger, brighter units—especially above grade, with multiple parking spots and family-friendly layouts—are renting faster than small micro-condos or cramped basement apartments. 

Q: How can Canadian investors protect their cash flow until interest rates drop? 

A: Focus on tenant quality over speed, consider rent renegotiations with below-market tenants, and be willing to pivot from selling to re-renting if offers don’t match your long-term goals. 

📜 Full Transcript

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

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/0g5Jt74Qff54WifcfEU6FH?si=3554156498454d05

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/c50ae533-1e20-4bf2-80d9-82ddb8d70b7d/the-truth-about-real-estate-investing-for-canadians-how-to-sell-a-tenanted-property-in-2026-what-investors-need-to-know-now

Audible: https://www.audible.ca/pd/B0G53GJWGW?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/-G3MkQjEH4Y

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

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.