Quentin D’Souza was a public school teacher with a master’s degree and a clear path to becoming a principal. Then his real estate portfolio grew big enough to replace his teaching salary. At 40 years old, he left teaching behind to focus on real estate full-time. Today, he owns at least $80 million in real estate across Canada and the United States.
His journey from one property to 17 apartment buildings shows what’s possible when you combine the right strategies with consistent action. Here’s how he did it—and how you can apply these lessons to your own investing.
The First Three Properties Are the Hardest
Quentin bought his first property in 2004. But the real growth started in 2008, when he began buying three to four properties per year.
Here’s something important: after the first three properties, investing became more like a game than a struggle. Those first few deals are tough because everything is new. But once you push through them, the process gets much easier.
Every deal involves what Quentin calls “the three F’s”:
- Finding the right property
- Getting the funds together
- Being able to finance the property
The key insight? You don’t have to bring all three yourself. This is where partnerships and creative deal structuring come in. Quentin wishes he’d learned this sooner—it would have sped up his early growth.
Book Your Strategy CallThe BRRRR Strategy Before It Had a Name
Quentin used the BRRRR strategy long before anyone called it that. His approach was simple:
- Buy properties that needed work
- Fix them up
- Rent them out long-term
- Refinance to pull out equity
- Repeat the process
This let him build a portfolio of cash-flowing assets without running out of money. He also brought in partners during this phase. Some of the people he partnered with back then are still his partners today—proof that treating people right pays off long-term.
Why Bigger Buildings Are Actually Easier
As Quentin’s portfolio grew, he shifted from single-family homes to apartment buildings. Now he focuses on 40 to 50-unit buildings, and he finds them much easier to manage than lots of small properties.
Here’s why larger buildings make sense:
Better Systems and Teams
At scale, you can afford professional infrastructure. Quentin uses a third-party accounting firm for year-end financials, a dedicated bookkeeping company for monthly books, and a property management team with regional focus. This creates oversight, efficiency, and real scalability.
The Numbers Get Simpler
It sounds backwards, but larger numbers are actually easier to work with. Dealing with tens of thousands of dollars is just adding another zero compared to dealing with hundreds. The principles stay the same—the numbers just get bigger.
One Corporation Per Property
Quentin’s corporate structure is straightforward: one corporation per property.
This approach gives you:
- Cleaner financing—lenders can clearly see what each entity owns
- Easier bookkeeping—each property’s finances are completely separate
- Transparency—the financial picture of each asset is crystal clear
- Partnership flexibility—much easier when partners want to enter or exit
The ownership structure is layered. The property-holding corporation owns the building, and separate corporations own shares in the property-holding corporation. This provides both clarity and flexibility.
Every Deal Came Through Relationships
Here’s something remarkable: Quentin owns 17 apartment buildings and hasn’t bought a single one off the MLS. Every single acquisition came through relationships.
Buying off-market gives you huge advantages:
- Less competition—you’re not bidding against multiple buyers
- Better pricing—sellers may accept less to avoid the hassle of listing >
- Flexibility—deal terms can be more creative
- Speed—transactions can close faster
Your reputation is everything in this business. Quentin keeps his focus tight—the 401 Corridor from Toronto out to Ottawa. This concentrated approach builds deeper market knowledge, stronger networks, and more efficient operations.
The Mindset Shift That Changes Everything
Quentin could have bought his 202-unit, seven-building portfolio three years earlier than he did. The delay wasn’t about money or capability. It was mindset.
He was stuck thinking deals of that size weren’t for him. Then he started talking to investors who were further along. Those conversations expanded his vision of what was possible.
His advice for breaking through mental barriers? Just add a zero to whatever you’re currently doing.
- Comfortable with $100,000 deals? Push for a $1 million deal
- Comfortable with $1 million deals? Try a $10 million deal
Each time you complete a deal at a new level, the next one becomes much more approachable. The first deal at any new scale is always the hardest, but it creates a new baseline for what feels normal.
Creating Value in Commercial Real Estate
Commercial real estate value is based on Net Operating Income divided by the cap rate. This means you can directly control property value through improvements.
Cut Expenses
Small changes add up fast:
- Convert to LED lighting—lower electricity and maintenance costs
- Install water-saving fixtures—dramatic reduction in utility bills
- Upgrade HVAC systems—one of the biggest expense items
Every dollar you save in annual expenses increases your property value. At a 5% cap rate, saving $1,000 per year adds $20,000 to your property value.
Increase Revenue
As units turn over naturally, renovate them and bring rents to market rates. You can also offer buyouts to tenants, which costs more but speeds up the process.
Buy Below Replacement Cost
New construction costs about $300 per square foot on average. Quentin focuses on buying existing buildings well below these costs. This gives you immediate equity and a built-in margin of safety.
Problems Happen Every Day
Real estate always comes with challenges. A roof flew off one of Quentin’s properties at 2:00 AM. His property management team got on-site immediately, and contractors were working on repairs by the next day.
The key is having processes and systems to handle problems efficiently. Quentin has written two books on property management because he’s obsessed with creating standard operating procedures for everything.
Good systems turn your real estate portfolio from a collection of properties into a real business with consistent, repeatable processes.
Getting Started Today
The most important step is the first one. Those first three properties will feel hard, but they get easier fast. You don’t need to figure everything out alone—find partners who can fill in the gaps where you’re weak.
Focus on building relationships before you need them. Your reputation will open doors to deals that never hit the market. Stay ethical, play by the rules, and treat people right. This approach builds a sustainable business that can operate for decades.
And remember: whatever level you’re at right now, you can probably handle more than you think. Just add a zero.
Book Your Strategy CallFrequently Asked Questions
Most investors find that after the first three properties, the process becomes much more manageable. Those first few deals are the hardest because everything is new, but once you push through them, investing becomes more like a game than a struggle.
No. Every deal involves three elements: finding the property, getting the funds, and securing financing. You don’t have to bring all three yourself. Many successful investors use partnerships and creative deal structuring to complete deals without providing all the capital themselves.
Most experienced investors recommend one corporation per property. This makes financing cleaner, bookkeeping easier, and provides complete transparency. It also makes it much simpler when partners want to enter or exit investments.
Off-market deals come through relationships. Focus on building genuine connections with other investors, brokers, and property owners in your target area. Your reputation is what opens doors to deals that never get listed publicly.
Actually, many investors find larger buildings easier. At scale, you can afford professional infrastructure like dedicated property management teams, third-party accounting, and specialized bookkeeping. This creates better systems and more efficient operations than managing many small properties.
Commercial property value is based on Net Operating Income divided by cap rate. You can increase value by cutting expenses (LED lighting, water-saving fixtures, HVAC upgrades) or increasing revenue (renovating units and raising rents to market rates). At a 5% cap rate, every $1,000 saved in annual expenses adds $20,000 to property value.
Start by adding one zero to whatever you’re currently comfortable with. If you handle $100,000 deals, push for $1 million. Also, talk to investors who are further along than youu2014these conversations will expand your vision of what’s possible. The first deal at any new level is always hardest, but it creates a new baseline for what feels normal.
Focus on a specific region rather than spreading yourself too thin. A concentrated approach builds deeper market knowledge, stronger local networks, and more efficient operations. You can also standardize your processes when properties are in similar markets.
