Host: Erwin Szeto, The Truth About Financial Independence for Canadians
Guest:Sadaf Chowdhury, Director of Investment Sales at Equitable
Investing for the New AI Generation With Only 25% Down Payment?
Canadian investors understand the power of a down payment because they have used mortgages to buy real estate for generations. In this episode, I sit down with Sadaf Chowdhury to discuss whether an investment loan with a 25% down payment may help suitable investors build wealth through professionally managed stock funds in the new AI economy.
Why Investors Are Looking Beyond Rentals
Many Canadian investors already have significant exposure to local real estate. Higher operating costs, tenant challenges, property maintenance and natural-disaster risk are encouraging some families to consider more passive investment options. That does not make real estate obsolete, but it can make diversification more important.
What Does 25% Down Mean?
The strategy discussed uses an investment loan in which a qualified investor contributes 25% and borrows the balance. It is not available or appropriate for everyone. Approval, interest rates, payment terms and performance are not guaranteed, and suitability depends on income, cash flow, risk tolerance and goals.
Professionally Managed Stock Funds and Estate Planning
Sadaf explains how professionally managed stock funds offered through an insurance contract may include death benefit guarantees, beneficiary designations and annuity settlement options. The exact legal, tax and estate results depend on the contract and personal circumstances.
Why AI Changes the Investing Conversation
AI is not limited to chatbots. The investment theme can extend across semiconductors, cloud computing, data centres, software and robotics. Rapid change may create opportunity, but it can also increase volatility and the difficulty of selecting individual winners.
Bottom Line
Investing for the new AI generation is not simply about buying AI stocks. It is about building a plan that combines suitable financing, professional management, diversification and the ability to remain invested through market cycles.
Join Me Live: Free Training on the $100,000 Investment Loan Strategy
The session will explain zero or 25% down investment-loan strategies, how prudent leverage may accelerate wealth building, and why suitability, cash flow and risk tolerance matter.
Educational purposes only. This is not individualized investment, tax or legal advice. Approval and performance are not guaranteed. Historical or simulated results do not predict future performance.
Here is exactly what I will walk through in 90 minutes:
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
Live Q&A — bring your questions, bring your skepticism
Two dates to choose from. Both cover the same content — pick whichever fits your schedule.
Quick Answers: AI Investing With a 25% Down Payment
Can Canadians invest with a 25% down payment?
A qualified investor may be able to use an investment loan that requires a 25% contribution. Approval and suitability depend on the lender and the investor’s finances.
What is 25% Down on the Stock Market?
It is TAFI’s name for an investment-loan strategy where an investor contributes 25% and borrows the balance for professionally managed stock funds.
Is an investment loan the same as a margin account?
No. Payment rules, collateral terms and liquidation rights can differ, so the specific agreement must be reviewed.
What are professionally managed stock funds?
They pool investor money in portfolios selected and monitored by professional managers. Some are offered through insurance contracts with estate-planning features.
How does AI affect investing?
AI creates potential opportunities across chips, cloud infrastructure, software, data centres and robotics. It also creates volatility and makes professional research important.
Who may be suited to an investment loan?
It may be a fit for someone with stable income, strong cash flow, a long time horizon and comfort with market declines.
Do investment loans guarantee better returns?
No. Borrowing magnifies outcomes, and neither approval nor investment performance is guaranteed.
Can these investments create income?
Investors may take profits or withdrawals over time, but available income depends on market performance and the financial plan.
How can these funds support estate planning?
Certain insurance contracts may include beneficiary designations, death benefit guarantees and settlement options. Terms vary by contract and circumstances.
Why are Canadians investing beyond real estate?
Some investors want greater diversification and fewer responsibilities related to tenants, maintenance and property operations.
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.
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.
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.
https://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2026/09/Youtube-thumbnails1-5-1.png7201280Hanifah Ahttps://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2017/06/TruthRectangleLogo.pngHanifah A2026-09-08 14:58:462026-09-08 14:58:53Investing for the New AI Generation With Only 25% Down Payment?
This episode is a bit different. My wife and business partner, Cherry Chan, sat down with this week’s guest for her own channel, Real Estate Tax Tips, and the conversation covered ground I wanted every TAFI listener to hear. Consider this a crossover.
Victoria Suen bought her first investment property in 2011, in Mississauga, at 19 years old. She couldn’t qualify for a mortgage on her own, so her sisters signed for it and she came in as a part investor, contributing the money. The property cost $260,000. She calls it beginner’s luck. It might have been. But 16 years later, she’s a licensed architect and the founder of BuildEx Design, and she’s turned that early real estate interest into a firm that helps investors do exactly what she once needed a mortgage for: build wealth on a piece of land.
What Victoria’s firm does now is different from a typical architecture practice. BuildEx works almost exclusively with what’s called the missing middle, and Cherry asked her to define it from scratch.
What Is the Missing Middle, and Why Did It Disappear
For most of a city’s history, housing came in 2 extremes: single family homes in the suburbs, and high rise condo towers downtown. The middle ground, duplexes, triplexes, fourplexes, and mid-rise apartments, mostly stopped getting built. Not because nobody wanted it. Because zoning stopped allowing it.
That’s changing. Victoria’s explanation is straightforward: continuing to sprawl outward means more roads, more schools, more fire stations, and more water servicing, all for the same number of people. Cities like Tokyo, New York, and London never built that way. They grew inward instead. Canadian cities are now doing the same thing, loosening zoning rules that used to require a single family home on every lot.
22 Feet Wide, 5 Units: What Toronto Allows Now
The specifics surprised even Cherry. In Toronto, Victoria’s team is designing buildings on lots as tight as 22 feet wide by 120 feet deep, and fitting 5 units on them. Nine wards in the city now allow up to 6 units with no special permission required, as long as the building fits the lot through standard setback rules.
There’s no parking requirement in Toronto for these projects, which is what makes the density possible in the first place. Victoria still asks every client whether their tenants will realistically need a parking spot, because building without it in the wrong location backfires at lease-up. Ottawa is going further: the city is eliminating its parking requirement entirely, effective September 2026.
The 3 Moving Parts Investors Get Wrong
Victoria breaks a missing middle project into 3 questions that all move at once: what can be built on the land, what it costs, and who will finance it. That means coordinating an architect, a general contractor, and a mortgage broker simultaneously, and Victoria says getting all 3 people pointed in the same direction is often the hardest part of a first project. BuildEx now offers a feasibility service specifically to solve that coordination problem before a client commits.
From design to permits typically takes about 5 months. Construction runs another 10 to 12 months. All in, Victoria tells clients to budget a year to a year and a half, assuming no surprises.
CMHC’s MLI Select: Where the Real Money Is
The financing detail that stood out most: a fourplex plus a garden suite, 5 units total, or a 6-plex, qualifies for CMHC’s MLI Select program. That unlocks 2 things. First, waived development charges, which Victoria puts at $50,000 to $80,000 per unit. On a 5 unit project, that’s $250,000 or more the city simply doesn’t collect. Second, more favorable financing terms than a conventional commercial mortgage.
On loan-to-value, Victoria was careful to correct a number that gets thrown around: while MLI Select theoretically allows up to 95% loan-to-value, she says almost none of her actual clients get there. The rent numbers don’t support it. Most are landing at 80 to 85% loan-to-value against the appraised value, which still means an investor can put in perhaps $1 million to $1.5 million in construction costs on top of a $1 million lot, end up with a building appraised at $4 million to $5 million, and pull the majority of that capital back out through refinancing. Victoria’s typical client is left with roughly $100,000 still in the deal.
This isn’t a flip. It’s a long-term hold, financed through a 5 or 10 year CMHC mortgage term, with most owners refinancing and holding rather than selling.
The Mistake Investors Keep Making
Ask Victoria for the most common error and she doesn’t point to construction cost. She points to rent. Investors project the top of the market, say $3,500 a month for a 3 bedroom unit, without checking whether tenants in that location will actually need a parking spot they don’t have. When the unit doesn’t rent at that number, it comes down, sometimes to $3,000, and at a 4% capitalization rate that $500 monthly gap moves the building’s valuation significantly.
Cheaper Entry Points Exist Too
Not every missing middle project needs to hit CMHC’s MLI Select thresholds. Victoria is seeing more investors buy properties for $600,000 in Toronto’s outskirts, or in Hamilton and Niagara, and do smaller duplex or triplex conversions that still cash flow without the scale of a full 5 or 6 unit build.
What’s Behind the Walls
The biggest renovation risk, in Victoria’s experience, is what you can’t see until demolition starts. On one project, her team planned to remove a roof and add stories, tying new construction into the existing foundation. Once the walls came down, the foundation turned out to be crumbling and had to be re-engineered from scratch, an unforeseen cost. New construction avoids that risk but comes with its own tradeoff: tearing down a century home means meeting current zoning in full, sometimes on a smaller footprint, and often requires shoring, temporary structural support to hold back the land when a new foundation goes in tight against a neighboring building.
Why She Started Her Own Firm
Cherry closed with a question that had nothing to do with zoning: why start a business at all, given the headaches Victoria had just spent 30 minutes describing? Victoria’s answer traced back to that 2011 property in Mississauga. She had an entrepreneurial itch that architecture school, and traditional architecture firms, didn’t make room for. Starting BuildEx let her combine the technical training with the business instincts she couldn’t exercise inside someone else’s practice.
Her honest answer on the biggest surprise of running it: how much of the job is personal development. Whatever goes wrong in the business tends to trace back to her as the owner, whether she’s ready to admit that or not.
Quick Answers
What is the missing middle in housing?
It’s the housing type between single family homes and high rise condos: duplexes, triplexes, fourplexes, and mid-rise buildings, which zoning rules stopped allowing for decades.
How many units can you build on a Toronto lot?
Some lots as narrow as 22 feet can fit 5 units. Nine wards in Toronto now allow up to 6 units with no special permission required, and there’s no parking requirement.
What is CMHC MLI Select and why does it matter?
It’s a CMHC financing program for projects of 5 or more units. It waives development charges, worth roughly $50,000 to $80,000 per unit, and offers more favorable financing terms than a conventional mortgage.
How much capital do investors typically need to leave in a missing middle project?
Victoria’s clients typically get 80 to 85% loan-to-value after refinancing, and are left with around $100,000 still invested in a project appraised at several million dollars.
Join Me Live: Free Training on the $100,000 Investment Loan Strategy
Victoria’s path started with real estate, but this show has always been about more than one strategy. If you want to see how Cherry and I think about building a second wealth engine alongside — or instead of — property, join me live
Here is exactly what I will walk through in 90 minutes:
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
Live Q&A — bring your questions, bring your skepticism
Two dates to choose from. Both cover the same content — pick whichever fits your schedule.
I didn’t record this one. Cherry did, and I’m glad she brought it back to TAFI. Victoria’s story starts the same way a lot of ours did, a first property bought too young to qualify for the mortgage herself, and ends somewhere none of us could have predicted from that starting point: a firm helping other investors do the same thing at a scale and financing structure that didn’t exist when she started.
The missing middle is one more example of what this show is about now. Not just rentals. Every legitimate path that gets someone out of the rat race, including the one where you learn to read a zoning bylaw.
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.
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.
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.
https://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2026/09/Youtube-thumbnails-33.png7201280Hanifah Ahttps://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2017/06/TruthRectangleLogo.pngHanifah A2026-09-01 16:44:252026-09-01 16:55:48Turning a 22-Foot Lot Into 5 Units: Victoria Suen on the Missing Middle, and What It Actually Costs to Build One
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
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.
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.
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.
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.
https://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2026/07/Youtube-thumbnails-32.png7201280Hanifah Ahttps://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2017/06/TruthRectangleLogo.pngHanifah A2026-07-13 16:32:512026-07-13 16:32:55He Exited His Ontario Real Estate & Podcast To Build REI Businesses | Andrew Hines
Host: Erwin Szeto, The Truth About Financial Independence for Canadians
Guest: Mozzie Chleilat, Account Manager Business Development, DUCA Specialized Lending
Real estate investors understand leverage better than almost anyone. You put 20% down, the bank funds the rest, and you build equity while someone else pays the mortgage. It’s one of the most powerful wealth-building tools ever invented.
But ask most Ontario landlords right now how they feel about the Landlord Tenant Board, and you’ll get a very different answer than you would have gotten in 2015.
Rent control. Anti-renoviction bylaws. Vacancy costs. Property management fees that assume a tenant who actually pays. The passive income promise has become an active management job for most investors, and the economics have shifted enough that many are quietly looking for a different path.
That path exists. It uses the same leverage principle that built wealth in real estate, applied to the stock market instead. No tenants, tribunals and 2 a.m. calls. And as of June 2026, Erwin Szeto sat down with Mozzie Chleilat from DUCA Specialized Lending to explain exactly how it works from the lender’s side.
What Is the 3:1 Investment Loan?
The investment loan is a leveraged lending product designed for investors who want exposure to professionally managed stock funds without putting up the full capital themselves. At DUCA, the structure is called the 3:1 loan: the client funds 25% of the investment as equity, and DUCA loans the remaining 75%.
In practice, it works like this. A client deposits $25,000 into a non-registered Equitable Life segregated fund account. DUCA lends $75,000 against that deposit. The client now has $100,000 invested, and all growth above that $100,000 belongs to them. They service the $75,000 loan at prime plus 0.75%, interest only. If the investment grows and the client wants to exit, they pay DUCA back and keep the rest.
The loan minimum is $50,000, which requires $16,667 of client equity. The maximum within the limited underwriting program is $1,000,000 personal and $1,000,000 corporate, meaning a couple with a holding company could access up to $2,000,000 in combined investment loans without full financial underwriting.
How to Qualify: Significantly Easier Than a Mortgage
The most striking feature of this product, for anyone who has tried to qualify for a new mortgage as a real estate investor, is how simple the approval process is for loans up to $1,000,000.
Within the limited underwriting program, DUCA does not require income documents or financial statements. The approval criteria are a clean credit bureau, no legal suits, judgments, or collection items, and a credit score of at least 650. That’s it. No T4, no NOA, no rental income schedule.
For investors who want above $1,000,000, or who prefer full underwriting, the TDSR maximum is 44%, and DUCA counts 90% of gross rental income toward that calculation. The major banks typically count 50%. For a real estate investor with significant rental income, that difference can be the gap between qualifying and not qualifying.
There is also a net worth qualification pathway. Investors who cannot meet TDSR requirements because of complex income situations, which describes a significant number of long-term real estate investors, can qualify by showing net worth of 1.5 times the loan amount with a reasonable liquid component to service the interest.
DUCA Does Not Report This Loan to Credit Bureaus
DUCA does not report the investment loan as a trade line item on the client’s credit bureau. The loan will appear as a secured item if a lender pulls a very detailed bureau, but it carries no balance history and no payment history. In practical terms, for most future lending scenarios, it does not affect the client’s ability to qualify for additional mortgages.
For a real estate investor still looking to acquire property in Canada or the U.S., this is a meaningful feature. The debt is there, but it is not visible the way a personal loan or car payment would be.
The Soft Margin Breach Program
The most common objection to any leveraged investment strategy is the margin call risk. If the market drops sharply and the portfolio value falls toward or below the loan balance, what happens?
Erwin shared his own experience on this. During COVID, he held AMD shares on margin with a different lender. When the position hit its threshold, there was no phone call and no email. The shares were liquidated overnight without warning. That stock has since gone up roughly 10 times from the price he owned it at.
DUCA’s approach is explicitly different. The program is described internally as a soft margin breach program. At 90 to 95% loan-to-value, DUCA contacts the client to give advance notice that the account is approaching a threshold. If the loan-to-value reaches 100%, the client has 30 days to either add cash to bring the balance back down to 99% loan-to-value, or move to a principal and interest payment for 3 months to pay down the loan. If the market recovers during that window, the breach resolves itself.
DUCA does not call loans. They work with clients through difficult markets, not against them.
The Right Investor Profile
This product is not for everyone. Mozzie is direct about that. The right client has a long-term investment horizon, meaning they are comfortable holding through market volatility without checking the account balance daily. They have sufficient cash flow to service the interest comfortably. They have a high risk tolerance, meaning they understand that leverage magnifies both gains and losses. And they are the kind of investor who sees a market dip as a buying opportunity rather than a reason to sell.
The investor profile that maps almost perfectly to this is a Canadian real estate investor who has used leverage for years and understands the principle intuitively. They already know what it means to put 20% down and let the asset grow. They already know how to sit through corrections. The difference is that this version of leverage has no tenants, no repairs, no legal hearings, and no exposure to Ontario rent control.
The Simple Math
Erwin put the comparison plainly during the conversation. A client can put 25% down in real estate, where the asset has historically grown 5 to 7% per year. Or they can put 25% down in a professionally managed stock fund, where the underlying market has historically grown over 10% per year, net of fees. Both use leverage. Both use the bank’s money. Only one comes with a tenant.
For investors who are already 80 to 90% allocated to Ontario real estate, diversifying into a leveraged stock fund position is not abandoning real estate. It is adding a different kind of asset to the mix, one that is more liquid, more passive, and historically has a higher expected return on equity.
How to Connect with Mozzie and DUCA Specialized Lending
Mozzie Chleilat is an Account Manager Business Development at DUCA Specialized Lending. He can be reached directly at mchleilat@duca.com or by phone at 416-460-0250. His colleagues Michelle Gervais and the broader DUCA Specialized Lending team at duca.com/specializedlending handle investment loan inquiries across Canada.
For investors who want to understand whether this strategy is appropriate for their situation, including whether they qualify and how to structure the 25% equity component, the starting point is a conversation with a licensed advisor who works with this product.
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:
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
Live Q&A — bring your questions, bring your skepticism
What is the minimum investment for a DUCA 3:1 investment loan?
The minimum loan is $50,000, which requires the client to deposit $16,667 of their own equity into the segregated fund account.
Does the DUCA investment loan affect my credit score or mortgage qualifying?
DUCA does not report the loan as a trade line item on the credit bureau. It may appear as a secured item, but it carries no balance or payment history. In most cases, it does not materially affect the ability to qualify for additional mortgages.
What happens if the stock market drops significantly?
DUCA operates a soft margin breach program. If the loan-to-value approaches 100%, DUCA gives the client 30 days notice and options: add cash, make principal and interest payments for 3 months, or wait for the market to recover. DUCA does not call loans.
How does rental income affect qualifying for this loan?
DUCA counts 90% of gross rental income toward the total debt service ratio for loans above $1,000,000. The major banks typically count 50%. This makes a material difference for investors with significant rental income.
Is this strategy right for everyone?
No. This product is designed for investors with a long-term investment horizon, sufficient cash flow to service interest comfortably, a high risk tolerance, and comfort with leverage. Anyone considering this strategy should speak with a licensed advisor to assess suitability.
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.
As a committed advocate for transparent and responsible investing, I disclose that I am a licensed insurance advisor with Open Concept Financial Group and an advisor working with DUCA Specialized Lending. I earn income when clients engage with the investment loan program described in this post. The investment loan strategies discussed are for educational purposes only and are not a guarantee of approval or performance. Fund performance figures referenced are simulated returns based on the underlying fund’s historical data, adjusted for segregated fund fees, as of May 31, 2026. Past performance does not predict future results. Suitability depends on individual income, cash flow, risk tolerance, and goals. Every investor should do their own due diligence and speak with a licensed advisor before making any investment decisions.
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.
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.
https://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2026/07/Youtube-thumbnails-31.png7201280Hanifah Ahttps://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2017/06/TruthRectangleLogo.pngHanifah A2026-07-06 15:59:362026-07-06 16:00:44The 3:1 Investment Loan: How Real Estate Investors Are Building Wealth Without Tenants
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:
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
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.
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.
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.
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.
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.
https://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2026/06/Youtube-thumbnails-30-1.png7201280Hanifah Ahttps://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2017/06/TruthRectangleLogo.pngHanifah A2026-06-26 14:30:502026-06-26 14:30:54He Worked 60 Hours a Week for 25 Years. Then He Installed a System and Sold for an 8-Figure Exit.
Host: Erwin Szeto, The Truth About Financial Independence for Canadians
Guest: Mike Schwarz, founder and CEO of MyZone AI, a Vancouver-based AI solutions company.
Most people add AI to their workflow slowly.
They try ChatGPT for a week, find a few uses, and move on.
Mike Schwarz went another direction. The founder and CEO of MyZone AI, based in Vancouver, negotiated a hall pass from his wife, adjusted his medication to sustain the hours, and spent 3 to 4 months working from the time his family went to sleep until 2, 3, and sometimes 4 in the morning.
The goal was to go all-in on AI agents. What he built: more than 200 autonomous agents running across 7 divisions of his business.
Schwarz has 25 years in technology. He was building social networks in 1999, before Friendster and MySpace existed and he founded MyZone in 2000 as a web development studio. Schwarz has watched the dot com boom, the mobile transition, social media, and e-commerce. And he says this transition is different.
“I’m measuring the window in months,” he said on a recent episode of The Truth About Financial Independence for Canadians. “Not years.”
What is AI, actually
Schwarz breaks it down simply. AI is a learning system that has been developing since the 1960s and 1970s, built on the idea that a machine can be trained to recognize patterns and predict outcomes. The early versions were basic: is this a cat? Yes or no. Each correct answer reinforced the model. Over millions of repetitions, it got good at predicting.
The breakthrough moment that most people experienced was November 2022 when ChatGPT went public. But underneath, the technology had been building for decades. TikTok and Instagram feeds were early AI. GPS systems used basic machine learning. Search autocomplete was an early form of prediction.
The version most people use today, a chatbot interface, is just one way to access the intelligence inside these models. Schwarz calls it a harness. It is a window into something much larger.
What is an agent, and why it’s different from ChatGPT
Most people think of AI as a conversation. You type something, it responds. One request, one reply.
An agent is different. Agents are designed for long-running autonomous tasks. You give them an objective: book me a flight, go through my inbox, reorganize my project management system. And they work toward that objective without needing step-by-step direction.
Schwarz describes the difference as how long they can run and whether they can make decisions on their own within defined guardrails.
His first real agent moment happened while preparing for a conference in Montreal. Claude Cowork had just launched the night before. He tested it by asking it to open his browser, go through his LinkedIn, and categorize his 183 unread messages. He left it running and came back 5 minutes later. It had sorted all 183 messages into categories and drafted responses for each one. He gave it some context about his relationships and told it to go ahead. Within 30 minutes, it had replied to every message except the 19 personal ones, which it had starred for him.
“I built a math game for my son in an hour,” he said. “Confetti, sound effects, an iPhone lockbox. He couldn’t get his screen time until he finished the exercise. He loved it.”
Why legacy software companies are struggling
Adobe, SAP, Oracle, and other major SaaS companies have seen their stock prices fall 50 to 60 percent over the past year. Schwarz has a theory about why.
The public narrative is that AI means smaller teams, which means fewer software licenses. Schwarz doesn’t buy that as the full story. His view: every business will eventually run its own custom software, built and maintained by agents. A custom CRM. Custom task management. Custom accounting. The future he sees is full ownership of software and data, not subscription to someone else’s platform.
“Every business built below this new operating system is essentially obsolete, they just haven’t realized it yet.”
Browser control vs. API connections: the speed and cost difference
When people see AI agents demonstrated for the first time, they often see browser control: an agent moving a cursor, clicking through a website, doing what a human would do manually.
Schwarz says browser control is the last resort. It is slow, expensive, and uses a lot of tokens (the unit of cost for AI model usage). The faster, cheaper option is an API connection: a direct plug into the software’s back end. Same task: an hour via browser control versus 4 minutes via API, at roughly 1/50th the cost.
He pointed out that 99% of software has a public API. For business owners wondering if their existing tools can be automated, the answer is almost certainly yes.
Where non-developers should start
For anyone with no technical background, Schwarz recommends starting with Claude Cowork. It is a safe playground that doesn’t require coding. For those with some technical ambition, Claude Code is another entry point. For building websites and simple software, Lovable is the most accessible tool in that space.
He makes an important distinction between vibe coding and agentic development. Vibe coding, a term coined by AI researcher Andrej Karpathy, means telling an AI to build something and letting it do whatever it wants. The results can look impressive but are often fragile, insecure, or hard to maintain.
Agentic development follows the same discipline as traditional software development: requirements, scoping, quality assurance. The difference is that a non-developer can now navigate this process with the right tools and agents. The coding is abstracted away. The thinking required is architectural and systemic, not syntactical.
“Any entrepreneur who has experience with systems and processes is already learning the skills they need to be an agentic leader,” Schwarz said. “The software developers are having to learn completely new skills. The architects are laughing.”
The 3 biggest mistakes businesses make adopting AI
Schwarz has coached hundreds of business leaders through AI adoption. He sees the same mistakes repeatedly.
The first is dismissal. Treating AI as a chatbot that hallucinates and makes mistakes, and stopping there. He estimates roughly 42% of Canadian employees are actively working against AI adoption in their organizations. Many leaders share the same instinct. The result is that companies fall further behind while their competitors build a structural advantage.
The second is moving too fast with too big an idea. Coming in with a plan to automate 80% of customer support in the first month triggers what Schwarz calls the immune system of a company. Culture pushes back. Change management collapses.
His recommendation: start with small, quick wins that have high ROI and visible impact. Those wins build the internal case for further adoption.
The third mistake is ignoring shadow AI. If a company has no official AI tools and no AI policy, employees are already using free consumer versions without anyone knowing. Free plans mean data is being shared with the AI provider. Client information, internal strategies, proprietary processes are leaving the building every day. “If you don’t have an official plan, they’re paying with your data,” Schwarz said.
How AI is changing education
Schwarz pulled his son out of school for a full year when AI began accelerating in 2023. He was building what he describes as a private AI school, influenced by models like Alpha School, which claims to deliver the core curriculum in 2 to 3 hours a day using adaptive AI instruction.
The key, he says, is hyperpersonalization. When AI instruction adapts to a child’s learning level, pace, and interests in real time, retention improves by 5 to 10 times compared to traditional classroom instruction. His example: teaching fractions using baking ratios for a child who loves to bake. The same math concepts, anchored to something the child already cares about.
Sal Khan, founder of Khan Academy, wrote a book on this topic called Brave New Words. Schwarz recommends it for anyone thinking seriously about AI in education.
The one thing
At the end of every episode, Erwin asks his guests for the one thing a listener should do this weekend.
Schwarz’s answer: master the art of learning.
“It’s not about being technical. It’s about being a sponge. Being adaptive. Being flexible. That is the skill.”
His method: consistent, scheduled repetitions in short sessions. 10 minutes in the morning, 10 minutes before bed. The same principle he used to go from a C minus to an A student in university. Small daily exposure keeps the brain processing in the background. The learning compounds.
“You’re not going to the gym on Friday for 12 hours,” he said. “You need a consistent schedule. Measure it. Build on it.”
Where to find Mike Schwarz
Mike Schwarz runs free monthly workshops at myzone.ai. Upcoming sessions include a workshop on becoming an agentic developer without coding experience (July 9). All previous workshop recordings, transcripts, and slides are available free on his website.
Quick Answers
What is the difference between an AI chatbot and an AI agent?
A chatbot handles one request at a time and waits for your next input. An agent can be given an objective and work toward it independently over a longer period, making decisions along the way within defined limits. Agents can use tools, access external systems, and complete multi-step tasks without hand-holding.
Do I need to know how to code to use AI agents?
No. Mike Schwarz recommends Claude Cowork as a starting point for non-developers. Agentic development, which is building more complex automated systems, can also be learned without writing code. The skills required are more architectural: understanding processes, defining requirements, and directing agents toward outcomes.
What is shadow AI?
Shadow AI refers to AI tools that employees use without company knowledge or approval. Because free AI plans often share user data with the AI provider, employees using these tools on personal accounts may unknowingly expose company information. A formal AI policy and approved tools prevent this.
What is vibe coding, and why is it risky?
Vibe coding means telling an AI to build something and accepting whatever it produces without following a structured development process. The results can look functional but may contain security vulnerabilities, expose private data, or break when updated. Agentic development follows the same quality assurance steps as traditional software development, just without the coding.
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:
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
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.
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.
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.
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.
https://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2026/06/Youtube-thumbnails-29.png7201280Hanifah Ahttps://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2017/06/TruthRectangleLogo.pngHanifah A2026-06-22 16:10:512026-06-22 16:10:54The guy who negotiated a hall pass to go all-in on AI
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.
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:
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
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.
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.
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.
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.
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.
https://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2026/06/Youtube-thumbnails-28-2.png7201280Hanifah Ahttps://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2017/06/TruthRectangleLogo.pngHanifah A2026-06-11 15:30:092026-06-11 15:30:12From Factory Worker to $300K Realtor: Milena Simsic on Windsor Real Estate, AI-Powered Marketing, and Building Wealth Without Landlord Headaches
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.
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:
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
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.
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.
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.
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.
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.
https://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2026/06/Youtube-thumbnails-27.png7201280Hanifah Ahttps://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2017/06/TruthRectangleLogo.pngHanifah A2026-06-05 13:57:402026-06-05 14:22:06Buying a Boomer’s Business: Ming Lim and Bryan Ma on Acquiring a 25-Year-Old Bookkeeping Firm, Vendor Take-Backs, and the Great Wealth Transfer
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:
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
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.
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.
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.
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.
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.
https://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2026/05/Youtube-thumbnails1-2-3-1.png7201280Hanifah Ahttps://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2017/06/TruthRectangleLogo.pngHanifah A2026-05-28 16:13:532026-05-28 16:14:07Why a 20-Year Canadian Finance Pro Drives 4.5 Hours to Buy $70,000 Cleveland Duplexes
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:
The complete $100,000 investment loan structure
The math — what $433/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
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.
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.
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.
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.
https://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2026/05/Youtube-thumbnails1-14-1.png7201280Hanifah Ahttps://www.truthaboutrealestateinvesting.ca/wp-content/uploads/2017/06/TruthRectangleLogo.pngHanifah A2026-05-26 15:59:542026-05-26 15:59:58How an Ontario Investor Built Two Apps for $800 With AI
