5 Reasons New Real Estate Investors Fail Before They Even Start
- Wayne Hillier
- Jun 5
- 3 min read
By Wayne Hillier, Real Estate Investing Masters
June 05, 2025 | Edmonton, Alberta
Most Canadians agree that real estate is one of the most powerful ways to build long-term wealth. Yet thousands of aspiring investors never make it past the research phase.
As someone who coaches new investors daily through the REI Masters Mentorship Program, I’ve seen it time and again: people want to invest, they know the benefits, but they still don’t take action. In fact, a recent RE/MAX Canada report found that 26% of Canadians say real estate is the best long-term investment, yet fewer than 10% actually own investment property.
So, what’s holding them back?
Below are five of the most common reasons people fail before they even start, and how you can make sure that’s not your story.
1. Fear of Making a Mistake
Fear is real. And it's not always irrational. People worry about picking the wrong property, overpaying, or ending up with a nightmare tenant. But fear is also the number one reason people stay stuck.
“I didn’t have all the answers when I started either,” I’ve said to countless students. “But I took the first step, then the second, and I figured it out along the way.”
The antidote to fear is preparation, not perfection. When you understand your numbers and follow the fundamentals, risk becomes manageable.
2. Waiting for the Perfect Time
The perfect time doesn’t exist. The market will always fluctuate, interest rates will always move, and there will always be reasons to wait. But as the saying goes, the best time to plant a tree was 20 years ago. The second-best time is today.
In Alberta, market fundamentals remain strong. Edmonton, for example, saw a 3.5% year-over-year increase in average home prices this spring, according to the RAE May 2025 Market Report. Rental demand is climbing, and the province’s pro-landlord policies continue to attract investors from across Canada.
Waiting usually isn’t about timing, it’s about uncertainty.
3. Trying to Learn Everything First
Paralysis by analysis is a real threat to would be investors. Many people spend years watching YouTube videos and listening to podcasts without ever running the numbers on an actual deal.
Real estate isn’t about mastering theory. It’s about learning just enough to take action and then learning the rest on the field.
4. Believing They Need More Money Than They Do
This is one of the biggest myths in real estate, that you need hundreds of thousands in the bank to get started. In reality, many investors get into their first deal with a combination of joint ventures, private lending, or even a home equity line of credit.
At REI Masters, we teach five creative financing strategies that can help bridge the gap between wanting to invest and being able to. And we stress-test every deal using the 5% Rule™ to make sure cash flow is sustainable, even when using other people’s capital.
Money doesn’t have to be the barrier. But not knowing your options will be.
5. Lack of a Plan or Accountability
Finally, many new investors fail simply because they go it alone. They don’t have a plan, they don’t know what kind of property to buy, and they don’t have anyone to push them forward when doubt creeps in.
That’s why mentorship matters. It’s not just about learning strategies, it’s about having someone who can help you make decisions, spot red flags, and stay on track.
As I often remind our students: “Nobody builds a successful business without guidance. Real estate is no different.”
Getting started in real estate is hard, but it’s not impossible. The people who succeed aren’t necessarily the ones who know the most. They’re the ones who take the first step, then keep on pushing through.
If you're feeling stuck, know this: every investor you admire once stood where you are. The difference is, they didn’t stay there.
Listen to Today’s Episode:
Real Estate Investing Morning Show – Hosted by Wayne & Gabby Hillier
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