Jeffrey Woods went from a broke college student to owning over 150 rental properties in less than six years. His secret? Joint venture partnerships and smart investing strategies that let him scale way beyond what his own money could buy.
Here’s how he did it, and what you can learn from his journey.
Starting Small: The First Property Win
Woods bought his first property in 1998 when he was barely scraping by in college. He saved every dollar he could and bought a distressed bank property. Then he got creative.
Instead of just renting the house to one family, he fixed it up and rented out individual bedrooms to college students. The result? The property not only paid for itself but put extra money in his pocket every month.
This early win showed him that real estate could work. But his second property taught him an even more valuable lesson.
Book Your Strategy CallThe Mistake That Changed Everything
Excited by his first success, Woods jumped into his second property too fast. He bought in a rough area, ended up with problem tenants, dealt with fire code violations, and had to go through the landlord-tenant board process.
It was a mess. But it taught him something crucial: he needed proper education and mentorship from people who had already done this successfully.
That shift changed his entire investing career. He stopped trying to figure everything out alone and started learning from experienced investors. His portfolio grew much faster after that.
How to Scale Without Your Own Money
After Woods maxed out his personal money, he discovered joint venture partnerships. This is where things really took off.
He found partners who had money but no time to manage properties. They were high-income professionals who understood real estate but were too busy with their careers and families to do the work themselves.
The setup was perfect. Woods brought the time, knowledge, and management skills. His partners brought the money.
The BRRRR Strategy in Action
Here’s exactly how Woods used the BRRRR strategy with his joint venture partners:
- Buy an undervalued property with partner money
- Renovate and add value to the property
- Rent it out to good tenants
- Refinance once the value increased
- Return capital to partners (often all or most of it)
- Repeat with the same or new partners
His partners loved this approach. When they got their money back, they kept wanting to invest in more properties. This created a cycle that let Woods scale to over 150 doors in under six years.
What Makes Joint Ventures Work
Not all partnerships work out. Woods emphasized several things that made his successful:
Take Your Time Vetting Partners
Don’t rush into partnerships just because you’re excited. Let that initial excitement settle. Look at the numbers carefully. Make sure you and your partner share the same long-term vision.
Woods only worked with people who wanted to hold properties long-term, especially multifamily properties. This alignment prevented conflicts down the road.
Get Everything in Writing
Every partnership needs proper documentation through a lawyer. This protects everyone involved and prevents misunderstandings later.
Communicate Clearly and Often
Keep your partners informed. Regular communication builds trust and keeps everyone on the same page.
The Growing Joint Venture Trend
Joint ventures are becoming more common in real estate, and it makes sense why. Property prices are much higher than they used to be. Many investors need partners to get into the market or grow their portfolios.
This strategy works perfectly for two types of people:
- Those with time and knowledge but limited money
- Those with money but no time due to careers and family
When these two types partner up, everyone wins.
The Challenges of Canadian Real Estate
After 25 years of investing in Ontario, Woods sees some serious problems for Canadian landlords.
Eviction Takes Forever
In Ontario, removing a non-paying tenant takes eight months to a year and a half. Woods estimates this single issue cost him hundreds of thousands of dollars, possibly millions, over his investing career.
That’s lost rent plus property damage that’s nearly impossible to collect on.
Rent Control Hurts Cash Flow
Ontario’s rent control limits how much you can raise rents each year. When mortgage rates jumped from 2% to 6-8%, many landlords saw their payments triple or quadruple. But they couldn’t raise rents enough to cover the increase.
Properties that used to make money now lose money every month.
Variable Rate Risks
Investors who chose variable rate mortgages to maximize cash flow got hit hard when rates rose. Many didn’t plan for increases because rates had been low for so long. Their cash-flowing properties quickly became cash drains.
Why Some Investors Look to the U.S.
These challenges led Woods to research other markets. After looking at options worldwide, he focused on certain U.S. markets, particularly Charlotte, North Carolina and Atlanta, Georgia.
Here’s what makes these markets attractive:
Fast Evictions
In landlord-friendly states like Texas, North Carolina, and Georgia, evictions take about 21-30 days instead of 8-18 months. This alone can save investors hundreds of thousands of dollars.
No Rent Control
Many U.S. states don’t restrict rent increases. You can set rents at market rates and adjust them when needed. This flexibility matters when costs rise.
Long-Term Fixed Rates
U.S. mortgages offer 30-year fixed rates. Investors who locked in rates at 2-4% keep those rates for the entire loan term. No refinancing risk every five years like in Canada.
Cash Flow-Based Lending
DSCR loans look at the property’s cash flow instead of your personal income. This matters for Canadian investors whose income doesn’t show up on U.S. tax returns.
Some lenders don’t even require positive cash flow to qualify, though you’ll get better rates if the property does cash flow.
Tax Deferral Through 1031 Exchanges
The U.S. tax code lets you defer capital gains taxes when you sell a property if you reinvest the money into another investment property. This means you can reinvest money that would have gone to taxes, compounding your growth over time.
Lessons for New Investors
Whether you’re investing in Canada or the U.S., these principles apply:
Invest in Your Education First
Woods credits his success to learning from people who had already done what he wanted to do. Don’t try to figure everything out alone. Good education and mentorship save you from expensive mistakes.
Don’t Rush Your Decisions
The biggest mistakes happen when you rush into deals because you’re excited. Slow down. Analyze the numbers. Vet your partners carefully. Make sure everyone shares the same goals.
Start Small and Scale Smart
Woods started with one property and a creative strategy. He learned from his mistakes. He got educated. Then he found a way to scale using partnerships.
You don’t need to own 150 properties to succeed. But if that’s your goal, joint ventures offer a proven path to get there.
Build Relationships
Your network matters. The relationships Woods built over the years now help him find partners and opportunities in new markets. Focus on creating value for everyone around you, not just yourself.
The Bottom Line
Scaling a real estate portfolio doesn’t require having all the money yourself. Joint venture partnerships let you grow beyond your personal capital limits by partnering with people who have different resources and goals.
The key is taking your time, getting proper education, documenting everything legally, and choosing partners who share your vision.
Whether you’re investing in your local market or looking at opportunities elsewhere, these principles will help you build a portfolio that creates real wealth over time.
Book Your Strategy CallFrequently Asked Questions
A joint venture is a partnership where one person provides the capital and another provides the time, knowledge, and management. The person with money gets a hands-off investment, while the person with expertise gets to scale beyond their personal funds. All partnerships should be documented legally with proper agreements.
You buy a property with partner money, renovate it, rent it out, then refinance based on the increased value. The refinance often returns most or all of the partner’s capital, which they can reinvest in another property. This lets you scale multiple properties with the same capital.
Evicting a non-paying tenant in Ontario currently takes between eight months to a year and a half due to landlord-tenant board backlogs. This is much longer than landlord-friendly U.S. states where evictions typically take 21-30 days.
A DSCR (Debt Service Coverage Ratio) loan qualifies you based on the property’s cash flow instead of your personal income. The lender looks at whether the rental income can cover the mortgage payment. This is particularly useful for Canadian investors buying in the U.S. since their Canadian income doesn’t appear on U.S. tax returns.
Look for partners who share your long-term vision and investment goals. Take time to vet them properly before committing. Make sure you both want the same things, whether that’s long-term holds, quick flips, or specific property types. Always document the partnership legally with a lawyer.
A 1031 exchange lets U.S. investors defer capital gains taxes when selling a property if they reinvest the proceeds into another investment property. This means you can reinvest money that would have gone to taxes, creating a compounding effect that dramatically increases portfolio growth over time.
U.S. markets offer several advantages including faster evictions (21-30 days vs 8-18 months), no rent control in many states, 30-year fixed-rate mortgages, DSCR loans based on property cash flow, 1031 tax exchanges, and more flexible lending options overall. These factors can significantly improve cash flow and reduce risk.
The biggest mistake is rushing into deals because of excitement. New investors should slow down, analyze numbers carefully, get proper education and mentorship, vet partners thoroughly, and make sure all parties share the same goals before committing to any deal or partnership.
