By Erwin Szeto | Co-Founder, iWIN Wealth Planning 

Recorded: June 2026 

Host: Erwin Szeto, The Truth About Financial Independence for Canadians 

Guests: Ming Lim, Managing Partner of Volition Properties and Co-Owner of AccounTrain; Bryan Ma, CPA, CFA, MBA, Co-Owner of AccounTrain 

Ontario real estate investing is in a different place than it was three years ago.

Rent control, slowed appreciation, rising costs, and a Landlord and Tenant Board backlog that can stretch eviction timelines past a year have changed the economics for active operators. The investors who used to add another door to their portfolio every 12 months are now asking a different question: if not more rentals, then what? 

In this episode of The Truth About Financial Independence for Canadians, Erwin sits down with Ming Lim and Bryan Ma, two friends who became business partners in January 2026 when they acquired AccounTrain, a 25-year-old bookkeeping firm based in Ottawa with clients across Canada. They beat out 5 other offers, paid 1.3 times annual revenue and they spent almost 2 years searching for the right deal. 

About Ming Lim and Bryan Ma

Ming is the managing partner of Volition Properties, where his team has helped Canadians transact on more than $300 million in Toronto investment real estate. Bryan spent 20 years in Canadian financial services as a CPA, CFA, and MBA, with most of his recent work in mergers and acquisitions at Intact Insurance. Their conversation is a real-world picture of what buying a small business from a retiring boomer actually looks like for Canadian investors who have already built equity in real estate. 

Why Active Real Estate Operators Are Looking at Small Business Acquisition 

Ming has been investing in Toronto real estate since 2015. He has seen the market shift from one where adding more doors was the obvious move to one where the math demands a harder look. His team at Volition Properties has remained active, but he has spent the last 2 years exploring what comes next. 

Bryan came at the question from a different angle. After 20 years in financial services, including roles at 3 of the largest professional services firms in Canada and most recently at Intact Insurance, he reached a moment of clarity that anyone in corporate finance will recognize. As he tells Erwin during the episode, he was doing 80-hour weeks on M&A files when he realized he had stopped enjoying the work. 

The two had known each other for years before deciding to partner up. The thesis they landed on is one that has been gaining traction quietly in Canadian operator circles for the last 5 years: the great wealth transfer. Baby boomers built thousands of small Canadian businesses over the last 40 years, many of them profitable, durable, and unsexy. They are now reaching retirement age without succession plans. The opportunity is enormous, but it is also harder than it looks. 

How They Found AccounTrain 

Ming and Bryan spent close to 2 years looking before they found the right business. They worked through several channels: a buy-side community called Village Wealth, business brokers including Poe Group (which specializes in accounting firms), and direct outreach to owners of businesses that fit their criteria. 

They tell Erwin the market is more competitive than most outside observers realize. Quality businesses with clean books and stable cash flow are often gone within 24 to 48 hours of listing. Buyers submit offers on businesses they have only partially reviewed, knowing they will lose the deal if they wait for full due diligence. Ming and Bryan estimate they looked at 1 to 2 businesses per day for almost a year before AccounTrain came up. 

AccounTrain itself was sourced through Poe Group. The firm had been in business for 25 years, founded and run by a single operator who was approaching retirement. Initial interest came from 15 to 18 parties. By the time the bid deadline closed, there were 5 serious offers. Ming and Bryan’s offer was selected, they believe, partly because of Bryan’s M&A background, which signalled to the seller that the buyers understood the process and would be reliable to close. 

Why Bookkeeping, Not a Full Accounting Practice 

One of the most useful threads in the conversation is the deliberate decision to buy a bookkeeping firm rather than a full accounting practice. Most investors looking at the professional services space assume the bigger prize is an accounting firm with CPAs on staff, tax preparation engagements, and audit work. 

Ming and Bryan went the other direction for a reason. Bookkeeping has fewer regulatory requirements. The owner does not need to be a CPA. The work is more systems-driven and less personality-driven, which means the business is less dependent on any single employee or partner. Pricing is more predictable. And the client relationship is recurring, which produces stable monthly revenue rather than the seasonal spikes accounting firms see around tax season. 

The tradeoff is that bookkeeping firms typically sell at lower multiples than accounting firms. But Ming and Bryan argue that the lower entry price and the simpler operating model more than offset the lower exit multiple, especially for buyers who plan to hold and modernize rather than flip. 

The Math of Buying a Bookkeeping Firm 

Bookkeeping firms in Canada generally trade in a range of 1.2 to 2.5 times annual revenue. Where a specific firm lands within that range depends on several factors: client concentration, recurring versus one-time revenue mix, geographic distribution, technology stack, owner involvement, and the quality of the books themselves. 

AccounTrain had approximately $1 million in annual revenue at the time of sale. Ming and Bryan paid 1.3 times revenue, putting the purchase price at approximately $1.3 million. They consider this on the low end of the range, in part because the firm was owner-operated with limited systems documentation, in part because the buyer pool was thinner than for a larger or more institutional firm. 

The deal structure included a vendor take-back component, which Ming and Bryan describe as standard in business sales but uncommon in Canadian residential real estate. They paid a portion of the purchase price at closing, with the seller financing the balance over a defined term. The vendor take-back also functioned as a structural commitment from the seller to remain available during the transition period, which became important given how much institutional knowledge needed to transfer. 

The Vendor Take-Back Mortgage as Industry Standard 

One of the most counterintuitive points in the episode is how common vendor take-back financing is in business sales compared to residential real estate. In real estate, vendor take-backs are seen as a creative financing tool used in soft markets or for difficult-to-finance properties. In small business sales, they are the default. 

The logic is simple. The seller knows the business better than the buyer ever will. A vendor take-back keeps the seller’s interests aligned with the buyer’s success during the critical transition period. If the business deteriorates after closing, the seller’s outstanding balance is at risk. That gives sellers an economic reason to stay engaged, answer questions, and help transfer relationships. 

For active real estate investors looking at business acquisition for the first time, this is a meaningful structural shift to absorb. The seller is not just exiting. They are partially financing your deal and remaining a stakeholder in the outcome. 

Twenty-Five Years of Knowledge in One Person’s Head 

The previous owner of AccounTrain ran the firm for 25 years. By Ming and Bryan’s account, much of what made the business work was stored not in systems but in her memory. Client preferences, filing deadlines specific to non-profit clients, informal arrangements with longstanding customers, the rhythm of the work itself, all of it lived in one person’s head. 

This is a recurring pattern in boomer-built businesses. The founder is the system. The business runs because the founder remembers everything. When the founder leaves, the institutional knowledge leaves with her unless the buyer captures it in time. 

Ming and Bryan structured the transition period specifically to extract this knowledge. The previous owner is staying on in a transition role for an extended period, working with Ming and Bryan to document client relationships, encode informal processes into formal workflows, and modernize the technology stack. They are building the CRM and workflow management systems the firm never had. By the time the transition is complete, the business will run on systems rather than on memory. 

The Lifestyle Case for a Business Over a Rental Portfolio 

Ming and Bryan are both still active in real estate. Ming continues to run Volition Properties. But they make a specific lifestyle case for the business over more rentals. 

A bookkeeping firm with stable monthly revenue and a small employee base does not call you at 11 p.m. when a pipe bursts. It does not require an LTB filing when a tenant stops paying rent. It does not get hit with a sudden 4-figure repair bill the same month a vacancy opens up. The variance is lower. The hours are more predictable. The work scales through systems and additional staff rather than through Erwin’s 7-day-a-week attention. 

The episode is honest about the tradeoffs. A small business has its own demands, especially during the first 6 to 12 months after acquisition when the new owners are still learning the operation. But for an active real estate investor whose portfolio is consuming evenings and weekends, a bookkeeping firm is often a calmer use of operator energy. 

How to Connect with Ming Lim and Bryan Ma 

To follow Ming and Bryan, visit accountrain.com or connect with them on LinkedIn. Ming’s real estate brokerage is Volition Properties: https://www.volitionprop.com/ 

Quick Answers 

Who are Ming Lim and Bryan Ma? 

Ming Lim is the managing partner of Volition Properties, a Toronto-area real estate brokerage. Bryan Ma is a CPA, CFA, and MBA with 20 years in Canadian financial services. In January 2026 they jointly acquired AccounTrain, a 25-year-old Canadian bookkeeping firm. 

What is AccounTrain? 

AccounTrain is a bookkeeping firm based in Ottawa with clients across Canada. The firm was founded over 25 years ago and was acquired by Ming Lim and Bryan Ma in January 2026. 

How much does a bookkeeping firm cost to buy in Canada? 

Canadian bookkeeping firms typically trade at 1.2 to 2.5 times annual revenue, depending on factors like client concentration, recurring revenue, geography, and the quality of the books. Ming and Bryan paid 1.3 times revenue for AccounTrain, which they describe as the low end of the range. 

What is a vendor take-back mortgage in a business sale? 

A vendor take-back mortgage in a business sale is seller financing for a portion of the purchase price. The buyer pays a portion at closing, and the seller carries the balance as a loan over a defined term. Vendor take-backs are standard in Canadian small business sales because they keep the seller’s interests aligned with the buyer’s success during the transition period. 

Where can you find Canadian small businesses for sale? 

Buyers can source Canadian small businesses through business brokers (such as Poe Group, which specializes in accounting firms), buy-side communities (such as Village Wealth), direct outreach to retiring owners, and industry-specific listing services. The market is competitive, and quality deals can close within 24 to 48 hours of listing. 

Why are some Canadian real estate investors moving to small business acquisition? 

Several forces are pushing active Canadian real estate investors toward small business acquisition: rent control and LTB backlogs have made residential rentals harder to operate, retiring baby boomers are creating a large supply of profitable small businesses for sale, and the lifestyle profile of a small business is often more sustainable than managing a portfolio of rental properties. 

The Bottom Line 

Canadian real estate is not dead. But for active operators, the math that worked in 2018 doesn’t work the same way in 2026. The hours required to manage rentals through rent control and LTB delays have crowded out the time real estate investing was supposed to give back. 

Ming and Bryan are part of a small but growing group of Canadian operators who are pointing at small business acquisition as the answer. Their experience is worth listening to because they are not selling you on it. They tell you exactly what it cost them in time, in cash, and in operator attention. Two years of searching. $1.3 million in capital. A vendor take-back commitment. A multi-month transition period extracting institutional knowledge from a 25-year operator’s memory. 

If you are sitting on Ontario rentals and have started asking yourself what the next 10 years of operator energy should be spent on, this conversation is a real-world picture of one alternative. It is not the only path. But it is one worth understanding before you decide what your next move is. 

Join Me Live: Free Training on the $100,000 Investment Loan Strategy

I’m hosting a free training on the strategy that produced the returns I mentioned above. It’s hybrid: in-person at the iWIN office in Oakville, or join on Zoom from anywhere.

Here is exactly what I will walk through in 90 minutes:

1. The complete $100,000 investment loan structure
2. The math — what $433 a month actually buys you over 5 and 10 years
3. Every loss scenario — what happens when the market drops 20%, 30%, 40%
4. How this fits alongside, not replacing, a real estate portfolio
5. Live Q&A — bring your questions, bring your skepticism

Two dates to choose from. Both cover the same content — pick whichever fits your schedule.

Saturday June 27, Hybrid (Oakville + Zoom) — 9:00am ET, hard stop 10:30am. In-person seats are capped at 40 and they always go. If you want to be in the room, register today.

Tuesday July 7, Zoom only — 8:00pm ET

To Listen:

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/Buying-a-25-Year-Old-Bookkeeping-Firm–Ming-Lim–Bryan-Ma-e3kbo9a 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/71792264-c2b6-474d-b540-762219a96aee/the-truth-about-financial-independence-for-canadians-buying-a-25-year-old-bookkeeping-firm-ming-lim-bryan-ma

Apple: https://podcasts.apple.com/ca/podcast/buying-a-25-year-old-bookkeeping-firm-ming-lim-bryan-ma/id1100488294?i=100077131575

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 

Disclaimer: 

As a committed advocate for transparent and responsible investing, I 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. I am also a licensed insurance agent with Open Concept Financial Group. The investment loan strategies discussed are for educational purposes only and are not a guarantee of approval or performance. Past performance is not indicative of future results. Every investor should do their own due diligence. 

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.

By Erwin Szeto | Co-Founder, iWIN Wealth Planning 

Recorded: May 2026

Host: Erwin Szeto, Truth About Financial Independence for Canadians

Guest: Greg Kowalczyk, former design engineer turned full-time entrepreneur.

If you’d told me a year ago that a guy I’ve known for over a decade, an engineer with almost no coding background, would build two fully functional iPhone apps for the price of a nice dinner for four, I’d have nodded politely and changed the subject. This week’s guest on The Truth About Financial Independence for Canadians is Greg Kowalczyk. Greg’s a former design engineer who became an Ontario landlord, then an Amazon brand builder, and over the last twelve months has quietly become one of the most practical AI users I know.

The numbers he’s putting up aren’t theoretical. They’re real, they’re his, and they should change how you think about what’s possible in your own business and your own portfolio. 

The $800 question 

Greg built two apps that are live on the Apple App Store today. RunMate Pro tracks runs and the mileage on your running shoes. The other is a sun-protection index app for his e-commerce brand Gear Top, which tells you how long it’s safe to be outside. 

Built the old way, with a developer? Greg’s estimate: fifty to seventy thousand dollars. Months of meetings. Revisions. Scope creep. 

Built the new way, with Greg talking to AI while walking his dog? About eight hundred dollars in tokens. A few months of his time, mostly evenings and weekends, while still running his businesses. 

“If you paid developers, you’d probably spend $50,000 to $70,000 just to design those two apps. I calculated what it actually cost me, without my time, at about $800.” 

That isn’t a one-off. It’s a pattern that runs through everything Greg’s been doing. 

Replacing a $5,000 photo shoot 

Greg’s e-commerce brand Gear Top sells sun-protection apparel. Hats, gloves, balaclavas. His original product, a balaclava launched in 2014, still has nearly 7,000 reviews on Amazon. Another hat in the lineup has over 26,000 reviews. To get the product photography for these listings, Greg used to do what every serious Amazon seller does. Rent a studio downtown. Book a photographer. Hire models, sometimes four or five of them at once, including kids. Shoot all day. The going rate? Three to five thousand dollars per session. Plus the photographer’s processing fees. Plus, the time to organize everyone in one place for the twelve hours of shooting. 

Today, Greg generates almost all of his product imagery with AI. He uses Gemini’s Nano Banana model for stills and Veo for video. He’ll create a character once, then have the AI reproduce that same character across multiple scenes for a cohesive look. For a recent product launch on a new line of nasal strips, his cousin in Poland used the same approach to produce a thirty-five second animated commercial. Five clips of about eight seconds each, stitched together. 

The packaging design for the kids’ version of those nasal strips? Designed with AI. The mascot characters in the videos? AI-generated. The fifteen-second hero clip you’d have paid an agency four or five figures for? Generated overnight. 

“We used to pay $3,000 to $5,000 a session for a photographer and models. Now I just talk to AI and get what I want.” 

For an Amazon seller, that’s not a productivity gain. That’s a margin expansion. 

A website built while you sleep 

Greg owns the domain gregkowalczyk.com. He registered it back in 2013. For over a decade, the site sat dormant because building a personal site felt like too much work. Hire a developer, pay them, manage them, get something he didn’t really love, repeat.

One weekend last year, he decided to try something different. He wrote a script telling the AI what he wanted. A personal site with all his projects, all his links, all his work. Then he let it run in a loop, what’s called a “Ralph loop,” overnight. He woke up the next morning to a finished website. 

He uses the same approach for the Bronte Harbour Classic, the inaugural 5k race he’s putting on in Oakville this year. The website, the sponsor pages, the registration integrations, all of it built by Greg with AI assistance. When I asked him last week to add a clearer age-range explanation to the kids’ race, he made the change from his desk in about ten minutes. The AI updated multiple pages and even created a new one to host additional details. It also logged into the third-party registration platform and made the matching changes there. 

A web developer would have taken a week to do that work and probably missed a spot or two. 

Dashboards instead of software subscriptions 

Here’s the part that should make your ears perk up if you own any SaaS stocks. 
Greg used to pay for QuickBooks’ mileage-logging module. He found it overcomplicated, frustrating, and a bad fit for how he actually wanted to log mileage. So he built his own. Voice-driven, simple, designed around his workflow. He’s already cancelled QuickBooks’ module. 

He used to pay for analytics dashboards for his e-commerce businesses. Now he builds his own dashboards. He gets direct access to the underlying data source, pulls the metrics he cares about, and lays them out exactly the way he wants to see them.

“I don’t have to build software anymore. I build dashboards. I just get direct access to the software I need the numbers from, pull out the analytics, and put them the way I want to see them. Once I build it, that’s my software.” 

This is a small business owner replacing line items on his monthly P&L with custom-built tools that fit his business better than the off-the-shelf product ever did. Multiply that across millions of small businesses and you start to understand why some software companies are watching their stock prices come down hard from the peak. A lot of my friends I trust think we’re nowhere near the bottom for legacy SaaS. 

The Ontario landlord chapter 

The real estate sub-thread on this episode is just as interesting, and just as practical. Greg’s been an Ontario landlord since 2012. His first property was an RTO deal in Cambridge that I covered the home inspection on, before I really knew him. He’s owned student rentals in Hamilton and Kitchener, single-family rentals in St. Catharines, and converted two properties into legal duplexes in 2022 and 2023. 

Why convert? Cash flow. When his mortgage renewals hit just after COVID, the math on a property charging $1,800 in rent stopped working. So instead of selling, he refinanced two properties and used the equity to build two basement suites. The Hamilton conversion cost about $220,000 because it was a full gut job, complete with the famous (now) discovery of a backyard marijuana plantation he had to chop down and put out with the lawn waste. 
He’s still holding the portfolio. But he’s also realistic about the experience. 

“Nothing can challenge me anymore. We had eviction, we had flooding, we had fire. Flooded toilet? That’s just Tuesday.” 

If you’ve been a Canadian landlord through the last few years, that line lands a little too hard. 
His current AI-related side project in the real estate space? Auto-populating LTB forms. Anyone who’s filled out a Landlord and Tenant Board application by hand knows exactly how big a win this would be. 

What Greg told the listener who hasn’t started 

I asked Greg my standard close-of-show question. If somebody listening hasn’t done anything with AI yet, where should they start? 
His answer was characteristically practical. Three steps. 

• Step one: install one of the tools. ChatGPT, Claude, Gemini, doesn’t really matter. The regular chat is fine. 
• Step two: go deeper than chat. Use the research modes. If there’s a topic you’ve been curious about, ask the AI to do a deep research run on it. Read the result. 
• Step three: turn the research into a deliverable. A summary. A slide deck. A one-page PDF. A landing page. The point isn’t the deliverable itself. The point is that by going from raw output to finished asset, you discover the real range of what these tools can do. 

“You have almost the smartest agent in the world in your pocket. He’s like a PhD professor, available 24/7. Just ask him whatever you like.” 

That’s the soundbite I want every podcast listener to walk away with. Not “AI is the future” in the abstract. Just: there’s a tool in your pocket that knows almost everything, and most people are barely using it. 

Where this fits into the bigger picture 

The TAFI thesis is that there’s more than one path out of the rat race. Real estate is one. Building or buying a business is another. The stock market is another. Investment loans are another. AI is now one of the most powerful tools you can lay across any of those paths to accelerate the math. 

Greg’s the proof. He didn’t pick AI as a new asset class. He picked it as a tool to make every asset class he already plays in cheaper and faster to operate. His e-commerce business runs at a fraction of its previous photo and video budget. and his race event runs with a one-person marketing team. His real estate portfolio is about to have an LTB form filler that none of his competitors will have built for themselves. 

If you’re an Ontario investor who’s tired of the landlord life and looking for what’s next, here’s a model: keep what’s still working, get creative on the rest, and use AI to compound everything you build from here. And if part of “what’s next” for you is growing wealth beyond the rentals without buying another property, that’s exactly what I cover in my next free training. 

Join the next free training 

This Saturday — May 30, 2026 — I’m hosting a free training called the Zero-Down Wealth Strategy. It’s hybrid: in-person at the iWIN office in Oakville, or join on Zoom from anywhere. Hard start at 9:00am Eastern, hard stop at 10:30am. 

In those 90 minutes, I’m walking through: 

1. The complete $100,000 investment loan structure 

2. The math — what $433/month actually buys you over 5 and 10 years 

3. Every loss scenario — what happens when the market drops 20%, 30%, 40% 

4. How this fits alongside (not replacing) a real estate portfolio 

5. Live Q&A — bring questions, bring skepticism 

In-person seats are capped at 40 people and they always go. If you want to be in the room, register today. 

Saturday May 30 — Hybrid (Oakville + Zoom): infinitywealth.ca/20260530 

Tuesday June 2 — Zoom only at 8pm Eastern: infinitywealth.ca/2026060

Both events cover the same content. Pick whichever fits your schedule. 

To Listen:

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/He-Talks-to-AI-While-Walking-the-Dog–Grek-Kowalczyk-e3josig

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/a320b735-bb19-499b-81e3-945d396adacc/the-truth-about-financial-independence-for-canadians-he-talks-to-ai-while-walking-the-dog-grek-kowalczyk

Audible: https://www.audible.ca/pd/B0H2W56826?source_code=ASSGB149080119000H&share_location=pdp 

Apple: https://podcasts.apple.com/ca/podcast/he-talks-to-ai-while-walking-the-dog-grek-kowalczyk/id1100488294?i=1000769484484

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.

By Erwin Szeto | Co-Founder, iWIN Wealth Planning 

Recorded: May 2026

Host: Erwin Szeto, Truth About Financial Independence for Canadians

If you’ve been around me for the last couple of years, you’ve heard me talking about diversification. Specifically, diversifying out of Canadian real estate concentration. I’ve been making this case publicly since I met SHARE in 2023. The math in Ontario stopped working for the average passive investor a while ago, and I’ve been saying so. 

So this article isn’t another version of that case. You’ve heard it. I’ve made it. Cherry and I have been quietly walking the talk — slowly unwinding our Hamilton rentals as tenants naturally turn over, redeploying that capital methodically. None of that is news. 

What I want to spend this article on is the *what next* — the specific places that capital is going, and especially the one strategy I haven’t talked about much publicly until now. 

Three threads, briefly: U.S. landlord-friendly real estate (we’ve covered that on the show since 2022). Business acquisition — including the one Cherry quietly pulled off two years ago, which has been a game-changer for our family. And then the third piece, which is where this article wants to spend most of its time: real-estate-style leverage applied to the stock market. Twenty-five percent down. The other 75% borrowed through an institutional investment loan. Same structural math we’ve used in real estate for thirty years — applied to the index instead of a duplex. 

If you’ve been quietly wondering whether there’s a way to put your money to work that isn’t another mutual fund and isn’t another Ontario rental — keep reading. This is for you. 

Quick Context: Why I’ve Been Saying What I’ve Been Saying 

Brief recap, for anyone newer to my work. 

I’m not saying real estate is dead in Canada. I’m saying the conditions that made it easy for the average passive investor are gone. Population growth has slowed. Cap rates are compressed. Capital requirements have ballooned. Rent control plus anti-renoviction bylaws plus inflation have squeezed the math to the point where professional property management costs more than the math supports. The infrastructure that made passive Canadian real estate actually passive — particularly the affordable third-party manager — is disappearing. 

That’s the death of passive — not in theory, in practice. The infrastructure that made passive Canadian real estate investing actually passive isn’t there anymore. 

Active operators are still making it work. People running real estate as a real business — teams, systems, scale, the discipline to handle the LTB. They’ve earned it. I cheer for them. I send them clients. They will be guests on my show. 

But for the client who wanted passive — who wanted cash flow without the second job — that option here in Canada has largely closed. So I’ve been pointing them somewhere else. 

Where Passive Real Estate Investing Went: South 

Passive real estate investing for Canadians didn’t disappear. It moved south. 

Landlord-friendly U.S. markets — places where tenant laws aren’t stacked against owners, cap rates pencil, and you can hire institutional-grade property management that handles everything — are where the math now lives. We’ve covered this on the show since 2022, partnered with SHARE in 2023, and it’s been the through-line of the diversification message I’ve been making publicly for two and a half years. 

Quick example, in case you’re new. A client of ours just closed on a single-family home in South Carolina. Two-hundred-and-thirty-five thousand U.S. dollars. House built in 1996. Almost 2,400 square feet. Twenty-two-minute drive from the BMW plant that employs 11,000 people. Cap rate? 7.3 percent. Closing? 30 to 60 days. 

Try finding that combination in Ontario today. The math doesn’t exist here anymore. 

That’s leg one of where Cherry and I are redeploying capital from the Hamilton sell-down. If that’s the part you came for — that’s the part. Now let’s talk about the other things diversification looks like in our actual household, before we get to the strategy this article wants to spend its time on. 

ICYMI: We Bought a Business Two Years Ago. It Changed Everything. 

Two years ago, Cherry acquired another accounting firm. The previous owners? Two retiring boomers ready to step away from their practice. At the time it was a meaningful capital deployment and a meaningful operational bet. With the benefit of hindsight, it was perfectly timed. 

A boring, cash-flowing professional services business — landed right as the Canadian real estate market was decelerating. It became the counterweight to the slowdown. As real estate transaction volume softened across our realtor business at iWIN Real Estate, Cherry’s accounting practice was doing the opposite — quietly compounding, generating recurring cash flow, completely uncorrelated with the housing market. 

And here’s the bigger point. Cherry didn’t just acquire a business. She executed the textbook version of what’s about to be the largest small business ownership transfer in Canadian history. Two retiring boomers, no internal succession, a profitable practice that needed a new owner. Cherry stepped in. Buyer wins, sellers win. That exact transaction is going to happen tens of thousands of times across this country over the next decade — and most retail investors aren’t even thinking about it as an investment category. 

That’s diversification working the way it’s supposed to. 

A boring, cash-flowing business to offset the slowdown of the real estate market. That’s diversification working the way it’s supposed to. 

And we’re not alone.

If you’ve been listening to the show, you’ve heard me say this — more and more real estate investors are pivoting into adjacent services. Becoming realtors, mortgage agents, general contractors and accountants. My paralegal friend Andrew switched into HVAC. The pattern is everywhere once you start looking for it: people who built wealth in real estate are moving toward businesses that own the cash flow rather than the property. 

Some have tried hospitality — short-term rentals, AirBnB — and got squeezed when municipalities started shutting it down. The boutique operators with proper licensing and unique product are still doing well, but it’s no longer the easy retail-investor play it was five years ago. 

The bigger trend behind all of this — the one most retail investors are sleeping on — is exactly what Cherry just did. Boomer business owners are retiring. Many have no transition plan. No kid taking over the shop. No succession. Which means the next generation has an enormous opportunity to acquire profitable, cash-flowing businesses at fair, sometimes generous, prices. And there’s a lifetime capital gains exemption in Canada that makes selling a qualifying business incredibly tax-efficient — meaning sellers are often willing to negotiate creatively. Buyer wins, seller wins. 

Boring HVAC company. Landscaping route. Dental practice. Accounting firm. The cash-on-cash returns on these things, when you bought them right, are not in the same league as a duplex in Hamilton. And nobody’s bidding the prices up the way they do on real estate, because most people don’t know how to value or finance a small business. 

Cherry and I are living proof of the strategy. It’s one of the pillars the new show is going to spend serious time on. 

Now the Piece I Haven’t Talked About Much: 25% Down on the Stock Market 

Here’s the part of my personal playbook I haven’t talked about publicly nearly as much as the U.S. real estate or business acquisition pieces — and it’s the one I think is the bigger missing puzzle piece for most of the investors in my audience. 

Almost no Canadian retail investor knows this option exists, but you can take real-estate-style leverage and apply it to the stock market. Here’s the structure: a creditworthy Canadian can access a $100,000 investment loan with no money down. Monthly cost of carry is roughly $433 per month. The investment vehicle has principal protection built in. The interest may be tax-deductible. And if you have a spouse with good credit, you can stack a second $100,000 the same way. 

In real estate terms, this is a 25% down deal — except there’s no down payment. It’s leverage applied to the broad index, not to a duplex. 

If that sounds aggressive, stay with me — because it’s actually the same expected-return math you’ve been doing on Ontario rentals for years. You just haven’t seen it applied this way. 

The 2005 framework, applied to 2026 

Back in 2005, when I was running my expected-return math on a real estate investment, the standard assumption was 20% down, 80% mortgage, and roughly 3% appreciation per year. Run that math through, factor in the leverage, and your expected return on the cash you actually put in lands around 15% per year. That’s the math that built the Canadian real estate investing industry. The leverage did the work. 

Now apply the same framework to the stock market. Twenty-five percent down. Borrow the other 75% through an investment loan. Assume the stock market’s long-run historic average — call it around 10% per year. Run the math the same way. Factor in your cost of carry on the borrowed portion. Expected ROI on your equity? Around 40%. 

Now, before anyone yells at me — yes, the past does not predict the future. Yes, leverage cuts both ways. Yes, 10% is an assumption, not a guarantee. We will walk through every loss scenario at the live training. 

Even if the stock market only does 6% — way below average — I still get a respectable return on my equity. And I get zero landlord headaches. 

That’s the trade. Just a deposit, a wire transfer, and quarterly statements. For the lazy investor — the one protective of their time and mental health — it’s the easiest yes I’ve ever signed. 

Why this fits the audience I serve 

Most of my clients are over-concentrated in Canadian real estate. They wanted passive. They got an active job they didn’t ask for. They’ve been looking for a way to diversify without dumping properties at the bottom of the cycle. 

This strategy was built for that exact person. It’s the second leg of what Cherry and I are doing personally — pulling capital from Ontario as it naturally frees up, and putting some of it into a leveraged equity position that gives us index exposure with the same kind of leverage real estate already taught us to use. 

It’s not magic. It’s not a shortcut. It’s just the same math you already understand, applied to a different asset class. 

Important Context: This Isn’t My Whole Portfolio 

Before anyone takes the wrong message from this article, let me be clear about something. 

This isn’t my whole portfolio. Not even close. Cherry and I still hold significant Canadian real estate. We have active businesses generating cash flow. We carry insurance and we have a properly diversified picture across asset classes, income sources, and time horizons. The leveraged stock market position I’m describing is one leg of that. Not the whole table. 

And I’m not telling you to put your last dollar into this either. I’m telling you it deserves a seat at the table — alongside whatever else you’re already doing. Diversification is the whole point. Don’t put all your eggs in this basket. Or any basket. 

A Quick Note on the Show — and Why This Is Actually Going Back to Roots 

If you’ve been listening to my podcast for any length of time, you know it as The Truth About Real Estate Investing for Canadians. Almost five hundred episodes over nearly a decade. 

Starting now, the show is becoming The Truth About Financial Independence for Canadians. TAFI for short. Find it at tafipod.ca. 

Here’s the thing about this rebrand that I want you to understand. It might look like a departure. It’s actually the opposite. It’s a return to the original idea that started me down this path twenty years ago. 

In 2005 I read Rich Dad Poor Dad. Like a lot of you. The whole point of that book — the whole reason it changed how millions of people think about money — was that there is no single path out of the rat race. Real estate is one path. Owning a business is another. Investing in paper assets is another. Kiyosaki was clear about it. Most of us who started with real estate just got so good at it that we forgot the rest of the framework existed. 

Like all entrepreneurs, we have to pivot. This change is the show going back to its roots — exiting the rat race the way Kiyosaki actually wrote about. Multiple paths. Not just real estate. 

So the rebrand isn’t the show changing direction. It’s the show finally living up to what it was always supposed to be about. Career and income optimization. U.S. real estate. Leveraged stock-market investing. Buying small businesses from retiring boomers. Lifestyle design. Canadian tax strategy. AI as a wealth-creation tool. Multiple paths. Same Rich Dad philosophy. 

Like all entrepreneurs, we pivot. This is ours. 

Want the Whole $100,000 Strategy Walked Through Live? 

This Saturday — May 30, 2026 — I’m hosting a free training called the Zero-Down Wealth Strategy. It’s hybrid: in-person at the iWIN office in Oakville, or join on Zoom from anywhere. Hard start at 9:00am Eastern, hard stop at 10:30am. 

In those 90 minutes, I’m walking through: 

1. The complete $100,000 investment loan structure 

2. The math — what $433/month actually buys you over 5 and 10 years 

3. Every loss scenario — what happens when the market drops 20%, 30%, 40% 

4. How this fits alongside (not replacing) a real estate portfolio 

5. Live Q&A — bring questions, bring skepticism 

In-person seats are capped at 40 people and they always go. If you want to be in the room, register today. 

Saturday May 30 — Hybrid (Oakville + Zoom): infinitywealth.ca/20260530 

Tuesday June 2 — Zoom only at 8pm Eastern: infinitywealth.ca/2026060

Both events cover the same content. Pick whichever fits your schedule. 

The Bottom Line 

Canadian real estate isn’t dead. But the conditions that made it a passive vehicle for the average investor are gone. If you want to be an active operator and treat real estate as a business, more power to you. If you want passive, you have to look elsewhere — landlord-friendly U.S. markets, leveraged stock-market positions, small-business acquisition, and a few other paths the show will keep covering. 

Diversify. Pacify. Get your time and your peace of mind back. 

That’s the next chapter.

To Listen:

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/Welcome-to-the-Truth-About-Financial-Independence-e3j379d 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/46779809-e913-42b2-8984-b5e0dc7f30d5/the-truth-about-real-estate-investing-for-canadians-welcome-to-the-truth-about-financial-independence

Audible: https://www.audible.ca/podcast/ITEM-NAME/B0GYKNM4JR?source_code=ASSGB149080119000H&share_location=pdp

Apple: https://podcasts.apple.com/ca/podcast/welcome-to-the-truth-about-financial-independence/id1100488294?i=1000766797099

YouTube: https://youtu.be/ibBWxozAre8

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.

By Erwin Szeto | Host of The Truth About Real Estate Investing for Canadians 

Recorded: April 2026

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

Three Real Estate Stories the Headlines Are Missing in 2026 

Three stories crossed my desk in the last few weeks that every Canadian real estate investor needs to hear about — together, not separately. Because when you put them side by side, they tell one story, and it’s the story the headlines are missing. 

Story one: Ontario’s HST rebate on new-build homes launched April 1st, and sales surged at major builders. Story two: Alberta’s new-build market — the province everyone has been telling you to buy into — is showing real cracks. And story three: a regulatory ruling from FSRA that hit close to home for me personally, and that carries a lesson every private investor needs to absorb. 

Here’s what they have in common. The headline is never the whole story. The loudest voices in a market are rarely the most informed. And your job as an investor is to do your own work. 

Let’s get into it. 

Story 1: Ontario’s HST Rebate Sparks a Sales Surge — But the Investor Window Has Already Closed 

On April 12th, the Globe and Mail reported that new-build home sales in Ontario surged in the first week of the province’s new HST rebate. Major homebuilder Minto sold nearly 120 new homes in Ottawa and the Toronto region. Branthaven Homes sold more homes in one week than they did in all of 2025. The industry trade group BILD called it a “jolt.” 

If you’re an Ontario landlord or investor, the question is obvious: is this the bottom? Is preconstruction back? Should I jump in? 

Before you do, you need to understand what the rebate actually covers — and what it doesn’t. 

How the Ontario HST New-Build Rebate Works 

Effective April 1st, 2026, Ontario buyers can claim a rebate on the 13% HST on new-build homes. The transaction window runs until March 31st, 2027. The rules differ depending on whether you’re buying to live in the home or to rent it out. 

For end-users (people buying a home to live in), construction has to start before December 31st, 2028 to qualify. That’s a meaningful window. 

For investors (people buying to rent the unit out), the rules are dramatically tighter. Construction must already have been started by March 31st, 2026 — a date that has already passed. In other words, the investor version of this rebate only applies to product that’s already in the ground. There is no path for an investor to buy a brand-new project and qualify. 

It’s also worth noting that the rebate is not yet ratified in legislation. Buyers and developers are transacting as if it is, but the federal Department of Finance told the Globe it cannot speculate on timelines. 

The Case for Optimism 

Let’s give the rebate its fair due. Thirteen per cent off a new home is real money. On a $700,000 townhome, that’s $91,000 — a meaningful down payment, not a marketing gimmick. 

The volume is undeniable. Branthaven sold 120 townhomes in Milton and Mississauga and another 20 condos in Oakville in a single week. Construction jobs are coming back — Branthaven’s president told the Globe he expects to rehire up to 30 staff and put dozens of subcontractors back to work. And it begins to clear out the more than 10,700 cancelled GTA and Hamilton condo units that have hung over the market since 2022. 

The Case for Caution 

Not every builder is sharing in the surge. Fernbrook Homes — a 45-year veteran developer — told the Globe they had “many calls and inquiries” but the result was “no sales. Zero.” CEO Joe Salvatore said buyers are “100,000 per cent gun shy” after years of economic upheaval and the U.S. trade war. 

Minto’s own CEO openly questioned whether the surge would last: “Is this a short spurt that will peter out, or will it be sustained?” Pauline Lierman of Zonda Urban — a leading preconstruction researcher — was even more direct: “Demand and confidence is not all there.” 

And the underlying affordability problem hasn’t moved. Solmar Development just cancelled its large Bristol Place condo project in Brampton and converted it to rentals. Their executive vice-president told the Globe the issue was simple: buyers can’t qualify for mortgages and can’t come up with the down payments. “Affordability continues to be an issue, regardless of the rebates.” 

What This Means for Investors 

If you’re a first-time buyer or end-user, the rebate is genuinely worth a serious look. The math on your primary residence is different than the math on a rental, and you have a meaningful window to act. 

If you’re an investor hoping the rebate unlocks Ontario rentals, slow down. The investor cutoff has already passed. Anything you buy now does not qualify for the investor rebate. And Ontario’s underlying landlord economics — rent control, tenant board wait times, eviction process, capped annual increases — have not changed. A one-time purchase discount does not fix ongoing negative cash flow. 

If you’re an existing Ontario landlord whose properties are not cash-flowing, this rebate may actually create a window for you to exit. If new-build sales pick up broadly, the resale market tends to follow with a lag. That could be your opportunity to redeploy capital into something that actually cash-flows. 

Which leads us to where many Ontario investors have been looking for the past few years. 

🎧 Listen to the full podcast

Story 2: Why Toronto Investors Are Walking Away from Their Calgary Preconstruction Deals 

For the last three or four years, the loudest advice in Canadian real estate investing circles has been some version of: “Sell your Ontario rental, buy in Alberta.” I get it. Landlord-friendly legislation, no rent control, lower provincial taxes, a growing population, better affordability than the GTA or the Lower Mainland. On paper, it’s everything Ontario isn’t. 

Then on April 2nd, the Globe and Mail published a piece titled “Glut of new build homes starts to unhinge the Alberta market.” Every Canadian investor with Alberta exposure — or who is considering it — needs to read it carefully. 

The Calgary Townhouse Glut, By the Numbers 

According to Altus Group data cited in the Globe, unsold new-build townhome inventory in Calgary hovered below 1,000 units from mid-2023 through early 2025. By the end of 2025, it climbed past 1,030 — and rising. The share of new-build townhomes priced at or above $500,000 jumped from 40 per cent to 72 per cent in the same period, putting them out of reach of many local first-time buyers. 

Here’s the line every investor needs to absorb. Edward Jegg, Altus’s research manager of data solutions, told the Globe: “Many projects started in the early 2020s were targeted to Toronto investors,” and “a number of those sales to out-of-town investors are not going through, so they are coming back to the market.” 

Translation: the Toronto investors who bought Calgary preconstruction in 2021, 2022, and 2023 — when everyone was telling you Alberta was the next big thing — those deals aren’t closing. Investors are walking away or can’t qualify, and the inventory is landing back on the market and piling up. 

The Cash-Flow Story Has Changed 

Calgary agent Michael Ferianec of Urban Upgrade & New Infills explained why investor demand has dried up: “The cash flow that once made new-build townhomes an attractive investment has dwindled, as a healthy supply of purpose-built rentals, combined with slower population growth, drives down asking rents.” He’s also seeing “more flip-over from rental to sale. Because the rental market already has a lot of listings.” 

That’s a feedback loop. When rents soften, landlords list for sale instead of rent. That adds to for-sale inventory. That softens prices. Meanwhile, Calgary’s unemployment is still elevated, and oil prices are squeezing local cost of living. Three buyer segments — local first-timers, local renters, out-of-town investors — are all soft at the same time. 

The Long-Term Alberta Case Is Still Real 

I want to be fair here. The structural case for Alberta is still intact. Landlord-friendly legislation remains among the most landlord-friendly in the country. There is still no rent control. The eviction process is faster and more predictable than Ontario’s tenant board. Provincial tax burden is lower. Long-term population trajectory — interprovincial migration, international immigration — remains a tailwind, even if it has slowed. 

This isn’t a story about Alberta being broken. It’s a story about cycles. Calgary in 2026 looks different from Calgary in 2022. The investors who made money on Alberta over the last few years didn’t do it because Alberta is magic — they did it because they bought at the right part of the cycle, at the right price point, in the right sub-market, with the right financing. 

The Bigger Lesson — Stop Chasing Narratives 

The narrative that moves through Canadian investor circles is always one or two steps behind the data. In 2020 and 2021 it was “Toronto condos forever.” From 2022 through 2024 it was “get out of Ontario, buy Alberta.” And a lot of investors bought Calgary townhomes from a floor plan, sight unseen, in a sub-market they had never visited, based on a spreadsheet a promoter handed them at a free seminar. Now those units are completing, the rents aren’t where the pro-forma said they would be, the values aren’t where the pro-forma said they would be, and the investors are either walking or holding something that doesn’t cash-flow. 

This isn’t an Alberta problem. It’s a chasing-the-narrative problem. I’ve watched the same pattern in Toronto, Hamilton, Barrie — and now Calgary. 

Where the Real Opportunity Is Right Now 

Many of my recent podcast guests — active investors, builders, experienced operators — have told me the same thing. Deals are hard to come by right now. Construction costs are inflated. Property values, even in softer markets, haven’t collapsed the way some expected. The spread between what it costs to build and what you can sell or rent for has narrowed. That’s a tough environment to find a great deal in. The consistent message from those guests has been: be patient, underwrite quality, and don’t force a deal just to be in the market. 

With that context, here’s the opportunity I’d actually be paying attention to. A glut of unsold new-build inventory and small developers under real pressure — softening rents, oversupply, carrying costs, nervous lenders — is motivated-seller territory. 

Think about it. Why take on financing risk, development risk, construction risk, timing risk, and pay today’s inflated build costs — when there’s a small developer who has already carried all of that risk, has a finished building, and needs to move it? You can potentially buy turnkey, at a discount, with actual rent history and actual expense data. No pro-forma guessing. That’s a fundamentally better risk-adjusted position than buying preconstruction from a floor plan. The patient buyer with cash or pre-approved financing is the one who gets paid in this cycle. 

Story 3: FSRA’s $600,000 Penalty Against Claire Drage — and Three Lessons Every Investor Must Absorb 

The third story is the hardest one for me to write. Because it isn’t about a market or a policy — it’s about a person, and many in the Ontario real estate investing community knew her, including me. 

What FSRA Found 

On March 11th, 2026, the Financial Services Regulatory Authority of Ontario (FSRA) announced six administrative monetary penalties totalling $600,000 against Claire Drage, formerly a licensed mortgage broker in Guelph. The full release is available on FSRA’s website, and I encourage you to read it directly. 

FSRA’s findings, in their words: Drage “engaged in a prolonged and extensive pattern of misconduct, exposed investors to significant losses, failed to mitigate those losses, and derived significant economic benefit from her contraventions.” 

FSRA states she brokered hundreds of mortgages and other loans for a group of real estate developers, raising over $100 million from the investing public. The cited regulatory breaches include failing to disclose material risks, failing to disclose conflicts of interest, providing inaccurate valuations, failing to take reasonable steps to ensure mortgages were suitable, and failing to address inaccuracies in mortgage applications. The real estate companies behind those loans became insolvent and were granted CCAA creditor protection on January 23rd, 2024, exposing investors to real losses. Drage did not contest FSRA’s proposal, and the order was issued as-is. 

Why I Have to Disclose My Own History Here 

I knew Claire personally. She was a sponsor of my investor conference back in 2019. We referred clients to each other. She was, for a period, someone I considered a respected peer in this industry. 

At a certain point — years before any of this became public — something came up in my own network that concerned me. Out of fairness, and because there was a regulatory process that has only just concluded, I’m not going to get into specifics. But after that experience, I quietly made the decision to stop referring clients, and I took down the podcast episode I had recorded with her. I didn’t go public or issue a statement but I pulled back. 

I have to be honest with myself here. Almost three years passed between when I pulled back and when this all became public with the CCAA filing in January 2024. In that time, Claire continued to speak at other podcasts, sponsor other meetups, and appear at industry events. I wasn’t the gatekeeper for an entire industry. But I do sometimes ask myself whether I should have said more, sooner. It isn’t a clean answer. I had a hunch. I acted on it for myself and my direct clients but I didn’t broadcast it. Reasonable people can disagree about whether that was the right call. 

To the Investors Who Were Hurt 

Behind that one paragraph from FSRA about penalties are real people. Retail investors — often mom-and-pop lenders, sometimes retirees putting RRSP or TFSA money into what they thought was a safe, secured, first-mortgage investment — who lost money or had their capital tied up in an insolvency that may take years to resolve. 

If that’s you, I’m truly sorry. Nothing in the rest of this article is meant to lecture anyone already hurt. You did what a lot of smart, well-intentioned people did — you trusted someone licensed by the province, endorsed by the community, on stages with people you respected. That isn’t naive. That’s human. The rest of this is for everyone else who hasn’t yet made a similar decision and can still learn from what happened. 

Lesson 1 — Do Diligence on the Person, Not Just the Deal 

When you invest in a private mortgage, a syndicated mortgage, a Mortgage Investment Corporation (MIC), or any real estate syndication, you are not just investing in a property. You are investing in the people running the deal — their integrity, their processes, their disclosures, their willingness to tell you bad news when bad news happens. The property is a commodity. The operator is not. 

Concrete steps to do diligence on a person: check their licence status on the regulator’s website (FSRA for Ontario mortgage brokers, OSC for exempt market dealers). Search the regulatory enforcement database. Search their name with terms like “lawsuit,” “complaint,” “FSRA,” “OSC,” and “CCAA.” Ask for references from past investors on deals that went badly, not just deals that paid out — anyone can give you a happy reference. Ask about the deals that didn’t go well: How were they handled? How was the communication? Were losses disclosed and mitigated, or papered over? 

Pay particular attention to conflicts of interest. If the same person is the broker, the promoter, a connected party to the developer, and the recipient of transaction fees — that’s a stack of conflicts. It does not automatically disqualify the deal, but it has to be disclosed clearly and accounted for in how you size your investment. FSRA specifically cited failure to disclose conflicts of interest in this case. That isn’t a technicality. That’s the whole game. 

Lesson 2 — Private Lending Is Risk Capital, Not GIC Capital 

A lot of retail investors have been sold on private mortgages and MICs over the last decade as a “safe, secured, high-yield” alternative to GICs. That framing oversimplifies the actual risk. 

A first mortgage on real property is secured — yes. But secured against what? An appraisal value the broker provided? A property in a small town with a thin resale market? A development project where the value only materializes if construction finishes and lease-up succeeds? A borrower who may be connected to the broker arranging the loan? “Secured” is not the same as “safe,” and “high yield” exists for a reason: it is compensation for risk that’s real, even if you can’t see it on the pitch deck. 

When these deals go bad, they don’t go gently. They tend to go via CCAA filings or receiverships, and by the time you hear about it your capital is frozen for years while lawyers work through the priority stack. That isn’t a bond. It’s a fundamentally different risk profile, and it has to be sized in your portfolio accordingly. 

Well-structured private lending, with a trustworthy operator, genuine arm’s-length underwriting, and a property in a liquid market, absolutely has a place in a portfolio. What it doesn’t have is a place in your GIC bucket. If losing it would be devastating, it doesn’t belong here. 

Lesson 3 — Trust Your Gut, and Act on It 

When something feels off, act on it. Don’t wait for proof. Don’t wait for the regulator to catch up. Don’t wait until you can articulate the concern well enough to convince other people. Just protect your people. 

I pulled back years before any of this was public. I had no proof — just a hunch from one interaction that didn’t sit right with me. A lot of voices in our industry would have told me I was being paranoid, being unfair, burning a bridge with a successful operator for no reason. I pulled back anyway. Today I don’t regret that — I only regret not being louder about it earlier. 

If you’re a referrer — a realtor, a planner, a coach, a podcaster — the people who trust you are extending your reputation to the people you refer them to. That is a real responsibility. The stage someone stands on, the sponsorships they buy, the podcasts they appear on — those things confer credibility. All of us in this industry who platform people owe our audiences more diligence than we often do. 

The Common Thread 

Three stories. One thread. Ontario’s HST rebate surge is real but narrower for investors than the headlines suggest, and the investor cutoff has already passed. Alberta’s structural case is still intact, but the short-term picture is softer than the pitch decks say, and the real opportunity is patient capital buying turnkey from motivated sellers — not chasing preconstruction. And the FSRA ruling on Claire Drage is a reminder that in this industry, the people pitching you a deal deserve at least as much diligence as the deal itself. 

The headline is never the whole story. The loudest voices in a market are rarely the most informed. Your job as an investor is to do your own work — check the numbers, check the operator, trust your gut, underwrite on what is actually happening, not what a spreadsheet says could happen. 

Want Help Working Through This? 

If you’re trying to figure out whether to hold an Ontario rental, exit into Alberta, redeploy into the U.S., or stress-test a private lending position someone just pitched you — that’s exactly the conversation we have at iWIN Wealth Planning every week. 

I built this practice with my wife Cherry — a CPA who specializes in real estate tax — so our clients don’t have to navigate decisions like these alone, based on whoever had the shiniest pitch at the last meetup. We bring together real estate strategy, U.S. investment access through SHARE, tax planning, and estate and insurance planning into one coordinated plan. 

Reach out through iWIN Wealth Planning to start the conversation. 

Listen to the Full Episode 

The full audio version of this analysis is available on this week’s episode of The Truth About Real Estate Investing for Canadians.

🎧 Listen here

Until next week — invest wisely. 

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To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/ontario-hst-rebate-surge-alberta-cracks-%24600k-fsra/id1100488294?i=1000763729945

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/Ontario-HST-Rebate-SURGE–Alberta-CRACKS–600K-FSRA-Fine–Canadian-Real-Estate-2026-e3ie90u

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/cce7c607-9892-4548-b23a-dfa531d911db/the-truth-about-real-estate-investing-for-canadians-ontario-hst-rebate-surge-alberta-cracks-600k-fsra-fine-canadian-real-estate-2026

Audible: https://www.audible.ca/pd/B0GYMKW9HY?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/ibBWxozAre8

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.