By Erwin Szeto | Co-Founder, iWIN Wealth Planning 

Recorded: July 2026 

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

Guest: Andrew Hines, co-founder of multiple US-based real estate acquisition companies, owner of Grotto Getaway, former host of The Andrew Hines Real Estate Investing Podcast.

Andrew Hines spent 5 and a half years building one of Canada’s top 3 real estate podcasts, alongside the host’s own show and Break Through Podcast. The Andrew Hines Real Estate Investing Podcast reached nearly 1.3 million downloads. Then, in 2023, at what looked from the outside like its peak, Andrew shut it down. 

He joined Erwin on The Truth About Financial Independence for Canadians to explain why, and to talk about what he built next: a US-based real estate business spanning house flips, land flips, and creative finance deals across Florida, Georgia, Texas, North Carolina, and Tennessee, plus Grotto Getaway, a glamping and cottage resort near Tobermory, Ontario, that did $655,000 in sales last year. 

Why He Walked Away From the Podcast 

For the first 2 and a half years, growth was steady, roughly 33% year over year. Meetups regularly drew 100 to 110 people on a random Wednesday night. Then interest rates rose. Guests stopped returning messages. By April 2023, one meetup that used to draw a full room pulled in 70 to 80 people, a noticeable drop, and interest kept falling from there. 

Andrew’s second son was due that November. He made the call to end the podcast in August, recorded a final episode 2 days later, and stepped away. 

Andrew hasn’t ruled out doing more, and he’s released occasional US investing episodes since, but the daily grind of the format was costing him money and had stopped being fun. He credits Erwin and Sarah Larbi with continuing to push through the same headwinds. 

Selling Everything in Ontario 

Andrew’s Ontario portfolio was built around student rentals in London, Ontario, in a neighborhood locally known as Soho. In 2015, he bought a single detached house there for $105,000, the cheapest property he owned. His student rental buys ran around $200,000, and additions expanded them to 900 to 1,100 square feet, pushing their value up to roughly $600,000. 

After the 2020 lockdowns, Andrew started rethinking his exposure. He loved student rentals from a management standpoint, but he saw a long-term risk in combining that asset class with the government’s willingness to shut things down. so, he decided Canada wasn’t going to be his long-term investing home, and he sold off the portfolio gradually, redirecting the capital into new construction in Cape Coral, Florida, and into Grotto Getaway. 

Andrew and his family are now in the process of establishing US tax residency, a move he’s discussing with his accountant. 

Building the US Business 

Andrew’s team runs 2 parallel businesses: house and land flips, and a course teaching Canadians how to do the same. Acquisitions agents work inbound seller leads generated through cold calling, Meta ads, and direct mail. Independent contractor realtors help close deals. A project manager and part-time admin round out the flipping side. 

His team finds motivated sellers using public US data unavailable in Canada, including tax liens, mechanics liens (any lien from a contractor, not just an auto mechanic), and notices of pending foreclosure. One core target group: tired landlords. 

Two deals from the conversation stand out. In Morrow, Georgia, Andrew’s team bought a rundown property for $95,000. Their realtor said she had to shower after walking through it. An $82,000 renovation, mostly cosmetic with no major mechanical work, brought it to market, and it sold to an investor for $237,000. 

In Jacksonville, Florida, his team bought a 47-acre parcel of land from a motivated seller who had originally purchased it for his daughter’s development plans. They spent just $5,000 clearing junk from the site, held it for about 20 days, and sold it for $478,000. No hammer, no plumber, no utility company calls. Profit: $163,000. 

Andrew is careful to note that deal isn’t typical. He estimates his team lands something in that range roughly once every other year. 

Why Ontario Real Estate, But Not US Real Estate 

Andrew has no interest in buying residential real estate in Ontario again. In the US, he still buys residential, both for flips and for the occasional subject-to deal his team can’t say no to. The difference, he says, comes down to landlord protections. Landlord-friendly US states can move a non-paying tenant out in a couple of months. In Ontario, that same process can take years. 

Construction economics tell a similar story. In 2023, Andrew’s team was building new construction in Cape Coral for roughly $105 per square foot in hard costs. Ontario hard costs at the same time ran $200 to $250 per square foot. He estimates Florida costs today sit closer to $125 per square foot, still a fraction of what a comparable garden suite costs to build in Ontario. 

The New Rules for Real Estate Investors 

Andrew’s read on the current market: the era of buying a cheap duplex, refinancing a year later, and repeating the cycle into a multi-million-dollar portfolio is over. What’s still alive is entrepreneurship. He describes his own flipping business less as real estate investing and more as marketing and business building. 

His advice for investors deciding what to do next: don’t go into anything expecting it to be passive from day 1. Build toward passive. Delegate the repetitive parts. Understand the value of your own time. Real estate investors, he says, were always small business owners. The difference now is the down payment isn’t the only thing standing between you and the work. 

Grotto Getaway: A Business Built for a Different Kind of Guest 

Away from real estate, Andrew owns Grotto Getaway, a glamping and cottage resort near Tobermory, Ontario. It started with prospector-style bell tents costing $10,000 to $12,000 to install. The property is zoned for 70 sites. Andrew’s team has developed 30 of them so far. 

Last year, Grotto Getaway did $655,000 in sales, roughly 60% growth over the year before, and that was before the property’s amenities even opened. A single unit typically pays for itself in its first year and generates $20,000 to $25,000 annually once stabilized. 

Direct bookings account for 60% to 70% of reservations, sparing the business the 16% to 19% commission charged by platforms like Airbnb, Booking.com, and VRBO. Google reviews sit at 4.8 out of 5 stars. One older trailer, bought for $7,800 and renovated for roughly $10,000, has generated about $25,000 a year for 4 straight years. 

The business runs heavily on Instagram, including collaborations with local influencers and occasional giveaways, one of which generated over 1 million views and 45,000 comments. The team currently employs 11 people, with more hiring planned for the summer season, including free trailer accommodation for seasonal staff. 

Andrew also notes a recent tailwind: shifting Canadian travel sentiment away from the US has driven more domestic bookings to Grotto Getaway, even as the same exchange rate dynamics raise his Florida construction costs. 

Frequently Asked Questions 

Why did Andrew Hines shut down his real estate podcast? Guest interest and listenership both dropped sharply starting in 2023. Andrew made the call in August 2023 and recorded his final episode 2 days later. 

Does Andrew Hines still own real estate in Ontario? No. He sold his entire student rental portfolio in London, Ontario, after reassessing his risk tolerance following the 2020 lockdowns. 

What states does Andrew Hines invest in? His team operates primarily in Florida, Georgia, Texas, North Carolina, and Tennessee, with land business expansion underway in Alabama. 

What is Grotto Getaway? A glamping and cottage resort near Tobermory, Ontario, that did $655,000 in sales last year with a team of 11. 

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.

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

Live Q&A — bring your questions, bring your skepticism

The complete $100,000 investment loan structure

The math — what $433 a month actually buys you over 5 and 10 years

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

How this fits alongside, not replacing, a real estate portfolio

Register Here: Saturday, September 12th Hybrid: Inperson and Zoom

The Bottom Line 

Andrew Hines didn’t wait for Ontario real estate to work again. He read the shift in landlord protections, construction costs, and government risk, and he moved his capital and his business model somewhere friendlier to both. His podcast didn’t survive the same shift in Canadian real estate sentiment that’s driving TAFI’s own rebrand, but his business did, because he stopped treating real estate as something to hold and started treating it as something to build. 

For investors weighing whether to keep waiting on Ontario rents to catch up, or to build something new instead, Andrew’s answer is clear: this is the age of the business builder, not the passive landlord. 

To Listen

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/He-Exited-His-Ontario-Real-Estate–Podcast-To-Build-REI-Businesses–Andrew-Hines-e3m0uf8 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/2809787f-ba8c-46cf-9da3-5b1f079f304a/the-truth-about-financial-independence-for-canadians-he-exited-his-ontario-real-estate-podcast-to-build-rei-businesses-andrew-hines

Apple: https://podcasts.apple.com/ca/podcast/he-exited-his-ontario-real-estate-podcast-to-build/id1100488294?i=1000776584753

Audible: https://www.audible.ca/pd/B0H8PSNDJZ?

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 referenced in this post are for educational purposes only and are not a guarantee of approval or performance. Suitability depends on individual income, cash flow, risk tolerance, and goals. Past performance is not indicative of future results. Every investor should do their own due diligence.

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: June 2026 

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

Guest: Byron Darlison, Founder Rise Vision, Certified Metronomics Coach, Accelerator Coach EO Toronto

He Worked 60 Hours a Week for 25 Years. Then He Installed a System and Sold for an 8-Figure Exit.

Byron Darlison on Business Operating Systems, the Great Wealth Transfer, and What Financial Independence Actually Looks Like.

Byron Darlison started Rise Vision in Toronto in 1992. He ran it for 30 years without raising a dollar of outside equity. For 25 of those years, he worked 60-plus-hour weeks, watched the business oscillate between good years and terrible years, and never fully understood what was making it unpredictable. 

In year 25, he hired a business coach and installed Metronomics as his operating system. In the 5 years that followed, profits went from break-even to 20% sustained net margins. Revenue growth went from low single digits to 15 to 20% per year. His personal work week dropped from 60-plus hours to under 10. He promoted his COO to run the company and stepped back to chairperson. In year 30, he sold Rise Vision to AUO Display Plus for an 8-figure exit, with no earn-out and no employment clause. His team still runs and grows the business today. 

He now coaches a small number of founders privately using Metronomics and serves as Mentorship Chair and Accelerator Coach at Entrepreneurs’ Organization Toronto. He publishes free frameworks, AI prompts, and tools at darlison.com. 

This is a conversation about what it actually takes to build a business that works without you, why most founders never get there, and why the next decade may be the best buying opportunity for small businesses in Canadian history. 

25 Years of Hard Work, Inconsistent Results 

Rise Vision did not start as a digital signage company. Byron spent years building software for Reuters to power LED screens on trading floors, then moved into banks, retail, and gradually what the industry started calling digital signage. For most of those years, the company was spread across 117 different industries. It had good years and bad years. The team was talented and deeply loyal, with some people staying more than 20 years. But consistency was elusive. 

Byron describes the dynamic bluntly: the team was exceptional at fighting fires. Nobody was in charge of fire prevention. There was no clear accountability structure, no defined priorities, and no rhythm that held the business to a standard quarter over quarter. 

He tried to fix it himself. He worked through Scaling Up, the Great Game of Business, Scrum, Basecamp, and lean startup principles. He spent a year attempting to self-implement a business operating system and made limited progress. Looking back, he identifies 4 reasons why it did not work. He was simultaneously the person building the accountability system and the person the system was supposed to hold accountable. When you are a player on the field, you cannot see the whole field. The team had watched him launch initiatives before and learned to wait them out. And without someone who had visibly done it before, there was nothing to counter the quiet skepticism that this time would be any different. 

What a Business Operating System Actually Is 

Byron defines a business operating system simply: a set of rituals at a specific cadence, captured in artifacts, that becomes religion. 

Not a framework you run for a quarter and then move on from. A rhythm that becomes so embedded that breaking it is unthinkable. Meetings that happen at the same time every week. Scorecards that are updated and reviewed in every session. Accountability structures where every person knows their domain, their critical number, and exactly what a good day looks like for them. 

The key insight he shares: the founder has to be the first to demonstrate the discipline. If the founder shows up late, everyone shows up late. If the founder skips meetings, everyone skips meetings. The system only works if the leader makes it non-negotiable for themselves first. 

For a company with a long history of operating in a loose way, he warns it takes about a year before the system starts to stick. The tell is when team members start self-correcting each other, saying we do not do it like that, we do it like this, before the founder has to say it. At that point, the organization has internalized the rhythm and it starts to compound. 

5 Years That Changed Everything 

The results Byron describes after installing Metronomics are specific and verifiable: 20% sustained net margins for 5 consecutive years, revenue growth of 15 to 20% per year, and a work week that dropped from 60-plus hours to under 10. Cash reserves built to many multiples of annual operating spend. 

At some point during this period, Byron realized something that very few founders are willing to admit: he was no longer the right person to be running the business day to day. His COO was. He promoted his COO to head of company, stepped back to coach the executive team, and found that running the business in under 10 hours a week, he was actually running it better than he ever had at 60. 

The return on the coaching investment, calculated conservatively over 5 years, was approximately 270 times its cost. 

How He Sold With No Earn-Out and No Employment Clause 

When Byron went to sell Rise Vision, the business was already operating without him in any active role. He was chairperson in name. The company had a proven operating system, predictable recurring revenue, a leadership team that ran and grew the business independently, and cash reserves exceeding a year of operating costs. 

That combination made the negotiating position straightforward. The company did not need to drop in revenue during a drawn-out acquisition process because Byron had no active role to distract from operations. He could devote full time to the negotiations without the business suffering. By the time the deal closed, revenue had grown by approximately 20% from where negotiations started. 

His advice for founders approaching an exit: the business needs to look like a machine to any acquirer. Predictable, self-running, not dependent on the founder. If it does, you can set your terms. If it does not, you are selling a job, and the buyer will price it accordingly. 

The Owner’s Outcome Framework 

One of the most practically useful frameworks Byron shares is what he calls the owner’s outcome: the exercise of getting precise about what you actually built the business to give you, before you make any strategic decision. 

He observes that most founders have a vague idea of freedom when they start, but never translate that into specific terms. How many hours do you want to work? What income do you need? What is your risk tolerance? What does your life look like at the 3-year mark if the business is working? 

Without that clarity, the business wanders. Every shiny object looks like an opportunity. Every crisis demands a response. There is no benchmark to measure whether the company is actually serving the founder’s goals or drifting away from them. 

This framework resonates particularly strongly in real estate. Erwin makes the connection in the conversation: he has coached real estate investors since 2010 and regularly encounters people whose stated why is more time with family, but who have bought a small business, in the form of a rental property, an hour from home, with a customer, the tenant, who has more rights than most business clients. The two do not reconcile. Byron’s response: they haven’t done the homework. 

The Definition of Strategy Is the Word No 

Byron’s framing of strategy is one of the cleanest distillations of the concept: if you know exactly what you want, 90% of what you see is noise by definition. Strategy is the discipline to say no to that noise, over and over, until what you are building becomes so specific and so well-understood that you win your market almost by default. 

Rise Vision’s pivot to K-12 digital signage in North America came from data, not instinct. After years of serving 117 different industries, the team looked at where the growth was consistent, where they won competitive deals, and where customers stayed forever. Education kept coming up. It was not glamorous. The procurement process was slow. The revenue per customer was not large. But the fit was undeniable. 

Focusing on that single market, with a single core customer, is what allowed the business to stop being spread across everything and start building genuine expertise. Once the product was built for one specific buyer, the sales and marketing costs dropped, the product team had clarity, and the competitive moat deepened every year. 

The Founder’s Dilemma 

Byron names the thing that kills most founder-led businesses before they ever reach an exit: the founder who is the hero. The one who jumps into every problem, gives the answer, and then wonders why the team never develops the capacity to solve problems without them. 

His reframe is simple and memorable. Instead of solving problems, ask: what do you recommend? Instead of giving the answer, ask by what date and how will you know it’s working? The goal is to make the person who owns the problem also own the solution, the measurement, and the learning. The founder becomes an editor and a mentor, not a firefighter. 

For anyone buying a business from a retiring founder, this is a critical due diligence signal. If the current owner is involved in everything, is the hero of every story, and cannot name a single decision the team makes without them, the buyer is not acquiring a business. They are acquiring a job. Byron puts the implication plainly: the team will not be able to independently execute once that founder exits. 

The Great Wealth Transfer and Why Boomer Businesses Are the Buying Opportunity 

Byron spent a day with Keith Cunningham, author of The Road Less Stupid, in Austin, and came away with a view he shares directly: there has never been an opportunity like this in our history. More businesses are coming up for sale right now than has ever happened before. Supply is high. Qualified buyers are scarce. Valuations reflect that. 

His sharper point is this: many of these businesses are badly run. Not terminal, not broken, but operating well below their potential because the founder never installed accountability, never defined a core customer, never built a system. That means the stated EBITDA is artificially low, the multiple is priced off that artificially low number, and a competent buyer who can install the missing infrastructure can earn back the purchase price in a fraction of the typical cycle. 

Cherry’s acquisition of a second accounting practice from 2 retiring owners in 2024 is a version of exactly this. The practice was well-established, the clients were loyal, and the owners were ready to exit. The opportunity came not despite the transition, but because of it. 

AI Running a 14-Agent Software Pipeline While Byron Sleeps 

Byron’s current project is a software development operation running entirely on AI agents. 14 agents, an orchestrator that manages the work queue, and a process where Byron tells the system what is in the backlog before he goes to bed and reviews the completed work at 6 a.m. The cost in human terms: approximately $300,000 a month in traditional development resources. His actual cost: a fraction of that. 

His advice for founders exploring AI: the one-off experiments are easy. Creating something reliable, scalable, and secure is not. The hard work is thinking through the architecture, defining the roles each agent plays, and building the methodology that makes the whole system trustworthy before you depend on it. 

He has published AI prompts on darlison.com that compress the time required to work through his core frameworks, including owner’s outcome, core customer analysis, and company values discovery, from days of consulting time to under an hour of structured AI-guided work. 

FAQ 

What is Rise Vision? 

Rise Vision is a cloud-based digital signage software company founded in Toronto in 1992 by Byron Darlison. It grew to serve organizations in over 100 countries, including schools, hotels, and universities. In 2022, it was acquired by AUO Display Plus, a Taiwanese industrial display manufacturer. 

What is Metronomics? 

Metronomics is a business operating system developed by Shannon Susko. It combines strategy, execution, and team alignment into a quarterly rhythm of meeting cadences, scorecards, and accountability structures. Byron Darlison used it to transform Rise Vision from a break-even company into a profitable, self-running business before selling. 

What is the owner’s outcome framework? 

The owner’s outcome is a framework Byron uses with every founder he coaches. It asks the founder to define precisely what they want their business to give them, in terms of income, hours, risk tolerance, and life design, before making any strategic decision. Without this clarity, businesses tend to drift toward whatever is urgent rather than whatever is important. 

What is the great wealth transfer and why does it matter for Canadian investors? 

Baby boomers own a massive number of privately held businesses in Canada. As they retire, those businesses need buyers. Because many of these businesses are poorly systemized and priced off artificially low earnings, buyers who can identify and fix the operational shortcomings can acquire businesses at significant discounts to their real earning potential. 

How is Byron using AI in his business? 

Byron is running a 14-agent AI software development pipeline from his home. He briefs the orchestrator each evening on the work backlog, the agents process tasks overnight, and he reviews output in the morning. He estimates the traditional human cost of equivalent output at approximately $300,000 per month. He has also published free AI-guided prompts at darlison.com for working through business frameworks. 

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

The Bottom Line 

Byron Darlison spent 25 years running his company the hard way. Not because he was not smart, not because the team was not talented, but because he never installed the structure that would have let the business work without him carrying it. Once he did, everything changed: the margins, the growth rate, the work week, and ultimately the exit. 

The lesson is not specific to SaaS companies or digital signage or Toronto tech founders. It applies to any business, including real estate portfolios that have turned into jobs, rental operations that never scaled, and accounting practices changing hands in Ottawa. The question underneath all of it is Byron’s question: what did you build this for, and is it delivering that? 

If the answer is no, the system is the fix. And the system is learnable. 

To Listen

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/60-Hour-Weeks-for-25-Years–Then-10-Hours-a-Week–Then-an-8-Figure-Exit–Byron-Darlison-e3l82cf 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/37865c02-70d7-42ff-a027-d45158fff0c8/the-truth-about-financial-independence-for-canadians-60-hour-weeks-for-25-years-then-10-hours-a-week-then-an-8-figure-exit-byron-darlison

Apple: https://podcasts.apple.com/ca/podcast/60-hour-weeks-for-25-years-then-10-hours-a-week/id1100488294?i=1000774184213

Audible: https://www.audible.ca/podcast/60-Hour-Weeks-for-25-Years-Then-10-Hours-a-Week-Then-an-8-Figure-Exit-Byron-Darlison/B0H6MTFLX3?source_code=ASSGB149080119000H&share_location=pdp

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 

Every guest on TAFI is here because they have done something worth studying. Milena Simsic did it faster, younger, and with less of a head start than most. Pay attention to the pattern, not just the result.

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. 

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: June 2026 

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

Guest: Milena Simsic, Founder, WindSocial Realty; Publisher, Windsor Real Estate Insider; Host, Windsor REI Social 

Milena Simsic made $300,000 in commissions in her first year as a realtor. She had no prior real estate connections, no social media following, and no marketing budget. What she had was a willingness to show up on TikTok and Instagram before anyone else in her market was doing it, and a formula she figured out in public. 

Three and a half years later, she runs Windsor’s most recognized investor-focused real estate team, publishes a newsletter with over 9,000 subscribers, and hosts a real estate investor community of 3,000 members that fills rooms with 100 to 200 people twice a year. She has also replaced her virtual assistant with Claude AI, built her CRM systems in an afternoon, and is now teaching other realtors how to do the same. 

This is an episode about what financial independence actually looks like when you build it from scratch, in a mid-sized Canadian city, with no inherited advantages. It is also, quietly, one of the clearest illustrations of why TAFI rebranded: the path out of the rat race does not always run through a rental property. 

The Windsor Market Right Now: What Is Holding and What Is Not 

Windsor has always been the most affordable large city in Ontario, and that affordability has acted as a cushion during the broader Canadian real estate correction. According to Milena, single-family homes in Windsor have held relatively steady because demand for primary residences has not collapsed the way it has in markets dependent on investors or short-term renters. 

The segments that have softened are student rentals and multi-unit investment properties. The immigration policy shifts of 2024 and 2025 hit student rental demand directly, and investment properties have followed. But for anyone buying a single-family home in Windsor, the fundamentals remain intact: low vacancy rates, a growing population, and a cost base that cannot be matched anywhere else in Ontario at the same level of amenity. 

Milena made the comparison plainly: for an investor deciding between a Toronto condo and a Windsor house right now, she said the Toronto condo has really tanked. The Windsor house, by contrast, still has a tenant market and a price point that works. 

🎙️ Listen to the podcast 

The Growth Drivers: EV Plant, Gordy Howe Bridge, and a Billion-Dollar Downtown 

Windsor’s economic story in 2026 is being written by 3 major developments. The EV battery plant is now operational and has brought thousands of jobs and thousands of new residents into the city. Traffic, which was always a non-issue in Windsor, has become a mild inconvenience, which Milena describes as a good problem to have. 

The Gordy Howe International Bridge, which was expected to open in March 2026, has been delayed by political interference from the U.S. side. The delay has created uncertainty, but the bridge remains a long-term economic catalyst for cross-border movement and commerce. 

The third driver is a billion-dollar downtown redevelopment announced by Farhee Development, with a major build expected to break ground in 2026. For a city the size of Windsor, a billion-dollar downtown investment is transformative. Milena notes that the timeline depends on when the developer wants to start, but the project is committed. 

$300K in Year One: How She Did It With No Connections and No Prior Social Media 

When Milena entered real estate, she made a decision that most new agents do not make: she treated the business like a marketing operation from day one. She had never used social media personally before getting her license, had no following, no network in real estate, and no referral base. 

She went on TikTok and started posting Windsor real estate content before anyone else in her market was doing it consistently. By the end of her first year, she had made $300,000 in commissions, entirely from TikTok and Instagram leads. More than half her clientele came from the Greater Toronto Area, drawn to Windsor by the price differential and guided to her by the content she was publishing. 

She attributes the result to spotting where the highest-leverage play was and going all in before the market caught up. The same logic has since driven her into AI. When she saw what AI could do for her business, she moved before most of her peers understood what they were looking at. 

Windsor Real Estate Insider: From a Client Resource to 9,000 Subscribers 

The Windsor Real Estate Insider started as a private resource for Milena’s clients, a document she called the Windsor Price Guide that helped investors understand the local market. The response from clients was strong enough that she decided to turn it into a proper publication. 

Since launching the magazine last year, it has grown to over 9,000 subscribers, all organic, with no paid acquisition. When you search Windsor real estate on Instagram or TikTok, Milena is the first result. The newsletter feeds from that visibility, and the visibility feeds from the newsletter. The two surfaces compound each other. 

Windsor REI Social, her investor community, operates on a similar logic. It began as monthly meetups that were drawing 30 to 70 people. She eventually moved to a biannual format and the events now draw 100 to 200 attendees, with guests traveling from outside Windsor including Toronto. 

Replacing a Virtual Assistant With Claude AI: What She Built and How Long It Took 

Milena’s AI implementation story is one of the most concrete in the episode. She was on the verge of hiring a second virtual assistant to handle CRM management, client responses, and backend administrative tasks. Instead, she set up Claude AI using the Cowork desktop tool and replicated the systems her VA had been running. 

The result was faster turnaround, higher accuracy, and a significantly lower cost than any human hire she could have made. She notes that she did not need any coding experience to build the systems. She wrote out the processes the way she would have written them for a human assistant, step by step, and Claude ran them. 

Her assessment of the competitive implications is direct: the top agents that implement AI are going to absorb all the business because no unassisted agent can compete with the response time and output volume that AI enables. She is now building a community for realtors who want to learn how to do what she did. 

EXP to Real: Why She Switched and What It Means for Realtors Choosing a Brokerage 

Milena announced on the show that she is leaving EXP for Real, an online brokerage that she describes as more focused on agent quality and community than on recruitment volume. Her critique of EXP is specific: many of the top earners in the EXP structure have never completed a real estate transaction. They joined to recruit, not to sell. 

Real, she says, actively discourages the pyramid recruitment dynamic and instead focuses on building a quality agent community. For Milena, the brokerage is primarily a platform to operate her own brand underneath. She does not believe the brokerage matters much to an agent’s success in terms of leads or training, but she values the culture and cost structure at Real over what she had at EXP. 

The Health Crisis That Doubled Her Business 

Two years ago, Milena developed thyroid issues she attributes in part to the stress of her first years in real estate, which coincided with a market peak and then a correction, all while she was working 40 to 60 hour weeks. She describes reaching a point where her health was failing and she recognized she was the bottleneck in her own business. 

The pivot started with salsa dancing, which she took up to feel better in her body after the autoimmune diagnosis. It cascaded from there into improved diet, therapy, changes in her sleep and work structure, and a recognition that working smarter and being present was more productive than grinding more hours. Since making those changes, her business has more than doubled. 

She entered the Windsor pageant a second time in 2026, roughly 3 years after her first attempt in which she did not place. This time she placed first runner up. She frames the second attempt as a personal milestone to close the chapter from 3 years ago and measure how far she had come. 

Advice for Young Canadians: Build Your Skill Set, Buy a Business, Stop Making Excuses 

In the closing exchange, Milena’s advice for young Canadians under economic pressure is blunt and specific. Build your skill set. Learn continuously. If you can, find a way to acquire or start a business, because employment is becoming less reliable as AI and economic shifts reduce traditional job availability. 

She notes the irony that while the economic environment is genuinely harder for young people, it has also never been cheaper or easier to acquire skills, start a business, or find a mentor. AI gives anyone access to expertise that previously required expensive professional services. The resources exist. The excuses are running out. 

On the business acquisition side, she endorses the vendor take-back financing model, noting that a significant proportion of businesses listed for sale are prepared to offer seller financing, making zero-down acquisition genuinely possible for a prepared buyer. 

Quick Answers 

What market does Milena Simsic specialize in? 

Windsor, Ontario. She focuses primarily on investor clients, more than half of whom come from the Greater Toronto Area. 

How did Milena make $300K in her first year as a realtor? 

Entirely through TikTok and Instagram content. She started posting Windsor real estate market content before any other agent in her market was doing it consistently, and built her lead pipeline from those platforms with no prior social media experience. 

Is Windsor real estate a good investment in 2026? 

Milena’s view is that single-family homes in Windsor have held up well. She says the Toronto condo has been harder hit than the Windsor house. Windsor has low vacancy rates, a growing population, and major economic development underway including an operational EV plant and a billion-dollar downtown redevelopment. 

What is Windsor REI Social? 

A real estate investor community of 3,000 members that Milena runs in Windsor. It hosts biannual events drawing 100 to 200 attendees, with speakers and networking focused on Windsor and southern Ontario real estate investing. 

How is Milena using AI in her real estate business? 

She replaced her virtual assistant with Claude AI using the Cowork desktop tool, which now handles CRM tasks, client responses, and backend administration. She built the systems herself in an afternoon with no coding experience. 

Why is Milena switching from EXP to Real? 

She says EXP’s culture prioritizes recruitment over agent quality, with many top earners having never completed a real estate transaction. Real actively discourages that dynamic and focuses on community and agent development instead. 

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

The Bottom Line 

Milena Simsic did not start with a network, a marketing budget, or a family in real estate. She started with a willingness to show up consistently in public before anyone else in her market understood why that mattered. That instinct, which she applied first to TikTok and then to AI, is what separates her story from a hundred other first-year realtor stories. 

What makes this episode particularly relevant for the TAFI audience is the portability of the model. Milena is not a real estate investor in the traditional sense. She is a business builder who happened to start in real estate. The leverage she used was not bank financing on a rental property. It was audience leverage, technology leverage, and the compounding effect of publishing consistently over time. Those tools are available to anyone. 

For investors who are tired of the LTB, tired of rent control, and tired of carrying properties that no longer cash flow, Milena’s arc is a useful reminder that the rat race has more than one exit. 

On Spotify: creators.spotify.com/pod/profile/erwinszeto/episodes/From-Factory-Worker-to-300K-Realtor–Milena-Si… 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/897f73b2-6d14-46d0-ab11-1ba2ab39a0f3/the-truth-about-financial-independence-for-canadians-from-factory-worker-to-300k-realtor-milena-simsic

Apple: https://podcasts.apple.com/ca/podcast/from-factory-worker-to-%24300k-realtor-milena-simsic/id1100488294?i=1000772208538

Audible: https://www.audible.ca/pd/B0H4VX8QJV?source_code=ASSGB149080119000H&share_location=pdp

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 

Every guest on TAFI is here because they have done something worth studying. Milena Simsic did it faster, younger, and with less of a head start than most. Pay attention to the pattern, not just the result.

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. 

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: Carlos Rodriguez

Quick story before we get into this week’s guest. 

Back at our September 2025 iWIN Wealth Summit, I walked through what I’ve been calling the 4-to-1 strategy. The idea is straightforward: $100,000 of investor capital combined with a $300,000 investment loan from the bank for a total of $400,000 deployed into professionally managed and index stock funds, including S&P 500 exposure. 

Since that September presentation, the market has appreciated more than 13%. After management fees and borrowing costs at 5.2%, that translates into an estimated 40.6% return on the investor’s original $100,000. Leverage cuts both ways, of course, and suitability matters tremendously. But if you’re a real estate investor or someone pursuing FIRE, you already understand this principle intuitively. We’ve all used prudent leverage in real estate for decades. 

Speaking of how leverage cuts both ways, Canadian real estate is in decline. Hamilton in particular is down 9% year-over-year, leading the entire country, as reported in the Globe and Mail. I’m glad I sold some Hamilton properties when I did. I wish I’d sold more. 

Especially our Hamilton duplex. The tenant stopped paying rent. The LTB hearing got postponed, then postponed again. Seven months in, I’m $12,000 deep in lost rent, a couple thousand more in paralegal bills, and still waiting. Even with all the best screening practices, I couldn’t have foreseen the tenant’s health failing and his white-collar tech job laying him off in the same year. I’m holding the bag as a private social safety net at my own expense. 

This is the world I’m operating in. And it’s the context that makes today’s guest worth your time. 

Meet Carlos Rodrigues 

Carlos Rodrigues spent 20 years in Canadian financial services. He holds licenses in mutual funds, life insurance both levels, and was a full mortgage broker, not just an agent, running four to five agents under him. He even started building out his own investment fund before the Canadian compliance costs shut that plan down. 

So when somebody with that résumé tells me the math in Ontario doesn’t work anymore, I pay attention. 

Today, Carlos is an active real estate investor focused on Cleveland, Ohio. He’s on the tools, on site, and driving four and a half hours each way from Hamilton to do it. He runs BRRRRs, joint ventures, and Section 8 rentals. He’s bought houses for as little as $70,000 that now appraise for over $170,000. 

This isn’t a fantasy pitch. Carlos is honest about what active cross-border investing actually looks like. 

The $70,000 Duplex Near the Cleveland Clinic 

The headline deal in this episode is a 3,000-square-foot duplex Carlos bought for roughly $70,000, including a $24,000 wholesale fee. The property sits within a two-minute drive of the Cleveland Clinic, one of the largest hospitals in the United States, in a zip code that’s actively gentrifying. 

The condition was rough. The main-floor toilet was on a diagonal and falling through the floor. But the bones were there. After renovations, the duplex appraised at $170,000. 

This is the kind of math that doesn’t exist in the Golden Horseshoe anymore. 

Section 8 Economics That Don’t Exist in Canada 

One of the most eye-opening parts of the conversation was Carlos’s breakdown of how Section 8 (US government rental assistance) works for landlords. 

He’s getting 20 to 30 percent above market rent through the program. He shared one tenant in the Coventry area, a retired nurse, who rents from him for around $1,400 per month. Of that, she pays $14. The federal voucher covers the rest. 

“We’re considered the socialist country,” I said to him at one point, “but we don’t have anything like this in Canada.” 

His strategy intentionally targets Section 8 because it builds a strong rent base. If the broader economy turns down and tenants in other rental classes start losing jobs, his voucher-backed rent keeps flowing. 

There’s risk on this side too. Federal funding can change. But compared to my Hamilton duplex, where a job loss meant seven months of zero income and a paralegal bill, the contrast is hard to ignore. 

What the US Lending Market Is Doing Right Now 

Carlos shared an email he just received from a US broker offering 100% loan-to-cost financing. That’s 100% of the purchase price plus the full renovation budget, lent against the after-repair value. 

This is the kind of headline that triggers 2008 comparisons. Both of us went out of our way to address that. As Carlos put it, in 2008 lenders were putting a mirror in front of borrowers’ faces and lending if it fogged. That isn’t what’s happening now. These loans go through proper appraisals, lead-safe certifications, rental licensing inspections, and the rest of the US regulatory apparatus. But the credit is loose, and that’s worth knowing. 

For context, just a few weeks before that email, brokers were quoting Carlos 90% loan-to-cost. The market is moving. 

The Joint Venture Partner Who Panicked 

Carlos didn’t sugar-coat the operator headaches. His most painful recent story involved a joint venture partner who, between Carlos leaving the site for a Home Depot run and returning, expanded the renovation scope from $65,000 to over $100,000. 

“The unfortunate thing with joint venture partners,” Carlos said, “is when people start to get uncomfortable, they start trying to shift to alleviate that pain. And sometimes they do things that, well, over-renovate.” 

It’s a useful warning for anyone considering JV deals across a border, especially when one partner has Ontario-market mental models and the other partner is dealing with Cleveland-market realities. The numbers in Cleveland support a different finish level, different price points, and different exit timelines. Mismatched expectations cost real money. 

The Contractor Problem 

Cleveland is busy. Contractors are scarce. Carlos’s contractor ghosted him a week before closing on his current project. 

He also raised a less-discussed reality: the immigration crackdown in the US is hitting the construction labor pool. Many of the most reliable workers in his market are of South American descent, and ICE enforcement has made them cautious about advertising their services publicly. Phone numbers are gone. Contractors now communicate through Instagram DMs and voice-over-IP. Even legal workers are wary. 

That tightens the supply of skilled trades. If you’re going into Cleveland for active renovation work, this is a real cost you need to budget around. 

Cleveland Appreciation: Real Numbers 

Carlos was disciplined about underwriting. His own deals assume 1.5 to 2 percent annual appreciation. He expects 2 to 4 percent over the next five years. 

Recent actual appreciation in Cleveland: 7 percent year over year. 

The gap between what he underwrites and what he’s actually getting is what builds margin of safety into his deals. This is the same lesson Sarah Coupland made last week, working backward from conservative resale values rather than chasing the optimistic case. 

The Side Yard Program 

One small detail that stuck with me: Cleveland has a side yard program where if your principal residence sits next to a vacant lot owned by the land bank, you can buy that lot for $100. If your investment property sits next to it, you can buy the lot for $500. 

Compare that to the Golden Horseshoe, where lots run hundreds of thousands of dollars. These are different markets with different math. The strategy you use in one doesn’t transfer to the other. 

The Bottom Line 

Canadian real estate isn’t dead. But the conditions that made it a passive vehicle for the average investor aren’t like they used to be. If you want to be an active operator, treat real estate as a business, and drive four and a half hours each way to do it, the Carlos Rodrigues path is open to you. 

If you want passive, you need to look elsewhere. Landlord-friendly US markets through the right partners. Leveraged stock-market positions through investment loans. Small-business acquisition. These are the paths the show will keep covering. 

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

That’s the next chapter.

Want the Whole Investment Loan Strategy Walked Through Live? 

This Saturday, May 30, 2026, I’m hosting a free training on the strategy that produced the 40.6% return I mentioned at the top of this post. 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 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 questions, bring skepticism 

In-person seats are capped at 40 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/20260602 

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

To Listen:

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/20-Years-in-Canadian-Finance–Now-He-Only-Buys-70K-Cleveland-Duplexes–Carlos-Rodrigues-e3k0v4j

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/d6ad4f99-c233-4397-884a-d8d94e54b29f/the-truth-about-financial-independence-for-canadians-20-years-in-canadian-finance-now-he-only-buys-70k-cleveland-duplexes-carlos-rodrigues

Apple: https://podcasts.apple.com/ca/podcast/20-years-in-canadian-finance-now-he-only-buys-%2470k/id1100488294?i=1000770024019

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: Sara Coupland, Real Estate Investor

Real estate investing is easy to talk about when markets are rising, financing is available, and the portfolio is growing. It gets much harder when life changes, assets must be sold, and the market no longer supports yesterday’s valuations. 

In this episode, Erwin sits down with Sarah Coupland, a long-time Ontario real estate investor, coach, construction operator, and owner of TAG Property Management. Sarah has been investing since 2007, built a personal portfolio of more than 60 doors, and manages about 300 units for herself and other investors. 

She also specializes in the kinds of properties most investors avoid: distressed multifamily buildings, mixed-use assets, older properties, and renovation-heavy projects that banks often will not finance. Now, as she works through the sale of her portfolio during divorce, she is also rebuilding from the other side using joint ventures, private money, and a more intentional strategy. 

Selling a Portfolio in a Difficult Ontario Market 

Sarah’s portfolio once included more than 60 doors. Today, because of her divorce, she is liquidating assets she had expected to keep long term. That process has forced her to reassess market values, buyer psychology, and the emotional side of letting go. 

One of her biggest lessons is corporate structure. Most of her properties were owned in corporations where she and her spouse were 50/50 shareholders, but Sarah held the controlling shares. That made the disposition process smoother because she could deal with lawyers, realtors, and purchasers without every decision becoming a back-and-forth negotiation. 

For investors building portfolios with spouses, partners, or joint venture investors, this is a major lesson: ownership and control are not always the same thing. The structure you set up when times are good can determine how manageable things become when life changes. 

Distressed Multifamily Is Not for Beginners 

Sarah specializes in highly distressed properties. One featured example is her 12-unit mixed-use building at 144 King Street West in Cobourg. The property had major deferred maintenance, a fire order against the third floor, wildlife inside the building, and units that were not suitable for habitation. 

The project was massive. Sarah purchased the building for approximately $700,000, structured an 80% to 85% vendor take-back mortgage, capitalized the interest into the purchase price, used private money and deferred payments, and ultimately ended up with about $1.7 million invested after a renovation budget of roughly $1 million. 

The property is now listed around $2.6 million, with roughly $21,000 per month in rent and a cap rate around seven, according to Sarah’s estimate during the conversation. Tenants pay utilities, the building has been extensively renovated, and much of the heavy lifting has already been done. 

The story is a strong example of forced appreciation, but it also highlights why these deals are not simple. Heritage requirements delayed the project by roughly six months over window requirements. An engineering miscalculation created an additional $80,000 electrical issue. The renovation took about two and a half years instead of the expected year and a half. 

That is the reality of distressed real estate investing: the upside can be significant, but the execution risk is real. 

Why Old Buildings and Mixed-Use Properties Can Work 

Many investors avoid old buildings, heritage districts, commercial units, and tertiary markets. Sarah often leans into them because lower competition can create better pricing. 

Her strategy is not to buy anything old blindly. It is to understand what can be fixed, what needs to be budgeted, what the market will support, and whether the numbers still work after realistic contingencies. She has also found that commercial tenants can add stability, and that commercial landlord-tenant issues are often simpler than residential issues under Ontario’s Landlord and Tenant Board system. 

That said, financing can be difficult. Mixed-use properties often do not fit neatly into standard CMHC or bank financing boxes. Sarah has used private lenders, vendor take-backs, seconds, and non-bank financing to make projects work when traditional lenders would not. 

Investor Appetite Is Returning, but Discipline Still Matters 

One of the most interesting parts of the conversation was Sarah’s take on today’s Ontario real estate market. On the sales side, she is seeing buyers still searching for discounts and often not believing the market has bottomed. On the acquisition side, however, she is also seeing aggressive activity. 

One off-market property she analyzed received 11 offers in three days and sold about $60,000 over asking. Another rough Peterborough triplex from a wholesaler sold over asking despite needing extensive work. 

Sarah’s conclusion is balanced: investors are starting to come back, but she refuses to chase deals. She works backward from conservative resale values, renovation budgets, investor return requirements, and contingency buffers. If the numbers do not work, she lets the deal go. 

That discipline matters in a market where comparable values can move quickly. Sarah shared a recent flip where expected resale values dropped from about $550,000 to $530,000 during the renovation period, and the property ultimately sold for $505,000. The deal still made money, but only because the numbers had enough room. 

LTB Challenges, Renovictions, and the Reality of Bad Buildings 

Sarah also spoke directly about Ontario’s landlord environment, including renovation-related bylaws and the pressure placed on private landlords to carry low-rent or non-performing assets. 

Her view is pragmatic. She respects housing needs, but believes governments should not expect private landlords to subsidize low-income housing indefinitely, especially when mortgage costs, repairs, insurance, and taxes continue rising. 

In distressed projects, Sarah says she often approaches tenants honestly. If the building is unsafe, she explains the work required, offers compensation, helps with moving, and documents the process properly. She is not evicting for sport; she is trying to fix buildings that may have water pouring down walls, electrical problems, structural issues, or unsafe conditions. 

For Landlord and Tenant Board matters, her advice is simple: communicate clearly, document everything, be honest, and bring evidence. If you made a mistake, admit it and move on. If you are at the board, make sure you are there for a valid reason and can support your position. 

Becoming a Full-Time Investor Is Not Retirement 

Sarah offered one of the most honest answers in the episode about becoming a full-time real estate investor. Too many people market it as “retire today” or “quit your job and become financially free.” Sarah’s reality was different. 

She worked as a financial advisor at CIBC, renovated after work, ate on the go, and spent evenings and weekends doing the hard labour. When she eventually left her job, she did not simply jump into the unknown. She created supplemental income through property management, bought a fourplex, and worked with joint venture partners and private money. 

Her warning is important: becoming a full-time investor is not retirement. Often, it is trading one job for another. The key is to build systems, income streams, a team, and a business that can eventually give you time back. 

Sarah’s personal goal was to be off when her daughter was off during the summer. With coaching and intentional planning, she eventually built rules around her acquisitions. If she did not have an offer accepted by the end of March, she stopped buying until after summer. That discipline helped her protect the life she was investing for in the first place. 

Education, Action, and Coaching 

Sarah credits much of her growth to education and community. She mentioned Durham REI and Quinton de Souza as important influences, especially in learning about RRSP mortgages, joint ventures, flips, BRRRRs, and vendor take-back mortgages. 

Her final advice for investors is straightforward: get educated, build your network, take action, and consider coaching when you are ready to move beyond basic investing. Her coaching is not aimed at complete beginners. It is better suited for investors who already own properties and want to move into multifamily, renovations, portfolio strategy, and more intentional investing. 

Sarah’s story is a reminder that financial freedom is not always a straight line. Sometimes the portfolio changes. Sometimes the market changes. Sometimes life changes. But with the right structure, conservative numbers, strong relationships, and the willingness to rebuild, real estate can still be a powerful path to wealth for Canadian investors. 

How to Connect with Sarah Coupland 

Sarah can be reached through her website at SarahCoupland.ca or by email at Sarah@TAGProperties.ca. Investors interested in her listed properties can also connect with Anita Bongers-Lewis and Chris Lewis at Doors to Wealth Real Estate. 

Quick Answers 

• How many units does Sarah Coupland manage? 
  Sarah Coupland manages about 300 units through TAG Property Management, including properties for other real estate investors. 
• How many doors did Sarah Coupland own? 
  Sarah’s personal real estate portfolio was over 60 doors before she began liquidating assets during her divorce. 
• What type of real estate does Sarah Coupland specialize in? 
  She specializes in distressed multifamily, mixed-use, and older Ontario rental properties where value can be created through renovations and better management. 
• Why does Sarah Coupland use private money and joint ventures? 
  She uses private money and joint ventures because many distressed or mixed-use properties do not fit traditional bank financing, especially during construction or major renovations. 
• What is Sarah Coupland’s opinion on the Ontario real estate market? 
  Sarah believes Ontario still has real estate investing opportunities, especially in small multifamily properties, but investors must be conservative with numbers and contingencies. 
• What advice does Sarah give about becoming a full-time real estate investor? 
  She says becoming a full-time investor is not retirement; it is often trading one job for another unless you build income, systems, and a team. 

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/Rebuilding-Wealth-After-Divorce-Sarah-Coupland-on-Ontario-Multifamily–Distressed-Properties–and-Creative-Financing-e3je3l3 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/44dcec71-076a-479c-99c2-720b8f10a5aa/the-truth-about-real-estate-investing-for-canadians-rebuilding-wealth-after-divorce-sarah-coupland-on-ontario-multifamily-distressed-properties-and-creative-financing

Audible: https://www.audible.ca/podcast/ITEM-NAME/B0H1V3FMG2?source_code=ASSGB149080119000H&share_location=pdp

Apple: https://podcasts.apple.com/ca/podcast/rebuilding-wealth-after-divorce-sarah-coupland-on-ontario/id1100488294?i=1000768392581

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.